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Determination of the crystal structure of 1, 5-diphenyltricyclo [2.1.O.O.²˒⁵] pent-3-yl p-bromobenzoate.. Gibbons, Cyril Stephen 1968

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T H E D E T E R M I N A T I O N O F T H E C R Y S T A L S T R U C T U R E O F 1 , 5 - D I P H E N Y L T R I C Y C L 0 [ 2 . 1 . 0 . 0 2 / 5 ] P E N T - 3 - Y L p - B R O M O B E N Z O A T E B Y X - R A Y D I F F R A C T I O N by CYRIL STEPHEN GIBBONS B . S c . (Hons.), M e m o r i a l U n i v e r s i t y o f Newfoundland, 1966. A THESIS SUBMITTED I N PARTIAL FULFILMENT OF THE REQUIREMENTS FOR THE DEGREE OF MASTER OF SCIENCE i n the Department o f C h e m i s t r y We a c c e p t t h i s t h e s i s as con f o r m i n g t o the r e q u i r e d s t a n d a r d . THE UNIVERSITY OF BRITISH COLUMBIA Ju n e , 1968 In p r e s e n t i n g t h i s t h e s i s i n p a r t i a l f u l f i l m e n t o f t h e r e q u i r e m e n t s f o r a n : a d v a n c e d d e g r e e a t t h e U n i v e r s i t y o f B r i t i s h C o l u m b i a , I a g r e e t h a t t h e L i b r a r y s h a l l make i t f r e e l y a v a i l a b l e f o r r e f e r e n c e and S t u d y . I f u r t h e r a g r e e t h a t p e r m i s s i o n f o r e x t e n s i v e c o p y i n g o f t h i s t h e s i s f o r s c h o l a r l y p u r p o s e s may be g r a n t e d b y t h e Head o f my D e p a r t m e n t o r b y h.ils r e p r e s e n t a t i v e s . I t i s u n d e r s t o o d t h a t c o p y i n g o r p u b l i c a t i o n o f t h i s t h e s i s f o r f i n a n c i a l g a i n s h a l l n o t be a l l o w e d w i t h o u t my w r i t t e n p e r m i s s i o n . D e p a r t m e n t o f C^WZ-MI S T g v The U n i v e r s i t y o f B r i t i s h C o l u m b i a V a n c o u v e r 8, C a n a d a - i i - ABSTRACT The c r y s t a l s t r u c t u r e o f 1 , 5 - d i p h e n y l t r i c y c l o [ 2 . 1 . 0 . 0 Jpent- 3 - y l p-bromobenzoate has been d e t e r m i n e d by X-ray d i f f r a c t i o n . The c r y s t a l s a r e t r i c l i n i c , a = 5 .92, b = 8.98, c = 17.85 A, d= 8 9 ° 1 7 ' , P = 8 2 % 6 ' , H = 89°50' , Z = 2, space group P i . The s t r u c t u r e was de t e r m i n e d w i t h v i s u a l Cu-K^ d a t a by heavy atom P a t t e r s o n and F o u r i e r methods, and the p o s i t i o n a l and t h e r m a l parameters were r e f i n e d by l e a s t - s q u a r e s , the f i n a l d i s c r e p a n c y i n d e x R, b e i n g 0.16 f o r 1228 observed r e f l e c t i o n s . The t r i c y c l o p e n t a n e system i s h i g h l y s t r a i n e d , w i t h s i x C-C-C a n g l e s o f 60°, t h r e e o f 80°, and f o u r o f 90°, and an i n t r a m o l e c u l a r non-bonded G...C d i s t a n c e o f 1.99 A. The C-C bond l e n g t h s are s i m i l a r t o those o f normal s i n g l e bonds, e x c e p t f o r the bond common t o the two three-membered r i n g s , w h i c h may p o s s i b l y be s l i g h t l y s h o r t e r t h a n the o t h e r s . - i i i - TABLE OF CONTENTS PAGE TITLE PAGE i ABSTRACT i i TABLE OF CONTENTS i i i LIST OF TABLES i v LIST OF FIGURES v ACKNOWLEDGMENTS v i INTRODUCTION 1 EXPERIMENTAL 3 STRUCTURE ANALYSIS 5 COORDINATES AND MOLECULAR DIMENSIONS 8 DISCUSSION 13 BIBLIOGRAPHY 15 APPENDIX I. TABLE OF OBSERVED AND CALCULATED STRUCTURE FACTORS 16 - i v - LIST OF TABLES TABLE PAGE I . F i n a l p o s i t i o n a l and i s o t r o p i c t h e r m a l parameters w i t h s t a n d a r d d e v i a t i o n s 9 I I . Bond d i s t a n c e s and a n g l e s w i t h s t a n d a r d d e v i a t i o n s 10 I I I . E q u a t i o n s o f mean p l a n e s and angles between p l a n e s 11 IV. Observed and c a l c u l a t e d s t r u c t u r e f a c t o r s . . . . . . 