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Absolute configuration determination of diasteriomeric iron complexes by X-ray diffraction

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Absolute configuration determination of diasteriomeric iron complexes by X-ray diffraction

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Content A B S O L U T E C O N FIG U RA TIO N D ETER M IN A TIO N * > * < K t , O F DIASTERIOM ERIC IRON C O M P L E X E S BY X -R A Y D IF FR A C T IO N by Chaw Kuo Chou A T h e s is P r e s e n t e d to the F A C U L T Y O F THE G R A D U A T E SCHOOL UNIV ERSITY O F SO U T H E R N CALIFO RN IA In P a r t ia l F u lfillm e n t of the R e q u ir e m e n ts for the D e g r e e M A STER O F SCIEN C E (C h e m istr y ) A ugust 197 5 UMI Number: EP41662 All rights reserved INFORMATION TO ALL USERS The quality of this reproduction is dependent upon the quality of the copy submitted. In the unlikely event that the author did not send a complete manuscript and there are missing pages, these will be noted. Also, if material had to be removed, a note will indicate the deletion. U M T Dissertation Publishing UMI EP41662 Published by ProQ uest LLC (2014). Copyright in the Dissertation held by the Author. Microform Edition © ProQ uest LLC. All rights reserved. This work is protected against unauthorized copying under Title 17, United States Code ProQuest’ ProQuest LLC. 789 E ast Eisenhower Parkway P.O. Box 1346 Ann Arbor, Ml 4 8 1 0 6 - 1346 U N IV E R SITY O F S O U T H E R N C A L IF O R N IA T H E G R A D U A T E S C H O O L U N IV E R S IT Y P A R K L O S A N G E L E S , C A L IF O R N IA 9 0 0 0 7 This thesis, written by CHAW KUO CHOU under the direction of h..is—Thesis Committee, and approved by all its members, has been pre sented to and accepted by the Dean of The Graduate School, in partial fulfillm ent of the requirements for the degree of Dean Date My.J975_ C C 5 5 2 . s o 4 THESIS COMMITTEE To m y p aren ts and Chu Chu ii ACKNOWLEDGMENTS I should lik e to e x p r e s s m y deep a p p recia tio n to D octor R obert B au for h is e x t r e m e p a tien ce and guidance. TABLE OF CONTENTS P a g e A C K N O W L E D G M E N T S. ................................................... iii LIST O F T A B L E S .................................................................. v LIST O F F I G U R E S ....................... vi P R E F A C E .............................................................. vii Chapte r I THE M O L E C U L A R S T R U C T U R E O F TWO IRON C O M P L E X E S : ( + ) - (? T -C 5H 5 )Fe(C O ) ( P P h 3 )C H 2 O C 1 0 H 19 A N D ( +) - ( 7T - C 5 H 5) Fe(C O ) ( P P h 3) CH2 C O O C 1 0 H i g ................................ 1 II THE S T R U C T U R E A N A LY SIS O F ( r] 5 -C g H 9 ) 67 (rj 7 - C 8 H9 ) R u 3 (CO)6 ........................................................ R E F E R E N C E S .................................................................................................... 97 LIST OF TABLES Table P a g e 1 C r y s ta l D a ta ............................ 7 2 P o s it io n a l and T h e r m a l P a r a m e t e r s ........ 12 3 I n te r a to m ic D is ta n c e s and A n g l e s ............ 17 4 O b s e r v e d and C a lcu la ted S tru ctu re F a c t o r s . . . 21 5 C r y s ta l D a ta..................................... 30 6 P o s it io n a l and T h e r m a l P a r a m e t e r s ........ 33 7 In te r a to m ic D is ta n c e s and A n g l e s ............ 42 8 O b s e r v e d and C a lc u la te d S tru ctu re F a c t o r s . . . 48 9 P o s it io n a l and T h e r m a l P a r a m e t e r s ....... 74 10 In te r a to m ic D is ta n c e s and A n g l e s ............ 77 11 O b s e r v e d and C a lc u la te d S tru ctu re F a c t o r s . . . 80 v LIST OF FIGURES F ig u r e Pa-ge 1 The CD S p e c tr a of ( 7T-C5 H 5 )F e (C O )(P P h 3 ) C H2 O C 1 0 H iq and (TT-C cH tO FefC O H PPho) CH'2 C O O C 1 0 H i 9 ........................... 4 i 2 The G e o m e tr y of ( 7 r -C 5H 5 )F e (C O )(P P h 3) c h 2o c 1 0 h 1 9 ................................................................................ 10 3 The G e o m e tr y of ( ^T-C5H 5 )F e (C O )(P P h 3) c h 2 o c 1 0 h 19 . ...................................................................... 11 ; 4 The G e o m e t r y of ( 7f-C 5H 5 )F e (C O )(P P h 3) C H 2 C O O C 1 0 H 19 ................................ 47 3 r The R ea ctio n of a W hole S e r i e s of ( r - C 5H5)F e(C O )(P P h 3)X C o m p o u n d s ................... 63 6-; The G e o m e t r y of (C gH 9 )2 R u3 (CO)6 .............................. 73 vi P R E F A C E X - r a y d iffraction m eth o d s w e r e u s e d to d e te r m in e the ab solu te co n fig u ra tio n s of two p s e u d o -te tr a h e d r a l iron c o m p le x e s w h o se co n fig u ra tio n s w e r e p r e d ic te d e a r l ie r by c i r c u la r d ic h r o is m s p e c tr o s c o p y . The two com p oun ds stu d ied w e r e (+ ) g - ( TT’-C gH g) F e (C O )(P P h 3 )C H 2 O C 1 0 H 19 and (+ )5 7 8 -( 7T-C5H 5)F e (C O )(P P h 3 ) CH 2 C O O C 1 qH 19 . The s tr u c tu r e d ete r m in a tio n of the c o m p le x » (CgH9 )2 R u3 (CO)6 is a ls o p r e se n te d . V I1 C H A P T E R I THE M O L E C U L A R S T R U C T U R E O F TWO IRON C O M P L E X E S : ( +)578-(tT - C 5H 5)F e(C O )(P P h 3)CH2O C10H 19 AND ( + ) 57 8 " (77'"C 5H 5)F e (C O )(P P h 3 )C H 2C O O C 10H 19 INTRODUCTIO N One of the m o s t im p ortan t a p p lica tio n s of CD (C ircu la r D ic h r o ism ) s p e c t r o s c o p y has b e e n in the a r e a o f o p tic a lly a ctiv e c oord in ation co m p o u n d s. S e v e r a l a b solu te co n fig u ra tio n a s s i g n m e n ts have b een p r o p o s e d on the b a s is of CD stu d ies, u sin g the a s su m p tio n that c l o s e l y r e la te d com p ou n ds of the s a m e a b so lu te / 7 con figu ration should exh ib it s im il a r CD c u r v e s . ’ In 1954, an X - r a y s tr u c tu r a l a n a ly s is o f the a b solu te co n fig u ra tio n of the (C o(en)g)^+ cation (en = eth y len e diam in e) w a s done by Saito and c o - Q w o r k e r s , and the r e s u lt w as found to a g r e e w ith that p r e d ic te d 9 10 f r o m CD stu d ie s. F u r th e r X - r a y stu d ies ’ h a v e c o n fir m e d two s tr u c tu r e s w h o se a b so lu te c o n fig u r a tio n s h ave b e e n p r o p o s e d on the b a s is of CD s tu d ie s . ^ B a s e d on th e s e o b s e r v a tio n s , it w a s co n clu d ed that CD in fo rm a tio n is a r e lia b le m e a s u r e o f the c e n tr a l 1 m e t a l con figu ration . S in ce that tim e , o v e r s ix ty a b so lu te c o n fig u r a tion al d e te r m in a tio n s o f tr a n s itio n m e t a l c o m p le x e s have b e e n V irtu a lly a ll of the e a r l i e r in v e s tig a tio n s w e r e on o c ta h e d r a l co o rd in a tio n c o m p le x e s w ith cr-bonding lig a n d s. T h e r e is s till v e r y little in fo rm a tio n on the a b so lu te co n fig u ra tio n s of m e ta l c o m p le x e s I h avin g o th e r g e o m e t r i e s and of c o m p le x e s w ith 7T -ligands (o rg a n o - m e t a llic co m p o u n d s). The p r e s e n t w ork, w h ich d e s c r ib e s the a b so lu te co n fig u ra tio n d e te r m in a tio n s of two p s e u d o -te tr a h e d r a lly co o r d in a te d iro n c o m p le x e s , w a s d e s ig n e d to r e c tify th is d e fic ie n c y , and to p ro v id e a m o r e s o lid foundation fo r CD - ab solu te c o n fig u r a tio n a l c o r r e la t io n s . c o m p le te d by X - r a y m e th o d s. ^ lb e th er (-)JW]578 = 375 2 0 1 IIa e s t e r <-> W 578 = 3 0 9 lib e s t e r (+){W] 5 7 8 = 330 The com p ou n ds d e s c r ib e d in this w o r k a r e ( + )* “( i T - C gH g)F e (C O )(P P h 3 )CH2 O C 1 0 H 19 1 3 >21 (la) and its e s t e r ( +)-(77~C5H 5)F e (C O )(P P hg)C H 2 COOC ^ (lib). B oth com p ou n d s w e r e p r e p a r e d and kind ly su pp lied to the w r ite r b y D r. T. C. F lo o d 's group of our d ep a rtm en t. (la) and (lb) w e r e p r e p a r e d by the alkylation of the p h o to c h e m ic a l in c o r p o r a tio n of trip h en y lp h o sp h in e. S ep aration of the d i a s t e r e o m e r s w as c a r r ie d out b y fr a c tio n a l c r y s ta lliz a tio n f r o m h ex a n e. (Ila) and (lib) w e r e p r e p a r e d b y the addition of (7/ -C g H g )F e (C O )2 N a to ( - ) - m e n th o l b r o m o a c e ta te , fo llo w ed by in co r p o r a tio n of trip h en y lp h o sp h in e under p h otolytic con d ition s. The CD s p e c tr a of (la) and (lib) (F ig. 1) a r e a p p r o x im a te ly m i r r o r * The d esig n a tio n ( +) o r (-) in th is w ork r e f e r s to the sig n of the ORD rotation at 578 nm . ( 7T~-CgHg)Fe(CO)2N a by c h lo r o m e th y lm e n th y l e th e r , fo llo w ed by 3 w a v e l e n g t h MOLECULAR EUPT1C1TY v 10' 4 im a g e s o f e a c h o th er in the re g io n 3 0 0 -3 5 0 n m , indicating that the c o n fig u ra tio n s a r e d ifferent. The ten ta tiv e a s s ig n m e n t o f a b so lu te co n fig u ra tio n s show n in (la) and (lib) w e r e m a d e b y c o m p a r is o n w ith the known co n fig u ra tio n of (+ )(R )* (f7~-C g H g )F e (C O )(P P h 0 ) + i / C ^ N H C H P h C H g J C H g B F ^ > , w h o s e a b so lu te s t e r e o c h e m i s t r y h as 1 7 b e e n d e te r m in e d by X - r a y c r y s ta llo g r a p h y . THE S T R U C T U R A L ANA LY SIS O F ( + ) 5 7 8 _{77' ' C 5H 5)F e (C O )(P P h 3 ) CH2O C 10H iq (la) C o lle c tio n and R eduction of X - r a y Data S u itab le c r y s t a ls o f the com pou nd, obtained via r e c r y s t a l l i z a tion f r o m an e t h e r /p e n ta n e s o lu tio n u n d e r an in ert a tm o s p h e r e , w e r e su p p lied by D avid M ile s o f P r o f. F lo o d 's group. A s p e c im e n of a p p r o x im a te d im e n s io n s 0. 3 2 m m x 0. 4 0 m m x 0. 5 6 m m w a s s e le c t e d for s tr u c tu r a l a n a ly s is . The c r y s t a l w as m ou n ted alon g the 101 axis in a t h in -w a lle d g la s s c a p illa r y of d ia m e te r 0. 5m m . P r o c e s s i o n p h otograp h ys in d ica te d a m o n o c lin ic unit c e l l show ing L au e s y m m e t r y 2 /m . The s y s t e m a t i c e x tin c tio n s o b s e r v e d (OkO = 2n + l), a r e c o n s is te n t w ith the m o n o c lin ic s p a c e group P2^ (No. 4). The unit c e l l p a r a m e t e r s , ob tain ed by c a r e f u lly m e a s u r in g the settin g a n g le s of * F o r p r o p o s e d seq u en cin g r u le s for the a p p lica tio n of the R - S d e sig n a tio n to o r g a n o m e ta llic c o m p le x e s , s e e r e f e r e n c e 18. 5 36 r e fle c tio n s on a N onius C A D -3 fu lly a u to m a ted X - r a y d if f r a c t o m e t e r , a r e giv e n to g e th e r w ith o th er r e le v a n t c r y s t a l data in T ab le 1. One h e m is p h e r e of data w as c o l le c t e d b y the 0 / 2 9 sca n techniq ue u sin g the Z ir c o n iu m - filte r e d M o rad iation up to a 20 lim it of 4 5 ° . A total of 4161 r e fle c tio n s (in cluding 70 ch eck r e fle c tio n s) w e r e c o l le c t e d in the fo llo w in g m a n n e r : (1 ) a sca n s p e e d o f 1 0 ° / m m w as u sed ; (2 ) the sc a n ran ge w a s d efined as 4 0 = 1 ,2 0. 15 tan; (3) b a ck g ro u n d counts w e r e taken at the b eginn ing and the end of e a c h scan (the tim e taken for counting ea ch b ack grou n d w as p r e c i s e l y one q u a rter of the t im e tak en for the sca n itself); (4) the n u m b e r o f s c a n s for e a c h r e fle c tio n v a r ie d b etw een two and eight, depending on the in te n sity o f the r eflectio n ; (5) N ic k e l fo il a tten u a to rs w e r e in s e r t e d a u to m a tic a lly b e tw e e n the d etecto r and c r y s t a l if the counting rate e x c e e d e d 2, 500 c o u n ts /s e c o n d ; and (6 ) a t a k e -o ff an gle of 4 ° w a s u s e d . T h r e e c h e c k r e f le c t io n s w e r e m o n ito r e d at 6 0 - r e f le c t io n in te r v a ls and sh o w e d no sig n ific a n t v a riation in in ten sity . The standard d eviation of e a c h in te n sity read in g, ct(F q ^), w a s e s tim a te d 2 . 2 1 / 2 u sin g the fo r m u la cr(F Q ) = (total count + 0. 04 (net in ten sity) ) R e fle c tio n s w h o se n et in te n s itie s w e r e l e s s than 3cr w e r e c o n s id e r e d u n o b s e r v e d and w e r e e lim in a te d f r o m the su b seq u en t s t r u c tu re a n a ly s is . An a b so rp tio n c o r r e c tio n w a s not a p p lied as the 6 T A B L E 1 C r y s ta l D ata for ( + ) 5 7 8 - ( 7 r - C 5 H 5)Fe(C O ) ( P P h 3 )CH2 O C 1 0 H 19 (la) a = 1 0 . 8 8 2 ( 3 ) 5 M ol. Wt. = 5 8 0 .0 b = 1 1 . 0 5 4 ( 4 ) 5 S p ace Group = P 2 j c = 13. 664(4)5. Z = 2 * = 9 0 . 0 0 ° D (exp)* = 1- 18 g / c m 3 % = 1 0 2 . 6 6 (2 )° D (calc) = 1' 2 0 8 g / c m 3 X = 90. 00 M = 5. 6 9 c m - ^ (for Mo K°< X - r a y s ) V = 1597. 9 5 3 * O b tain ed by flotation f r o m an aqu eous zinc iodide solu tion . 7 in te n sity of an a x ia l r e fle c tio n (at X - 9 0 ° ) sh o w ed e s s e n t ia ll y no v a ria tio n w ith . The in te n s itie s w e r e fu rth er c o r r e c t e d for L o r e n tz and p o la r iz a tio n e ffe c ts and p la c e d on an a p p r o x im a te ly a b so lu te s c a le b y m e a n s of a W ilso n plot. At the end of data r e d u c tion, 3655 r e fle c tio n s w ith I> 3 <r, r e p r e s e n t in g the hkl and hkl quadrants of data, w e r e r e ta in e d fo r the su b s e q u e n t s tr u c tu r e a n a ly s is . Solution and R e fin e m e n t of the S tru ctu re S c a tte r in g fa c to r s for F e , P , O, and C w e r e taken f r o m the "International T a b le s fo r X - r a y C r y s ta llo g r a p h y " and the e ffe c ts of a n o m a lo u s d is p e r s io n ( a f' and *if") for F e w e r e in clud ed in the final c a lc u la te d str u c tu r e fa c t o r s . A t h r e e - d im e n s io n a l P a t t e r s o n m a p w a s u s e d to obtain the c o o r d in a te s of F e and P a to m s . W ith t h e s e c o o r d in a te s a str u c tu r e fa c to r ca lc u la tio n and d iffe r e n c e F o u r ie r m a p r e v e a le d the p o s itio n s of c y c lo p e n ta d ie n y l, carb on yl, trip h en y l p h osp h in e, and m en th y l grou p s v e r y c l e a r ly . A ll o f the m e a s u r e d c o o r d in a te s w e r e then re fin e d b y a l e a s t - s q u a r e s p r o c e s s to an R fa c to r o f 8 . 5 p er cent. In th is r e fin e m e n t, a n is o tr o p ic t e m p e r a tu r e fa c t o r s w e r e a s s ig n e d to F e , P , and is o tr o p ic o n e s to the r e s t o f the a to m s . At th is point the a b so lu te co n fig u ra tio n of the c o m p le x w as in v e stig a te d . The str u c tu r e a n a ly s is had so fa r p r o c e e d e d with the a b so lu te co n fig u ra tio n c o r r e s p o n d in g to the one shown in (la). 8 C hanging the sig n s of the y c o o r d in a te s of a ll the a to m s h as the e ffe c t o f in v er tin g the m o le c u l e th rou gh a m i r r o r plane: in o th e r w o r d s , co n v e r tin g (la) to its m i r r o r im a g e . A re p e a t o f the l e a s t - s q u a r e s r e fin e m e n t w ith th is in v e r te d m o le c u le r e s u lt e d in an R fa c to r of 9 . 4 p er cen t, v e r y s ig n ific a n tly in fe r io r to the 8 . 5 p e r cen t o b tain ed e a r l i e r w ith co n fig u ra tio n (la). T h is d iffe r e n c e , a c c o r d in g 4 9 to H a m ilto n 's R fa cto r s ig n ific a n c e t e s t , in d ica tes that the p ro b a b ility o f (la) b ein g the c o r r e c t co n fig u ra tio n is w e ll o v e r 99. 