Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Peter Junk' 'Marcus Brym' 'Craig Forsyth' 'Cameron Jones' 'Richard P Rose' 'Andreas Stasch' 'David R Turner' _publ_contact_author_name 'Peter Junk' _publ_contact_author_address ; School of Chemistry Monash University Clayton 3800 AUSTRALIA ; _publ_contact_author_email PETER.JUNK@SCI.MONASH.EDU.AU _publ_requested_journal 'Dalton Transactions' _publ_section_title ; Ligand effects in the syntheses and structures of novel heteroleptic and homoleptic bismuth(III) formamidinate complexes ; data_1a _database_code_depnum_ccdc_archive 'CCDC 643175' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C58 H86 Bi2 Br4 N4 O2, 2(C4 H10 O)' _chemical_formula_sum 'C66 H106 Bi2 Br4 N4 O4' _chemical_formula_weight 1757.15 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' N N 0.0061 0.0033 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.0078(6) _cell_length_b 12.9849(12) _cell_length_c 13.8084(12) _cell_angle_alpha 64.962(3) _cell_angle_beta 69.100(5) _cell_angle_gamma 73.200(5) _cell_volume 1797.9(2) _cell_formula_units_Z 1 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.623 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 868 _exptl_absorpt_coefficient_mu 7.155 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.3940 _exptl_absorpt_correction_T_max 0.5984 _exptl_absorpt_process_details 'performed as part of the DENZO-SMN package' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius Kappa CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14578 _diffrn_reflns_av_R_equivalents 0.0668 _diffrn_reflns_av_sigmaI/netI 0.0854 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 27.50 _reflns_number_total 8110 _reflns_number_gt 6579 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed / POV-Ray' _computing_publication_material 'Microsoft Office 2000' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1027P)^2^+1.0238P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8110 _refine_ls_number_parameters 371 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0868 _refine_ls_R_factor_gt 0.0666 _refine_ls_wR_factor_ref 0.1636 _refine_ls_wR_factor_gt 0.1530 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 _atom_site_disorder_assembly _atom_site_disorder_group Bi1 Bi 0.02265(2) 0.42339(3) 0.16517(2) 0.01905(12) Uani 1 1 d . . . Br1 Br -0.06872(7) 0.46794(8) 0.35282(7) 0.0301(2) Uani 1 1 d . . . Br2 Br -0.08382(7) 0.64880(7) 0.03872(7) 0.02503(19) Uani 1 1 d . . . O1 O -0.0376(6) 0.2152(6) 0.2666(6) 0.0390(16) Uani 1 1 d . . . O2 O -0.4638(6) 0.7692(6) 0.3309(6) 0.0488(19) Uani 1 1 d . . . N1 N 0.1942(6) 0.5041(6) 0.1035(5) 0.0204(14) Uani 1 1 d . . . N2 N 0.2069(6) 0.3188(6) 0.2132(5) 0.0209(14) Uani 1 1 d . . . C1 C 0.2459(7) 0.6049(7) 0.0232(7) 0.0211(17) Uani 1 1 d . . . C2 C 0.2164(8) 0.7050(8) 0.0495(7) 0.0283(19) Uani 1 1 d . . . C3 C 0.2743(8) 0.7986(8) -0.0249(7) 0.0287(19) Uani 1 1 d . . . H3 H 0.2553 0.8670 -0.0090 0.034 Uiso 1 1 calc R . . C4 C 0.3598(8) 0.7924(8) -0.1222(8) 0.031(2) Uani 1 1 d . . . H4 H 0.4019 0.8552 -0.1706 0.038 Uiso 1 1 calc R . . C5 C 0.3841(7) 0.6957(8) -0.1493(7) 0.0254(18) Uani 1 1 d . . . H5 H 0.4405 0.6950 -0.2179 0.031 Uiso 1 1 calc R . . C6 C 0.3289(7) 0.5992(7) -0.0795(6) 0.0213(17) Uani 1 1 d . . . C7 C 0.3527(7) 0.4992(7) -0.1149(6) 0.0210(17) Uani 1 1 d . . . H7 H 0.2964 0.4444 -0.0590 0.025 Uiso 1 1 calc R . . C8 C 0.3273(8) 0.5400(9) -0.2285(7) 0.032(2) Uani 1 1 d . . . H8A H 0.2486 0.5904 -0.2273 0.047 Uiso 1 1 calc R . . H8B H 0.3264 0.4730 -0.2436 0.047 Uiso 1 1 calc R . . H8C H 0.3906 0.5825 -0.2867 0.047 Uiso 1 1 calc R . . C9 C 0.4818(7) 0.4354(8) -0.1205(7) 0.0290(19) Uani 1 1 d . . . H9A H 0.5383 0.4869 -0.1771 0.044 Uiso 1 1 calc R . . H9B H 0.4928 0.3680 -0.1399 0.044 Uiso 1 1 calc R . . H9C H 0.4972 0.4103 -0.0481 0.044 Uiso 1 1 calc R . . C10 C 0.1264(7) 0.7106(7) 0.1574(7) 0.0273(19) Uani 1 1 d . . . H10 H 0.0742 0.6510 0.1846 0.033 Uiso 1 1 calc R . . C11 C 0.1919(9) 0.6800(10) 0.2455(9) 0.045(3) Uani 1 1 d . . . H11A H 0.2367 0.6013 0.2596 0.067 Uiso 1 1 calc R . . H11B H 0.1325 0.6852 0.3144 0.067 Uiso 1 1 calc R . . H11C H 0.2482 0.7339 0.2190 0.067 Uiso 1 1 calc R . . C12 C 0.0438(8) 0.8272(9) 0.1437(9) 0.042(3) Uani 1 1 d . . . H12A H 0.0924 0.8875 0.1182 0.062 Uiso 1 1 calc R . . H12B H -0.0148 0.8250 0.2151 0.062 Uiso 1 1 calc R . . H12C H 0.0007 0.8441 0.0889 0.062 Uiso 1 1 calc R . . C13 C 0.2594(6) 0.4101(7) 0.1538(6) 0.0159(15) Uani 1 1 d . . . H13 H 0.3414 0.4079 0.1476 0.019 Uiso 1 1 calc R . . C14 C 0.2668(6) 0.2171(7) 0.2814(7) 0.0207(17) Uani 1 1 d . . . C15 C 0.2839(7) 0.2139(7) 0.3797(7) 0.0239(18) Uani 1 1 d . . . C16 C 0.3478(8) 0.1144(8) 0.4390(7) 0.031(2) Uani 1 1 d . . . H16 H 0.3608 0.1112 0.5042 0.037 Uiso 1 1 calc R . . C17 C 0.3930(8) 0.0203(9) 0.4079(8) 0.035(2) Uani 1 1 d . . . H17 H 0.4399 -0.0451 0.4488 0.041 Uiso 1 1 calc R . . C18 C 0.3700(8) 0.0209(8) 0.3162(8) 0.033(2) Uani 1 1 d . . . H18 H 0.3964 -0.0463 0.2974 0.040 Uiso 1 1 calc R . . C19 C 0.3081(7) 0.1198(7) 0.2511(7) 0.0228(17) Uani 1 1 d . . . C20 C 0.2882(8) 0.1195(8) 0.1488(8) 0.031(2) Uani 1 1 d . . . H20 H 0.2188 0.1816 0.1302 0.037 Uiso 1 1 calc R . . C21 C 0.2584(11) 0.0067(11) 0.1641(10) 0.055(3) Uani 1 1 d . . . H21A H 0.3315 -0.0517 0.1650 0.082 Uiso 1 1 calc R . . H21B H 0.2279 0.0180 0.1026 0.082 Uiso 1 1 calc R . . H21C H 0.1967 -0.0191 0.2345 0.082 Uiso 1 1 calc R . . C22 C 0.3985(11) 0.1478(12) 0.0519(8) 0.056(3) Uani 1 1 d . . . H22A H 0.4163 0.2218 0.0403 0.084 Uiso 1 1 calc R . . H22B H 0.3831 0.1526 -0.0151 0.084 Uiso 1 1 calc R . . H22C H 0.4676 0.0873 0.0675 0.084 Uiso 1 1 calc R . . C23 C 0.2288(8) 0.3136(8) 0.4220(7) 0.029(2) Uani 1 1 d . . . H23 H 0.1871 0.3769 0.3675 0.035 Uiso 1 1 calc R . . C24 C 0.1341(9) 0.2751(9) 0.5346(8) 0.038(2) Uani 1 1 d . . . H24A H 0.0743 0.2427 0.5275 0.058 Uiso 1 1 calc R . . H24B H 0.0935 0.3416 0.5574 0.058 Uiso 1 1 calc R . . H24C H 0.1741 0.2165 0.5904 0.058 Uiso 1 1 calc R . . C25 C 0.3256(9) 0.3615(9) 0.4327(8) 0.040(2) Uani 1 1 d . . . H25A H 0.3710 0.2994 0.4823 0.060 Uiso 1 1 calc R . . H25B H 0.2864 0.4228 0.4632 0.060 Uiso 1 1 calc R . . H25C H 0.3811 0.3926 0.3593 0.060 Uiso 1 1 calc R . . C26 C -0.0952(12) 0.1683(10) 0.2217(10) 0.058(3) Uani 1 1 d . . . H26A H -0.1500 0.2306 0.1806 0.070 Uiso 1 1 calc R . . H26B H -0.0334 0.1329 0.1698 0.070 Uiso 1 1 calc R . . C27 C -0.1605(18) 0.0856(17) 0.3095(16) 0.129(9) Uani 1 1 d . . . H27A H -0.1577 0.0212 0.2877 0.154 Uiso 1 1 calc R . . H27B H -0.2460 0.1197 0.3341 0.154 Uiso 1 1 calc R . . C28 C -0.0946(15) 0.0428(14) 0.4048(13) 0.091(5) Uani 1 1 d . . . H28A H -0.1529 0.0223 0.4792 0.109 Uiso 1 1 calc R . . H28B H -0.0308 -0.0246 0.4009 0.109 Uiso 1 1 calc R . . C29 C -0.0411(11) 0.1465(10) 0.3796(9) 0.050(3) Uani 1 1 d . . . H29A H -0.0922 0.1898 0.4287 0.060 Uiso 1 1 calc R . . H29B H 0.0412 0.1224 0.3900 0.060 Uiso 1 1 calc R . . C30 C -0.5159(10) 0.6686(10) 0.3869(9) 0.047(3) Uani 1 1 d . . . H30A H -0.4654 0.6081 0.4339 0.057 Uiso 1 1 calc R . . H30B H -0.5199 0.6400 0.3324 0.057 Uiso 1 1 calc R . . C31 C -0.6389(12) 0.6933(14) 0.4569(12) 0.081(5) Uani 1 1 d . . . H31A H -0.6341 0.7176 0.5132 0.121 Uiso 1 1 calc R . . H31B H -0.6763 0.6236 0.4934 0.121 Uiso 1 1 calc R . . H31C H -0.6878 0.7549 0.4103 0.121 Uiso 1 1 calc R . . C32 C -0.3498(10) 0.7577(10) 0.2609(9) 0.046(3) Uani 1 1 d . . . H32A H -0.3511 0.7269 0.2070 0.056 Uiso 1 1 calc R . . H32B H -0.2936 0.7021 0.3046 0.056 Uiso 1 1 calc R . . C33 C -0.3053(9) 0.8705(10) 0.1997(10) 0.049(3) Uani 1 1 d . . . H33A H -0.3619 0.9262 0.1579 0.073 Uiso 1 1 calc R . . H33B H -0.2256 0.8604 0.1482 0.073 Uiso 1 1 calc R . . H33C H -0.2993 0.8989 0.2528 0.073 Uiso 1 1 calc R . . 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 0.01690(17) 0.02069(18) 0.01860(18) -0.00655(12) -0.00256(11) -0.00526(11) Br1 0.0259(4) 0.0393(5) 0.0221(4) -0.0138(4) 0.0015(3) -0.0068(4) Br2 0.0264(4) 0.0225(4) 0.0265(5) -0.0091(4) -0.0085(3) -0.0021(3) O1 0.053(4) 0.030(4) 0.037(4) -0.005(3) -0.015(3) -0.018(3) O2 0.045(4) 0.031(4) 0.053(5) -0.004(4) -0.009(4) -0.004(3) N1 0.024(3) 0.019(4) 0.019(4) -0.008(3) -0.001(3) -0.009(3) N2 0.018(3) 0.022(4) 0.019(4) -0.008(3) 0.000(3) -0.004(3) C1 0.021(4) 0.025(4) 0.020(4) -0.007(3) -0.008(3) -0.005(3) C2 0.033(5) 0.022(5) 0.028(5) -0.005(4) -0.008(4) -0.009(4) C3 0.030(5) 0.020(4) 0.031(5) -0.009(4) 0.001(4) -0.008(3) C4 0.030(5) 0.026(5) 0.032(5) -0.002(4) -0.006(4) -0.012(4) C5 0.023(4) 0.030(5) 0.019(4) -0.004(4) -0.003(3) -0.010(3) C6 0.016(4) 0.027(5) 0.018(4) -0.003(3) -0.005(3) -0.008(3) C7 0.021(4) 0.030(5) 0.011(4) -0.006(3) 0.002(3) -0.013(3) C8 0.031(5) 0.046(6) 0.024(5) -0.015(4) -0.009(4) -0.008(4) C9 0.029(5) 0.033(5) 0.026(5) -0.012(4) -0.002(4) -0.010(4) C10 0.027(4) 0.023(5) 0.033(5) -0.015(4) -0.004(4) -0.003(3) C11 0.037(6) 0.052(7) 0.040(6) -0.024(5) -0.009(5) 0.009(5) C12 0.027(5) 0.041(6) 0.056(7) -0.027(5) 0.001(4) -0.005(4) C13 0.013(3) 0.023(4) 0.015(4) -0.007(3) -0.006(3) -0.005(3) C14 0.012(4) 0.023(4) 0.022(4) -0.004(3) -0.003(3) -0.003(3) C15 0.021(4) 0.026(5) 0.019(4) -0.005(4) -0.004(3) -0.001(3) C16 0.030(5) 0.041(6) 0.019(4) -0.006(4) -0.009(4) -0.005(4) C17 0.025(5) 0.034(5) 0.030(5) -0.003(4) -0.007(4) 0.004(4) C18 0.030(5) 0.024(5) 0.039(6) -0.008(4) -0.003(4) -0.009(4) C19 0.022(4) 0.019(4) 0.027(5) -0.008(4) -0.007(3) -0.002(3) C20 0.032(5) 0.030(5) 0.033(5) -0.012(4) -0.012(4) -0.003(4) C21 0.060(7) 0.060(8) 0.058(8) -0.036(7) 0.003(6) -0.029(6) C22 0.068(8) 0.080(9) 0.021(5) -0.008(6) -0.003(5) -0.041(7) C23 0.033(5) 0.038(5) 0.017(4) -0.011(4) -0.004(4) -0.008(4) C24 0.040(5) 0.043(6) 0.026(5) -0.017(5) 0.008(4) -0.013(4) C25 0.052(6) 0.046(6) 0.024(5) -0.016(5) 0.000(4) -0.019(5) C26 0.077(9) 0.045(7) 0.053(8) 0.012(6) -0.035(6) -0.033(6) C27 0.137(16) 0.115(16) 0.140(17) 0.040(13) -0.098(14) -0.086(13) C28 0.095(12) 0.079(12) 0.076(11) 0.017(9) -0.033(9) -0.039(9) C29 0.054(7) 0.055(7) 0.033(6) -0.003(5) -0.008(5) -0.024(6) C30 0.065(7) 0.041(6) 0.029(6) -0.006(5) -0.014(5) -0.008(5) C31 0.068(9) 0.093(12) 0.060(9) -0.005(8) -0.003(7) -0.034(8) C32 0.043(6) 0.048(7) 0.037(6) -0.011(5) -0.009(5) -0.002(5) C33 0.037(6) 0.050(7) 0.057(7) -0.024(6) -0.010(5) 0.000(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Bi1 N1 2.305(6) . ? Bi1 N2 2.393(7) . ? Bi1 O1 2.645(6) . ? Bi1 Br1 2.6694(9) . ? Bi1 C13 2.749(7) . ? Bi1 Br2 2.8903(9) . ? Bi1 Br2 3.1151(9) 2_565 ? Br2 Bi1 3.1151(9) 2_565 ? O1 C29 1.425(12) . ? O1 C26 1.449(13) . ? O2 C32 1.376(12) . ? O2 C30 1.403(13) . ? N1 C13 1.306(10) . ? N1 C1 1.441(10) . ? N2 C13 1.310(9) . ? N2 C14 1.425(10) . ? C1 C2 1.411(12) . ? C1 C6 1.431(11) . ? C2 C3 1.392(12) . ? C2 C10 1.514(12) . ? C3 C4 1.387(12) . ? C3 H3 0.9500 . ? C4 C5 1.382(13) . ? C4 H4 0.9500 . ? C5 C6 1.393(11) . ? C5 H5 0.9500 . ? C6 C7 1.494(12) . ? C7 C9 1.524(11) . ? C7 C8 1.541(11) . ? C7 H7 1.0000 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C12 1.529(12) . ? C10 C11 1.532(13) . ? C10 H10 1.0000 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13 0.9500 . ? C14 C19 1.397(11) . ? C14 C15 1.426(11) . ? C15 C16 1.381(12) . ? C15 C23 1.525(12) . ? C16 C17 1.366(14) . ? C16 H16 0.9500 . ? C17 C18 1.385(14) . ? C17 H17 0.9500 . ? C18 C19 1.399(12) . ? C18 H18 0.9500 . ? C19 C20 1.516(12) . ? C20 C22 1.510(13) . ? C20 C21 1.519(13) . ? C20 H20 1.0000 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C24 1.540(12) . ? C23 C25 1.542(13) . ? C23 H23 1.0000 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 C27 1.394(18) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.59(2) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 C29 1.513(18) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 C31 1.479(16) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 C33 1.492(15) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? 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 N1 Bi1 N2 56.7(2) . . ? N1 Bi1 O1 137.6(2) . . ? N2 Bi1 O1 81.6(2) . . ? N1 Bi1 Br1 96.23(17) . . ? N2 Bi1 Br1 92.12(16) . . ? O1 Bi1 Br1 91.98(16) . . ? N1 Bi1 C13 28.2(2) . . ? N2 Bi1 C13 28.5(2) . . ? O1 Bi1 C13 109.7(2) . . ? Br1 Bi1 C13 94.95(15) . . ? N1 Bi1 Br2 85.24(17) . . ? N2 Bi1 Br2 141.92(16) . . ? O1 Bi1 Br2 136.03(15) . . ? Br1 Bi1 Br2 92.13(3) . . ? C13 Bi1 Br2 113.47(16) . . ? N1 Bi1 Br2 94.90(16) . 2_565 ? N2 Bi1 Br2 94.22(16) . 2_565 ? O1 Bi1 Br2 79.92(15) . 2_565 ? Br1 Bi1 Br2 168.86(3) . 2_565 ? C13 Bi1 Br2 94.98(15) . 2_565 ? Br2 Bi1 Br2 88.52(2) . 2_565 ? Bi1 Br2 Bi1 91.48(2) . 2_565 ? C29 O1 C26 111.4(8) . . ? C29 O1 Bi1 124.1(6) . . ? C26 O1 Bi1 123.4(6) . . ? C32 O2 C30 115.1(9) . . ? C13 N1 C1 122.3(7) . . ? C13 N1 Bi1 95.2(5) . . ? C1 N1 Bi1 141.3(5) . . ? C13 N2 C14 120.4(6) . . ? C13 N2 Bi1 91.1(5) . . ? C14 N2 Bi1 147.8(5) . . ? C2 C1 C6 121.8(8) . . ? C2 C1 N1 119.1(7) . . ? C6 C1 N1 119.0(7) . . ? C3 C2 C1 118.6(8) . . ? C3 C2 C10 120.2(8) . . ? C1 C2 C10 121.2(8) . . ? C4 C3 C2 120.4(9) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C5 C4 C3 120.5(8) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 122.4(8) . . ? C4 C5 H5 118.8 . . ? C6 C5 H5 118.8 . . ? C5 C6 C1 116.3(8) . . ? C5 C6 C7 120.5(7) . . ? C1 C6 C7 123.2(7) . . ? C6 C7 C9 111.7(6) . . ? C6 C7 C8 110.2(7) . . ? C9 C7 C8 110.1(7) . . ? C6 C7 H7 108.3 . . ? C9 C7 H7 108.3 . . ? C8 C7 H7 108.3 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C2 C10 C12 112.9(8) . . ? C2 C10 C11 110.5(7) . . ? C12 C10 C11 110.7(8) . . ? C2 C10 H10 107.5 . . ? C12 C10 H10 107.5 . . ? C11 C10 H10 107.5 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N1 C13 N2 117.1(7) . . ? N1 C13 Bi1 56.6(4) . . ? N2 C13 Bi1 60.5(4) . . ? N1 C13 H13 121.5 . . ? N2 C13 H13 121.5 . . ? Bi1 C13 H13 178.0 . . ? C19 C14 N2 119.1(7) . . ? C19 C14 C15 120.2(7) . . ? N2 C14 C15 120.7(7) . . ? C16 C15 C14 117.6(8) . . ? C16 C15 C23 120.6(8) . . ? C14 C15 C23 121.7(7) . . ? C17 C16 C15 122.8(9) . . ? C17 C16 H16 118.6 . . ? C15 C16 H16 118.6 . . ? C16 C17 C18 119.6(9) . . ? C16 C17 H17 120.2 . . ? C18 C17 H17 120.2 . . ? C17 C18 C19 120.4(9) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? C14 C19 C18 119.3(8) . . ? C14 C19 C20 121.4(7) . . ? C18 C19 C20 119.3(8) . . ? C22 C20 C19 109.8(8) . . ? C22 C20 C21 109.3(9) . . ? C19 C20 C21 113.9(8) . . ? C22 C20 H20 107.9 . . ? C19 C20 H20 107.9 . . ? C21 C20 H20 107.9 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C15 C23 C24 110.1(8) . . ? C15 C23 C25 112.0(8) . . ? C24 C23 C25 110.0(8) . . ? C15 C23 H23 108.2 . . ? C24 C23 H23 108.2 . . ? C25 C23 H23 108.2 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C27 C26 O1 108.5(11) . . ? C27 C26 H26A 110.0 . . ? O1 C26 H26A 110.0 . . ? C27 C26 H26B 110.0 . . ? O1 C26 H26B 110.0 . . ? H26A C26 H26B 108.4 . . ? C26 C27 C28 104.1(11) . . ? C26 C27 H27A 110.9 . . ? C28 C27 H27A 110.9 . . ? C26 C27 H27B 110.9 . . ? C28 C27 H27B 110.9 . . ? H27A C27 H27B 109.0 . . ? C29 C28 C27 103.0(11) . . ? C29 C28 H28A 111.2 . . ? C27 C28 H28A 111.2 . . ? C29 C28 H28B 111.2 . . ? C27 C28 H28B 111.2 . . ? H28A C28 H28B 109.1 . . ? O1 C29 C28 105.3(10) . . ? O1 C29 H29A 110.7 . . ? C28 C29 H29A 110.7 . . ? O1 C29 H29B 110.7 . . ? C28 C29 H29B 110.7 . . ? H29A C29 H29B 108.8 . . ? O2 C30 C31 109.7(10) . . ? O2 C30 H30A 109.7 . . ? C31 C30 H30A 109.7 . . ? O2 C30 H30B 109.7 . . ? C31 C30 H30B 109.7 . . ? H30A C30 H30B 108.2 . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? O2 C32 C33 111.2(9) . . ? O2 C32 H32A 109.4 . . ? C33 C32 H32A 109.4 . . ? O2 C32 H32B 109.4 . . ? C33 C32 H32B 109.4 . . ? H32A C32 H32B 108.0 . