#------------------------------------------------------------------------------ #$Date: 2014-08-06 01:16:03 +0300 (Wed, 06 Aug 2014) $ #$Revision: 121403 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/30/04/2300467.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2300467 loop_ _publ_author_name 'Tan, Seng Lim' 'Ng, Seik Weng' _publ_section_title ; Does the size of a crystal matter in an X-ray crystal structure analysis of a small molecule? ; _journal_coeditor_code kk5175 _journal_issue 4 _journal_name_full 'Journal of Applied Crystallography' _journal_page_first 1443 _journal_page_last 1444 _journal_paper_doi 10.1107/S1600576714011297 _journal_volume 47 _journal_year 2014 _chemical_formula_moiety 'C20 H15 Br' _chemical_formula_sum 'C20 H15 Br' _chemical_formula_weight 335.23 _chemical_name_systematic ; (2-Bromo-1,2-diphenylethenyl)benzene ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 5.6130(4) _cell_length_b 8.5301(5) _cell_length_c 31.4348(17) _cell_measurement_reflns_used 2747 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 27.5350 _cell_measurement_theta_min 3.4980 _cell_volume 1505.08(16) _computing_cell_refinement 'CrysAlis PRO (Agilent, 2014)' _computing_data_collection 'CrysAlis PRO (Agilent, 2014)' _computing_data_reduction 'CrysAlis PRO (Agilent, 2014)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'publCIF (Westrip, 2010)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 10.4041 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Agilent Technologies SuperNova Dual diffractometer with Atlas detector' _diffrn_measurement_method '\w scan' _diffrn_radiation_monochromator Mirror _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0442 _diffrn_reflns_av_sigmaI/netI 0.0783 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_number 6537 _diffrn_reflns_theta_full 27.57 _diffrn_reflns_theta_max 27.57 _diffrn_reflns_theta_min 3.08 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 2.721 _exptl_absorpt_correction_T_max 0.601 _exptl_absorpt_correction_T_min 0.251 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details 'CrysAlis PRO (Agilent, 2014)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.479 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 680 _exptl_crystal_size_max 0.85 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.22 _refine_diff_density_max 1.061 _refine_diff_density_min -0.838 _refine_diff_density_rms 0.094 _refine_ls_abs_structure_details 'Flack parameter from 1430 Friedel pairs' _refine_ls_abs_structure_Flack 0.014(14) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 190 _refine_ls_number_reflns 3488 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.033 _refine_ls_R_factor_all 0.0618 _refine_ls_R_factor_gt 0.0480 