99 p e r cent. R e s u m p tio n o f the l e a s t - s q u a r e s r e fin e m e n t w ith the o r ig in a l co n fig u ra tio n (la), now u sin g a n is o tr o p ic te m p e r a tu r e f a c to r s for a ll a to m s , r e s u lte d in the fin al a g r e e m e n t fa c to r s R = 6 . 2 p e r cen t and Rw = 7. 8 p e r cent. The a to m ic p o s itio n s f r o m the fin al l e a s t - s q u a r e s r e fin e m e n t w e r e u s e d to c a lc u la te the a n g le s and to illu s tr a te the m o le c u la r g e o m e t r y (F ig. 2 and F ig . 3). Stan d ard d ev ia tio n s w e r e c a lc u la te d for a ll a to m ic p o s itio n s , bond d is t a n c e s , and a n g le s . P o s it io n a l and th e r m a l p a r a m e t e r s alon g w ith th e ir a s s o c ia t e d stan d ard d ev ia tio n s a r e li s t e d in T ab le 2. The bond d ista n c e s and a n g les a r e p r e s e n t e d in T able 3, and c a lc u la te d and o b s e r v e d s tr u c tu r e fa c t o r s a r e li s t e d in T able 4, 9 Figure 2 The molecular geometry of (+)^oQ-(t-G^H^)Fe(C0)(PPh^)CH20G^QH^g{Ia), confirming the absolute configurational assignment derived from circular dichroiom studies. p The molecular geometry of la confirming the absolute configurational assignment on the menthol group. Note the all- equatorial disposition of groups around the cyclohexane ring. TABLE 2 F in a l A to m ic P a r a m e t e r s for (+ )g^0 -(T P -C gH g)F e(C O ) ( P P h 3 )C H 2O C 1 0 H 19 (la) A to m X Z z F e 0. 1225 1) 0. 00* 0.3416 1) P 0. 2661 2) 0. 1341 2) 0. 4022 2) O 1) 0. 9407 2) 0. 1087 9) 0.4380 7) O 2) 0. 9221 6) 0.0707 7) 0.1394 5) c 1) 0. 0146 9) 0. 0677 10) 0. 4016 8 ) c 2) 0. 0552 9) 0. 1018 ID 0.2200 8 ) c 3) 0. 8691 9) 0. 1286 10) 0. 0897 7) c 4) 0. 7551 11) 0. 0532 12) 0. 0373 8 ) c 5) 0.6924 11) 0. 1194 13) 0. 9374 8 ) c 6) 0.6543 12) 0. 2438 13) 0. 9537 9) c 7) 0.7645 12) 0.3201 13) 0. 0081 10) c 8 ) 0.8308 10) 0. 2582 ID 0. 1083 8 ) c 9) 0.2129 14) 0. 4195 14) 0.9727 11) c 10) 0.3299 15) 0.3380 17) 0.0076 15) c 11) 0. 1204 14) 0. 3987 15) 0. 0434 12) c 12) 0. 7300 16) 0. 4536 14) 0.0312 12) c 13) 0. 9659 12) 0. 3308 10) 0. 6753 11) * C o o rd in a te fix e d b y s y m m e t r y . TA BLE 2 (Continued) A to m X C (14) 0.9076 12) C (15) 0.7783 12) c (16) 0. 7563 12) c (17) 0. 8670 14) c (18) 0.2367 10) c (19) 0. 1197 11) C (20) 0. 0959 14) c (21) 0. 8131 19) c (22)' 0. 3048 13) c (23) 0.3299 12) c (24) 0. 3058 9) c (25) 0. 2848 13) c (26) 0.3083 15) c (27) 0. 3640 16) c (28) 0. 3915 17) c (29) 0. 3597 14) c (30) 0. 4189 9) c (31) 0.4168 10) c (32) 0.5304 11) c (33) 0. 6415 10) c (34) 0. 6426 10) c (35) 0.5272 10) £ z_ 0. 3514 11) 0. 7583 10) 0.3672 10) 0.7207 11) 0. 3519 12) 0. 6152 9) 0.3289 11) 0. 5878 10) 0. 2941 9) 0.3701 7) 0. 3450 12) 0. 3730 10) 0. 4672 12) 0. 3501 11) 0. 0:365 12) 0. 6779 11) 0. 4891 14) 0.3186 8) 0. 3683 11) 0. 3418 9) 0. 1441 10) 0.5389 7) 0. 0455 13) 0. 5938 9) 0. 0505 15) 0. 7014 9) 0. 1525 18) 0. 7488 9) 0. 2453 17) 0. 6940 11) 0. 2453 14) 0.5883 10) 0. 1102 10) 0.3684 8) 0. 1096 12) 0. 2667 8) 0. 0968 14) 0. 2350 9) 0.0832 12) 0. 3007 10) 0. 0805 13) 0. 4036 10) 0. 0950 11) 0. 4342 8) 13 TABLE 2 (Continued) A tom io4b 11 1q4(3 22 1q4/3 33 F e 54 1) 51 ( 1 ) 40 1 ) P 47 2) 52 ( 2) 41 1 ) 0 1 ) 95 8 ) 158 ( 1 1 ) 105 7) O 2) 54 6 ) 88 ( 7) 43 4) c 1) 68 1 0 ) 82 (1 0 ) 69 7) c 2) 47 9) 77 (H) 63 8 ) c 3) 61 9) 82 (1 0 ) 32 6 ) c 4) 63 10) 120 (12) 42 7) c 5) 91 13) 135 (15) 54 7) c 6 ) 95 13) 127 (15) 67 9) c 7) 88 13) 123 (14) 66 9) c 8 ) 88 11) 91 (12) 42 7) c 9) 102 15) 101 (15) 80 10) c 10) 137 18) 162 (21) 140 15) I0 4 9 l 2 lo 4B l 3 1 0 4 e 23 -1 ( 2 ) 27 ( 1) 5 2 ) 6 ( 4) 21 ( 3) 11 2 ) -15 (1 6 ) 134 (13) -69 15) - 1 2 (1 1 ) 20 ( 8 ) 18 9) -15 (17) 85 (14) -46 14) -4 (1 6 ) 13 (13) 14 15) 1 (17) 5 (1 2 ) 11 14) 7 (18) -9 (14) - 1 1 15) 22 (23) 8 (15) -7 18) 76 (24) 30 (17) 24 18) 65 (2 2 ) 15 (17) 26 18) 38 (18) 26 (14) 18 14) 22 (2 2 ) 41 (2 0 ) 29' 18) 125 (32) -23 (2 6 ) 57 29) TABLE 2 (Continued) A tom *°4s 11 1C)40 2 2 1()40 3 3 1q4|S12 1 ° 4 (3-1 3 1 0 V 23 C (11) 126 (1 6 ) 162 (18) 105 11) -32 (28) 91 (2 2 ) 67 (23) C (1 2 ) 22 6 (2 2 ) 97 (14) 95 1 2 ) 103 (28) 51 (26) 37 (20) C (13) 105 (13) 60 (1 1 ) 106 11) 36 (18) 44 (20) 19 (1 6 ) C (14) 123 (15) 72 (12) 72 9) -13 (21) 4 (18) 43 (16) C (15) 128 (15) 50 (10) 95 11) - 8 (19) 63 (20) 25 (16) C (1 6 ) 115 (14) 87 (12) 61 8 ) -28 (2 1 ) 3 (17) -13 (16) C (17) 150 (17) 67 (11) 71 9) 20 (2 2 ) 54 (21) -10 (16) C (18) 82 (1 1 ) 58 ( 9) 43 6) -10 (16) -2 (13) 7 (1 2 ) C (19) 116 (14) 75 (13) 81 9) 40 (20) 31 (17) -15 (17) C (20) 168 (17) 95 (17) 97 11) 82 (24) 23 (21) -16 (18) C (2 1 ) 261 (25) 61 (13) 83 11) -16 (30) - 8 (27) - 6 (17) C (22) 195 (17) 80 (1 2 ) 57 7) -55 (29) -13 (17) 42 (19) C (23) 140 (14) 89 (13) 54 7) -56 (22) 14 (17) 10 (15) C (24) 63 ( 9) 82 (1 1 ) 57 7) -9 (17) 35 (13) 7 (15) C (25) 152 (16) 143 (17) 63 9) -40 (25) 50 (19) 41 (18) TABLE 2 (Continued) A tom > « M 1 lO^ B 22 10^ iU (333 104£ l 2 10^ iU p 13 1 0 V 2 3 C (26) 206 (19) 183 (19) 44 ( 8) -154 (30) 10 (20) 12 (19) C (27) 175 (19) 202 (23) 35 ( 8) 9 (34) 25 (20) 23 (24) C (28) 238 (25) 145 (20) 60 (10) -33 (35) -12 (24) -83 (24) C (29) 181 (17) 115 (15) 66 ( 9) -75 (27) 12 (20) -20 (19) C (30) 44 ( 9) 75 (10) 63 ( 7) 7 (15) 44 (13) 22 (14) C (31) 88 (11) 116 (13) 61 ( 8) 3 (19) 60 (15) 8 (16) C (32) 85 (13) 156 (17) 83 ( 9) -35 (23) 81 (19) 8 (20) C (33) 56 (11) 147 (15) 88 (10) 7 (20) 57 (18) 41 (20) C (34) 71 (11) 161 (17) 73 ( 9) 14 (22) 30 (16) 32 (20) C (35) 73 (11) 106 (12) 68 ( 8) 20 (18) 40 (16) 28 (16) O '- TABLE 3 B ond D is t a n c e s and A n g le s in ( + ) 5 7 g - ( TT-CgHg) F e (C O )(P P h 3 )CH2O C 10H 19 (la) (A) B ond D is ta n c e s (in a n g s t r o m s ) I r o n -P h o s p h o r u s F e - P 2. 181 (2) Iron - C arbon F e - C (1) 1. 744 (8) F e - C (2) 2. 001 (8) 7T-C5H 5 : F e - C (13) F e - C (15) F e - C (17) 2. 093 (9) 2. 109 (9) 2. 115 (9) F e - C (14) F e - C (16) A vg. = 2. 1068. 2. 115 (10) 2. 105 ( 9) P h o s p h o r u s -C a r b o n P - C (18) P - C (30) 1. 835 (7) 1. 839 (7) O xygen- P - C (24) ■Carbon 1. 816 (8) O (1)-C (1) C ( 3 ) - 0 (2) 1. 127 (10) 1 .3 9 1 ( 8) C arb on- C (2) -O (2) •Carbon 1. 474 (9) M enthol: C (3)-C (4) C (5)-C (6) C (7 )-C (8) C (4)-C (9) C (9 )-C (l 1) 1. 535 (12) 1. 468 (15) 1. 558 (12) 1. 532 (14) 1. 526 (16) C (4)-C (5) C (6)-C (7) C (8) -C (3) C (9)-C (10) C (7)-C (12) A vg. = 1. 54.8. 1. 567 (12) 1. 520 (14) 1. 531 (12) 1. 534 (17) 1. 572 (15) 17 T A B L E 3 (Continued) IT- C 5H 5 : C (13)-C (14) C (1 5)-C (16) C (17)-C (13) 1 .4 3 3 (15) 1 .4 1 8 (14) 1 .4 2 3 (15) C (14) -C (15) C (16)-C (17) A vg. = 1. 41^1 1. 399 (15) 1. 362 (15) P h e n y l #1: C (1 8 )-C (19) C (20)-C (21) C (22) -C (23) 1. 407 (13) 1. 378 (19) 1. 391 (14) C (19)-C (20) C (21)-C (22) C (23)-C (18) 1. 397 (14) 1. 395 (20) 1 .4 1 9 (12) P h e n y l #2: C (24)-C (25) C (2 6 )-C (27) C (2 8 )-C (29) 1. 384 (13) 1. 379 (18) 1 .4 0 1 (16) C (2 5 )-C (26) C (27)-C (28) C (29)-C (24) 1 .4 2 4 (12) 1. 341 (18) 1. 369 (13) P h e n y l #3: C (3 0 )-C (31) C (3 2 )-C (33) C (3 4 )-C (35) 1. 390 (11) 1. 357 (13) 1 .4 1 9 (12) C (31 )-C (32) C (33)-C (34) C (35)-C (30) A vg. = 1. 39-S 1 .4 0 1 (13) 1. 396 (14) 1. 328 (11) (B) B ond A n g le s (in d e g r e e s ) P h o s p h o r u s - Ir o n -C a r b o n C ( l ) - F e - P 9 1 . 7 (3) C a r b o n -Ir o n C (2)- F e - P -C arb on 92. 0 (2) C ( l ) - F e - C (2) 89. 2 (4) I r o n -C a r b o n -O xygen F -C ( l) - O (1) 177. 4 (8) F e - C (2 )-O (2) 109. 6 (5) I r o n -P h o s p h o r u s -C a rb o n F e - P - C (18) F e - P - C (30) 1 1 9 .5 (3) 114. 7 (3) F e - P - C (24) 114. 9 (3) 18 n o n N H H H -> nQ vD I I I 0 o o To tv I-* N O C O 1 I I O O O . « ■ — * * # — ■ * « • co co to W H O ) tJ 3* C D 3 = t t = o o o | _ i H -* H— 1 o ^ ^ CJl w « » w HI 1 1 1 o a o CJl i— i | — i o - 0 U l w 1 I 1 o o o ^ipm! (■ <■ ! OO O ' o o o o o o o o I — iP 00 O' >P oo 4 \ •3 i i i i i i > o o o o n o » — « * « * - * S 1 N * "* > » * « — S ^ sD -O -O CJl i P OO 3 i i i i i T " • o n ci o o o P H H 00 O vD 00 L _ 4 O I S ) 'O -X > 00 ♦ * • H W \D H — 1 i — 1 -v ] O I — ’ — ' o o o 00 o o • • • 0s sO vD 3 s O N D o * — * O H - * ► — 1 I — ' H " 1 M O D O ,N N h • • • « • • • 0 s -»3 - 0 00 sO ■ v D CO 00 s O 00 00 - J - J O 0 o o N M H IN) O 00 1 I I 0 O O N CO h (jO H -1 V O 1 I I o o o T h To To 03 N O > O O < _ _ ^ O P i— * i — ■ C J l 00 II 1 1 I — 1 O O o 00 H 4 i — * * O ' P o ■ ---I * o 1 i O n ,_ _ . H * i — * -o C J l > < 3 O P 00 o O a O O O O P - o CJl CJl O O i o i O 1 O 1 O i O 1 o T o 3 Q 5 i i i i i o o o o o 1 O I — * H oo H CO T j vX 3 CJl v O CO t o IN) O I-1 o • • • 00 sO # ■ — > % * » — « N \ £ > h -1 sO -H O I — I I — * o o NO 0 0 • • 00 0 0 To vo I — 1 H > H -1 I — > H O W O W N Ul - J • • • « • • C J l 00 O O sO 00 O ' Q T o o o w C D 3 rt 3* o o S O tr 0 3 1 o S O 4 ( T 1 0 3 1 n p 4 o' o 3 CO I 0 00 1 o o 00 O' o CO I o 00 1 o 00 0 • < 3 J P C D 3 1 n S D o' 0 3 1 o p H o ' o 3 o to I o CO I n o o iP iP O' T) U U I I I o o o 00 C O i — * 0 P - 00 1 I I o o a o p 4 o ' 0 3 1 0 " < JP C D 3 1 o p o ' o 3 oo to H J (J 1 uv 05 • • 0 0 o 01 O ' v O v X ) p O' h d I I o o oo CO O P I I I O Q O oo To to U 1 vO 00 h d I o 00 * t) 3 ' o C D fa 3 * 0 hi 3 C D 1 o p > - s o' o 3 f o p •-i o' o 3 0 O CO t— P 00 1 I i i o a 0 0 CO O P o o O O o • • v O H - * P P o 00 I h d I o oo o o p hi o' 0 3 1 3* o C D O 3* 0 |-i 3 C D 1 o p O ' 0 3 O ' C O co to I p CO H • • • iP O' -J O ' T T J O ' p T p TABLE 3 (Continued) T A B L E 3 (Continued) P h e n y l #2: C (25)-C (24)-C (29) 1 1 8 . 4 ( 8 ) C (24)-C (25J-C (26) 1 2 1 . 0 ( 9 ) C (25)-C (26)-C (27) 1 1 8 . 9 ( 1 0 ) C (26)-C (27)-C (28) 1 1 9 . 3 ( 9 ) C (27)-C (2 8 )-C (29) 1 2 2 .4 (12) C (28)-C (29)-C (24) 1 1 9 . 7 ( 1 0 ) P h e n y l #3: C (31) -C (30) -C (35) 119. 8 (7) C (3 0 )-C (3 1 )-C (32) 1 1 9 .3 (7) C (31)-C (32)-C (33) 121. 6 (9) C (32)-C (33)-C (34) 118. 7 (8) C (33)-C (34)-C (35) 119. 0 (8) C (3 4 )-C (3 5 )-C (30) 121. 5 (8) A vg. = 120. 0 C 20 T A B L E 4 O b s e r v e d and C a lc u la te d S tru ctu re F a c t o r s for F e (C O ){ P P h 3 )C H 2O C 10H 19 (la) The c o lu m n s d isp la y e d a re: h, 10 x F ^ g S 10 x F caj c , a n d the p h a se an gle. F o r e x a m p le , the f i r s t e n tr y sh ow s that, for the 2 -11 O r e fle c tio n , F ^ g = 1 8 .9 , F c a i c = 1 7 .8 , and *> = 88°. 5 • 1 \ 1 10 98’-118 'M ' —1 1 . 0 . W - i • ’ - 0 2 t 09 1 78 88 3 203 1 94 86 3 132 132 -14 2 4 * !- too 80 - 1 4 H « ■ » 10 0 6' 316 30 8 -101 . 7 325 297 -1 09 0 • 92 76 -78 8 283 277 6 1 1 79 69 8 . 9 - : 109 09 124 2 140 134 26 10 169 161 89 3 145 1 36 -179 1 1 80. 84 97 4 1S5 M B -> 1 6 4 5 7 ft 54 1 76 H 0 , o H -9 0 \ 3 • 329 229 -3 4 416 350 -177 i IPO 104 59 5 590 54 8 -1 70 2 225 223 1 32 ft 274 238 -1 79 3 1 63 157 67 7 94 8 1 ft 4 145 132 -22 8 299 295 2 5 76 79 -75 9 1 29 14| 4 6 135 1 2 1 -125 10 7 1 8S 1 70 T 1 40 1 4 0 -94 1 1 6ft 57 -1 74 H — 8 0 M I 0 0 450 434 ?7 3 1 ?3 ! 1 1 -46 1 46 67 50 4 102 8 3 - 1 66 2 227 221 1 18. 5 45 44 8 1 3 102 1 02 168 6 312 .316 -72 4 734 239 - 155 7 329 305 -66 5 ' 1 87 1 82 -171 8 265 ?75 1 1 7 7 1 86 1 70 -21 9 82 91 63 8 1 25 121 0 10 1 69 163 90 1 1 70 ft 4 93 M -7 '0 H 2 ft i 4?? a 06 1 0 1 ? 260 2 * * ? O ft 2 33? 310 73 3 46 * 5! 7 ft 7 45? 44 5 1 1 9 a 67 T ? 1 f t « ?m 1 99 1 56 5 1 1* 1 24 1 44 5 4 24 39R -1 ftft 6 1 77 1 .1 1 -108 6 1 25 1 32 -1 .3 .3 7 351 254 -65 7 I 76 1 79 36 8 1 13 1 05 - 1 4 1 R 1 50 1 4 0 -T 9 10? 1 O P Oft 9 223 2? ? to 75 8 1 -45 M ' -6 o 1 1 07 nq 1 ?? 0 287 28? 5 1 H 3 0 1 351 322 -9 2 I 83 199 - 1 69 1 1 27 1 33 -101 3 223 205 1 74 r > 300 ?ft 7 96 4 22? 1 99 187 3 4 08 4ft t ft? 5 ? 86 283 -158 4 78 6ft 0 1 6 1 32 117 -114 f t 450 449 -85 7 238 237 29 6 7 70 323 - 7? 8 20? 200 4 8 20 1 2 1 4 -1 59 9 1 48 1 46 -30 9 101 1ft? 55 I 0 20 1 199 1 ftft M -5 0 I 1 1 4 3 1 TO 80 1 157 3 0 .1 123 H 4 0 2 535 462 68 3 4?5 4 00 77 1 266 ?57 4R . 4 70 73 1 26 2 o 1 87 1 ft! 5 300 ?0ft -80 3 ?86 272 1 *9 6 232 226 -67 4 405 415 1 7 1 7 7ft 62 ■ -69 6 1 60 ! 62 -13 ,e 155 141 -.10? 7 1 02 104 -40 9 1?4 11 ® 1 02 8 139 I 4 3 1 1 10 135 1 1 1 t f o 150 1 5” 1 ft . to 97 70 -40 M -4 0 H 5 f t 1 254 238 -44 2 86 86 -101 1 34 4 290 60 3 293 277 - 1 ftR 2 542 475 t 15 4 4?| 421 - 1 ft 7 3 4?4 4 1 5 t 05 6 160 161 1 2 4 65 72 54 7 1 1 9 1 1 8 64 5 298 278 -95 8 1 40 1 40 -t 6 209 217 -1 05 9 1 6? 146 -9 f t 154 143 -7ft 10 7 ft 82 49 9 105 137 P 3 1 0 144 145 1 30 H -3 0 H 6 0 1 127 130 -89 2 29? 296 90 1 352 ' 326 1 3 3 418 410 1 1 1 2 185 199 I 68 4 76 60 100 3 2 1 9 208 — 1 6 6 8 464 44 0 -91 4 229 21 4 -1 46 6 336 315 -101 5 274 276 162 n . 210 217 -27 6 137 1 35 1 1 4 9 1 19 111 130 -7 225 229 -26 10 206 1 93’ 77 8 196 1 99 1 1 1 I 4 4 1 4 1 98 9 153 1 55 36 M — 2 * 0 » 7 0 2 328 3 1 8 -73 t 41? 403 8 1 3 472 467 -118 2 254 250 90 4 219 215 -148 - 3 53 60 1 24 5 433 390 164 4 80 75 169 6 135 130 1 34 ' 5 i 1 9 130 30 7 174 169 -31 8 138 143 — 6 1 8 172 154 IT T - 240 247 - n o 9 244 238 57 8 HO 107 -37 to at *84 47 9 92 ro? ' 89 ■ M '. 8 , 0 • H ; -6 4 - ' * 2 P?2 220 -110 ■ -9 48 62 '': 23 2 222 220 -1 1 8 -0 143 153 1 63 3 1 06 107 -150 -7 242 239 -164 4 ' 223 229 161 -6 176 1 7 3 147 5 I 74 1 8 1 170 -5 163 168 • 66 7, 172 I 76 2 5' -4 221 218 6 8 131 1 22 9 - 3 370 38 t -1 -? ‘ 406. : 473 ‘ -t? H 9 i o' - 1 192 181 20 0 3S B 315 -162 ' 1 I?1 114 1 28 1 6 8 3 650 - 1 75 2 209 2 ft? 53 2 177 170 15? 3 161 1 59 99 4 Ml 1 3 S . . -65 4 135 1 33 -1 57 5 274 274 -16 0 79 77 — 93 6 276 P7R 36 6 136 1 35 -4 7 7 7 t 7 9 04 7 118 142 -70 8 98 9 * -96 9 146 146 15S H 1 0 f t H -a I 1 07 6 B 5 * 2 1 3 ft 1 7 4 »-25 ‘ -10 53 7 9 * - 71 3 140 137 -174 — 9 181 PT 79 4 1 4? 1 44 1 73 -0 105 1 It? 1 2 ft . 5 . 0 0 • 57 -150 -7 1 nP J 09 1 rip — 6 1 i f t i i i 2 0 H ! 1 0 -5 331 316 -ft? — A ?8 8 Iftft -70 2 1 87 iao • 90 — 3 I 55 I 5? 8 ? 3 1 91 195 97 -2 1 38 1 55 ' 30 -1 318 ?ei 70 H 1 1 1 0 J?9 7 . ? 3 7 -73 1 432 3 7? 6 6 -4 1 « 2 1 77 -89 ? I 95 166 -40 — 3 8 f t 5ft 9? 3 4 09 464 -101 — 2 1 92 1 P5 95 4 3 38 31 1 — 94 -1 73 89 97 ft 1 96 1 ftft 1 ?S ft 13? 177 6-5 7 1 9ft 1 ft1 ' 147 1 1 1 5 1 03 I 1 1 fi 1 76 163 07 3 M l I 04 - 7 0 P 50 ▼ 1 4 131 1 ? .7 — 73 M ' -ft 1 H — 1 f t 1 -10 76 7 1 -7ft -6 . , 1 1 1 104 -146 - 0 ? ft 7 1 Oft -1 7.7 -5 ' 79 R8 — 1 ? 9 -7 97 J? 1 70 - 4 . Q? esc, p -6 ?96 ? 4 4 -1 7 R -3 183 102 -8 -5 197 1 "3 1 6 8 - I •5ft 4 a -1 ? -4 ?OT ?.R6 1 6 1 1 ?5 1 19 161 — 7 4 7 A a > 6 - 1 P 1 7 ft 1 ! 9 - 1 7ft -? ? 5? 267 -o a 75 ?3 -1 3 2ft ft 1 6« 5 1 0 1 90 1 4 ft •* TC pft’ 70 6 fc ft 87 -36 1 !*A 1 08 1 8 f t 2 467 4 16 1 80 M -9 1 3 4 3 54 -137 4 367 74” -1 9 -7 7 1 7* -16 5 ’ 64 364 1 6 -6 l * 2 1 ft" - 1 1 4 6 0ft ? J 06 40 - 5 1 ft” 1 7? - J *8 8 9 0 > 0 6 1 -4 1 08 1 87 -63 « ?.73 273 1 76 - i 67 f 1 - 1 1 6 1 f t 1 ?7 1 ’ ft 1 54 -? 1 0 5 1 1 8 1 4 ft -1 i e i 1 07 3ft M - 1 1 0 1 P A 1 8 2 1 1 5 1 1G! 1 63 - 1 78 - | 1 7? 3 6 - 3ft 2 67 63 -9? - in 1 4? 1 16 1 ” 9 T 1 7 ft 1 93 - ftft -o 2?6 274 1 1 4 4 1 28 1 19 -lift -R ! 63 1 50 1 9 5 54 31 -1 57 -7 1 4 | 1 4 6 -1 74 f t 8? 77 38 -6 3 4 6 3?5 1 89 7 1 83 1 0 0 67 -5 ? 2 1 ??5 -60 -4 664 500 -00 H — 8 1 — 3 55 6f t R O -2 564 870 48 -0 • 7 ft 09 - 1 7 4 - 1 ? 32 1 76 -144 -7 208 1 8 1 1 77 1 ?? 8 ?S O 1 1 7 -5 101 IC O -25 2 533 . 490 -26 -4 1 4? I 4 R 66 3 6 1 9 540 -41 - 3 1 R 7 1 9? 65 4 467 42ft -13? -2 >48 2 39 -14 5 230 209 -16? - 1 ?46 2 43 ft 6 158 114 40 0 236 ? 3 ft — t 65 7 l3o 126 00 1 307 294 -157 8 29« 257 1 1 7 2 149 1 63 -06 9 101 101 05 4 9 1 9 ft 164 1 0 Iftft 86 -134 5 ' 1 30 1 23 — 4 6 299 294 - ? H -P. 1 7 76 79 1 ft 0 B 2 7? - 1 40 -11 170 1 6? 43 -10 134 120 -1 H -7 1 -o 0? ?9 -166 -8 21? ?27 -93 -9 1 49 I 49 7 1 *-7 22H ? 1 7 1 70 -R 2 O B 214 97 — 6 378 358 -171 — 6 294 298 -83 -5 P O P 1 94 -141 -5 1 55 1 63 -45 -4 495 437 7 1 -3 225 237 -89 -3 623 559 49 -2 67 65 -70 . -2 26 1 245 17 — 1 444 425 98 2 5 1 7 511 -145 0 70S 319 130 3 260 265 -IT S ' ~3 209 ' 2t6 -1 23 4 383 358 2 3 181 1 73 -73 , - 5 ~ . - J44ft 420 19 . 