#------------------------------------------------------------------------------ #$Date: 2017-04-20 05:33:01 +0300 (Thu, 20 Apr 2017) $ #$Revision: 195612 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/04/27/7042720.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7042720 loop_ _publ_author_name 'Armstrong, David' 'Taullaj, Fioralba' 'Singh, Kamalpreet' 'Mirabi, Bijan' 'Lough, Alan' 'Fekl, Ulrich Werner' _publ_section_title ; Adamantyl Metal Complexes: New Routes to Adamantyl Anions and New Transmetallations ; _journal_name_full 'Dalton Trans.' _journal_paper_doi 10.1039/C7DT00428A _journal_year 2017 _chemical_formula_moiety 'C20 H30 Bi Br' _chemical_formula_sum 'C20 H30 Bi Br' _chemical_formula_weight 559.33 _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2017-01-19 deposited with the CCDC. 2017-04-19 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 93.377(3) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 25.362(2) _cell_length_b 6.4647(5) _cell_length_c 21.7366(16) _cell_measurement_reflns_used 6848 _cell_measurement_temperature 147(2) _cell_measurement_theta_max 27.44 _cell_measurement_theta_min 2.40 _cell_volume 3557.7(5) _computing_cell_refinement APEX2 _computing_data_collection 'APEX2 (Bruker, 2014)' _computing_data_reduction 'SAINT (Bruker, 2014)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _diffrn_ambient_temperature 147(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Bruker Kappa APEX-DUO CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0617 _diffrn_reflns_av_unetI/netI 0.0476 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 22873 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.994 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.608 _diffrn_reflns_theta_min 1.609 _diffrn_source 'sealed tube with Bruker Triumph monochromator' _exptl_absorpt_coefficient_mu 12.154 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.4350 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_crystal_colour orange _exptl_crystal_density_diffrn 2.089 _exptl_crystal_description needle _exptl_crystal_F_000 2144 _exptl_crystal_size_max 0.100 _exptl_crystal_size_mid 0.015 _exptl_crystal_size_min 0.015 _refine_diff_density_max 1.760 _refine_diff_density_min -1.339 _refine_diff_density_rms 0.170 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 199 _refine_ls_number_reflns 4112 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.044 _refine_ls_R_factor_all 0.0456 _refine_ls_R_factor_gt 0.0284 