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0335P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0873 _refine_ls_wR_factor_ref 0.0934 _reflns_number_gt 3007 _reflns_number_total 3488 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL P212121 1430 Friedel pairs rem eqivR 0.23 CELL 0.71073 5.6130 8.5301 31.4348 90.0000 90.0000 90.0000 ZERR 4 0.0004 0.0005 0.0017 0.0000 0.0000 0.0000 LATT -1 SYMM -x+1/2,-y, z+1/2 SYMM -x, y+1/2,-z+1/2 SYMM x+1/2,-y+1/2,-z SFAC C H Br UNIT 80 60 4 ACTA TEMP -173 SIZE 0.8 0.3 0.2 L.S. 100 BOND $H CONF FMAP 2 PLAN -1 WGHT 0.033500 FVAR 5.32545 BR1 3 1.005682 0.152172 0.208409 11.00000 0.02968 0.01639 = 0.00946 0.00176 0.00140 -0.00021 C1 1 1.053141 0.047672 0.122903 11.00000 0.01126 0.01306 = 0.01698 0.00081 0.00340 -0.00260 C2 1 1.262658 -0.035649 0.131094 11.00000 0.02040 0.02183 = 0.01367 0.00346 0.00187 -0.00249 AFIX 43 H2 2 1.367316 -0.001343 0.152944 11.00000 -1.20000 AFIX 0 C3 1 1.318767 -0.168175 0.107509 11.00000 0.01576 0.01611 = 0.02018 0.00971 0.00507 0.00608 AFIX 43 H3 2 1.462307 -0.223419 0.113137 11.00000 -1.20000 AFIX 0 C4 1 1.166733 -0.220375 0.075813 11.00000 0.02597 0.01261 = 0.01882 -0.00249 0.00645 -0.00582 AFIX 43 H4 2 1.205925 -0.310808 0.059622 11.00000 -1.20000 AFIX 0 C5 1 0.958560 -0.140286 0.067955 11.00000 0.02012 0.01451 = 0.01723 -0.00083 -0.00220 -0.00445 AFIX 43 H5 2 0.852853 -0.176694 0.046521 11.00000 -1.20000 AFIX 0 C6 1 0.901436 -0.006441 0.091119 11.00000 0.01662 0.01181 = 0.01567 0.00707 -0.00077 -0.00195 AFIX 43 H6 2 0.757885 0.048366 0.085192 11.00000 -1.20000 AFIX 0 C7 1 0.910657 0.366751 0.087732 11.00000 0.01542 0.01007 = 0.01305 0.00113 -0.00102 -0.00360 C8 1 1.108986 0.333094 0.062300 11.00000 0.01579 0.00897 = 0.01993 0.00206 0.00010 -0.00030 AFIX 43 H8 2 1.238594 0.275952 0.074017 11.00000 -1.20000 AFIX 0 C9 1 1.119004 0.382011 0.020205 11.00000 0.01928 0.01146 = 0.01525 -0.00622 0.00489 -0.00326 AFIX 43 H9 2 1.253723 0.357586 0.003154 11.00000 -1.20000 AFIX 0 C10 1 0.930054 0.467132 0.003188 11.00000 0.02345 0.01243 = 0.00779 0.00152 -0.00121 -0.00517 AFIX 43 H10 2 0.936216 0.501614 -0.025527 11.00000 -1.20000 AFIX 0 C11 1 0.733495 0.501592 0.027977 11.00000 0.01595 0.01059 = 0.02083 -0.00010 -0.00643 0.00168 AFIX 43 H11 2 0.604292 0.558820 0.016149 11.00000 -1.20000 AFIX 0 C12 1 0.724166 0.453202 0.069844 11.00000 0.01196 0.01348 = 0.01415 -0.00256 0.00047 -0.00114 AFIX 43 H12 2 0.589338 0.478951 0.086723 11.00000 -1.20000 AFIX 0 C13 1 0.778826 0.440798 0.162371 11.00000 0.01615 0.00975 = 0.01280 0.00094 0.00281 0.00196 C14 1 0.870137 0.591771 0.166272 11.00000 0.02101 0.01571 = 0.00840 0.00557 -0.00128 -0.00461 AFIX 43 H14 2 1.013796 0.619003 0.152105 11.00000 -1.20000 AFIX 0 C15 1 0.752059 0.703023 0.190820 11.00000 0.04002 0.01093 = 0.01590 