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M i '• -2 1 81 1 92 64 0 96 70 -121 -2 21 I 197 -6 6 -1 281 226 69 -7 75 98 -54 1 154 l A n 7 . 0 188 1 69 98 H ft 2 "-6 . 74 73 -69 ft 82 53 1 77 -6 56 62 21 1 97 90 95 -5 • J 03 97 -13 1 176 1 50 -7 8 . -3 1 27 127 39 H .3 1 -S 1 22 1 16 1 65 -4 49 4 9 -79 3 to t 1 19 -93 -1 1 36 171 -1 04 H -2 12 -4 93 1 02 1 50 -3 105 9 3 157 3 88 104 -43 ' 0 208 1 94 -9 5 -8 169 1 79 -109 -2 109 106 10 -2 1 0ft 1 7ft 7fi 4 72 95 -133 1 I 1 7 101 -57 -7 53 44 -98 -8 76 00 -2 ! - i 147 13| 41 •• -1 1 1 0 1 1 2 1 04 5 73 81 1 70 -6 65 60 70 -7 57 16 -53 0 155 1 46 -ft' 1 7 7 79 -90 6 87 89 73 H -4 1 -5 133 1 30 1 31 -6 94 97 1 77 1 89 01 -57 r 1 32 -4 147 1 47 1.34 -8 204 . .1.9! 156 H 4 1 3 H 4 10 -7 132 10 _ T 98 91 1 14 -4 150 1 45 15! H - 5 3 -6 132 139 45 -2 74 P5 179 - 3 46 4 0 170 -4 61 70 1 1 -0 248 248 175 1 06 102 14 -1 142 141 -93 -2 1 S O 1 34 38 -4 75 50 - 1 59 -3 I 09 1 76 1 2 -7 143 1 49 1 76 -7 134 1 35 1 77 0 1 95 1 85 -81 -1 1 70 1 69 20 -2 221 199 63 -2 71 70 - P . -6 100 101 68 -2 219 21 2 -171 0 132 1 ? 4 -21 - 1 141 I 22 1 06 -1 1 04 1 O S -1 71 -5 1 18 124 -5 - 1 109 1 1 5 1 76 H 4 1 1 80 01 -65 0 1 4 ft 1 40 1 76 — 3 226 216 36 1 224 20 6 - 1 H -4 3 1 09 95 171 — 2 1 84 1 42 19 -7 1 34 1 29 -3 w “ V 12 — | 1 12 08 -176 H — 3 1 -6 1 30 1 25 -38 -ft 60 20 -140 M 5 1 3 172 1 66 1 56 — S 60 41 94 -0 58 / 69 162 -163 -5 40 34 70 1 265 210 171 -8 1 86 1 07 -65 -4 1 18 10.3 -15 -7 1 56 99 -4 66 69 3 -4 «0 6 3 - 1 9 . 70 85 -66 -7 59 40 -66 -7 126 1 36 -170 -6 92 86 1 1? -3 10! 1 73 -7 -2 2 7 1 207 1 2 0 * 4 81 86 -41 -6 73 69 1 1 — 2 .2 14 210 1 77 -4 IS! 147 -124 -2 96 7! 3 -1 1 ?? 1 t 9 81| 5 1 2 1 1 20 12 -5 125 127 54 - I 1 24 1 1 7 — 1 60 — 3 1 53 1 54 -72 -1 1 16 105 1 75 0 S O ?9 is; -4 1 58 132 52 1 232 207 8 -2 183 1 6« -42 0 154 142 -1 69 ; . M •5 ‘ to -3 -2 75 82 P6 87 74 0 H 5 1 - t 0 61 106 32 1 1 1 -90 53 1 04 90 -161 H -3 *A | -8 107 1 08 120 -1 156 1 4 4 -79 1 145 12! 91 M - 3 3 -4 93 104 1 is -6 214 216 -86 n 1 94 183 -0 1 -7 8! 97 -1 19 -3 129 1 1 ? 1 35 -5 55 64 — t 58 - — 6 52 65 1 50 H 0 12 -6 84 68 - 97 — 2 00 - 50 -52 -4 85 77 -59 H -2 1 -5 64 46 96 — 5 67 60 — 1 63 -1 165 1 ft? - 70 -3 87 75 -18 -4 72 79 1 38 -5 306 396 -177 -3 91 05 24 1*' -2 224 212 1 30 -9 1 1 1 1 4 - I 42 -3 1 4? 1 38 143 -4 222 2 1 8 - | 77 . -2 197 1 07 1 09 M - ? -1 1 92 1 99 89 - e 71 08 75 -1 I 32 1 3 5 -69 -3 56 7 3 -1 -1 1 26 109 84 0 <>r 95 53 - 7 1 47 1 26 -9 0 1 96 1 97 -70 0 168 1 54 3 1 7? 78 -94 -5 64 60 39 2 05 1 05 -81 — 6 134 1 32 -7 1 99 95 -1 15 1 1 66 151 1 9 14 -4 103 73 143 3 ' no 65 -75 -5 1 1 7 108 - 32 h'3 2 H - ? -3 1 ? 1 0 7 -1 79 4 151 1 34 -80 -4 -3 21 1 74 203 73 131 -1 78 M ft 1 1 -7 98 7? -177 -2 -1 14? 90 121 Pft -1 46 1 45 M 6 0 -2 189 1 89 - I 06 -6 1 70 1 84 -4 -8 53 56 -1 9 -6 75 69 -4 1 0 70 58 79 - 1 166 I 74 -1 57 -5 90 90 — 4 ? -7 1 70 1 60 88 -5 79 69 — 58 I -7 83 66 -1 49 0 89 7 1 1 20 1 16 1 26 1 68 -6 89 01 70 -4 67 70 ?ft ' H -1 14 -6 141 1 38 155 1 1 60 147 0 - A 1 66 1 59 -177 -4 163 1 55 -51 -3 182 1 67 44 1 -4 155 ! 56 ' -9 - I 1 - ftft • no -143 -3 1 58 1 4 0 -99 -2 S? 31 45 -5 ,6 6 91 ni! — 3 1 20 1 25 42 H - 1 t -2 171 155 - 1 3? -1 56 60 -1 33 -4 90 10S| -2 77 69 105 H 7 1 0 1 ?O .J I 19 131 0 141 1 28 -161 -3 07 70 1 7ft| 0 141 1 34 - 162 -8 96 97 • -21 1 137 1 22 9ft 1 153 1 38 1 69 -1 «6 05 -6 7 1 215 1 96 -164 -7 ! 32 t 1 8 -95 -5- . 56 63 91 ' 0 1 07 1 1 1 -e?' 2 89 97 123 -5 242 258 75 -4 i. 1 43 1 40 91 H ? ? H -1 13 ! 09 54 - 0 5 3 52 10 -8* -4 317 301 91 -3 67 60 80 . | 4 1 65 1 60 — 2 - 3 1 82 1 76 1 07 -2 88 06 -4 4 -3 67 95 29 — 6 1 30 ! 45 -09 H 0 i* -1 1 33 133 -53 -1 * 109 1 1 1 — 57 -7 62 1 7 54 -5 - 1 06 1 -97 H 7 0 0 1 55 1 44 -5 8 0 73 64 -09 — 6 89 99 -1 60 -4 79 78 -5ft -ft Iftl 1 64 3 1 142 133 -91 1 1 1 50 1 44 -1 00 — 5 203 2 00 -151 -3 79 ' 03 01 -5 76 4 8 s : -6 117 1 00 -72 \ -4 ‘ 159. 1 54 -146 -2 138 I 1ft 1 4t -4 81, 7? -1 70 -5 2 t 3 209 -1 08 H 0 - 1 M : 1 -6 1? -2 1 1 5 1 36 -33 -! 143 1 30 1 02 -3 1 ?? 1 1 ft -1 75 •4 98 1 I 2 -92 -1 1 73 1 62 -13 0 93 I 1 0 74 -1 1 ?ft 1 50 -1 70 -3 1 16 1 33 100 -8 65 67 178 - 5 >136 1 2? - ! 5ft 0 1 1 27 1 .3! 78 2 149 1 24 -1 13 0 1 4 94 1 78 -2 1 80 1 86 86 — 7 7 6* 49 0 -4 i 1 15 1 09 - 1 44 1 69 04 66 1 1 ft? 1*2 3 ; - I 131 1 38 77 -6 107 1 16 6 — 3 ' 50 5 3 61 H 0 3 1 74 70 34 — 5 271 250 1 -2 1 23 1 05 -4 H 3 1 2 H 1 14 ! 2 82 80 — 81 -4 1 4 1 126 -1 79 -1 1 37 1 29 -34 -7 80 72 -1 73 1 3 t 39 1 47 -94 -3 243 2 35 -1 77 0 ; 1 60 1 48 2 -0 120 1 in 53 — 6 67 70 -1 77 -5 «1 O 7 1 07 -2 44 50 -1 67 1 1 07 83 58 -7 93 100 1 3 -5 93 1 1 1 2 -4 94 • 95 86 M 6 10 - 1 ' 1 32 t 30 -1 76 -6 77 81 40 -4 P . 3 ! 94 2 — 3 7 7 61 4 0 1 13 112 1 79 H — 5 2 — 5 1 20 1 1 5 -5 -3 10? 02 6 • -1 81 79 -107] - 4 1 52 159 0 t 208 213 2 -3 1 39 1 38 - h r -1 90 05 -177 0 1 2? 1 10 -AS -3 55 30 -21 — 6 12! 121 1 1 -2 20 1 1 90 -1 09 0 92 IOI -174 1 61 5* — 0 * 1 0 85 74 176 H 1 11 -4 56 63 -55 0 20 0 167 05 1 97 97 -17* 1 1 33 1 1 5 -170 -9 S7 54 -lot -3 -2 1 05 1 77 t 03 t 65 - l i t -1 22 1 1 1 1 90 97 H 1 13 H 2 1 4; H -7 1 — 8 87 78 -153 - t 58 49 -95 H 4 1 2 -4 07 7ft -1 40 * -7 124 1 20 -79 0 i 10 36 53 76 1 39 1 46 -03 -3 I 1ft i o n -171 -S 54 65 , 101 -5 261 263 1 08 1 1 38 1 22 97 -6 1 i 3 108 - 1 73 • 5 1 90 1 93 -77 — 2 1 ? 7 1 1 3 153 -4 153 1 40 96 -4 322 301 93 — 5 5 9 57 - i l l -4 93 75 — 119 -1 1 06 92 -1 40 -3 56 61 102 -7 1R5 1 7 ? 77 H -4 2 -4 48 45 - I 1 7 -3 70 85 104 0 5 ft'- 54 -70 •2 89 86 -134 -I 1 33 1 2.7 -1 1 9 — 3 82 79 -136 -2 103 1 02 45 / 1 - 126 1 03 -119 0 1 47 1 33 -112 — 6 1 1 ? 1 07 -1 70 -2 ! 30 1.33 -9 -1 1 2=1 1 ?8 05- M '1 14 0 84 66 -74 1 1 37 1 34 -82 -5 60 33 12.1 -1 i 217 208 5 0 100 1 13 1 09 - 1 l 154 146 -74 H 2 1 1 -3 -2 81 i 45 76 1 36 137 14 0 . 1 74 58 9 2 1 55 132 -60 -4 -3 1 04 t 19 98 1 O ft . 7 ? ■ 40 M -6 1 1 -9 109 108 147 - 1 0 226 85 ’ 204 57 -9 7 H 5 1 2 M ’ 2 1 3 -? -1 7 7 . 173 47 160 - 1 2 a ' — 96- -6 177 186 1 0 -8 07 31 -74 -6 I 13 117 75 -7 75 73 -169 '1 -5 85 98 47 -7 152 1 30 1 7 M — 3 1 2 - -5 46 6 -109 -5 7? 77 6? 1 , i ' I ( 2 8 : THE S T R U C T U R A L A N A L Y SIS O F <+ > 567-( ? r - C 5H 5)F e (C O )(P P h 3> C H 2C O O C 10H 19 (H b f C o lle c tio n and R ed u ction of X - r a y D ata C r y s t a ls o f '(lib) w e r e grow n by s lo w r e c r y s t a l li z a t io n f r o m d ic h lo r o m e th a n e u n d e r an in e r t a tm o s p h e r e . A S h len ck f la s k c o n tain ing a s m a ll v o lu m e o f a c o n c e n tr a te d s o lu tio n of (lib) w a s p la c e d in a r e fr ig e r a to r . The v o lu m e of s o lv e n t w a s d e c r e a s e d s lo w ly by p e r io d ic a lly flu sh in g the fla s k w ith dry n itr o g e n . M o s t of th e s e e ffo r ts , h o w e v e r , p r o d u c e d tw in n ed c r y s t a ls . It w a s found that c r y s t a l qu ality co u ld be im p r o v e d b y ex ten d in g the t im e in te r v a l b e tw e e n flu s h e s to one o r tw o w e e k s . A fte r in n u m e r a b le a ttem p ts spanning a p e r io d of s e v e r a l m o n th s , su ita b le c r y s t a l s fin a lly w e r e obtained. A c h e c k of o p tic a l rotation of t h e s e c r y s t a l sh o w ed that the o p tic a l p u rity of the m a t e r i a l h ad not d e te r io r a te d during this t im e . A s p e c im e n o f a p p r o x im a te d im e n s io n s 0. 4 0 m m x 0. 5 6 m m x 0 . 6 5 m m w as s e l e c t e d for s tr u c tu r a l a n a ly s is . The c r y s t a l w as m ou n te d along the 013 a x is in a t h in - w a lle d g la s s c a p illa r y of d ia m e te r 0. 7 m m . P r e c e s s i o n p h o to g ra p h s in d ica te d a tr ic lin ic s y s t e m . B e c a u s e o f the o p tic a l a c tiv ity o f the com p ou n d, the on ly p o s s ib le S p ace grou p is P I (No. 1): The unit c e l l p a r a m e t e r s , t o g e th e r w ith o th er r e le v a n t c r y s t a l data, a r e p r e s e n t e d in T ab le 5. 29 T A B L E 5 C r y s t a l D ata for (■*-)5 7 8 -(-lT -C 5H 5)Fe(C O ) ( P P h 3 )CH 2 -C O O C 10H 19 (lib) a = 7. 6596 (6) A M ol. Wt. = 608. 0 b = 13. 8060 (12) A S p a ce group = P I c = 15. 9478 (11) A Z = 2 . 108. 234 (5)° D (exp)* - 1. 199 g/crn^ ? = 88. 625 (4)° D (ca lc) = 1 .2 1 6 g /c m ^ S’ = 9 5. 064 (4)° M - 5 . 8 1 c m "''(for MoK°< X - r a y s ) V = 1581. 4 A 3 * O b tained b y flotation f r o m an aq u eou s zinc iod ide so lu tio n . 30 A h a lf - s p h e r e o f data w a s c o l l e c t e d by the 0 /2 0 sca n t e c h nique u s in g z ir c o n iu m - f ilt e r e d Mo radiation up to a 20 lim it of 4 5 ° . A lto g e th e r 4266 r e fle c tio n s (including 74 c h e c k r e fle c tio n s ) w e r e c o l le c t e d in the s a m e m a n n e r as d e s c r ib e d e a r l i e r (P a g e 6). At the en d o f data red u ction , 3665 n o n - z e r o r e fle c tio n s w e r e left. Solution and R e fin e m e n t of the S tr u c tu r e S p a ce group PI w ith Z = 2 r e q u ir e s two indep en dent m o l e c u l e s in the unit c e ll. A t h r e e - d i m e n s i o n a l P a t t e r s o n m a p w as u s e d to obtain the c o o r d in a te s o f the F e and P a to m s . T h is w as fo llo w e d by a s e r i e s o f s tr u c tu r e fa c to r c a lc u la tio n s and d iffe r e n c e F o u r i e r s , w h ich r e v e a le d the p o s itio n s o f the c y c lo p e n ta d ie n e and tr ip h e n y l - p h osp h in e g ro u p s of both m o l e c u l e s . The c a r b o n y l and m e n th o l g ro u p s, h o w e v e r , r e m a in e d ill-d e fin e d . The r e a s o n for th is w as r e a d ily apparent: the two s e p a r a t e fr a g m e n ts (Cp-HgJFetPPh^) lo c a te d up to that point w e r e r e la te d b y a p seudo c e n te r of s y m m e t r y , and h e n c e e v e r y d iffe r e n c e F o u r ie r p h a se d b y th o s e a to m s a ls o h ad th is f a ls e in v e r s io n c e n te r . It w a s c le a r , then, that the p s e u d o - s y m m e t r y e le m e n t had to b e r e m o v e d b e fo r e the str u c tu r e c o u ld b e s o lv e d . C o n seq u en tly , a s in g le c a r b o n y l grou p on one of the m o l e c u l e s w a s added to the l i s t of known a to m s: th is d is tu r b e d the p s e u d o - s y m m e t r y s u ffic ie n tly to r e v e a l the p o sitio n of a few ad d ition al a to m s . R e p e a te d c y c lin g throu gh this p r o c e d u r e ( s t r u c tu re fa c to r ca lc u la tio n -f~ d iffe r e n c e F o u r ie r ca lcu la tio n ), e a c h tim e 31 adding two o r t h r e e m o r e a to m s , r e s u lt e d in a g ra d u a l im p r o v e m e n t o f the a to m ic l i s t and a ste a d y d e te r io r a tio n of the f a ls e s y m m e t r y e le m e n t. E v en tu a lly , a fte r e le v e n su ch s te p s, the e n tir e m o le c u l a r str u c tu r e w a s known. The a b so lu te co n fig u ra tio n o f the m o le c u l e (lib) w as d e te r m in e d b y u sin g the m e n th o l group, w h o s e a b so lu te c o n fig u ra tio n w as c o n fir m e d in the e a r l i e r s tr u c tu r e d e te r m in a tio n of (la), as a r e f e r e n c e . A m olecular plot of the t r ia l s tr u c tu r e at th is sta g e sh o w ed the a b s o lute co n fig u ra tio n o f the m e n th o l group to be o p p o site to that found in (la), th e r e b y in d icatin g that the c o o r d in a te s u s e d w e r e in fact r e v e r s e d . C hanging the s ig n s o f a ll c o o r d in a te s now gave the c o r r e c t c o n fig u ra tio n . The s tr u c tu r e a n a ly s is w a s c o n c lu d e d w ith s e v e r a l c y c l e s of l e a s t - s q u a r e s r e fin e m e n t, in w h ich the p h en y l a to m s w e r e r e fin e d I is o t r o p ic a lly and the o th er a to m s a n is o tr o p ic a lly . F in a l R fa c to r s a r e R. = 8 . 4 p er c en t and R w = 10. 2 p e r cen t. P o s it io n a l and t h e r m a l p a r a m e t e r s alon g w ith th e ir a s s o c i a t e d stan d ard d ev ia tio n s a r e li s t e d in T a b le 6. B on d d is ta n c e s and a n g le s a r e p r e s e n t e d in T able 7. C a lc u la te d and o b s e r v e d s tr u c tu r e fa c t o r s a r e lis t e d in T ab le 8. The m o le c u l a r s tr u c tu r e is show n in F ig u r e 4. D is c u s s i o n The u s e o f o p tic a lly a c tiv e tr a n s itio n m e t a l c o m p le x e s h as m a d e it p o s s i b l e to fo llo w the s t e r e o - c h e m i c a l c o u r s e of s e v e r a l 32 T A B L E 6 F inal A tom ic C oordinates for ( TT-C^Hi^FefCOHPPh^CH ^CO OCjQH^ A tom X m o le c u le #1 X ' z X m o le c u le #2 X z Fe 0 .0 (0) 0. 0 (0) 0. 0 (0) 0. 5642 (2) 0. 0865 (1) 0. 3837 (1) P -0. 1484 (4) -0. 1098 (2) -0. 1109 (2) 0. 7283 (4) 0. 1984 (2) 0 .4 8 6 2 (2) O (1) -0. 3121 (13) 0. 0770 (8) 0. 0893 (6) 0 .4 8 9 8 (2) -0. 0422 (7) 0.4 9 1 9 (6) O (2) 0. 1318 (15) 0. 2637 (8) 0. 0415 (9) 0. 6976 (13) -0. 1467 (7) 0. 2245 (6) O (3) -0. 1376 (13) 0. 2381 (7) 0. 0194 (7) 0. 8439 (11) -0. 1210 (6) t . 0. 3499 (5) C (1) -0. 1819 (15) 0. 0470 (9) 0. 0509 (7) 0. 5275 (16) 0. 0045 (9) 0 .4 4 6 4 (8) C (2) 0. 0415 (17) 0. 1050 (9) -0. 0715 (9) 0.7861 (15) 0. 0269 (9) 0. 3123 (8) C (3) 0. 0225 (16) 0. 2072 (11) -0. 0092 (10) 0. 7698 (16) -0. 0876 (9) 0. 2901 (7) C (4) -0. 1753 (22) 0. 3403 (11) 0. 0380 (11) 0. 8250 (19) -0. 2290 (9) 0. 3401 (9) C (5) -0. 3166 (24) 0. 3227 (12) 0. 1028 (12) 0. 7175 (23) -0. 2400 (11) 0 .4 1 9 0 (10) C (6) -0. 3815 (27) 0 .4 2 2 8 (15) 0. 1633 (14) 0. 6985 (29) -0. 3540 (14) 0 .4 1 7 6 (14) u> O J __ TA BLE 6 (Continued) A tom X m o lec u le #1 X z X m o lec u le #2 X z C (7) - 0 .4 6 6 6 (28) 0. 4739 15) 0. 0940 14) 0. 8831 (31) -0. 3851 16) 0 .4 2 3 0 (14) C (8) - 0 .3 3 3 2 (27) 0. 4917 13) 0.0301 13) 0. 9967 (22) -0. 3755 11) 0. 3445 (11) C (9) -0. 2640 (22) 0. 3916 11) -0 .0 2 6 1 11) 1. 0077 (21) -0. 2650 11) 0 .3 3 9 0 (10) C (10) -0. 1236 (28) 0. 4010 12) -0 .0 9 6 1 12) 1. 1202 (22) -0. 2466 12) 0 .2 6 3 4 (11) c (ID 0. 0307 (29) 0. 4710 18) -0. 0620 16) 1. 0554 (28) -0 .3 1 9 2 17) 0. 1706 (12) c (12) -0. 2247 (46) 0.4351 20) -0. 1671 16) 1. 3123 (26) -0 .2 5 8 0 18) 0 .2 7 6 2 (17) c (13) -0. 5270 (36) 0 .3 9 7 2 17) 0.2 2 0 8 18) 0. 5879 (44) -0. 3553 22) 0. 5036 (16) c (14) 0. 0686 (19) -0. 0526 13) 0.1 0 3 0 10) 0.4 1 3 6 (18) 0. 0372 10) 0 .2 6 8 8 (8) c (15) 0. 1319 (19) -0 .1 1 7 7 12) 0. 0215 10) 0. 3045 (19) 0. 0439 12) -0. 6697 (10) c (16) 0 .2481 (16) -0. 0569 12) -0. 0143 10) 0. 3111 (16) 0. 1407 11) 0 .3 9 4 4 (9) c (17) 0. 2577 (16) 0. 0500 12) 0.0 4 8 6 10) 0.4 3 2 8 (17) 0. 2027 11) 0. 3573 (9) c (18) 0. 1416 (19) 0. 0475 13) 0 .1 2 2 5 9) 0.4 9 1 9 (18) 0. 1375 11) 0. 2753 (8) u 3.4 (19) -0. 0239 (15) -0. 1998 9) -0. 1927 8) 0. 5998 (16) 0. 2928 9) 0. 5645 (8) TA BLE 6 (Continued) A to m X m o lec u le #1 X z X m o lec u le #2 X z_ C (20) 0. 1203 (18) -0. 1581 (11) -0. 2309 (9) 0 .4 6 0 6 (17) 0. 2545 (10) 0. 6072 (9) C (21) 0. 2158 (19) -0. 2187 (11) -0. 2995 (9) 0. 3600 (17) 0. 3251 (10) 0. 6697 (9) C (22) 0. 1719 (23) -0. 3202 (14) -0. 3279 (12) 0 .4 0 1 3 (20) 0. 4280 (12) 0. 6936 (10) C (23) 0. 0376 (21) -0. 3674 (12) -0. 2910 (10) 0. 5358 (18) 0. 4656 (11) 0. 6462 (9) C (24) -0. 0618 (18) -0. 3025 (11) -0. 2219 (9) 0. 6329 (16) 0. 3978 (9) 0. 5830 (8) C (25) -0. 2756 (13) -0. 0578 (8) -0. 1807 (7) 0. 8504 (15) 0. 1524 (9) 0. 5623 (8) C (26) -0. 2784 (17) -0. 0974 (10) -0. 2717 (9) 0. 8461 (18) 0. 1973 (11) 0. 6530 (10) C (27) -0. 3756 (18) -0. 0549 (11) -0. 3225 (9) 0. 9524 (18) 0. 1648 (11) 0. 7083 (9) C (28) - 0 .4 7 8 4 (20) 0. 0243 (12) -0. 2846 (10) 1. 0436 (17) 0. 0835 (10) 0. 6722 (9) C (29) -0 .4 7 4 1 (16) 0. 0666 (10) -0. 1930 (8) 1. 0455 (20) 0. 0371 (12) 0. 5852 (10) C (30) -0 . 3764 (17) 0. 