#------------------------------------------------------------------------------ #$Date: 2020-04-21 04:57:05 +0300 (Tue, 21 Apr 2020) $ #$Revision: 250973 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/03/7240352.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_7240352 loop_ _publ_author_name 'Mehring, Michael' 'Preda, Ana Maria' 'Scholz, Sebastian' 'Krasowska, Malgorzata' 'Bhattacharyya, Kalishankar' 'Toma, Ana Maria' 'Silvestru, Cristian' 'Korb, Marcus' 'Rueffer, Tobias' 'Lang, Heinrich' 'Auer, Alexander A.' _publ_section_title ; Evaluation of bismuth-based dispersion energy donors -- synthesis, structure and theoretical study of 2-biphenylbismuth(III) derivatives ; _journal_name_full 'Physical Chemistry Chemical Physics' _journal_paper_doi 10.1039/C9CP06924K _journal_year 2020 _chemical_formula_moiety 'C24 H18 Bi I' _chemical_formula_sum 'C24 H19 Bi I' _chemical_formula_weight 643.27 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2013 _audit_update_record ; 2020-04-16 deposited with the CCDC. 2020-04-20 downloaded from the CCDC. ; _cell_angle_alpha 108.743(3) _cell_angle_beta 99.713(3) _cell_angle_gamma 103.712(3) _cell_formula_units_Z 2 _cell_length_a 9.3194(9) _cell_length_b 9.6034(9) _cell_length_c 12.8339(12) _cell_measurement_reflns_used 9873 _cell_measurement_temperature 100 _cell_measurement_theta_max 31.5399 _cell_measurement_theta_min 3.1087 _cell_volume 1018.57(17) _computing_cell_refinement 'SAINT V8.38A (Bruker AXS Inc., 2017)' _computing_data_collection 'bruker instrument service APEX3v2017.3-0' _computing_data_reduction 'SAINT V8.38A (Bruker AXS Inc., 2017)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_structure_solution 'SHELXS-2013 (Sheldrick, 2013)' _diffrn_ambient_temperature 100 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'bruker venture d8' _diffrn_measurement_method '\w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0443 _diffrn_reflns_av_unetI/netI 0.0314 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 15873 _diffrn_reflns_point_group_measured_fraction_full 0.995 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_theta_full 25.000 _diffrn_reflns_theta_max 24.997 _diffrn_reflns_theta_min 3.396 _exptl_absorpt_coefficient_mu 10.174 _exptl_absorpt_correction_T_max 0.14 _exptl_absorpt_correction_T_min 0.04 _exptl_absorpt_correction_type 'Numerical Mu From Formula' _exptl_absorpt_process_details ; SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction ; _exptl_crystal_colour 'clear light yellow' _exptl_crystal_density_diffrn 2.097 _exptl_crystal_description block _exptl_crystal_F_000 598 _exptl_crystal_size_max 0.416 _exptl_crystal_size_mid 0.347 _exptl_crystal_size_min 0.312 _refine_diff_density_max 4.718 _refine_diff_density_min -1.012 _refine_diff_density_rms 0.260 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 235 _refine_ls_number_reflns 3558 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.087 _refine_ls_R_factor_all 0.0545 _refine_ls_R_factor_gt 0.0526 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0850P)^2^+8.8108P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1411 _refine_ls_wR_factor_ref 0.1427 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3356 _reflns_number_total 3558 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cp06924k2.cif _cod_data_source_block shelx_CCDC2 _cod_database_code 7240352 _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. ; _shelxl_version_number 2013-4 _shelx_res_file ; TITL mo_AP423_0m_a.res in P-1 CELL 0.71073 9.3194 9.6034 12.8339 108.743 99.713 103.712 ZERR 2.00 0.0009 0.0009 0.0012 0.003 0.003 0.003 LATT 1 SFAC C H BI I UNIT 48 38 2 2 MERG 2 OMIT 0.00 50.00 OMIT -1 1 0 OMIT -5 -9 6 OMIT 0 1 1 OMIT -1 0 1 OMIT -2 -9 5 OMIT -8 -5 6 OMIT 1 -1 1 OMIT -6 -10 5 OMIT 7 -9 13 OMIT -4 -9 6 OMIT -5 -4 13 OMIT -3 -7 12 OMIT 1 -11 4 FMAP 2 PLAN 20 ACTA 50.00 BOND $H CONF L.S. 10 TEMP -173.15 WGHT 0.085000 8.810801 FVAR 0.30766 C1 1 0.261455 0.839412 0.180304 11.00000 0.04060 0.03958 = 0.04996 0.01336 0.01138 0.01387 C2 1 0.262100 0.908114 0.100652 11.00000 0.04630 0.04637 = 0.05193 0.02290 0.02058 0.01919 AFIX 43 H2 2 0.356172 0.970293 0.097871 11.00000 -1.20000 AFIX 0 C3 1 0.129385 0.887301 0.026538 11.00000 0.06069 0.05967 = 0.05007 0.02722 0.01645 0.02911 AFIX 43 H3 2 0.131425 0.933616 -0.028635 11.00000 -1.20000 AFIX 0 C4 1 -0.011035 0.797922 0.030587 11.00000 0.05016 0.05047 = 0.04968 0.01942 0.01374 0.01982 AFIX 43 H4 2 -0.103820 0.786230 -0.020248 11.00000 -1.20000 AFIX 0 C5 1 -0.013830 0.728700 0.106855 11.00000 0.04212 0.04529 = 0.04876 0.01844 0.01205 0.01333 AFIX 43 H5 2 -0.108543 0.665070 0.107491 11.00000 -1.20000 AFIX 0 C6 1 0.122260 0.749787 0.185585 11.00000 0.04340 0.03676 = 0.04756 0.01686 0.01209 0.01777 C7 1 0.116185 0.671909 0.269292 11.00000 0.04127 0.04691 = 0.05551 0.02656 0.02214 0.02080 C8 1 0.046690 0.514360 0.232247 11.00000 0.04221 0.05179 = 0.06130 0.02514 0.01707 0.01879 AFIX 43 H8 2 -0.006491 0.456648 0.154153 11.00000 -1.20000 AFIX 0 C9 1 0.054019 0.440366 0.307866 11.00000 0.05374 0.05693 = 0.07124 0.03368 0.02382 0.02078 AFIX 43 H9 2 0.008831 