0.00136 -0.00746 -0.00430 AFIX 43 H15 2 0.816242 0.805546 0.193648 11.00000 -1.20000 AFIX 0 C16 1 0.541548 0.664636 0.211097 11.00000 0.02249 0.02330 = 0.01492 -0.00470 -0.00048 0.01230 AFIX 43 H16 2 0.460707 0.740796 0.227765 11.00000 -1.20000 AFIX 0 C17 1 0.448646 0.515023 0.207082 11.00000 0.01894 0.03285 = 0.01484 -0.00201 0.00231 -0.00035 AFIX 43 H17 2 0.302937 0.488928 0.220729 11.00000 -1.20000 AFIX 0 C18 1 0.567795 0.403284 0.183197 11.00000 0.02078 0.01649 = 0.01810 -0.00273 0.00402 -0.00172 AFIX 43 H18 2 0.504835 0.300215 0.181028 11.00000 -1.20000 AFIX 0 C19 1 0.980413 0.185648 0.148502 11.00000 0.01523 0.01982 = 0.01227 -0.00172 -0.00522 -0.00403 C20 1 0.896613 0.322643 0.134106 11.00000 0.01268 0.01575 = 0.01805 -0.00553 0.00018 -0.00726 HKLF 4 REM P212121 1430 Friedel pairs REM R1 = 0.0480 for 3007 Fo > 4sig(Fo) and 0.0618 for all 3488 data REM 190 parameters refined using 0 restraints END WGHT 0.0286 0.0000 REM Highest difference peak 1.061, deepest hole -0.838, 1-sigma level 0.094 Q1 1 0.8445 0.1432 0.2047 11.00000 0.05 1.06 ; _[local]_cod_data_source_file kk5175sup1.cif _[local]_cod_data_source_block Br1 _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Gaussian' changed to 'gaussian' according to /usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/IUCr/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius Adding full bibliography for 2300463--2300482.cif. ; _cod_database_code 2300467 _cod_database_fobs_code 2300467 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags Br1 Br 1.00568(9) 0.15217(4) 0.208409(9) 0.01851(11) Uani 1 1 d . C1 C 1.0531(6) 0.0477(4) 0.12290(11) 0.0138(8) Uani 1 1 d . C2 C 1.2627(7) -0.0356(5) 0.13109(12) 0.0186(9) Uani 1 1 d . H2 H 1.3673 -0.0013 0.1529 0.022 Uiso 1 1 calc R C3 C 1.3188(7) -0.1682(5) 0.10751(12) 0.0174(9) Uani 1 1 d . H3 H 1.4623 -0.2234 0.1131 0.021 Uiso 1 1 calc R C4 C 1.1667(8) -0.2204(5) 0.07581(12) 0.0191(9) Uani 1 1 d . H4 H 1.2059 -0.3108 0.0596 0.023 Uiso 1 1 calc R C5 C 0.9586(7) -0.1403(4) 0.06796(11) 0.0173(9) Uani 1 1 d . H5 H 0.8529 -0.1767 0.0465 0.021 Uiso 1 1 calc R C6 C 0.9014(7) -0.0064(4) 0.09112(11) 0.0147(8) Uani 1 1 d . H6 H 0.7579 0.0484 0.0852 0.018 Uiso 1 1 calc R C7 C 0.9107(7) 0.3668(4) 0.08773(11) 0.0128(8) Uani 1 1 d . C8 C 1.1090(7) 0.3331(4) 0.06230(12) 0.0149(8) Uani 1 1 d . H8 H 1.2386 0.2760 0.0740 0.018 Uiso 1 1 calc R C9 C 1.1190(7) 0.3820(4) 0.02021(12) 0.0153(9) Uani 1 1 d . H9 H 1.2537 0.3576 0.0032 0.018 Uiso 1 1 calc R C10 C 0.9301(7) 0.4671(4) 0.00319(11) 0.0146(9) Uani 1 1 d . H10 H 0.9362 0.5016 -0.0255 0.017 Uiso 1 1 calc R C11 C 0.7335(7) 0.5016(4) 0.02798(12) 0.0158(9) Uani 1 1 d . H11 H 0.6043 0.5588 0.0161 0.019 Uiso 1 1 calc R C12 C 0.7242(7) 0.4532(4) 0.06984(11) 0.0132(8) Uani 1 1 d . H12 H 0.5893 