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0149P)^2^+11.4455P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0543 _refine_ls_wR_factor_ref 0.0588 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3271 _reflns_number_total 4112 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7dt00428a2.cif _cod_data_source_block d1628 _cod_database_code 7042720 _shelx_shelxl_version_number 2014/7 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.376 _shelx_estimated_absorpt_t_max 0.839 _shelx_res_file ; d1628.res created by SHELXL-2014/7 TITL mo_d1628_0m in C2/c CELL 0.71073 25.3617 6.4647 21.7366 90.000 93.377 90.000 ZERR 8.00 0.0020 0.0005 0.0016 0.000 0.003 0.000 LATT 7 SYMM -x, y, -z+1/2 SFAC C H BR BI UNIT 160 240 8 8 TEMP -126.160 SIZE 0.015 0.015 0.100 ACTA L.S. 4 FMAP 2 PLAN 20 HTAB BOND $H CONF WGHT 0.014900 11.445499 FVAR 0.03421 BI1 4 0.707894 0.456971 0.424162 11.00000 0.00970 0.01469 = 0.01329 0.00120 0.00177 -0.00071 BR1 3 0.707943 0.871988 0.431637 11.00000 0.01590 0.01523 = 0.02257 -0.00164 0.00074 -0.00098 C1 1 0.762251 0.431173 0.342872 11.00000 0.00851 0.01420 = 0.01220 -0.00153 0.00246 0.00166 AFIX 13 H1A 2 0.738996 0.406448 0.304821 11.00000 -1.20000 AFIX 0 C2 1 0.798206 0.242174 0.351740 11.00000 0.01326 0.00952 = 0.01655 0.00219 0.00341 -0.00202 AFIX 13 H2A 2 0.776515 0.117834 0.360769 11.00000 -1.20000 AFIX 0 C3 1 0.839914 0.278988 0.405332 11.00000 0.01806 0.01814 = 0.01559 0.00726 0.00110 0.00100 AFIX 23 H3A 2 0.822091 0.301365 0.444096 11.00000 -1.20000 H3B 2 0.862913 0.155799 0.410710 11.00000 -1.20000 AFIX 0 C4 1 0.873393 0.468613 0.391400 11.00000 0.01010 0.02414 = 0.01906 0.00214 -0.00165 -0.00518 AFIX 13 H4A 2 0.900267 0.492321 0.426217 11.00000 -1.20000 AFIX 0 C5 1 0.901442 0.431709 0.331765 11.00000 0.00836 0.02342 = 0.02450 0.00492 0.00336 -0.00229 AFIX 23 H5A 2 0.924707 0.309121 0.336652 11.00000 -1.20000 H5B 2 0.923644 0.552923 0.322994 11.00000 -1.20000 AFIX 0 C6 1 0.860249 0.396705 0.277741 11.00000 0.01161 0.01501 = 0.01753 0.00156 0.00616 0.00153 AFIX 13 H6A 2 0.878432 0.373694 0.238727 11.00000 -1.20000 AFIX 0 C7 1 0.823614 0.587639 0.270941 11.00000 0.01466 0.01147 = 0.01569 0.00177 0.00319 0.00046 AFIX 23 H7A 2 0.844667 0.711450 0.261563 11.00000 -1.20000 H7B 2 0.797002 0.565627 0.236390 11.00000 -1.20000 AFIX 0 C8 1 0.795624 0.622777 0.330977 11.00000 0.01230 0.01134 = 0.01574 0.00162 0.00182 0.00429 AFIX 13 H8A 2 0.772111 0.746623 0.326238 11.00000 -1.20000 AFIX 0 C9 1 0.826718 0.206423 0.292174 11.00000 0.01709 0.01501 = 0.01954 -0.00302 0.00462 0.00008 AFIX 23 H9A 2 0.800402 0.180610 0.257565 11.00000 -1.20000 H9B 2 0.849735 0.083102 0.296982 11.00000 -1.20000 AFIX 0 C10 1 0.837196 0.659646 0.383715 11.00000 0.01634 0.01355 = 0.01997 -0.00090 0.00291 -0.00496 AFIX 23 H10A 2 0.819584 0.685339 0.422444 11.00000 -1.20000 H10B 2 0.858537 0.783028 0.374693 11.00000 -1.20000 AFIX 0 C11 1 0.629794 0.452314 0.363441 11.00000 0.00833 0.01955 = 0.01013 0.00273 -0.00087 0.00125 AFIX 13 H11A 2 0.638400 0.477701 0.319772 11.00000 -1.20000 AFIX 0 C12 1 0.590241 0.617517 0.381518 11.00000 0.01023 0.00898 = 0.02378 -0.00278 0.00460 -0.00364 AFIX 13 H12A 2 0.607087 0.757078 0.379729 11.00000 -1.20000 AFIX 0 C13 1 0.541747 0.610328 0.336171 11.00000 0.01218 0.01405 = 0.02671 0.00407 -0.00084 0.00178 AFIX 23 H13A 2 0.516189 0.718050 0.347133 11.00000 -1.20000 H13B 2 0.552505 0.638960 0.293959 11.00000 -1.20000 AFIX 0 C14 1 0.515702 0.397862 0.338031 11.00000 0.01344 0.01856 = 0.01766 -0.00150 0.00162 0.00072 AFIX 13 H14A 2 0.484280 0.394235 0.308017 11.00000 -1.20000 AFIX 0 C15 1 0.497828 0.357831 0.403818 11.00000 0.01343 0.01529 = 0.02951 -0.00478 0.00685 -0.00530 AFIX 23 H15A 2 0.471962 0.464390 0.414782 11.00000 -1.20000 H15B 2 0.480643 0.220645 0.405642 11.00000 -1.20000 AFIX 0 C16 1 0.546270 0.365253 0.449304 11.00000 0.01528 0.01806 = 0.01616 -0.00327 0.00888 -0.00341 AFIX 13 H16A 2 0.535168 0.338871 0.491989 11.00000 -1.20000 AFIX 0 C17 1 0.585782 0.196795 0.431494 11.00000 0.01600 0.01533 = 0.01602 0.00295 0.00263 -0.00742 AFIX 23 H17A 2 0.616732 0.196786 0.461458 11.00000 -1.20000 H17B 2 0.568760 0.059175 0.432779 11.00000 -1.20000 AFIX 0 C18 1 0.603853 0.237493 0.366885 11.00000 0.01140 0.00835 = 0.01828 -0.00072 0.00176 0.00314 AFIX 13 H18A 2 0.629598 0.128478 0.355766 11.00000 -1.20000 AFIX 0 C19 1 0.555042 0.231349 0.321140 11.00000 0.01110 0.01633 = 0.01614 -0.00214 -0.00084 -0.00402 AFIX 23 H19A 2 0.566003 0.255160 0.278751 11.00000 -1.20000 H19B 2 0.538136 0.093511 0.322439 11.00000 -1.20000 AFIX 0 C20 1 0.572950 0.578507 0.446771 11.00000 0.01668 0.01179 = 0.02198 -0.00831 0.00433 -0.00377 AFIX 23 H20A 2 0.547910 0.687483 0.458215 11.00000 -1.20000 H20B 2 0.604055 0.583085 0.476475 11.00000 -1.20000 AFIX 0 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM mo_d1628_0m in C2/c REM R1 = 0.0284 for 3271 Fo > 4sig(Fo) and 0.0456 for all 4112 data REM 199 parameters refined using 0 restraints END WGHT 0.0148 11.6242 REM No hydrogen bonds found for HTAB generation REM Highest difference peak 