0.331408 0.281671 11.00000 -1.20000 AFIX 0 C10 1 0.127845 0.525810 0.422734 11.00000 0.04970 0.07588 = 0.06675 0.04871 0.03019 0.02947 AFIX 43 H10 2 0.135300 0.473692 0.474076 11.00000 -1.20000 AFIX 0 C11 1 0.185199 0.671197 0.460284 11.00000 0.02881 0.08602 = 0.03860 0.03326 0.02338 0.02243 AFIX 43 H11 2 0.231652 0.726437 0.539705 11.00000 -1.20000 AFIX 0 C12 1 0.181747 0.756042 0.384653 11.00000 0.04294 0.04973 = 0.05930 0.02698 0.02834 0.02099 AFIX 43 H12 2 0.223186 0.865638 0.413611 11.00000 -1.20000 AFIX 0 C13 1 0.481666 0.631042 0.233850 11.00000 0.04388 0.04233 = 0.05016 0.02009 0.01639 0.01241 C14 1 0.399927 0.536074 0.123418 11.00000 0.04271 0.04939 = 0.05163 0.02127 0.01297 0.01391 AFIX 43 H14 2 0.328967 0.568584 0.082058 11.00000 -1.20000 AFIX 0 C15 1 0.419810 0.393257 0.071606 11.00000 0.05050 0.04367 = 0.05519 0.02143 0.01450 0.01875 AFIX 43 H15 2 0.363726 0.328549 -0.004807 11.00000 -1.20000 AFIX 0 C16 1 0.524912 0.346031 0.134604 11.00000 0.04649 0.05784 = 0.06123 0.02569 0.02210 0.02500 AFIX 43 H16 2 0.539426 0.248479 0.100889 11.00000 -1.20000 AFIX 0 C17 1 0.605489 0.440898 0.243974 11.00000 0.05294 0.04561 = 0.06253 0.01701 0.01403 0.02177 AFIX 43 H17 2 0.677178 0.408885 0.285128 11.00000 -1.20000 AFIX 0 C18 1 0.585154 0.583837 0.296865 11.00000 0.03686 0.04771 = 0.05336 0.01974 0.01559 0.01692 C19 1 0.670896 0.683433 0.416996 11.00000 0.04335 0.03909 = 0.05526 0.01780 0.01121 0.01843 C20 1 0.599091 0.692420 0.504831 11.00000 0.04669 0.04892 = 0.06022 0.02254 0.01837 0.02426 AFIX 43 H20 2 0.493621 0.636486 0.487237 11.00000 -1.20000 AFIX 0 C21 1 0.680039 0.782353 0.618010 11.00000 0.05651 0.05183 = 0.05612 0.02606 0.02297 0.02683 AFIX 43 H21 2 0.630197 0.786455 0.677184 11.00000 -1.20000 AFIX 0 C22 1 0.835374 0.866903 0.644479 11.00000 0.05857 0.04977 = 0.05204 0.02243 0.01218 0.02604 AFIX 43 H22 2 0.891407 0.929902 0.721221 11.00000 -1.20000 AFIX 0 C23 1 0.904327 0.856779 0.557697 11.00000 0.04762 0.05095 = 0.05661 0.02540 0.00845 0.01803 AFIX 43 H23 2 1.009855 0.912382 0.575090 11.00000 -1.20000 AFIX 0 C24 1 0.824383 0.767472 0.444836 11.00000 0.04270 0.04384 = 0.06147 0.02014 0.01450 0.01877 AFIX 43 H24 2 0.875187 0.763887 0.386221 11.00000 -1.20000 AFIX 0 BI1 3 0.473022 0.873298 0.313798 11.00000 0.04256 0.04325 = 0.04421 0.01810 0.01291 0.01661 AFIX 43 HI1 2 0.535931 0.959465 0.380165 11.00000 -1.20000 AFIX 0 I1 4 0.685776 0.999855 0.203712 11.00000 0.04468 0.04793 = 0.05264 0.01968 0.01650 0.01298 HKLF 4 REM mo_AP423_0m_a.res in P-1 REM R1 = 0.0526 for 3356 Fo > 4sig(Fo) and 0.0545 