0218 (10) -0. 1430 (9) 0. 9410 (17) 0. 0686 (10) 0. 5255 (9) C (31) -0. 3233 (14) -0. 1937 (9) -0. 0799 (7) 0. 8995 (16) 0. 2771 (9) 0 .4 5 0 9 (8) C (32) - 0 .4 5 3 5 (17) -0. 2493 (10) -0. 1426 (9) 1. 0264 (17) 0. 3662 (10) 0. 5092 (9) w in TA BLE 6 (Continued) m o lec u le #1 m o lec u le #2 A tom X 1 z X Z. z_ C (33) -0. 5861 (16) -0. 3097 (10) -0. 1172 (8) 1. 1535 (19) 0. 4003 (11) 0 .4 8 1 9 (10) C (34) -0. 5884 (17) -0. 3189 (11) -0. 0352 (9) 1. 1551 (20) 0. 3995 (12) 0. 3960 (10) C (35) -0 .4 6 5 3 (20) -0. 2630 (12) 0 .0 2 4 9 (10) 1. 0262 ( 1 9 ) 0. 3417 (11) 0. 3361 (10) C (36) -0. 3301 (16) -0. 2024 (9) 0. 0022 (8) 0. 8989 (16) 0. 2778 (10) 0. 3636 (8) T h erm al P a r a m e te r s Isotropic T h erm a l P a r a m e te r s A tom m o le c u le #1 B_ m o le c u le #2 B A tom m o lec u le #1 B m o le c u le #2 B C (19) 4 . 0 (2) 4. 6 (2) C (24) 5.1 (3) 4 . 7 (2) C (20) 5. 1 (3) 5. 2 (3) C (25) 3. 3 (2) 4. 5 (2) C (21) 5. 7 (3) 5. 2 (3) C (26) 5. 1 (3) 5 .7 (3) C (22) 7. 1 (4) 6. 1 (3) C (27) .5.3 (3) 5 .9 (3) C (23) 6. 3 (3) 5. 6 (3) C (28) 6. 0 (3) 5. 2 (3) TABLE 6 (Continued) m o le c u le #1 A tom B m o le c u le #2 B Atom m olec u le #1 B m o le c u le #2 B C (29) 4 . 8 (3) 6. 6 (3) C (33) 4. 6 (2) 5. 8 (3) C (30) 5 .0 (3) 5 .2 (3) C (34) 5 .0 (3) 6 . 4 (3) C (31) 3 .8 (2) 4 . 6 (2) C (35) 5 .9 (3) 6. 0 (3) C (32) 4 . 9 (3) 5 .4 (3) C (36) 4 . 3 (3) 4 . 6 (3) A nisotropic T h erm a l P a r a m e te r s m o lec u le #1 A tom 104/3 11 l ° 4@ 22 ^ 3 3 1O40 1 2 TO4* P 13 TO V P 23 Fe 147 (3) 5 7 (1 ) 46 (1) 39 (3) 5 (2) 37 (2) P 157 (6) 61 (2) 36 (1) 34 (5) 18 (4) 40 (3) O (1) 229 (21) 94 (8) 60 (6) 100 (20) 61 (17) 53 (10) O (2) 296 (27) 74 (8) 143 (9) 49 (24) -107 (25) 30 (14) O (3) 228 (21) 51 (6) 89 (6) 60 (17) -3 (17) 26 (9) oo -J TA B L E 6 (Continued) A tom 104 1U /9 11 1 0 * 2 2 IO4 . (333 104 P 12 io 4 Z 3 13 1qAs ' 23 C (1) 224 (21) 94 (8) 60 (6) 100 (20) 61 (17) 53 (10) C (2) 227 (26) 46 (9) 58 (7) 41 (23) 10 (21) 33 (12) C (3) 162 (25) 78 (11) 85 (9) -27 (26) -23 (23) 81 (15) C (4) 322 (37) 65 (11) 86 (10) 67 (30) -25 (29) 57 (16) C (5) 395 (44) 63 (10) 89 (11) 42 (33) 74 (33) 64 (17) C (6) 384 (48) 105 (16) 115 (13) 91 (43) 131 (40) 65 (23) C (7) 434 (55) 98 (15) 118 (14) 152 (46) 125 (43) 49 (23) C (8) 452 (51) 73 (12) 115 (13) 156 (38) -35 (39) 51 (19) C (9) 381 (39) 66 (10) 79 (10) 104 (31) -13 (30) 58 (16) C (10) 549 (56) 70 (12) 73 (11) -27 (39) 4 (38) 51 (18) C (11) 486 (59) 162 (21) 121 (16) -202 (59) 102 (48) 89 (29) (C (12) 828 (112) 160 (24) 89 (15) 106 (80) -14 (64) 98 (31) C (13) 618 (76) 114 (18) 169 (19) 38 (57) 290 (62) 59 (28) TA BLE 6 (Continued) A tom 10V l l 1q4 - (3 22 104/3 33 1 0 ^ 1 2 1o4/313 10> 2 3 C (14) 244 (32) 116 (14) 72 (9) 84 (35) -86 (26) 107 (19) C (15) 233 (29) 104 (12) 73 (9) 134 (31) 53 (26) 70 (17) C (16) 156 (25) 115 (13) 83 (9) 150 (29) 33 (23) 96 (18) C (17) 136 (22) 88 (12) 97 (10) 42 (25) -56 (23) 55 (17) C (18) 232 (32) 146 (15) 49 (7) 96 (35) -73 (23) 67 (17) m o le c u le #2 ----------------------- 4 A tom TO ^ 10^ 1U (3 22 1 ° 4/3 3 3 r0V l 2 ‘ C V 13 l 0^ Z 3 Fe 173 (3) 69 (1) 34 (1) 61 (3) 13 (2) 37 (2) P 164 (6) 60 (2) 44 (2) 50 (5) 30 (4) 39 (3)- O (1) 251 (19) 85 (7) 60 (5) 40 (18) 12 (15) 73 (10) O (2) 328 (23) 80 (7) 56 (5) 67 (20) -28 (18) 31 (10) 0 (3) 262 (19) 68 (6) 51 (5) 54 (17) -45 (14) 43 (8) C (1) 210 (25) 69 (9) 50 (6) 102 (23) 45 (19) 54 (12) TA B L E 6 (Continued) A tom 101* 11 1C>4(3Z2 10V 3 3 1q4 i U /3 12 1o4/313 L° 4^ 2 3 C (2) 156 (23) 74 (9) 50 (6) 77 (22) 59 (18) 52 (12) C (3) 197 (25) 79 (9) 33 (6) 19 (23) 22 (18) 19 (12) C (4) 343 (34) 48 (8) 59 (7) 64 (25) 23 (23) 47 (12) C (5) 434 (42) 76 (11) 71 (9) 108 (33) 119 (30) 70 (15) C (6) 484 (55) 85 (13) 122 (13) 170 (44) 165 (42) 99 (21) C (7) 592 (61) 145 (19) 102 (14) 212 (56) 86 (46) 143 (27) C (8) 394 (41) 75 (11) 94 (11) 171 (33) 85 (32) 42 (17) C (9) 307 (35) 77 (11) 76 (9) 103 (31) ,21 (28) 45 (15) C (10) 318 (38) 80 (11) 78 (10) 49 (3,3) 80 (29) 24 (16) C (11) 463 (53) 161 (18) 68 (11) 68 (49) 124 (38) 64 (22) C (12) 267 (44) 151 (20) 180 (19) 94 (46) 9 (44) 79 (30) C (13) 922 (103) 200 (28) 118 (16) 123 (84) 199 (65) 216 (37) C (14) 268 (29) 81 (10) 40 (6) 71 (26) -73 (21) -5 (12) o TA BLE 6 (Continued) A tom 10> i i 104/3 22 10^ 3 3 1q4 0 1 2 1q4/^ 13 104/S 23 C (15) 227 (32) 108 (13) 70 (10) 44 (31) -38 (27) 42 (17) C (16) 198 (27) 92 (11) 54 (7) 37 (26) -34 (21) 42 (15) c (17) 222 (27) 88 (10) 52 (7) 43 (26) -29 (21) 60 (14) c (18) 267 (30) 101 (11) 44 (7) 137 (29) 19 (22) 61 (14) T A B L E 7 B o n d D is t a n c e s and A n g le s in [ff'- F e (C O )(P P h 3)C O O C 10H 19 (I] (A) B ond D is t a n c e s (in A n g s t r o m s ) m o le c u l e #1 I r o n -P h o s p h o r u s F e - P 2. 198 (3) I r o n -C a r b o n F e - C (1) F e - C (2) r r - c 5 H 5 : F e - C (14) F e - C (15) F e - C (16) F e - C (17) F e - C (18) Pho spho r u s - C arbon P - C (19) P - C (25) P - C (31) O x y g e n -C a r b o n C ( l ) - O (1) c (3)-0 (2) C ( 3 ) - 0 (3) O (3)-C (4) C a r b o n -C a r b o n 1. 672 (11) 2. 106 (13) 2. 087 (14) 2 . 106 (16) 2. 100 (13) 2. 115 (13) 2. 144 (14) 1. 814 (12) 1. 839 (11) 1. 852 (12) 1. 194 (15) 1. 218 (18) 1. 364 (16) 1 .4 7 1 (19) C (2 )-C (3) 1 .4 6 6 (20) C 5H 5> m o le c u l e #2 2. 193 (4) 1. 733 (13) 2. 104 (12) 2. 081 (13) 2. 098 (13) 2. 123 (13) 2. 119 (15) 2. 161 (14) 1. 837 (13) 1. 841 (13) 1. 819 (13) 1. 128 (16) 1. 217 (15) 1. 340 (15) 1 .4 4 3 (17) 1. 502 (19) 42 T A B L E 7 (Continued) m o le c u l e #1 m o le c u l e #2 m en th o l: C (4}-C (5) 1. 535 (24) 1. 526 (21) C (5 )-C (6) 1. 533 (28) 1. 562 (26) C (6 )-C (7) 1. 658 (31) 1. 526 (32) C (6 )-C (13) 1. 514 (34) 1. 597 (35) C (7)-C (8) 1. 484 (30) 1. 540 (28) C (8)-C (9) 1. 526 (25) 1. 551 (23) C (9 )-C (4) 1. 605 (23) 1. 524 (21) C (9)-C (10) 1. 558 (26) 1. 537 (23) C (1 0 )-C (11) 1. 458 (31) 1. 569 (26) C (10)-C (12) 1. 596 (35) 1. 520 (26) A vg. = 1. 546& 7T -C 5H 5 : C (14)-C (15) 1. 430 (22) 1. 396 (21) C (1 5)-C (16) 1. 401 (22) 1. 363 (22) C (1 6 )-C (17) 1 .4 9 9 (23) 1 .4 5 0 (20) C (1 7 )-C (18) 1 .4 6 7 (20) 1 .4 2 5 (19) C (18) -C (14) 1. 387 (26) 1 .4 3 4 (21) A v g . = 1. 425.8. p h en yl #1: C (1 9 )-C (20) 1. 412 (18) 1. 4 0 4 (18) C (20) -C (21) 1. 388 (20) 1 .4 2 2 (19) C (2 1 )-C (22) 1. 345 (25) 1. 361 (22) C (22)-C (23) 1. 385 (24) 1 .4 2 0 (21) C (2 3 )-C (24) 1. 436 (21) 1. 393 (19) C (2 4 )-C (19) 1. 353 (20) 1. 387 (19) p h en yl #2: C (2 5 )-C (26) 1. 381 (17) 1. 384 (19) C (2 6 )-C (27) 1. 399 (20) 1 .4 1 1 (21) C (2 7 )-C (28) 1. 377 (22) 1. 340 (21) C (2 8 )-C (29) 1. 393 (20) 1. 333 (21) C (2 9 )-C (30) 1. 412 (19) 1 .4 4 8 (21) C (3 0 )-C (25) 1. 370 (18) 1. 365 (19) 43 T A B L E 7 (Continued) m o le c u l e #1 m o le c u le #2 ph en yl #3: C (31)-C (32) C (3 2 )-C (33) C (33)-C (34) C (34)-C (35) C (35) -C (36) C (3 6 )-C (31) 1 .4 2 0 (17) 1. 390 (19) 1. 353 (19) 1. 362 (20) 1. 387 (20) 1. 352 (16) 1. 380 (18) 1. 409 (21) 1. 367 (22) 1. 397 (21) 1 .4 1 1 (20) 1. 397 (18) (B) B on d A n g le s (in d e g r e e s ) P h o s p h o r u s - I r o n - C a r b o n P - F e - C (1) P - F e - C (2) 92. 8 (4) 9 1 - 0 (4) 92. 8 (4) 91. 6 (3) C a r b o n -I r o n -C a r b o n C ( l ) - F e - C (2) 95. 9 (5) 100. 0 (6) I r o n - P h o s p h o r u s - C a r b o n F e - P - C (19) F e - P - C (25) F e - P - C (31) 116. 8 (4) 117. 5 (4) 115. 4 (4) 112. 4 (4) 118. 6 (4) 117. 8 (4) I r o n -C a r b o n -O x y g e n F e - C ( l) - O (1) 176. 8 (11) 1 7 2 .4 (11) I r o n -C a r b o n -C a r b o n F e - C (2)-C (3) 107. 1 (9) 109. 5 (8) C a r b o n - P h o s p h o r u s - C a r b o n C ( 1 9 ) - P - C (25) C ( 1 9 ) - P - C (31) C ( 2 5 ) - P - C (31) 101. 6 (5) 103. 1 (6) 99. 8.(5) 100. 9 (6) 103. 4 (6) 101. 4 (6) P h o sp h o r u s - C a r b o n - C a r b o n P - C (19 )-C (20) P - C (19 )-C (24) P - C (25)-C (26) P - C (2 5 )-C (30) P - C (3 1 )-C (32) P - C (3 1 )-C (36) 116. 8 (10) 125. 2 (10) 1 2 2 .6 (9) 120. 3 (9) 120. 0 (9) 120. 9 (9) 117. 0 (10) 123. 8 (9) 122. 3 (10) 116. 9 (9) 121. 1 (10) 118. 7 (9) 4 4 T A B L E 7 (C ontinued) m o le c u l e #1 m o le c u l e #2 C a r b o n -O x y g e n -C a r b o n C ( 3 ) - 0 (3 )-C (4) 116. 5 (11) 119 . ^ (10) O x y g e n -C a r b o n -C a r b o n O (2)-C (3)-C (2) 128. 2 (13) 124. 8 (12) O (3 )-C (3)-C (2) 110. 1 (11) 113. 7 (10) O (3 )-C (4 )-C (5) 106. 1 (13) 106. 2 (11) O (3)-C (4)-C (9) 104. 7 (12) 108. 0 (11) O x y g e n -C a r b o n -O x y gen O (2 )-C ( 3 ) - 0 (3) C a r b o n -C a r b o n -C a r b o n 121. 5 (14) 121. 5 (12) m en th o l: C (5 )-C (4 )-C (9) 107. 4 (13) 112. 2 (12) C (4 )-C (5) -C (6) 112. 7 (15) 110. 4 (14) C <5)-C (6 )-C (7) 103. 8 (16) 107. 0 (17) C (5 )-C (6 )-C (13) 108. 7 (18) 105. 7 (18) C (7 )-C (6 )-C (13) 108. 5 (17) 111. 0 (19) C (6 )-C (7 )-C (8) 111. 0 (17) 111. 7 (17) C (7 )-C (8 )-C (9) 111. 3 (16) 111. 2 (15) C (8 )-C (9 )-C (4) 108. 6 (14) 110. 6 (13) C (8 )-C (9 )-C (10) 115. 4 (16) 115. 5 (13) C (4 )-C (9)-C (10) 1 0 6 .9 (14) 112. 1 (13) C (9) — C (1 0 )-C (11) 115. 7 (16) 112. 3 (14) C (9)-C (1 0 )-C (12) 105. 4 (18) 111. 2 (15) C ( l l ) - C (10)-C (12) 7 f - C gH 5 : 111. 2 (19) 111. 0 (16) A vg. = 110. 3° C (18)-C (1 4 )-C (15) 112. 3 (14) 112. 3 (18) C (14) -C (1 5) -C (16) 1 0 7 .4 (14) 109. 9 (17) C (1 5)-C (1 6 )-C (17) 107. 5 (13) 105. 5 (15) C ( 1 6 ) - C (1 7 )-C (18) 106. 6 (13) 107. 3 (13) C (1 7 )-C (1 8 )-C (14) 106. 1 (13) 105. 3 (12) A vg. = 1 0 8 . 0 ° 45 TABLE 7 (Continued) m o le c u l e # 1 m o le c u l e # 2 ph en yl #1 C (24)-C 19)-C (2 0 ) 1 1 7 .9 (12) 1 1 9 .2 ( 1 2 ) C (1 9 )-C 2 0 )-C (2 1 ) 121. 9 (13) 118. 8 (13) C (2 0 )-C 2 1 )-C (2 2 ) 1 1 8 .4 (14) 122. 2 (13) C (21)-C 22) -C (23) 123. 1 (16) 118. 1 (14) C (2 2 )-C 2 3 )-C (24) 117. 2 (15) 120. 3 (14) C (2 3 )-C 2 4 ) -C (19) 1 2 1 .4 (13) 1 2 1 . 1 (1 2 ) ph en yl # 2 : C (30)-C 2 5 )-C (2 6 ) 117. 1 (11) 1 2 0 . 8 (1 2 ) C (25)-C 2 6 )-C (27) 120. 9 (13) 120. 4 (13) C (2 6 )-C 2 7 )-C (28) 122. 0 (13) 118. 6 (13) C (27)-C 2 8 )-C (29) 117. 9 (14) 1 2 1 .9 (14) C (28)-C 2 9 )-C (30) 119. 0 (13) 1 2 1 .5 (14) C (29) -C 30) -C (25) 123. 1 (13) 1 1 6 .4 (12) phenyl #3: C (36)-C 31 )-C (32) 119. 1 (11) 1 2 0 . 2 ( 1 2 ) C (31)-C 3 2 )-C (33) 119. 0 ( 1 2 ) 120. 4 (12) C (3 2 )-C 3 3 )-C (34) 1 2 0 . 9 (1 2 ) 119. 3 (14) C (33)-C 34 )-C (35) 1 1 9 .4 (14) 121. 3 (15) C (3 4 )-C 3 5 )-C (36) 1 2 1 .4 (14) 119. 2 (13) C (3 5 )-C 36) -C (31) 1 2 0 . 1 ( 1 2 ) 1 1 9 .4 (12) A vg. = 120. 0 ° 46 c d u ) The molecular structure of (‘ O^g**- ('K-G5H5)Fe(CO)(P?h3)GH2COOC10H19 (lib) . showing an absolute configuration about iron opposite to that of (la). C(28 C(16V (21 l*2bC(20)Fe Figure h . - p > T A B L E 8 O b s e r v e d and C a lc u la te d S tru ctu re F a c t o r s for ( + ) 5 7 g _ ( 7T - C 5H 5 )F e (C O )(P P h 3 )CH2 C O O C 1 0 H 19 (lib) The c o lu m n s d is p la y e d a re: h, 10 x P Q^ S > 10 x -^c a i c > and the p h a se an g le. F o r e x a m p le , the f ir s t e n tr y sh ow s that, fo r the O 3 -1 7 r e fle c tio n , P 0^ s = 9. 6 , c = 6 . 8 , and = 136° . H 3 -17 . ■ 5 0 77 86 IS e : 96 68 136 I 71 65 88 H 2 ; 50 . . 53 26 ii 4 > 1 7 0 H' 9 -1 5 1 0. 7 7 66 120 2 1 141 4 126 . -98 1 69 60 84 3 2 73 . 79 -44 4 H ' ■ 5 -17 3 M 10 - t S t 1 S3 91 0 '• H 1 52 65 -106 1 66 58 75 4 6 -17 •: H 1 -14 1 2 3 ,146 1*27 -7 0 65 58 86 4 1 119 100 -90 5 b ! -16 2 141 143 1 3 4 96 . P 8 ?R S M 0 03 67 -2 ? 79 92 -3 6 H ? -14 0 M 2 -16 ' n «3 74 90 2 I 191 197 -10 7 3 0 . . 90 69 1 2 2 266 241 1 4 1 53 62 - 163 3 46 47 1 34 2 65 60 -21 4 60 77 14 • M ft 3 -16 M - 14 0 0 134 1 07 -9 0 103 84 40 2 t 79 74 166 1 58 3 8 - 148 3 2 05 77 -49 2 221 198 - 1 5 • 4 3 12? 11 5 59 H 4 -16 4 94 85 -16 H f * 1 71 151 -50 H 4 * ' - t 4 0 1 89 91 31 1 2 1 06 9o — 85 o 223 210 -5 2 1 80 85 85 3. 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H 1 9 2 136 1 39 34 -6 21.1 21ft -9 H -1 2 10 -5 1 B? 1 70 7! -4 54 50 -61 1 1 0? 02 -1 7 -3 1 7 1 13 6 2 1 29 1 2? 24 -2 ftl 90 — 96 3 56 3 I 108 -1 494 463 6 4 . 66 80 -2 3 0 79 1 Oft 101 1 34 4 705 -2 M 1 1 10 2 36 4? -74 3 33 84 -12 1 87 77 1 14 6 1 0. 1 09 -60 ? 99 107 -14 6 1 18 I ? 1 1 ? 36 4.3 55 ’ 4 ftl 92 -? 0 H 2 9 | H — 10 ' to . -A 84 8 P -50 -6 54 54 ?« t :1 85 14 7 85 -4 96" 90 -119 ? 90 96 -5 9 1 — 3 1 SO 1 91 0 3 85 85 3 6 ’ -2 3ft • 53 - 1 25 4 86 04 -42 -1 7.87 281 -5 5 45 56 76 0 271 ?5? 06 74 95 - 76 H -9 . 10 2 4 ? 4 4 50 3 49 4 1 -ftft 1 .1 46 1 75 65 4 59 76 4 1 2 I CO 1 C7 - 1 76 6 06 92 ft 3 Oft 85 25 4 8 1 85 -66 M ? 9 5 101 08 ?5 -6 52 59 -1 3ft M -ft to . 20.3 1 70 -M — ? ?R9 20! 2 1 123 t 1 2 - 62 — 1 40 1 .74 -22 4 86 88 -7 ? 209 .2 13 7? 8 1 05 1 1 7 6 57 42 -1 59 6 89 99 96 73 70 - 1 1 76 72 -37 H -7 10 4 153 1 4ft 7 5 1 7 I ?o 89 1 1 39 135 30 6 4 0 19 -1 2 43 4 6 -34 3 '126 120 29 H 4 9 4 $R 87 -129 5 .119 1 4 0 -1 1 -4 60 84 - li f t 6 9? 99 67 - 3 371 316 -2? -2 255 2 3ft 62 H -6 IO -1 5ft 59 -59 9 61 79 3ft 1 1 31 1 3 3 6 2 97- 74 34 2 06 59 -65 3 72 88 -98 3 244 253 5 4' 189 200 -9 6 95 9? 44 5 t 46 1 57 62 H -5 !0 H 5 9 1 177 145 -12 -5 5 1 57 1 ? 2 03 ? A - 4 ? -3 1 64 t 66 -35 3 31 7 307 -6 -2 165 t 55 53 4. 1 66 1 74 66 — 40 53 — 94 6 122 I 1 ? 38 0 97 54 -19 2 1 30 I ?1 H -4 10 4 1 59 1 74 -?4 • * 5 81 94 50 1 22? 222 0 2 150 1?3 73 H 6 0 3 133 131 -26 4 171 1 94 54 - 5 91 1 09 -16 • 5’ 70 04 - 5 i -3 . 53 6 P -35 6 1 16 1 ?2 2 1 - 7 96 9? 57 -1 75 79 -1 1 1 M -3 16. 0 1 52 1 45 -2 2 1 69 1 61 -22 . I 310 29? — 13 3 75 64 3ft . 2 263 24 ft 48 . 3 91 79 1 59 H 7 9 4 103 84 -9 9 5 51 87 - I 0? -4 . 1 48 1 4? 41 , 6 s* , 91 -9.; -2 52 41 f t -1 95 1 08 -99 • M -2;' '.10' 0 1 2* 1 36 -14 05 82 65 ' 1 j’Wft . 264 -5 0 '' * I •55, 2 33* 370 32 0 50 72 t 33 - 6 1 14 1 1 3 54 1 48 20 a — 2 230 22 3 32 3 1 4 t 145 14 1 1 06 102 - 2 0 -5 1 25 1 1 0 167 2 77 82 . 0 M 4 12 -1 4? 54 117 4 57 • 43 - 1 0 2 102 99 99 -4 1 39 I 29 • - 2 4 137 143 -16 9 126 1 16 -76 6 91 87 o 3 37 49 -58 -3 76 76 -56 S 48 49 67 -4 109 1 22 80 3 1 16 «5 34 - 2 373 379 -5 -3 79 9ft -70 4 7? 67 “ 78 M ' -1 1 0 H 8 1 0 -1 142 1 20 75 w - 8 12 - 2 77 66 P9 0 1 1 7 91 — 22 -1 35 7 -1 2 ft M 1 13 ' 1 235 229 -63 - 2 67 , 7 * -70 1 262 247 64 1 • 62 59 - 1 30 o 48 36 -31 2 266 • 288 26 -1 97 1 1 3 13 2 107 1 14 142 2 151 I 49 -1 1 2 t s i 144 - 8 -A 104 s. 87 46 3 75 1 -145 0 55 32 -1 32 3 49 85 36 3 103 85 1 04 -3 90 03 -53 4 2 P2 199 2 1 63 67 -2 4 5 102 1 2 ? 0 4 14? 1 3ft -50 H 5 1 2 — 2 1 56 1 27 14 5 6 » 51 34 a 41 59 03 5 131 1 3ft 4? - 1 3? 34 79 6 1 1 9 86 0 H ! 1 I -3 47 54 -1 4ft • ft 99 100 -4 M ! 3 1 1 H . -7 1 2 - 2 65 50 2 1 1 ' .75 1 * i 3 M 0 1 n -4 1 28 1 32 -36 - 1 41 35 -P? 2 277 232 -?fl 2 1 14 117 -45 -3 3 7 57 26 1 80 82 -6.7 0 I 66 1 55 19 3 136 109 42 - 5 65 53 1 4 3 77 80 33 - 2 253 242 -35 2 1 3 1 146 — 22 1 1 54 1 47 95 '-4 1 63 124 - 6 8 -1 1 69 141 8 f t 3 190 1 7ft 6 ft 2 65 62 -39 H 2 13 -3 • 1 87 I 99 - 19 • M 1 2 1 1 0 07 76 - 106 4 9 7 97 — 60 3 66 61 5? -a 1 68 147 47 1 70 91 30 5 1 07 1 70 4ft -4 1 36 » 75 35 - 1 1 P9 21 0 -76 1 1 61 171 41 2 1 25 1 22 -71 w 6 1 2 — 3 57 50 1 S3 0 36 3 340 37 7 76 P9 36 3 I 13 1 13 -1 1 H — 6 i a - 2 101 48 - IS a 80 89 -25 4 72 P? 53 - 2 49 57 - 15 ft 4 7 6 0 -36 3 m 3 94 -71 M 1 1 1 1 s 40 6.3 - 1 0 1 79 36 - I 62 66 -57 2 1 76 184 ' - 45 4 203 201 -16 2 1 58 1 46 -i* 0 1 0 7 107 — 3 3 t 1 3 80 20 5 76 79 70 1 268 260 35 H 2 1 1 3 22 7 207 67 1 41 66 56 f 1 1 ® 1 O* •* ■ 5 5 2 81 76 55 5 121 1 1 1 4 3 W 3 1ft 3 *5 01 20 -5 1 20 1 22 -81 H 1 2 1 3 H 1 10 -4 1 0 ^ 163 -32 H - 6 1 2 -4 127 120 20 M 10 1 1 — 3 161 152 50 2 91 8? 18 -3 5ft 4 7 131 - 6 94 B6 98 — 2 1 7« • 176 -4 3 1 251 237 78 — 2 97 0 ft - 36 * 97 82 -1 43 1 1 78 1 65 21 -1 I 63 1 46 43 3 198 1 74 - 7 f t H 1 ! 1 3 ft 74 56 -1 13 -4 6 2 53 - 2 0 2 I 17 99 130 0 70 51 -96 4 124 1 23 125' i l e 5 137 26 -3 ?*7 223 -24 3 110 95 -31 1 35 62 - ! 0 ft 5 36 76 -56 1 1 34 1 t 4 94 . 