#------------------------------------------------------------------------------ #$Date: 2020-07-06 06:52:44 +0300 (Mon, 06 Jul 2020) $ #$Revision: 253998 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/03/7240356.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_7240356 loop_ _publ_author_name 'Fritzsche, Ana-Maria' 'Scholz, Sebastian' 'Krasowska, Ma\/lgorzata' 'Bhattacharyya, Kalishankar' 'Toma, Ana Maria' 'Silvestru, Cristian' 'Korb, Marcus' 'R\"uffer, Tobias' 'Lang, Heinrich' 'Auer, Alexander A.' 'Mehring, Michael' _publ_section_title ; Evaluation of bismuth-based dispersion energy donors - synthesis, structure and theoretical study of 2-biphenylbismuth(iii) derivatives. ; _journal_issue 18 _journal_name_full 'Physical chemistry chemical physics : PCCP' _journal_page_first 10189 _journal_page_last 10211 _journal_paper_doi 10.1039/c9cp06924k _journal_volume 22 _journal_year 2020 _chemical_formula_moiety 'C24 H18 Bi Br' _chemical_formula_sum 'C24 H18 Bi Br' _chemical_formula_weight 595.27 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2020-03-16 deposited with the CCDC. 2020-04-20 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 107.717(7) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.9115(7) _cell_length_b 15.7922(9) _cell_length_c 13.3369(8) _cell_measurement_reflns_used 2726 _cell_measurement_temperature 115.7(10) _cell_measurement_theta_max 27.6480 _cell_measurement_theta_min 3.3680 _cell_volume 1988.5(2) _computing_cell_refinement 'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.41l (Rigaku OD, 2015)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXS-2013 (Sheldrick, 2013)' _diffrn_ambient_temperature 115.7(10) _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0318 _diffrn_reflns_av_unetI/netI 0.0438 _diffrn_reflns_Laue_measured_fraction_full 0.989 _diffrn_reflns_Laue_measured_fraction_max 0.989 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 8769 _diffrn_reflns_point_group_measured_fraction_full 0.989 _diffrn_reflns_point_group_measured_fraction_max 0.989 _diffrn_reflns_theta_full 25.498 _diffrn_reflns_theta_max 25.498 _diffrn_reflns_theta_min 3.432 _diffrn_source 'fine-focus sealed X-ray tube' _exptl_absorpt_coefficient_mu 10.880 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.39371 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.41l (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.988 _exptl_crystal_description block _exptl_crystal_F_000 1120 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _refine_diff_density_max 1.212 _refine_diff_density_min -1.715 _refine_diff_density_rms 0.147 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 235 _refine_ls_number_reflns 3653 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.041 _refine_ls_R_factor_all 0.0447 _refine_ls_R_factor_gt 0.0310 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0280P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0624 _refine_ls_wR_factor_ref 0.0675 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2901 _reflns_number_total 3653 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cp06924k2.cif _cod_data_source_block AP379Kr _cod_depositor_comments 'Adding full bibliography for 7240350--7240358.cif.' _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7240356 _shelx_shelxl_version_number 2018/3 _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_res_file ; TITL SIR92 run in space group P 21/n shelx.res created by SHELXL-2018/3 at 09:15:14 on 16-Mar-2020 CELL 0.71073 9.9115 15.7922 13.3369 90.000 107.717 90.000 ZERR 4.00 0.0007 0.0009 0.0008 0.000 0.007 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H BR BI UNIT 96 72 4 4 MERG 2 OMIT -2.00 51.00 OMIT 1 4 0 OMIT 0 2 1 OMIT 1 1 1 OMIT 1 2 0 mpla c1 c2 c3 c4 c5 c6 mpla c7 c8 c9 c10 c11 c12 mpla c13 c14 c15 c16 c17 c18 mpla c19 c20 c21 c22 c23 c24 FMAP 2 PLAN 25 ACTA 51.00 BOND $H CONF L.S. 10 TEMP 25.00 WGHT 0.028000 FVAR 2.61904 C1 1 0.200492 -0.131116 0.724749 11.00000 0.02227 0.01637 = 0.02500 -0.00124 -0.00107 0.00383 C2 1 0.234427 -0.160390 0.637505 11.00000 0.04588 0.02819 = 0.01940 0.00416 0.00547 0.01445 AFIX 43 H2 2 0.291006 -0.127512 0.608557 11.00000 -1.20000 AFIX 0 C3 1 0.184873 -0.238465 0.592566 11.00000 0.05822 0.03283 = 0.01988 -0.00315 -0.00343 0.02072 AFIX 43 H3 2 0.209762 -0.257681 0.534679 11.00000 -1.20000 AFIX 0 C4 1 0.100682 -0.286437 0.632814 11.00000 0.04337 0.01873 = 0.03955 -0.00023 -0.01547 0.00614 AFIX 43 H4 2 0.067018 -0.338085 0.601654 11.00000 -1.20000 AFIX 0 C5 1 0.063980 -0.259395 0.720155 11.00000 0.03663 0.01446 = 0.03784 0.00454 -0.00964 -0.00010 AFIX 43 H5 2 0.005404 -0.292596 0.746875 11.00000 -1.20000 AFIX 0 C6 1 0.115999 -0.181129 0.768404 11.00000 0.01375 0.02298 = 0.02998 0.00213 -0.01015 0.00505 C7 1 0.079971 -0.155606 0.863963 11.00000 0.02050 0.01656 = 0.03248 0.00733 0.00516 -0.00198 C8 1 0.184449 -0.134610 0.956031 11.00000 0.02176 0.02608 = 0.03293 0.00667 0.00607 0.00333 AFIX 43 H8 2 0.278790 -0.137010 0.957515 11.00000 -1.20000 AFIX 0 C9 1 0.152855 -0.110255 1.045563 11.00000 0.03858 0.03314 = 0.02897 0.00957 0.01789 0.00000 AFIX 43 H9 2 0.225130 -0.095734 1.106056 11.00000 -1.20000 AFIX 0 C10 