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 4.060 _refine_diff_density_min -3.696 _refine_diff_density_rms 0.267 # Attachment '1d.CIF' data_rpr012a _database_code_depnum_ccdc_archive 'CCDC 643176' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C42 H54 Bi2 Br4 N4 O2' _chemical_formula_sum 'C42 H54 Bi2 Br4 N4 O2' _chemical_formula_weight 1384.49 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' N N 0.0061 0.0033 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_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' _cell_length_a 14.599(3) _cell_length_b 10.930(2) _cell_length_c 14.697(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.60(3) _cell_angle_gamma 90.00 _cell_volume 2340.6(8) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.964 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 10.959 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2430 _exptl_absorpt_correction_T_max 0.3530 _exptl_absorpt_process_details 'performed as part of the DENZO-SMN package' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius Kappa CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11721 _diffrn_reflns_av_R_equivalents 0.0671 _diffrn_reflns_av_sigmaI/netI 0.0828 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5299 _reflns_number_gt 3890 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed / POV-Ray' _computing_publication_material 'Microsoft Office 2000' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0784P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5299 _refine_ls_number_parameters 249 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0818 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_ref 0.1335 _refine_ls_wR_factor_gt 0.1212 _refine_ls_goodness_of_fit_ref 0.982 _refine_ls_restrained_S_all 0.982 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 _atom_site_disorder_assembly _atom_site_disorder_group Bi1 Bi 0.068423(19) 0.09252(3) 0.11767(2) 0.01774(13) Uani 1 1 d . . . Br1 Br 0.24370(6) 0.13644(9) 0.17471(6) 0.0307(2) Uani 1 1 d . . . Br2 Br -0.12130(6) -0.01388(8) 0.06213(6) 0.0265(2) Uani 1 1 d . . . O7 O 0.0390(4) 0.0139(6) 0.2827(4) 0.0379(17) Uani 1 1 d . . . N1 N 0.0431(4) 0.2741(6) 0.0424(4) 0.0183(15) Uani 1 1 d . . . N2 N 0.0048(4) 0.2647(6) 0.1863(5) 0.0188(15) Uani 1 1 d . . . C1 C 0.0476(5) 0.3242(7) -0.0475(5) 0.0163(16) Uani 1 1 d . . . C2 C -0.0331(6) 0.3286(8) -0.1070(6) 0.0243(19) Uani 1 1 d . . . C3 C -0.0226(6) 0.3659(8) -0.1960(6) 0.0253(19) Uani 1 1 d . . . H3 H -0.0754 0.3696 -0.2371 0.030 Uiso 1 1 calc R . . C4 C 0.0608(6) 0.3978(7) -0.2271(6) 0.025(2) Uani 1 1 d . . . H4 H 0.0654 0.4206 -0.2890 0.030 Uiso 1 1 calc R . . C5 C 0.1376(6) 0.3963(7) -0.1681(6) 0.0208(18) Uani 1 1 d . . . H5 H 0.1951 0.4200 -0.1894 0.025 Uiso 1 1 calc R . . C6 C 0.1328(6) 0.3608(7) -0.0776(6) 0.0213(18) Uani 1 1 d . . . C7 C 0.2173(6) 0.3624(8) -0.0117(6) 0.026(2) Uani 1 1 d . . . H7A H 0.2034 0.4070 0.0437 0.039 Uiso 1 1 calc R . . H7B H 0.2679 0.4030 -0.0404 0.039 Uiso 1 1 calc R . . H7C H 0.2351 0.2783 0.0043 0.039 Uiso 1 1 calc R . . C8 C -0.1246(6) 0.2936(10) -0.0745(7) 0.035(2) Uani 1 1 d . . . H8A H -0.1422 0.3522 -0.0282 0.053 Uiso 1 1 calc R . . H8B H -0.1209 0.2114 -0.0481 0.053 Uiso 1 1 calc R . . H8C H -0.1705 0.2945 -0.1261 0.053 Uiso 1 1 calc R . . C9 C 0.0047(5) 0.3293(7) 0.1098(5) 0.0176(17) Uani 1 1 d . . . H9 H -0.0211 0.4089 0.1042 0.021 Uiso 1 1 calc R . . C10 C -0.0372(5) 0.3037(7) 0.2659(5) 0.0157(16) Uani 1 1 d . . . C11 C -0.1331(6) 0.3118(7) 0.2660(6) 0.0229(19) Uani 1 1 d . . . C12 C -0.1707(7) 0.3526(8) 0.3453(6) 0.027(2) Uani 1 1 d . . . H12 H -0.2353 0.3620 0.3459 0.033 Uiso 1 1 calc R . . C13 C -0.1175(7) 0.3794(8) 0.4219(7) 0.031(2) Uani 1 1 d . . . H13 H -0.1455 0.4064 0.4750 0.038 Uiso 1 1 calc R . . C14 C -0.0223(7) 0.3677(8) 0.4233(6) 0.026(2) Uani 1 1 d . . . H14 H 0.0141 0.3858 0.4775 0.031 Uiso 1 1 calc R . . C15 C 0.0201(6) 0.3290(8) 0.3445(6) 0.0232(19) Uani 1 1 d . . . C16 C 0.1209(6) 0.3183(9) 0.3461(7) 0.034(2) Uani 1 1 d . . . H16A H 0.1378 0.2325 0.3373 0.051 Uiso 1 1 calc R . . H16B H 0.1478 0.3472 0.4050 0.051 Uiso 1 1 calc R . . H16C H 0.1440 0.3681 0.2970 0.051 Uiso 1 1 calc R . . C17 C -0.1938(6) 0.2813(8) 0.1826(6) 0.026(2) Uani 1 1 d . . . H17A H -0.2547 0.2572 0.2010 0.039 Uiso 1 1 calc R . . H17B H -0.1667 0.2135 0.1498 0.039 Uiso 1 1 calc R . . H17C H -0.1996 0.3531 0.1428 0.039 Uiso 1 1 calc R . . C18 C -0.0494(8) 0.0019(13) 0.3214(8) 0.064(4) Uani 1 1 d . . . H18A H -0.0607 0.0725 0.3615 0.076 Uiso 1 1 calc R . . H18B H -0.0991 -0.0013 0.2725 0.076 Uiso 1 1 calc R . . C19 C -0.0466(8) -0.1104(11) 0.3734(9) 0.054(3) Uani 1 1 d . . . H19A H -0.0744 -0.1783 0.3366 0.065 Uiso 1 1 calc R . . H19B H -0.0805 -0.1011 0.4292 0.065 Uiso 1 1 calc R . . C20 C 0.0522(8) -0.1350(12) 0.3971(8) 0.050(3) Uani 1 1 d . . . H20A H 0.0710 -0.1023 0.4583 0.060 Uiso 1 1 calc R . . H20B H 0.0651 -0.2239 0.3963 0.060 Uiso 1 1 calc R . . C21 C 0.1000(7) -0.0715(11) 0.3263(9) 0.052(3) Uani 1 1 d . . . H21A H 0.1546 -0.0286 0.3539 0.062 Uiso 1 1 calc R . . H21B H 0.1206 -0.1312 0.2813 0.062 Uiso 1 1 calc R . . 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 0.01717(18) 0.01428(18) 0.0227(2) 0.00157(13) 0.00822(12) 0.00295(12) Br1 0.0176(4) 0.0417(5) 0.0328(5) 0.0039(4) 0.0015(4) 0.0054(4) Br2 0.0254(4) 0.0207(4) 0.0356(5) -0.0076(4) 0.0190(4) -0.0064(3) O7 0.034(4) 0.051(4) 0.029(4) 0.019(3) 0.003(3) 0.011(3) N1 0.019(3) 0.017(3) 0.020(4) -0.005(3) 0.009(3) 0.002(3) N2 0.019(3) 0.018(3) 0.019(4) -0.002(3) 0.008(3) 0.000(3) C1 0.018(4) 0.014(4) 0.017(4) -0.004(3) 0.003(3) 0.002(3) C2 0.031(5) 0.015(4) 0.026(5) 0.000(4) -0.002(4) 0.007(4) C3 0.029(5) 0.021(4) 0.025(5) -0.001(4) -0.002(4) 0.008(4) C4 0.040(5) 0.019(4) 0.016(4) 0.002(4) 0.009(4) 0.008(4) C5 0.025(4) 0.017(4) 0.021(5) 0.006(4) 0.011(4) -0.003(3) C6 0.027(4) 0.007(4) 0.032(5) -0.006(4) 0.009(4) 0.007(3) C7 0.022(4) 0.029(5) 0.028(5) 0.006(4) 0.010(4) -0.005(4) C8 0.028(5) 0.052(6) 0.026(5) 0.015(5) 0.008(4) -0.003(5) C9 0.014(4) 0.018(4) 0.021(4) -0.005(4) 0.001(3) -0.001(3) C10 0.025(4) 0.011(4) 0.012(4) -0.003(3) 0.008(3) 0.006(3) C11 0.024(4) 0.015(4) 0.031(5) 0.001(4) 0.012(4) 0.003(3) C12 0.038(5) 0.016(4) 0.031(5) -0.001(4) 0.022(4) 0.006(4) C13 0.051(6) 0.019(4) 0.027(5) -0.004(4) 0.028(5) 0.003(4) C14 0.043(6) 0.019(4) 0.018(5) -0.002(4) 0.010(4) 0.003(4) C15 0.035(5) 0.016(4) 0.020(5) 0.001(4) 0.012(4) 0.000(4) C16 0.035(5) 0.032(5) 0.035(6) -0.013(5) 0.001(4) -0.001(4) C17 0.018(4) 0.025(4) 0.035(5) -0.008(4) 0.008(4) 0.006(4) C18 0.045(7) 0.094(10) 0.057(8) 0.041(8) 0.037(6) 0.035(7) C19 0.035(6) 0.048(7) 0.081(10) 0.015(6) 0.015(6) -0.008(5) C20 0.053(7) 0.054(7) 0.045(7) 0.017(6) 0.015(6) 0.000(6) C21 0.024(5) 0.062(8) 0.070(8) 0.041(7) 0.009(5) 0.011(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Bi1 N1 2.291(7) . ? Bi1 N2 2.353(7) . ? Bi1 O7 2.634(6) . ? Bi1 Br1 2.6856(11) . ? Bi1 C9 2.750(8) . ? Bi1 Br2 2.9281(11) 3 ? Bi1 Br2 3.0671(11) . ? Br2 Bi1 2.9281(11) 3 ? O7 C21 1.415(11) . ? O7 C18 1.448(11) . ? N1 C9 1.315(10) . ? N1 C1 1.436(10) . ? N2 C9 1.328(10) . ? N2 C10 1.420(9) . ? C1 C6 1.403(11) . ? C1 C2 1.422(11) . ? C2 C3 1.388(12) . ? C2 C8 1.496(12) . ? C3 C4 1.372(12) . ? C3 H3 0.9500 . ? C4 C5 1.374(12) . ? C4 H4 0.9500 . ? C5 C6 1.392(12) . ? C5 H5 0.9500 . ? C6 C7 1.520(12) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9 0.9500 . ? C10 C11 1.404(11) . ? C10 C15 1.410(12) . ? C11 C12 1.392(11) . ? C11 C17 1.504(12) . ? C12 C13 1.359(14) . ? C12 H12 0.9500 . ? C13 C14 1.394(13) . ? C13 H13 0.9500 . ? C14 C15 1.412(11) . ? C14 H14 0.9500 . ? C15 C16 1.475(13) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.445(16) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.488(16) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.463(14) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? 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 N1 Bi1 N2 57.2(2) . . ? N1 Bi1 O7 134.2(2) . . ? N2 Bi1 O7 77.0(2) . . ? N1 Bi1 Br1 96.76(16) . . ? N2 Bi1 Br1 96.73(16) . . ? O7 Bi1 Br1 88.76(15) . . ? N1 Bi1 C9 28.4(2) . . ? N2 Bi1 C9 28.8(2) . . ? O7 Bi1 C9 105.8(2) . . ? Br1 Bi1 C9 99.11(16) . . ? N1 Bi1 Br2 82.08(16) . 3 ? N2 Bi1 Br2 139.03(16) . 3 ? O7 Bi1 Br2 143.40(16) . 3 ? Br1 Bi1 Br2 91.96(4) . 3 ? C9 Bi1 Br2 110.23(17) . 3 ? N1 Bi1 Br2 94.83(16) . . ? N2 Bi1 Br2 92.48(16) . . ? O7 Bi1 Br2 85.67(15) . . ? Br1 Bi1 Br2 167.89(3) . . ? C9 Bi1 Br2 92.75(16) . . ? Br2 Bi1 Br2 86.18(3) 3 . ? Bi1 Br2 Bi1 93.82(3) 3 . ? C21 O7 C18 108.3(7) . . ? C21 O7 Bi1 119.9(6) . . ? C18 O7 Bi1 126.3(6) . . ? C9 N1 C1 124.4(7) . . ? C9 N1 Bi1 95.6(5) . . ? C1 N1 Bi1 139.4(5) . . ? C9 N2 C10 124.1(7) . . ? C9 N2 Bi1 92.4(5) . . ? C10 N2 Bi1 142.7(5) . . ? C6 C1 C2 120.9(8) . . ? C6 C1 N1 119.4(7) . . ? C2 C1 N1 119.6(7) . . ? C3 C2 C1 116.9(8) . . ? C3 C2 C8 121.9(8) . . ? C1 C2 C8 121.1(8) . . ? C4 C3 C2 122.8(9) . . ? C4 C3 H3 118.6 . . ? C2 C3 H3 118.6 . . ? C3 C4 C5 119.5(8) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C4 C5 C6 121.2(8) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C5 C6 C1 118.6(8) . . ? C5 C6 C7 121.2(7) . . ? C1 C6 C7 120.2(8) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C2 C8 H8A 109.5 . . ? C2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 C9 N2 114.6(7) . . ? N1 C9 Bi1 56.0(4) . . ? N2 C9 Bi1 58.8(4) . . ? N1 C9 H9 122.7 . . ? N2 C9 H9 122.7 . . ? Bi1 C9 H9 175.7 . . ? C11 C10 C15 121.8(7) . . ? C11 C10 N2 120.2(7) . . ? C15 C10 N2 118.0(7) . . ? C12 C11 C10 117.8(8) . . ? C12 C11 C17 120.7(8) . . ? C10 C11 C17 121.4(7) . . ? C13 C12 C11 121.9(9) . . ? C13 C12 H12 119.0 . . ? C11 C12 H12 119.0 . . ? C12 C13 C14 120.6(8) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C13 C14 C15 120.2(9) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C10 C15 C14 117.6(8) . . ? C10 C15 C16 122.5(7) . . ? C14 C15 C16 119.9(8) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C11 C17 H17A 109.5 . . ? C11 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C11 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 O7 106.7(9) . . ? C19 C18 H18A 110.4 . . ? O7 C18 H18A 110.4 . . ? C19 C18 H18B 110.4 . . ? O7 C18 H18B 110.4 . . ? H18A C18 H18B 108.6 . . ? C18 C19 C20 105.8(9) . . ? C18 C19 H19A 110.6 . . ? C20 C19 H19A 110.6 . . ? C18 C19 H19B 110.6 . . ? C20 C19 H19B 110.6 . . ? H19A C19 H19B 108.7 . . ? C21 C20 C19 104.2(9) . . ? C21 C20 H20A 110.9 . . ? C19 C20 H20A 110.9 . . ? C21 C20 H20B 110.9 . . ? C19 C20 H20B 110.9 . . ? H20A C20 H20B 108.9 . . ? O7 C21 C20 108.7(8) . . ? O7 C21 H21A 109.9 . . ? C20 C21 H21A 109.9 . . ? O7 C21 H21B 109.9 . . ? C20 C21 H21B 109.9 . . ? H21A C21 H21B 108.3 . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 4.729 _refine_diff_density_min -3.226 _refine_diff_density_rms 0.298 # Attachment '2d.CIF' data_2d _database_code_depnum_ccdc_archive 'CCDC 643177' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H38 Bi Br N4, 2(C4 H8 O)' _chemical_formula_sum 'C42 H54 Bi Br N4 O2' _chemical_formula_weight 935.78 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' N N 0.0061 0.0033 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n a 21' _symmetry_space_group_name_Hall 'P 2c -2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 20.719(4) _cell_length_b 7.7269(15) _cell_length_c 24.432(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3911.5(13) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.589 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1872 _exptl_absorpt_coefficient_mu 5.569 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.545 _exptl_absorpt_correction_T_max 0.596 _exptl_absorpt_process_details SORTAV _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius KAPPA CCD' _diffrn_measurement_method '1 deg frames in phi and omega' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16563 _diffrn_reflns_av_R_equivalents 0.0563 _diffrn_reflns_av_sigmaI/netI 0.0514 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.81 _diffrn_reflns_theta_max 27.49 _reflns_number_total 6631 _reflns_number_gt 5879 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Bruker ASX, 2004)' _computing_cell_refinement 'DENZO-SMN (Bruker 2004)' _computing_data_reduction 'DENZO-SMN (Bruker 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1205P)^2^+2.8033P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.196(13) _refine_ls_number_reflns 6631 _refine_ls_number_parameters 479 _refine_ls_number_restraints 333 _refine_ls_R_factor_all 0.0685 _refine_ls_R_factor_gt 0.0606 _refine_ls_wR_factor_ref 0.1584 _refine_ls_wR_factor_gt 0.1509 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.008 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 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 _atom_site_disorder_assembly _atom_site_disorder_group Bi1 Bi 0.464511(13) 0.28029(4) -0.00089(3) 0.02216(12) Uani 1 1 d U . . Br1 Br 0.36005(5) 0.11374(15) 0.04329(5) 0.0349(2) Uani 1 1 d U . . O1 O 0.3828(4) 0.3209(15) -0.1022(4) 0.050(2) Uani 1 1 d U . . O2 O 0.2255(17) 1.040(7) 0.1981(14) 0.158(19) Uani 0.55 1 d PU A 1 O2' O 0.2756(13) 0.961(3) 0.2403(12) 0.069(7) Uani 0.45 1 d PU B 2 N1 N 0.5349(4) 0.0714(14) 0.0269(4) 0.026(2) Uani 1 1 d U . . N2 N 0.5085(4) 0.0497(10) -0.0615(3) 0.0232(16) Uani 1 1 d U . . N3 N 0.4911(4) 0.4519(11) 0.0747(3) 0.0248(17) Uani 1 1 d U . . N4 N 0.5599(3) 0.4753(9) 0.0057(3) 0.0193(14) Uani 1 1 d U . . C1 C 0.5789(5) 0.0419(13) 0.0708(4) 0.026(2) Uani 1 1 d U . . C2 C 0.5543(5) -0.0125(13) 0.1223(5) 0.028(2) Uani 1 1 d U . . C3 C 0.5984(7) -0.0563(19) 0.1642(4) 0.046(3) Uani 1 1 d U . . H3 H 0.5830 -0.1010 0.1979 0.055 Uiso 1 1 calc R . . C4 C 0.6642(6) -0.034(2) 0.1562(5) 0.047(3) Uani 1 1 d U . . H4 H 0.6933 -0.0581 0.1853 0.057 Uiso 1 1 calc R . . C5 C 0.6877(6) 0.021(2) 0.1069(5) 0.048(3) Uani 1 1 d U . . H5 H 0.7331 0.0316 0.1023 0.057 Uiso 1 1 calc R . . C6 C 0.6479(5) 0.0634(14) 0.0636(4) 0.027(2) Uani 1 1 d U . . C7 C 0.4834(6) -0.0254(16) 0.1313(5) 0.033(3) Uani 1 1 d U . . H7A H 0.4655 0.0906 0.1372 0.049 Uiso 1 1 calc R . . H7B H 0.4749 -0.0975 0.1635 0.049 Uiso 1 1 calc R . . H7C H 0.4631 -0.0777 0.0991 0.049 Uiso 1 1 calc R . . C8 C 0.6755(5) 0.1256(16) 0.0102(4) 0.036(3) Uani 1 1 d U . . H8A H 0.7189 0.1720 0.0164 0.054 Uiso 1 1 calc R . . H8B H 0.6478 0.2165 -0.0049 0.054 Uiso 1 1 calc R . . H8C H 0.6778 0.0287 -0.0156 0.054 Uiso 1 1 calc R . . C9 C 0.5436(4) -0.0083(17) -0.0214(4) 0.026(2) Uani 1 1 d U . . H9 H 0.5734 -0.1007 -0.0259 0.031 Uiso 1 1 calc R . . C10 C 0.5052(5) -0.0220(14) -0.1144(4) 0.024(2) Uani 1 1 d U . . C11 C 0.4506(5) -0.1117(16) -0.1315(5) 0.028(2) Uani 1 1 d U . . C12 C 0.4442(6) -0.1648(17) -0.1859(5) 0.036(3) Uani 1 1 d U . . H12 H 0.4061 -0.2224 -0.1976 0.044 Uiso 1 1 calc R . . C13 C 0.4924(6) -0.1340(17) -0.2220(4) 0.039(3) Uani 1 1 d U . . H13 H 0.4880 -0.1721 -0.2588 0.046 Uiso 1 1 calc R . . C14 C 0.5493(6) -0.0463(15) -0.2062(5) 0.032(2) Uani 1 1 d U . . H14 H 0.5826 -0.0272 -0.2322 0.038 Uiso 1 1 calc R . . C15 C 0.5569(5) 0.0131(14) -0.1520(4) 0.027(2) Uani 1 1 d U . . C16 C 0.6171(6) 0.1040(17) -0.1350(5) 0.038(3) Uani 1 1 d U . . H16A H 0.6465 0.0212 -0.1176 0.056 Uiso 1 1 calc R . . H16B H 0.6064 0.1962 -0.1090 0.056 Uiso 1 1 calc R . . H16C H 0.6380 0.1543 -0.1673 0.056 Uiso 1 1 calc R . . C17 C 0.3987(5) -0.1534(18) -0.0900(5) 0.040(3) Uani 1 1 d U . . H17A H 0.4179 -0.2147 -0.0589 0.060 Uiso 1 1 calc R . . H17B H 0.3657 -0.2269 -0.1070 0.060 Uiso 1 1 calc R . . H17C H 0.3787 -0.0458 -0.0772 0.060 Uiso 1 1 calc R . . C18 C 0.4604(5) 0.5120(16) 0.1244(5) 0.031(3) Uani 1 1 d U . . C19 C 0.4945(6) 0.5061(14) 0.1741(4) 0.033(2) Uani 1 1 d U . . C20 C 0.4640(7) 0.555(2) 0.2214(6) 0.049(4) Uani 1 1 d U . . H20 H 0.4858 0.5469 0.2554 0.059 Uiso 1 1 calc R . . C21 C 0.4023(8) 0.6159(18) 0.2196(6) 0.057(4) Uani 1 1 d U . . H21 H 0.3816 0.6499 0.2526 0.069 Uiso 1 1 calc R . . C22 C 0.3682(6) 0.6294(16) 0.1692(6) 0.046(3) Uani 1 1 d U . . H22 H 0.3255 0.6740 0.1684 0.056 Uiso 1 1 calc R . . C23 C 0.3982(5) 0.5764(14) 0.1215(5) 0.037(3) Uani 1 1 d U . . C24 C 0.3639(6) 0.5994(18) 0.0683(6) 0.051(4) Uani 1 1 d U . . H24A H 0.3947 0.6383 0.0404 0.076 Uiso 1 1 calc R . . H24B H 0.3298 0.6861 0.0725 0.076 Uiso 1 1 calc R . . H24C H 0.3449 0.4890 0.0570 0.076 Uiso 1 1 calc R . . C25 C 0.5634(7) 0.4450(17) 0.1763(5) 0.044(3) Uani 1 1 d U . . H25A H 0.5917 0.5335 0.1604 0.065 Uiso 1 1 calc R . . H25B H 0.5677 0.3372 0.1555 0.065 Uiso 1 1 calc R . . H25C H 0.5758 0.4247 0.2145 0.065 Uiso 1 1 calc R . . C26 C 0.5389(4) 0.5348(14) 0.0520(5) 0.023(2) Uani 1 1 d U . . H26 H 0.5575 0.6341 0.0687 0.028 Uiso 1 1 calc R . . C27 C 0.6100(4) 0.5494(13) -0.0251(4) 0.0235(19) Uani 1 1 d U . . C28 C 0.6713(4) 0.5872(12) 0.0004(6) 0.0295(19) Uani 1 1 d U . . C29 C 0.7194(5) 0.6550(17) -0.0330(5) 0.037(3) Uani 1 1 d U . . H29 H 0.7598 0.6861 -0.0174 0.044 Uiso 1 1 calc R . . C30 C 0.7098(5) 0.6782(18) -0.0889(5) 0.035(2) Uani 1 1 d U . . H30 H 0.7438 0.7229 -0.1108 0.042 Uiso 1 1 calc R . . C31 C 0.6532(5) 0.6386(15) -0.1123(4) 0.030(2) Uani 1 1 d U . . H31 H 0.6478 0.6568 -0.1505 0.036 Uiso 1 1 calc R . . C32 C 0.6019(4) 0.5714(11) -0.0820(4) 0.0212(18) Uani 1 1 d U . . C33 C 0.5391(4) 0.5260(17) -0.1082(5) 0.030(2) Uani 1 1 d U . . H33A H 0.5383 0.5703 -0.1458 0.045 Uiso 1 1 calc R . . H33B H 0.5037 0.5780 -0.0873 0.045 Uiso 1 1 calc R . . H33C H 0.5340 0.3999 -0.1087 0.045 Uiso 1 1 calc R . . C34 C 0.6844(5) 0.5532(19) 0.0582(4) 0.039(3) Uani 1 1 d U . . H34A H 0.7304 0.5281 0.0630 0.058 Uiso 1 1 calc R . . H34B H 0.6589 0.4536 0.0703 0.058 Uiso 1 1 calc R . . H34C H 0.6727 0.6551 0.0799 0.058 Uiso 1 1 calc R . . C35 C 0.3156(8) 0.328(4) -0.0968(9) 0.088(7) Uani 1 1 d U . . H35A H 0.3010 0.4495 -0.0922 0.106 Uiso 1 1 calc R . . H35B H 0.3012 0.2602 -0.0647 0.106 Uiso 1 1 calc R . . C36 C 