16 - V - LIST OF FIGURES FIGURE PAGE 1. S e c t i o n s o f the t h r e e - d i m e n s i o n a l e l e c t r o n d e n s i t y d i s t r i b u t i o n , and a drawing o f the mole c u l e 7 2. P a c k i n g o f the m o l e c u l e s i n the u n i t c e l l . . . . 12 - v i - ACKNOWLEDGMENTS I would l i k e t o expr e s s my a p p r e c i a t i o n f o r the guidance and encouragement g i v e n t o me by Dr. J . T r o t t e r d u r i n g the p r o g r e s s o f t h i s work. I a l s o want to thank Dr. S. Masamune f o r the c r y s t a l sample o f the t r i c y c l o p e n t a n e d e r i v a t i v e w h i c h he has p r o v i d e d . - 1 - INTRODUCTION I n r e c e n t y e a r s , p o l y h e d r a n e s have been the s u b j e c t o f much s t u d y by t h e o r e t i c i a n s , who have attempted t o i n t e r p r e t the n a t u r e o f bonding i n such compounds, as w e l l as by o r g a n i c c h e m i s t s , who have attempted t o s y n t h e s i z e them. One o f the f i r s t s u c c e s s f u l p r e p a r a t i o n s o f the t r i c y c l o - pentane system was c a r r i e d out by Masamune ( 1 ) , who by p h o t o l y s i s o f l , 2 - d i p h e n y l - 3 - d i a z o m e t h y l k e t o c y c l o p r o p e n e , o b t a i n e d as p r o d u c t l , 5 - d i p h e n y l t r i c y c l o [ 2 . 1 . 0 . 0 jpentanone-:3* ( I ) . T h i s p r o d u c t was i d e n t i f i e d on the b a s i s o f c h e m i c a l a n a l y s i s , i n f r a - r e d s p e c t r a , and n u c l e a r magnetic resonance. S h o r t l y t h e r e a f t e r , D o e r i n g and Pomerantz ( 3 ) , u s i n g a copper c a t a l y s t i n s t e a d o f p h o t o l y s i s , p r e p a r e d the d i m e t h y l analogue, w h i c h was c h a r a c t e r i z e d by the same methods. However, t h e y c a s t doubt on the s t r u c t u r e o f t h e i r compound as w e l l as Masamune's by s u g g e s t i n g an a l t e r n a t i v e s t r u c t u r e ( I I ) w h i c h c o u l d f i t the d a t a e q u a l l y w e l l . The i n f o r m a t i o n a v a i l a b l e a t t h a t time was i n s u f f i c i e n t t o d i s t i n g u i s h between the two. R R R R 0 0 1 I I R = Ph,Me. The name f i r s t used f o r t h i s compound, ^ - , 5 - d i p h e n y l - t r i c y c l o [ l . l . l . 0 4 ' ' 5 ] p e n t a n o n e - 2 , i s r a t h e r a r b i t r a r i l y based on the view t h a t the compound i s d e r i v e d from b i c y c l o [ l . 1.1] pentane. However, Meinwald and C r a n d a l l (2) have p o i n t e d out t h a t a c c o r d i n g ,to I.U.P.A.C. r u l e s , the r i n g system s h o u l d be named as i t appears i n the t e x t above. - 2 - The i n t e r p r e t a t i o n o f s p e c t r a c o u l d n o t be c a r r i e d out s a t i s f a c t o r i l y , nor c o u l d the u n u s u a l c h e m i c a l p r o p e r t i e s o f t h i s compound be e x p l a i n e d w i t h o u t f i r s t r e s o l v i n g t h i s c o n t r o v e r s y . T h e r e f o r e an X-ray s t r u c t u r e a n a l y s i s o f a heavy atom d e r i v a t i v e , 1 , 5 - d i p h e n y l t r i c y c l o [2.1.0.0 < 5 ] p e n t - 3 - y l p-bromobenzoate ( I I I ) was u n d e r t a k e n t o r e s o l v e t h i s d i f f i c u l t y , and t o o b t a i n d e t a i l s o f the geometry o f the r i n g system. p-Br.C^H^.CO.O I I I - 3 - EXPERIMENTAL C r y s t a l s o f 1 , 5 - d i p h e n y l t r i c y c l o [ 2 . 1 . 0 . 0 ' ] p e n t - 3 - y l p-bromobenzoate ( I I I ) are c o l o r l e s s p l a t e s e l o n g a t e d along a, w i t h (001) d e v e l o p e d , and s m a l l e r (010) f a c e s . The d e n s i t y was measured by f l o t a t i o n i n aqueous p o t a s s i u m i o d i d e , and the u n i t c e l l d i m e n s i o n s were d e t e r m i n e d from r o t a t i o n , W e i s s e n b e r g , and p r e c e s s i o n photographs.. C r y s t a l Data ( X j C u - K ^ = 1.5^18 A; A,Mo-Ka = O.7IO7 A ) . 