for all 3558 data REM 235 parameters refined using 0 restraints END WGHT 0.0848 8.8363 REM Highest difference peak 4.718, deepest hole -1.012, 1-sigma level 0.260 Q1 1 0.3970 0.7841 0.3725 11.00000 0.05 4.72 Q2 1 0.4377 0.8463 0.2381 11.00000 0.05 3.06 Q3 1 0.5075 0.9059 0.3948 11.00000 0.05 2.94 Q4 1 0.5187 0.9801 0.3438 11.00000 0.05 2.12 Q5 1 0.4250 0.7705 0.2737 11.00000 0.05 2.02 Q6 1 0.7261 1.0375 0.2849 11.00000 0.05 2.01 Q7 1 0.6497 0.9658 0.1194 11.00000 0.05 2.00 Q8 1 0.7278 1.1021 0.2412 11.00000 0.05 1.47 Q9 1 0.1795 0.6395 0.4772 11.00000 0.05 1.47 Q10 1 0.6515 0.9011 0.1737 11.00000 0.05 1.46 Q11 1 0.4623 0.3674 0.1109 11.00000 0.05 0.98 Q12 1 0.2417 0.7261 0.4362 11.00000 0.05 0.87 Q13 1 0.5510 0.8833 0.2927 11.00000 0.05 0.83 Q14 1 0.5570 0.3625 0.0748 11.00000 0.05 0.74 Q15 1 0.3862 0.8628 0.3206 11.00000 0.05 0.70 Q16 1 0.4494 0.3566 0.2766 11.00000 0.05 0.65 Q17 1 0.3748 0.2827 0.0811 11.00000 0.05 0.57 Q18 1 0.8776 0.8523 0.5033 11.00000 0.05 0.53 Q19 1 0.3719 0.5528 -0.0548 11.00000 0.05 0.53 Q20 1 0.0856 0.6789 0.2041 11.00000 0.05 0.53 ; _shelx_res_checksum 18161 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2615(12) 0.8394(12) 0.1803(9) 0.044(2) Uani 1 1 d . . . . . C2 C 0.2621(13) 0.9081(13) 0.1007(9) 0.045(2) Uani 1 1 d . . . . . H2 H 0.3562 0.9703 0.0979 0.054 Uiso 1 1 calc R U . . . C3 C 0.1294(15) 0.8873(15) 0.0265(10) 0.053(3) Uani 1 1 d . . . . . H3 H 0.1314 0.9336 -0.0286 0.064 Uiso 1 1 calc R U . . . C4 C -0.0110(14) 0.7979(14) 0.0306(10) 0.049(3) Uani 1 1 d . . . . . H4 H -0.1038 0.7862 -0.0202 0.059 Uiso 1 1 calc R U . . . C5 C -0.0138(13) 0.7287(13) 0.1069(9) 0.045(2) Uani 1 1 d . . . . . H5 H -0.1085 0.6651 0.1075 0.054 Uiso 1 1 calc R U . . . C6 C 0.1223(12) 0.7498(12) 0.1856(9) 0.041(2) Uani 1 1 d . . . . . C7 C 0.1162(12) 0.6719(13) 0.2693(10) 0.043(2) Uani 1 1 d . . . . . C8 C 0.0467(13) 0.5144(14) 0.2322(11) 0.050(3) Uani 1 1 d . . . . . H8 H -0.0065 0.4566 0.1542 0.059 Uiso 1 1 calc R U . . . C9 C 0.0540(15) 0.4404(15) 0.3079(12) 0.057(3) Uani 1 1 d . . . . . H9 H 0.0088 0.3314 0.2817 0.068 Uiso 1 1 calc R U . . . C10 C 0.1278(14) 0.5258(16) 0.4227(11) 0.055(3) Uani 1 1 d . . . . . H10 H 0.1353 0.4737 0.4741 0.066 Uiso 1 1 calc R U . . . C11 C 0.1852(11) 0.6712(16) 0.4603(9) 0.046(3) Uani 1 1 d . . . . . H11 H 0.2317 0.7264 0.5397 0.055 Uiso 1 1 calc R U . . . C12 C 0.1817(12) 0.7560(13) 0.3847(10) 0.046(2) Uani 1 1 d . . . . . H12 H 0.2232 0.8656 0.4136 0.055 Uiso 1 1 calc R U . . . C13 C 0.4817(12) 0.6310(12) 0.2338(9) 0.044(2) Uani 1 1 d . . . . . C14 