80 7? 24 - a I 99 1 96 46 5 1 16 1 1 2 -40 2 1 66 1 65 -80 6 33 42 « 21 3 54 30 - 0 0 - i 22 1 224 -82 3 131 1 I 1 -33 H A 1 ft n ■ *75 342 1 4 w 1 1 4 1 21 1 1 4 51 H -4 I 2 N • m 1 3 1 21 t 21 7 1 09 - ft • 50 f t 0 79 a 86 74 — 6 3 1 93 95 -27 H 3 1 1 1 3 96 2 76 46 2 06 66 -47 - 2 . o | 9 ! - 36 3 63 40 -45 3 1 42 145 -39 2 1 1 2 1 05 153 3 6 ? 69 2 -1 5* S3 7 | 4 214 202 * — 23 5 1 25 t 2 7 -49 — 5 54 56 -1 1 1 7 229 2 1 8 9 4 t 30 1 1 2 -4 7 • n 1 2 3 m s -40 • 5 1 63 1 36 4 3 -4 t 19 1 25 -33 4 3ft 37 66 1 230 2 1 9 31 6 67 83 -56 H - 8 1 1 -3 1 82 1 00 54 8 90 71 - 6 H - Q 1 3 2 71 A -4 1 0 ! -1 1 41 1 31 79 M 2 1 0 1 75 56 -80 0 85 1 15 1 34 H - 3 1 2 1 30 31 -56 H ‘ 5 1 ft 2 31 44 94 1 1 02 70 10 2 104 1 03 -46 - 6 1 05 1 09 81 3 1 48 141 - 40 3 1 82 1 74 -23 1 250 272 2 ? 3 I 54 1 5? 18 — 2 S? 84 - 6 ! -5 69 46 - | 68 4 72 67 36 4 140] 15! 40 3 280 P 's ? - R ft 86 -45 -4 82 76 1 9 5 97 1 1 3 -40 4 33 32 -20 w -0 1 3 1 1 30 1 26 0 37 37 -1 9 H 4 1 1 5 1 35 1 22 -25 - a 1 94 1 84 23 M -7 1 1 6 42 15 3? 1 06 78 -75 w '1 I !A -I 40 37 -123 — 4 36 • ; 4? -60 ? 60 5? -66 e ?35 22! -4 1 1 37 142 - 74 . -3 58 ! 7! 1 7 H - ? 1 2 3 169 1 59 — K 1 , 87 71 -7 i 57 55 •67 2 1 40 1 40 66 - ? 3 6 24 - 1 37 0 00 1 ft J — ? 1 a 151 1 65 -17 3 130 120 -58 -1 59 : 61 40 t 167 1 63 6 M -1 f t 14 4 91 86 -49 4 - 120 96 1 2 1 1 00 1 07 -6 2 4? 47 40 H - 7 13 5 1 67 I 56 .32 6 63 35 -27 2 4? ? 4 1 3 5 T 1 79 1 71 -40 2 30 7 19 3 1 1? 1 1 O ft -4 1 4 1ft! 1 4ft 70 1 154 1.41 1 3 3 1 37 1 O '5 — ?3 M 3 1 0 H -6 1 1 4 1 31 jt 39 26 5 1 07 06 — 7 ft 3 101 163 -9 4 125 1 07 •0 4 M -9 1 4 -4' 62 •> 9 22 1 319 299 -4 6 M 1 6 1 f w -1 1 2 5 4 ft 2? - 1 39 -3 47 51 99 2 207 1 99 29 1 77 65 -45 - a 221 214 26 3 59 60 -64 — 3 70 05 19 1 10ft 07 -46 H - 6 1 3 2 5 1 50 -7 - i 91 81 1 2 8 4 2?7 24 1 I 9 -2 65 55 -07 3 24 ft : ?05 -30 1 1 « i 06 -60 63 6 > -19 5 100 1 06 85 0 53 1 55 34' 4 232 205 55 1 245 245 -3 4 1 4 ft 136 . 1 l 32 27 -107 6 49 61 -6 1 1 19 I 10 -34 5 1 ! t 06 -72 2 87 91 7? ? 1 58 173 -54 2 191 ? Q 1 33 3 1 1 « 1 1 4 -26 H -0 14 3 9C 82 1 9 H -5 1 1 M r 1 2 4 i «e 1 ?9 72 5 96 105 25 H j > 1 1 5 so 96 167 1 91 05 -34 1 333 315 -63 r -5 09 7ft 4? 2 . 161 140 30 M 4 1 0 2 295 273 2? -3 3ft : 5ft -24 — 3 230 ??4 to • 4 — .5 1 3 4 1 ?P 1 c 0 1 3 35 30 1 1 0 -2 34 19 74 -1 2R5 265 -1 1 -5 64 67 -67 4 21 1 208 1 3 - I 52 4ft -21 0 89 94 61 1 ft? 02 -61 H - 7 1 4 -4 1 37 1 45 1 3 5 . 83 8! 60 0 69 BS 55 1 60 33 -74 2 1 05 1 1 2 63 - ? 167 1 84 - g 6 87 07 - I 3 1 40 29 -90 2 135 141 -94 3 1 1 1 104 -29 1 0ft 92 -40 -1 141 142 91 P . t «2 1 92 21 3 220 2 1 0 -44 4 76 74 06 2 214 loo 30 6 . 56 84 - | 75 H -4 1 1 3 46 40 9ft 4 147 1 37 27 S 05 70 — 57 3 P7 6 1 1 25 1 67 89 48 5 6? 49 -1ft? ' A BO 6 f t -1 1 2 94 86 -76 1 259 222 -80 H 7 1 1 w -4 1 3 3 t 44 133 1 3 2 320 207 3 w 1 1 2 H — 6 1 4 5 67 70 2 3 1 33 1 05 6 0 — 2 40 4ft -29 1 37 -* o 1 0 4 88 102 -157 -1 t 10 1 3ft -20 -3 173 I 79 0 2 100 9i 57 1 47 * 0 -1 ftft H s 10 6 64 56 -91 0 57 76 26 — 2 55 42 106 5 1 5 I 1 37 -65 2 2«? 20 ft - c 2 6? 00 1 -1 20ft 202 -1 3 3 144 1 1 9 1 05 -5 • 72 63 -49 H -3 1 t 0 1 1 8 ,1 1 B 54 H - 3 1 3 4 56 40 -1ft -4 134 142 3 H — 1 3 12 1 4 7 ; 4 « -94 -3 1 16 110 81 I 102 90 -66 3 91 i 0:1 - e s 2 06 83 33 H - 5 14 -2 94 88 — 61 2 238 226 -2 1 1 25 1 30 - 1 5 4 1 0 1 91 9 3 06 91 1 66 -1 103 100 27 3 165 179 71 2 85 61 95 4 O ft P? -2 ! 1 op 46 1 ft? o 93 102 -28 4 43 35 — 63 H 2 1 2 2 233 1 8? i 166 1 85 22 5 64 36 -1 09 H 1 2 1 2 H -2 1 3 3 15! 1 1 1 5® 2 ■ t 06 1 19 -50 : 6 76 91 -63 -5 84 86 2 A 65 . 60 -35 3 IS2 1 53 7 1 1 62 1 63 -10 -3 1 ?9 1 69 — 25 1 1 64 1 44 1 ! 3 4 5 9 62 10? H -2 1 I 2 72 80 60 -2 1 O ft 9? 72 2 63 75 2 J» M -4 14 3 57 24 -04 -1 4 ft 67 -79 4 1 60 1 63 -3 H 6 10 2 - 103 93 -2 2 0 77 • 94 67 S 71 63 67 1 07 74 95 3 66 49. 105 H — 1 1 12 1 177 1 89 -72 2 205 1 60 — 3 3 • 4 1 34 f 35 -15 4 147 156 -54 2 1 75 1 60 31 H - 1 13 3 1 65 13? 5ft -3 1 17 1 27 65 6 66 82 • — 86 1 60 67 -57 3 5! . 55 -126 4 1 20 96 -66 -2 60 71 -48 2 91 102 75 4 7 ft 62 -5 1 100 90 t 20 -1 51 54 — 28 -1 1 1 4 49 47 4 ■ 2 62 69 - t 02 H .-a J 4 0 73 7! -47 M j 1 2 3 68 75 -5 t 217 217 6 1 143 123 60 H — 10 1 2 4 1 39 1 16 -9 1 46 79 77 3 135 157 -1 ? 2 74 ! 75 166 -4 56 : 6! 90 5 t 4 1 1 1 6 5? 2 I 75 150 -35 4 42 61 82 3 01 05 -1 14 2 Vos 9< 1 3 - 3 152 1 O ft — S? f t 144 115 61 4 73 60 -11 5 3 42 40 -42 — 2 • 132 1 \ 7 44 H f t 17 : 4 1 37 1 00 - 70 , H 7 io 5 1 1 1 121 -0 4 ?ft 77 -18 0 48 46 -4? 1 191 1 86 — 6 f t - s 47 47 -74 • H • -2 ' i 4 • 3 93 98 39 H 0 1 1 H -9 12 2 1 74 1 49 2 -4 55 35 -11 -2 65 71 ^81 _ _ _ _ _ _ _ 4 67 52 - 6 -3 179 164 -46 1 73 v , 5ft • I*- 5 6 i 2 38 A2 -94 - 1 43 34 -71 2 158 1 49 -17 H -9 16 • 3 39 26 A 0 56 57 -94 3 1 32 1 13 46 H -2 15 1 36 3 2 1 75 A TO 65 -98 1 187 1 67 -31 1 >? TO 2S Z . 88 7 3 - 24 2 76 74 77 M -7 15 1 92 91 -67 55 64 - » 28 H - 1 14 3 59 45 -58 1 64 70 45 2 3 55 168 13 121 15 -44 H — 8 M ’ -2 16 1 1 J 5 90 • 6 H 3 1 4 3 127 124 34 ' ‘ *15 I I 36 1 17 0 3 1 10 106 -A “ 1 91 61 9 H -6. 15 H -1 2 81 92 ' 96 7 !l4 3 107 -18 H’ 0 14 1 2 147 79 127 79 -27 74 1 89 95 39 1 2 1 31 93 I 07 77 -A 5 29 H -7 1 6 M - 1 16 -A 150 132 -1 2 2 35 36 150 3 1 I 2 53 -44 1 1 88 1 49 -7 2 1 166 122 -32 - 2 1 1 1 1 1 1 -39 M A 1 4 3 86 74 -3 2 : 99 00 51- - I 69 68 69 H 0 15 H 0 16 t 129 126 34 - I 82 52 -1 8 H -5 15 H -6 ' 16 2 9 A 89 -04 0 73 50 63 - 3 1 87 17? -3 0 ‘ 5* 52 -21 3 1 61 148 -7 1 43 4 ] -61 1 1 13 95 29 — 2 100 94 8 0 1 1 15 91 - 32 A 65 62 ■ 53 2 52 35 168 1 1 04 92 -52 2 76 64 70 H -6 17 H 10 15 3 1 08 95 -17 2 165 1 34 21 3 46 30 -70 M 1 1 A 1 87 ’ 78 -74 H -4 1 5 H 1 15 H — 5 16 1 * ■ = 60 55 105 - 3 139 133 63 2 14| 1 23 . -4 H -5 1 7 -2 62 rp — 194 1 123 104 8 -1 89 74 -57 1 4 4 44 -1 20 - I A 1 3 A — 28 M -9 ! 5 2 96 74 1 24 0 123 1 23 9' ? 67 51 37 1 ; 44 4 3 57 0 A5 30 — 74 3 - ! 30 1 1 0 -27 1 49 34 — 18 3 88 6? -79 1 1 1 0 to i -17 1 130 93 - 79 2 155 1 27 14 H • — 4 17 3 t 1 7 85 -50 2 3 207 132 1 82 1 12 - 4 62 H -3 1 5 H 2 ! 5 H -4 16 1 • 59 41 24 H 2 1 A 1 80 68 — 39 2 51 56 -3 M -8. I 5 2 75 34 74 - 1 99 84 -56 3 1 05 46 -1 10 i -3 1 12 10A . 36 3 1 37 1 1 1 -46 0 1 35 I 08 S ' -2 A 7 3> • -6 7 1 93 70 -76 4 109 «0 46 H -3 16 ' ' ! ' 1 ! 5'7j D is c u s s i o n The u s e of o p t ic a lly - a c t iv e tr a n s itio n m e t a l c o m p le x e s h a s m a d e it p o s s i b l e to fo llo w the s t e r e o - c h e m i c a l c o u r s e of s e v e r a l r e a c tio n s at a m e t a l c e n te r . R e c e n t stud y on p s e u d o - t e t r a h e d r a l iron c o m p le x e s e x a m p le s include the finding that p h o to c h e m ic a l 18 d e c a r b o n y la tio n r e a c tio n s p r o c e e d w ith in v e r s io n at the m e t a l and that S C ^ - in s e r t io n r e a c tio n p r o c e e d s w ith high s te r e o - s p e c ific ity , te n ta tiv e ly , rete n tio n at the m e ta l. ^ The r e s o lu tio n of the o p tic a lly a c tiv e m e t a l c o m p le x e s is u s u a lly a c h ie v e d by f ir s t p r e p arin g d i a s t e r e o m e r i c c o m p le x e s in w h ich a s t e r i c a l l y in varian t sid e grou p Jsuch a s a ( - ) - m e n t h o l g r o u p ^ , 19-21 or a (g) (-) « ^ -p h e n y le th y la m in e groupj ^ is a tta ch ed to an o t h e r w is e r a c e m ic m e t a l c e n te r . T h is g iv e s a p a ir o f d i a s t e r e o m e r i c a l l y - r e l a t e d m o l e c u l e s (below ) w h ich can in p r in c ip le be s e p a r a te d to y ie ld c o m p le x e s w h ich a r e s t e r e o c h e m i c a l l y pu re at the m e ta l. In o r d e r to fo llo w the s t e r e o - c h e m i c a l b e h a v io r of t h e s e m e t a l c o m p le x e s , it is e s s e n t i a l that s o m e e x p e r im e n t a l tech n iq u e be X (A = c h ir a l sid e group) 58 a v a ila b le to m o n ito r the c o n fig u r a tio n at the m e ta l. One c o n ven ient and c o m m o n l y - u s e d tech n iq u e is c i r c u la r d ic h r o i s m s p e c tr o s c o p y : h e r e one a r g u e s that co m p o u n d s of s i m i l a r s tr u c tu r e w ith UV bands w h ich a r e a s s ig n a b le to known tr a n s itio n s should h a v e CD bands c o r r e s p o n d in g to t h e s e t r a n s itio n s , the s ig n s o f w h ich w ill be the s a m e fo r co m p o u n d s of the s a m e a b so lu te c o n fig u r ation. In the c a s e o f t h e s e u n s y m m e t r i c a l o r g a n o m e t a llic c o m p le x e s w h e r e su c h U V -C D band c o r r e la t io n s a r e not yet p o s s ib le , the e m p ir i c a l a s s u m p tio n h a s b e e n m a d e that c o m p o u n d s o f v e r y s im il a r s tr u c tu r e h aving the s a m e a b so lu te co n fig u r a tio n at the m e t a l sh ould h a v e g r o s s l y s i m i l a r fe a tu r e s in th e ir C D s p e c tr a . 1^ > ’ 1 9 - 2 1 T h is r e a s o n a b le a s s u m p tio n is w id e ly a c c e p te d but h as so fa r not b een u n e q u iv o c a lly p r o v e n , at le a s t not fo r te tr a h e dr a lly - c o o r d in a t e d T T -co m p le x es. W hat is c l e a r ly n e e d e d in th is a r e a of r e s e a r c h is e m p ir i c a l c o r r o b o r a tio n for a s u ffic ie n t n u m b e r of e x a m p le s that one can c o r r e la t e c e r t a in o b s e r v a b le bands w ith a b s o lu te co n fig u ra tio n . W hen w e s t a r t e d o u r in v e s t ig a t io n s , the only a b so lu te c o n fig u ra tio n known f r o m X - r a y s tu d ie s w a s that of the c o m p le x (*)(R ) f (C 5H 5 ) F e (C O )(P P h 3) { c ( (S) N H C H C H 3 P h )C H 3} ] b F 4 (Ilia), w h o s e CD s p e c t r u m 1 ^ and s t r u c t u r e 17 a r e show n on the fo llo w in g page. 59 3 o o w > i 4 o tmji 4 S 4 * y * Our o r ig in a l intent w a s to d e te r m in e the a b so lu te c o n fig u r a tio n s o f the e s t e r c o m p le x (T T -C g H g J F e^ C O M P P b ^ C H ^ C O O C iQ H i^ (II) and its S 0 2 in s e r tio n adduct in o r d e r to c o n f ir m the finding that th is r e a c tio n o c c u r r e d w ith r ete n tio n at iron. 14 D iffic u ltie s w ith r e c r y s ta lliz a t io n , h o w e v e r , c a u s e d u s to shift ou r e ffo r ts to the e th e r c o m p le x ( ^ -C g H g jF e fC Q H P P h g J C H ^ -O C jQ H ^ g (I). The a b so lu te c o n fig u ra tio n of (f ) 5 7 ^ 5^ 5 ) -F e f C O H P P h j ) 22 C H 2O C 1 0 H 19 (la) w a s s o lv e d in th e c l a s s i c m a n n e r of B ijv o et, w h ich r e q u ir e s the c o lle c tio n o f two s y m m e t r y - r e l a t e d data s e t s w ith o p p o site p h a s e a n g le s (the hkl and hkl data s e ts in this c a s e ) . The p r e s e n c e o f an a n o m a lo u s ly s c a t t e r in g a to m (the iron a to m in th is c a s e ) c a u s e s s lig h t d if f e r e n c e s in the in t e n s it ie s of t h e s e two o th e r w is e id e n tic a l data s e t s , and t h e s e d if f e r e n c e s can be u tiliz e d to g iv e the c o r r e c t c o n fig u r a tio n a l a s s ig n m e n t. The c o r r e c t a b so lu te c o n fig u r a tio n of (la) (R) w a s id en tifie d by virtu e of the fa ct that is r e fin e d to a s ig n ific a n tly b e t t e r R fa c to r than its m i r r o r 60 im a g e (8 . 5 p e r cen t vs* 9*4 p e r cen t). The s p e c t r a l and s tr u c tu r a l d e ta ils o f (la) a r e show n b elo w : 20 -|0 - 350 n m B y th is t im e the o r ig in a l e s t e r c o m p le x (-f )g7 g - ( TT'-CgH^JFe ( C O H P P h ^ J C H ^ C O O C j q H ( l i b ) w a s s u c c e s s f u l l y r e c r y s t a l l i z e d . The s tr u c tu r e d e te r m in a tio n of th is co m p o u n d w a s c o m p lic a t e d b y the p r e s e n c e of two ind ependent m o l e c u l e s in the unit c e l l and an exasper ating p s e u d o - s y m m e t r y p r o b le m w h ich w a s s o lv e d on ly w ith difficulty. On the o th e r hand, a s im p lif ic a t io n w a s e m p lo y e d h e r e : the a b so lu te c o n fig u ra tio n of the m e n th o l grou p a s d e te r m in e d f r o m the p r e v io u s a n a ly s is now w as u s e d as a " h a n d le” to id en tify the c o r r e c t c o n fig u r a tion: the B ijv o e t m e th o d , t h e r e f o r e , w a s not c a r r ie d out in th is c a s e . * 9 -3 * A s s u g g e s t e d b y M a th ie s o n , the a b so lu te c o n fig u r a tio n arou n d an a to m can be d e te r m in e d b y o r d in a r y X - r a y te c h n iq u e s if an in te r n a l known a s y m m e t r i c r e f e r e n c e c e n te r is p r e s e n t in th e m o l e c u le . In the p r e s e n t c a s e , the in te r n a l r e f e r e n c e is the (-) m e n th o l group, w h o s e a b so lu te c o n fig u r a tio n is w e l l - e s t a b l i s h e d . T h us, it w ould h a v e b e e n p o s s i b l e to d e te r m in e the s t r u c t u r e s o f b oth (la) and (lib) w ithout u s in g a n o m a lo u s d is p e r s io n m e th o d s . N e v e r t h e l e s s , in the c a s e of co m p o u n d (la) w e c h o s e to do the job in a c o m p le t e ly u n b ia s e d m a n n e r as if w e k n ew noth ing about the m e n th o l co n fig u ra tio n in o r d e r to a llo w the X - r a y data alon e to t e ll u s the a n s w e r . It w a s g ra tify in g , of c o u r s e , to find that the fin a l r e s u lt s did in fact show m e n th o l in its c o r r e c t a b so lu te c o n fig u ra tio n . 61 A c o m p a r is o n o f th e CD s p e c t r a l and s tr u c tu r a l d e ta ils of (lib) (show n b elo w ) w ith th o s e of (la) and Ilia) g iv e n e a r l i e r c l e a r l y s h o w s that th e s p e c t r a l r eg io n f r o m 300 to 37 5n m (the h ig h - e n e r g y region ) is a s e n s i t iv e in d ica to r o f the a b so lu te co n fig u ra tio n about iron. The CD s p e c t r a of (la) and (Ilia) in th is r e g io n a re r a th e r s i m i l a r w h ile that of (lib) is r e v e r s e d . The X - r a y r e s u lt s on t h e s e th r e e c o m p le x e s sh o w that th e a b so lu te c o n fig u r a tio n s o f (la) and (Ilia) a r e d iffere n t f r o m that o f (lib). The X - r a y r e s u lts a ls o c o n f ir m the e x p e c te d n otion that the m a in f e a tu r e s o f the CD s p e c t r a c o m e f r o m the c h ir a l m e t a l it s e l f and not f r o m the c h ir a l sid e group. 20 * . — W ith the ab ove a b so lu te c o n fig u r a tio n a l d e te r m in a tio n s , the a b so lu te c o n fig u r a tio n s of a w h ole s e r i e s o f co m p o u n d s (F ig . 5) a r e now known. T r e a tm e n t of (la) w ith a n h yd rou s H X (X = C l or Br) in e th e r p r o d u c e s ( T T'-C gH gJFe^O H PPh^JC H ^X tlV a), w hich can be r e d u c e d b y N aB H ^ in m e th a n o l to y ie ld (‘7/r-C ^H gjFefC O H PPh^JC H ^ (Va) along w ith v a ry in g am ount o f ( T /'-C gHgJFeCCOK PPl^JCH ^OCHj -3 0 I * * 4 o 10 10 0 3 ^ oonnt (Via) d ep endin g on co n d itio n s. The o p tic a l p u rity o f th e s e 62 LK T " ^ )0 O CQ >Q _ o ' tO G o \ 0 = 0 1 = 0 / ■ ^ U q V CL ° c f ~o cr- "b I I K > * O ? b ° CM O = 0 T = O 0 > i £ ^ u M r - u \ c> O A o GO 0 = 0 \_ C K J I o I »■ u> o C ° o CL !*) 6 3 S 1 ! A co m p o u n d s w a s found b y CD m e a s u r e m e n t s to b e u n ch a n g ed b y th is s e r i e s o f r e a c t io n s . SC>2 in s e r tio n r e a c tio n s c o n d u cted on (Ha) or (Va) r e s u lt s in in s e r tio n into the F e - C bond w ith ap parent rete n tio n of c o n f ig u r a t io n .* A ll the r e a c tio n s li s t e d in F ig u r e 5, t h e r e f o r e , o c c u r w ith u n ch a n g e d co n fig u ra tio n at iron. I n te r e s tin g ly , w ith the e th e r c o m p le x e s (la) o r Via), SC>2 in s e r tio n p r o c e e d s a b n o r m a lly to g ive in s e r tio n into the C H ^-O bond r a th e r than the F e - C bond. T h e s e o b s e r v a t io n s a r e c o n s is t e n t w ith s tr u c tu r a l d e ta ils . A c o m p a r is o n o f b on d len g th s in (la) and (lib) r e v e a l s the fo llo w in g fe a tu r e s : (i) the F e - C bond le n g th in (la) 2 .0 0 1 (18)X is s ig n ific a n tly s h o r te r than that in (lib) 2. 