1 0.013487 -0.107517 1.045034 11.00000 0.04683 0.03646 = 0.03942 0.01783 0.02110 0.01217 AFIX 43 H10 2 -0.008462 -0.091175 1.105236 11.00000 -1.20000 AFIX 0 C11 1 -0.092105 -0.128849 0.955943 11.00000 0.02919 0.04782 = 0.06375 0.03274 0.02724 0.01333 AFIX 43 H11 2 -0.185985 -0.127667 0.955775 11.00000 -1.20000 AFIX 0 C12 1 -0.059427 -0.152527 0.864729 11.00000 0.02404 0.02958 = 0.04531 0.01672 0.00082 -0.00501 AFIX 43 H12 2 -0.132039 -0.166312 0.804106 11.00000 -1.20000 AFIX 0 C13 1 0.299901 0.053478 0.647120 11.00000 0.02299 0.01168 = 0.02348 0.00030 0.00949 -0.00207 C14 1 0.424867 0.047471 0.619339 11.00000 0.02523 0.01992 = 0.03044 -0.00495 0.00635 -0.00166 AFIX 43 H14 2 0.496473 0.011011 0.656249 11.00000 -1.20000 AFIX 0 C15 1 0.442473 0.094737 0.538443 11.00000 0.02431 0.02702 = 0.02982 -0.00509 0.01444 -0.00342 AFIX 43 H15 2 0.525736 0.090020 0.520438 11.00000 -1.20000 AFIX 0 C16 1 0.336424 0.149997 0.482709 11.00000 0.03482 0.02277 = 0.02415 0.00037 0.01060 -0.00443 AFIX 43 H16 2 0.348193 0.182235 0.427614 11.00000 -1.20000 AFIX 0 C17 1 0.212226 0.156125 0.511007 11.00000 0.02961 0.01895 = 0.02929 0.00378 0.00919 0.00281 AFIX 43 H17 2 0.141075 0.193082 0.474659 11.00000 -1.20000 AFIX 0 C18 1 0.193687 0.107959 0.592360 11.00000 0.01742 0.01675 = 0.02069 -0.00538 0.00315 -0.00342 C19 1 0.061880 0.117206 0.623782 11.00000 0.00841 0.02279 = 0.01664 0.00192 -0.00335 0.00056 C20 1 0.027310 0.196015 0.656562 11.00000 0.02667 0.02463 = 0.02277 -0.00364 0.00509 0.00035 AFIX 43 H20 2 0.085891 0.242437 0.658802 11.00000 -1.20000 AFIX 0 C21 1 -0.095546 0.204788 0.685941 11.00000 0.02550 0.03454 = 0.02529 -0.00328 0.00566 0.00905 AFIX 43 H21 2 -0.118192 0.257010 0.708780 11.00000 -1.20000 AFIX 0 C22 1 -0.183825 0.136042 0.681212 11.00000 0.01886 0.04712 = 0.02562 0.00133 0.00713 0.00043 AFIX 43 H22 2 -0.266573 0.142563 0.699530 11.00000 -1.20000 AFIX 0 C23 1 -0.150128 0.058640 0.649787 11.00000 0.02115 0.03355 = 0.02897 -0.00057 0.00249 -0.00959 AFIX 43 H23 2 -0.209269 0.012456 0.647317 11.00000 -1.20000 AFIX 0 C24 1 -0.026920 0.049217 0.621491 11.00000 0.02638 0.02583 = 0.02359 -0.00296 0.00555 -0.00131 AFIX 43 H24 2 -0.003924 -0.003671 0.600701 11.00000 -1.20000 AFIX 0 BR1 3 0.536215 -0.050669 0.871543 11.00000 0.02365 0.03937 = 0.03659 0.00634 -0.00323 0.00344 BI1 4 0.267727 -0.002758 0.793351 11.00000 0.02165 0.01933 = 0.02054 -0.00034 0.00571 0.00050 HKLF 4 REM SIR92 run in space group P 21/n REM wR2 = 0.0675, GooF = S = 1.041, Restrained GooF = 1.041 for all data REM R1 = 0.0310 for 2901 Fo > 4sig(Fo) and 0.0447 for all 3653 data REM 