0.2879(10) 0.250(4) -0.151(2) 0.130(17) Uani 1 1 d U . . H36A H 0.2670 0.1365 -0.1439 0.156 Uiso 1 1 calc R . . H36B H 0.2559 0.3286 -0.1677 0.156 Uiso 1 1 calc R . . C37 C 0.3410(10) 0.230(2) -0.1847(9) 0.073(6) Uani 1 1 d U . . H37A H 0.3319 0.2792 -0.2213 0.087 Uiso 1 1 calc R . . H37B H 0.3513 0.1054 -0.1892 0.087 Uiso 1 1 calc R . . C38 C 0.3966(6) 0.3222(19) -0.1589(5) 0.042(3) Uani 1 1 d U . . H38A H 0.4377 0.2612 -0.1665 0.050 Uiso 1 1 calc R . . H38B H 0.3999 0.4423 -0.1727 0.050 Uiso 1 1 calc R . . C39 C 0.2925(9) 1.063(4) 0.1908(7) 0.091(7) Uani 0.55 1 d PU A 1 H39A H 0.3047 1.0625 0.1517 0.109 Uiso 0.55 1 calc PR A 1 H39B H 0.3178 0.9741 0.2106 0.109 Uiso 0.55 1 calc PR A 1 C39' C 0.2925(9) 1.063(4) 0.1908(7) 0.091(7) Uani 0.45 1 d PU B 2 H39C H 0.2574 1.0607 0.1633 0.109 Uiso 0.45 1 calc PR B 2 H39D H 0.3331 1.0219 0.1739 0.109 Uiso 0.45 1 calc PR B 2 C40 C 0.3000(11) 1.238(3) 0.2158(16) 0.113(14) Uani 0.55 1 d PU A 1 H40A H 0.3419 1.2450 0.2352 0.135 Uiso 0.55 1 calc PR A 1 H40B H 0.2993 1.3273 0.1869 0.135 Uiso 0.55 1 calc PR A 1 C40' C 0.3000(11) 1.238(3) 0.2158(16) 0.113(14) Uani 0.45 1 d PDU B 2 H40C H 0.3419 1.2450 0.2352 0.135 Uiso 0.45 1 calc PR B 2 H40D H 0.2993 1.3273 0.1869 0.135 Uiso 0.45 1 calc PR B 2 C41 C 0.250(2) 1.265(3) 0.2520(14) 0.20(2) Uani 0.55 1 d PU A 1 H41A H 0.2270 1.3726 0.2427 0.234 Uiso 0.55 1 calc PR A 1 H41B H 0.2672 1.2749 0.2897 0.234 Uiso 0.55 1 calc PR A 1 C41' C 0.250(2) 1.265(3) 0.2520(14) 0.20(2) Uani 0.45 1 d PDU B 2 H41C H 0.2605 1.3519 0.2803 0.234 Uiso 0.45 1 calc PR B 2 H41D H 0.2089 1.2927 0.2337 0.234 Uiso 0.45 1 calc PR B 2 C42 C 0.2047(10) 1.109(4) 0.2477(10) 0.046(6) Uani 0.55 1 d PU A 1 H42A H 0.2108 1.0274 0.2784 0.055 Uiso 0.55 1 calc PR A 1 H42B H 0.1589 1.1458 0.2462 0.055 Uiso 0.55 1 calc PR A 1 C42' C 0.253(2) 1.099(3) 0.2710(12) 0.056(10) Uani 0.45 1 d PDU B 2 H42C H 0.2083 1.0685 0.2823 0.067 Uiso 0.45 1 calc PR B 2 H42D H 0.2790 1.1022 0.3049 0.067 Uiso 0.45 1 calc PR B 2 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 0.02296(17) 0.02721(19) 0.01630(17) -0.0032(2) 0.00264(18) 0.00013(10) Br1 0.0297(5) 0.0430(6) 0.0320(5) -0.0014(5) 0.0082(4) -0.0066(4) O1 0.041(5) 0.072(6) 0.036(5) 0.019(5) -0.001(4) 0.013(5) O2 0.13(3) 0.26(5) 0.09(2) -0.10(3) -0.008(19) 0.01(3) O2' 0.102(19) 0.037(11) 0.068(17) 0.006(12) 0.029(14) 0.019(12) N1 0.033(5) 0.029(5) 0.016(5) -0.008(4) -0.004(3) 0.004(3) N2 0.030(4) 0.019(4) 0.020(4) -0.006(3) 0.005(3) 0.011(3) N3 0.040(4) 0.022(4) 0.012(4) -0.004(3) 0.002(3) -0.001(3) N4 0.026(3) 0.026(3) 0.006(4) 0.006(3) 0.001(3) 0.001(3) C1 0.034(5) 0.027(5) 0.016(4) -0.004(4) -0.001(4) 0.010(4) C2 0.039(5) 0.020(5) 0.024(6) -0.005(4) -0.009(5) -0.011(4) C3 0.070(9) 0.061(8) 0.006(4) 0.007(5) 0.003(5) 0.016(7) C4 0.053(7) 0.073(9) 0.016(5) -0.005(6) -0.010(5) 0.003(7) C5 0.044(7) 0.070(9) 0.029(6) -0.011(6) -0.003(5) 0.017(6) C6 0.031(5) 0.032(5) 0.018(5) -0.006(4) 0.004(4) 0.006(4) C7 0.048(6) 0.033(6) 0.018(5) 0.002(5) 0.012(5) -0.009(6) C8 0.032(5) 0.051(7) 0.024(7) 0.005(5) 0.007(4) -0.009(4) C9 0.024(5) 0.040(7) 0.013(4) -0.003(5) 0.004(3) 0.006(4) C10 0.032(6) 0.027(5) 0.012(5) -0.003(4) 0.006(4) 0.003(4) C11 0.026(5) 0.033(6) 0.024(5) -0.003(5) -0.001(4) 0.008(4) C12 0.040(6) 0.036(6) 0.033(6) -0.005(5) -0.020(5) 0.009(5) C13 0.050(7) 0.050(8) 0.015(5) -0.009(5) -0.001(5) 0.015(6) C14 0.040(5) 0.029(6) 0.026(6) -0.001(5) 0.005(4) 0.002(4) C15 0.031(5) 0.033(6) 0.017(5) 0.003(4) 0.012(4) 0.003(4) C16 0.039(6) 0.041(6) 0.032(6) 0.003(5) 0.013(5) 0.003(5) C17 0.034(6) 0.050(7) 0.036(6) -0.016(6) 0.008(5) -0.004(5) C18 0.044(6) 0.028(6) 0.021(6) -0.006(5) 0.018(4) -0.005(4) C19 0.058(7) 0.026(5) 0.015(5) -0.006(4) 0.006(5) -0.019(5) C20 0.078(10) 0.045(8) 0.025(7) -0.007(6) 0.011(6) -0.013(6) C21 0.092(11) 0.040(7) 0.039(7) -0.028(6) 0.036(7) -0.022(7) C22 0.053(7) 0.037(7) 0.048(8) -0.020(6) 0.032(6) -0.008(5) C23 0.044(6) 0.027(5) 0.040(7) -0.007(5) 0.016(5) -0.013(5) C24 0.037(6) 0.043(7) 0.073(10) -0.013(7) 0.007(6) -0.002(5) C25 0.071(9) 0.041(7) 0.018(5) 0.008(5) -0.010(6) -0.018(6) C26 0.026(5) 0.023(5) 0.021(5) 0.002(4) -0.011(4) -0.005(3) C27 0.026(5) 0.027(4) 0.017(4) 0.007(4) 0.001(4) 0.007(4) C28 0.026(4) 0.035(5) 0.028(5) -0.019(6) -0.010(5) 0.007(3) C29 0.027(5) 0.050(7) 0.034(7) -0.001(5) -0.004(4) -0.001(5) C30 0.031(6) 0.052(7) 0.022(6) 0.011(5) 0.007(4) -0.003(5) C31 0.029(5) 0.041(6) 0.020(5) -0.003(4) 0.003(4) 0.002(4) C32 0.026(4) 0.017(4) 0.021(5) -0.001(4) 0.002(4) 0.004(3) C33 0.030(6) 0.043(7) 0.017(5) 0.008(5) -0.002(4) 0.005(4) C34 0.031(5) 0.063(8) 0.022(5) 0.004(5) -0.002(4) -0.004(5) C35 0.038(8) 0.15(2) 0.072(13) 0.010(14) 0.007(8) 0.030(11) C36 0.054(16) 0.14(3) 0.19(5) 0.08(2) -0.020(16) -0.022(15) C37 0.086(13) 0.055(9) 0.077(13) -0.019(9) -0.051(11) 0.039(9) C38 0.042(7) 0.049(7) 0.035(7) 0.004(6) 0.010(5) 0.008(6) C39 0.075(12) 0.16(2) 0.033(9) 0.017(12) -0.005(8) -0.003(13) C39' 0.075(12) 0.16(2) 0.033(9) 0.017(12) -0.005(8) -0.003(13) C40 0.052(11) 0.073(13) 0.21(4) 0.025(18) -0.051(19) -0.024(9) C40' 0.052(11) 0.073(13) 0.21(4) 0.025(18) -0.051(19) -0.024(9) C41 0.20(4) 0.20(4) 0.19(4) -0.14(3) -0.09(4) 0.10(3) C41' 0.20(4) 0.20(4) 0.19(4) -0.14(3) -0.09(4) 0.10(3) C42 0.017(9) 0.080(18) 0.040(13) -0.007(13) 0.006(8) 0.000(10) C42' 0.11(3) 0.022(13) 0.031(14) 0.010(12) 0.023(17) 0.038(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Bi1 N1 2.279(10) . ? Bi1 N3 2.339(8) . ? Bi1 N2 2.490(7) . ? Bi1 N4 2.490(7) . ? Bi1 Br1 2.7397(11) . ? Bi1 C9 2.812(12) . ? Bi1 C26 2.814(10) . ? Bi1 O1 3.016(9) . ? O1 C35 1.400(18) . ? O1 C38 1.413(16) . ? O2 C42 1.40(4) . ? O2 C39 1.41(3) . ? O2' C42' 1.39(3) . ? N1 C9 1.343(14) . ? N1 C1 1.425(13) . ? N2 C9 1.302(14) . ? N2 C10 1.406(12) . ? N3 C26 1.303(12) . ? N3 C18 1.449(13) . ? N4 C26 1.296(14) . ? N4 C27 1.406(12) . ? C1 C2 1.421(15) . ? C1 C6 1.450(14) . ? C2 C3 1.412(16) . ? C2 C7 1.489(16) . ? C3 C4 1.387(19) . ? C4 C5 1.368(18) . ? C5 C6 1.380(16) . ? C6 C8 1.503(13) . ? C10 C11 1.392(15) . ? C10 C15 1.437(14) . ? C11 C12 1.398(16) . ? C11 C17 1.513(16) . ? C12 C13 1.355(19) . ? C13 C14 1.412(17) . ? C14 C15 1.410(15) . ? C15 C16 1.491(17) . ? C18 C23 1.383(16) . ? C18 C19 1.405(16) . ? C19 C20 1.370(17) . ? C19 C25 1.51(2) . ? C20 C21 1.36(2) . ? C21 C22 1.42(2) . ? C22 C23 1.383(16) . ? C23 C24 1.491(19) . ? C27 C32 1.410(13) . ? C27 C28 1.445(13) . ? C28 C29 1.392(17) . ? C28 C34 1.461(17) . ? C29 C30 1.392(17) . ? C30 C31 1.340(16) . ? C31 C32 1.395(14) . ? C32 C33 1.493(13) . ? C35 C36 1.57(5) . ? C36 C37 1.38(4) . ? C37 C38 1.50(2) . ? C39 C40 1.49(4) . ? C40 C41 1.374(19) . ? C41 C42 1.53(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 N1 Bi1 N3 90.9(3) . . ? N1 Bi1 N2 55.7(3) . . ? N3 Bi1 N2 142.1(3) . . ? N1 Bi1 N4 84.3(3) . . ? N3 Bi1 N4 54.5(3) . . ? N2 Bi1 N4 100.5(3) . . ? N1 Bi1 Br1 93.2(2) . . ? N3 Bi1 Br1 98.1(2) . . ? N2 Bi1 Br1 100.8(2) . . ? N4 Bi1 Br1 152.31(19) . . ? N1 Bi1 C9 28.2(3) . . ? N3 Bi1 C9 116.9(3) . . ? N2 Bi1 C9 27.6(3) . . ? N4 Bi1 C9 91.7(3) . . ? Br1 Bi1 C9 99.1(2) . . ? N1 Bi1 C26 90.4(3) . . ? N3 Bi1 C26 27.4(3) . . ? N2 Bi1 C26 125.0(3) . . ? N4 Bi1 C26 27.4(3) . . ? Br1 Bi1 C26 125.5(2) . . ? C9 Bi1 C26 108.5(3) . . ? C35 O1 C38 107.1(12) . . ? C42 O2 C39 111(3) . . ? C9 N1 C1 120.1(8) . . ? C9 N1 Bi1 98.5(7) . . ? C1 N1 Bi1 138.3(8) . . ? C9 N2 C10 125.7(9) . . ? C9 N2 Bi1 90.1(6) . . ? C10 N2 Bi1 144.1(6) . . ? C26 N3 C18 122.2(9) . . ? C26 N3 Bi1 97.0(6) . . ? C18 N3 Bi1 137.8(7) . . ? C26 N4 C27 124.9(8) . . ? C26 N4 Bi1 90.3(5) . . ? C27 N4 Bi1 142.9(7) . . ? C2 C1 N1 119.0(9) . . ? C2 C1 C6 119.6(9) . . ? N1 C1 C6 121.4(9) . . ? C3 C2 C1 118.7(10) . . ? C3 C2 C7 121.1(10) . . ? C1 C2 C7 120.2(10) . . ? C4 C3 C2 120.3(10) . . ? C5 C4 C3 120.8(11) . . ? C4 C5 C6 122.3(12) . . ? C5 C6 C1 118.0(10) . . ? C5 C6 C8 120.8(10) . . ? C1 C6 C8 121.2(9) . . ? N2 C9 N1 115.5(9) . . ? N2 C9 Bi1 62.3(6) . . ? N1 C9 Bi1 53.3(5) . . ? C11 C10 N2 120.8(9) . . ? C11 C10 C15 120.5(10) . . ? N2 C10 C15 118.5(9) . . ? C10 C11 C12 120.6(11) . . ? C10 C11 C17 118.9(10) . . ? C12 C11 C17 120.5(11) . . ? C13 C12 C11 119.9(11) . . ? C12 C13 C14 121.4(10) . . ? C15 C14 C13 120.5(10) . . ? C14 C15 C10 117.1(10) . . ? C14 C15 C16 120.5(9) . . ? C10 C15 C16 122.3(9) . . ? C23 C18 C19 121.7(11) . . ? C23 C18 N3 118.8(11) . . ? C19 C18 N3 119.5(9) . . ? C20 C19 C18 119.1(12) . . ? C20 C19 C25 119.7(11) . . ? C18 C19 C25 121.3(9) . . ? C21 C20 C19 120.1(14) . . ? C20 C21 C22 121.3(12) . . ? C23 C22 C21 119.0(12) . . ? C18 C23 C22 118.8(12) . . ? C18 C23 C24 122.1(10) . . ? C22 C23 C24 119.1(12) . . ? N4 C26 N3 116.8(9) . . ? N4 C26 Bi1 62.3(5) . . ? N3 C26 Bi1 55.6(5) . . ? N4 C27 C32 119.3(9) . . ? N4 C27 C28 120.0(9) . . ? C32 C27 C28 120.4(9) . . ? C29 C28 C27 116.9(11) . . ? C29 C28 C34 120.1(9) . . ? C27 C28 C34 123.0(10) . . ? C28 C29 C30 121.4(11) . . ? C31 C30 C29 121.0(10) . . ? C30 C31 C32 121.7(10) . . ? C31 C32 C27 118.5(9) . . ? C31 C32 C33 121.6(9) . . ? C27 C32 C33 119.9(9) . . ? O1 C35 C36 105.5(18) . . ? C37 C36 C35 104.9(17) . . ? C36 C37 C38 108(2) . . ? O1 C38 C37 104.7(13) . . ? O2 C39 C40 100(2) . . ? C41 C40 C39 108.8(19) . . ? C40 C41 C42 107(2) . . ? O2 C42 C41 100(3) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 3.047 _refine_diff_density_min -5.400 _refine_diff_density_rms 0.217 # Attachment '2e.CIF' data_2e _database_code_depnum_ccdc_archive 'CCDC 643178' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C50 H38 Bi Br N4), C4 H10 O' _chemical_formula_sum 'C104 H86 Bi2 Br2 N8 O' _chemical_formula_weight 2041.59 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' N N 0.0061 0.0033 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 13.8771(2) _cell_length_b 18.1526(3) _cell_length_c 19.5760(3) _cell_angle_alpha 84.116(1) _cell_angle_beta 70.507(1) _cell_angle_gamma 67.968(1) _cell_volume 4307.73(12) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.574 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2020 _exptl_absorpt_coefficient_mu 5.062 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4109 _exptl_absorpt_correction_T_max 0.6115 _exptl_absorpt_process_details 'performed as part of the DENZO-SMN package' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius Kappa CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 39665 _diffrn_reflns_av_R_equivalents 0.0447 _diffrn_reflns_av_sigmaI/netI 0.0732 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 27.50 _reflns_number_total 19643 _reflns_number_gt 14530 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed / POV-Ray' _computing_publication_material 'Microsoft Office 2000' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0393P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 19643 _refine_ls_number_parameters 1056 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0674 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.0842 _refine_ls_wR_factor_gt 0.0757 _refine_ls_goodness_of_fit_ref 0.978 _refine_ls_restrained_S_all 0.978 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 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 _atom_site_disorder_assembly _atom_site_disorder_group Bi1 Bi 0.762151(14) 0.751779(10) 0.082412(8) 0.01600(5) Uani 1 1 d . . . Bi2 Bi 0.990235(13) 0.767421(9) -0.491941(7) 0.01436(5) Uani 1 1 d . . . Br1 Br 0.57412(4) 0.72392(3) 0.11968(2) 0.02366(11) Uani 1 1 d . . . Br2 Br 0.89836(4) 0.78153(3) -0.59750(2) 0.02105(10) Uani 1 1 d . . . O1 O 0.4033(5) 0.6393(3) -0.0465(3) 0.095(2) Uani 1 1 d . . . N1 N 0.8306(3) 0.6566(2) -0.01090(17) 0.0182(8) Uani 1 1 d . . . N2 N 0.9228(3) 0.7381(2) -0.02683(17) 0.0174(8) Uani 1 1 d . . . N3 N 0.6845(3) 0.8545(2) 0.01817(16) 0.0147(8) Uani 1 1 d . . . N4 N 0.6692(3) 0.9012(2) 0.12505(17) 0.0174(8) Uani 1 1 d . . . N5 N 1.0771(3) 0.8479(2) -0.56075(17) 0.0177(8) Uani 1 1 d . . . N6 N 1.1497(3) 0.7910(2) -0.47436(17) 0.0175(8) Uani 1 1 d . . . N7 N 1.1235(3) 0.6598(2) -0.55162(16) 0.0162(8) Uani 1 1 d . . . N8 N 1.0107(3) 0.6179(2) -0.45687(17) 0.0162(8) Uani 1 1 d . . . C1 C 0.8145(4) 0.5898(3) -0.0282(2) 0.0214(10) Uani 1 1 d . . . C1S C 0.4771(8) 0.6359(5) -0.0140(4) 0.084(3) Uani 1 1 d . . . H1S1 H 0.4715 0.6905 -0.0060 0.101 Uiso 1 1 calc R . . H1S2 H 0.5522 0.6070 -0.0465 0.101 Uiso 1 1 calc R . . C2 C 0.8073(4) 0.5827(3) -0.0966(2) 0.0293(12) Uani 1 1 d . . . H2 H 0.8133 0.6231 -0.1308 0.035 Uiso 1 1 calc R . . C2S C 0.4596(9) 0.5971(7) 0.0535(5) 0.123(4) Uani 1 1 d . . . H2S1 H 0.3925 0.6315 0.0891 0.185 Uiso 1 1 calc R . . H2S2 H 0.5222 0.5863 0.0707 0.185 Uiso 1 1 calc R . . H2S3 H 0.4519 0.5470 0.0473 0.185 Uiso 1 1 calc R . . C3 C 0.7915(5) 0.5174(3) -0.1151(3) 0.0344(13) Uani 1 1 d . . . H3 H 0.7879 0.5127 -0.1620 0.041 Uiso 1 1 calc R . . C3S C 0.4157(13) 0.6783(8) -0.1097(6) 0.173(7) Uani 1 1 d . . . H3S1 H 0.3913 0.7356 -0.0984 0.208 Uiso 1 1 calc R . . H3S2 H 0.4949 0.6599 -0.1377 0.208 Uiso 1 1 calc R . . C4 C 0.7810(5) 0.4598(3) -0.0654(3) 0.0356(13) Uani 1 1 d . . . H4 H 0.7699 0.4151 -0.0778 0.043 Uiso 1 1 calc R . . C4S C 0.3616(12) 0.6700(7) -0.1526(5) 0.153(6) Uani 1 1 d . . . H4S1 H 0.4082 0.6237 -0.1854 0.230 Uiso 1 1 calc R . . H4S2 H 0.3435 0.7179 -0.1811 0.230 Uiso 1 1 calc R . . H4S3 H 0.2939 0.6624 -0.1225 0.230 Uiso 1 1 calc R . . C5 C 0.7865(4) 0.4664(3) 0.0027(3) 0.0308(12) Uani 1 1 d . . . H5 H 0.7784 0.4261 0.0367 0.037 Uiso 1 1 calc R . . C6 C 0.8038(4) 0.5312(3) 0.0231(2) 0.0226(10) Uani 1 1 d . . . C7 C 0.8101(4) 0.5356(3) 0.0966(2) 0.0218(10) Uani 1 1 d . . . C8 C 0.8948(4) 0.5516(3) 0.1078(2) 0.0274(11) Uani 1 1 d . . . H8 H 0.9516 0.5585 0.0673 0.033 Uiso 1 1 calc R . . C9 C 0.8966(5) 0.5576(3) 0.1781(3) 0.0346(13) Uani 1 1 d . . . H9 H 0.9546 0.5681 0.1853 0.041 Uiso 1 1 calc R . . C10 C 0.8135(5) 0.5482(4) 0.2365(3) 0.0405(14) Uani 1 1 d . . . H10 H 0.8128 0.5542 0.2843 0.049 Uiso 1 1 calc R . . C11 C 0.7321(5) 0.5302(3) 0.2262(2) 0.0353(13) Uani 1 1 d . . . H11 H 0.6767 0.5218 0.2669 0.042 Uiso 1 1 calc R . . C12 C 0.7298(4) 0.5242(3) 0.1571(2) 0.0276(11) Uani 1 1 d . . . H12 H 0.6724 0.5120 0.1508 0.033 Uiso 1 1 calc R . . C13 C 0.9135(4) 0.6782(3) -0.0520(2) 0.0187(10) Uani 1 1 d . . . H13 H 0.9626 0.6516 -0.0966 0.022 Uiso 1 1 calc R . . C14 C 0.9922(4) 0.7775(3) -0.0661(2) 0.0159(9) Uani 1 1 d . . . C15 C 1.0228(4) 0.7800(3) -0.1424(2) 0.0203(10) Uani 1 1 d . . . H15 H 1.0028 0.7497 -0.1682 0.024 Uiso 1 1 calc R . . C16 C 1.0818(4) 0.8266(3) -0.1795(2) 0.0214(10) Uani 1 1 d . . . H16 H 1.1038 0.8271 -0.2309 0.026 Uiso 1 1 calc R . . C17 C 1.1091(4) 0.8722(3) -0.1428(2) 0.0239(11) Uani 1 1 d . . . H17 H 1.1468 0.9059 -0.1685 0.029 Uiso 1 1 calc R . . C18 C 1.0816(4) 0.8689(3) -0.0685(2) 0.0197(10) Uani 1 1 d . . . H18 H 1.1024 0.8996 -0.0436 0.024 Uiso 1 1 calc R . . C19 C 1.0240(4) 0.8217(3) -0.0287(2) 0.0172(9) Uani 1 1 d . . . C20 C 0.9938(4) 0.8205(3) 0.0520(2) 0.0185(10) Uani 1 1 d . . . C21 C 1.0209(5) 0.7495(3) 0.0878(2) 0.0334(13) Uani 1 1 d . . . H21 H 1.0548 0.7005 0.0611 0.040 Uiso 1 1 calc R . . C22 C 0.9992(6) 0.7495(4) 0.1618(3) 0.0516(17) Uani 1 1 d . . . H22 H 1.0192 0.7005 0.1855 0.062 Uiso 1 1 calc R . . C23 C 0.9483(5) 0.8205(4) 0.2022(3) 0.0456(16) Uani 1 1 d . . . H23 H 0.9337 0.8203 0.2532 0.055 Uiso 1 1 calc R . . C24 C 0.9194(4) 0.8913(3) 0.1668(2) 0.0349(13) Uani 1 1 d . . . H24 H 0.8842 0.9402 0.1936 0.042 Uiso 1 1 calc R . . C25 C 0.9417(4) 0.8912(3) 0.0920(2) 0.0227(11) Uani 1 1 d . . . H25 H 0.9209 0.9402 0.0682 0.027 Uiso 1 1 calc R . . C26 C 0.6636(4) 0.8621(3) -0.0489(2) 0.0170(9) Uani 1 1 d . . . C27 C 0.6385(4) 0.8030(3) -0.0703(2) 0.0201(10) Uani 1 1 d . . . H27 H 0.6393 0.7579 -0.0409 0.024 Uiso 1 1 calc R . . C28 C 0.6122(4) 0.8082(3) -0.1335(2) 0.0245(11) Uani 1 1 d . . . H28 H 0.5965 0.7665 -0.1477 0.029 Uiso 1 1 calc R . . C29 C 0.6090(4) 0.8748(3) -0.1758(2) 0.0237(11) Uani 1 1 d . . . H29 H 0.5899 0.8793 -0.2187 0.028 Uiso 1 1 calc R . . C30 C 0.6337(4) 0.9342(3) -0.1554(2) 0.0199(10) Uani 1 1 d . . . H30 H 0.6297 0.9799 -0.1843 0.024 Uiso 1 1 calc R . . C31 C 0.6645(3) 0.9293(3) -0.0931(2) 0.0155(9) Uani 1 1 d . . . C32 C 0.6981(4) 0.9937(3) -0.0795(2) 0.0157(9) Uani 1 1 d . . . C33 C 0.6300(4) 1.0736(3) -0.0766(2) 0.0259(11) Uani 1 1 d . . . H33 H 0.5590 1.0868 -0.0805 0.031 Uiso 1 1 calc R . . C34 C 0.6637(4) 1.1336(3) -0.0681(2) 0.0283(11) Uani 1 1 d . . . H34 H 0.6158 1.1875 -0.0657 0.034 Uiso 1 1 calc R . . C35 C 0.7669(4) 1.1154(3) -0.0631(2) 0.0267(11) Uani 1 1 d . . . H35 H 0.7903 1.1568 -0.0577 0.032 Uiso 1 1 calc R . . C36 C 0.8366(4) 1.0367(3) -0.0659(2) 0.0218(10) Uani 1 1 d . . . H36 H 0.9080 1.0240 -0.0628 0.026 Uiso 1 1 calc R . . C37 C 0.8017(4) 0.9769(3) -0.0732(2) 0.0175(10) Uani 1 1 d . . . H37 H 0.8492 0.9230 -0.0740 0.021 Uiso 1 1 calc R . . C38 C 0.6488(3) 0.9160(3) 0.0641(2) 0.0150(9) Uani 1 1 d . . . H38 H 0.6099 0.9685 0.0525 0.018 Uiso 1 1 calc R . . C39 C 0.6519(4) 0.9630(3) 0.1701(2) 0.0179(10) Uani 1 1 d . . . C40 C 0.6670(4) 1.0331(3) 0.1412(2) 0.0208(10) Uani 1 1 d . . . H40 H 0.6836 1.0404 0.0904 0.025 Uiso 1 1 calc R . . C41 C 0.6585(4) 1.0916(3) 0.1849(2) 0.0282(12) Uani 1 1 d . . . H41 H 0.6660 1.1398 0.1645 0.034 Uiso 1 1 calc R . . C42 C 0.6389(4) 1.0799(3) 0.2587(3) 0.0306(13) Uani 1 1 d . . . H42 H 0.6376 1.1184 0.2888 0.037 Uiso 1 1 calc R . . C43 C 0.6214(4) 1.0121(3) 0.2880(2) 0.0270(12) Uani 1 1 d . . . H43 H 0.6058 1.0052 0.3388 0.032 Uiso 1 1 calc R . . C44 C 0.6259(4) 0.9530(3) 0.2453(2) 0.0181(10) Uani 1 1 d . . . C45 C 0.6003(4) 0.8830(3) 0.2811(2) 0.0219(10) Uani 1 1 d . . . C46 C 0.6475(5) 0.8433(3) 0.3344(2) 0.0367(13) Uani 1 1 d . . . H46 H 0.7002 0.8581 0.3445 0.044 Uiso 1 1 calc R . . C47 C 0.6166(5) 0.7826(4) 0.3717(3) 0.0489(16) Uani 1 1 d . . . H47 H 0.6479 0.7564 0.4081 0.059 Uiso 1 1 calc R . . C48 C 0.5419(5) 0.7594(3) 0.3574(3) 0.0428(15) Uani 1 1 d . . . H48 H 0.5217 0.7176 0.3838 0.051 Uiso 1 1 calc R . . C49 C 0.4957(4) 0.7972(3) 0.3043(2) 0.0311(12) Uani 1 1 d . . . H49 H 0.4440 0.7813 0.2939 0.037 Uiso 1 1 calc R . . C50 C 0.5258(4) 0.8584(3) 0.2666(2) 0.0232(11) Uani 1 1 d . . . H50 H 0.4947 0.8839 0.2300 0.028 Uiso 1 1 calc R . . C51 C 1.0632(4) 0.9019(3) -0.6179(2) 0.0224(11) Uani 1 1 d . . . C52 C 1.1532(4) 0.8934(3) -0.6805(2) 0.0263(11) Uani 1 1 d . . . H52 H 1.2223 0.8527 -0.6844 0.032 Uiso 1 1 calc R . . C53 C 1.1406(5) 0.9453(3) -0.7371(2) 0.0345(14) Uani 1 1 d . . . H53 H 1.2014 0.9402 -0.7797 0.041 Uiso 1 1 calc R . . C54 C 1.0411(5) 1.0036(3) -0.7317(3) 0.0372(14) Uani 1 1 d . . . H54 H 1.0332 1.0387 -0.7706 0.045 Uiso 1 1 calc R . . C55 C 0.9520(5) 1.0119(3) -0.6702(2) 0.0311(12) Uani 1 1 d . . . H55 H 0.8831 1.0522 -0.6677 0.037 Uiso 1 1 calc R . . C56 C 0.9614(4) 0.9615(3) -0.6108(2) 0.0227(11) Uani 1 1 d . . . C57 C 0.8628(4) 0.9737(3) -0.5454(2) 0.0255(11) Uani 1 1 d . . . C58 C 0.7608(5) 0.9910(3) -0.5536(3) 0.0388(14) Uani 1 1 d . . . H58 H 0.7553 0.9945 -0.6010 0.047 Uiso 1 1 calc R . . C59 C 0.6672(5) 1.0032(4) -0.4943(3) 0.0495(16) Uani 1 1 d . . . H59 H 0.5980 1.0166 -0.5010 0.059 Uiso 1 1 calc R . . C60 C 0.6753(5) 0.9958(4) -0.4252(4) 0.0550(19) Uani 1 1 d . . . H60 H 0.6118 1.0020 -0.3843 0.066 Uiso 1 1 calc R . . C61 C 0.7746(5) 0.9795(3) -0.4156(3) 0.0449(16) Uani 1 1 d . . . H61 H 0.7793 0.9758 -0.3680 0.054 Uiso 1 1 calc R . . C62 C 0.8688(4) 0.9684(3) -0.4752(2) 0.0294(12) Uani 1 1 d . . . H62 H 0.9372 0.9572 -0.4681 0.035 Uiso 1 1 calc R . . C63 C 1.1501(4) 0.8393(3) -0.5290(2) 0.0167(10) Uani 1 1 d . . . H63 H 1.2002 0.8664 -0.5445 0.020 Uiso 1 1 calc R . . C64 C 1.2227(4) 0.7749(3) -0.4349(2) 0.0157(9) Uani 1 1 d . . . C65 C 1.3218(4) 0.7892(3) -0.4616(2) 0.0222(10) Uani 1 1 d . . . H65 H 1.3386 0.8144 -0.5067 0.027 Uiso 1 1 calc R . . C66 C 1.3941(4) 0.7670(3) -0.4230(2) 0.0262(11) Uani 1 1 d . . . H66 H 1.4603 0.7774 -0.4417 0.031 Uiso 1 1 calc R . . C67 C 1.3726(4) 0.7301(3) -0.3575(2) 0.0268(11) Uani 1 1 d . . . H67 H 1.4235 0.7146 -0.3314 0.032 Uiso 1 1 calc R . . C68 C 1.2764(4) 0.7160(3) -0.3308(2) 0.0226(10) Uani 1 1 d . . . H68 H 1.2621 0.6896 -0.2862 0.027 Uiso 1 1 calc R . . C69 C 1.1987(4) 0.7392(3) -0.3669(2) 0.0162(9) Uani 1 1 d . . . C70 C 1.0915(4) 0.7285(3) -0.33357(19) 0.0151(9) Uani 1 1 d . . . C71 C 1.0873(4) 0.6551(3) -0.3065(2) 0.0198(10) Uani 1 1 d . . . H71 H 1.1534 0.6106 -0.3121 0.024 Uiso 1 1 calc R . . C72 C 0.9867(4) 0.6472(3) -0.2713(2) 0.0263(12) Uani 1 1 d . . . H72 H 0.9845 0.5970 -0.2533 0.032 Uiso 1 1 calc R . . C73 C 0.8906(4) 0.7111(3) -0.2623(2) 0.0265(12) Uani 1 1 d . . . H73 H 0.8223 0.7051 -0.2379 0.032 Uiso 1 1 calc R . . C74 C 0.8929(4) 0.7850(3) -0.2888(2) 0.0246(11) Uani 1 1 d . . . H74 H 0.8266 0.8294 -0.2828 0.029 Uiso 1 1 calc R . . C75 C 0.9928(4) 0.7927(3) -0.3239(2) 0.0203(10) Uani 1 1 d . . . H75 H 0.9944 0.8430 -0.3420 0.024 Uiso 1 1 calc R . . C76 C 1.2179(4) 0.6459(3) -0.6138(2) 0.0182(10) Uani 1 1 d . . . C77 C 1.2078(4) 0.6935(3) -0.6741(2) 0.0249(11) Uani 1 1 d . . . H77 H 1.1399 0.7349 -0.6719 0.030 Uiso 1 1 calc R . . C78 C 1.2967(5) 0.6802(3) -0.7369(3) 0.0382(14) Uani 1 1 d . . . H78 H 1.2896 0.7128 -0.7775 0.046 Uiso 1 1 calc R . . C79 C 1.3957(5) 0.6199(4) -0.7411(3) 0.0441(15) Uani 1 1 d . . . H79 H 1.4561 0.6106 -0.7846 0.053 Uiso 1 1 calc R . . C80 C 1.4062(4) 0.5729(3) -0.6814(2) 0.0350(13) Uani 1 1 d . . . H80 H 1.4742 0.5312 -0.6847 0.042 Uiso 1 1 calc R . . C81 C 1.3190(4) 0.5857(3) -0.6168(2) 0.0228(11) Uani 1 1 d . . . C82 C 1.3382(4) 0.5372(3) -0.5533(2) 0.0208(10) Uani 1 1 d . . . C83 C 1.3648(4) 0.4555(3) -0.5541(2) 0.0270(11) Uani 1 1 d . . . H83 H 1.3687 0.4299 -0.5954 0.032 Uiso 1 1 calc R . . C84 C 1.3861(4) 0.4107(3) -0.4953(3) 0.0309(12) Uani 1 1 d . . . H84 H 1.4027 0.3550 -0.4961 0.037 Uiso 1 1 calc R . . C85 C 1.3831(4) 0.4472(3) -0.4353(2) 0.0300(12) Uani 1 1 d . . . H85 H 1.3987 0.4164 -0.3954 0.036 Uiso 1 1 calc R . . C86 C 1.3572(4) 0.5283(3) -0.4339(2) 0.0298(12) Uani 1 1 d . . . H86 H 1.3554 0.5535 -0.3930 0.036 Uiso 1 1 calc R . . C87 C 1.3339(4) 0.5733(3) -0.4924(2) 0.0260(11) Uani 1 1 d . . . H87 H 1.3149 0.6292 -0.4907 0.031 Uiso 1 1 calc R . . C88 C 1.0959(3) 0.5998(3) -0.5152(2) 0.0144(9) Uani 1 1 d . . . H88 H 1.1371 0.5461 -0.5316 0.017 Uiso 1 1 calc R . . C89 C 0.9837(4) 0.5572(3) -0.4137(2) 0.0173(10) Uani 1 1 d . . . C90 C 1.0664(4) 0.4868(3) -0.4053(2) 0.0203(10) Uani 1 1 d . . . H90 H 1.1410 0.4796 -0.4303 0.024 Uiso 1 1 calc R . . C91 C 1.0417(4) 0.4276(3) -0.3616(2) 0.0261(11) Uani 1 1 d . . . H91 H 1.0992 0.3799 -0.3576 0.031 Uiso 1 1 calc R . . C92 C 0.9345(4) 0.4371(3) -0.3237(2) 0.0242(11) Uani 1 1 d . . . H92 H 0.9176 0.3963 -0.2936 0.029 Uiso 1 1 calc R . . C93 C 0.8519(4) 0.5067(3) -0.3301(2) 0.0234(11) Uani 1 1 d . . . H93 H 0.7780 0.5131 -0.3038 0.028 Uiso 1 1 calc R . . C94 C 0.8736(4) 0.5681(3) -0.3739(2) 0.0183(10) Uani 1 1 d . . . C95 C 0.7816(4) 0.6431(3) -0.3756(2) 0.0198(10) Uani 1 1 d . . . C96 C 0.6946(4) 0.6746(3) -0.3111(2) 0.0226(11) Uani 1 1 d . . . H96 H 0.6938 0.6460 -0.2676 0.027 Uiso 1 1 calc R . . C97 C 0.6104(4) 0.7467(3) -0.3101(2) 0.0271(12) Uani 1 1 d . . . H97 H 0.5527 0.7673 -0.2661 0.033 Uiso 1 1 calc R . . C98 C 0.6104(4) 0.7889(3) -0.3736(2) 0.0280(11) Uani 1 1 d . . . H98 H 0.5539 0.8390 -0.3727 0.034 Uiso 1 1 calc R . . C99 C 0.6921(4) 0.7581(3) -0.4373(2) 0.0246(11) Uani 1 1 d . . . H99 H 0.6912 0.7866 -0.4808 0.030 Uiso 1 1 calc R . . C100 C 0.7763(4) 0.6854(3) -0.4388(2) 0.0207(10) Uani 1 1 d . . . H100 H 0.8312 0.6641 -0.4837 0.025 Uiso 1 1 calc R . . 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 0.02031(10) 0.01312(9) 0.01366(8) 0.00204(6) -0.00593(7) -0.00508(8) Bi2 0.01795(9) 0.01197(9) 0.01305(8) 0.00155(6) -0.00491(7) -0.00568(7) Br1 0.0235(3) 0.0208(3) 0.0249(2) 0.00421(18) -0.00485(19) -0.0096(2) Br2 0.0276(3) 0.0199(3) 0.0197(2) 0.00443(17) -0.01295(19) -0.0094(2) O1 0.138(6) 0.090(5) 0.112(4) 0.045(4) -0.078(4) -0.079(4) N1 0.022(2) 0.017(2) 0.0151(17) -0.0008(14) -0.0024(16) -0.0095(18) N2 0.017(2) 0.015(2) 0.0196(18) 0.0010(15) -0.0055(15) -0.0053(17) N3 0.023(2) 0.0101(19) 0.0155(17) 0.0058(14) -0.0116(15) -0.0071(17) N4 0.023(2) 0.017(2) 0.0150(18) 0.0015(14) -0.0088(16) -0.0082(18) N5 0.026(2) 0.014(2) 0.0177(18) 0.0062(14) -0.0085(16) -0.0120(18) N6 0.023(2) 0.017(2) 0.0149(17) 0.0031(15) -0.0070(16) -0.0099(18) N7 0.020(2) 0.016(2) 0.0102(17) 0.0006(14) -0.0029(15) -0.0060(17) N8 0.019(2) 0.014(2) 0.0163(18) 0.0022(14) -0.0051(15) -0.0071(17) C1 0.021(3) 0.021(3) 0.023(2) -0.0030(19) -0.004(2) -0.011(2) C1S 0.117(8) 0.072(6) 0.100(6) 0.011(5) -0.055(6) -0.059(6) C2 0.035(3) 0.030(3) 0.023(2) -0.005(2) -0.002(2) -0.016(3) C2S 0.175(11) 0.172(11) 0.096(6) 0.023(7) -0.062(7) -0.133(10) C3 0.041(3) 0.037(3) 0.030(3) -0.011(2) -0.008(2) -0.020(3) C3S 0.33(2) 0.184(13) 0.156(10) 0.124(10) -0.186(12) -0.186(15) C4 0.041(3) 0.024(3) 0.043(3) -0.009(2) -0.009(3) -0.014(3) C4S 0.307(17) 0.153(11) 0.127(8) 0.100(8) -0.145(10) -0.180(13) C5 0.039(3) 0.019(3) 0.035(3) 0.004(2) -0.011(2) -0.013(3) C6 0.022(3) 0.014(3) 0.026(2) -0.0012(18) -0.002(2) -0.005(2) C7 0.026(3) 0.011(2) 0.023(2) 0.0029(18) -0.005(2) -0.004(2) C8 0.026(3) 0.017(3) 0.034(3) 0.008(2) -0.010(2) -0.003(2) C9 0.039(3) 0.029(3) 0.044(3) 0.012(2) -0.028(3) -0.012(3) C10 0.048(4) 0.047(4) 0.032(3) 0.015(3) -0.022(3) -0.018(3) C11 0.039(3) 0.040(3) 0.024(3) 0.014(2) -0.010(2) -0.014(3) C12 0.026(3) 0.027(3) 0.031(3) 0.009(2) -0.011(2) -0.011(2) C13 0.020(3) 0.016(2) 0.016(2) 0.0006(17) -0.0037(18) -0.003(2) C14 0.017(2) 0.012(2) 0.017(2) 0.0013(17) -0.0051(18) -0.0038(19) C15 0.023(3) 0.019(3) 0.021(2) -0.0054(18) -0.0065(19) -0.008(2) C16 0.023(3) 0.022(3) 0.016(2) 0.0011(18) -0.0036(19) -0.008(2) C17 0.022(3) 0.020(3) 0.026(2) 0.0027(19) -0.002(2) -0.009(2) C18 0.016(2) 0.020(3) 0.026(2) -0.0003(19) -0.0095(19) -0.007(2) C19 0.013(2) 0.016(2) 0.019(2) 0.0005(17) -0.0073(18) 0.000(2) C20 0.020(3) 0.024(3) 0.018(2) 0.0049(18) -0.0100(19) -0.012(2) C21 0.053(4) 0.031(3) 0.028(3) 0.010(2) -0.024(3) -0.020(3) C22 0.080(5) 0.047(4) 0.040(3) 0.025(3) -0.036(3) -0.029(4) C23 0.058(4) 0.068(5) 0.017(3) 0.006(3) -0.013(3) -0.029(4) C24 0.035(3) 0.045(4) 0.023(3) -0.007(2) -0.005(2) -0.016(3) C25 0.021(3) 0.028(3) 0.023(2) 0.0012(19) -0.009(2) -0.010(2) C26 0.014(2) 0.019(3) 0.014(2) 0.0003(17) -0.0030(17) -0.002(2) C27 0.024(3) 0.020(3) 0.019(2) 0.0055(18) -0.0084(19) -0.011(2) C28 0.031(3) 0.024(3) 0.022(2) -0.0034(19) -0.008(2) -0.014(2) C29 0.022(3) 0.028(3) 0.021(2) 0.0010(19) -0.010(2) -0.007(2) C30 0.014(2) 0.018(3) 0.024(2) 0.0044(18) -0.0094(19) 0.001(2) C31 0.008(2) 0.019(2) 0.018(2) -0.0020(17) -0.0040(17) -0.0022(19) C32 0.013(2) 0.017(2) 0.015(2) 0.0051(17) -0.0050(18) -0.005(2) C33 0.024(3) 0.024(3) 0.032(3) 0.008(2) -0.016(2) -0.007(2) C34 0.027(3) 0.019(3) 0.041(3) 0.006(2) -0.017(2) -0.006(2) C35 0.034(3) 0.022(3) 0.032(3) 0.005(2) -0.015(2) -0.016(3) C36 0.022(3) 0.026(3) 0.023(2) 0.0045(19) -0.013(2) -0.011(2) C37 0.017(2) 0.017(2) 0.015(2) 0.0046(17) -0.0064(18) -0.003(2) C38 0.012(2) 0.011(2) 0.021(2) 0.0040(17) -0.0038(18) -0.0054(19) C39 0.011(2) 0.017(2) 0.023(2) 0.0002(18) -0.0049(18) -0.004(2) C40 0.019(2) 0.017(3) 0.027(2) -0.0020(18) -0.0052(19) -0.007(2) C41 0.022(3) 0.021(3) 0.037(3) -0.003(2) -0.003(2) -0.009(2) C42 0.018(3) 0.029(3) 0.044(3) -0.021(2) -0.004(2) -0.008(2) C43 0.019(3) 0.033(3) 0.028(2) -0.010(2) -0.003(2) -0.009(2) C44 0.013(2) 0.019(3) 0.021(2) -0.0061(18) -0.0053(18) -0.004(2) C45 0.020(3) 0.023(3) 0.015(2) -0.0040(18) -0.0016(19) -0.002(2) C46 0.042(4) 0.045(4) 0.026(3) 0.002(2) -0.015(2) -0.015(3) C47 0.067(5) 0.050(4) 0.029(3) 0.017(3) -0.024(3) -0.016(4) C48 0.062(4) 0.027(3) 0.028(3) 0.011(2) -0.007(3) -0.014(3) C49 0.038(3) 0.025(3) 0.025(3) -0.001(2) -0.001(2) -0.012(3) C50 0.032(3) 0.018(3) 0.019(2) -0.0011(18) -0.009(2) -0.008(2) C51 0.034(3) 0.018(3) 0.021(2) 0.0051(18) -0.010(2) -0.016(2) C52 0.032(3) 0.026(3) 0.026(2) 0.006(2) -0.011(2) -0.016(2) C53 0.059(4) 0.031(3) 0.019(2) 0.012(2) -0.014(2) -0.025(3) C54 0.063(4) 0.027(3) 0.025(3) 0.013(2) -0.021(3) -0.017(3) C55 0.047(4) 0.015(3) 0.034(3) 0.006(2) -0.023(3) -0.007(3) C56 0.032(3) 0.017(3) 0.022(2) 0.0023(18) -0.012(2) -0.011(2) C57 0.034(3) 0.011(2) 0.030(3) -0.0017(19) -0.010(2) -0.006(2) C58 0.039(4) 0.024(3) 0.048(3) -0.007(2) -0.017(3) -0.001(3) C59 0.032(4) 0.037(4) 0.070(4) -0.015(3) -0.013(3) -0.001(3) C60 0.038(4) 0.032(4) 0.072(5) -0.022(3) 0.015(3) -0.011(3) C61 0.063(5) 0.027(3) 0.035(3) -0.009(2) 0.003(3) -0.021(3) C62 0.039(3) 0.019(3) 0.030(3) -0.004(2) -0.004(2) -0.015(3) C63 0.019(2) 0.015(2) 0.018(2) -0.0012(17) -0.0032(18) -0.010(2) C64 0.017(2) 0.012(2) 0.017(2) -0.0029(17) -0.0050(18) -0.004(2) C65 0.019(3) 0.025(3) 0.024(2) -0.0013(19) -0.005(2) -0.010(2) C66 0.017(3) 0.032(3) 0.029(3) -0.008(2) -0.004(2) -0.009(2) C67 0.024(3) 0.030(3) 0.031(3) -0.008(2) -0.016(2) -0.007(2) C68 0.022(3) 0.021(3) 0.021(2) -0.0009(19) -0.009(2) -0.002(2) C69 0.018(2) 0.010(2) 0.019(2) -0.0029(17) -0.0073(18) -0.0004(19) C70 0.018(2) 0.018(2) 0.0096(19) -0.0026(16) -0.0068(17) -0.005(2) C71 0.026(3) 0.017(3) 0.017(2) -0.0032(17) -0.0064(19) -0.007(2) C72 0.037(3) 0.029(3) 0.018(2) 0.0034(19) -0.006(2) -0.021(3) C73 0.024(3) 0.046(3) 0.012(2) -0.002(2) -0.0032(19) -0.017(3) C74 0.022(3) 0.030(3) 0.021(2) 0.004(2) -0.010(2) -0.007(2) C75 0.027(3) 0.021(3) 0.013(2) -0.0005(17) -0.0051(19) -0.010(2) C76 0.019(3) 0.020(3) 0.015(2) -0.0030(17) -0.0019(18) -0.010(2) C77 0.030(3) 0.017(3) 0.022(2) 0.0015(19) -0.002(2) -0.009(2) C78 0.043(4) 0.034(3) 0.027(3) 0.008(2) 0.001(2) -0.014(3) C79 0.033(3) 0.044(4) 0.031(3) 0.005(3) 0.011(2) -0.008(3) C80 0.022(3) 0.039(3) 0.033(3) 0.001(2) 0.004(2) -0.010(3) C81 0.021(3) 0.021(3) 0.026(2) -0.0002(19) -0.004(2) -0.010(2) C82 0.010(2) 0.022(3) 0.026(2) -0.0012(19) -0.0025(19) -0.004(2) C83 0.026(3) 0.022(3) 0.032(3) -0.008(2) -0.009(2) -0.005(2) C84 0.032(3) 0.018(3) 0.037(3) 0.001(2) -0.007(2) -0.006(2) C85 0.027(3) 0.022(3) 0.027(3) 0.000(2) -0.006(2) 0.004(2) C86 0.029(3) 0.026(3) 0.027(3) -0.008(2) -0.007(2) -0.001(2) C87 0.025(3) 0.018(3) 0.030(3) -0.003(2) -0.003(2) -0.006(2) C88 0.016(2) 0.013(2) 0.014(2) 0.0005(16) -0.0059(18) -0.0044(19) C89 0.025(3) 0.017(2) 0.011(2) -0.0025(17) -0.0007(18) -0.012(2) C90 0.022(3) 0.017(3) 0.019(2) -0.0007(18) -0.0037(19) -0.007(2) C91 0.040(3) 0.016(3) 0.024(2) -0.0003(19) -0.014(2) -0.008(2) C92 0.040(3) 0.022(3) 0.019(2) 0.0069(19) -0.011(2) -0.020(3) C93 0.034(3) 0.028(3) 0.014(2) -0.0014(19) -0.005(2) -0.018(3) C94 0.024(3) 0.023(3) 0.012(2) -0.0034(17) -0.0067(18) -0.012(2) C95 0.024(3) 0.024(3) 0.019(2) -0.0033(18) -0.0061(19) -0.017(2) C96 0.025(3) 0.037(3) 0.016(2) -0.0026(19) -0.0063(19) -0.021(3) C97 0.015(3) 0.037(3) 0.029(3) -0.011(2) -0.007(2) -0.006(2) C98 0.021(3) 0.028(3) 0.034(3) -0.007(2) -0.012(2) -0.003(2) C99 0.022(3) 0.030(3) 0.024(2) 0.000(2) -0.010(2) -0.009(2) C100 0.023(3) 0.024(3) 0.018(2) -0.0026(18) -0.0056(19) -0.012(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Bi1 N3 2.266(3) . ? Bi1 N1 2.341(3) . ? Bi1 N2 2.473(3) . ? Bi1 N4 2.614(4) . ? Bi1 Br1 2.6908(5) . ? Bi1 C13 2.836(4) . ? Bi1 C38 2.851(4) . ? Bi2 N7 2.218(4) . ? Bi2 N5 2.288(3) . ? Bi2 N6 2.539(4) . ? Bi2 N8 2.663(3) . ? Bi2 Br2 2.7140(5) . ? Bi2 C63 2.839(4) . ? Bi2 C88 2.848(4) . ? O1 C3S 1.353(9) . ? O1 C1S 1.355(9) . ? N1 C13 1.334(5) . ? N1 C1 1.405(5) . ? N2 C13 1.304(5) . ? N2 C14 1.393(5) . ? N3 C38 1.340(5) . ? N3 C26 1.419(5) . ? N4 C38 1.295(5) . ? N4 C39 1.399(5) . ? N5 C63 1.312(5) . ? N5 C51 1.424(5) . ? N6 C63 1.312(5) . ? N6 C64 1.401(5) . ? N7 C88 1.346(5) . ? N7 C76 1.418(5) . ? N8 C88 1.302(5) . ? N8 C89 1.405(5) . ? C1 C2 1.397(6) . ? C1 C6 1.401(6) . ? C1S C2S 1.424(10) . ? C2 C3 1.386(6) . ? C3 C4 1.368(7) . ? C3S C4S 1.350(11) . ? C4 C5 1.380(7) . ? C5 C6 1.405(6) . ? C6 C7 1.482(6) . ? C7 C12 1.389(6) . ? C7 C8 1.397(6) . ? C8 C9 1.401(6) . ? C9 C10 1.377(7) . ? C10 C11 1.365(7) . ? C11 C12 1.380(6) . ? C14 C19 1.406(6) . ? C14 C15 1.409(5) . ? C15 C16 1.383(6) . ? C16 C17 1.372(6) . ? C17 C18 1.375(6) . ? C18 C19 1.393(6) . ? C19 C20 1.493(6) . ? C20 C21 1.386(7) . ? C20 C25 1.384(6) . ? C21 C22 1.377(7) . ? C22 C23 1.392(8) . ? C23 C24 1.381(8) . ? C24 C25 1.391(6) . ? C26 C27 1.385(6) . ? C26 C31 1.422(6) . ? C27 C28 1.388(6) . ? C28 C29 1.389(6) . ? C29 C30 1.377(6) . ? C30 C31 1.405(6) . ? C31 C32 1.487(6) . ? C32 C33 1.397(6) . ? C32 C37 1.399(6) . ? C33 C34 1.380(6) . ? C34 C35 1.378(7) . ? C35 C36 1.387(7) . ? C36 C37 1.381(6) . ? C39 C40 1.398(6) . ? C39 C44 1.404(6) . ? C40 C41 1.378(6) . ? C41 C42 1.388(7) . ? C42 C43 1.375(7) . ? C43 C44 1.396(6) . ? C44 C45 1.491(6) . ? C45 C50 1.384(6) . ? C45 C46 1.408(7) . ? C46 C47 1.383(7) . ? C47 C48 1.370(8) . ? C48 C49 1.390(7) . ? C49 C50 1.389(6) . ? C51 C56 1.392(7) . ? C51 C52 1.399(6) . ? C52 C53 1.392(6) . ? C53 C54 1.366(8) . ? C54 C55 1.380(7) . ? C55 C56 1.414(6) . ? C56 C57 1.491(6) . ? C57 C58 1.390(7) . ? C57 C62 1.396(6) . ? C58 C59 1.384(8) . ? C59 C60 1.383(8) . ? C60 C61 1.370(9) . ? C61 C62 1.394(7) . ? C64 C69 1.412(6) . ? C64 C65 1.412(6) . ? C65 C66 1.371(6) . ? C66 C67 1.379(6) . ? C67 C68 1.372(6) . ? C68 C69 1.394(6) . ? C69 C70 1.490(6) . ? C70 C75 1.394(6) . ? C70 C71 1.397(6) . ? C71 C72 1.391(6) . ? C72 C73 1.371(7) . ? C73 C74 1.396(7) . ? C74 C75 1.380(6) . ? C76 C77 1.403(6) . ? C76 C81 1.405(7) . ? C77 C78 1.385(6) . ? C78 C79 1.380(8) . ? C79 C80 1.390(7) . ? C80 C81 1.395(6) . ? C81 C82 1.487(6) . ? C82 C83 1.386(6) . ? C82 C87 1.393(6) . ? C83 C84 1.389(7) . ? C84 C85 1.387(7) . ? C85 C86 1.380(7) . ? C86 C87 1.392(7) . ? C89 C90 1.400(6) . ? C89 C94 1.411(6) . ? C90 C91 1.376(6) . ? C91 C92 1.375(7) . ? C92 C93 1.379(7) . ? C93 C94 1.397(6) . ? C94 C95 1.483(7) . ? C95 C100 1.397(6) . ? C95 C96 1.412(6) . ? C96 C97 1.386(7) . ? C97 C98 1.392(7) . ? C98 C99 1.371(6) . ? C99 C100 1.392(7) . ? 