1 , 5 - D i p h e n y l t r i c y c l o [ 2 . 1 . 0 . 0 ' ] p e n t - 3 - y l p-bromobenzoate, G 2 i + H l 7 B r 0 2 ' m o l # w t * = l + 1 7 * 3 ' m , P * = 1 3 9 ° « T r i c l i n i c , a = 5.92, b = 8.98, c = 17.85 A, <*=89°17», £ = 8 2 ° M S ' , / = 8 9 ° 5 0 ' . Volume o f u n i t c e l l , JJ = 9I+1.3 A 3. D (Z = 2) = 1 A 7 g.cm. - 3. D = 1 A 3 g.cm." 3. —m A b s o r p t i o n c o e f f i c i e n t f o r Cu-K^ X - r a y s , X= 1.5ifl8 A, = 3l+. 6m." 1. A b s o r p t i o n c o e f f i c i e n t f o r Mo-K^ X - r a y s , ' v = O . 7 I O 7 A, -1 x = = i ( X - - - — S ~ 7 /*= 23 cm. T o t a l number o f e l e c t r o n s p e r u n i t c e l l , F(000) = k2h. No absent r e f l e c t i o n s . Space group i s P I (C-^ 1) o r P l ( C i 1 ) ; P I from s t r u c t u r e a n a l y s i s . The i n t e n s i t i e s o f the r e f l e c t i o n s were r e c o r d e d w i t h Cu-K :^ r a d i a t i o n ( N i f i l t e r ) on h k l e q u i - i n c l i n a t i o n Weissenberg f i l m s ( h = 0 — 5 ) , and e s t i m a t e d v i s u a l l y u s i n g the m u l t i p l e f i l m t e c h n i q u e . The l a y e r s were s c a l e d , and the d a t a - h - supplemented from hOi and hkO p r e c e s s i o n f i l m s (Mo-K^•;- Zr f i l t e r ) . The c r y s t a l used had c r o s s - s e c t i o n 0.19 x 0.13 mm., and no a b s o r p t i o n c o r r e c t i o n was made. L o r e n t z and p o l a r i z a t i o n f a c t o r s were a p p l i e d , and the s t r u c t u r e a m p l i t u d e s were d e r i v e d f o r the 1228 observed r e f l e c t i o n s . - 5 - STRUCTURE ANALYSIS The bromine atom pos i t i o n was determined from the three-dimensional Patterson function, and structure factors were calculated for a l l r e f l e c t i o n s using the scattering factors for Br from the International Tables (h) and assigning a temperature factor, B, of ^-.0 A (R = 0 .53). A three- dimensional Fourier series was summed with the signs of the structure amplitudes based on the contribution from the bromine atom only. A l l the carbon and oxygen atoms i n the molecule were located on the resu l t i n g electron density map, which could be interpreted on the basis of space group PI. The structure factors for a l l 27 atoms were calculated (R = °2 0.32), setting B = ^ . 0 A for a l l atoms and using the C and 0 scattering factors from the International Tables (*f). The p o s i t i o n a l and thermal parameters and an o v e r a l l scale factor were refined by block-diagonal least-squares methods, with minimization o f Z w ( F 0 - F Q ) ^ , where V w = 1 when |F 0| 4 F , and V w = F /|F 0| when |F Q| > F . F was i n i t i a l l y taken as 20. For the 257 unobserved r e f l e c t i o n s F 0 was taken as 0.6 F(min.) and ^fw as 1.0. Seven cycles of least-squares reduced R to 0.172, and an analysis of 2 * the values of w(F„ - F ) suggested that F should be changed to 8. Three further cycles with anisotropic thermal parameters completed the refinement, the maximum s h i f t i n the p o s i t i o n a l parameters being 0.2<r for the f i n a l cycle. The f i n a l value of the discrepancy index, R, was 0.157 for the 1228 r e f l e c t  ions. The f i n a l FQ and F c values calculated from the output parameters of the tenth cycle are l i s t e d i n Table IV (Appendix I ) . A f i n a l three-dimensional Fourier series was summed, and sections of the resulting electron density d i s t r i b u t i o n are shown i h Figure 1, together with a drawing of the molecule showing the atom numbering system used. A f i n a l difference map showed no s i g n i f i c a n t spurious d e t a i l , the maximum °-3 fluctuations being + 1 e A , except i n the v i c i n i t y of the i °-3 bromine atom, where fluctuations of + U e A were observed. 