J. Am. Chem. Soc., 1996, 118(17), , DOI: /ja953373m

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1 J. Am. Chem. Soc., 1996, 118(17), , DOI: /ja953373m Terms & Conditions Electronic Supporting Information files are available without a subscription to ACS Web Editions. The American Chemical Society holds a copyright ownership interest in any copyrightable Supporting Information. Files available from the ACS website may be downloaded for personal use only. Users are not otherwise permitted to reproduce, republish, redistribute, or sell any Supporting Information from the ACS website, either in whole or in part, in either machinereadable form or any other form without permission from the American Chemical Society. For permission to reproduce, republish and redistribute this material, requesters must process their own requests via the RightsLink permission system. Information about how to use the RightsLink permission system can be found at Copyright 1996 American Chemical Society

2 American Chemical Society J. Am. Chem. Soc. VI 18 Page409O Reddy Supplemental Page 1,J 48q3-1 Br tetrakis-(4-bromophenyl)methane(6) Formula Molecular Weight Crystal System Space Group Unit Cell Dimensions C25H 16 Br tetragonal I4 a = (2) A c = 7.114(2) A Cell Volume z F(000) Density(calc.) (3) A Mg m-3 2

3 American Chemical Society J. Am. Chem. Soc. VI 18 Page409O Reddy Supplemental Page 2 Table 1. Fractional co-ordinates and equivalent thermal parameters for compound (6) (e.s.d's are in parentheses). j4o~&~2~ Atom x y z Bea Br C(1) C(2) C(3) C(4) C(5) C(6) C(7) HC(3) HC(4) HC(6) HC(7) (1) (8) (9) (8) (9) (10) (9) (1) (8) (9) (8) (9) (9) (9) (2) (15) (17) (14) (17) (18) (16) (5) 3.58(56) 3.12(26) 3.89(30) 3.36(28) 4.30(33) 4.25(33) 4.09(31) 3

4 American Chemical Society J. Am. Chem. Soc. VI 18 Page409O Reddy Supplemental Page 3 SJ 40'3-3 Table 2. Bond lengths (A) and angles (0) for the non-hydrogen atoms for compound (6) (e.s.d's are in parentheses). C(1)-C(2) C(2)-C(3) C(3)-C(4) C(4)-C(5) C(5)-C(6) C(6)-C(7) C(7)-C(2) C(5)-Br 1.554(10) 1.382(15) 1.370(15) 1.384(16) 1.328(15) 1.428(16) 1.378(14) 1.919(11) C(2)-C(1)-C(2)a C(2)-C(1)-C(2)b C(1)-C(2)-C(3) C(1)-C(2)-C7 C(7)-C(2)-C(3) C(2)-C(3)-C(4) 106.7(7) 110.9(4) 118.7(8) 123.9(8) 117.4(9) 123.2(10) C(3)-C(4)-C(5) C(4)-C(5)-Br Br-C(5)-C(6) C(4)-C(5)-(C6) C(5)-C(6)-C(7) C(6)-C(7)-C(2) 117.2(10) 118.0(9) 118.8(9) 123.1(11) 118.5(10) 120.5(10) Symmetry transformations: a -x, -y, z b y,-x,-z 4

5 American Chemical Society J. Am. Chem. Soc. VI 18 Page409O Reddy Supplemental Page 4 Table 3. Final anisotropic thermal vibrational parameters for non-hydrogen atoms for compound (6) (e.s.d's are in parentheses). Atom Pll 022 P33 P P23 Br C(1) C(2) C(3) C(4) C(5) C(6) C(7) (1) (16) (7) (8) (8) (8) (8) (8) (1) (7) (7) (8) (8) (9) (8) (5) (66) (23) (27) (23) (33) (29) (28) (1) (6) (6) (6) (7) (7) (7) (2) (11) (13) (11) (14) (13) (12) (2) (11) (12) (10) (13) (13) (14) The anisotropic temperature factor is exponent takes the form: (-(h k 2 P P33 + 2hkP12 + 2hl ki023)) 5

6 American Chemical Society J. Am. Chem. Soc. VI 18 Page409O Reddy Supplemental Page 5 Br rr 0 ~ Br)-Irr 1:1 complex of tetraphenylmethane and tetrabromomethane (8) Formula CH2Br 4 Molecular Weight Crystal System Space Group Unit Cell Dimensions Cell Volume tetragonal I4 a = (1) A c = 7.298(1) A (2) A3 Z 2 F(OOO) 632 Density(calc.) 1.86 Mg m- 3 6

7 American Chemical Society J. Am. Chem. Soc. VI 18 Page409O Reddy Supplemental Page 6 Table 4. Fractional co-ordinates and equivalent thermal parameters for compound (8) (e.s.d's are in parentheses). Atom x y z Bea Br (1) (1) (1) 5.21(2) C 3.83(32) C(1) (21) C(2) (4) (4) (8) 2.09(12) C(3) (4) (4) (9) 2.56(12) C(4) (5) (4) (10) 3.57(16) C(5) (5) (4) (10) 3.75(18) C(7) (4) (4) (8) 2.77(14) HC(3) HC(4) HC(5) HC(6) HC(6)