C 0.3999(13) 0.5361(13) 0.1234(10) 0.047(2) Uani 1 1 d . . . . . H14 H 0.3290 0.5686 0.0821 0.057 Uiso 1 1 calc R U . . . C15 C 0.4198(13) 0.3933(13) 0.0716(10) 0.048(2) Uani 1 1 d . . . . . H15 H 0.3637 0.3285 -0.0048 0.058 Uiso 1 1 calc R U . . . C16 C 0.5249(13) 0.3460(15) 0.1346(11) 0.052(3) Uani 1 1 d . . . . . H16 H 0.5394 0.2485 0.1009 0.062 Uiso 1 1 calc R U . . . C17 C 0.6055(14) 0.4409(13) 0.2440(11) 0.054(3) Uani 1 1 d . . . . . H17 H 0.6772 0.4089 0.2851 0.064 Uiso 1 1 calc R U . . . C18 C 0.5852(12) 0.5838(13) 0.2969(10) 0.045(2) Uani 1 1 d . . . . . C19 C 0.6709(12) 0.6834(12) 0.4170(10) 0.045(2) Uani 1 1 d . . . . . C20 C 0.5991(13) 0.6924(13) 0.5048(10) 0.049(3) Uani 1 1 d . . . . . H20 H 0.4936 0.6365 0.4872 0.059 Uiso 1 1 calc R U . . . C21 C 0.6800(14) 0.7824(13) 0.6180(10) 0.050(3) Uani 1 1 d . . . . . H21 H 0.6302 0.7865 0.6772 0.061 Uiso 1 1 calc R U . . . C22 C 0.8354(14) 0.8669(14) 0.6445(10) 0.051(3) Uani 1 1 d . . . . . H22 H 0.8914 0.9299 0.7212 0.061 Uiso 1 1 calc R U . . . C23 C 0.9043(14) 0.8568(14) 0.5577(10) 0.051(3) Uani 1 1 d . . . . . H23 H 1.0099 0.9124 0.5751 0.061 Uiso 1 1 calc R U . . . C24 C 0.8244(13) 0.7675(13) 0.4448(10) 0.048(2) Uani 1 1 d . . . . . H24 H 0.8752 0.7639 0.3862 0.058 Uiso 1 1 calc R U . . . Bi1 Bi 0.47302(4) 0.87330(4) 0.31380(3) 0.04214(18) Uani 1 1 d . . . . . HI1 H 0.5359 0.9595 0.3802 0.051 Uiso 1 1 calc R U . . . I1 I 0.68578(8) 0.99986(8) 0.20371(6) 0.0480(2) 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 C1 0.041(5) 0.040(5) 0.050(6) 0.013(5) 0.011(4) 0.014(4) C2 0.046(6) 0.046(6) 0.052(6) 0.023(5) 0.021(5) 0.019(5) C3 0.061(7) 0.060(7) 0.050(6) 0.027(5) 0.016(5) 0.029(6) C4 0.050(6) 0.050(6) 0.050(6) 0.019(5) 0.014(5) 0.020(5) C5 0.042(6) 0.045(6) 0.049(6) 0.018(5) 0.012(5) 0.013(5) C6 0.043(5) 0.037(5) 0.048(6) 0.017(4) 0.012(4) 0.018(4) C7 0.041(5) 0.047(6) 0.056(6) 0.027(5) 0.022(5) 0.021(5) C8 0.042(6) 0.052(6) 0.061(7) 0.025(5) 0.017(5) 0.019(5) C9 0.054(7) 0.057(7) 0.071(8) 0.034(6) 0.024(6) 0.021(6) C10 0.050(6) 0.076(9) 0.067(7) 0.049(7) 0.030(6) 0.029(6) C11 0.029(5) 0.086(9) 0.039(5) 0.033(5) 0.023(4) 0.022(5) C12 0.043(6) 0.050(6) 0.059(7) 0.027(5) 0.028(5) 0.021(5) C13 0.044(6) 0.042(6) 0.050(6) 0.020(5) 0.016(5) 0.012(5) C14 0.043(6) 0.049(6) 0.052(6) 0.021(5) 0.013(5) 0.014(5) C15 0.051(6) 0.044(6) 0.055(6) 0.021(5) 0.014(5) 0.019(5) C16 0.046(6) 0.058(7) 0.061(7) 0.026(6) 0.022(5) 0.025(5) C17 0.053(7) 0.046(6) 0.063(7) 0.017(5) 0.014(5) 0.022(5) C18 0.037(5) 0.048(6) 0.053(6) 0.020(5) 0.016(5) 0.017(4) C19 0.043(6) 