0 I 2 3 4 5A I 1 1 i ' i Figure 1. Sections of the three-dimensional electron density^ d i s t r i b u t i o n (contours at in t e r v a l s of 2,3,H-...eA" at carbon and oxygen, and 2,3,^,5,10,20,30 eA" 3at bromine), and a drawing of the molecule. - 8 - COORDINATES AND MOLECULAR DIMENSIONS The f i n a l p o s i t i o n a l and thermal parameters are given i n Table I. x, y_ and z are the coordinates referred to the t r i c l i n i c c r y s t a l axes, and the mean standard deviations o of the coordinates ( i n A) were calculated from the l e a s t - squares residuals. B values are the iso t r o p i c temperature factors from the seventh least-squares cycle. Since the v i s u a l Intensity data are of li m i t e d accuracy ( i n comparison with counter methods), the detailed values of the anisotropic temperature factors probably have l i t t l e physical s i g n i f i c a n c e , so they are not l i s t e d and w i l l not be discussed. The bond distances and valency angles i n the molecule are l i s t e d i n Table I I . The standard deviation for bonds i s approximately 0.05 A, and for angles i s approximately 3 . Equations of the mean planes through the three phenyl rings and the carboxyl group are given i n Table I I I , together with several selected planes through the tricyclopentane system and the interplanar angles. The packing of the molecules i n the unit c e l l i s shown i n Figure 2. - 9 - TABLE I 3 F i n a l p o s i t i o n a l ( f r a c t i o n a l x 10 ) and i s o t r o p i c t h e r m a l o p (A ) pa r a m e t e r s . Mean s t a n d a r d d e v i a t i o n s are o~ (x) = c r ( y ) = cr (z ) =0.004-1 f o r B r , 0.024- A f o r 0 , 0 .038 A f o r C ; <5"(B J = 0 . 1 A 2 f o r B r , 0 .5 A 2 f o r 0, 0 .8 A 2 f o r C . Atom X Z z B C ( l ) 357 4-26 706 k.7 C(2) 158 4-07 769 5.2 C(3) 313 kok 830 k.k c(4-) 1+67 4-93 770 k.5 c(5) 255 558 74-0 k.7 c (6) 293 161 888 5.2 C(7) I87 705 718 4-.6 C(8) 003 725 681 5.0 C(9) -061+ 867 657 6.2 C(10) 074- 991 672 6.6 C U D 258 968 709 6.3 C(12) 316 830 730 4-.6 C U 3 ) 4-20 366 630 4-.1 CU4-) 275 379 578 6.3 C U 5 ) 327 315 506 7.2 C U 6 ) 534- 237 4-92 7-1 C U 7 ) 675 222 54-2 7 . 9 C(18) 628 287 615 6.9 C U 9 ) 4-18 019 899 4.8 C(20) 303 -093 94-0 5.3 C(21) 4-20 -219 950 5.4- C(22) 64-4- -24-2 916 h.9 C ( 2 3 ) 75k -131+ 87^ k.7 C(2h) 651 002 865 k.7 0(25) 102 188 914- 5-5 0(26) 4-18 262 8t+2 5.3 Br (27) 795.9 -4-23.0 929.6 6 . 6 - 10 - TABLE II o Bond distances (<r = ca. 0.05 A) and valency angles (°~ Tricyclopentane system C(2)-C(3) = 1.50 C(3)-C0f) = 1.54- C(2)-C(5) = 1.53 C(l)-C ( 2 ) = 1.54- c O O - c ( 5 ) = 1.53 c ( i ) - o v 4 - ) = 1.52 Mean = 1.53 C(l)-C ( 5 ) = 1.4-4 C(2)...C(4-) = 1.99 0(2: -C(3) -c (40 = 8 I . 7 c(3: -C(40 -c ( 5 ) 89.3 c o : -c (40 - C C D 92.2 c o : >-C(2) -c ( 5 ) 90.8 c o : -C(2) - C C D = 92.9 dk: )-c(5) -C(2) = 81.3 c(k: -C(l) -C(2) 81.4- c(5: >-c(4-: -C(l) 56.3 c( 5 : >-C(2) - c ( l ) = 56.1 c(i+: >-c(53 - C C D = 61.4- C(h] ) - c ( i : -c ( 5 ) = 62.3 C(2] )-o(5) -C(l) = 62.3 0(2: >-c( i : -c ( 5 ) — 61.6 C(2] ) - c o : -0(26) = 115 - c ( 3 : -0(26) = 109 External angles at C(l) and C(5) = 134-.4--142.1 (six angles), mean 138° Substltuent groups C(3)-0(26) = 1.4-5 0(26)-C(6) = 1.37 C(6)-0(25) = 1.19 C(6)-C(19) = 1.50 C(5)-C(7) = 1.4-5 C(l)-C(13) = 1.4-7 Br(27)-C(22)=1.88 Aromatic rings C-C = 1.30-1.44 (18 bonds), Mean 138 Angles at C = 117-123 (26 angles), mean 120. C(3)-0(26)-C(6) = 117.3 0(26)-C(6)-0(25)= 121.1 0(26)-C(6)-C(19)= 112.9 0(25)-C(6)-C(19)= 125.9 - 11 - TABLE I I I Equations of mean planes and angles between planes. Equations of mean planes i n the form jbc1 + ml' + nZ' + a = 0, o where x;1, Y1 , Z' are coordinates i n A referred to orthogonal axes a*,b^c . Plane Atoms L m a E. Maximum Dis p l . A 7 12 -0.1+59 0.136 0.878 10.790 0.017 B 13 18 0.