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 N3 Bi1 N1 94.90(12) . . ? N3 Bi1 N2 80.33(12) . . ? N1 Bi1 N2 55.15(11) . . ? N3 Bi1 N4 54.40(11) . . ? N1 Bi1 N4 148.83(11) . . ? N2 Bi1 N4 108.21(11) . . ? N3 Bi1 Br1 86.55(9) . . ? N1 Bi1 Br1 86.72(9) . . ? N2 Bi1 Br1 137.86(8) . . ? N4 Bi1 Br1 95.61(8) . . ? N3 Bi1 C13 87.36(12) . . ? N1 Bi1 C13 27.81(11) . . ? N2 Bi1 C13 27.34(11) . . ? N4 Bi1 C13 131.09(11) . . ? Br1 Bi1 C13 112.96(9) . . ? N3 Bi1 C38 27.43(11) . . ? N1 Bi1 C38 122.22(12) . . ? N2 Bi1 C38 95.13(11) . . ? N4 Bi1 C38 26.97(10) . . ? Br1 Bi1 C38 90.84(8) . . ? C13 Bi1 C38 110.52(12) . . ? N7 Bi2 N5 91.43(12) . . ? N7 Bi2 N6 82.24(12) . . ? N5 Bi2 N6 54.53(12) . . ? N7 Bi2 N8 54.42(11) . . ? N5 Bi2 N8 145.04(12) . . ? N6 Bi2 N8 107.47(11) . . ? N7 Bi2 Br2 87.41(9) . . ? N5 Bi2 Br2 85.98(9) . . ? N6 Bi2 Br2 138.60(7) . . ? N8 Bi2 Br2 98.32(7) . . ? N7 Bi2 C63 86.75(12) . . ? N5 Bi2 C63 27.01(12) . . ? N6 Bi2 C63 27.53(11) . . ? N8 Bi2 C63 129.40(12) . . ? Br2 Bi2 C63 112.31(8) . . ? N7 Bi2 C88 27.39(11) . . ? N5 Bi2 C88 118.67(12) . . ? N6 Bi2 C88 96.35(12) . . ? N8 Bi2 C88 27.06(10) . . ? Br2 Bi2 C88 92.19(8) . . ? C63 Bi2 C88 109.74(12) . . ? C3S O1 C1S 113.0(7) . . ? C13 N1 C1 122.2(3) . . ? C13 N1 Bi1 97.2(3) . . ? C1 N1 Bi1 140.3(3) . . ? C13 N2 C14 124.4(3) . . ? C13 N2 Bi1 92.0(2) . . ? C14 N2 Bi1 142.3(3) . . ? C38 N3 C26 123.1(4) . . ? C38 N3 Bi1 101.4(3) . . ? C26 N3 Bi1 135.4(3) . . ? C38 N4 C39 120.8(4) . . ? C38 N4 Bi1 86.7(2) . . ? C39 N4 Bi1 151.0(3) . . ? C63 N5 C51 122.3(3) . . ? C63 N5 Bi2 100.6(3) . . ? C51 N5 Bi2 136.9(3) . . ? C63 N6 C64 123.0(4) . . ? C63 N6 Bi2 89.1(3) . . ? C64 N6 Bi2 147.9(3) . . ? C88 N7 C76 122.0(4) . . ? C88 N7 Bi2 103.3(3) . . ? C76 N7 Bi2 134.7(3) . . ? C88 N8 C89 119.9(4) . . ? C88 N8 Bi2 84.4(2) . . ? C89 N8 Bi2 155.6(3) . . ? C2 C1 C6 120.1(4) . . ? C2 C1 N1 119.7(4) . . ? C6 C1 N1 120.2(4) . . ? O1 C1S C2S 111.7(7) . . ? C3 C2 C1 120.8(5) . . ? C4 C3 C2 119.6(5) . . ? C4S C3S O1 116.5(9) . . ? C3 C4 C5 120.4(5) . . ? C4 C5 C6 121.7(4) . . ? C1 C6 C5 117.5(4) . . ? C1 C6 C7 122.6(4) . . ? C5 C6 C7 119.9(4) . . ? C12 C7 C8 118.0(4) . . ? C12 C7 C6 120.0(4) . . ? C8 C7 C6 122.1(4) . . ? C7 C8 C9 120.6(4) . . ? C10 C9 C8 119.4(5) . . ? C11 C10 C9 120.4(5) . . ? C10 C11 C12 120.4(4) . . ? C11 C12 C7 121.1(5) . . ? N2 C13 N1 115.6(4) . . ? N2 C13 Bi1 60.6(2) . . ? N1 C13 Bi1 55.0(2) . . ? N2 C14 C19 119.2(3) . . ? N2 C14 C15 121.2(4) . . ? C19 C14 C15 119.3(4) . . ? C16 C15 C14 120.0(4) . . ? C17 C16 C15 120.7(4) . . ? C16 C17 C18 119.7(4) . . ? C17 C18 C19 121.8(4) . . ? C18 C19 C14 118.5(4) . . ? C18 C19 C20 120.4(4) . . ? C14 C19 C20 121.1(4) . . ? C21 C20 C25 118.9(4) . . ? C21 C20 C19 121.1(4) . . ? C25 C20 C19 120.0(4) . . ? C22 C21 C20 120.4(5) . . ? C21 C22 C23 120.9(5) . . ? C24 C23 C22 118.8(5) . . ? C23 C24 C25 120.3(5) . . ? C20 C25 C24 120.6(5) . . ? C27 C26 N3 118.3(4) . . ? C27 C26 C31 119.6(4) . . ? N3 C26 C31 122.1(4) . . ? C26 C27 C28 121.6(4) . . ? C27 C28 C29 119.3(4) . . ? C30 C29 C28 119.9(4) . . ? C29 C30 C31 122.0(4) . . ? C30 C31 C26 117.5(4) . . ? C30 C31 C32 117.4(4) . . ? C26 C31 C32 125.1(4) . . ? C33 C32 C37 117.4(4) . . ? C33 C32 C31 121.3(4) . . ? C37 C32 C31 121.1(4) . . ? C34 C33 C32 121.3(5) . . ? C35 C34 C33 120.1(5) . . ? C34 C35 C36 120.0(4) . . ? C37 C36 C35 119.6(5) . . ? C36 C37 C32 121.5(4) . . ? N4 C38 N3 117.5(4) . . ? N4 C38 Bi1 66.3(2) . . ? N3 C38 Bi1 51.2(2) . . ? N4 C39 C40 121.1(4) . . ? N4 C39 C44 119.8(4) . . ? C40 C39 C44 119.0(4) . . ? C41 C40 C39 121.4(4) . . ? C40 C41 C42 119.7(4) . . ? C43 C42 C41 119.4(4) . . ? C42 C43 C44 122.0(4) . . ? C43 C44 C39 118.4(4) . . ? C43 C44 C45 119.2(4) . . ? C39 C44 C45 122.4(4) . . ? C50 C45 C46 118.5(4) . . ? C50 C45 C44 121.7(4) . . ? C46 C45 C44 119.7(4) . . ? C47 C46 C45 119.5(5) . . ? C48 C47 C46 121.4(5) . . ? C47 C48 C49 119.8(5) . . ? C50 C49 C48 119.3(5) . . ? C45 C50 C49 121.4(5) . . ? C56 C51 C52 121.4(4) . . ? C56 C51 N5 119.9(4) . . ? C52 C51 N5 118.7(5) . . ? C53 C52 C51 119.4(5) . . ? C54 C53 C52 120.2(5) . . ? C53 C54 C55 120.6(5) . . ? C54 C55 C56 121.1(5) . . ? C51 C56 C55 117.2(4) . . ? C51 C56 C57 123.9(4) . . ? C55 C56 C57 118.8(5) . . ? C58 C57 C62 118.1(5) . . ? C58 C57 C56 119.8(4) . . ? C62 C57 C56 122.1(5) . . ? C59 C58 C57 121.5(5) . . ? C60 C59 C58 119.5(6) . . ? C61 C60 C59 120.1(5) . . ? C60 C61 C62 120.5(6) . . ? C61 C62 C57 120.2(5) . . ? N6 C63 N5 115.8(4) . . ? N6 C63 Bi2 63.4(2) . . ? N5 C63 Bi2 52.4(2) . . ? N6 C64 C69 118.5(4) . . ? N6 C64 C65 123.0(4) . . ? C69 C64 C65 118.4(4) . . ? C66 C65 C64 120.6(4) . . ? C65 C66 C67 121.2(4) . . ? C68 C67 C66 118.8(4) . . ? C67 C68 C69 122.3(4) . . ? C68 C69 C64 118.6(4) . . ? C68 C69 C70 120.7(4) . . ? C64 C69 C70 120.7(4) . . ? C75 C70 C71 118.3(4) . . ? C75 C70 C69 120.9(4) . . ? C71 C70 C69 120.7(4) . . ? C72 C71 C70 120.2(5) . . ? C73 C72 C71 120.6(4) . . ? C72 C73 C74 120.1(4) . . ? C75 C74 C73 119.2(5) . . ? C74 C75 C70 121.6(4) . . ? C77 C76 C81 119.9(4) . . ? C77 C76 N7 118.1(4) . . ? C81 C76 N7 122.0(4) . . ? C78 C77 C76 120.1(5) . . ? C79 C78 C77 120.6(5) . . ? C78 C79 C80 119.6(5) . . ? C79 C80 C81 121.4(5) . . ? C80 C81 C76 118.5(4) . . ? C80 C81 C82 118.6(5) . . ? C76 C81 C82 122.9(4) . . ? C83 C82 C87 118.5(4) . . ? C83 C82 C81 121.6(4) . . ? C87 C82 C81 119.8(4) . . ? C82 C83 C84 120.9(4) . . ? C85 C84 C83 120.1(5) . . ? C86 C85 C84 119.7(5) . . ? C85 C86 C87 120.1(4) . . ? C86 C87 C82 120.7(5) . . ? N8 C88 N7 117.7(4) . . ? N8 C88 Bi2 68.5(2) . . ? N7 C88 Bi2 49.3(2) . . ? C90 C89 N8 120.5(4) . . ? C90 C89 C94 118.6(4) . . ? N8 C89 C94 120.9(4) . . ? C91 C90 C89 121.3(4) . . ? C90 C91 C92 120.5(5) . . ? C91 C92 C93 119.1(4) . . ? C92 C93 C94 122.1(4) . . ? C93 C94 C89 118.4(5) . . ? C93 C94 C95 119.5(4) . . ? C89 C94 C95 122.1(4) . . ? C100 C95 C96 117.3(5) . . ? C100 C95 C94 123.0(4) . . ? C96 C95 C94 119.7(4) . . ? C97 C96 C95 121.1(4) . . ? C96 C97 C98 119.9(4) . . ? C99 C98 C97 120.0(5) . . ? C98 C99 C100 120.4(4) . . ? C99 C100 C95 121.2(4) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.226 _refine_diff_density_min -2.319 _refine_diff_density_rms 0.151 # Attachment '3b.CIF' data_3b _database_code_depnum_ccdc_archive 'CCDC 643179' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C63 H81 Bi N6), C4 H10 O' _chemical_formula_sum 'C130 H172 Bi2 N12 O' _chemical_formula_weight 2336.76 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_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' _cell_length_a 14.505(3) _cell_length_b 38.248(8) _cell_length_c 22.094(4) _cell_angle_alpha 90.00 _cell_angle_beta 108.64(3) _cell_angle_gamma 90.00 _cell_volume 11615(4) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4840 _exptl_absorpt_coefficient_mu 3.081 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5777 _exptl_absorpt_correction_T_max 0.6384 _exptl_absorpt_process_details 'performed as part of the DENZO-SMN package' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius KAPPA CCD' _diffrn_measurement_method '1.0 deg frames in phi and omega' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30693 _diffrn_reflns_av_R_equivalents 0.0562 _diffrn_reflns_av_sigmaI/netI 0.0991 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -45 _diffrn_reflns_limit_k_max 45 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.11 _diffrn_reflns_theta_max 25.00 _reflns_number_total 16513 _reflns_number_gt 11759 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed / POV-Ray' _computing_publication_material 'Microsoft Office 2000' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0284P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 16513 _refine_ls_number_parameters 1332 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0839 _refine_ls_R_factor_gt 0.0473 _refine_ls_wR_factor_ref 0.0873 _refine_ls_wR_factor_gt 0.0780 _refine_ls_goodness_of_fit_ref 0.995 _refine_ls_restrained_S_all 0.995 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 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 _atom_site_disorder_assembly _atom_site_disorder_group Bi1 Bi 0.320181(16) 0.051207(7) 0.266125(11) 0.01588(7) Uani 1 1 d . . . Bi2 Bi 0.660152(16) -0.225350(7) 0.208983(11) 0.01576(7) Uani 1 1 d . . . O1 O 0.7382(3) -0.38230(15) -0.0132(2) 0.0422(14) Uani 1 1 d . . . N1 N 0.2821(3) 0.00194(13) 0.2055(2) 0.0162(12) Uani 1 1 d . . . N2 N 0.4431(3) -0.00334(13) 0.2625(2) 0.0153(12) Uani 1 1 d . . . N3 N 0.3905(3) 0.07870(14) 0.2019(2) 0.0178(13) Uani 1 1 d . . . N4 N 0.3904(3) 0.11854(14) 0.2783(2) 0.0171(13) Uani 1 1 d . . . N5 N 0.1733(3) 0.07705(14) 0.2243(2) 0.0157(12) Uani 1 1 d . . . N6 N 0.1472(3) 0.03671(14) 0.2949(2) 0.0202(13) Uani 1 1 d . . . N7 N 0.8098(3) -0.24873(14) 0.2519(2) 0.0179(13) Uani 1 1 d . . . N8 N 0.8257(3) -0.21622(14) 0.1686(2) 0.0194(13) Uani 1 1 d . . . N9 N 0.5939(3) -0.25087(14) 0.2780(2) 0.0171(13) Uani 1 1 d . . . N10 N 0.6024(3) -0.29390(14) 0.2083(2) 0.0202(13) Uani 1 1 d . . . N11 N 0.6923(3) -0.17387(13) 0.2637(2) 0.0151(12) Uani 1 1 d . . . N12 N 0.5308(3) -0.16975(13) 0.2037(2) 0.0179(13) Uani 1 1 d . . . C1 C 0.1930(4) -0.01703(17) 0.1776(3) 0.0213(16) Uani 1 1 d . . . C2 C 0.1570(4) -0.03881(17) 0.2158(3) 0.0200(16) Uani 1 1 d . . . C3 C 0.0713(5) -0.05749(18) 0.1859(3) 0.0324(19) Uani 1 1 d . . . H3 H 0.0462 -0.0728 0.2106 0.039 Uiso 1 1 calc R . . C4 C 0.0227(4) -0.0542(2) 0.1215(3) 0.034(2) Uani 1 1 d . . . H4 H -0.0368 -0.0663 0.1028 0.041 Uiso 1 1 calc R . . C5 C 0.0598(4) -0.03345(19) 0.0846(3) 0.0303(19) Uani 1 1 d . . . H5 H 0.0263 -0.0316 0.0401 0.036 Uiso 1 1 calc R . . C6 C 0.1469(4) -0.01470(17) 0.1115(3) 0.0194(16) Uani 1 1 d . . . C7 C 0.2122(4) -0.04343(17) 0.2857(3) 0.0238(17) Uani 1 1 d . . . H7A H 0.2245 -0.0200 0.3055 0.029 Uiso 1 1 calc R . . H7B H 0.2763 -0.0538 0.2893 0.029 Uiso 1 1 calc R . . C8 C 0.1649(5) -0.06584(19) 0.3246(3) 0.0362(19) Uani 1 1 d . . . H8A H 0.1018 -0.0558 0.3224 0.054 Uiso 1 1 calc R . . H8B H 0.2071 -0.0665 0.3692 0.054 Uiso 1 1 calc R . . H8C H 0.1554 -0.0896 0.3073 0.054 Uiso 1 1 calc R . . C9 C 0.1925(4) 0.00414(18) 0.0690(3) 0.0267(17) Uani 1 1 d . . . H9A H 0.2338 0.0233 0.0932 0.032 Uiso 1 1 calc R . . H9B H 0.1408 0.0146 0.0328 0.032 Uiso 1 1 calc R . . C10 C 0.2549(5) -0.02031(19) 0.0429(3) 0.0357(19) Uani 1 1 d . . . H10A H 0.3081 -0.0299 0.0785 0.054 Uiso 1 1 calc R . . H10B H 0.2819 -0.0072 0.0144 0.054 Uiso 1 1 calc R . . H10C H 0.2144 -0.0395 0.0191 0.054 Uiso 1 1 calc R . . C11 C 0.3635(4) -0.01759(17) 0.2262(3) 0.0183(15) Uani 1 1 d . . . H11 H 0.3625 -0.0415 0.2145 0.022 Uiso 1 1 calc R . . C12 C 0.5298(4) -0.02329(16) 0.2818(3) 0.0155(15) Uani 1 1 d . . . C13 C 0.5830(4) -0.02199(18) 0.3478(3) 0.0218(16) Uani 1 1 d . . . C14 C 0.6730(4) -0.03973(18) 0.3685(3) 0.0276(18) Uani 1 1 d . . . H14 H 0.7098 -0.0395 0.4126 0.033 Uiso 1 1 calc R . . C15 C 0.7087(5) -0.05719(17) 0.3267(3) 0.0292(18) Uani 1 1 d . . . H15 H 0.7687 -0.0694 0.3419 0.035 Uiso 1 1 calc R . . C16 C 0.6572(4) -0.05699(16) 0.2625(3) 0.0239(17) Uani 1 1 d . . . H16 H 0.6836 -0.0686 0.2337 0.029 Uiso 1 1 calc R . . C17 C 0.5674(4) -0.04030(16) 0.2384(3) 0.0180(15) Uani 1 1 d . . . C18 C 0.5456(4) -0.00275(19) 0.3945(3) 0.0293(18) Uani 1 1 d . . . H18A H 0.5178 0.0199 0.3756 0.035 Uiso 1 1 calc R . . H18B H 0.6006 0.0022 0.4336 0.035 Uiso 1 1 calc R . . C19 C 0.4679(5) -0.0234(2) 0.4126(3) 0.044(2) Uani 1 1 d . . . H19A H 0.4100 -0.0260 0.3749 0.066 Uiso 1 1 calc R . . H19B H 0.4504 -0.0108 0.4460 0.066 Uiso 1 1 calc R . . H19C H 0.4934 -0.0465 0.4284 0.066 Uiso 1 1 calc R . . C20 C 0.5131(4) -0.04076(18) 0.1674(3) 0.0295(18) Uani 1 1 d . . . H20A H 0.4624 -0.0591 0.1590 0.035 Uiso 1 1 calc R . . H20B H 0.4794 -0.0180 0.1556 0.035 Uiso 1 1 calc R . . C21 C 0.5734(5) -0.0471(2) 0.1245(3) 0.043(2) Uani 1 1 d . . . H21A H 0.6286 -0.0309 0.1356 0.065 Uiso 1 1 calc R . . H21B H 0.5335 -0.0434 0.0800 0.065 Uiso 1 1 calc R . . H21C H 0.5976 -0.0712 0.1300 0.065 Uiso 1 1 calc R . . C22 C 0.4426(4) 0.06731(17) 0.1591(3) 0.0180(15) Uani 1 1 d . . . C23 C 0.3955(4) 0.06855(18) 0.0936(3) 0.0260(17) Uani 1 1 d . . . C24 C 0.4474(5) 0.05753(19) 0.0533(3) 0.035(2) Uani 1 1 d . . . H24 H 0.4160 0.0576 0.0084 0.042 Uiso 1 1 calc R . . C25 C 0.5432(5) 0.0466(2) 0.0773(3) 0.039(2) Uani 1 1 d . . . H25 H 0.5768 0.0391 0.0491 0.046 Uiso 1 1 calc R . . C26 C 0.5895(4) 0.04662(17) 0.1424(3) 0.0260(17) Uani 1 1 d . . . H26 H 0.6556 0.0394 0.1586 0.031 Uiso 1 1 calc R . . C27 C 0.5414(4) 0.05707(17) 0.1847(3) 0.0215(16) Uani 1 1 d . . . C28 C 0.2973(4) 0.08508(19) 0.0663(3) 0.0282(18) Uani 1 1 d . . . H28A H 0.2617 0.0834 0.0977 0.034 Uiso 1 1 calc R . . H28B H 0.2596 0.0723 0.0273 0.034 Uiso 1 1 calc R . . C29 C 0.3062(5) 0.1232(2) 0.0500(3) 0.038(2) Uani 1 1 d . . . H29A H 0.3390 0.1363 0.0891 0.058 Uiso 1 1 calc R . . H29B H 0.2412 0.1330 0.0297 0.058 Uiso 1 1 calc R . . H29C H 0.3443 0.1250 0.0205 0.058 Uiso 1 1 calc R . . C30 C 0.5937(4) 0.05937(17) 0.2563(3) 0.0254(17) Uani 1 1 d . . . H30A H 0.5541 0.0470 0.2787 0.030 Uiso 1 1 calc R . . H30B H 0.5971 0.0843 0.2692 0.030 Uiso 1 1 calc R . . C31 C 0.6970(4) 0.04414(18) 0.2790(3) 0.0329(19) Uani 1 1 d . . . H31A H 0.6947 0.0194 0.2671 0.049 Uiso 1 1 calc R . . H31B H 0.7242 0.0464 0.3255 0.049 Uiso 1 1 calc R . . H31C H 0.7380 0.0569 0.2588 0.049 Uiso 1 1 calc R . . C32 C 0.4205(4) 0.10925(18) 0.2309(3) 0.0222(17) Uani 1 1 d . . . H32 H 0.4630 0.1239 0.2173 0.027 Uiso 1 1 calc R . . C33 C 0.4177(4) 0.15096(18) 0.3096(3) 0.0208(16) Uani 1 1 d . . . C34 C 0.4527(4) 0.15011(19) 0.3764(3) 0.0214(16) Uani 1 1 d . . . C35 C 0.4767(4) 0.1812(2) 0.4102(3) 0.0303(19) Uani 1 1 d . . . H35 H 0.5028 0.1807 0.4554 0.036 Uiso 1 1 calc R . . C36 C 0.4630(5) 0.2128(2) 0.3784(4) 0.0338(19) Uani 1 1 d . . . H36 H 0.4777 0.2341 0.4018 0.041 Uiso 1 1 calc R . . C37 C 0.4276(4) 0.21342(18) 0.3124(3) 0.0257(17) Uani 1 1 d . . . H37 H 0.4192 0.2353 0.2910 0.031 Uiso 1 1 calc R . . C38 C 0.4040(4) 0.18300(18) 0.2762(3) 0.0189(16) Uani 1 1 d . . . C39 C 0.4659(5) 0.11410(19) 0.4098(3) 0.0349(19) Uani 1 1 d . . . H39A H 0.4023 0.1020 0.3967 0.042 Uiso 1 1 calc R . . H39B H 0.5110 0.1000 0.3943 0.042 Uiso 1 1 calc R . . C40 C 0.5035(5) 0.1151(2) 0.4804(3) 0.062(3) Uani 1 1 d . . . H40A H 0.5663 0.1272 0.4942 0.092 Uiso 1 1 calc R . . H40B H 0.5120 0.0911 0.4971 0.092 Uiso 1 1 calc R . . H40C H 0.4572 0.1275 0.4966 0.092 Uiso 1 1 calc R . . C41 C 0.3668(4) 0.18469(18) 0.2045(3) 0.0286(18) Uani 1 1 d . . . H41A H 0.3166 0.1664 0.1888 0.034 Uiso 1 1 calc R . . H41B H 0.4212 0.1790 0.1882 0.034 Uiso 1 1 calc R . . C42 C 0.3230(5) 0.21987(18) 0.1759(3) 0.036(2) Uani 1 1 d . . . H42A H 0.2731 0.2270 0.1946 0.055 Uiso 1 1 calc R . . H42B H 0.2936 0.2175 0.1296 0.055 Uiso 1 1 calc R . . H42C H 0.3744 0.2376 0.1853 0.055 Uiso 1 1 calc R . . C43 C 0.0861(4) 0.02209(17) 0.3270(3) 0.0199(16) Uani 1 1 d . . . C44 C -0.0100(4) 0.01115(17) 0.2940(3) 0.0240(17) Uani 1 1 d . . . C45 C -0.0633(5) -0.00400(19) 0.3296(4) 0.0329(19) Uani 1 1 d . . . H45 H -0.1284 -0.0112 0.3086 0.040 Uiso 1 1 calc R . . C46 C -0.0238(5) -0.00865(19) 0.3940(4) 0.037(2) Uani 1 1 d . . . H46 H -0.0613 -0.0191 0.4174 0.044 Uiso 1 1 calc R . . C47 C 0.0709(5) 0.00184(18) 0.4256(3) 0.0335(18) Uani 1 1 d . . . H47 H 0.0976 -0.0013 0.4705 0.040 Uiso 1 1 calc R . . C48 C 0.1266(4) 0.01686(18) 0.3923(3) 0.0248(17) Uani 1 1 d . . . C49 C -0.0532(4) 0.01435(17) 0.2227(3) 0.0259(17) Uani 1 1 d . . . H49A H -0.0014 0.0095 0.2037 0.031 Uiso 1 1 calc R . . H49B H -0.0738 0.0389 0.2125 0.031 Uiso 1 1 calc R . . C50 C -0.1397(4) -0.00921(19) 0.1902(3) 0.039(2) Uani 1 1 d . . . H50A H -0.1227 -0.0335 0.2027 0.058 Uiso 1 1 calc R . . H50B H -0.1565 -0.0070 0.1437 0.058 Uiso 1 1 calc R . . H50C H -0.1956 -0.0022 0.2032 0.058 Uiso 1 1 calc R . . C51 C 0.2288(4) 0.02850(19) 0.4283(3) 0.0314(19) Uani 1 1 d . . . H51A H 0.2699 0.0254 0.4005 0.038 Uiso 1 1 calc R . . H51B H 0.2554 0.0133 0.4662 0.038 Uiso 1 1 calc R . . C52 C 0.2343(5) 0.0664(2) 0.4499(3) 0.045(2) Uani 1 1 d . . . H52A H 0.2129 0.0817 0.4124 0.068 Uiso 1 1 calc R . . H52B H 0.3016 0.0721 0.4749 0.068 Uiso 1 1 calc R . . H52C H 0.1922 0.0698 0.4763 0.068 Uiso 1 1 calc R . . C53 C 0.1185(4) 0.06356(17) 0.2579(3) 0.0185(16) Uani 1 1 d . . . H53 H 0.0576 0.0740 0.2544 0.022 Uiso 1 1 calc R . . C54 C 0.1463(4) 