0.039(5) 0.055(6) 0.018(5) 0.011(5) 0.018(4) C20 0.047(6) 0.049(6) 0.060(7) 0.023(5) 0.018(5) 0.024(5) C21 0.057(7) 0.052(6) 0.056(7) 0.026(5) 0.023(5) 0.027(5) C22 0.059(7) 0.050(6) 0.052(6) 0.022(5) 0.012(5) 0.026(5) C23 0.048(6) 0.051(6) 0.057(7) 0.025(5) 0.008(5) 0.018(5) C24 0.043(6) 0.044(6) 0.061(7) 0.020(5) 0.015(5) 0.019(5) Bi1 0.0426(3) 0.0433(3) 0.0442(3) 0.01810(18) 0.01291(17) 0.01661(18) I1 0.0447(4) 0.0479(4) 0.0526(4) 0.0197(3) 0.0165(3) 0.0130(3) 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' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 119.7(10) . . ? C2 C1 Bi1 124.0(8) . . ? C6 C1 Bi1 116.2(8) . . ? C3 C2 C1 120.4(11) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 120.6(11) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C5 C4 C3 119.8(11) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 120.7(11) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C1 C6 C5 118.7(10) . . ? C1 C6 C7 121.6(10) . . ? C5 C6 C7 119.7(10) . . ? C8 C7 C12 119.0(10) . . ? C8 C7 C6 120.4(10) . . ? C12 C7 C6 120.6(10) . . ? C9 C8 C7 120.3(12) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C8 C9 C10 119.7(12) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? C11 C10 C9 121.4(11) . . ? C11 C10 H10 119.3 . . ? C9 C10 H10 119.3 . . ? C10 C11 C12 121.5(11) . . ? C10 C11 H11 119.3 . . ? C12 C11 H11 119.3 . . ? C7 C12 C11 117.8(10) . . ? C7 C12 H12 121.1 . . ? C11 C12 H12 121.1 . . ? C14 C13 C18 120.3(10) . . ? C14 C13 Bi1 122.0(8) . . ? C18 C13 Bi1 117.4(8) . . ? C13 C14 C15 120.9(11) . . ? C13 C14 H14 119.5 . . ? C15 C14 H14 119.5 . . ? C14 C15 C16 118.8(11) . . ? C14 C15 H15 120.6 . . ? C16 C15 H15 120.6 . . ? C17 C16 C15 119.8(11) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C16 C17 C18 121.6(11) . . ? C16 C17 H17 119.2 . . ? C18 C17 H17 119.2 . . ? C17 C18 C13 118.4(11) . . ? C17 C18 C19 120.8(10) . . ? C13 C18 C19 120.8(10) . . ? C24 C19 C20 118.4(11) . . ? C24 C19 C18 121.0(10) . . ? C20 C19 C18 120.6(10) . . ? C21 C20 C19 120.8(11) . . ? C21 C20 H20 119.6 . . ? C19 C20 H20 119.6 . . ? C20 C21 C22 119.9(11) . . ? C20 C21 H21 120.1 . . ? C22 C21 H21 120.1 . . ? C23 C22 C21 118.7(11) . . ? C23 C22 H22 120.7 . . ? C21 C22 H22 120.7 . . ? C22 C23 C24 121.7(12) . . ? C22 C23 H23 119.1 . . ? C24 C23 H23 119.1 . . ? C19 C24 C23 120.4(11) . . ? C19 C24 H24 119.8 . . ? C23 C24 H24 119.8 . . ? C13 Bi1 C1 94.9(4) . . ? C13 Bi1 I1 93.9(3) . . ? C1 Bi1 I1 94.7(3) . . ? C13 Bi1 HI1 132.6 . . ? C1 Bi1 HI1 132.6 . . ? I1 Bi1 HI1 83.6 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.383(16) . ? C1 