235 parameters refined using 0 restraints END WGHT 0.0280 0.0000 REM Highest difference peak 1.212, deepest hole -1.715, 1-sigma level 0.147 Q1 1 0.2663 0.0600 0.8030 11.00000 0.05 1.21 Q2 1 0.2753 -0.0629 0.7790 11.00000 0.05 1.08 Q3 1 0.1838 -0.0018 0.7370 11.00000 0.05 0.92 Q4 1 0.3419 -0.0004 0.8603 11.00000 0.05 0.91 Q5 1 0.1749 0.0004 0.8161 11.00000 0.05 0.89 Q6 1 0.3508 0.0043 0.7654 11.00000 0.05 0.84 Q7 1 0.3875 0.0500 0.8437 11.00000 0.05 0.68 Q8 1 0.0821 0.0717 0.6811 11.00000 0.05 0.63 Q9 1 0.1414 0.0567 0.7610 11.00000 0.05 0.60 Q10 1 0.2467 0.0056 0.7003 11.00000 0.05 0.60 Q11 1 0.4724 -0.0680 0.6179 11.00000 0.05 0.52 Q12 1 0.2677 -0.0078 0.8949 11.00000 0.05 0.51 Q13 1 0.4129 -0.0528 0.8201 11.00000 0.05 0.48 Q14 1 0.3242 -0.1205 0.9379 11.00000 0.05 0.48 Q15 1 -0.0961 0.2103 0.6209 11.00000 0.05 0.46 Q16 1 0.4451 -0.1337 0.6771 11.00000 0.05 0.46 Q17 1 0.5463 -0.1212 0.8478 11.00000 0.05 0.45 Q18 1 0.1066 -0.0044 0.6666 11.00000 0.05 0.45 Q19 1 -0.0654 -0.1041 1.2114 11.00000 0.05 0.44 Q20 1 0.3770 -0.1050 1.0437 11.00000 0.05 0.44 Q21 1 0.3937 -0.0332 0.7412 11.00000 0.05 0.44 Q22 1 0.0780 -0.0706 0.6828 11.00000 0.05 0.44 Q23 1 0.5430 -0.0010 0.8501 11.00000 0.05 0.43 Q24 1 -0.0769 0.0004 1.0957 11.00000 0.05 0.43 Q25 1 -0.1782 0.0280 0.5160 11.00000 0.05 0.42 ; _shelx_res_checksum 16532 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2005(6) -0.1311(3) 0.7247(4) 0.0231(13) Uani 1 1 d . . . . . C2 C 0.2344(7) -0.1604(3) 0.6375(4) 0.0322(15) Uani 1 1 d . . . . . H2 H 0.291006 -0.127512 0.608557 0.039 Uiso 1 1 calc R U . . . C3 C 0.1849(8) -0.2385(4) 0.5926(4) 0.0404(18) Uani 1 1 d . . . . . H3 H 0.209762 -0.257681 0.534679 0.048 Uiso 1 1 calc R U . . . C4 C 0.1007(7) -0.2864(4) 0.6328(5) 0.0402(17) Uani 1 1 d . . . . . H4 H 0.067018 -0.338085 0.601654 0.048 Uiso 1 1 calc R U . . . C5 C 0.0640(7) -0.2594(3) 0.7202(5) 0.0343(15) Uani 1 1 d . . . . . H5 H 0.005404 -0.292596 0.746875 0.041 Uiso 1 1 calc R U . . . C6 C 0.1160(6) -0.1811(3) 0.7684(4) 0.0260(13) Uani 1 1 d . . . . . C7 C 0.0800(6) -0.1556(3) 0.8640(4) 0.0238(13) Uani 1 1 d . . . . . C8 C 0.1844(7) -0.1346(3) 0.9560(4) 0.0274(14) Uani 1 1 d . . . . . H8 H 0.278790 -0.137010 0.957515 0.033 Uiso 1 1 calc R U . . . C9 C 0.1529(7) -0.1103(3) 1.0456(4) 0.0319(15) Uani 1 1 d . . . . . H9 H 0.225130 -0.095734 1.106056 0.038 Uiso 1 1 calc R U . . . C10 C 0.0135(8) -0.1075(4) 1.0450(5) 0.0391(17) Uani 1 1 d . . . . . H10 H -0.008462 -0.091175 1.105236 0.047 Uiso 1 1 calc R U . . . C11 C -0.0921(8) -0.1288(4) 0.9559(6) 0.0440(18) Uani 1 1 d . . . . . H11 H -0.185985 -0.127667 0.955775 0.053 Uiso 1 1 calc R U . . . C12 C -0.0594(7) -0.1525(3) 0.8647(5) 0.0352(15) Uani 1 1 d . . . . . H12 H -0.132039 -0.166312 0.804106 0.042 Uiso 1 1 calc R U . . . C13 C 0.2999(6) 0.0535(3) 0.6471(4) 0.0188(12) Uani 1 1 d . . . . . C14 C 0.4249(6) 0.0475(3) 0.6193(4) 0.0257(13) Uani 1 1 d . . . . . H14 H 0.496473 0.011011 0.656249 0.031 Uiso 1 1 calc R U . . . C15 C 0.4425(6) 0.0947(3) 0.5384(4) 0.0257(13) Uani 1 1 d . . . . . H15 H 0.525736 0.090020 0.520438 0.031 Uiso 1 1 calc R U . . . C16 C 0.3364(7) 0.1500(3) 0.4827(4) 0.0269(14) Uani 1 1 d . . . . . H16 H 0.348193 0.182235 0.427614 0.032 Uiso 1 1 calc R U . . . C17 C 0.2122(6) 0.1561(3) 0.5110(4) 0.0259(13) Uani 1 1 d . . . . . H17 H 0.141075 0.193082 0.474659 0.031 Uiso 1 1 calc R U . . . C18 C 0.1937(6) 0.1080(3) 0.5924(4) 0.0189(12) Uani 1 1 d . . . . . C19 C 0.0619(5) 0.1172(3) 0.6238(4) 0.0176(11) Uani 1 1 d . . . . . C20 C 0.0273(6) 0.1960(3) 0.6566(4) 0.0252(13) Uani 1 1 d . . . . . H20 H 0.085891 0.242437 0.658802 0.030 Uiso 1 1 calc R U . . . C21 C -0.0955(6) 0.2048(4) 0.6859(4) 0.0289(14) Uani 1 1 d . . . . . H21 H -0.118192 0.257010 0.708780 0.035 Uiso 1 1 calc R U . . . C22 C -0.1838(6) 0.1360(4) 0.6812(4) 0.0305(14) Uani 1 1 d . . . . . H22 H -0.266573 0.142563 0.699530 0.037 Uiso 1 1 calc R U . . . C23 C -0.1501(6) 0.0586(4) 0.6498(4) 0.0290(14) Uani 1 1 d . . . . . H23 H -0.209269 0.012456 0.647317 0.035 Uiso 1 1 calc R U . . . C24 C -0.0269(6) 0.0492(3) 0.6215(4) 0.0257(13) Uani 1 1 d . . . . . H24 H -0.003924 -0.003671 0.600701 0.031 Uiso 1 1 calc R U . . . Br1 Br 0.53621(7) -0.05067(4) 0.87154(5) 0.03598(16) Uani 1 1 d . . . . . Bi1 Bi 0.26773(2) -0.00276(2) 0.79335(2) 0.02067(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 C1 0.022(4) 0.016(3) 0.025(3) -0.001(2) -0.001(3) 0.004(2) C2 0.046(5) 0.028(3) 0.019(3) 0.004(2) 0.005(3) 0.014(3) C3 0.058(5) 0.033(4) 0.020(3) -0.003(3) -0.003(3) 0.021(3) C4 0.043(5) 0.019(3) 0.040(4) 0.000(3) -0.015(3) 0.006(3) C5 0.037(4) 0.014(3) 0.038(4) 0.005(3) -0.010(3) 0.000(3) C6 0.014(3) 0.023(3) 0.030(3) 0.002(2) -0.010(3) 0.005(2) C7 0.020(4) 0.017(3) 0.032(3) 0.007(2) 0.005(3) -0.002(2) C8 0.022(4) 0.026(3) 0.033(3) 0.007(3) 0.006(3) 0.003(3) C9 0.039(4) 0.033(3) 0.029(3) 0.010(3) 0.018(3) 0.000(3) C10 0.047(5) 0.036(4) 0.039(4) 0.018(3) 0.021(4) 0.012(3) C11 0.029(4) 0.048(4) 0.064(5) 0.033(4) 0.027(4) 0.013(3) C12 0.024(4) 0.030(3) 0.045(4) 0.017(3) 0.001(3) -0.005(3) C13 0.023(3) 0.012(3) 0.023(3) 0.000(2) 0.009(3) -0.002(2) C14 0.025(4) 0.020(3) 0.030(3) -0.005(2) 0.006(3) -0.002(3) C15 