0.11085(18) 0.1977(3) 0.0196(16) Uani 1 1 d . . . C55 C 0.1577(4) 0.14025(18) 0.2379(3) 0.0191(16) Uani 1 1 d . . . C56 C 0.1332(4) 0.17306(18) 0.2103(3) 0.0236(17) Uani 1 1 d . . . H56 H 0.1419 0.1931 0.2369 0.028 Uiso 1 1 calc R . . C57 C 0.0960(4) 0.1769(2) 0.1443(3) 0.0310(19) Uani 1 1 d . . . H57 H 0.0807 0.1995 0.1261 0.037 Uiso 1 1 calc R . . C58 C 0.0814(5) 0.1482(2) 0.1056(3) 0.0307(19) Uani 1 1 d . . . H58 H 0.0555 0.1511 0.0606 0.037 Uiso 1 1 calc R . . C59 C 0.1038(4) 0.11470(19) 0.1308(3) 0.0219(17) Uani 1 1 d . . . C60 C 0.1896(4) 0.13555(17) 0.3101(3) 0.0190(16) Uani 1 1 d . . . H60A H 0.2509 0.1220 0.3233 0.023 Uiso 1 1 calc R . . H60B H 0.1397 0.1214 0.3208 0.023 Uiso 1 1 calc R . . C61 C 0.2057(4) 0.16925(18) 0.3498(3) 0.0299(18) Uani 1 1 d . . . H61A H 0.2567 0.1832 0.3410 0.045 Uiso 1 1 calc R . . H61B H 0.2258 0.1633 0.3953 0.045 Uiso 1 1 calc R . . H61C H 0.1451 0.1827 0.3383 0.045 Uiso 1 1 calc R . . C62 C 0.0755(4) 0.08260(19) 0.0890(3) 0.0298(18) Uani 1 1 d . . . H62A H 0.1201 0.0631 0.1084 0.036 Uiso 1 1 calc R . . H62B H 0.0818 0.0876 0.0465 0.036 Uiso 1 1 calc R . . C63 C -0.0296(5) 0.0717(2) 0.0811(3) 0.051(2) Uani 1 1 d . . . H63A H -0.0365 0.0677 0.1232 0.077 Uiso 1 1 calc R . . H63B H -0.0452 0.0501 0.0559 0.077 Uiso 1 1 calc R . . H63C H -0.0742 0.0903 0.0590 0.077 Uiso 1 1 calc R . . C64 C 0.8435(4) -0.28016(17) 0.2874(3) 0.0136(15) Uani 1 1 d . . . C65 C 0.8828(4) -0.27790(18) 0.3545(3) 0.0204(16) Uani 1 1 d . . . C66 C 0.9132(4) -0.3086(2) 0.3897(3) 0.0264(18) Uani 1 1 d . . . H66 H 0.9379 -0.3075 0.4350 0.032 Uiso 1 1 calc R . . C67 C 0.9079(4) -0.34057(19) 0.3594(3) 0.0252(17) Uani 1 1 d . . . H67 H 0.9286 -0.3612 0.3839 0.030 Uiso 1 1 calc R . . C68 C 0.8729(4) -0.34246(17) 0.2940(3) 0.0203(16) Uani 1 1 d . . . H68 H 0.8700 -0.3645 0.2738 0.024 Uiso 1 1 calc R . . C69 C 0.8414(4) -0.31273(18) 0.2565(3) 0.0184(16) Uani 1 1 d . . . C70 C 0.8994(4) -0.24246(18) 0.3866(3) 0.0254(17) Uani 1 1 d . . . H70A H 0.8963 -0.2449 0.4305 0.030 Uiso 1 1 calc R . . H70B H 0.8466 -0.2264 0.3629 0.030 Uiso 1 1 calc R . . C71 C 0.9970(4) -0.22652(19) 0.3896(3) 0.0334(19) Uani 1 1 d . . . H71A H 1.0497 -0.2420 0.4141 0.050 Uiso 1 1 calc R . . H71B H 1.0040 -0.2036 0.4105 0.050 Uiso 1 1 calc R . . H71C H 1.0001 -0.2237 0.3462 0.050 Uiso 1 1 calc R . . C72 C 0.8100(4) -0.31448(17) 0.1840(3) 0.0215(16) Uani 1 1 d . . . H72A H 0.8571 -0.3010 0.1694 0.026 Uiso 1 1 calc R . . H72B H 0.7460 -0.3028 0.1668 0.026 Uiso 1 1 calc R . . C73 C 0.8017(4) -0.35122(18) 0.1551(3) 0.0296(18) Uani 1 1 d . . . H73A H 0.8653 -0.3628 0.1701 0.044 Uiso 1 1 calc R . . H73B H 0.7803 -0.3495 0.1084 0.044 Uiso 1 1 calc R . . H73C H 0.7542 -0.3649 0.1683 0.044 Uiso 1 1 calc R . . C74 C 0.8592(4) -0.23935(17) 0.2122(3) 0.0182(16) Uani 1 1 d . . . H74 H 0.9201 -0.2501 0.2165 0.022 Uiso 1 1 calc R . . C75 C 0.8841(4) -0.20740(17) 0.1291(3) 0.0219(16) Uani 1 1 d . . . C76 C 0.8449(5) -0.2155(2) 0.0642(3) 0.035(2) Uani 1 1 d . . . C77 C 0.9015(6) -0.2077(2) 0.0246(3) 0.050(2) Uani 1 1 d . . . H77 H 0.8773 -0.2129 -0.0198 0.060 Uiso 1 1 calc R . . C78 C 0.9915(5) -0.1925(2) 0.0498(4) 0.050(2) Uani 1 1 d . . . H78 H 1.0289 -0.1876 0.0225 0.060 Uiso 1 1 calc R . . C79 C 1.0289(5) -0.1842(2) 0.1139(4) 0.040(2) Uani 1 1 d . . . H79 H 1.0905 -0.1730 0.1298 0.048 Uiso 1 1 calc R . . C80 C 0.9767(5) -0.19205(19) 0.1552(3) 0.0333(19) Uani 1 1 d . . . C81 C 0.7483(4) -0.2350(2) 0.0375(3) 0.039(2) Uani 1 1 d . . . H81A H 0.7445 -0.2458 -0.0039 0.047 Uiso 1 1 calc R . . H81B H 0.7450 -0.2539 0.0673 0.047 Uiso 1 1 calc R . . C82 C 0.6630(5) -0.2102(2) 0.0284(3) 0.052(2) Uani 1 1 d . . . H82A H 0.6735 -0.1961 0.0671 0.079 Uiso 1 1 calc R . . H82B H 0.6029 -0.2237 0.0201 0.079 Uiso 1 1 calc R . . H82C H 0.6577 -0.1947 -0.0080 0.079 Uiso 1 1 calc R . . C83 C 1.0168(5) -0.18433(19) 0.2252(4) 0.040(2) Uani 1 1 d . . . H83A H 0.9631 -0.1753 0.2393 0.048 Uiso 1 1 calc R . . H83B H 1.0386 -0.2067 0.2479 0.048 Uiso 1 1 calc R . . C84 C 1.0995(5) -0.1589(2) 0.2461(4) 0.056(2) Uani 1 1 d . . . H84C H 1.1556 -0.1683 0.2359 0.084 Uiso 1 1 calc R . . H84B H 1.1172 -0.1552 0.2923 0.084 Uiso 1 1 calc R . . H84A H 1.0798 -0.1366 0.2238 0.084 Uiso 1 1 calc R . . C85 C 0.5392(4) -0.23824(17) 0.3173(3) 0.0203(16) Uani 1 1 d . . . C86 C 0.4393(4) -0.22935(17) 0.2884(3) 0.0239(17) Uani 1 1 d . . . C87 C 0.3880(5) -0.21857(19) 0.3276(4) 0.036(2) Uani 1 1 d . . . H87 H 0.3212 -0.2125 0.3095 0.044 Uiso 1 1 calc R . . C88 C 0.4325(5) -0.2163(2) 0.3936(4) 0.042(2) Uani 1 1 d . . . H88 H 0.3965 -0.2079 0.4197 0.051 Uiso 1 1 calc R . . C89 C 0.5262(5) -0.22599(19) 0.4207(3) 0.0339(19) Uani 1 1 d . . . H89 H 0.5548 -0.2247 0.4658 0.041 Uiso 1 1 calc R . . C90 C 0.5821(4) -0.23792(18) 0.3837(3) 0.0241(17) Uani 1 1 d . . . C91 C 0.6808(4) -0.2527(2) 0.4157(3) 0.0280(18) Uani 1 1 d . . . H91A H 0.7165 -0.2371 0.4512 0.034 Uiso 1 1 calc R . . H91B H 0.7172 -0.2534 0.3847 0.034 Uiso 1 1 calc R . . C92 C 0.6772(5) -0.2893(2) 0.4419(4) 0.053(2) Uani 1 1 d . . . H92A H 0.6431 -0.2886 0.4737 0.080 Uiso 1 1 calc R . . H92B H 0.7436 -0.2979 0.4620 0.080 Uiso 1 1 calc R . . H92C H 0.6426 -0.3049 0.4069 0.080 Uiso 1 1 calc R . . C93 C 0.3921(4) -0.23383(18) 0.2171(3) 0.0260(17) Uani 1 1 d . . . H93B H 0.3938 -0.2590 0.2068 0.031 Uiso 1 1 calc R . . H93A H 0.4321 -0.2213 0.1952 0.031 Uiso 1 1 calc R . . C94 C 0.2863(4) -0.2209(2) 0.1890(3) 0.040(2) Uani 1 1 d . . . H94A H 0.2446 -0.2342 0.2081 0.060 Uiso 1 1 calc R . . H94B H 0.2638 -0.2244 0.1427 0.060 Uiso 1 1 calc R . . H94C H 0.2831 -0.1960 0.1986 0.060 Uiso 1 1 calc R . . C95 C 0.5698(4) -0.28374(18) 0.2535(3) 0.0184(16) Uani 1 1 d . . . H95 H 0.5302 -0.2986 0.2692 0.022 Uiso 1 1 calc R . . C96 C 0.5795(4) -0.32793(19) 0.1840(3) 0.0211(16) Uani 1 1 d . . . C97 C 0.5448(4) -0.33186(18) 0.1173(3) 0.0230(17) Uani 1 1 d . . . C98 C 0.5220(5) -0.3646(2) 0.0911(3) 0.034(2) Uani 1 1 d . . . H98 H 0.4958 -0.3668 0.0460 0.041 Uiso 1 1 calc R . . C99 C 0.5358(4) -0.39459(19) 0.1282(3) 0.0296(18) Uani 1 1 d . . . H99 H 0.5191 -0.4169 0.1091 0.035 Uiso 1 1 calc R . . C100 C 0.5748(4) -0.39105(18) 0.1939(3) 0.0272(18) Uani 1 1 d . . . H100 H 0.5876 -0.4115 0.2196 0.033 Uiso 1 1 calc R . . C101 C 0.5964(4) -0.35806(18) 0.2242(3) 0.0193(16) Uani 1 1 d . . . C102 C 0.5317(4) -0.2995(2) 0.0740(3) 0.0329(19) Uani 1 1 d . . . H10E H 0.5902 -0.2845 0.0901 0.039 Uiso 1 1 calc R . . H10D H 0.5275 -0.3073 0.0304 0.039 Uiso 1 1 calc R . . C103 C 0.4422(5) -0.27776(19) 0.0701(3) 0.038(2) Uani 1 1 d . . . H10F H 0.3837 -0.2922 0.0535 0.057 Uiso 1 1 calc R . . H10G H 0.4383 -0.2578 0.0415 0.057 Uiso 1 1 calc R . . H10H H 0.4468 -0.2692 0.1128 0.057 Uiso 1 1 calc R . . C104 C 0.6377(4) -0.35495(17) 0.2964(3) 0.0231(16) Uani 1 1 d . . . H10J H 0.5837 -0.3496 0.3132 0.028 Uiso 1 1 calc R . . H10I H 0.6832 -0.3349 0.3069 0.028 Uiso 1 1 calc R . . C105 C 0.6915(4) -0.38748(17) 0.3309(3) 0.0320(18) Uani 1 1 d . . . H10K H 0.6448 -0.4066 0.3271 0.048 Uiso 1 1 calc R . . H10L H 0.7233 -0.3820 0.3762 0.048 Uiso 1 1 calc R . . H10M H 0.7406 -0.3946 0.3116 0.048 Uiso 1 1 calc R . . C106 C 0.7793(4) -0.15310(17) 0.2910(3) 0.0185(16) Uani 1 1 d . . . C107 C 0.8156(4) -0.13296(16) 0.2503(3) 0.0165(15) Uani 1 1 d . . . C108 C 0.8953(4) -0.11202(17) 0.2791(3) 0.0206(16) Uani 1 1 d . . . H108 H 0.9214 -0.0981 0.2528 0.025 Uiso 1 1 calc R . . C109 C 0.9383(4) -0.11051(18) 0.3445(3) 0.0251(17) Uani 1 1 d . . . H109 H 0.9933 -0.0960 0.3628 0.030 Uiso 1 1 calc R . . C110 C 0.9003(4) -0.13038(19) 0.3829(3) 0.0280(18) Uani 1 1 d . . . H110 H 0.9304 -0.1296 0.4279 0.034 Uiso 1 1 calc R . . C111 C 0.8193(4) -0.15153(16) 0.3577(3) 0.0173(15) Uani 1 1 d . . . C112 C 0.7669(4) -0.13360(17) 0.1799(3) 0.0256(17) Uani 1 1 d . . . H11A H 0.7000 -0.1244 0.1709 0.031 Uiso 1 1 calc R . . H11B H 0.7613 -0.1583 0.1656 0.031 Uiso 1 1 calc R . . C113 C 0.8168(5) -0.11284(19) 0.1394(3) 0.038(2) Uani 1 1 d . . . H11C H 0.8138 -0.0878 0.1480 0.058 Uiso 1 1 calc R . . H11D H 0.7833 -0.1174 0.0940 0.058 Uiso 1 1 calc R . . H11E H 0.8849 -0.1201 0.1504 0.058 Uiso 1 1 calc R . . C114 C 0.7730(5) -0.16924(18) 0.4009(3) 0.0304(18) Uani 1 1 d . . . H11F H 0.8239 -0.1813 0.4354 0.036 Uiso 1 1 calc R . . H11G H 0.7269 -0.1872 0.3764 0.036 Uiso 1 1 calc R . . C115 C 0.7185(5) -0.1438(2) 0.4309(3) 0.040(2) Uani 1 1 d . . . H11H H 0.7630 -0.1254 0.4536 0.061 Uiso 1 1 calc R . . H11I H 0.6936 -0.1565 0.4610 0.061 Uiso 1 1 calc R . . H11J H 0.6641 -0.1334 0.3973 0.061 Uiso 1 1 calc R . . C116 C 0.6093(4) -0.15501(18) 0.2403(3) 0.0228(16) Uani 1 1 d . . . H116 H 0.6087 -0.1309 0.2507 0.027 Uiso 1 1 calc R . . C117 C 0.4431(4) -0.14965(17) 0.1835(3) 0.0214(16) Uani 1 1 d . . . C118 C 0.3913(4) -0.14968(18) 0.1176(3) 0.0232(17) Uani 1 1 d . . . C119 C 0.3016(4) -0.13214(19) 0.0964(3) 0.0320(19) Uani 1 1 d . . . H119 H 0.2664 -0.1315 0.0520 0.038 Uiso 1 1 calc R . . C120 C 0.2645(4) -0.11609(18) 0.1382(3) 0.0303(18) Uani 1 1 d . . . H120 H 0.2032 -0.1047 0.1229 0.036 Uiso 1 1 calc R . . C121 C 0.3150(4) -0.11617(18) 0.2026(3) 0.0302(18) Uani 1 1 d . . . H121 H 0.2881 -0.1047 0.2313 0.036 Uiso 1 1 calc R . . C122 C 0.4044(4) -0.13266(17) 0.2262(3) 0.0242(17) Uani 1 1 d . . . C123 C 0.4330(4) -0.16625(19) 0.0702(3) 0.0304(19) Uani 1 1 d . . . H12F H 0.3792 -0.1747 0.0330 0.036 Uiso 1 1 calc R . . H12G H 0.4730 -0.1867 0.0903 0.036 Uiso 1 1 calc R . . C124 C 0.4955(5) -0.1408(2) 0.0473(3) 0.045(2) Uani 1 1 d . . . H12H H 0.4549 -0.1215 0.0241 0.068 Uiso 1 1 calc R . . H12I H 0.5246 -0.1529 0.0188 0.068 Uiso 1 1 calc R . . H12J H 0.5471 -0.1315 0.0841 0.068 Uiso 1 1 calc R . . C125 C 0.4570(5) -0.1325(2) 0.2981(3) 0.035(2) Uani 1 1 d . . . H12A H 0.4875 -0.1558 0.3101 0.042 Uiso 1 1 calc R . . H12B H 0.5103 -0.1152 0.3070 0.042 Uiso 1 1 calc R . . C126 C 0.3990(6) -0.1249(2) 0.3397(3) 0.063(3) Uani 1 1 d . . . H12C H 0.3810 -0.1001 0.3360 0.094 Uiso 1 1 calc R . . H12D H 0.4371 -0.1301 0.3840 0.094 Uiso 1 1 calc R . . H12E H 0.3399 -0.1392 0.3270 0.094 Uiso 1 1 calc R . . C127 C 0.7605(6) -0.4382(2) 0.0354(4) 0.065(3) Uani 1 1 d . . . H12K H 0.7849 -0.4481 0.0025 0.097 Uiso 1 1 calc R . . H12L H 0.7281 -0.4566 0.0522 0.097 Uiso 1 1 calc R . . H12M H 0.8150 -0.4287 0.0702 0.097 Uiso 1 1 calc R . . C128 C 0.6894(5) -0.4096(2) 0.0068(4) 0.050(2) Uani 1 1 d . . . H12N H 0.6363 -0.4188 -0.0301 0.059 Uiso 1 1 calc R . . H12O H 0.6606 -0.4008 0.0389 0.059 Uiso 1 1 calc R . . C129 C 0.6793(5) -0.3540(2) -0.0404(4) 0.052(2) Uani 1 1 d . . . H12P H 0.6477 -0.3449 -0.0100 0.063 Uiso 1 1 calc R . . H12Q H 0.6275 -0.3618 -0.0794 0.063 Uiso 1 1 calc R . . C130 C 0.7366(5) -0.3258(2) -0.0573(4) 0.056(2) Uani 1 1 d . . . H13A H 0.7900 -0.3189 -0.0192 0.085 Uiso 1 1 calc R . . H13B H 0.6944 -0.3056 -0.0736 0.085 Uiso 1 1 calc R . . H13C H 0.7632 -0.3342 -0.0902 0.085 Uiso 1 1 calc R . . 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 0.01708(13) 0.01317(14) 0.01702(14) -0.00076(12) 0.00490(10) -0.00024(11) Bi2 0.01633(13) 0.01376(14) 0.01675(14) -0.00027(12) 0.00468(10) -0.00039(12) O1 0.039(3) 0.034(4) 0.054(3) -0.002(3) 0.015(3) 0.003(3) N1 0.014(3) 0.013(3) 0.019(3) 0.003(3) 0.001(2) 0.002(2) N2 0.016(3) 0.014(3) 0.017(3) 0.005(3) 0.006(2) 0.004(3) N3 0.024(3) 0.015(3) 0.014(3) -0.002(3) 0.007(2) 0.000(3) N4 0.021(3) 0.010(3) 0.019(3) 0.002(3) 0.005(2) -0.005(3) N5 0.020(3) 0.015(3) 0.014(3) 0.001(3) 0.009(2) -0.002(3) N6 0.022(3) 0.014(3) 0.027(3) 0.008(3) 0.010(3) 0.005(3) N7 0.024(3) 0.019(4) 0.011(3) 0.006(3) 0.005(2) 0.006(3) N8 0.021(3) 0.020(4) 0.018(3) 0.009(3) 0.009(2) 0.005(3) N9 0.020(3) 0.023(4) 0.009(3) -0.002(3) 0.005(2) 0.001(3) N10 0.024(3) 0.013(3) 0.021(3) -0.001(3) 0.003(3) -0.004(3) N11 0.013(3) 0.010(3) 0.021(3) -0.005(3) 0.004(2) 0.001(2) N12 0.014(3) 0.010(3) 0.031(3) -0.005(3) 0.009(2) -0.003(2) C1 0.017(3) 0.013(4) 0.032(4) -0.004(3) 0.007(3) -0.001(3) C2 0.017(3) 0.011(4) 0.035(4) -0.002(3) 0.011(3) 0.007(3) C3 0.032(4) 0.023(5) 0.046(5) -0.003(4) 0.018(4) 0.002(4) C4 0.018(4) 0.040(6) 0.043(5) -0.013(4) 0.008(4) -0.012(4) C5 0.021(4) 0.029(5) 0.034(5) -0.009(4) -0.001(3) 0.008(4) C6 0.017(3) 0.013(4) 0.029(4) -0.004(3) 0.008(3) 0.010(3) C7 0.030(4) 0.016(4) 0.030(4) -0.006(3) 0.017(3) 0.000(3) C8 0.052(5) 0.028(5) 0.037(5) -0.005(4) 0.026(4) -0.011(4) C9 0.025(4) 0.030(5) 0.020(4) -0.003(4) 0.001(3) 0.000(3) C10 0.040(4) 0.031(5) 0.036(5) -0.015(4) 0.013(4) -0.013(4) C11 0.029(4) 0.012(4) 0.018(4) -0.002(3) 0.013(3) -0.002(3) C12 0.019(3) 0.007(4) 0.020(4) -0.004(3) 0.005(3) -0.001(3) C13 0.024(4) 0.022(4) 0.019(4) 0.000(3) 0.007(3) -0.006(3) C14 0.023(4) 0.025(5) 0.028(4) 0.008(4) -0.002(3) 0.000(3) C15 0.025(4) 0.017(5) 0.047(5) 0.010(4) 0.012(4) 0.009(3) C16 0.025(4) 0.013(4) 0.038(5) 0.001(4) 0.015(3) 0.000(3) C17 0.021(3) 0.009(4) 0.021(4) -0.003(3) 0.003(3) -0.004(3) C18 0.025(4) 0.037(5) 0.017(4) 0.000(4) -0.004(3) 0.007(4) C19 0.052(5) 0.052(6) 0.032(5) -0.004(4) 0.019(4) -0.006(4) C20 0.032(4) 0.027(5) 0.029(4) -0.004(4) 0.009(3) 0.003(3) C21 0.052(5) 0.042(6) 0.042(5) -0.015(4) 0.023(4) 0.007(4) C22 0.024(4) 0.014(4) 0.021(4) -0.001(3) 0.013(3) -0.005(3) C23 0.030(4) 0.027(5) 0.023(4) -0.002(4) 0.010(3) -0.006(3) C24 0.040(4) 0.039(6) 0.029(4) 0.002(4) 0.017(4) -0.003(4) C25 0.044(5) 0.044(6) 0.035(5) -0.006(4) 0.023(4) 0.006(4) C26 0.023(4) 0.022(5) 0.040(5) 0.006(4) 0.020(3) 0.006(3) C27 0.029(4) 0.013(4) 0.025(4) 0.007(3) 0.011(3) -0.002(3) C28 0.029(4) 0.024(5) 0.026(4) 0.008(4) -0.001(3) -0.002(3) C29 0.035(4) 0.041(6) 0.036(5) 0.012(4) 0.007(3) 0.004(4) C30 0.023(4) 0.014(4) 0.040(5) 0.005(3) 0.011(3) 0.003(3) C31 0.033(4) 0.026(5) 0.042(5) 0.002(4) 0.014(3) 0.003(4) C32 0.013(3) 0.024(5) 0.028(4) 0.001(4) 0.004(3) 0.002(3) C33 0.015(3) 0.020(4) 0.026(4) -0.007(3) 0.006(3) -0.006(3) C34 0.016(3) 0.022(5) 0.024(4) 0.000(4) 0.004(3) 0.006(3) C35 0.023(4) 0.034(5) 0.031(4) -0.014(4) 0.004(3) -0.002(4) C36 0.034(4) 0.025(5) 0.044(5) -0.014(4) 0.014(4) -0.012(4) C37 0.028(4) 0.012(4) 0.043(5) 0.004(4) 0.019(4) -0.002(3) C38 0.015(3) 0.017(4) 0.026(4) -0.001(3) 0.008(3) -0.002(3) C39 0.046(5) 0.027(5) 0.026(4) -0.007(4) 0.003(4) -0.003(4) C40 0.063(6) 0.077(8) 0.043(6) 0.009(5) 0.015(4) -0.012(5) C41 0.024(4) 0.019(5) 0.044(5) -0.003(4) 0.013(3) 0.000(3) C42 0.041(4) 0.024(5) 0.040(5) 0.005(4) 0.008(4) -0.007(4) C43 0.019(3) 0.013(4) 0.031(4) 0.000(3) 0.013(3) -0.001(3) C44 0.028(4) 0.013(4) 0.035(5) 0.000(3) 0.015(3) 0.009(3) C45 0.025(4) 0.026(5) 0.051(5) -0.001(4) 0.017(4) -0.004(4) C46 0.040(5) 0.030(5) 0.052(5) 0.008(4) 0.030(4) 0.005(4) C47 0.046(5) 0.021(5) 0.035(4) 0.004(4) 0.015(4) 0.002(4) C48 0.028(4) 0.017(4) 0.033(5) 0.002(3) 0.015(3) 0.002(3) C49 0.022(4) 0.011(4) 0.043(5) -0.005(3) 0.008(3) 0.003(3) C50 0.027(4) 0.029(5) 0.058(5) -0.012(4) 0.011(4) -0.005(4) C51 0.041(4) 0.033(5) 0.015(4) 0.001(4) 0.001(3) 0.002(4) C52 0.052(5) 0.050(6) 0.024(4) 0.001(4) -0.001(4) -0.017(4) C53 0.022(4) 0.012(4) 0.021(4) -0.010(3) 0.005(3) -0.003(3) C54 0.013(3) 0.018(4) 0.030(4) -0.005(3) 0.010(3) -0.004(3) C55 0.010(3) 0.021(4) 0.029(4) 0.008(3) 0.011(3) 0.005(3) C56 0.025(4) 0.018(4) 0.033(5) 0.002(4) 0.016(3) 0.007(3) C57 0.026(4) 0.034(5) 0.036(5) 0.015(4) 0.014(3) 0.010(4) C58 0.040(4) 0.036(5) 0.020(4) 0.014(4) 0.016(3) 0.007(4) C59 0.015(3) 0.026(5) 0.026(4) 0.001(4) 0.007(3) -0.003(3) C60 0.023(3) 0.016(4) 0.020(4) -0.003(3) 0.009(3) -0.003(3) C61 0.027(4) 0.029(5) 0.035(4) -0.010(4) 0.011(3) 0.001(3) C62 0.026(4) 0.039(5) 0.024(4) -0.005(4) 0.008(3) -0.008(4) C63 0.045(5) 0.066(7) 0.038(5) -0.026(5) 0.006(4) -0.014(5) C64 0.012(3) 0.013(4) 0.019(4) 0.003(3) 0.010(3) 0.001(3) C65 0.019(3) 0.020(4) 0.023(4) 0.002(4) 0.008(3) 0.000(3) C66 0.024(4) 0.035(5) 0.017(4) 0.008(4) 0.002(3) 0.008(4) C67 0.020(4) 0.022(5) 0.035(5) 0.013(4) 0.011(3) 0.007(3) C68 0.025(4) 0.007(4) 0.029(4) 0.004(3) 0.008(3) 0.004(3) C69 0.016(3) 0.020(4) 0.021(4) 0.002(3) 0.009(3) -0.003(3) C70 0.027(4) 0.026(5) 0.022(4) -0.006(3) 0.007(3) 0.009(3) C71 0.027(4) 0.044(6) 0.031(4) -0.007(4) 0.011(3) -0.003(4) C72 0.018(3) 0.017(4) 0.027(4) 0.002(3) 0.005(3) 0.000(3) C73 0.029(4) 0.036(5) 0.023(4) -0.005(4) 0.008(3) -0.004(4) C74 0.019(3) 0.014(4) 0.024(4) -0.009(3) 0.010(3) 0.001(3) C75 0.028(4) 0.014(4) 0.029(4) 0.014(3) 0.017(3) 0.013(3) C76 0.038(4) 0.043(6) 0.025(5) 0.018(4) 0.013(4) 0.016(4) C77 0.053(5) 0.074(8) 0.032(5) 0.026(5) 0.026(4) 0.022(5) C78 0.038(5) 0.067(7) 0.059(6) 0.040(5) 0.035(4) 0.025(5) C79 0.029(4) 0.037(6) 0.061(6) 0.031(5) 0.024(4) 0.012(4) C80 0.029(4) 0.028(5) 0.046(5) 0.010(4) 0.017(4) 0.011(4) C81 0.030(4) 0.060(7) 0.024(4) 0.011(4) 0.004(3) 0.009(4) C82 0.049(5) 0.049(7) 0.050(5) 0.006(5) 0.003(4) 0.005(5) C83 0.026(4) 0.024(5) 0.070(6) -0.010(4) 0.016(4) -0.008(4) C84 0.041(5) 