C6 1.402(15) . ? C1 Bi1 2.264(11) . ? C2 C3 1.356(17) . ? C2 H2 0.9500 . ? C3 C4 1.404(18) . ? C3 H3 0.9500 . ? C4 C5 1.349(16) . ? C4 H4 0.9500 . ? C5 C6 1.409(15) . ? C5 H5 0.9500 . ? C6 C7 1.494(15) . ? C7 C8 1.380(16) . ? C7 C12 1.382(16) . ? C8 C9 1.377(17) . ? C8 H8 0.9500 . ? C9 C10 1.390(19) . ? C9 H9 0.9500 . ? C10 C11 1.263(18) . ? C10 H10 0.9500 . ? C11 C12 1.455(16) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.377(16) . ? C13 C18 1.403(15) . ? C13 Bi1 2.248(11) . ? C14 C15 1.391(16) . ? C14 H14 0.9500 . ? C15 C16 1.413(16) . ? C15 H15 0.9500 . ? C16 C17 1.365(17) . ? C16 H16 0.9500 . ? C17 C18 1.396(16) . ? C17 H17 0.9500 . ? C18 C19 1.485(16) . ? C19 C24 1.386(16) . ? C19 C20 1.395(16) . ? C20 C21 1.393(17) . ? C20 H20 0.9500 . ? C21 C22 1.404(18) . ? C21 H21 0.9500 . ? C22 C23 1.365(18) . ? C22 H22 0.9500 . ? C23 C24 1.387(17) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? Bi1 I1 2.8829(8) . ? Bi1 HI1 0.9500 . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -1.1(16) . . . . ? Bi1 C1 C2 C3 -177.2(8) . . . . ? C1 C2 C3 C4 1.1(18) . . . . ? C2 C3 C4 C5 -1.7(18) . . . . ? C3 C4 C5 C6 2.4(17) . . . . ? C2 C1 C6 C5 1.7(15) . . . . ? Bi1 C1 C6 C5 178.1(8) . . . . ? C2 C1 C6 C7 179.3(10) . . . . ? Bi1 C1 C6 C7 -4.3(13) . . . . ? C4 C5 C6 C1 -2.4(16) . . . . ? C4 C5 C6 C7 180.0(10) . . . . ? C1 C6 C7 C8 -124.5(12) . . . . ? C5 C6 C7 C8 53.1(14) . . . . ? C1 C6 C7 C12 54.6(14) . . . . ? C5 C6 C7 C12 -127.8(11) . . . . ? C12 C7 C8 C9 -5.5(16) . . . . ? C6 C7 C8 C9 173.7(10) . . . . ? C7 C8 C9 C10 2.0(17) . . . . ? C8 C9 C10 C11 1.9(18) . . . . ? C9 C10 C11 C12 -2.2(17) . . . . ? C8 C7 C12 C11 5.1(14) . . . . ? C6 C7 C12 C11 -174.0(9) . . . . ? C10 C11 C12 C7 -1.3(15) . . . . ? C18 C13 C14 C15 -1.0(17) . . . . ? Bi1 C13 C14 C15 172.9(8) . . . . ? C13 C14 C15 C16 0.5(17) . . . . ? C14 C15 C16 C17 -0.5(18) . . . . ? C15 C16 C17 C18 1.1(19) . . . . ? C16 C17 C18 C13 -1.6(18) . . . . ? C16 C17 C18 C19 178.3(11) . . . . ? C14 C13 C18 C17 1.5(16) . . . . ? Bi1 C13 C18 C17 -172.7(9) . . . . ? C14 C13 C18 C19 -178.4(10) . . . . ? Bi1 C13 C18 C19 7.4(13) . . . . ? C17 C18 C19 C24 76.0(15) . . . . ? C13 C18 C19 C24 -104.1(12) . . . . ? C17 C18 C19 C20 -102.9(13) . . . . ? C13 C18 C19 C20 77.0(14) . . . . ? C24 C19 C20 C21 -0.7(16) . . . . ? C18 C19 C20 C21 178.2(10) . . . . ? C19 C20 C21 C22 0.8(17) . . . . ? C20 C21 C22 C23 -1.0(16) . . . . ? C21 C22 C23 C24 1.0(17) . . . . ? C20 C19 C24 C23 0.7(16) . . . . ? C18 C19 C24 C23 -178.2(10) . . . . ? C22 C23 C24 C19 -0.9(17) . . . . ?