0.024(4) 0.027(3) 0.030(3) -0.005(3) 0.014(3) -0.003(3) C16 0.035(4) 0.023(3) 0.024(3) 0.000(2) 0.011(3) -0.004(3) C17 0.030(4) 0.019(3) 0.029(3) 0.004(2) 0.009(3) 0.003(3) C18 0.017(3) 0.017(3) 0.021(3) -0.005(2) 0.003(2) -0.003(2) C19 0.008(3) 0.023(3) 0.017(3) 0.002(2) -0.003(2) 0.001(2) C20 0.027(4) 0.025(3) 0.023(3) -0.004(2) 0.005(3) 0.000(3) C21 0.026(4) 0.035(3) 0.025(3) -0.003(3) 0.006(3) 0.009(3) C22 0.019(4) 0.047(4) 0.026(3) 0.001(3) 0.007(3) 0.000(3) C23 0.021(4) 0.034(3) 0.029(3) -0.001(3) 0.002(3) -0.010(3) C24 0.026(4) 0.026(3) 0.024(3) -0.003(2) 0.006(3) -0.001(3) Br1 0.0237(4) 0.0394(4) 0.0366(3) 0.0063(3) -0.0032(3) 0.0034(3) Bi1 0.02165(14) 0.01933(13) 0.02054(13) -0.00034(8) 0.00571(10) 0.00050(10) 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 119.3(5) . . ? C2 C1 Bi1 121.8(4) . . ? C6 C1 Bi1 118.8(3) . . ? C1 C2 C3 120.8(6) . . ? C1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? C4 C3 C2 120.3(5) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 120.7(5) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C4 C5 C6 119.8(6) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C1 C6 C5 119.0(5) . . ? C1 C6 C7 122.4(5) . . ? C5 C6 C7 118.6(5) . . ? C8 C7 C12 117.6(5) . . ? C8 C7 C6 121.2(5) . . ? C12 C7 C6 121.2(5) . . ? C9 C8 C7 122.0(6) . . ? C9 C8 H8 119.0 . . ? C7 C8 H8 119.0 . . ? C8 C9 C10 119.7(6) . . ? C8 C9 H9 120.2 . . ? C10 C9 H9 120.2 . . ? C11 C10 C9 119.9(6) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C10 C11 C12 120.2(6) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C7 C12 C11 120.7(6) . . ? C7 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C18 C13 C14 119.7(5) . . ? C18 C13 Bi1 114.6(3) . . ? C14 C13 Bi1 124.9(4) . . ? C15 C14 C13 120.5(5) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C14 C15 C16 120.4(5) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C15 C16 C17 118.9(5) . . ? C15 C16 H16 120.6 . . ? C17 C16 H16 120.6 . . ? C18 C17 C16 120.8(5) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C17 C18 C13 119.7(5) . . ? C17 C18 C19 120.2(5) . . ? C13 C18 C19 120.1(4) . . ? C24 C19 C20 118.9(5) . . ? C24 C19 C18 121.5(5) . . ? C20 C19 C18 119.6(5) . . ? C21 C20 C19 119.7(5) . . ? C21 C20 H20 120.2 . . ? C19 C20 H20 120.2 . . ? C22 C21 C20 120.2(5) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? C23 C22 C21 120.4(5) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C22 C23 C24 119.7(5) . . ? C22 C23 H23 120.1 . . ? C24 C23 H23 120.1 . . ? C19 C24 C23 121.1(5) . . ? C19 C24 H24 119.5 . . ? C23 C24 H24 119.5 . . ? C1 Bi1 C13 96.09(17) . . ? C1 Bi1 Br1 92.33(14) . . ? C13 Bi1 Br1 93.63(14) . . ? 