*+22 0.838 -0.3M-6 0.66^+ 0.005 G 19 2h 0.1+36 0.367 0.822 15.17^ 0.022 D 6,19,25,26 o.Wf 0.396 0.803 1*+. 935 0.01*+ E 2,3,lf -0.361+ 0.855 0.369 7.335 0 F 1^,5 -OA99 -0.561 0.661 if. 173 0 G 1,2,5 0.736 -0.022 O.677 11.09*+ 0 Angles between planes. Planes Angle F-G 85° E-F 87 E-G 88 A-F 1+3 A-G 75 B-F 25 B-G 87 Figure 2. Packing of the molecules i n the unit c e l l . - 13 - DISCUSSION The c r y s t a l a n a l y s i s has c o n f i r m e d the f o r m u l a t i o n o f the compound as a d e r i v a t i v e o f t r i c y e l o [ 2 . 1 . 0 . 0 ' J p e n t a n e . The l a c k o f a c c u r a c y i n the bond l e n g t h s and a n g l e s i s due t o ( i ) the l i m i t e d a c c u r a c y o f e s t i m a t i n g the i n t e n s i t y d a t a v i s u a l l y , ( i i ) the p r e s e n c e o f the r e l a t i v e l y heavy b romine a tom, a n d , ( t o a l e s s e r e x t e n t ) , ( i i i ) p o s s i b l e a b s o r p t i o n e r r o r s . However , the geometry o f the r i n g sys tem i s now known, and some o b s e r v a t i o n s about bond l e n g t h s and a n g l e s c a n be made. The g r e a t s t r a i n i n the t r i c y c l o p e n t a n e sy s t em i s i n d i c a t e d by the v a l e n c y a n g l e s g i v e n i n T a b l e I I , t h e r e b e i n g s i x C - C - C a n g l e s o f about 60°, t h r e e o f : about 80°, and f o u r o f abou t 90°. The bond d i s t a n c e s , however , do n o t appear t o be g r e a t l y i n f l u e n c e d by the s t r a i n . S i x o f the C-C d i s t a n c e s a o are i n the range o f 1.50 - 1.5^ A , mean v a l u e 1.53 A ( s t a n d a r d o d e v i a t i o n o f the mean = 0.02 A ) , c l o s e t o the n o r m a l s i n g l e bond l e n g t h (5)» The bond w h i c h i s common t o the two t h r e e - o membered r i n g s , C ( l ) - C(5)» measures l.hh + 0 .05 A , so t h a t t h i s bond does seem t o be s h o r t e n e d s l i g h t l y , a l t h o u g h the d i f f e r e n c e from the o t h e r bonds ( 0 . 0 9 A = l.otf") canno t be c l a i m e d t o be d e f i n i t e l y s t a t i s t i c a l l y s i g n i f i c a n t . The C ( 2 ) : . . C(M-) non-bonded d i s t a n c e i s o n l y 1.99 A . The bond d i s t a n c e s i n the a r o m a t i c r i n g s are i n the o o range 1 .30 - l.hh A , mean 1 .38 A . The r o o t - m e a n - s q u a r e d e v i a t i o n o f the l e n g t h s from the mean v a l u e , 0.0k A , i s c l o s e t o the s t a n d a r d d e v i a t i o n computed from the l e a s t - s q u a r e s - 14- - equations, in d i c a t i n g that the estimations of the accuracy are reasonable. The valency angles at the aromatic carbons vary from 117 - 123°, with a mean value of 120°. The dimen- O O sions of the carboxyl group, C=0 = 1.19 A, C—0 = 1.37 A, C—C=0 = 125.9°, C — C —0 = 112.9°, 0—C=0 = 121.1°, are o normal (5), and the C—Br distance (1.88 A) i s close to the usual value (5)« Each of the aromatic rings i s planar (Table I I I ) , and the carboxyl group i s planar and, within experimental error i t i s coplanar with the aromatic ring to which i t i s bonded. The orientations of the C^H^ rings are quite s i m i l a r (Table I I I ) , each being approximately at r i g h t angles to the plane C(l)—C ( 2 )—G ( 5 ) , but are not quite i d e n t i c a l , and are probably influenced by intermolecular interactions. S i m i l a r l y the exact arrangement of the p-bromobenzoyl group probably depends on the c r y s t a l packing forces, and the two external angles at C(3) appear to d i f f e r s l i g h t l y (110 and 116°). The intermolecular distances correspond to van der Waals o interactions. The shortest C . . .0 contacts are 3.36 and 3.4-1 A, and the shortest C...C and C... Br distances are 3.60 and 3.73 A, respectively. - 15 - BIBLIOGRAPHY 1. S. Masamune, J . Am. Chem. S o c , 86, 735 (196*+). 