1.760, deepest hole -1.339, 1-sigma level 0.170 Q1 1 0.7084 0.3024 0.4183 11.00000 0.05 1.76 Q2 1 0.7098 0.7124 0.4232 11.00000 0.05 1.49 Q3 1 0.7491 0.6222 0.4207 11.00000 0.05 1.06 Q4 1 0.7112 0.4565 0.4652 11.00000 0.05 1.05 Q5 1 0.7030 0.4661 0.3876 11.00000 0.05 0.96 Q6 1 0.7102 1.1319 0.3956 11.00000 0.05 0.88 Q7 1 0.7078 1.0238 0.4268 11.00000 0.05 0.85 Q8 1 0.6667 0.6089 0.4226 11.00000 0.05 0.84 Q9 1 0.6698 0.3337 0.4245 11.00000 0.05 0.77 Q10 1 0.6688 0.6042 0.4073 11.00000 0.05 0.73 Q11 1 0.7607 0.1418 0.4099 11.00000 0.05 0.67 Q12 1 0.7089 0.5803 0.4211 11.00000 0.05 0.66 Q13 1 0.7486 0.2965 0.4277 11.00000 0.05 0.64 Q14 1 0.6884 0.5659 0.4766 11.00000 0.05 0.63 Q15 1 0.7107 1.1128 0.4471 11.00000 0.05 0.62 Q16 1 0.7065 0.8689 0.4723 11.00000 0.05 0.61 Q17 1 0.6385 0.1755 0.3614 11.00000 0.05 0.61 Q18 1 0.6620 0.7026 0.4535 11.00000 0.05 0.60 Q19 1 0.6676 1.0406 0.4290 11.00000 0.05 0.58 Q20 1 0.7317 0.4314 0.4236 11.00000 0.05 0.57 ; _shelx_res_checksum 48790 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp Bi1 Bi 0.70789(2) 0.45697(3) 0.42416(2) 0.01252(6) Uani 1 1 d . . Br1 Br 0.70794(2) 0.87199(8) 0.43164(2) 0.01792(11) Uani 1 1 d . . C1 C 0.76225(18) 0.4312(7) 0.3429(2) 0.0116(9) Uani 1 1 d . . H1A H 0.7390 0.4064 0.3048 0.014 Uiso 1 1 calc R U C2 C 0.7982(2) 0.2422(7) 0.3517(2) 0.0130(11) Uani 1 1 d . . H2A H 0.7765 0.1178 0.3608 0.016 Uiso 1 1 calc R U C3 C 0.8399(2) 0.2790(8) 0.4053(2) 0.0173(11) Uani 1 1 d . . H3A H 0.8221 0.3014 0.4441 0.021 Uiso 1 1 calc R U H3B H 0.8629 0.1558 0.4107 0.021 Uiso 1 1 calc R U C4 C 0.87339(19) 0.4686(8) 0.3914(2) 0.0179(10) Uani 1 1 d . . H4A H 0.9003 0.4923 0.4262 0.021 Uiso 1 1 calc R U C5 C 0.90144(19) 0.4317(8) 0.3318(2) 0.0187(11) Uani 1 1 d . . H5A H 0.9247 0.3091 0.3367 0.022 Uiso 1 1 calc R U H5B H 0.9236 0.5529 0.3230 0.022 Uiso 1 1 calc R U C6 C 0.86025(19) 0.3967(7) 0.2777(2) 0.0145(10) Uani 1 1 d . . H6A H 0.8784 0.3737 0.2387 0.017 Uiso 1 1 calc R U C7 C 0.82361(19) 0.5876(7) 0.2709(2) 0.0138(10) Uani 1 1 d . . H7A H 0.8447 0.7114 0.2616 0.017 Uiso 1 1 calc R U H7B H 0.7970 0.5656 0.2364 0.017 Uiso 1 1 calc R U C8 C 0.79562(19) 0.6228(7) 0.3310(2) 0.0131(10) Uani 1 1 d . . H8A H 0.7721 0.7466 0.3262 0.016 Uiso 1 1 calc R U C9 C 0.8267(2) 0.2064(8) 0.2922(2) 0.0171(11) Uani 1 1 d . . H9A H 0.8004 0.1806 0.2576 0.020 Uiso 1 1 calc R U H9B H 0.8497 0.0831 0.2970 0.020 Uiso 1 1 calc R U C10 C 0.8372(2) 0.6596(7) 0.3837(2) 0.0165(11) Uani 1 1 d . . H10A H 0.8196 0.6853 0.4224 0.020 Uiso 1 1 calc