8 American Chemical Society J. Am. Chem. Soc. VI 18 Page409O Reddy Supplemental Page 7 Table 5. Bond lengths (A) and angles (0) for the non-hydrogen atoms for compound (8) (e.s.d's are in parentheses). Jdb95-q C-Br C(1)-C(2) C(2)-C(3) C(3)-C(4) C(4)-C(5) C(5)-C(6) C(6)-C(7) C(7)-C(2) 1.926(1) 1.543(5) 1.399(7) 1.388(8) 1.379(9) 1.393(8) 1.390(8) 1.394(8) Br-C-Bra Br-C-Brb C(2)-C(1)-C(2)c C(2)-C(1)-C(2)d C(1)-C(2)-C(3) C(1)-C(2)-C(7) 110.6(1) 108.9(1) 106.5(4) 111.0(2) 123.8(5) 118.8(4) C(7)-C(2)-C(3) C(2)-C(3)-(C4) C(3)-C(4)-C(5) C(4)-C(5)-C(6) C(5)-C(6)-C(7) C(6)-C(7)-C(2) 117.5(5) 121.2(6) 120.5(5) 119.6(6) 119.6(6) 121.7(5) Symmetry transformations: a -x, -y, z b y,-x,-z c 1-x, -y, z d 1/2+y, 1/2-x, 1/2-z 8

9 American Chemical Society J. Am. Chem. Soc. VI 18 Page409O Reddy Supplemental Page 8 j q( 3- Y 2 Table 6. Final anisotropic thermal vibrational parameters for non-hydrogen atoms for compound (8) (e.s.d's are in parentheses). Atom P P P13 P23 Br C C(1) C(2) C(3) C(4) C(5) C(6) C(7) (1) (9) 0.025(7) (3) (3) (4) (4) (4) (4) (1) (3) (3) (8) (3) (3) (4) (2) (36) (20) (10) (10) (33) (29) (28) (11) (1) (2) (3) (7) (7) (7) (7) (1) (5) (6) (7) (8) (8) (5) (1) (5) (7) (7) (7) (7) (6) The anisotropic temperature factor is exponent takes the form: (-(h 2 p 11 + k 2 P P33 + 2hkP12 + 2hl13 + 2ki023)) 9

10 American Chemical Society J. Am. Chem. Soc. VI 18 Page409O Reddy Supplemental Page 9 Crystallography. Crystal data. C25HI 6 Br 4, M 636.0, tetragonal, space group I4, a (2), c 7.114(2)A, V (3)A3, Dc 1.84 g cm-3, Z 2, IMo cm-1. Crystal size 0.10 by 0.11 by 0.30 mm, 2 0 max 500, min. and max.transmission factors 0.47 and The number of reflexions was 443 considered observed out of 596 unique data. Final residuals R, Rw were 0.048, for the observed data. The enantiomer is confirmed, the alternative giving R, Rw 0.059, Crystal data. C25H20.CBr 4, M 652.1, tetragonal, space group If, a (1), c 7.298(1)A, V (2)A3, De 1.86 g cm- 3, Z 2, ILMO cm-1. Crystal size 0.10 by 0.13 by 0.14 mm, 2 0 max 500, min. and max.transmission factors 0.44 and The number of reflexions was 507 considered observed out of 603 unique data. Final residuals R, Rw were 0.027, for the observed data. The enantiomer is confirmed, the alternative giving R, Rw 0.043, Structure Determination. Reflexion data were measured with an Enraf-Nonius CAD-4 diffractometer in 0/20 scan mode using graphite monochromatized molybdenum radiation (X A). Data were corrected for absorption using the method of de Meulenaer and Tompal. Reflexions with I > 3a(I) were considered observed. The structures were determined by direct phasing and Fourier methods. Hydrogen atoms were included in calculated positions and were assigned thermal parameters equal to those of the atom to which they were bonded. Positional and anisotropic thermal parameters for the non-hydrogen atoms were refined using full matrix least squares. Reflexion weights used were 1/o 2 (Fo), with 0(Fo) being derived from a(io) = [2(Io) + (0.04Io) The weighted residual is defined as Rw=(LwA 2 /IwFo 2 )1/ 2. Atomic scattering factors and anomalous dispersion parameters were from International Tables for X- ray Crystallography. 2 Structure solutions were by MULTAN80 3 and refinement used BLOCKLS, a local version of ORFLS. 4 A DEC Alpha-AXP workstation was used for calculations. I De Meulenaer, J. and Tompa, H. Acta Cryst., 1965, 19, Ibers, J.A. and Hamilton, W.C., (Eds) 'International Tables for X-Ray Crystallography' Vol. 4, Kynoch Press, Birmingham, Main, P.,'MULTAN80', University of York, England, Busing, W.R., Martin, K.O., and Levy, H.A.,'ORFLS', Oak Ridge National Laboratory, Tennessee, U.S.A., 1962.

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