0.4790 0.0867 0.016 Uiso 1 1 calc R C13 C 0.7788(7) 0.4408(4) 0.16237(11) 0.0129(8) Uani 1 1 d . C14 C 0.8701(7) 0.5918(4) 0.16627(11) 0.0150(9) Uani 1 1 d . H14 H 1.0138 0.6190 0.1521 0.018 Uiso 1 1 calc R C15 C 0.7521(8) 0.7030(5) 0.19082(12) 0.0223(10) Uani 1 1 d . H15 H 0.8162 0.8055 0.1936 0.027 Uiso 1 1 calc R C16 C 0.5415(7) 0.6646(5) 0.21110(11) 0.0202(9) Uani 1 1 d . H16 H 0.4607 0.7408 0.2278 0.024 Uiso 1 1 calc R C17 C 0.4486(7) 0.5150(5) 0.20708(11) 0.0222(9) Uani 1 1 d . H17 H 0.3029 0.4889 0.2207 0.027 Uiso 1 1 calc R C18 C 0.5678(7) 0.4033(5) 0.18320(12) 0.0185(9) Uani 1 1 d . H18 H 0.5048 0.3002 0.1810 0.022 Uiso 1 1 calc R C19 C 0.9804(8) 0.1856(4) 0.14850(10) 0.0158(8) Uani 1 1 d . C20 C 0.8966(7) 0.3226(4) 0.13411(11) 0.0155(8) Uani 1 1 d . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0297(2) 0.01639(17) 0.00946(16) 0.00176(13) 0.0014(2) -0.0002(2) C1 0.011(2) 0.0131(16) 0.0170(17) 0.0008(15) 0.0034(14) -0.0026(16) C2 0.020(2) 0.022(2) 0.0137(19) 0.0035(18) 0.0019(16) -0.002(2) C3 0.016(2) 0.016(2) 0.020(2) 0.0097(18) 0.0051(16) 0.0061(19) C4 0.026(3) 0.0126(19) 0.019(2) -0.0025(18) 0.0064(18) -0.0058(19) C5 0.020(3) 0.0145(17) 0.0172(17) -0.0008(15) -0.0022(15) -0.004(2) C6 0.017(2) 0.0118(18) 0.0157(18) 0.0071(16) -0.0008(15) -0.0020(16) C7 0.015(2) 0.0101(18) 0.0131(17) 0.0011(16) -0.0010(14) -0.0036(16) C8 0.016(2) 0.0090(18) 0.020(2) 0.0021(18) 0.0001(15) -0.0003(17) C9 0.019(2) 0.0115(19) 0.0152(19) -0.0062(17) 0.0049(15) -0.0033(17) C10 0.023(2) 0.0124(17) 0.0078(16) 0.0015(16) -0.0012(14) -0.0052(17) C11 0.016(2) 0.0106(19) 0.021(2) -0.0001(16) -0.0064(17) 0.0017(17) C12 0.012(2) 0.0135(18) 0.0141(19) -0.0026(16) 0.0005(15) -0.0011(17) C13 0.016(2) 0.0097(17) 0.0128(18) 0.0009(16) 0.0028(15) 0.0020(17) C14 0.021(2) 0.0157(19) 0.0084(17) 0.0056(16) -0.0013(15) -0.0046(17) C15 0.040(3) 0.0109(18) 0.016(2) 0.0014(17) -0.0075(19) -0.004(2) C16 0.022(2) 0.0233(19) 0.0149(17) -0.0047(16) -0.0005(16) 0.0123(19) C17 0.019(2) 0.033(2) 0.0148(17) -0.0020(18) 0.0023(16) -0.0004(19) C18 0.021(3) 0.0165(18) 0.0181(19) -0.0027(16) 0.0040(16) -0.0017(17) C19 0.015(2) 0.0198(18) 0.0123(16) -0.0017(13) -0.0052(18) -0.004(2) C20 0.013(2) 0.0158(19) 0.018(2) -0.0055(17) 0.0002(15) -0.0073(17) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 0 -10 -26 0.1049 0.0166 -10.0200 -26.1913 -0.3833 0.9468 -0.0060 0 -7 36 0.1888 -0.0137 -7.0286 36.0865 -0.0430 -0.0171 -1.0004 0 7 -36 0.1725 0.0137 7.0286 -36.0865 0.0430 0.0171 1.0004 8 1 -4 0.4349 8.0344 0.9952 -4.0537 0.9501 0.3727 0.0759 -8 0 -1 0.3864 -8.0325 0.0089 -0.9580 -0.9434 -0.3720 0.0644 0 -10 22 0.1290 -0.0058 -10.0329 22.0038 -0.1837 0.3447 -0.8883 0 10 24 0.1115 -0.0157 10.0205 24.1832 0.3750 -0.9217 0.0428 0 10 -25 0.1519 0.0072 10.0337 -25.0160 