R U H10B H 0.8585 0.7830 0.3747 0.020 Uiso 1 1 calc R U C11 C 0.62979(17) 0.4523(8) 0.3634(2) 0.0127(9) Uani 1 1 d . . H11A H 0.6384 0.4777 0.3198 0.015 Uiso 1 1 calc R U C12 C 0.59024(19) 0.6175(7) 0.3815(2) 0.0142(10) Uani 1 1 d . . H12A H 0.6071 0.7571 0.3797 0.017 Uiso 1 1 calc R U C13 C 0.5417(2) 0.6103(8) 0.3362(2) 0.0177(11) Uani 1 1 d . . H13A H 0.5162 0.7180 0.3471 0.021 Uiso 1 1 calc R U H13B H 0.5525 0.6390 0.2940 0.021 Uiso 1 1 calc R U C14 C 0.5157(2) 0.3979(8) 0.3380(2) 0.0165(11) Uani 1 1 d . . H14A H 0.4843 0.3942 0.3080 0.020 Uiso 1 1 calc R U C15 C 0.4978(2) 0.3578(8) 0.4038(2) 0.0192(11) Uani 1 1 d . . H15A H 0.4720 0.4644 0.4148 0.023 Uiso 1 1 calc R U H15B H 0.4806 0.2206 0.4056 0.023 Uiso 1 1 calc R U C16 C 0.5463(2) 0.3653(7) 0.4493(2) 0.0162(11) Uani 1 1 d . . H16A H 0.5352 0.3389 0.4920 0.019 Uiso 1 1 calc R U C17 C 0.5858(2) 0.1968(8) 0.4315(2) 0.0157(11) Uani 1 1 d . . H17A H 0.6167 0.1968 0.4615 0.019 Uiso 1 1 calc R U H17B H 0.5688 0.0592 0.4328 0.019 Uiso 1 1 calc R U C18 C 0.6039(2) 0.2375(7) 0.3669(2) 0.0126(11) Uani 1 1 d . . H18A H 0.6296 0.1285 0.3558 0.015 Uiso 1 1 calc R U C19 C 0.5550(2) 0.2313(7) 0.3211(2) 0.0146(11) Uani 1 1 d . . H19A H 0.5660 0.2552 0.2788 0.018 Uiso 1 1 calc R U H19B H 0.5381 0.0935 0.3224 0.018 Uiso 1 1 calc R U C20 C 0.5729(2) 0.5785(7) 0.4468(2) 0.0167(11) Uani 1 1 d . . H20A H 0.5479 0.6875 0.4582 0.020 Uiso 1 1 calc R U H20B H 0.6041 0.5831 0.4765 0.020 Uiso 1 1 calc R U 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 Bi1 0.00970(9) 0.01469(9) 0.01329(9) 0.00120(8) 0.00177(6) -0.00071(8) Br1 0.0159(3) 0.0152(2) 0.0226(3) -0.00164(19) 0.0007(2) -0.0010(2) C1 0.009(2) 0.014(3) 0.012(2) -0.0015(18) 0.0025(18) 0.0017(19) C2 0.013(3) 0.010(3) 0.017(3) 0.0022(18) 0.003(2) -0.0020(18) C3 0.018(3) 0.018(3) 0.016(3) 0.007(2) 0.001(2) 0.001(2) C4 0.010(2) 0.024(3) 0.019(2) 0.002(2) -0.0016(19) -0.005(2) C5 0.008(2) 0.023(3) 0.025(3) 0.005(2) 0.003(2) -0.002(2) C6 0.012(3) 0.015(3) 0.018(2) 0.0016(19) 0.006(2) 0.0015(19) C7 0.015(3) 0.011(3) 0.016(2) 0.0018(18) 0.0032(19) 0.0005(19) C8 0.012(3) 0.011(2) 0.016(2) 0.0016(18) 0.002(2) 0.0043(19) C9 0.017(3) 0.015(2) 0.020(3) -0.003(2) 0.005(2) 0.000(2) C10 0.016(3) 0.014(3) 0.020(3) -0.001(2) 0.003(2) -0.005(2) C11 0.008(2) 0.020(2) 0.010(2) 0.003(2) -0.0009(17) 0.001(2) C12 0.010(3) 0.009(2) 0.024(3) -0.003(2) 0.005(2) -0.0036(18) C13 0.012(3) 0.014(3) 0.027(3) 0.004(2) -0.001(2) 0.0018(19) C14 0.013(3) 0.019(3) 0.018(2) -0.002(2) 0.002(2) 0.001(2) C15 