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 1.385(7) . ? C1 C6 1.400(7) . ? C1 Bi1 2.240(5) . ? C2 C3 1.393(8) . ? C2 H2 0.9300 . ? C3 C4 1.353(8) . ? C3 H3 0.9300 . ? C4 C5 1.389(8) . ? C4 H4 0.9300 . ? C5 C6 1.416(7) . ? C5 H5 0.9300 . ? C6 C7 1.480(7) . ? C7 C8 1.384(8) . ? C7 C12 1.386(8) . ? C8 C9 1.378(7) . ? C8 H8 0.9300 . ? C9 C10 1.380(8) . ? C9 H9 0.9300 . ? C10 C11 1.365(10) . ? C10 H10 0.9300 . ? C11 C12 1.402(8) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C18 1.383(7) . ? C13 C14 1.400(7) . ? C13 Bi1 2.252(5) . ? C14 C15 1.366(7) . ? C14 H14 0.9300 . ? C15 C16 1.394(8) . ? C15 H15 0.9300 . ? C16 C17 1.396(7) . ? C16 H16 0.9300 . ? C17 C18 1.382(6) . ? C17 H17 0.9300 . ? C18 C19 1.496(7) . ? C19 C24 1.383(7) . ? C19 C20 1.396(7) . ? C20 C21 1.395(7) . ? C20 H20 0.9300 . ? C21 C22 1.384(8) . ? C21 H21 0.9300 . ? C22 C23 1.366(7) . ? C22 H22 0.9300 . ? C23 C24 1.392(7) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? Br1 Bi1 2.6557(7) . ? 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 0.4(9) . . . . ? Bi1 C1 C2 C3 -176.4(5) . . . . ? C1 C2 C3 C4 1.0(9) . . . . ? C2 C3 C4 C5 -0.9(10) . . . . ? C3 C4 C5 C6 -0.5(9) . . . . ? C2 C1 C6 C5 -1.8(8) . . . . ? Bi1 C1 C6 C5 175.1(4) . . . . ? C2 C1 C6 C7 177.6(5) . . . . ? Bi1 C1 C6 C7 -5.5(7) . . . . ? C4 C5 C6 C1 1.9(8) . . . . ? C4 C5 C6 C7 -177.5(5) . . . . ? C1 C6 C7 C8 -54.0(7) . . . . ? C5 C6 C7 C8 125.4(6) . . . . ? C1 C6 C7 C12 126.5(6) . . . . ? C5 C6 C7 C12 -54.1(7) . . . . ? C12 C7 C8 C9 -0.9(8) . . . . ? C6 C7 C8 C9 179.6(5) . . . . ? C7 C8 C9 C10 0.9(8) . . . . ? C8 C9 C10 C11 -0.1(9) . . . . ? C9 C10 C11 C12 -0.8(9) . . . . ? C8 C7 C12 C11 0.0(8) . . . . ? C6 C7 C12 C11 179.5(5) . . . . ? C10 C11 C12 C7 0.8(9) . . . . ? C18 C13 C14 C15 -0.2(8) . . . . ? Bi1 C13 C14 C15 -169.4(4) . . . . ? C13 C14 C15 C16 0.3(8) . . . . ? C14 C15 C16 C17 0.0(8) . . . . ? C15 C16 C17 C18 -0.4(8) . . . . ? C16 C17 C18 C13 0.6(8) . . . . ? C16 C17 C18 C19 178.2(5) . . . . ? C14 C13 C18 C17 -0.2(8) . . . . ? Bi1 C13 C18 C17 170.1(4) . . . . ? C14 C13 C18 C19 -177.8(4) . . . . ? Bi1 C13 C18 C19 -7.5(6) . . . . ? C17 C18 C19 C24 121.3(6) . . . . ? C13 C18 C19 C24 -61.1(7) . . . . ? C17 C18 C19 C20 -58.9(7) . . . . ? C13 C18 C19 C20 118.7(5) . . . . ? C24 C19 C20 C21 -0.2(8) . . . . ? C18 C19 C20 C21 -180.0(5) . . . . ? C19 C20 C21 C22 -0.9(8) . . . . ? C20 C21 C22 C23 1.3(8) . . . . ? C21 C22 C23 C24 -0.6(8) . . . . ? C20 C19 C24 C23 0.9(8) . . . . ? C18 C19 C24 C23 -179.3(5) . . . . ? C22 C23 C24 C19 -0.5(8) . . . . ?