0.046(6) 0.081(6) -0.012(5) 0.018(4) -0.005(4) C85 0.020(3) 0.013(4) 0.033(4) -0.002(3) 0.015(3) 0.000(3) C86 0.023(4) 0.013(4) 0.037(5) -0.003(3) 0.011(3) -0.002(3) C87 0.027(4) 0.030(5) 0.056(6) 0.000(4) 0.020(4) 0.004(4) C88 0.056(5) 0.034(6) 0.047(6) -0.008(4) 0.032(4) 0.006(4) C89 0.037(4) 0.040(5) 0.030(4) -0.005(4) 0.018(4) 0.000(4) C90 0.027(4) 0.020(4) 0.023(4) -0.010(3) 0.005(3) -0.006(3) C91 0.026(4) 0.040(5) 0.019(4) -0.008(4) 0.008(3) -0.010(4) C92 0.042(5) 0.043(6) 0.069(6) 0.015(5) 0.009(4) 0.010(4) C93 0.018(3) 0.024(5) 0.035(4) 0.000(4) 0.008(3) -0.001(3) C94 0.021(4) 0.049(6) 0.049(5) 0.007(4) 0.010(3) 0.002(4) C95 0.012(3) 0.030(5) 0.008(4) -0.005(3) -0.004(3) 0.008(3) C96 0.017(3) 0.021(4) 0.024(4) -0.005(4) 0.006(3) -0.004(3) C97 0.028(4) 0.017(4) 0.025(4) -0.006(3) 0.011(3) -0.006(3) C98 0.033(4) 0.046(6) 0.024(4) -0.009(4) 0.010(3) -0.005(4) C99 0.040(4) 0.022(5) 0.031(5) -0.014(4) 0.016(4) -0.003(4) C100 0.029(4) 0.015(4) 0.045(5) -0.001(4) 0.022(4) 0.001(3) C101 0.013(3) 0.018(4) 0.029(4) -0.007(3) 0.009(3) -0.001(3) C102 0.032(4) 0.035(5) 0.030(4) -0.007(4) 0.009(3) -0.002(4) C103 0.050(5) 0.039(6) 0.021(4) 0.007(4) 0.003(3) 0.009(4) C104 0.031(4) 0.018(4) 0.025(4) -0.004(3) 0.015(3) 0.002(3) C105 0.037(4) 0.015(4) 0.041(5) 0.006(4) 0.010(3) -0.002(4) C106 0.015(3) 0.012(4) 0.025(4) -0.001(3) 0.001(3) 0.004(3) C107 0.014(3) 0.012(4) 0.020(4) -0.003(3) 0.000(3) 0.003(3) C108 0.021(3) 0.015(4) 0.028(4) 0.001(3) 0.010(3) -0.002(3) C109 0.019(4) 0.021(5) 0.033(5) -0.003(4) 0.006(3) 0.000(3) C110 0.023(4) 0.028(5) 0.023(4) -0.005(4) -0.007(3) 0.009(3) C111 0.020(3) 0.010(4) 0.021(4) 0.000(3) 0.004(3) 0.003(3) C112 0.030(4) 0.012(4) 0.035(5) 0.001(3) 0.011(3) -0.002(3) C113 0.047(5) 0.034(5) 0.034(4) 0.000(4) 0.011(4) -0.008(4) C114 0.036(4) 0.027(5) 0.024(4) -0.006(4) 0.004(3) 0.002(4) C115 0.052(5) 0.040(6) 0.034(5) 0.002(4) 0.021(4) -0.001(4) C116 0.035(4) 0.014(4) 0.024(4) 0.001(3) 0.016(3) 0.004(3) C117 0.014(3) 0.015(4) 0.035(4) -0.002(3) 0.007(3) -0.003(3) C118 0.017(3) 0.023(5) 0.028(4) -0.002(3) 0.005(3) -0.005(3) C119 0.022(4) 0.033(5) 0.033(5) 0.007(4) -0.003(3) 0.000(4) C120 0.019(4) 0.024(5) 0.045(5) 0.001(4) 0.006(4) 0.009(3) C121 0.025(4) 0.024(5) 0.042(5) -0.005(4) 0.012(4) 0.002(4) C122 0.029(4) 0.016(4) 0.025(4) 0.001(3) 0.005(3) 0.004(3) C123 0.023(4) 0.036(5) 0.026(4) -0.007(4) -0.001(3) -0.001(4) C124 0.038(4) 0.070(7) 0.031(5) -0.008(4) 0.016(4) -0.013(4) C125 0.037(4) 0.040(6) 0.032(5) 0.007(4) 0.016(4) 0.019(4) C126 0.088(7) 0.059(7) 0.044(5) 0.008(5) 0.024(5) 0.022(5) C127 0.080(6) 0.054(7) 0.055(6) 0.003(5) 0.015(5) -0.005(6) C128 0.048(5) 0.045(6) 0.053(6) -0.009(5) 0.012(4) 0.005(5) C129 0.038(5) 0.042(6) 0.074(6) 0.010(5) 0.013(4) 0.004(5) C130 0.046(5) 0.051(7) 0.074(6) 0.003(5) 0.022(4) -0.002(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Bi1 N3 2.255(5) . ? Bi1 N5 2.261(5) . ? Bi1 N1 2.275(5) . ? Bi1 N4 2.751(5) . ? Bi1 N2 2.762(5) . ? Bi2 N7 2.257(5) . ? Bi2 N9 2.266(5) . ? Bi2 N11 2.279(5) . ? Bi2 N10 2.751(5) . ? O1 C129 1.391(8) . ? O1 C128 1.409(9) . ? N1 C11 1.347(7) . ? N1 C1 1.438(7) . ? N2 C11 1.297(7) . ? N2 C12 1.415(7) . ? N3 C32 1.337(7) . ? N3 C22 1.453(7) . ? N4 C32 1.305(7) . ? N4 C33 1.413(8) . ? N5 C53 1.352(7) . ? N5 C54 1.423(8) . ? N6 C53 1.296(7) . ? N6 C43 1.415(7) . ? N7 C74 1.347(7) . ? N7 C64 1.433(7) . ? N8 C74 1.283(7) . ? N8 C75 1.439(7) . ? N9 C95 1.369(7) . ? N9 C85 1.436(7) . ? N10 C95 1.294(7) . ? N10 C96 1.407(8) . ? N11 C116 1.357(7) . ? N11 C106 1.449(7) . ? N12 C116 1.296(7) . ? N12 C117 1.430(7) . ? C1 C2 1.400(8) . ? C1 C6 1.402(8) . ? C2 C3 1.402(8) . ? C2 C7 1.504(8) . ? C3 C4 1.376(9) . ? C4 C5 1.366(9) . ? C5 C6 1.409(8) . ? C6 C9 1.496(8) . ? C7 C8 1.525(8) . ? C9 C10 1.535(8) . ? C12 C17 1.406(8) . ? C12 C13 1.415(7) . ? C13 C14 1.412(8) . ? C13 C18 1.503(8) . ? C14 C15 1.368(9) . ? C15 C16 1.375(8) . ? C16 C17 1.394(8) . ? C17 C20 1.513(8) . ? C18 C19 1.530(9) . ? C20 C21 1.501(8) . ? C22 C23 1.390(8) . ? C22 C27 1.418(8) . ? C23 C24 1.402(8) . ? C23 C28 1.497(8) . ? C24 C25 1.384(8) . ? C25 C26 1.379(8) . ? C26 C27 1.393(8) . ? C27 C30 1.523(8) . ? C28 C29 1.518(9) . ? C30 C31 1.535(7) . ? C33 C34 1.401(8) . ? C33 C38 1.411(8) . ? C34 C35 1.388(9) . ? C34 C39 1.545(9) . ? C35 C36 1.380(9) . ? C36 C37 1.383(9) . ? C37 C38 1.391(8) . ? C38 C41 1.503(8) . ? C39 C40 1.479(8) . ? C41 C42 1.535(8) . ? C43 C48 1.387(8) . ? C43 C44 1.414(8) . ? C44 C45 1.393(8) . ? C44 C49 1.504(8) . ? C45 C46 1.366(8) . ? C46 C47 1.386(8) . ? C47 C48 1.379(8) . ? C48 C51 1.508(8) . ? C49 C50 1.525(8) . ? C51 C52 1.521(9) . ? C54 C55 1.410(8) . ? C54 C59 1.416(8) . ? C55 C56 1.391(8) . ? C55 C60 1.523(8) . ? C56 C57 1.392(8) . ? C57 C58 1.366(9) . ? C58 C59 1.393(9) . ? C59 C62 1.512(9) . ? C60 C61 1.534(8) . ? C62 C63 1.535(8) . ? C64 C65 1.411(8) . ? C64 C69 1.416(8) . ? C65 C66 1.399(9) . ? C65 C70 1.513(8) . ? C66 C67 1.385(9) . ? C67 C68 1.372(8) . ? C68 C69 1.395(8) . ? C69 C72 1.520(8) . ? C70 C71 1.523(8) . ? C72 C73 1.532(8) . ? C75 C76 1.398(8) . ? C75 C80 1.409(8) . ? C76 C77 1.410(9) . ? C76 C81 1.528(9) . ? C77 C78 1.374(10) . ? C78 C79 1.381(10) . ? C79 C80 1.392(9) . ? C80 C83 1.498(9) . ? C81 C82 1.520(9) . ? C83 C84 1.497(9) . ? C85 C90 1.398(8) . ? C85 C86 1.425(8) . ? C86 C87 1.373(9) . ? C86 C93 1.513(8) . ? C87 C88 1.397(9) . ? C88 C89 1.350(9) . ? C89 C90 1.399(8) . ? C90 C91 1.491(8) . ? C91 C92 1.521(9) . ? C93 C94 1.541(7) . ? C96 C97 1.406(8) . ? C96 C101 1.427(9) . ? C97 C98 1.374(9) . ? C97 C102 1.538(9) . ? C98 C99 1.387(9) . ? C99 C100 1.385(8) . ? C100 C101 1.416(8) . ? C101 C104 1.519(8) . ? C102 C103 1.522(8) . ? C104 C105 1.536(8) . ? C106 C111 1.401(8) . ? C106 C107 1.408(8) . ? C107 C108 1.382(8) . ? C107 C112 1.489(8) . ? C108 C109 1.380(8) . ? C109 C110 1.377(9) . ? C110 C111 1.388(8) . ? C111 C114 1.495(8) . ? C112 C113 1.539(8) . ? C114 C115 1.530(9) . ? C117 C122 1.402(8) . ? C117 C118 1.409(8) . ? C118 C119 1.404(8) . ? C118 C123 1.506(8) . ? C119 C120 1.355(9) . ? C120 C121 1.378(8) . ? C121 C122 1.386(8) . ? C122 C125 1.527(8) . ? C123 C124 1.523(9) . ? C125 C126 1.462(9) . ? C127 C128 1.497(10) . ? C129 C130 1.480(10) . ? 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 N3 Bi1 N5 95.48(17) . . ? N3 Bi1 N1 95.10(18) . . ? N5 Bi1 N1 95.85(17) . . ? N3 Bi1 N4 52.92(16) . . ? N5 Bi1 N4 84.37(16) . . ? N1 Bi1 N4 147.71(16) . . ? N3 Bi1 N2 84.71(16) . . ? N5 Bi1 N2 148.32(16) . . ? N1 Bi1 N2 52.74(15) . . ? N4 Bi1 N2 119.18(14) . . ? N7 Bi2 N9 96.01(17) . . ? N7 Bi2 N11 96.49(17) . . ? N9 Bi2 N11 94.27(18) . . ? N7 Bi2 N10 82.82(16) . . ? N9 Bi2 N10 53.07(17) . . ? N11 Bi2 N10 146.77(16) . . ? C129 O1 C128 114.4(6) . . ? C11 N1 C1 115.8(5) . . ? C11 N1 Bi1 103.8(4) . . ? C1 N1 Bi1 133.3(4) . . ? C11 N2 C12 119.3(5) . . ? C11 N2 Bi1 83.1(4) . . ? C12 N2 Bi1 156.6(4) . . ? C32 N3 C22 114.6(5) . . ? C32 N3 Bi1 104.4(4) . . ? C22 N3 Bi1 134.7(4) . . ? C32 N4 C33 121.2(5) . . ? C32 N4 Bi1 82.8(4) . . ? C33 N4 Bi1 155.0(4) . . ? C53 N5 C54 116.2(5) . . ? C53 N5 Bi1 104.6(4) . . ? C54 N5 Bi1 131.7(4) . . ? C53 N6 C43 120.2(5) . . ? C74 N7 C64 114.9(5) . . ? C74 N7 Bi2 105.2(4) . . ? C64 N7 Bi2 132.5(4) . . ? C74 N8 C75 117.5(5) . . ? C95 N9 C85 115.3(5) . . ? C95 N9 Bi2 103.9(4) . . ? C85 N9 Bi2 134.3(4) . . ? C95 N10 C96 118.1(6) . . ? C95 N10 Bi2 84.0(4) . . ? C96 N10 Bi2 156.7(4) . . ? C116 N11 C106 114.6(5) . . ? C116 N11 Bi2 104.5(4) . . ? C106 N11 Bi2 134.2(4) . . ? C116 N12 C117 118.5(5) . . ? C2 C1 C6 121.4(6) . . ? C2 C1 N1 120.0(5) . . ? C6 C1 N1 118.5(6) . . ? C1 C2 C3 117.6(6) . . ? C1 C2 C7 120.6(5) . . ? C3 C2 C7 121.7(6) . . ? C4 C3 C2 121.7(7) . . ? C5 C4 C3 120.0(6) . . ? C4 C5 C6 121.0(6) . . ? C1 C6 C5 118.1(6) . . ? C1 C6 C9 121.8(5) . . ? C5 C6 C9 119.8(6) . . ? C2 C7 C8 117.2(5) . . ? C6 C9 C10 112.0(6) . . ? N2 C11 N1 119.2(6) . . ? C17 C12 C13 121.1(5) . . ? C17 C12 N2 123.0(5) . . ? C13 C12 N2 115.6(5) . . ? C14 C13 C12 117.4(6) . . ? C14 C13 C18 120.8(5) . . ? C12 C13 C18 121.8(5) . . ? C15 C14 C13 121.7(6) . . ? C14 C15 C16 119.7(6) . . ? C15 C16 C17 122.0(6) . . ? C16 C17 C12 118.0(5) . . ? C16 C17 C20 120.3(6) . . ? C12 C17 C20 121.7(5) . . ? C13 C18 C19 112.6(6) . . ? C21 C20 C17 116.1(5) . . ? C23 C22 C27 121.5(6) . . ? C23 C22 N3 118.9(5) . . ? C27 C22 N3 119.6(5) . . ? C22 C23 C24 117.8(6) . . ? C22 C23 C28 121.4(6) . . ? C24 C23 C28 120.4(6) . . ? C25 C24 C23 121.7(6) . . ? C26 C25 C24 119.6(6) . . ? C25 C26 C27 121.2(6) . . ? C26 C27 C22 118.1(6) . . ? C26 C27 C30 121.7(5) . . ? C22 C27 C30 120.2(5) . . ? C23 C28 C29 111.1(5) . . ? C27 C30 C31 115.3(5) . . ? N4 C32 N3 118.8(6) . . ? C34 C33 C38 120.9(6) . . ? C34 C33 N4 116.5(6) . . ? C38 C33 N4 122.4(6) . . ? C35 C34 C33 119.4(7) . . ? C35 C34 C39 122.4(6) . . ? C33 C34 C39 118.2(6) . . ? C36 C35 C34 120.5(7) . . ? C35 C36 C37 119.7(7) . . ? C36 C37 C38 122.1(6) . . ? C37 C38 C33 117.3(6) . . ? C37 C38 C41 120.6(6) . . ? C33 C38 C41 122.1(6) . . ? C40 C39 C34 115.4(6) . . ? C38 C41 C42 115.7(6) . . ? C48 C43 C44 120.9(6) . . ? C48 C43 N6 117.0(5) . . ? C44 C43 N6 122.1(6) . . ? C45 C44 C43 117.8(6) . . ? C45 C44 C49 120.2(6) . . ? C43 C44 C49 121.9(6) . . ? C46 C45 C44 121.2(6) . . ? C45 C46 C47 120.3(6) . . ? C48 C47 C46 120.5(6) . . ? C47 C48 C43 119.3(6) . . ? C47 C48 C51 119.1(6) . . ? C43 C48 C51 121.5(6) . . ? C44 C49 C50 116.8(6) . . ? C48 C51 C52 113.1(6) . . ? N6 C53 N5 121.5(6) . . ? C55 C54 C59 120.0(6) . . ? C55 C54 N5 120.2(6) . . ? C59 C54 N5 119.8(6) . . ? C56 C55 C54 118.8(6) . . ? C56 C55 C60 121.0(6) . . ? C54 C55 C60 120.1(6) . . ? C55 C56 C57 120.8(7) . . ? C58 C57 C56 120.2(7) . . ? C57 C58 C59 121.3(7) . . ? C58 C59 C54 118.7(6) . . ? C58 C59 C62 121.3(6) . . ? C54 C59 C62 119.7(6) . . ? C55 C60 C61 116.0(5) . . ? C59 C62 C63 110.8(5) . . ? C65 C64 C69 120.0(6) . . ? C65 C64 N7 118.4(6) . . ? C69 C64 N7 121.5(5) . . ? C66 C65 C64 118.9(6) . . ? C66 C65 C70 121.1(6) . . ? C64 C65 C70 119.9(6) . . ? C67 C66 C65 120.8(6) . . ? C68 C67 C66 120.0(6) . . ? C67 C68 C69 121.6(6) . . ? C68 C69 C64 118.5(6) . . ? C68 C69 C72 121.4(6) . . ? C64 C69 C72 120.0(6) . . ? C65 C70 C71 112.7(5) . . ? C69 C72 C73 115.9(5) . . ? N8 C74 N7 121.2(6) . . ? C76 C75 C80 122.3(6) . . ? C76 C75 N8 116.5(6) . . ? C80 C75 N8 121.2(6) . . ? C75 C76 C77 117.6(7) . . ? C75 C76 C81 121.7(6) . . ? C77 C76 C81 120.5(7) . . ? C78 C77 C76 120.2(7) . . ? C77 C78 C79 121.7(7) . . ? C78 C79 C80 120.2(7) . . ? C79 C80 C75 117.9(7) . . ? C79 C80 C83 121.4(7) . . ? C75 C80 C83 120.7(6) . . ? C82 C81 C76 110.8(7) . . ? C84 C83 C80 117.1(6) . . ? C90 C85 C86 121.1(6) . . ? C90 C85 N9 119.5(5) . . ? C86 C85 N9 119.2(5) . . ? C87 C86 C85 117.8(6) . . ? C87 C86 C93 122.3(6) . . ? C85 C86 C93 119.8(5) . . ? C86 C87 C88 120.9(6) . . ? C89 C88 C87 120.8(7) . . ? C88 C89 C90 121.2(6) . . ? C85 C90 C89 118.0(6) . . ? C85 C90 C91 122.2(6) . . ? C89 C90 C91 119.6(6) . . ? C90 C91 C92 112.6(5) . . ? C86 C93 C94 116.3(5) . . ? N10 C95 N9 118.0(6) . . ? C97 C96 N10 117.4(6) . . ? C97 C96 C101 119.9(6) . . ? N10 C96 C101 122.5(6) . . ? C98 C97 C96 119.7(7) . . ? C98 C97 C102 120.4(6) . . ? C96 C97 C102 119.9(6) . . ? C97 C98 C99 122.4(7) . . ? C100 C99 C98 118.1(7) . . ? C99 C100 C101 122.5(6) . . ? C100 C101 C96 117.2(6) . . ? C100 C101 C104 121.3(6) . . ? C96 C101 C104 121.4(6) . . ? C103 C102 C97 114.1(6) . . ? C101 C104 C105 115.2(5) . . ? C111 C106 C107 122.3(6) . . ? C111 C106 N11 118.3(5) . . ? C107 C106 N11 119.2(5) . . ? C108 C107 C106 116.9(5) . . ? C108 C107 C112 122.5(6) . . ? C106 C107 C112 120.6(5) . . ? C109 C108 C107 122.5(6) . . ? C110 C109 C108 119.0(6) . . ? C109 C110 C111 121.9(6) . . ? C110 C111 C106 117.4(6) . . ? C110 C111 C114 120.2(6) . . ? C106 C111 C114 122.2(5) . . ? C107 C112 C113 116.4(5) . . ? C111 C114 C115 112.9(6) . . ? N12 C116 N11 120.2(6) . . ? C122 C117 C118 120.0(5) . . ? C122 C117 N12 123.1(5) . . ? C118 C117 N12 116.8(6) . . ? C119 C118 C117 118.4(6) . . ? C119 C118 C123 120.3(6) . . ? C117 C118 C123 121.2(5) . . ? C120 C119 C118 121.1(6) . . ? C119 C120 C121 120.5(6) . . ? C120 C121 C122 120.9(6) . . ? C121 C122 C117 119.1(6) . . ? C121 C122 C125 119.1(6) . . ? C117 C122 C125 121.8(5) . . ? C118 C123 C124 112.1(6) . . ? C126 C125 C122 117.3(6) . . ? O1 C128 C127 109.1(6) . . ? O1 C129 C130 111.1(6) . . ? _diffrn_measured_fraction_theta_max 0.807 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.807 _refine_diff_density_max 0.948 _refine_diff_density_min -0.717 _refine_diff_density_rms 0.117 # Attachment '3c.CIF' data_3c _database_code_depnum_ccdc_archive 'CCDC 643180' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C57 H69 Bi N6' _chemical_formula_sum 'C57 H69 Bi N6' _chemical_formula_weight 1047.16 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' N N 0.0061 0.0033 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 25.1830(2) _cell_length_b 12.6656(2) _cell_length_c 16.4914(4) _cell_angle_alpha 90.00 _cell_angle_beta 104.166(1) _cell_angle_gamma 90.00 _cell_volume 5100.11(15) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.364 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2144 _exptl_absorpt_coefficient_mu 3.499 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5212 _exptl_absorpt_correction_T_max 0.6588 _exptl_absorpt_process_details SORTAV _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius KAPPA CCD' _diffrn_measurement_method '1 deg frames in phi and omega' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 59354 _diffrn_reflns_av_R_equivalents 0.0678 _diffrn_reflns_av_sigmaI/netI 0.0447 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 27.50 _reflns_number_total 11706 _reflns_number_gt 9737 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Burker ASX 2004)' _computing_cell_refinement 'DENZO-SMN (Otwinoski and Minor 1997)' _computing_data_reduction 'DENZO-SMN (Otwinoski and Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0527P)^2^+2.0807P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11706 _refine_ls_number_parameters 595 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0471 _refine_ls_R_factor_gt 0.0340 _refine_ls_wR_factor_ref 0.0879 _refine_ls_wR_factor_gt 0.0826 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 _atom_site_disorder_assembly _atom_site_disorder_group Bi1 Bi 0.742923(5) 0.932082(9) 0.859318(7) 0.01251(5) Uani 1 1 d . . . N1 N 0.78998(12) 1.0960(2) 0.86444(18) 0.0167(6) Uani 1 1 d . . . N2 N 0.69869(11) 1.1131(2) 0.80026(17) 0.0160(6) Uani 1 1 d . . . N3 N 0.81704(11) 0.8613(2) 0.96199(17) 0.0161(6) Uani 1 1 d . . . N4 N 0.75135(11) 0.7389(2) 0.91135(17) 0.0156(6) Uani 1 1 d . . . N5 N 0.76519(11) 0.8834(2) 0.74376(16) 0.0153(6) Uani 1 1 d . . . N6 N 0.67339(11) 0.8478(2) 0.72101(16) 0.0166(6) Uani 1 1 d . . . C1 C 0.83507(14) 1.1458(2) 0.9213(2) 0.0177(7) Uani 1 1 d . . . C2 C 0.83011(14) 1.1797(2) 1.0001(2) 0.0183(7) Uani 1 1 d . . . C3 C 0.87480(15) 1.2291(3) 1.0536(2) 0.0215(8) Uani 1 1 d . . . H3 H 0.8714 1.2525 1.1068 0.026 Uiso 1 1 calc R . . C4 C 0.92407(15) 1.2452(3) 1.0317(2) 0.0221(8) Uani 1 1 d . . . C5 C 0.92769(15) 1.2121(3) 0.9529(2) 0.0228(8) Uani 1 1 d . . . H5 H 0.9609 1.2233 0.9367 0.027 Uiso 1 1 calc R . . C6 C 0.88405(14) 1.1627(3) 0.8968(2) 0.0192(7) Uani 1 1 d . . . C7 C 0.77801(14) 1.1663(3) 1.0283(2) 0.0202(7) Uani 1 1 d . . . H7A H 0.7864 1.1667 1.0896 0.030 Uiso 1 1 calc R . . H7B H 0.7608 1.0991 1.0073 0.030 Uiso 1 1 calc R . . H7C H 0.7529 1.2245 1.0064 0.030 Uiso 1 1 calc R . . C8 C 0.97176(16) 1.2951(3) 1.0925(3) 0.0346(9) Uani 1 1 d . . . H8A H 0.9939 1.2401 1.1266 0.052 Uiso 1 1 calc R . . H8B H 0.9582 1.3441 1.1288 0.052 Uiso 1 1 calc R . . H8C H 0.9943 1.3338 1.0616 0.052 Uiso 1 1 calc R . . C9 C 0.88892(16) 1.1324(3) 0.8104(2) 0.0289(9) Uani 1 1 d . . . H9A H 0.9259 1.1490 0.8048 0.043 Uiso 1 1 calc R . . H9B H 0.8619 1.1720 0.7685 0.043 Uiso 1 1 calc R . . H9C H 0.8821 1.0566 0.8019 0.043 Uiso 1 1 calc R . . C10 C 0.74505(14) 1.1562(3) 0.8377(2) 0.0186(7) Uani 1 1 d . . . H10 H 0.7472 1.2304 0.8462 0.022 Uiso 1 1 calc R . . C11 C 0.65050(13) 1.1755(3) 0.7779(2) 0.0166(7) Uani 1 1 d . . . C12 C 0.64641(15) 1.2669(3) 0.7284(2) 0.0205(7) Uani 1 1 d . . . C13 C 0.59668(15) 1.3214(3) 0.7105(2) 0.0250(8) Uani 1 1 d . . . H13 H 0.5939 1.3844 0.6785 0.030 Uiso 1 1 calc R . . C14 C 0.55140(15) 1.2887(3) 0.7368(2) 0.0254(8) Uani 1 1 d . . . C15 C 0.55588(15) 1.1959(3) 0.7836(2) 0.0242(8) Uani 1 1 d . . . H15 H 0.5250 1.1706 0.8012 0.029 Uiso 1 1 calc R . . C16 C 0.60486(14) 1.1396(3) 0.8050(2) 0.0193(7) Uani 1 1 d . . . C17 C 0.69255(16) 1.3061(3) 0.6930(2) 0.0275(8) Uani 1 1 d . . . H17A H 0.6776 1.3486 0.6430 0.041 Uiso 1 1 calc R . . H17B H 0.7126 1.2458 0.6782 0.041 Uiso 1 1 