0.1713 -0.3071 0.9434 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C6 C1 C2 118.6(3) C6 C1 C19 119.0(3) C2 C1 C19 122.3(3) C3 C2 C1 120.4(4) C3 C2 H2 119.8 C1 C2 H2 119.8 C4 C3 C2 120.4(4) C4 C3 H3 119.8 C2 C3 H3 119.8 C5 C4 C3 119.5(4) C5 C4 H4 120.2 C3 C4 H4 120.2 C4 C5 C6 120.6(4) C4 C5 H5 119.7 C6 C5 H5 119.7 C5 C6 C1 120.5(4) C5 C6 H6 119.8 C1 C6 H6 119.8 C12 C7 C8 118.3(3) C12 C7 C20 118.8(3) C8 C7 C20 122.9(3) C9 C8 C7 121.0(4) C9 C8 H8 119.5 C7 C8 H8 119.5 C10 C9 C8 119.5(3) C10 C9 H9 120.3 C8 C9 H9 120.3 C11 C10 C9 120.2(3) C11 C10 H10 119.9 C9 C10 H10 119.9 C12 C11 C10 120.3(4) C12 C11 H11 119.9 C10 C11 H11 119.9 C11 C12 C7 120.8(3) C11 C12 H12 119.6 C7 C12 H12 119.6 C18 C13 C14 119.0(4) C18 C13 C20 120.0(3) C14 C13 C20 120.8(3) C15 C14 C13 120.3(4) C15 C14 H14 119.8 C13 C14 H14 119.8 C16 C15 C14 120.1(4) C16 C15 H15 119.9 C14 C15 H15 119.9 C17 C16 C15 119.9(4) C17 C16 H16 120.1 C15 C16 H16 120.1 C16 C17 C18 120.1(4) C16 C17 H17 119.9 C18 C17 H17 119.9 C17 C18 C13 120.5(4) C17 C18 H18 119.7 C13 C18 H18 119.7 C20 C19 C1 127.3(3) C20 C19 Br1 119.3(3) C1 C19 Br1 113.3(3) C19 C20 C13 122.8(3) C19 C20 C7 121.8(3) C13 C20 C7 115.4(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Br1 C19 1.910(3) C1 C6 1.392(5) C1 C2 1.398(5) C1 C19 1.483(5) C2 C3 1.388(5) C2 H2 0.9500 C3 C4 1.385(5) C3 H3 0.9500 C4 C5 1.376(6) C4 H4 0.9500 C5 C6 1.392(5) C5 H5 0.9500 C6 H6 0.9500 C7 C12 1.398(5) C7 C8 1.400(5) C7 C20 1.508(5) C8 C9 1.389(5) C8 H8 0.9500 C9 C10 1.392(5) C9 H9 0.9500 C10 C11 1.382(5) C10 H10 0.9500 C11 C12 1.380(5) C11 H11 0.9500 C12 H12 0.9500 C13 C18 1.391(5) C13 C14 1.391(5) C13 C20 1.497(5) C14 C15 1.391(6) C14 H14 0.9500 C15 C16 1.382(6) C15 H15 0.9500 C16 C17 1.384(6) C16 H16 0.9500 C17 C18 1.385(5) C17 H17 0.9500 C18 H18 0.9500 C19 C20 1.339(5) loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion C6 C1 C2 C3 0.9(5) C19 C1 C2 C3 177.2(3) C1 C2 C3 C4 -0.6(6) C2 C3 C4 C5 -0.3(6) C3 C4 C5 C6 0.9(6) C4 C5 C6 C1 -0.6(6) C2 C1 C6 C5 -0.3(5) C19 C1 C6 C5 -176.7(3) C12 C7 C8 C9 -1.0(5) C20 C7 C8 C9 -177.1(3) C7 C8 C9 C10 0.7(5) C8 C9 C10 C11 -0.4(5) C9 C10 C11 C12 0.6(6) C10 C11 C12 C7 -1.0(6) C8 C7 C12 C11 1.2(5) C20 C7 C12 C11 177.4(3) C18 C13 C14 C15 0.3(6) C20 C13 C14 C15 176.5(4) C13 C14 C15 C16 -0.8(6) C14 C15 C16 C17 0.2(6) C15 C16 C17 C18 0.8(6) C16 C17 C18 C13 -1.3(6) C14 C13 C18 C17 0.7(6) C20 C13 C18 C17 -175.6(4) C6 C1 C19 C20 -48.4(6) C2 C1 C19 C20 135.3(5) C6 C1 C19 Br1 129.6(3) C2 C1 C19 Br1 -46.7(5) C1 C19 C20 C13 166.2(4) Br1 C19 C20 C13 -11.7(6) C1 C19 C20 C7 -12.5(6) Br1 C19 C20 C7 169.5(3) C18 C13 C20 C19 -62.8(5) C14 C13 C20 C19 120.9(4) C18 C13 C20 C7 116.0(4) C14 C13 C20 C7 -60.3(5) C12 C7 C20 C19 144.4(4) C8 C7 C20 C19 -39.5(6) C12 C7 C20 C13 -34.4(5) C8 C7 C20 C13 141.6(4)