105 ( l 6 )Ji; (ii) the CH ^-O d ista n c e in (la) 1 .4 7 4 (9)51 is m u c h lo n g e r than the O -C (m enthol) d ista n ce 1. 391 (8 )S. in (la) and is a lso lo n g e r than the sta n d a rd C -O bond len gth in e t h e r s 1 .4 2 6 (5)&. profound in flu e n c e on the e le c t r o n ic tr a n s itio n s (and, t h e r e f o r e , the CD) w h ile fo r tu ito u s ly not changing the C D c u r v e m u ch . T h is is why w e n e e d the X - r a y for the SC>2 in s e r tio n produ ct o f (lib). S Q ? insertion 0 I I SC > 2 insertion. C han ging the 4th lig a n d f r o m -C^ to -S-<5- cou ld h ave 64 T h e s e fa cts s u g g e s t that F e - C bond in (Elb) and the CH^-O bond in (la) a r e w e a k e r than u s u a l and p robab ly a r e s u s c e p tib le to SO 2 - induced c le a v a g e as show n b elo w . © 9 3p c 0 F e ' i ''C H ; I* Je j F e - _______ O ^ P 'C H 2 I c I T h is is fu rth er su p p o rted by a r e la tiv e ly sh o rt F e . . . C((l) d ista n ce of 2. 931 (14)A in(IIb), s u g g e stin g the p r e s e n c e of s o m e e le c tr o n 1 48 d e lo c a liz a tio n that w ould d e c r e a s e the F e -C H ^ bond o r d e r (lie). The V c = o (acyl) of l 6 5 0 c m - ^ in(IIb)^ w hich is s ig n ific a n tly lo w e r than a n o r m a l V*c = o of ~ '1 7 3 5 c m - ^ , is a lso c o n s is te n t with fo rm u la tio n (He). The d ih ed ral an gle b e tw e e n the F e -C (2 )-C (3 ) and C ( 2 )-C (3 )-0 (2 ) p la n es is 83. 3° in m o le c u le #1 and 8 8 . 0° in m o le c u le 65 # 2 . W o jcic k i and c o - w o r k e r s h a v e p r o p o s e d a m e c h a n i s m for SOg in s e r tio n r e a c t io n s w h ich in v o lv e s in itia l b a c k s id e attack of the SC>2 m o le c u l e on the - ca rb o n a to m . ° F r o m the p r e s e n t r e s u lt s , su ch an attack a p p a r e n tly r e s u lt s in the c l e a v a g e of e ith e r the F e - C or C -O bond, w h ic h e v e r is w e a k e r . 66 CHAPTER II THE S T R U C T U R E A N A LY SIS O F ( n 5 - C 8H 9 )(V\7 - C 8 H 9 )R u3 (CO)6 IN T R O D U C T IO N The r e a c tio n o f c y c lo o c t a t e t r a e n e w ith R.u3 (C O )j2 to g ive c o m p le x e s o f p en ta le n e h a s b e e n a su b jec t o f c o n s id e r a b le in t e r e s t 7 7 78 r e c e n tly . ' P e n ta le n e , w h ich is p r e d ic te d to h a v e in the groun d sta te in p o ly o le fin str u c tu r e I, is u n sta b le , and a tte m p ts to p r e p a r e the c o m p o u n d by c o n v e n tio n a l o r g a n ic s y n th etic p r o c e d u r e s have 29 30 fa iled . * It is known, h o w e v e r , that o c c a s io n a l ly tr a n s itio n m e t a ls can f o r m sta b le c o m p le x e s w ith o r g a n ic m o l e c u l e s w h ich a r e u n sta b le un d er n o r m a l c o n d itio n s . K atz and c o - w o r k e r s f ir s t O O ^ s y n th e s iz e d the dianion II, an a r o m a t ic t e n -TT- e l e c t r o n s y s t e m fr o m d ih y d ro p en ta len e, and t r e a t e d it w ith v a r io u s tr a n s itio n m e t a l I nr 67 h a lid e s (in a n a lo g y w ith the s u c c e s s f u l s y n th e s is of p e n ta h a p to cy - 33 c lo p e n ta d ie n y l c o m p le x e s f r o m m e t a l s a lts and the c y c lo p e n - ta d ien id e iron). H o w e v e r , an X - r a y c r y s t a llo g r a p h ic study^^ h a s shown that the ir o n c o m p le x , F e (C g H £))2 (III), f o r m e d in this m a n n e r f r o m f e r r o u s c h lo r id e , co n ta in s a c a r b o n - c a r b o n bond joining the p a ir of C g r in g s not b on ded to the iro n a to m . The is o e l e c t r o n ic ^ C o (C g H 6 )2 j + p ro b a b ly ha s a s i m i l a r s tr u c tu r e . T r e a tm e n t o f N iC l2 and C 0 CI2 w ith (II) y ie ld s the b in u c le a r m e t a l c o m p le x e s N i2 (C gH^)2 and C o 2 (C gH ^)2 > but in the a b s e n c e of s i n g l e c r y s t a l X - r a y c r y s t a llo g r a p h ic stu d ie s th e ir n atu re is u n c le a r . The r e a c tio n b e tw e e n c y c lo o c t a t e t r a e n e and R u g (C O )j2 w ith O C o L b o ilin g h ep tan e w a s r e p o r te d ' to g iv e s e v e r a l c y c lo o c ta te tr a e n e c o m p le x e s . F u r th e r r e a c tio n g iv e s two n e w p ro d u cts in low y ie ld , one of w h ich is a c o m p le x o f p en ta le n e Rug(CO)g(CgH^) ^ (IV), and the o th e r a c o m p le x w h o s e s tr u c tu r e is the su b je c t of th is ch ap ter. The in fr a r e d s p e c t r u m |>)c o (hexane) 2 0 1 2 m , 1 9 8 7 s, 1 9 5 4 s, 1931m , 1830w . cm ~ ^ J o f th is n ew red c r y s t a ll in e c o m p le x (m. p. 194°) (V), O O w h o s e m o le c u l a r s tr u c tu r e h a s b e e n r e p o r te d . T h e s e fa c ts, taken in con ju n ction w ith a n a ly tic a l, m a s s s p e c t r a l, and n. m . r. data [ 4 . 73m (3H ), 4. 8 2 t(lh ), 5. 94t(2H), 6. 93t of d (2H), 7. 46m (8H ), 8. 5 0 m (lH ), 8. 7 5 m ( l H ) j f , s u g g e s t a r e la t e d s tr u c tu r e w ith f o r m u lation R u 2 (C O )^(CgH^)2 . 68 ( o c ( c o ; A .« ( c o ; a oc oc oc J L Y THE S T R U C T U R A L A N A L Y SIS O F (C 8H9 )2R u 3 (CO)6 C o lle c tio n and R ed u ctio n o f X - r a y D ata C r y s t a ls o f R u g fC O J ^ C g H ^ ^ w e r e su p p lied by P r o f. F . G. A. Stone and Dr. S. A. R. Knox o f th e U n i v e r s it y of B r i s t o l . A s e r i e s o f p r e c e s s i o n p h o to g ra p h s w e r e taken o f the hOl, hkO, Okl, hll, hkl, and the lkl n e ts u s in g a N on iu s p r e c e s s i o n c a m e r a w ith M o-K m rad iation. F r o m t h e s e p h o to g ra p h s the m o n o c lin ic s y m m e t r y o f the c r y s t a l s w a s app aren t. The o b s e r v e d e x tin ctio n con d ition (hkl: h + k = 2n) w as c o n s is t e n t w ith s p a c e grou p s C 2 / m (No. 12) o r C2 (No. 5) o r C m (No. 8) w ith a = 24. 9 3 4 - ( l 1)5, b = 12. 632(6)5., c = 14. 669(8)5., <? = 114. 31(2)° , and V = 4 1 8 5 . 5A 3 . The d en sity , c a lc u la te d fo r eig h t m o l e c u l e s p e r unit c e ll, w as 2. 1 7 4 g /c m ^ w h ich O a g r e e s w e ll w ith the valu e 2. 0 4 2 g / c m m e a s u r e d by floatin g a c r y s t a l in an aq u eou s so lu tio n o f zin c iod ide. A c r y s t a l w a s m o u n te d on a c o m p u t e r - c o n t r o ll e d N on iu s C A D -3 d iffr a c to m e te r w ith the ^ a x is p a r a lle l to the 2 0 1 69 r e c ip r o c a l a x is . D ata w e r e c o l le c t e d b y the 0 /2 0 scan tech n iq u e u sin g the Mo-Km ra d ia tio n up to a 20 m a x im u m o f 4 5 ° . A total o f 5357 r e f le c t io n s (including 90 c h e c k r e f le c t io n s ) w e r e c o lle c t e d in the m a n n e r d e s c r ib e d in C h ap ter I. T h r e e c h e c k r e f le c t io n s w e r e m o n it o r e d at 60 - r e fle c tio n in te r v a ls and s h o w e d no s ig n ific a n t v a r ia tio n in in ten sity . The 2 sta n d a rd d eviation of e a c h in te n s ity r ea d in g , )> w as e s t i - 2 m a te d u s in g the fo r m u la <3"(F0 ) = (total count + 0. 04 (net 2 1 /? in ten sity) ) ' . R e fle c tio n s w h o s e n et in te n s itie s w e r e l e s s than 3*r w e r e c o n s id e r e d u n o b s e r v e d and w e r e e lim in a t e d f r o m the s u b s e quent s tr u c tu r a l a n a ly s is . An a b so r p tio n c o r r e c t io n w a s not a p p lied i s in c e the in te n s ity of an a x ia l r e fle c tio n (at y = 90°) s h o w e d e s s e n tia lly no v a ria tio n w ith . The in t e n s it ie s w e r e c o r r e c t e d for L o r e n tz and p o la r iz a tio n e f f e c ts , and p la c e d on an a p p r o x im a te ly a b so lu te s c a le by m e a n s of a W ilso n plot. A t the end o f data r e d u c tion, 2211 n o n - z e r o r e f le c t io n s w e r e left. Solution and R e fin e m e n t o f the S tr u c tu r e The m a j o r c o m p u ta tio n s w e r e p e r f o r m e d w ith a s y s t e m of c r y s t a llo g r a p h ic p r o g r a m s known as C RY M , d e v e lo p e d by Dr. R ic h a r d M a r s h 's group at the C a lifo r n ia In stitu te of T ech n o lo g y . The p r o g r a m O R T E P , w ritte n b y C. K. J oh n son of the Oak R idge N a tio n a l L a b o r a to r y , w a s u s e d to illu s tr a te the g e o m e t r y of the com p ou n d. 70 In te rp reta tio n of the t h r e e - d i m e n s i o n a l P a t t e r s o n m a p sh o w ed an a to m ic a r r a n g e m e n t c o n s is t in g o f two in dependen t Ru^ f r a g m e n t s , e a c h situ a ted on a m i r r o r plane (S ch em e I). T his a r r a n g e m e n t in d ic a te d that the c o r r e c t s p a c e group w a s m o s t p rob ab ly C 2 /m . U sin g the c o o r d in a te s d e r iv e d f r o m this P a t t e r s o n a n a ly s is , a s tr u c tu r e fa c to r c a lc u la tio n and d iffe r e n c e F o u r i e r m a p r e v e a le d the p o s itio n s o f the s i x c a r b o n y l g r o u p s and tw o CgH^ g ro u p s v e r y c l e a r ly . The m o le c u l a r f r a m e w o r k , show n in S c h e m e II, c o n s is t s o f an Rug tr ia n g le w ith two d iffere n t CgHq lig a n d s (one b ic y c lic and the o th er m o n o c y c lic ) in the m o le c u l e . F o u r c y c l e s of f u l l - m a t r i x l e a s t - s q u a r e s r e fin e m e n t w ith is o tr o p ic t h e r m a l p a r a m e t e r s for a ll the ca rb o n and ox y g en a to m s o f the s tr u c tu r e r e s u lt e d in R f a c to r s of 5. 9 p e r cen t and R w = 8. 0 p e r cen t. In the c o u r s e o f the s tr u c tu r e a n a ly s is d iffic u ltie s w e r e e n c o u n te r e d w ith a to m s C ( l l ) and C (14). T h e s e w ill be d i s c u s s e d la t e r in th is ch ap ter. Y Sctame I Scfieme x 71 The a to m ic p o s itio n s f r o m the fin a l l e a s t - s q u a r e s r e fin e m e n t c y c le w e r e u s e d to c a lc u la te the bond d is ta n c e s and a n g le s . Standard d e v ia tio n s w e r e c a lc u la te d fo r a ll a to m ic p o s itio n s , bond d is ta n c e s and a n g le s . P o s it i o n a l and t h e r m a l p a r a m e t e r s along w ith th e ir a s s o c i a t e d sta n d a rd d e v ia tio n s a r e li s t e d in T able 9. The bond d is ta n c e s and a n g le s a r e p r e s e n t e d in T a b le 10. C a lc u la te d and o b s e r v e d s tr u c tu r e f a c to r s a re li s t e d in T a b le 11. The g e o m e t r y of str u c tu r e is sh ow n in F ig u r e 6. D e s c r ip tio n of the S tru ctu re The g e o m e t r y o f 5 -C gH g)('^7 -C g H q )R u 3 (CO)£) is show n in F ig u r e 6. T h e r e a r e tw o in depend en t (and e s s e n t i a l l y id en tical) m o l e c u l e s in th e unit c e ll, e a c h b i s e c t e d by a c r y s ta llo g r a p h ic m i r r o r p lan e. The Rug tr ia n g le h a s d im e n s io n s Ru ( l ) - R u (2) = 2. 8 3 5 8 and Ru (2)-R.u (2)' = 2. 853.8.. T he two c a r b o n y l grou p s on Ru (1) a r e a s y m m e t r i c a l l y b r i d g e d ^ ’ w ith Ru (1)-C (1) = 1. 8 6 8 , Ru (2)-C (1) = 2. 5 4 8 , and the an gle Ru (1 )-C ( l ) - O (1) = 160. 9° . T h e r e a r e two d istin c t CgHp lig a n d s in th e m o le c u l e , one b ic y c lic (VI) and th e o th er m o n o c y c li c (VII). 72 u > TA BLE 9 F inal A tom ic C oordinates for (n 5-C 8H9)(n7 -C 8H9)Ru3(CO)6 m o le c u le #1 m o lec u le #2 A tom X X z X X z Ru (1) 0 .1 3 3 9 1) 0. 00 a 0.4 7 0 6 (1) 0.3 9 4 3 (1) 0. 00 a 0.2 1 7 6 (1) Ru (2) 0 .1 3 0 3 0) 0. 1131 (1) 0.3 0 0 9 (1) 0. 3692 (0) 0. 1127 (1) 0 .0 3 7 8 (1) C 1) 0. 0775 6) 0. 1044 (11) 0.4 1 7 9 (9) 0. 3355 (6) 0. 1037 (10) 0. 1786 (9) 0 1) 0. 0384 4) 0. 1623 (8) 0.4041 (7) 0. 3002 (6) 0. 1600 (9) 0 .1 8 2 8 (7) C 2) 0 .1 2 0 4 6) 0. 2570 (13) 0. 3164 (10) 0. 3648 (5) 0. 2575 (10) 0. 0568 (9) O 2) 0. 1167 5) 0. 3456 (10) 0. 3302 (9) 0. 3665 (5) 0. 3457 (8) 0 .0 7 3 3 (8) C 3) 0 .2111 7) 0. 1285 (12) 0. 3822 (12) 0 .4 5 2 6 (6) 0. 1216 (9) 0 .0 9 1 9 (9) O 3) 0. 2593 5) • 0 .1 4 5 0 (9) 0 .4 2 4 0 (8) 0 .0 0 1 6 (4) 0. 3680 (7) 0 .1 1 4 7 (8) C 4) 0. 2703 10) 0 .5 0 0 0 a 0.4231 (14) 0 .4 9 4 3 (7) 0. 00 a 0.3 0 0 1 (14) c 5) 0 .2971 6) 0 .4 0 5 4 (15) 0 .4 0 5 6 (10) 0. 4710 (5) 0. 0916 (12) 0. 3287 (9) c 6) 0 .3 3 9 7 5) 0 .4 4 4 4 (11) 0 .3 7 2 5 (9) 0. 4362 (5) 0. 0545 (10) 0. 3775 (8) c 7) 0. 3821 7) 0. 3977 (13) 0. 3289 (ID 0.4 0 1 3 (6) 0. 0898 (11) 0 .4 3 2 8 (9) c 8) 0 .4 1 6 0 11) 0 .5 0 0 0 a 0. 3283 (17) 0. 3673 (9) 0. 00 a 0. 4416 (13) c 9) 0 .1 6 1 3 8) 0. 00 a 0. 1895 (13) 0. 1209 (10) 0. 5000 a 0 .0 9 7 0 (14) c 10) 0. 1355 6) 0. 1027 (10) 0. 1569 (9) 0. 1495 (6) 0. 3987 (11) 0 .1 2 3 2 (8) c 11) 0. 0785 12) 0. 1360 (23) 0.1381 (21) 0. 1982 (13) 0. 3829 (30) 0 .1 1 9 4 (21) c 12) 0 .0 3 9 9 6) 0. 1023 (13) 0. 1699 (12) 0.2 2 7 6 (7) 0 .4 0 3 4 (22) 0.0631 (16) c 13) 0 .0 3 0 8 8) 0. 00 a 0.2 0 4 0 (14) 0. 2320 (13) 0 .5 0 0 0 a 0. 0264 (27) c 14) 0. 0668 15) 0. 1134 (27) 0 .0 8 1 9 (25) 0. 2205 (15) 0. 3695 (33) 0 .1 6 1 6 (23) Note: a = value that is fixed by sy m m e tr y TABLE 9 (Continued) (A) M olecu le #1 A tom 104 ? u 104P 22 104? 3 3 104f l 2 10V l 3 ' ° 4f 2 3 Hu (1) 1 7 .4 (3) 106. 1 (14) 4 4 .4 (9) 0 .0 a 26. 8 (8) 0. 0 a Ru (2) 21. 2 (2) 8 4 .4 (9) 53. 8 (7) 16.9 (7) 35. 3 (6) 19. 2 (12) C (1) 28 (4) 62 (10) 50 (8) -26 (10) 41 (9) 6 (15) O (1) 29 (3) 91 (8) 86 (7) 27 (8) 55 (7) 23 (13) C (2) 24 (3) 82 (12) 57 (9) 17 (10) 39 (8) 46 (17) 0 (2) 37 (3) 83 (9) 113 (9) 1 9 (9 ) 63' (8) 18 (15) C (3) 25 (4) 95 (13) 95 (12) 9 (11) 61 (11) -24 (20) O (3) 19 (3) 132 (11) 110 (9) 1 (8) 30 (7) -30 (15) C (4) 24 (6) 239 (38) 28 (12) ' 0 .-a 5.(13) 0 a C (5) 19 (3) 192 (21) 49 (9) -45 (13) 31 (9) -33 (21) C (6) 23 (3) 104 (12) 36 (8) -22 (9) 16 (8) -37 (14) C (7) 36 (4) 116 (15) 73 (11) -28 (12) 70 (11) -72 (20) C (8) 35 (6) 109 (21) 98 (18) 0 a 83 (17) 0 a C (9) 30 (5) 76 (16) 53 (12) 0 a 54. (13) 0 a C (10) 30 (4) 76 (11) 56 (9) 11 (10) 54 (9) 8 (16) C (11) 25 (6) 73 (23) 18 (20) -20 (16) -5 (20) 13 (35) C (12) 21 (3) 99 (14) 99 (12) -19 (11) 27 (10) -80 (22) C (13) 11 (4) 215 (36) 47 (13) 0 (0) -1 (ID 0 (0) C (14) 30 (7) 68 (27) 39 (24) -3 (21) 4 (25) 23 (45) Note: a = value that is fixed by s y m m e tr y -j U1 TABLE 9 (Continued) (B) M olecu le #2 A tom * ^ ^ 1 1 l o 4 ? 22 1 0 4 P33 io4 P i 2 104 P i3 1 0 4 P 2 3 Ru (1) 1 3 .7 (3) 69. 3 (11) 45. 8 (8) 0 ,0 a 2 0 .7 (7) 0 .0 a Ru (2) 1 5 .7 (2) 4 4 .9 (6) 51. 3 (6) 3 .8 (6) 23. 1 (5) 3. 0 (10) C (1) 24 (3) 60 (10) 46 (8) 25 (9) 10 (8) 9 (14) O (1) 42 (3) 102 (9) 79 (7) 76 (9) 70 (8) 46 (13) C (2) 21 (3) 50 (10) 63 (9) 9 (8) 38 (8) 6 (15) O (2) 41 (3) 48 (7) 117 (9) 6 (8) 89 (9) -6 (13) C (3) 27 (4) 43 (8) 62 (9) 18 (9) 34 (9) 1 (14) O (3) 15 (2) 90 (9) 119 (9) 9 (6) 39 (7) 8 (13) C (4) ' 13 (4) 142 (23) 62 (14) 0 a 25 (12) 0 a C (5) 17 (3) 132 (15) 50 (8) -47 (11) 21 (8) -40 (18) C (6) 16 (3) 87 (10) 32 (7) -14 (7) 3 (7) -55 (12) C (8) 32 (5) 95 (18) 48 (12) 0 a 45 (13) 0 a C (9) 29 (5) 85 (17) 69 (14) 0 a 73 (14) 0 a C (10) 32 (4) 79 (12) 33 (7) 4 (10) 40 (8) -4 (14) C (11) -8 (7) 32 (17) 80 (20) 40 (20) -31 (18) 60 (38) C (12) 9 (3) 270 (37) 120 (18) 9 (17) 10 (12) -251 (42) C (13) 7 (5) 581 (42) 87 (25) 0 a -6 (16) 0 a C (14) -17 (9) 100 (20) 93 (24) 47 (23) -32 (21) 70 (45) Note: a = value that is fixed by sy m m e tr y -j o T A B L E 10 The B on d D is t a n c e s and A n g le s in < -1 8 h 9 )(i 7 - c 8h 9)R u 3 (c o )6 (A) B o n d D is t a n c e s (in a n g s tr o m s ) m o l e c u l e #1 m o le c u l e #2 R u th e n iu m -R u th e n iu m Ru ( l ) - R u (2) 2. 840 (2) 2. 831 (13) Ru (2 )-R u (2)' 2. 858 (2) 2. 847 (13) R u th en iu m - C arbon C arb onyl: Ru (1 )-C (1) 1. 