2. J . Meinwald and J . K. Crandall, J . Am. Chem. S o c , 88, 1292 (1966). 3. W. von E. Doering and M. Pomerantz, Tetr. Lett., (196*+) 961. h. "International Tables for X-ray Crystallography", Kynoch Press, Birmingham, 1962, v o l . I I I . 5. "Tables of Interatomic Distances and Configuration i n Molecules and Ions", Chem. Soc. Special Publ., No. 11, 1958 and No. 18, I965. - 16 - APPENDIX I Table IV Observed and Calculated Structure Factors (Negative F values indicate an unobserved r e f l e c t i o n . ) - 17 - TABLE IV h k 1 F F 0 n - * 27.2 30.5 i at . i i i 0 12 26.* 30.1 n - l 7 1(1,1 - a . ? 0 69.7 52.1 1 5 * 17.7 - l b . 3 -2 1 3 8.2 11.1 D n 0 0 0 0 • fl 0 0 0 D 0 ,_Q [ 0 0 c ) 1 70.5 70.2 3 Z I_2 U . . 4 - 3 8.9 9.5 0 0 - 0 0 - 0 ft - 5 9.6 12. 5 *0.2 -27 . 6 * 3 . 6 39. b 7.3 - 6 . 7 - 1 . * 2. i 1 19.0 l b . 1 9 * 2 6 9 0 J 6 0 0 1 7 2 * . . 0 13 11.1 13.0 0 -13 6 . 6 -7.7 0 1* - * . 0 3.9 0 - 1 * - * . l -1.2 0 15 6 . 9 10.* 1 O.^LS LZ.2 9-3 - - -1 22 1 21 1 -2 2 81 -2 9 2 -2 3 17 - 3 16 3 *1 3 10 L -i 13 * *3 * 7 5 -2 -5 26 s - •> 2 -23.8 9 25.4 3 6 . 0 5 -61.1 9 -9 .5 a 5 .0 . . 4 6 .6 7 -18.6 4 IB.3 3 39.5 3 -12.1 4 10.0 — 2 5 * . B 1 36.0 b -9 .0 7 - * . 3 * 2b.2 7 l . * - 5 * 9.8 -13.2 5 4 14.0 14.7 5 5 B.I -6 .5 5 -5 25.B 19.9 5 5 10.0 -17.8 2 2 --2 2 2 - * * * .8 -41.8 1 4 5.5 - * . T 1 4 3.7 7.7 1 5 -2.1 4 . 0 i -5 24.8 -21.9 * 29.3 -29.1 5 135.* - 101 . * 6 60.3 - 5 * . * 7 46.9 -45.0 H Z3..1_-25.1 _ 9 39.0 -3* .3 J 10 10.2 - 8 . * > 11 -1 .5 1.9 12 15.1 IS.6 13 16.7 l b . * 1* 17.fc 17.B 15 5.3 5 .2 0 0 - 0 0 - 0 n - 0 - 0 0 - 0 ft - 0 0 0 0 - 0 - D—--_ 0 ' 0 - 0 0 - 0 _ 0 ___ 0 0 - 0 0 - 0 - 0— - 0 o - 0 0 - 0 S -1 .5 0. 8 8.1 6. 9 -1 .6 1. 9 * ,6 * . 10 15.6 -16. In la •> IK 11 22.5 - 2 * . 11 12.6 9. 12 9.* -10. 12 9.5 6 . 13 -1 .8 2. _.J_t 5 J . 5 _ - 0 16 12.3 -15.1 0 -16 17.3 1*.6 0 17 7.1 -11.3 0 -17 12.0 6.7 D 18 6.9 -11.3 D__rJ_B h.b 5.5 . 1 0 30.h - *6 .7 1 0 70.1 S l .B 1 • 1 I**.* -11* .7 1 -1 *9.1 - *9 .5 1 1 39.6 39.5 1 L 13__ T1_B_.*_ - - 5 6 -3 .6 2 .4 5 -6 -3 .7 - 0 . 4 5 6 15.6 -29.9 5 6 -3 .6 -8 .0 5 7 6.1 -6.2 5 7 12.3 -24 . * 5 7 22.6 -22.8 5 B 15.5 17.7 5 -8 6 . 5 9.1 5 8 28.3 -28.5 5 9 30.6 7(1. <1 -2 '2 2 2 - -2 2 2 - -2 2 2 .——5 ^ ft -1 -2B -.1 1 5 4 .1 -6.8 1 b 6.8 6.8 1 -b 4 . 5 - J . T 1 6 52.2 - *7 .6 1 6 36.5 -3* .6 1 7 6.1 =fl.6_ 1 -T -2 .9 1.2 1 T 2b.0 -26.7 1 7 75.7 -60.5 1 6 6.6 - B . T -6 IT.5 -17 . * 0 0 0 0 - 0 - 0 D - 0 . - 0-. 16 5 . * 5 . * 0 *6.7 - *6 .6 1 31.2 -22.0 1 1.0 -0 .3 2 -2J,.6.. .r?l .7 . 2 9.8 10.7 3 7.0 * . * 3 7.1 - 9 . * * 138.8 -117 .9 * 5b.9 51.1 5 J L . 3 . -59.3. . I* 10.3 -12.3 0 45.5 « 0 . 8 1 18.1 19.* 1 41.u 37.* 2 2 . i 3 .* __2. _ ?\. 7 ??_ 1 _, 1. - 13.7 15.9 100.1 -113.1 7.7 12.0 8.5 -12 . * 106.2 97.6 - 5 20 6 1* -6 28 6 15 6 27 -—7. - J M -7 7 T 5 7 22 8 21 -8 -3 2 -22.3 9 1*.9 0 . 31.2 0 -16.7 6 -26.6 fl 41-3 * 10. B 0 -10.3 7 -25.B 1 25.* 3 6.0 5 - 5 5 1 5 -1 5 1 9 -4 .0 -1.2 9 6.7 - 9 . 4 0 16.5 1*.6 0 6.9 -7.1 0 9-7 -13.2 -2 2 2 2 - 2 2 2 - -2 2 7 . 1 - 1 1 1 _=J 8 24.7 -23.1 9 *3.3 -28.3 9 - 3 . 4 0.5 9 lb .9 -17.3 4 A - i d 3 2*.0 - 2 * . 3 27.6 23. * *6.0 - M . * 2 * . ; n. 5 *9 .3 - * 3 . ? 7 3 1 5 5 50.3 *6.5 63.2 -66.0 139.9 125.6 3*.6 -38.0 31.B 28.5 ..110.2 - 9fl.B_. 13*.3 107.0 36.3 - 3 * . * 3.5 3.5 5.3 -10.8 69.7 60.2 - - - 5 -1 5 I 5 1 5 -I 1 5 I 1 7.0 -12.1 1 - 4 . 2 -5.6 2 12.2 11.2 2 7.1 -10.6 ? - * . ? 