0.013(3) 0.015(3) 0.030(3) -0.005(2) 0.007(2) -0.005(2) C16 0.015(3) 0.018(3) 0.016(2) -0.003(2) 0.009(2) -0.003(2) C17 0.016(3) 0.015(3) 0.016(2) 0.003(2) 0.003(2) -0.007(2) C18 0.011(3) 0.008(3) 0.018(3) -0.0007(18) 0.002(2) 0.0031(17) C19 0.011(3) 0.016(3) 0.016(3) -0.0021(19) -0.001(2) -0.0040(19) C20 0.017(3) 0.012(3) 0.022(3) -0.008(2) 0.004(2) -0.004(2) 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' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C1 Bi1 C11 95.28(16) C1 Bi1 Br1 96.90(12) C11 Bi1 Br1 92.57(12) C2 C1 C8 109.6(4) C2 C1 Bi1 109.8(3) C8 C1 Bi1 115.6(3) C2 C1 H1A 107.1 C8 C1 H1A 107.1 Bi1 C1 H1A 107.1 C1 C2 C9 108.7(4) C1 C2 C3 110.4(4) C9 C2 C3 108.8(4) C1 C2 H2A 109.6 C9 C2 H2A 109.6 C3 C2 H2A 109.6 C4 C3 C2 109.7(4) C4 C3 H3A 109.7 C2 C3 H3A 109.7 C4 C3 H3B 109.7 C2 C3 H3B 109.7 H3A C3 H3B 108.2 C3 C4 C5 109.4(4) C3 C4 C10 109.2(4) C5 C4 C10 109.6(4) C3 C4 H4A 109.5 C5 C4 H4A 109.5 C10 C4 H4A 109.5 C4 C5 C6 109.8(4) C4 C5 H5A 109.7 C6 C5 H5A 109.7 C4 C5 H5B 109.7 C6 C5 H5B 109.7 H5A C5 H5B 108.2 C9 C6 C5 108.7(4) C9 C6 C7 108.8(4) C5 C6 C7 109.4(4) C9 C6 H6A 110.0 C5 C6 H6A 110.0 C7 C6 H6A 110.0 C8 C7 C6 110.0(4) C8 C7 H7A 109.7 C6 C7 H7A 109.7 C8 C7 H7B 109.7 C6 C7 H7B 109.7 H7A C7 H7B 108.2 C10 C8 C1 111.3(4) C10 C8 C7 109.1(4) C1 C8 C7 108.1(4) C10 C8 H8A 109.4 C1 C8 H8A 109.4 C7 C8 H8A 109.4 C2 C9 C6 110.2(4) C2 C9 H9A 109.6 C6 C9 H9A 109.6 C2 C9 H9B 109.6 C6 C9 H9B 109.6 H9A C9 H9B 108.1 C8 C10 C4 109.6(4) C8 C10 H10A 109.7 C4 C10 H10A 109.7 C8 C10 H10B 109.7 C4 C10 H10B 109.7 H10A C10 H10B 108.2 C12 C11 C18 109.1(4) C12 C11 Bi1 113.3(3) C18 C11 Bi1 109.7(3) C12 C11 H11A 108.2 C18 C11 H11A 108.2 Bi1 C11 H11A 108.2 C20 C12 C13 109.2(4) C20 C12 C11 110.5(4) C13 C12 C11 109.1(4) C20 C12 H12A 109.3 C13 C12 H12A 109.3 C11 C12 H12A 109.3 C14 C13 C12 110.1(4) C14 C13 H13A 109.6 C12 C13 H13A 109.6 C14 C13 H13B 109.6 C12 C13 H13B 109.6 H13A C13 H13B 108.2 C13 C14 C19 109.8(4) C13 C14 C15 109.0(4) C19 C14 C15 109.6(4) C13 C14 H14A 109.5 C19 C14 H14A 109.5 C15 C14 H14A 109.5 C16 C15 C14 108.9(4) C16 C15 H15A 109.9 C14 C15 H15A 109.9 C16 C15 H15B 109.9 C14 C15 H15B 109.9 H15A C15 H15B 108.3 C15 C16 C20 110.0(4) C15 C16 C17 108.9(4) C20 C16 C17 109.3(4) C15 C16 H16A 109.5 C20 C16 H16A 109.5 C17 C16 H16A 109.5 C18 C17 C16 110.1(4) C18 C17 H17A 109.6 C16 C17 H17A 109.6 C18 C17 H17B 109.6 C16 C17 H17B 109.6 H17A C17 H17B 108.2 C17 C18 C11 110.6(4) C17 C18 C19 108.4(4) C11 C18 C19 108.7(4) C17 C18 H18A 109.7 C11 C18 H18A 109.7 C19 C18 H18A 109.7 