850 (14) 1. 873 (14) Ru (2) -C (2) 1. 8 6 2 (16) 1. 858 (13) Ru (2)-C (3) 1. 880 (18) 1. 897 (16) Ru (2)-C (1) 2. 559 (15) 2. 531 (13) 1 5- C 8 H9 : Ru (1 )-C (4) 2. 257 (23) 2. 281 (20) Ru (1)-C (5) 2. 261 (16) 2. 257 (14) Ru (1)-C (6) 2. 233 (12) 2. 248 (10) Ru (1). . . C (7) 3. 383 (16) 3. 335 (13) Ru (1). . . C (8) 3. 5 3. 5 *7 7 - C 8 H9 : Ru (2 )-C (9) 2. 520 (16) 2. 529 (17) Ru (2)-C (10) 2. 173 (13) 2. 215 (12) Ru (2)-C (11) 2. 212 (24) 2. 209 (23) Ru (2) -C (12) 2. 287 (17) 2. 262 (20) Ru (2 )-C (13) 2. 706 (17) 2. 715 (31) Ru (2). • • C (14) 2. 952 (28) 2. 865 (26) 77 TA BLE 10 (Continued) m o le c u l e #1 m o le c u l e #2 C a r b o n -O x y g e n C ( l) - O (1) 1. 166 (19) 1. 150 (19) C (2 )-O (2) 1. 147 (20) 1. 138 (16) C (3)-O (3) 1. 123 (22) 1. 135 (13) C a r b o n -C a r b o n 1 5- C8H9 ; C (4)-C (5) 1 .4 4 3 (23) 1 .4 3 3 (19) C (5)-C (6) 1 .4 2 4 (21) 1 . 4 1 5 (19) C (6)-C (7) 1 .5 5 8 (22) 1 .5 2 4 (19) C (6)-C (6)' 1 .4 0 2 (19) 1. 370 (18) C (7)-C (8) 1. 545 (23) 1. 547 (20) 1 7 - C 8 H 9 : C (9)-C (10) 1 .4 4 2 (16) 1 . 4 3 4 ( 1 7 ) C (10)-C (11) 1 .3 8 3 (34) 1 .2 9 6 (29) C ( l l ) - C (12) 1 .3 0 0 (34) 1. 296 (31) C (12)-C (13) 1 .4 3 9 (18) 1. 363 (31) C (lO )'-C (14) 1 .6 2 5 (36) 1 .6 1 4 (27) C (1 2 )'-C (14) 1 .6 9 4 (36) 1 .6 3 4 (33) (B) B o n d A n g le s (in d e g r e e s ) R uthen iu m - Ruthen iu m - Ruthen iu m Ru (2 )-R u ( l ) - R u (2)' 6 0 . 5 (1) 6 0 . 4 (1) Ru ( l ) - R u (2 )-R u (2)' 59. 8 (1) 59. 8 (1) R u th e n iu m -R u th e n iu m -C a r b o n Ru ( l ) - R u (2 )-C (2) 1 1 0 . 0 ( 5 ) 1 1 1 . 3 ( 5 ) Ru ( l ) - R u (2)-C (3) 8 1 . 8 ( 6 ) 8 1 . 9 ( 5 ) Ru (2) - Ru (1 )-C (1) 6 2 . 0 ( 5 ) 6 l . 1 (5) 78 T A B L E 10 (Continued) m o le c u le #1 m o le c u l e #2 C a rb o n -R u th en iu m - C a rbon C ( l ) - R u (1 )-C (1)' 9 0 .9 (7) 8 9 . 3 (7) C (2 )-R u (2)-C (3) 8 9 . 3 ( 8 ) R uthen iu m - C arbon - Ruth e n i u m 89. 9 (7) Ru (1 )-C ( l ) - R u (2) 7 8 . 3 (6) 7 8 . 4 (6) R u th en iu m - C a r b o n -O x y g e n Ru (1)~C ( l ) - O (1) 162. 8 (12) 159. 0 (11) Ru (2 )-C ( 2 ) - 0 (2) 176. 9 (12) 174. 9 (12) Ru (2 )-C ( 3 ) - 0 (3) 173. 2 (14) 1 7 2 .6 (13) Ru (2)-C ( l ) - O (1) 1 1 9 .0 (11) 122. 9 (11) C a r b o n -C a r b o n -C a r b o n *7 5 - C 8H9 : C (5)-C (4)-C (5)' 1 1 1 .4 (9) 107. 7 (15) C (4)-C (5)-C (6) 104. 1 (16) 106. 6 (13) C (5 )-C (6 )-C (6)' 110. 2 (13) 109. 5 (11) C (5)-C (6)-C (7) 136. 3 (15) 139. 0 (14) C (6)*-C (6)-C (7) 112. 3 (12) 111. 8 (11) C (6 )-C (7 )-C (8) 98. 7 (14) 101. 3 (11) C (7) -C (8)-C (7)' 113. 3 (20) 108. 1 (16) 1 7 - C 8H 9 : C (lO )'-C (9)~C (10) 128. 4 (16) 126. 0 (19) C (9)-C (1 0 )-C (11) 127. 6 (18) 120. 9 (16) C (10)-C ( l l ) - C (12) 133. 5 (22) 141. 9 (22) C ( l l ) - C (1 2 )-C (13) 130. 9 (19) 126. 9 (25) C (1 2 )-C (1 3 )-C (1 2 )’ 128. 1 (17) 127. 0 (30) C (1 3 )-C (1 2 )'-C (14) 121. 3 (16) 131. 5 (24) C (1 2 )'-C (1 4 )-C (10)' 95. 9 (16) 97. 9 (16) C (14)-C (lO )'-C (9) 121. 1 (16) 129. 3 (16) 79 T A B L E 11 O b s e r v e d and C a lc u la te d S tr u c tu r e F a c t o r s The c o lu m n s d is p la y e d a re: h, 10 x F » and 10 x F c a lc . F o r e x a m p le , the f ir s t e n tr y sh o w s that, for the 12 O O r e fle c tio n , = 5 5 7 .4 , F caj c = - 5 2 1 . 4 . 80 1 1 I. t 1 6 777 -6 02 H C 0 I 4 1 789 1 585 12 935 955 1 12 5574- 52 1 4 10 1 987- 1615 1 1 4 1 3 3 3 1480 6 2565 3227 16 2766 2733 -8 31 02 3039 1 8 1 285- 1 351 - 1 0 I 828 I 675 20 1372- 1 1 74 -12 260 1- 2232 1 22 14 15 1158 -14 903- 1 085 ! 24 693 788 -I 6 1 959 19 18 - 18 1222 1 I 20 H 3 0 -20 1171- 1 096 1 -22 612 - 690 ' 2 3 780 6 38 -24 684 6 36 21 303 197 19 931- 1 02 0 H 1 3 0 1 5 1 150 1 056 i 3 72 2 850 7 439 546 11 1 0 69 -98 0 3 40 2 -305 7 10 3 1 1227 1 345 203 5 1 750 1 547 3 1 1 02 -955 H 3 1 H 2 0 - 3 1 232 160 3 -5 1095 924 6 392 -122 -7 1 137 -92 4 8 2201 1 972 -9 1 29 2- 1 1 83 -1 1 616 399 H I 0 -13 1 029 1119 -1 5 456 413 23 715 637 - 17 I 193- 1 0 94 1 9 1090- 1 1 36 -2 1 775 795 1 7 903 -796 -2 3 627 658 15 13 56 1231 i 13 2 05 4 5 3 H 2 1 1 1 1 €54- 1 942 9 19 24- 1 326 2 0 76 7 785 7 1095 540 16 1271- 1 2 55 1 4 527 -621 H I i 1 2 1 532 154 3 1 0 478 618 -9 212 370 8 1 846- 1915 ~I I 4 730 4 26 7 6 1 405- I 1 64 - 1 3 344 -264 4 2 74 9 2394 -15 30 16- 3014 -8 817 759 -17 44.7 451 -10 565 5 81 -19 1 356 1 257 -12 780 -8 53 -21 567 -535 -14 I 487- 14 98 -23 1 0 54 -950 - 1 6 469 563 - 18 1 142 10 22 H 0 1 -20 422 -4 74 -22 895 -905 22 13 70 1 183 -24 326 141 20 540 624 18 7 52 -82 4 H 1 1 -13 1673 1636 2 3 114 7- 1 088 -IS 149 7 I 3 96 19 1181 1 04 9 - 1 7 123 7- 12 06 17 645 -514 -19 389 -8 10 15 1 263- I 30 8 -21 1 024 1058 1 3 1 167 1428 -23 971 87 7 1 1 1226 90 0 9 3837- 3 2 95 H 4 1 7 15 13- 1 74 0 5 2278 2533 22 72 I -67 6 20 72 3 6 95 H 4 1 1 3 764 800 1 6 1310- 134 6 2 2 862 2348 1 4 196 8- 1874 0 32 7 3- 2839 1 2 1 765 16 52 -2 2937- 3026 10 2397 2388 - 4 1 820 1679 8 2955- 2703 -6 255 439 6 3522- 361 4 -3 14 35- 147 1 4 3225 35 35 -12 1 498 1 251 -14 1 091- 1 006 H 1 2 0 — 16 1 347- 1 285 - 1 8 590 6 99 8 427 -2 50 -20 648 62 4 6 31 1 -2 6 4 -22 1148- I 078 2 .31 4 5 1 -24 752 — 664 H 1 1 ■ w J H 3 I 1 1 362 -3 46 21 1 10 7- 1 0 1 t 17 1115 1 1 C C H 10 0 1 5 9C5 76 0 t 3 '1-667- 1 60 5 16 693 520 1 1 84 1 -'716 12 1118- 1077 9 887. 697 8 155 4 1 62 3 7 12 15 1 141 4 2271- 2298 5 1 244 959 2 313 98 1 1 3 35 1513 0 2324 2402 H 5 1 H 9 0 15 1 1 19 I I 73 IS 55 7 521 1 3 1 668— 1 865 1 3 352 3 5 7 1 1 1 3 67- 1 262 1 1 342 -209 9 2432 2 29 5 9 4 85 -424 7 1302 S 4 76 7 356 -4 36 5 13 5 7- 1 58 1 5 43 3 477 3 647 -66 2 3 387 1 30 1 24 3 7 254 2 1 56 3 -54 5 - 1 2 46 -4 - 3 3 4 3 8- 2690 H 8 0 — 5 812 610 - 7 1771 1 698 1 8 t>3 6 -56 0 - 9 1224- i 354 16 1219 1284 - 1 1 1 1 67- 10 26 1 4 74 3 641 8a 1 2 21 30- 2044 4 1931 1987 ilO 255 -320 2 556 164 8 32 4 0 3290 4 37 79- 3808 H 12 0 2 345 1 12 0 51 95 St 34 10 481 444 H 7 0 H 5 1 19 811 -725 17 I 590 1563 17 493 -430 1 9 512 -516 15 605 639 21 1368- 1246 1 3 659 389 , 1 1 931 -947 H 6 1 9 1 1 68 -94 4 i 7 498 320 -22 923 -913 5 272 231 -20 357 292 : '' 1 3 16 -263 -18 691 721 - 16 323 -355 H 6 0 - 14 34 3 -372 -12 391 5 38 20 770 70 1 -10 76 0 7 19 16 498 538 -8 275 -4 04 1 6 600 -546 -6 502 4 78 1 4 854 -8 33 -4 785 885 12 690 50 1 -2 915- 1000 10 10 16 1 058 0 1 525- 1 385 6 578 -746 2 1 5 39 I 43 1 4 57 I 621 4 1244 1214 6 i 580- I 5 56 H -c 0 a 2 326- 21 31 10 1 772 1638 21 400 1 65 12 1513 1 3 20 19 973- 1021 14 966 -794 17 4 04 -280 16 974 -849 1 5 85 3 809 18 645 521 1 3 876 714 20 485 492 1 1 1504- 1 2 98 9 934- 1012 H 7 1 7 1 261 1560 5 1115 855 -19 359 2 86 3 2 42 -123 1 7 284 1 50 1 201 95 -15 886- 1006 - 13 322 388 H 4 0 -1 1 I 38 5 1473 -9 316 -336 22 8 0'4 -766 -7 1 4 56- 1557 20 1171. 1 1 59 -3 1291 1 357 18 1269 1214 1 2476- 24 64 16 17 6 6- 1 786 3 287 -229 14 1825- I 562 5 1 052 10 29 12 25 49 2295 9 812 -693 10 1 633 1 643 1 1 31 6 1 04 8 2251- 2219 13 454 3 08 6 1 2 50- 1 245 1 5 5 87 -382 I 1 9 560 357 -13 3 1 6 269 -1 1 714 621 H 8 1 -7 685 -6 01 -3 932 969 -20 538 -433 - 1 329 73 -1 3 620 548 1 737 -6 93 - 16 1 167 1 036 3 273 -63 -14 406 -462 5 62 1 654 - 1 2 1 329- 1 196 1 3 306 - 181 -10 37 7 1 66 — 8 1241 1 1 53 H I? 1 -6 2 72 8 -4 1251- 1 134 -1 2 345 1 63 -2 814 803 -4 361 379 0 1 1 32 1 00 2 -2 571 -568 6 322 443 0 631 -626 8 3 68 -252 2 386 3 1 5 10 350 -526 4 398 4 85 12 384 393 6 383 -469 14 4 97 540 8 68 3 -743 16 4 35 -31 1 10 362 439 1 3 358 -420 H 13 1 H 9 1 - r 729 789 -19 1 020 1 046 -5 329 - 1 3 -15 18 31- 1 768 -3 974 -932 - 1 I 2 319 2 33 7 -1 459 276 -7 29 I 3- 2910 1 890 927 -3 3674 359 1 3 49 8 -4181 - 1 335 -149 5 859 -825 1 3253- 3331 5 2659 2 714 H ' 0 2 7 3 72 -542 9 1 092- 1 902 -2 2 1906 1774 1 1 332 784 -13 2334- 2355 1 3 3 06 819 -16 351 35 7 15 949 -91 3 -14 4860 4662 1 7 37 7 - 474 -12 519 -348 -10 541 3- 5499 H 10 1 - 8 26 1 562 6 4068- 3073 — 16 557 70 2 8 1536 1058 - 1 4 348 -449 I 0 28 3 665 -1 2 8 96 — 1017 12 781 -938 1 -10 279 - 1 35 14 54 1 -340 — 8 7 67 86 1 I 6 1 544 1428 -4 698 -695 18 35 9 -4 29 0 465 443 20 127 3- 1095 8 369 -286 I 2 3 72 4 04 H 1 2 , | H 1 1 1 -2 3 1171- I 1 83 ' -21 678 641 - 1 5 543 -35 2 — i 3 1707 16 3 5 82 I 17 I 325- 1 1 80 1 3 1285- 1398 -20 6 83 — 6 96 15 2049- 20 5 3 15 91 8 940 - 18 413 75 H 9 2 13 770 892 1 7 888 89 1 - 1 6 721 680 1 1 281 1 2629 19 433 -537 - 14 484 616 -19 1 156 1131 -9 13 26- 1 127 - 12 10 12- 1 007 -17 309 -343 -7 1 590- 1 81 6 H 4 2 -10 1 422- 1417 -15 168 3- 1667 ■ 3 10 33 1 261 -8 462 436 -11 1593 1658 5 9 02 786 -24 699 689 -6 237 292 -13 515 476| 7 20 19- 199 2 -22 405 -459 -2 653 -68 3 -9 254 -266 9 673 906 -20 898 -927 0 344 -262 -7 1495- 14 17 i 1 1930 1 642 - 16 1 102 1107 2 2 52 131 -5 379 8961 1 3 701 -473 -1 2 I 5 56- 1507 4 444 527 -3 1666 1599' 1 5 1 066- 1 205 - 10 24 1 18 6 1213 1 255 -1 1004 -905 1 7 417 503 -a 1 1 86 860 10 1 085- 1 192 1 1018- 1041 19 14 19 1 2 33 -6 279 370 14 639 683 3 72 8 8Q5i -4 534 -757 18 960 -952 5 29 2 i9s; H 2 2 -2 947 1 176 20 3 I I -155 7 1343- 13311 0 681 -653 9 329 -3S0l 22 6 1 1 44 7 2 2415- 25 07 H 7 2 1 1 1397 1 3511 20 570 -51 7 4 227 436 1 5 963 -905 18 1022- 1034 6 2406 2 140 -21 347 41 6 1 6 814 91 1 a 888 -735 - 19 699 555 H 10 2 1 4 1710 1 560 1 0 2109- 20 52 - 1 7 306 -337 \ I 2 1 0 76 -981 12 4 75 331 - 1 5 564 -465 -16 34 8 337 1 0 1394- 1299 1 4 1 975 18 26 -1 1 471 473 -14 1021 868] -8 10 83 893 16 322 -283 -7 368 -133 -10 686 — 6 54 | -6 16/3 1 757 18 1 32 7- 1 182 -5 249 -300 -8 29 1 20 1 1 2 1930- 1 680 - 1 3 70 428 -6 10 1 3 9 401 4 263 -4 09 H 5 2 1 942 76 9 -2 753 -77 2| 6 361 -21 7 3 869 -827 0 326 61 10 10 60 -848 -23 992 1 000 5 1115 -985 2 382 422! 1 2 3 85 -5 14 -2 1 634 665 9 1 300 1145 4 282 -242 1 4 1 054 1026 - 19 1273- 12 38 1 1 256 229 6 342 -375| 1 6 e l 6 657 -17 303 1 68 13 770 -5 93 10 35 7 -128' 1 8 796 -687 -15 2 308 2242 19 321 330 1 2 464 -574 20 644 -64 0 -13 775 -739 14 41 7 31 I 22 643 514 -1 1 2677- 27 19 H 8 2 | — 9 1929 2046 H 1 1 2 H 3 2 -7 3082 2972 -20 409 — 23 5 1 1 -5 3167- 3208 - 18 1 167- I 191 -15 388 -2131 23 539 554 -3 4155- 3889 - 16 3 35 313 -5 39 2 -2 77 21 677 6i a -1 4 52 6 4 0 98 -14 1 7 03 1 91 6 -3 280 -210 1 9 1 039 -940 1 3886 3931 - 10 21 32- 2115 - 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I 0 928 -978 12 738 774! 1 4 5 76 5 75 H 5 7 . -23 921 -930, -21 1011 1063, -19 1 458 1523 -17 906 -901 -15 I 33 7- 15 06 -13 996 1 00 1 -1 1 1066 1001 -9 1429- 1 335 -7 599 -59 7 -5 1556 1519 -3 479 -588 -1 190 1 - 1901 1 799 812 3 1560 1622 5 1 127- 1 200 7 1 39 6- 14 15 9 1047 1207 1 I 1 359 1401 i 3 563 -625 1 5 983- 1 029 H 6 7 I -24 504 575 -20 504 -482 -18 30 1 353 -16 390 247 -8 555 -550 -6 1181- 1088 — 4 154 3 1449 -2 10 1 2 925 0 134 6- 13 37, 2 l 149- 1 021 4 14 46 1 409' 6 1 26 8 1 232 I 88 I 8 972 -3 35 10 8 77 -898 1 2 567 548 1 4 550 414 H 7 7 2 I 4 84 -554 1 9 460 490 I 7 1 060 I 149 15 504 -610 I 3 1563- 1 608 1 1 478 484 -9 1357 1462 ~7 558 -503 — K 1 8 89- 1 886 - r 1262 1 165 i 250 -107 3 701 -733 5 355 1 29 7 41"9 325 9 465 -170 13 391 259 H 8 7 20 5 22 -52 0 18 683 -657 1 4 698 709 10 €38 -531 -8 3 29 224 -6 4 50 510 — 4 29 € 1 51 6 350 182 1 0 501 -367 H 9 7 19 383 -118 1 7 1 579 1585 1 3 20 €2- 2069 1 I 288 1 0 1 -9 2877 2695 - 5 2 598- 2550 -3 4 79 540 - 1 2224 2158 1 681 -639 3 1 637- 1 703 5 591 64 5 7 880 890 9 847 -781 H 1 0 7 1 6 39 4 320 -14 660 663 -12 30 3 -1 56 -10 439 -539 -6 664 690 -2 38 6 -393 0 34 5 1 10 6 30 2 25 H 1 1 7 - 1 3 53 I -553 -9 739 708 -5 49 1 -50 5 - i 602 5 37 H 12 7 -8 347 -4 17 -4 426 388 -2 372 400 H 0 8 -24 1260- 1 . 3 86 -2.0 2 179 2.1 19 -16 3060- 31 24 - 1 4 97 3 9 1 7 -12 391 1 3956 -10 398 -5 12 -8 3787- 3564 -6 1203 1034 0 2868- 2961 4 669 7 1 6 6 795 -892 8 765 — 778 10 814 94 8 14 65 1 -653 H 1 8 -23 809 -7 82 -21 125 l- 1 30 3 -19 894 897 - 17 1 44 1 1 3 50 -15 I 0 C 7 -969 -13 1 420- 1620 -1 1 437 626 -9 I 499 1400 -7 860 -869 -S 520 -399 -3 608 5 34 1 857 -9 2 4 3 268 - 1 28 5 1 I 76 1 0 32 7 369 -205 9 706 -74 8 I 1 329 550 1 3 765 71 C 15 460 -259 H 2 3 -24 690 -61 5 -22 422 514 -20 999 97 1 -18 646 -694 - 16 1063- 1 052 -14 914 869 -12 1 292 1 260 -10 705 -795 -8 1 529- 1 446 -6 254 104 -4 448 554 4 5 65 -619 8 6 72 615 10 351 216 12 610 -692 14 3 75 -246 H 3 9 -21 1 023 965 -17 8 1 2 -76 7 -15 1 406 1 35,7 - 1 3 1 421 1 42 7 - I I 1961- 2050 -9 1940- I 879 -7 33 37 3 298 -5 1 389 1475 -3 2 26 6- 247 1 - 1 2048- 2 1 24 1 2428 256 1 3 1 490 1 636 5 1552- 1711 7 657 -675 9 1192 1 254 1 1 5 79 61 5 1 3 60 3 — 56 8 M 4 8 -22 1 0 SO 1 C27 -20 392 -24 7 -18 907- I 123 -14 61 1 594 -12 564 — 560 -10 922 -89 1 -8 350 245 -6 531 -519 1 790- 1 792 0 159 9 1605 2 567 -502 4 1252- 1361 6 57 1 60 7 8 14 76 1449 10 454 -444 12 1 09 4- 110 7 H 5 8 -21 1228 1 2 34 -19 39 8 -5 04 - 17 1215- 12 3 6 -15 1503 149 2 -13 14 86 1607 -1 1 1840- 1 930 — 9 1 975- 1882 -7 3162 3059 -5 2 152 2168 -3 2762- 2850 -1 1944- 1 931 1 2743 2792 3 1631 1689 5 2220- 2266 7 1080- 1113 9 1425 1517 1 1 479 440 1 3 84 9 -879 H 6 8 -22 699 678 -18 71 1 -7 80 -14 400 3 35 -10 40 4 -292 -4 506 -407 -2 359 497 0 547 539 4 681 -828 8 84 0 8 78 12 653 -72 5 H 7 8 -21 410 -34 8 -17 508 450 -1 3 43 6 -397 — Q 279 205 — 7 356 62 — 5 34 5 193 — 3 407 -493 - 1 41 6 -2 75 3 61 7 4 75 7 658 -558 8: 9 H 8 8 - 12 2 102 2092 -a 955 -880 -20 1097 I 164 -6 1047 91 1 -18 422 -358 -2 906 -997 -16 1366- 1472 0 369 -364 -1 2 1623 1 603 4 48 0 436 - 8 1 7 69— 1 722 6 1 95 7- 1981 -6 4 40 42 8 1 0 1 587 1 589 -4 1 724 1717 -2 36 9 -309 H 1 9 0 1165- 1 I 98 2 4 77 335 -23 82 I 776 4 506 495 -21 809 -836 6 60 2 -506 -19 1018- 10 17 -1 7 1001 10C7 H 9 8 -15 1014 1067 -13 651 -650 — 19 4 78 409 -1 1 370 -2 19 - 17 1 1 05 1 203 -7 54 7 -506 -13 1 049- 1 057 -1 584 -570 -1 1 381 260 1 84 6 -898 -9 8 50 864 5 981 836 -7 549 -559 7 329 380 -5 823 -84 7 9 846 -803 -3 536 573 1 1 457 -4C6 -1 33 3 289 1 3 812 8 76 1 701 -625 C 740 727 H 2 9 7 421 1 1 -18 359 193 H 10 8 -lb 356 -298 -14 907 -9 1 1 -1 6 833 -778 -12 241 -2 16 -14 314 300 - 10 1525 1373 -1 2 787 796 -8 418 4 70 -10 327 -257 — 6 1144- 113 5 -8 852 -854 -4 642 -655 — 4 747 83 3 -2 731 712 0 545 -63 6 0 615 738 4 464 -459 H 1 1 8 8 427 396 -1 1 296 -255 H 3 9 - 9 343 41 -7 445 428 -23 481 524 -3 373 -181 -21 437 -536 1 365 274 -1 9 739 -668 -17 580 5 36 H 0 9 -15 338 3 O S -13 364 -326 -24 1236- 1 362 - 1 I 400 -462 -22 665 705 -7 £56 -112 -20 I 597 1 578 -5 560 624 -18 3 30 -358 — 3 1036 917 -16 14 68- 1571 - 1 292 364 1 7 72 -826 2 1329- 1329 3 333 388 4 78 7 -757, 5 938 82 8 6 76 9 827 9 870 -830 3 459 415 I 3 6 57 63 2 10 49 2 -52 6' H 4 9 H 7 9 -24 1 3 27 1 355 -21 52 8 — 468 -22 707 -82 1 -19 340 -5 76! -20 1 772- 1717 -15 472 588; -18 155 7 1470 -13 32 2 -1 59, -16 1685 1 844 -1 1 32 3 -312! - 1 4 2107- 2219 1 460 -567! - 1 2 26 1 8- 2580 5 601 767 -10 2995 2 874 9 507 -543 -8 1 933 I 926 i -6 3505- 3329 H 8 9 1 -4 1 864- 1 8 59 ! -2 24 78 2 53 6 -20 94 6 964; 0 1669 1 678 -1 8 34 8 -160! 