7.ft 0 20.0 25.2 0 5.5 -3.B 0 14.7 -16.2 1 10.1 -10.6 1 15.6 l9.B-_ 0 0 - 0 0 -ft 5 20.0 16.9 6 38.0 35.8 6 62.3 *5.6 7 23.9 27.* 7 68.0 *6.5 fl 75. 9 — . I 5 5-. 6 32.9 - 3 * . 6 11.3 - 9 . 7 9.6 - 9 . 7 15.2 -13 . 8 6.8 - 7 . . . _ - . . ._ f l . l __;Zi. 9 7.0 10. 9 22.5 -16. 10 7.2 9. 10 12.9 - 11 . 11 13.2 16. _ — a in. 8 17 9 16 -9 5 9 17 9 * J -IHr* * -17,7 7 17.6 9 6.5 8 -20.0 H 1.7 } 1 b b b 6 - 6 - i •> 3 '.1 10.2 0 -3 .7 - 0 - * 0 -3 .7 - 2 . * 1 15.0 1*.8 1 10.7 -9 .6 1 A . 1 -R. f. 2 - -2 2 2 2 - -7 1 11 -3 .5 5.3 I 11 -3 .0 4 . 7 1 12 -3 .7 5 .4 1 -12 16.3 22.9 1 12 10.7 10.1 17 tft.l 7fl.S 0 - 0 0 - 0 0 - . 0 J 0 - 0 0 - 0 0 - 6 20.6 21.* 9 43.3 *2.0 • 9 18.* 17.* 10 13.3 16.7 10 - 1 . * 1.5 - j j 9.i . ic.a. 11 18.1 - 1 * . B 12 8.5 -8 .0 12 27.2 -20.0 13 12.* - 11 . b 13 32.9 - 2 b . 5 14 - l k 7 1 3.. . 2 ' 5 - - > _ _ 30.3 28.2 * . l -6 .6 18.* 21.1 29.3 29.* 1.4 -ft.9 , - - * j 0 8 0 6 0 10 0 -3 1 6 I A 3 9 . * 2 -7 .0 3 -15.1 7 3.8 2 -6 .0 5 - l f l .5 _ 1 -3 .7 -7.3 2 2*.6 20.2 2 6.2 -5.2 2 -3 .7 * .3 2 15.2 -I*.2 \ 14 ft 10 * 2 2 - 2 2 - 2 ? - 1 13 11.3 -11.3 1 13 11.3 10.5 1 1* 11.7 8.B 1 1* 6.6 T.7 15 T.O 5.3 15 17.1 17.9 _0 0 0 0 0 n - i 1_ 1 1 1 L2__ U-J 5 . * 6. 7.5 6. 26.6 - 21 . 8.3 - 8 . -11- 1 b 3 D 3 - 5 9 9 7 35.2 -37.3 11.J -11.0 38.3 35.9 1*.6 -16.2 * .9 5.1 1 6 1 -3 2 6 3 9 3 -7 .2 9 -1 .5 5 - 5 . r 1 -1.1 6 -9 .7 ft • -H 7 - 6 6 6 - 3 27.5 -21.2 3 10.8 19.9 3 22.6 -20.8 4 29.5 2B.* * 32.7 -28.0 2 2 2 2 - 2 16 12.2 9 . * IT 6.9 7.9 2 0 *3.2 -41.T 2 0 19.6 -19.5 2 1 15.1 -13.1 0 - 0 0 0 0 - n I* 3*.3 -27.3 15 3.1 -2 .0 16- 15.8 -13.1 17 9.7 -8.2 0 1.3 1.2 1 l7 n 17.A 0 0 - 0 0 - 0 8.* -11 . 15.1 -15. 3.8 * . 11.8 -10 . 3.9 * . * .H -6 . - 1 -1 l 3*.2 33.5 18.0 -20.1 29.B 33.0 31.7 - 3 1 . * 17.9 16.9 71.4 -7 * .7 * 9 * 10 5 7 6 7 7 6 ft 7* 9 -9 .0 0 -11.3 1 -3.7 1 - b . 1 9 -b .9 6 6 - -6 6 4 20.2 -20.7 5 11.1 11.7 5 28.5 -21.3 5 9.1 20.3 6 I t . i 17.8 2 - -2 2 2 2 - ~ 2 2 2 - -2 2 2 - -2 2 2 2 - 2 1 43.0 -43.5 2 1 4 -37.6 2 2 15.5 -18.7 2 -2 17.0 15.6 2 15.6 -16.2 0 - 0 0 - D 0 -_ _ — 0 - 0 0 - 0 0 - n 1 68.* 6*.3 2 26.2 28.7 2 80.9 -80.7 3 66.0 59.0 3 17.3 -16.6 t tii,,) t l •> 0 0 - 0 0 * 0 6.8 7.0 2.6 0.9 9.0 9.0 12.5 9.3 12.T 12.6 77.0 11. n 10 31.9 30.7 11 1*.0 -11.2 -11 1*.8 13.* 11 2D.7 - 2 1 . * 11 10.* 12.7 17 7A.ft - 7 * . 1 - 0 83 1 21 1 36 1 *6 1 8* 7 71 * -69.1 7 18.6 4 31.* 8 - * 7 . 4 1 -65.2 9 i 7. n - 6 6 6 6 1 6 1 1 6 L 7 7 7 - 7 7 - 1 1. T - 7 7 - 7 7 - 7 - 4 . 0 -1.1 8 16.7 - IB.7 9 17.0 -18.8 0 12-2 -14.6 1 12.3 -9.7 2 7.1 zfi.B_. 0 21.4 18.9 1 -4 . 1 3.4 1 -4 . 1 -0.9 2 20.3 -16.1 2 - 4 . 1 2.7 J 1J.6 rJ.1^1 _ 3 29.9 26.0 * 6.9 -6 .7 * 12.0 12.2 5 12.0 -10.3 > 7.0 7.6 3 53.9 - 5 3 . * 3 23.3 29.* 3 6.1 - * . l 3 - 2 . i -3 .7 * 57.S -50.7 4 *6 .0 - * * . 5 5 33.9 -35.6 5 38.* -39.1 6 33.5 - 2 6 . * 6 33.7 -29.7 7 IS * - l 7 .A 0 0 - 0 0 - 0 n - 8 19.3 19.1 8 3*.6 2* . * 9 17.1 16.7 9 23.8 17.0 10 * .3 5.9 in 9.7 «J.5 - 12 27.7 26.3 13 11.2 -13.3 13 11.6 12.9 1* l l . » - 15 . * 1* - * .2 * . l 15 7.1 -7.2 —- 1 * 2 11 2 23 3 37 3 27 •K -J 8 -6.3 5 -15.5 7 -28.5 2 31.1 7 27.9 9 * . 7 * 6.5 12-* * -2 .5 -2.1 5 2*.0 -2* .2 5 38.5 *5.5 5 4 . 0 3.6 0 - 0 0 - 0 0 - 7 b . i -3.1 8 38.6 -3H.1 8 12.2 8.3 9 17.7 - 1 7 . * 9 M . 7 30.* in ?* .7 -76.fl 0 0 - 0 0 - 0 f) - 11 4.4 -7.5 11 3.1 3 . 5 12 * . * -5.2 12 9.7 -B .5 13 13.2 -13.9 13 9 .5 lb 7.1 -5 .9 2 0 111.3 76.8 2 0 55.5 - *5 .2 2 1 31.1 30.5 2 -1 10.0 -8 .6 I.. ._l 5 5 . S _ _ W .4 . _ 2 1 7.1 -6.8 2 2 18.9 23.0 -2 121.2 78.9 2 58.0 -50.2 2 60.2 52.8 1 -3 6 .2 9.1 2 3 70.6 -68.1 2 3 27.B 32.6 2 * 15.B 15.7 2 - * 12.2 16.8 ? * mh.n -51.3 I -2 * -2 * 39 * 27 * -3 5 ! J 9 6.1 9 -1 .6 b -32.3 9 36.2 0 -0 .3 4 -13.9 2 2 2 - -2 2 _ 2 . . 2 - -2 2 2 2 - 2 6 3b.8 -33 .4 2 -6 -2 .9 3.6 2 6 37.1 33.6 2 6 8.3 9.4 2 7 6.0 9.1 2—=J . . _ 5 . 