C14 C19 C18 109.7(4) C14 C19 H19A 109.7 C18 C19 H19A 109.7 C14 C19 H19B 109.7 C18 C19 H19B 109.7 H19A C19 H19B 108.2 C12 C20 C16 109.4(4) C12 C20 H20A 109.8 C16 C20 H20A 109.8 C12 C20 H20B 109.8 C16 C20 H20B 109.8 H20A C20 H20B 108.2 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Bi1 C1 2.310(5) Bi1 C11 2.315(4) Bi1 Br1 2.6879(6) C1 C2 1.530(6) C1 C8 1.531(7) C1 H1A 1.0000 C2 C9 1.537(7) C2 C3 1.545(7) C2 H2A 1.0000 C3 C4 1.532(7) C3 H3A 0.9900 C3 H3B 0.9900 C4 C5 1.534(7) C4 C10 1.542(7) C4 H4A 1.0000 C5 C6 1.542(6) C5 H5A 0.9900 C5 H5B 0.9900 C6 C9 1.538(7) C6 C7 1.547(6) C6 H6A 1.0000 C7 C8 1.539(6) C7 H7A 0.9900 C7 H7B 0.9900 C8 C10 1.530(7) C8 H8A 1.0000 C9 H9A 0.9900 C9 H9B 0.9900 C10 H10A 0.9900 C10 H10B 0.9900 C11 C12 1.532(7) C11 C18 1.540(7) C11 H11A 1.0000 C12 C20 1.530(7) C12 C13 1.531(7) C12 H12A 1.0000 C13 C14 1.526(7) C13 H13A 0.9900 C13 H13B 0.9900 C14 C19 1.527(7) C14 C15 1.547(7) C14 H14A 1.0000 C15 C16 1.532(7) C15 H15A 0.9900 C15 H15B 0.9900 C16 C20 1.538(7) C16 C17 1.545(7) C16 H16A 1.0000 C17 C18 1.526(7) C17 H17A 0.9900 C17 H17B 0.9900 C18 C19 1.542(7) C18 H18A 1.0000 C19 H19A 0.9900 C19 H19B 0.9900 C20 H20A 0.9900 C20 H20B 0.9900 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 C8 C1 C2 C9 -61.9(5) Bi1 C1 C2 C9 170.1(3) C8 C1 C2 C3 57.4(5) Bi1 C1 C2 C3 -70.6(4) C1 C2 C3 C4 -59.5(6) C9 C2 C3 C4 59.7(5) C2 C3 C4 C5 -60.1(5) C2 C3 C4 C10 59.9(5) C3 C4 C5 C6 60.4(5) C10 C4 C5 C6 -59.4(5) C4 C5 C6 C9 -60.0(5) C4 C5 C6 C7 58.6(5) C9 C6 C7 C8 59.4(5) C5 C6 C7 C8 -59.1(5) C2 C1 C8 C10 -57.5(5) Bi1 C1 C8 C10 67.2(4) C2 C1 C8 C7 62.2(5) Bi1 C1 C8 C7 -173.0(3) C6 C7 C8 C10 60.1(5) C6 C7 C8 C1 -61.0(5) C1 C2 C9 C6 60.2(5) C3 C2 C9 C6 -60.1(5) C5 C6 C9 C2 60.2(5) C7 C6 C9 C2 -58.8(5) C1 C8 C10 C4 58.6(5) C7 C8 C10 C4 -60.6(5) C3 C4 C10 C8 -59.4(5) C5 C4 C10 C8 60.5(5) C18 C11 C12 C20 59.0(5) Bi1 C11 C12 C20 -63.6(4) C18 C11 C12 C13 -61.0(5) Bi1 C11 C12 C13 176.4(3) C20 C12 C13 C14 -60.7(5) C11 C12 C13 C14 60.1(5) C12 C13 C14 C19 -59.3(5) C12 C13 C14 C15 60.8(5) C13 C14 C15 C16 -59.9(5) C19 C14 C15 C16 60.3(5) C14 C15 C16 C20 59.8(5) C14 C15 C16 C17 -59.9(5) C15 C16 C17 C18 61.3(5) C20 C16 C17 C18 -58.9(5) C16 C17 C18 C11 58.5(5) C16 C17 C18 C19 -60.6(5) C12 C11 C18 C17 -58.0(5) Bi1 C11 C18 C17 66.7(4) C12 C11 C18 C19 60.9(5) Bi1 C11 C18 C19 -174.3(3) C13 C14 C19 C18 59.3(5) C15 C14 C19 C18 -60.5(5) C17 C18 C19 C14 60.3(5) C11 C18 C19 C14 -60.0(5) C13 C12 C20 C16 59.5(5) C11 C12 C20 C16 -60.4(5) C15 C16 C20 C12 -59.9(5) C17 C16 C20 C12 59.6(5)