2 2 42 3- 2 47 7 -16 842 -926 4 1 062- 1 213 -12 86 8 84 8' 6 1 7 53 190 6 - 10 359 -286 8 578 33 7 -8 522 -529, 10 1 268- 1 253 -6 546 531 -4 491 3 54 H 5 9 -2 558 -4 86- 2 887 894! -23 304 2 7,0 6 1038- 10 16 -21 352 -403 f -15 381 2 56 H 9 9 | - 1 3 2 83 -23 i -7 5 85 -624 -17 4 14 4 321 — 5 496 564 -9 384 210; - 3 1 1 62 1 1 43 -7 313 2 85, 1 784 -84 1 1 446 -3821 3 298 230 5 508 503 5 957 1 04 3 9 685 - 735 H 10 9 H 6 9 -14 346 155 - 1 2 499 5 19 -22 384 -269 -8 308 -271 -20 627 -653 -6 30 9 190! - 18 1 128 1 096 -2 378 -316 -16 9 89 1117 2 531 489 - 14 1 28 6- I 267 - 1 2 1060- 1 046 H 0 10 -10 1 601 1 558 -8 10 76 966 -24 512 -523 — 6 19 12- I 858 -2 0 898 892 -4 1 288- 1 26 7 -14 470 507 -2 1 S 30 1610 -12 562 -543 0 1 085 1 052 -10 170 7- 1619 90 -8 340 41 1 -5 1795 1792 -6 1 834 1 808 -3 933 871 - 2 14 02-1553 - 1 1480-1460 0 6 70 771 1 432 -6 27 2 1 742 1 702 3 972 98 1 6 1413-1349 5 370 345 10 1462 1 392 7 769 -7 1 3 I I 39 0 2.3 6 H 1 10 H 4 1 0 23 10 £6 1 043 19 1340-■1363 -24 312 -2 72 17 459 -417 -22 884 -896 15 9 74 1001 -18 I 049 989 -1 3 332 323 - 14 1 0 02- 1051 1 1 1 093 -985 -12 264 1 81 -9 451 376 -10 849 827 -5 591 -680 -2 380 -3 35 — 3 4 94 -452 0 337 - 1 76 - 1 897 929 2 579 5 16 1 358 499 6 391 -398 3 14 35- 1 431 8 381 -210 5 323 -238 7 1 300 I 32 7 H 5 1 0 9 396 275 1 1 1291- 1 173 -23 916 -9 16 -21 1405 1354 H 2 10 - 19 1255 1286 - i 7 1 842- 18 75 24 493 -51 5 -15 1 734- I 7 96 22 310 -268 -13 2033 2C44 20 465 518 - 1 1 I 477 14 56 I 4 447 42 3 -9 2673- 25 0 0 12 361 -197 -7 1221- 12 35 1 0 1010 -999 -5 2 184 2 187 -8 4 15 477 -3 1 355 13 06 -6 1396 1 307 -1 1895- 18 34 -4 333 -254 1 71 7 -759 - 2 I 429- I 517 3 1 452 I 510 0 3 56 24 7 5 305 345 2 1471 1 443 7 1 046- 1064 6 1135-1075 10 94 9 89 1 H 6 10 H 3 I 0 - 18 36 3 346 * -14 576 -660 23 707 -743 -10 34 9 228 21 1358 1388 -8 3 17 237 1 9 826 920 — 6 452 500 IT 17 59- I 857 -2 369 - 426 15 1 198- 1 155 0 336 242 13 2067 2081 2 571 695 1 1 1 7 60 1715 6 461 -471 -9 2552- 2398 - 7 982- 1010 H 7 1 0 -2 1 81 8 -84 7 -21 4 12 214 -1 7 1353 1425 -17 437 -38 9 -15 53 6 -582 -13 352 392 -13 2 0 0 3 - 1 993 3 477 -431 -1 1 649 672 7 662 498 240 0 2340 -7 4 18 -306 H 8 10 -5 2380- 2376 -3 716 667 -18 330 127 -1 21 76 2093 -1 6 3 46 -173 1 659 -646 -10 560 -570 3 1 834- 1 709 -8 277 1 38 5 365 380 -6 80 7 849 7 1 466 1407 -2 1 0 37- 1 045 9 395 -324 0 319 1 35 2 1 080 110C H 2 1 1 H 9 10 -2 4 6 65 642 -22 293 -256 - 1 5 830 775 -20 94 3 -975 -11 434 -40 1 -1 6 887 898 -9 3 33 328 -12 70 7 -676 -5 649 -609 -10 330 -297 -3 3 08 -328 -8 337 471 -1 85 1 778 -4 450 -261 3 I 1 3o- 1 094 -2 295 155 4 38 2 352 H IC 1 0 6 468 474 * 8 456 -439 - 1 0 606 -606 -6 7 70 72 1 H 3 1 1 -2 1 022 -967 -2 1 77 7 769 H 0 1 1 -19 31 1 3291 -17 702 -737' -22 999- 1 073 -15 38 1 — 278 j -20 331 -35 1 -13 483 445 -18 1 I 40 1135 -I 1 335 1 68| -14 855 -774 -9 374 -303 -12 433 4 32 -3 30 6 -89 - 1 0 1200 i 169 -1 444 464 -8 1 267- 1 165 1 416 3 38 — 6 551 -60 1 3 456 -254! -4 12 07 1 153 5 454 -4641 -2 785 705 9 489 276 0 1 724- 1 687 2 859 -779 H 4 1 1 4 15 37 161 7 6 756 729 -22 49 4 498' 8 1 514- 1 424 -20 156 9- 1602, -18 9 35 -938| M 1 I 1 -16 1632 1 725! -14 10 74 1012' -23 382 316 -12 184 3- 181 0i ( 91 -10 1099- 1 173 -2 314 328 - a 1 735 1 775 0 953 -884 - 6 336 759 2 363 -2 59 — 4 13 27- 1315 0 963 989 H 9 1 1 4 706 -700 6 4 19 307 - 13 1 223- 1123 8 415 386 -1 1 398 1 97 — 9 1 337 1330 M 5 1 1 -7 348 -303 — 5 1 427- 136 4 -21 853 84 8 - 1 i 322 1212 -19 338 266 -17 845 -863 H 0 I 2 — 1 3 1003 1 019 -1 1 356 3 18 -24 1 152- I 1 87 -9 586 -569 -20 1 847 1844 -5 350 377 -18 362 -278 1 394 273 -16 2529- 24 19 5 603 -61 0 - 12 299 3 2692 7 509 -379 - 1 0 892 -7 76 -8 3290- 30 75 H 6 1 1 — 6 60 3 551 -4 30 51 2880 -20 10 79- 1 072 -2 1205- 1 1 40 -18 5 14 -484 0 2191- 2004 -16 12 37 1316 2 1 128 1 070 — 14 700 652 4 1 708 1576 — 12 14 82- 1 500 6 1 020 -921 -1 0 397 -420 -8 10 32 1 0 52 H 1 12 . — 6 602 611 — 4 6 79 -725 -23 52 1 -569 -2 3 72 -22.9 -21 456 4 72 0 . 455 422 - 13 470 4 79 2 295 -215 -9 342 -3 68 6 374 246 -7 4 35 42 3 -3 729 -777 H 7 1 1 1 919 844 3 570 569 -17 522 388 5 81 1 -705 -1 3 6 64 -561 7 61 7 -60 5 -1 1 5 48 4 33 -9 10 00 10 12 H 2 1 2 -5 1 177- 1 1 26 -3 4 33 265 -2 0 632 679 - 1 9 16 97 0 - 1 8 536 — 508 3 751 -77 9 -16 1 129- 1 1 00 - 14 5 15 470 H ft 1 1 -12 1 474 1431 -10 370 -396 -1 4 445 -463 - a 1495- 1397 -10 369 235 - 6 474 42.4 -8 4 35 -514 -4 1 34 2 1 306 — 4 7 90 722 -2 292 -2 90 ( I 0 1 0 84 -976 -7 56 7 4 27 2 344 60 -1 532 -385 4 552 480 1 60 3 332 H 3 12 H 8 1 2 -23 825 -818 -14 485 271 -21 384 -244 -1 2 160 1 1561 -19 715 794 -1 0 567 -507 -15 5 74 -515 -8 1638- 1630 -1 1 122 29 2 — 6 30 1 288 -9 4 17 328 -4 1 335 1312 -7 341 - 1 66 -2 50 I -407 -5 2 83 1 51 - 1 460 -453 H 0 1 3 1 4 72 41 8 3 3 67 427 -22 581 620 -14 423 3 37 H 4 12 -6 54 4 -544 -2 616 4 72 -22 4 74 5 74 0 425 3 33 -20 953 -997 4 462 — 516 - i a 6 96 -618 -16 980 912 H 1 1 3 -14 7 49 693 -12 808 -76 4 -21 35 8 -229 -8 905 90 8 -19 1879- 18 75 -4 677 -683 -17 32 3 I 89 -2 5 85 545 -15 234 9 23 04 0 376 396 -13 576 -581 2 956- 1 006 -I 1 2677- 2562 4 78 3 -7 34 -9 102 I 94 9 — 7 2 690 2 596 M 5 ' 1.2 -5 619 -682 -3 1906- 1 786 -21 304 -258 -1 609 655 -19 781 81 7 1 1 130 963 -17 493 466 3 797 -661 -1 5 808 -73 3 - 1 3 391 -464 H 2 1 3 - - 1 1 480 433 1 - 9 428 275 -22 41 1 501 - t 381 -404 -20 442 238 . 3 5 1 2 5 0 4 -16 326 40 - 1 4 308 21 H 6 12 -10 424 256 — 6 579 -585 -1 8. ■ 356 -344 -2 715 663 -14 614 551 0 4 39 438 -10 42 0 -457 2 490 -434 2 436 - 4 4 2 4 517 - 4 32 H 7 12 H 3 1 3 -1 I 344 0 -21 536 - 5 3 3 ! 92 1 7 598 525 -7 10 92- 10 86 1 5 316 -2 18 -5 353 343 13 30 1 -369 -3 8 38 825 -7 4 34 -430 -1 760 -754 -3 451 382 1 989 — 896 -1 596 - 555 1 582 -608 H 6 1 3 3 50 8 465 -10 706 644 H 4 13 -8 447 444 -6 735 -606 1 6 367 412 -4 550 -4 79 1 4 653 -702 -2 829 6 84 1 2 359 -248 10 1 1 26 1 0 86 H 7 I 3 -8 7 7 7 620 -6 1072- 1 061 -1 5 880 870 -4 756 -743 -13 49 2 -4 20 -2 1248 1 253 -1 1 852 -823 0 719 651 -7 781 688 2 990- 10 1 1 -3 461 -522 H 5 13 H 0 1 4 1 9 564 553 - 1 8 1 68 9 159 1 17 590 542 -14 194 7- 1824 15 7 30 -685 -12 864 864 13 474 -401 -10 1823 1 724 1 1 886 927 -8 63 1 -627 -9 3 1 1 -28 3 -6 1553- 13 92 -2 741 535 -7 657 -644 0 713 -515 -5 14 27 1370 -3 667 612 H 1 14 — ! 1205- 1 1 09 -21 4 30 -31 2 H 4 14 -19 650 -695 -17 447 30 1 -18 419 -337 -15 534 528 -16 520 -486 - 1 1 413 -251 -14 543 493 -1 410 349 -10 68 3 -691 -6 986 896 H 2 14 -2 939 -8 55' -20 494 450 H 5 14 -18 7 0 7 705 j -16 513 -482 -1 5 654 -602' -14 790 -754 -13 1236 1 1 24i -12 4 48 384 -1 1 684 605 -10 690 650 -9 134 1- 124 9 -8 382 -26 3 -7 85 8 -784 -5 150 5 1399 H 3 14 -3 634 5 1 1 -19 3 74 366 H 6 14 ; -17 575 -565 -15 6 16 -6 3 I - 10 358 -4 1 0 -13 1 135 1021 t - 1 1 513 430 -9 1370-1281 ! i 93 The e v id e n c e fo r the fo r m u la tio n of the b ic y c lic CgH^ ligan d as (VI) is u n a m b ig u o u s. The u n sa tu r a te d p o rtio n of the m o le c u l e ^ c o r r e sp o n d in g to th e a to m s C (4), C (5), C (6), C (5)' , C (6)*^ is c o o r d in a te d to Ru (1) w ith m o le c u l a r p a r a m e t e r s e x p e c te d for a c y c lo p e n ta d ie n y l-ty p e lig a n d (R u-C d is ta n c e s in the ran ge 2. 23.8. - 2. 2 0 8 and C -C d is t a n c e s in the ra n g e 1. 378. - 1 . 4 4 8 ) , w h ile the a to m s in the s a tu r a te d p ortion of the ligan d a r e a ll n on -b on d in g to Ru (1) and a r e s e p a r a te d f r o m e a c h o th e r by ty p ic a l C -C s in g le bond d is ta n c e s o f 1. 5 2 8 - 1. 5 6 8 . The m o n o c y c lic CgHq lig a n d is d e c id e d ly n o n -p la n a r and c o o r d in a te s by w rap p in g it s e l f arou n d on e of the e d g e s of the Rug tr ia n g le . The unique m e th y le n e group in th is lig a n d is lo c a te d at one o f the "hinged" p o s it io n s . B e c a u s e o f the c r y s ta llo g r a p h ic m i r r o r p lan e w h ich b i s e c t s the Ru^ tr ia n g le , the m e th y le n e group is d is o r d e r e d o v e r both C (11) and C (14) p o s itio n s . T h us, both p o s itio n s a p p ea r s u p e r im p o s e d in e le c t r o n d e n s ity m a p s as an e x t r e m e l y e lo n g a te d r e g io n of e le c t r o n d en sity . F o rtu n a tely , it w a s p o s s ib le to r e s o l v e th is into two d istin ct h a lf - a t o m s by l e a s t - s q u a r e s r e fin e m e n t. The id e n tific a tio n o f the unique m e th y le n e group w a s a c c o m p lis h e d r e a d ily by ex a m in a tio n o f the m o le c u l a r p a r a m e t e r s : a c l o s e Ru (2)-C (11) d is ta n c e o f 2. 2 l 8 c h a r a c t e r i z e s C (11) as a CH group, w h ile a n o n -b o n d in g Ru (2)*. . . . C (14) d is ta n c e of 2. 9 l 8 id e n tifie s C (14) as th e Ch£ group. 94 D is c u s s i o n F o r m a t io n o f the te tr a h y d r o p e n ta le n y l ligan d (VI) in r e a c tio n s o f c y c lo o c t a t e t r a e n e w ith m e t a l c a r b o n y ls h a s b e e n o b s e r v e d p r e v io u s ly . ^^ A lthough c o m p le x e s of the m o n o c y c lic CgH^ lig a n d (VII) w ith one m e t a l a to m a r e known, ^ in R u gfC O jgfC gH ^ ^ w e h a v e the f ir s t e x a m p le of this lig a n d s e r v in g as a b r id g e b e tw e e n two m e t a l s . If, r e a s o n a b ly , ^3 one a ttrib u tes the n. m . r. s ig n a ls at 4. 73(2H ), 4. 82(1H), and 7 .4 6 (6 H ) p p m in the s p e c t r u m o f Rug (C O )^(CgH^)2 to the te tr a h y d r o p e n ta le n y l ligand, the r e m a in in g s ig n a ls | T 4 . 73(1H ), 5. 94(2H ), 6. 93t o f d (2H), 7 .4 6 (2 H ), 8. 5 0 m (lH ), and 8. 75(1H )^ d em a n d that a m i r r o r p lan e b i s e c t the m o n o c y c lic CgHg , w h ich is not ap p a ren t in the m o le c u l a r s tr u c tu r e e s t a b lis h e d h e r e . W h eth er s o m e lo w e n e r g y flu x io n a l p r o c e s s p r o d u c e s th is as a t i m e - a v e r a g e d e ffe c t is as yet u n d e te r m in e d . A t - 6 0 ° s o m e b r o a d en in g of the s ig n a ls at T 5. 94 and 6. 93 o c c u r s , but low s o lu b ility o f the c o m p le x h in d e r s the atta in m en t of lo w e r t e m p e r a tu re s p e c tr a . 41 44_4A C o n v e r s io n of CgH^ o r C g H jg to the b ic y c lic CgH^ te tr a h y d r o p e n ta le n y l lig a n d (VI) h a s b e e n o b s e r v e d p r e v io u s ly , the f o r m e r p r o c e s s in v o lv in g the addition of a h y d ro g en a to m and the la tte r the r e m o v a l o f th r e e h y d r o g e n a t o m s p er m o le c u l e o f r ea c ta n t h y d r o c a r b o n . The m e c h a n i s m s of t h e s e r e a c tio n s a r e 95 not c le a r , but it s e e m s p la u s ib le that c o m p o u n d s co n tain in g (VI) as a lig a n d cou ld be in t e r m e d ia t e s in the fo r m a tio n o f p e n ta le n e c o m p le x e s . 96 R E F E R E N C E S 1 W old b ye, F . , R e c . C h e m . P r o g . , 24, 197 (1963) 2 G illa r d , R. D. , in P r o g r . I n o r g . C h e m . , 7 _ , 215 (1966); C h e m . R e v s . , 6 5 , 603 (1965) 3 M a so n , S. F. , P r o c . C h e m . S o c . , 137 (1962) 4 D ennin g, R. G. , and T. S. P ip e r , Inorg. C h e m . , _5, 1056 (1966), T. S. P ip e r and A. G. K a r ip id e s , J. A m e r . C h e m . S o c. , 86, 5039 (1964) 5 Sugita, T. , and Y. Inouye, B u ll. C h e m . S o c . J a p . , 3 9 , 1075 (1966 ) 6 J a e g e r , F . , O p tic a l A c tiv ity and H igh T e m p e r a tu r e M e a s u r e m e n t , M c G r a w -H ill P u b lish ers', N e w Y ork, N. Y. (I960) 7 M ath ieu , J. P . , B u ll. S o c . C h im . F r a n c e , 3_, 476 (1936); C h im . P h y s . , 3 3 , 78 (1936) 8 S a ito , Y. , K. M ak atsu , M. S h iro , and H. K uroya, A c t a . C r y s t. , 7, 636 (1954); 8^ , 729 (1955); K. N a k a tsu , M. S h iro , Y. S aito, and H. K u roya, B u ll. C h e m . S o c . Japan. , 3 0 , 158, 795 (1957) 9 T e m p le to n , D. H. , A. Z alk in, and T. U ek, A cta. C r y s t . , 21_ (1966) A 1 5 4 (Supplem ent) 10 S aito, Y. , and H. Iw a sa k i in A d v a n c e s in the C h e m is t r y o f the C h e m is t r y of th e C o o rd in a tio n C o m p o u n d s. S. K ir s c h n e r , Ed. , The M a c m illa n Co. , N ew Y o rk (1961); B u ll. C h e m . S o c. Japan, 35, 1131 (1962) 11 M a so n , S. F . , and B. J. N o r m a n , Inorg. N u c l. C h e m . L e t t e r s , 3, 285 (1967) 12 j 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 M athieu , J. P . , A n n . P h y s . , 19 (1944) D a v iso n , A. , W. C. K r u s e ll, and R. C. M ic h a e ls o n , J. O r g a n o m e ta l. C h e m . , 7 2 , C7 (1974) F lo o d , T. C. , and D. L. M ile s , jJ. A m e r . C h e m . S o c . , 9 5 , 6460 (1973) A nd rian ou, K. A. , A. M a m ed o u , L. M. V olk ova, and E . I. K la b u n o v sk ii, Izv. A kad. N auk USSR, S e r . K h im . , (1969) 230 5. D a v is o n , A . , and D. L. R e g e r , L A m e r . C h e m . S o c . , 9 4 , 9237 (1972) D ay, V. W. , and A . D a v is o n , P e r s o n a l c o m m u n ic a tio n . D a v is o n , A. , and N . M a r tin e z , J. O r g a n o m e ta l. C h e m . , 74, C 17 (1974) B r u n n e r , H. , A n g e w . C h e m . Int. E d . , 1 0 , 249 (1971) B r u n n e r , H. , and E . S ch m id t, J. O r g a n o m e t a l. C h em . , 3 6 , C18 (1972) F lo o d , T. C. , F . J. D iSanti, and D. L. M ile s , C h e m . C o m m u n . , 336 (1975) B ijv o e t, J. M. , A. F . P e e r d e m a n , and A. J. van B o m m e l, N a tu r e, 168, 271 (1951) M a th ie s o n , A. M. , A c t a . C r y s t . , 9_, 317 (1956) P r e lo g , V. , H elv. C h im . A c t a . , 3 6 , 308 (1953) " T a b le s of I n te r a to m ic D is t a n c e s and C on figu ration in M o le c u le s and Ions: S u p p le m e n t 1 9 5 6 -1 9 5 9 , " S p e c ia l P u b lic a tio n # 1 8 , T he C h e m ic a l S o c ie ty , London (1965) J a c o b so n , S. E. , and A . W o jc ic k i, J. A m e r . C h em . S o c . , 9 5 , 6 9 6 2 (1973) Knox, S. A . R. , and F . G. A. Stone, A cco u n t C h em . R e s . , 1_, 321 (1974) 98 28 B a ir d , N. C. , and R. M, W est, J. A m e r , C h em . S o c . , 9 3 , 3072 (1971) 29 B lo c k , R. , R. A. M arty, and P . d eM ayo, _J. A m e r . C h e m . S o c . , 93_, 3071 (1971) 30 H afn er, K. , R,. D o n g e s, E. G o e d e c k e , and R. K a is e r , A ngew . C h e m . Int. Ed. E n gl. , 12 , 337 (1973) 31 Stone, F. G. A. , N a tu r e (London), 232, 534 (1971) 32 K atz, T. J. , and M. R o s e n b e r g e r , J. A m e r . C h e m . S o c . , 8 4 , 865 (1962); T. J. K atz, M. R o s e n b e r g e r , and R. K. O 'H a ra , ib id . , 86, 249 (1964) 33 K atz, T. J. , and J. J. M r o w c a , _J. A m e r . C h em . S o c . , 8 9 , 1105 (1967); T. J. K atz, and N. A cto n , ib id . , 9 4 , 3281 (1972); T. J. K atz, N. A cton , and J. M cG in n is, ib id . , 94, 6205 (1972) 34 C h u rc h ill, M. R. , and K. K. G. L in, I n o r g . C h e m . , 1 2 , 2274 (1973) 35 Cotton, F. A . , A . D a v iso n , T. J. M a r k s , and A . M u sc o , iL' A m e r . C h e m . S o c . , 9 1 , 6598 (1969) 36 B r u c e , M. I. , M. C ooke, and M. G r e e n , J. O r g a n o m e ta l. C h e m . , L3, 227 (1968) 37 H ow ard, J. A . K. , S. A. R. Knox, V. R ie r a , F. G. A. Stone, and P . W oodw ard, J. C. S ^ . C h e m . C o m m . , 726 (1973) 38 Bau, R. , J. C. B u rt, S. A . R. Knox, R. M. L a in e, R. P. P h illip s , and F . G. A . Stone, J. C. _S. C h e m . C o m m . , 726 (1973) 39 C otton, F. A. , B . A . F r e n z , and L. K r u c z y n sk i, _J. A m e r . C h e m . S o c . , 95, 951 (1973) 40 Chin, H. B . , and R. B au, J. A m er. C h e m . S o c . , 9 5 , 5068 (1973) 99 41 C o ffield , K. G. Ih rm an, and W. B u r n s , J. A m e r . C h e m . S o c . , 82, 4209 (I960) 4 2 S e e fo r e x a m p le : M. B r o o k h a r t, and E. R. D a v is , _J. A m e r . C h e m . S o c . , 9 2 , 7622 (1970); M. C ooke, P . T. D ra g g ett, M. G r e e n , B. F . G. Joh n son , J. L e w is , and D. J. 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Creator Chou, Chaw Kuo (author)

Core Title Absolute configuration determination of diasteriomeric iron complexes by X-ray diffraction

Degree Master of Science

Degree Program Chemistry

Publisher University of Southern California (original), University of Southern California. Libraries (digital)

Tag chemistry, analytical,OAI-PMH Harvest

Language English

Contributor Digitized by ProQuest (provenance)

Advisor Bau, Robert (committee chair), [illegible] (committee member), Reed, Christopher (committee member)

Permanent Link (DOI) https://doi.org/10.25549/usctheses-c17-796895

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Rights Chou, Chaw Kuo

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