2 _ - l l . l _ 7 39.9 33.7 T 6.9 12-* B 42.5 40.5 -8 5.5 -11 .4 8 30.1 22.8 0 - 0 0 - 0 0 - n 10 15.2 11.* 11 20.3 - IB.7 11 8.3 8.7 12 6.7 -5.8 12 10.0 7.3 11 1 t T .» 0 0 0 0 0 - 0 - 0 0 - 0 0 - n 1* 5.1 -8.6 15 2.8 -3 .0 0 29.5 26.0 1 9.3 6.9 1 16.6 16.8 _-2 7.2 7-..<>_ 2 12.8 -12.9 3 21.1 21.1 3 12.9 -11.9 * 5.2 * 16.9 -16 . * 5 1 A. l - i n 5 21 5 12 5 22 6 16 6 19 ft to 1 -20.2 5 20.8 8 27.3 7 -19.1 9 -17.8 7 7ft.1 -6 - * . 2 6.8 0 15.8 -15.5 1 22.* -22 . * -1 10.0 -9 .0 2 10.0 -10.9 -.2 7 . i _ -fc.5 3 7.1 9.1 B * - * . 3 1.9 5 7.1 4 .B 6 21.1 17.6 7 12.1 11.2 0 - 0 0 - 0 0 f> 13 7.1 5.1 1* 7.* 7.7 1* 7.* 5 . * 15 7.5 6.7 16 13.5 15.6 17 \\.\ W--K - - 6 30 7 -3 7 20 7 17 7 2* B J l , 9 )5.2 3 - 3 . J 8 -19.3 6 25.1 9 29.2 2 2 2 - - 2 . —2- . 2 2 - -2 2 2 - .-J — - '"-] 9 56.) 51.b 9 - J . 5 0.2 9 35.1 28.3 9 -3 .5 -0.5 0 - . - 4 f l . 4 _ 38. B— 0 6.8 -20 .4 0 - 3 . * 5.5 0 -3 .7 2.6 1 10.* 9.7 1 -3 .6 -5.5 1 - a5 .9 . - L 7 - l _ 2 -3 .8 0.1 2 15.6 - 1 7 . J 2 - * . l -3.7 3 - * . 0 4 . 6 3 16.3 -16.6 » A O -7 » 0 0 0 - 0 0 - 0 - 1 .0 -2.6 1 56.3 - * * . 7 3 1 30.1 - 2 1 . * 2 57.6 - *7 ,7 3 2 33.7 J 4 . 6 4 \ 4 7 f> -**.... 0 - 0 0 - 0 0 5 23.6 -16.9 6 3.0 -2 .5 6 9.7 -6.8 7 5.3 -3 .9 8 17.5 -19.3 _ — : 2 - 21.7 25.9 5.5 3.0 * .2 -7.2 6.8 -6.6 2*.5 26-7 - 8 26 8 10 8 18 9 1* 9 -3 3 -24.G 1 18.7 9 23.0 8 -15.3 8 -3 .9 3 1 105.8 -65.2 2 69.7 -42.1 -1 21.5 -20.3 -2 - 1 . 6 * . B 3 3 1*-4 -16.1 i - i a in t 0 - 0 0 - 0 0 - 3 3 62.7 5*.7 i * 59.6 -43.6 J * 33.6 23.2 J 5 13.9 -13.9 1 5 35.* 30.6 0 6 0 3.1 -3 .6 0 6 1 9.8 -6.* 0 8 2 -1 .9 0.3 0 8 3 5.* -3 .7 0 8 * 13.9 -16.2 1 6.3 -10.2 21.b 21.2 3*.6 *5.1 *5.7 -42.7 37.b -33.6 - 9 10 0 -3 0 6 0 -3 1- -3 8 12.T 6 2.0 6 7.9 9 1.4 j -o^e_ 2 2 2 2 - - * 3*.7 -26.8 * 21.5 17.9 5 2d.8 21.5 5 37.1 33.3 6- »f i .7 39.7 2 - -2 2 2 --? 0 - 0 0 - 0 0 - i h 11 -ft 12.0 3 6 *1.0 37.1 J 7 12.3 13.5 3 7 12.* 12.8 3 6 9.2 11.2 3 8 7.* -5 .7 0 6 6 9.8 11.* 0 8 7 3.1 2.9 0 8 8 7.* 7.2 0 6 9 9 . * 12.3 1 0 0 59.8 - *3 .2 - 7 15.1 17.1 8 38.0 -3b.1 -6 *0.3 - 3 7 . * 2 8 27.7 26.6 7 fl u k *n .o - * ! - * 2 - * 3 -fc 1 0.3 1 - 6 . 9 2 3.9 2 - * . * ~2 4 . A - 2 0 2 0 - 2 0 2 0 - : n 7 13-9 -11.3 7 6.) 11.* 5 11.3 11.3 6 2 * . J 24.8 9 4,2.6 3n.W 2 - 2 - 2 2 - 2 » 4 11.9 -12.0 4 11.9 -11.6 5 - 4 . 2 - 4 . 2 5 T.O -ft.5 6 12.1 -10.5 fl h.2 - J l . D . .. n o - 0 0 - 0 0 - 1 9 — 1 1 -ft.-. 3 9 1*.0 -12.7 3 10 36.8 3*.0 3 10 1*.6 -15.7 3 11 21.3 20.0 i 11 27.6 -26.0 1 Q I—__-_i_5 ___ 0 -1 *8.8 - * 1 . 0 2 7 * . l -56 . 0 -2 16.3 25. 0 3 3*.5 - 3 * . 1 0_=3 Ll*_?. 125.. 1 i 3 b - 2 -9 4J.1 - 3 7 . * 2 9 22.9 2*.6 2 9 -3 .3 - * .2 Z 10 22.3 -2* .2 7 -10 5.9 -9 .9 _ 3 7 3 14 4 7 4 7 * 10 * 7 1 12.0 1 -16.6 1 5.3 1 7.9 0 -11.5 1 . 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D -10 13.7 -11 . 0 11 20.* 19. D -11 18.8 - 1 * . - 13 16.6 -22.7 2 1* 2*.7 26.7 2 1* 12.1 -15.3 3 0 60.0 -61 .6 - - 3 23 3 15 3 12 3 1 20 9 -22.1 9 10.* 3 -16.1 1 19.5 - 18 - TABLE IV continued 9 9.8 -8 .3 3 5 7 35.7 32.9 ? in 11.1 -17 n 17.2 h Lr 1 6 10 9.9 -9 .0 1 R - 4 . n -1 .9 " * 0 0 0 -1.4 -0.4 1.3 -9.7 2 -12 7 1 •> 14.4 - 11•B— -12.8 5 8 5 8 8.0 26.2 5.'9 19.9 • t ; " u 8.6 e.s 9.3 -8.2 5 - 8.6 4.3 u.0 6.5 ' - 79. 1 -27.7 . 1 0 le.o 24.0 2 13 8.1 14.4 -B.4 3 5 9 - 4 . 9 -7.8 * 12.9 12.7 9.9 10.1 -2 6 5.3 -6 .3 0 ~2 42.1 -41.8 2 14 -5 .0 -2.4 3 5 10 21.9 -17.6 - l . H 1 . 0 5 -2 .8 -3 .3 2 7 16.9 20.3 0 28.7 30.8 2 15 11.8 -9 .5 1 1 11 -«. n . 1 2 -7 5.6 9.6 0 34.9 -32.4 1 n 14.1 u . n 1 5 1? 2 - -2 7 7 12.6 13.6 -11.0 - I* .5 0 n Jl 12.5 17 n 12.0 -?fl 1 -3 0 7.7 - e . e 6 0 13.B 11.4 "* 22.0 - 2 U 0 5 - 10 -2 .9 -i"a ~ 2 &- 1.6 . .._4.4. 0 5 7.3 T . J 3 -1 9.6 10.8 ! _ 6 1 13. 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