calc R . . H17C H 0.7174 1.3496 0.7349 0.041 Uiso 1 1 calc R . . C18 C 0.49835(17) 1.3502(4) 0.7158(3) 0.0419(11) Uani 1 1 d . . . H18A H 0.5032 1.4168 0.7470 0.063 Uiso 1 1 calc R . . H18B H 0.4695 1.3086 0.7311 0.063 Uiso 1 1 calc R . . H18C H 0.4880 1.3651 0.6556 0.063 Uiso 1 1 calc R . . C19 C 0.60924(15) 1.0409(3) 0.8578(2) 0.0251(8) Uani 1 1 d . . . H19A H 0.6167 0.9801 0.8255 0.038 Uiso 1 1 calc R . . H19B H 0.5747 1.0296 0.8740 0.038 Uiso 1 1 calc R . . H19C H 0.6391 1.0490 0.9081 0.038 Uiso 1 1 calc R . . C20 C 0.85190(14) 0.9077(3) 1.0352(2) 0.0182(7) Uani 1 1 d . . . C21 C 0.90671(15) 0.9278(2) 1.0346(2) 0.0213(8) Uani 1 1 d . . . C22 C 0.94092(15) 0.9736(3) 1.1050(2) 0.0273(8) Uani 1 1 d . . . H22 H 0.9782 0.9858 1.1056 0.033 Uiso 1 1 calc R . . C23 C 0.92205(16) 1.0020(3) 1.1745(2) 0.0285(9) Uani 1 1 d . . . C24 C 0.86784(16) 0.9828(3) 1.1725(2) 0.0263(8) Uani 1 1 d . . . H24 H 0.8543 1.0025 1.2193 0.032 Uiso 1 1 calc R . . C25 C 0.83234(16) 0.9355(2) 1.1042(2) 0.0207(8) Uani 1 1 d . . . C26 C 0.92826(16) 0.8989(3) 0.9604(2) 0.0293(9) Uani 1 1 d . . . H26A H 0.9667 0.9205 0.9705 0.044 Uiso 1 1 calc R . . H26B H 0.9067 0.9348 0.9106 0.044 Uiso 1 1 calc R . . H26C H 0.9255 0.8223 0.9518 0.044 Uiso 1 1 calc R . . C27 C 0.9596(2) 1.0543(4) 1.2500(3) 0.0478(13) Uani 1 1 d . . . H27A H 0.9514 1.1300 1.2496 0.072 Uiso 1 1 calc R . . H27B H 0.9978 1.0444 1.2478 0.072 Uiso 1 1 calc R . . H27C H 0.9538 1.0224 1.3013 0.072 Uiso 1 1 calc R . . C28 C 0.77386(16) 0.9140(3) 1.1081(2) 0.0253(8) Uani 1 1 d . . . H28A H 0.7491 0.9284 1.0534 0.038 Uiso 1 1 calc R . . H28B H 0.7644 0.9598 1.1504 0.038 Uiso 1 1 calc R . . H28C H 0.7703 0.8400 1.1232 0.038 Uiso 1 1 calc R . . C29 C 0.79225(13) 0.7691(2) 0.9706(2) 0.0160(7) Uani 1 1 d . . . H29 H 0.8046 0.7271 1.0192 0.019 Uiso 1 1 calc R . . C30 C 0.72256(14) 0.6446(3) 0.92130(19) 0.0172(7) Uani 1 1 d . . . C31 C 0.67013(14) 0.6542(3) 0.9354(2) 0.0204(7) Uani 1 1 d . . . C32 C 0.64010(16) 0.5644(3) 0.9412(2) 0.0232(8) Uani 1 1 d . . . H32 H 0.6046 0.5716 0.9507 0.028 Uiso 1 1 calc R . . C33 C 0.66051(16) 0.4636(3) 0.9335(2) 0.0236(8) Uani 1 1 d . . . C34 C 0.71171(17) 0.4559(3) 0.9169(2) 0.0232(8) Uani 1 1 d . . . H34 H 0.7257 0.3878 0.9101 0.028 Uiso 1 1 calc R . . C35 C 0.74343(16) 0.5435(3) 0.9099(2) 0.0213(8) Uani 1 1 d . . . C36 C 0.64573(16) 0.7617(3) 0.9424(3) 0.0274(9) Uani 1 1 d . . . H36A H 0.6104 0.7535 0.9566 0.041 Uiso 1 1 calc R . . H36B H 0.6404 0.7989 0.8889 0.041 Uiso 1 1 calc R . . H36C H 0.6706 0.8024 0.9863 0.041 Uiso 1 1 calc R . . C37 C 0.62888(19) 0.3656(3) 0.9449(3) 0.0345(10) Uani 1 1 d . . . H37A H 0.6393 0.3073 0.9129 0.052 Uiso 1 1 calc R . . H37B H 0.5895 0.3792 0.9249 0.052 Uiso 1 1 calc R . . H37C H 0.6373 0.3467 1.0043 0.052 Uiso 1 1 calc R . . C38 C 0.79699(16) 0.5292(3) 0.8865(2) 0.0248(8) Uani 1 1 d . . . H38A H 0.8105 0.4573 0.9006 0.037 Uiso 1 1 calc R . . H38B H 0.8237 0.5801 0.9174 0.037 Uiso 1 1 calc R . . H38C H 0.7917 0.5409 0.8263 0.037 Uiso 1 1 calc R . . C39 C 0.81119(14) 0.8950(3) 0.7070(2) 0.0176(7) Uani 1 1 d . . . C40 C 0.85343(13) 0.8206(3) 0.7256(2) 0.0170(7) Uani 1 1 d . . . C41 C 0.89399(14) 0.8246(3) 0.6809(2) 0.0216(7) Uani 1 1 d . . . H41 H 0.9225 0.7736 0.6924 0.026 Uiso 1 1 calc R . . C42 C 0.89377(15) 0.9004(3) 0.6204(2) 0.0232(8) Uani 1 1 d . . . C43 C 0.85250(15) 0.9769(3) 0.6068(2) 0.0228(8) Uani 1 1 d . . . H43 H 0.8529 1.0316 0.5675 0.027 Uiso 1 1 calc R . . C44 C 0.81092(14) 0.9755(3) 0.6488(2) 0.0190(7) Uani 1 1 d . . . C45 C 0.85361(15) 0.7354(3) 0.7885(2) 0.0235(8) Uani 1 1 d . . . H45A H 0.8504 0.7672 0.8414 0.035 Uiso 1 1 calc R . . H45B H 0.8879 0.6955 0.7978 0.035 Uiso 1 1 calc R . . H45C H 0.8226 0.6878 0.7677 0.035 Uiso 1 1 calc R . . C46 C 0.93471(17) 0.8974(4) 0.5673(3) 0.0337(9) Uani 1 1 d . . . H46A H 0.9682 0.8623 0.5982 0.051 Uiso 1 1 calc R . . H46B H 0.9433 0.9697 0.5535 0.051 Uiso 1 1 calc R . . H46C H 0.9192 0.8584 0.5156 0.051 Uiso 1 1 calc R . . C47 C 0.76650(17) 1.0579(3) 0.6322(2) 0.0264(9) Uani 1 1 d . . . H47A H 0.7787 1.1195 0.6057 0.040 Uiso 1 1 calc R . . H47B H 0.7586 1.0791 0.6852 0.040 Uiso 1 1 calc R . . H47C H 0.7333 1.0286 0.5951 0.040 Uiso 1 1 calc R . . C48 C 0.71722(14) 0.8499(2) 0.6939(2) 0.0164(7) Uani 1 1 d . . . H48 H 0.7158 0.8277 0.6384 0.020 Uiso 1 1 calc R . . C49 C 0.62484(13) 0.8047(3) 0.6677(2) 0.0170(7) Uani 1 1 d . . . C50 C 0.61585(14) 0.6956(3) 0.6627(2) 0.0185(7) Uani 1 1 d . . . C51 C 0.56778(14) 0.6575(3) 0.6104(2) 0.0206(7) Uani 1 1 d . . . H51 H 0.5618 0.5834 0.6072 0.025 Uiso 1 1 calc R . . C52 C 0.52806(14) 0.7235(3) 0.5625(2) 0.0229(8) Uani 1 1 d . . . C53 C 0.53807(14) 0.8320(3) 0.5691(2) 0.0211(7) Uani 1 1 d . . . H53 H 0.5115 0.8787 0.5371 0.025 Uiso 1 1 calc R . . C54 C 0.58512(14) 0.8742(3) 0.6204(2) 0.0186(7) Uani 1 1 d . . . C55 C 0.65718(16) 0.6187(3) 0.7128(2) 0.0266(8) Uani 1 1 d . . . H55A H 0.6430 0.5891 0.7583 0.040 Uiso 1 1 calc R . . H55B H 0.6917 0.6558 0.7364 0.040 Uiso 1 1 calc R . . H55C H 0.6636 0.5616 0.6763 0.040 Uiso 1 1 calc R . . C56 C 0.47638(15) 0.6804(3) 0.5064(2) 0.0302(9) Uani 1 1 d . . . H56A H 0.4468 0.6828 0.5356 0.045 Uiso 1 1 calc R . . H56B H 0.4824 0.6072 0.4916 0.045 Uiso 1 1 calc R . . H56C H 0.4662 0.7232 0.4554 0.045 Uiso 1 1 calc R . . C57 C 0.59378(16) 0.9919(3) 0.6251(2) 0.0264(8) Uani 1 1 d . . . H57A H 0.5658 1.0263 0.5812 0.040 Uiso 1 1 calc R . . H57B H 0.6302 1.0085 0.6171 0.040 Uiso 1 1 calc R . . H57C H 0.5910 1.0176 0.6799 0.040 Uiso 1 1 calc R . . 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 0.01356(7) 0.01006(7) 0.01457(7) -0.00042(4) 0.00471(5) 0.00008(5) N1 0.0161(14) 0.0132(13) 0.0218(15) 0.0008(12) 0.0065(12) -0.0004(12) N2 0.0156(14) 0.0130(13) 0.0202(14) 0.0011(12) 0.0060(11) 0.0026(12) N3 0.0135(14) 0.0134(14) 0.0213(14) 0.0000(11) 0.0043(11) -0.0018(11) N4 0.0162(14) 0.0131(14) 0.0176(14) 0.0020(11) 0.0045(11) -0.0003(11) N5 0.0142(14) 0.0170(14) 0.0153(13) -0.0019(11) 0.0047(11) -0.0009(12) N6 0.0142(14) 0.0195(14) 0.0154(14) -0.0032(12) 0.0022(11) -0.0025(12) C1 0.0184(17) 0.0121(16) 0.0218(17) -0.0009(13) 0.0033(14) -0.0013(14) C2 0.0222(18) 0.0110(16) 0.0228(17) 0.0001(13) 0.0077(14) 0.0010(14) C3 0.0257(19) 0.0155(17) 0.0223(18) -0.0025(14) 0.0042(15) 0.0032(15) C4 0.0195(18) 0.0172(17) 0.028(2) -0.0024(15) 0.0027(15) -0.0035(15) C5 0.0198(18) 0.0224(18) 0.0278(19) -0.0003(16) 0.0086(15) -0.0050(15) C6 0.0204(18) 0.0173(17) 0.0210(17) -0.0002(14) 0.0072(14) -0.0008(14) C7 0.0209(18) 0.0173(17) 0.0229(18) -0.0041(14) 0.0064(14) 0.0019(14) C8 0.026(2) 0.038(2) 0.038(2) -0.0144(19) 0.0048(17) -0.0051(19) C9 0.024(2) 0.036(2) 0.029(2) -0.0032(17) 0.0123(16) -0.0075(17) C10 0.0232(19) 0.0142(17) 0.0204(16) 0.0032(14) 0.0092(14) -0.0023(14) C11 0.0159(16) 0.0138(16) 0.0191(16) -0.0048(13) 0.0021(13) 0.0020(13) C12 0.0238(19) 0.0176(17) 0.0205(18) -0.0035(14) 0.0064(15) 0.0032(15) C13 0.030(2) 0.0207(19) 0.0218(18) 0.0012(15) 0.0018(15) 0.0082(16) C14 0.0208(19) 0.031(2) 0.0227(18) -0.0040(16) 0.0019(14) 0.0109(17) C15 0.0193(18) 0.029(2) 0.0259(18) -0.0073(16) 0.0081(15) -0.0008(16) C16 0.0208(18) 0.0175(17) 0.0191(17) -0.0061(14) 0.0037(14) 0.0004(14) C17 0.030(2) 0.0222(19) 0.032(2) 0.0080(16) 0.0110(17) 0.0048(17) C18 0.027(2) 0.056(3) 0.042(2) 0.010(2) 0.0087(19) 0.024(2) C19 0.0190(19) 0.0216(18) 0.037(2) 0.0004(16) 0.0116(16) -0.0020(15) C20 0.0198(18) 0.0125(16) 0.0212(18) 0.0024(14) 0.0026(14) 0.0000(14) C21 0.0206(18) 0.0158(18) 0.027(2) 0.0031(14) 0.0047(15) -0.0020(14) C22 0.0179(19) 0.0254(19) 0.035(2) 0.0072(17) -0.0014(16) -0.0054(16) C23 0.031(2) 0.026(2) 0.0229(19) 0.0049(16) -0.0054(16) -0.0086(17) C24 0.037(2) 0.0218(19) 0.0202(18) 0.0001(15) 0.0069(16) -0.0088(17) C25 0.026(2) 0.0146(17) 0.0210(18) 0.0041(13) 0.0049(15) -0.0028(14) C26 0.0195(19) 0.035(2) 0.035(2) -0.0029(18) 0.0100(16) -0.0012(17) C27 0.051(3) 0.056(3) 0.029(2) -0.008(2) -0.006(2) -0.024(2) C28 0.028(2) 0.0251(19) 0.025(2) -0.0006(15) 0.0108(16) -0.0035(16) C29 0.0186(17) 0.0115(16) 0.0189(17) 0.0055(13) 0.0067(14) 0.0063(13) C30 0.0241(18) 0.0135(16) 0.0132(15) -0.0001(13) 0.0028(13) -0.0032(14) C31 0.0220(18) 0.0182(17) 0.0220(18) 0.0024(14) 0.0073(14) -0.0007(15) C32 0.0242(19) 0.0224(19) 0.0231(19) 0.0007(14) 0.0063(15) -0.0044(15) C33 0.034(2) 0.0187(17) 0.0177(17) -0.0014(15) 0.0053(15) -0.0099(16) C34 0.039(2) 0.0115(16) 0.0218(18) -0.0025(14) 0.0124(17) -0.0007(16) C35 0.033(2) 0.0130(16) 0.0182(17) 0.0006(14) 0.0069(15) 0.0005(15) C36 0.025(2) 0.0184(18) 0.044(2) 0.0045(17) 0.0180(18) 0.0025(16) C37 0.049(3) 0.023(2) 0.036(2) -0.0048(17) 0.018(2) -0.0151(19) C38 0.034(2) 0.0168(17) 0.0262(19) 0.0015(15) 0.0125(16) 0.0038(16) C39 0.0206(18) 0.0146(16) 0.0188(17) -0.0065(14) 0.0072(14) -0.0040(14) C40 0.0173(16) 0.0153(17) 0.0170(16) -0.0041(13) 0.0015(13) -0.0015(14) C41 0.0160(17) 0.0248(19) 0.0235(18) -0.0085(15) 0.0043(14) 0.0009(15) C42 0.0170(18) 0.0285(19) 0.0258(19) -0.0114(16) 0.0085(15) -0.0115(16) C43 0.030(2) 0.0215(18) 0.0183(17) -0.0046(15) 0.0075(15) -0.0091(16) C44 0.0220(18) 0.0178(17) 0.0177(17) -0.0051(14) 0.0060(14) -0.0016(15) C45 0.0240(19) 0.0211(18) 0.0252(19) -0.0010(15) 0.0056(15) 0.0056(15) C46 0.028(2) 0.044(2) 0.033(2) -0.011(2) 0.0151(18) -0.008(2) C47 0.037(2) 0.022(2) 0.022(2) 0.0051(14) 0.0114(17) 0.0081(16) C48 0.0225(18) 0.0088(15) 0.0169(16) -0.0016(13) 0.0031(13) -0.0003(13) C49 0.0154(16) 0.0202(17) 0.0170(16) -0.0029(14) 0.0069(13) -0.0010(14) C50 0.0199(17) 0.0200(17) 0.0174(16) -0.0032(14) 0.0081(13) -0.0040(15) C51 0.0226(18) 0.0210(18) 0.0199(17) -0.0033(14) 0.0086(14) -0.0046(15) C52 0.0198(18) 0.029(2) 0.0212(18) -0.0054(15) 0.0075(14) -0.0050(15) C53 0.0180(17) 0.0260(18) 0.0183(17) -0.0019(15) 0.0027(14) 0.0036(15) C54 0.0181(17) 0.0220(18) 0.0162(16) -0.0029(14) 0.0055(13) 0.0009(14) C55 0.027(2) 0.024(2) 0.028(2) -0.0006(16) 0.0033(16) 0.0011(16) C56 0.023(2) 0.036(2) 0.029(2) -0.0050(17) 0.0026(16) -0.0041(17) C57 0.033(2) 0.0225(19) 0.0215(19) -0.0022(15) 0.0026(16) 0.0003(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Bi1 N5 2.202(3) . ? Bi1 N3 2.368(3) . ? Bi1 N1 2.382(3) . ? Bi1 N4 2.585(3) . ? Bi1 N2 2.629(3) . ? Bi1 N6 2.730(3) . ? Bi1 C29 2.838(3) . ? Bi1 C48 2.843(3) . ? Bi1 C10 2.863(3) . ? N1 C10 1.346(4) . ? N1 C1 1.430(4) . ? N2 C10 1.300(4) . ? N2 C11 1.420(4) . ? N3 C29 1.348(4) . ? N3 C20 1.433(4) . ? N4 C29 1.292(4) . ? N4 C30 1.428(4) . ? N5 C48 1.353(4) . ? N5 C39 1.440(4) . ? N6 C48 1.289(4) . ? N6 C49 1.428(4) . ? C1 C2 1.404(5) . ? C1 C6 1.405(5) . ? C2 C3 1.396(5) . ? C2 C7 1.505(5) . ? C3 C4 1.389(5) . ? C3 H3 0.9500 . ? C4 C5 1.389(5) . ? C4 C8 1.503(5) . ? C5 C6 1.399(5) . ? C5 H5 0.9500 . ? C6 C9 1.508(5) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10 0.9500 . ? C11 C12 1.405(5) . ? C11 C16 1.407(5) . ? C12 C13 1.397(5) . ? C12 C17 1.507(5) . ? C13 C14 1.379(5) . ? C13 H13 0.9500 . ? C14 C15 1.396(5) . ? C14 C18 1.512(5) . ? C15 C16 1.393(5) . ? C15 H15 0.9500 . ? C16 C19 1.512(5) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C25 1.391(5) . ? C20 C21 1.406(5) . ? C21 C22 1.391(5) . ? C21 C26 1.501(5) . ? C22 C23 1.392(5) . ? C22 H22 0.9500 . ? C23 C24 1.379(5) . ? C23 C27 1.519(5) . ? C24 C25 1.391(5) . ? C24 H24 0.9500 . ? C25 C28 1.515(5) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29 0.9500 . ? C30 C31 1.401(5) . ? C30 C35 1.413(5) . ? C31 C32 1.382(5) . ? C31 C36 1.509(5) . ? C32 C33 1.393(5) . ? C32 H32 0.9500 . ? C33 C34 1.385(5) . ? C33 C37 1.512(5) . ? C34 C35 1.389(5) . ? C34 H34 0.9500 . ? C35 C38 1.502(5) . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? C39 C40 1.397(5) . ? C39 C44 1.400(5) . ? C40 C41 1.399(5) . ? C40 C45 1.497(5) . ? C41 C42 1.384(5) . ? C41 H41 0.9500 . ? C42 C43 1.398(5) . ? C42 C46 1.508(5) . ? C43 C44 1.390(5) . ? C43 H43 0.9500 . ? C44 C47 1.504(5) . ? C45 H45A 0.9800 . ? C45 H45B 0.9800 . ? C45 H45C 0.9800 . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? C47 H47A 0.9800 . ? C47 H47B 0.9800 . ? C47 H47C 0.9800 . ? C48 H48 0.9500 . ? C49 C50 1.400(5) . ? C49 C54 1.415(5) . ? C50 C51 1.390(5) . ? C50 C55 1.514(5) . ? C51 C52 1.392(5) . ? C51 H51 0.9500 . ? C52 C53 1.396(5) . ? C52 C56 1.503(5) . ? C53 C54 1.384(5) . ? C53 H53 0.9500 . ? C54 C57 1.506(5) . ? C55 H55A 0.9800 . ? C55 H55B 0.9800 . ? C55 H55C 0.9800 . ? C56 H56A 0.9800 . ? C56 H56B 0.9800 . ? C56 H56C 0.9800 . ? C57 H57A 0.9800 . ? C57 H57B 0.9800 . ? C57 H57C 0.9800 . ? 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 N5 Bi1 N3 100.93(10) . . ? N5 Bi1 N1 92.59(10) . . ? N3 Bi1 N1 90.36(9) . . ? N5 Bi1 N4 90.25(9) . . ? N3 Bi1 N4 54.41(9) . . ? N1 Bi1 N4 144.47(9) . . ? N5 Bi1 N2 95.64(9) . . ? N3 Bi1 N2 141.55(9) . . ? N1 Bi1 N2 54.20(9) . . ? N4 Bi1 N2 160.28(9) . . ? N5 Bi1 N6 54.17(9) . . ? N3 Bi1 N6 132.97(9) . . ? N1 Bi1 N6 125.61(9) . . ? N4 Bi1 N6 83.74(8) . . ? N2 Bi1 N6 84.52(8) . . ? N5 Bi1 C29 101.05(9) . . ? N3 Bi1 C29 28.21(9) . . ? N1 Bi1 C29 118.42(10) . . ? N4 Bi1 C29 27.05(9) . . ? N2 Bi1 C29 162.24(9) . . ? N6 Bi1 C29 110.20(9) . . ? N5 Bi1 C48 27.54(9) . . ? N3 Bi1 C48 120.14(9) . . ? N1 Bi1 C48 110.35(9) . . ? N4 Bi1 C48 87.29(9) . . ? N2 Bi1 C48 89.29(9) . . ? N6 Bi1 C48 26.64(9) . . ? C29 Bi1 C48 108.34(9) . . ? N5 Bi1 C10 98.83(10) . . ? N3 Bi1 C10 115.39(9) . . ? N1 Bi1 C10 27.85(9) . . ? N4 Bi1 C10 167.83(9) . . ? N2 Bi1 C10 26.95(9) . . ? N6 Bi1 C10 108.14(9) . . ? C29 Bi1 C10 141.55(10) . . ? C48 Bi1 C10 104.50(9) . . ? C10 N1 C1 115.7(3) . . ? C10 N1 Bi1 96.4(2) . . ? C1 N1 Bi1 135.7(2) . . ? C10 N2 C11 120.0(3) . . ? C10 N2 Bi1 86.6(2) . . ? C11 N2 Bi1 147.1(2) . . ? C29 N3 C20 118.1(3) . . ? C29 N3 Bi1 95.66(19) . . ? C20 N3 Bi1 131.3(2) . . ? C29 N4 C30 119.6(3) . . ? C29 N4 Bi1 87.47(19) . . ? C30 N4 Bi1 145.9(2) . . ? C48 N5 C39 117.8(3) . . ? C48 N5 Bi1 103.6(2) . . ? C39 N5 Bi1 137.5(2) . . ? C48 N6 C49 118.1(3) . . ? C48 N6 Bi1 81.56(19) . . ? C49 N6 Bi1 160.2(2) . . ? C2 C1 C6 120.2(3) . . ? C2 C1 N1 120.4(3) . . ? C6 C1 N1 119.4(3) . . ? C3 C2 C1 118.7(3) . . ? C3 C2 C7 119.0(3) . . ? C1 C2 C7 122.3(3) . . ? C4 C3 C2 122.3(3) . . ? C4 C3 H3 118.8 . . ? C2 C3 H3 118.8 . . ? C5 C4 C3 117.8(3) . . ? C5 C4 C8 121.8(3) . . ? C3 C4 C8 120.5(3) . . ? C4 C5 C6 122.2(3) . . ? C4 C5 H5 118.9 . . ? C6 C5 H5 118.9 . . ? C5 C6 C1 118.7(3) . . ? C5 C6 C9 120.4(3) . . ? C1 C6 C9 120.9(3) . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C4 C8 H8A 109.5 . . ? C4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N2 C10 N1 120.2(3) . . ? N2 C10 Bi1 66.46(18) . . ? N1 C10 Bi1 55.78(17) . . ? N2 C10 H10 119.9 . . ? N1 C10 H10 119.9 . . ? Bi1 C10 H10 164.8 . . ? C12 C11 C16 120.1(3) . . ? C12 C11 N2 123.1(3) . . ? C16 C11 N2 116.7(3) . . ? C13 C12 C11 117.7(3) . . ? C13 C12 C17 119.4(3) . . ? C11 C12 C17 122.9(3) . . ? C14 C13 C12 123.5(3) . . ? C14 C13 H13 118.2 . . ? C12 C13 H13 118.2 . . ? C13 C14 C15 117.8(3) . . ? C13 C14 C18 121.7(4) . . ? C15 C14 C18 120.5(4) . . ? C16 C15 C14 121.2(3) . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C15 C16 C11 119.7(3) . . ? C15 C16 C19 120.3(3) . . ? C11 C16 C19 120.0(3) . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C14 C18 H18A 109.5 . . ? C14 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C14 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C25 C20 C21 120.3(3) . . ? C25 C20 N3 121.7(3) . . ? C21 C20 N3 118.0(3) . . ? C22 C21 C20 118.6(3) . . ? C22 C21 C26 120.5(3) . . ? C20 C21 C26 120.8(3) . . ? C21 C22 C23 121.9(4) . . ? C21 C22 H22 119.1 . . ? C23 C22 H22 119.1 . . ? C24 C23 C22 118.1(3) . . ? C24 C23 C27 120.7(4) . . ? C22 C23 C27 121.2(4) . . ? C23 C24 C25 122.1(4) . . ? C23 C24 H24 119.0 . . ? C25 C24 H24 119.0 . . ? C20 C25 C24 119.1(4) . . ? C20 C25 C28 122.2(3) . . ? C24 C25 C28 118.8(3) . . ? C21 C26 H26A 109.5 . . ? C21 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C21 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C23 C27 H27A 109.5 . . ? C23 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C23 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? N4 C29 N3 118.8(3) . . ? N4 C29 Bi1 65.49(17) . . ? N3 C29 Bi1 56.13(16) . . ? N4 C29 H29 120.6 . . ? N3 C29 H29 120.6 . . ? Bi1 C29 H29 162.7 . . ? C31 C30 C35 119.8(3) . . ? C31 C30 N4 118.1(3) . . ? C35 C30 N4 121.8(3) . . ? C32 C31 C30 119.6(3) . . ? C32 C31 C36 119.8(3) . . ? C30 C31 C36 120.6(3) . . ? C31 C32 C33 121.8(4) . . ? C31 C32 H32 119.1 . . ? C33 C32 H32 119.1 . . ? C34 C33 C32 117.7(3) . . ? C34 C33 C37 120.7(4) . . ? C32 C33 C37 121.6(4) . . ? C33 C34 C35 122.9(3) . . ? C33 C34 H34 118.6 . . ? C35 C34 H34 118.6 . . ? C34 C35 C30 118.2(3) . . ? C34 C35 C38 119.7(3) . . ? C30 C35 C38 122.0(3) . . ? C31 C36 H36A 109.5 . . ? C31 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C31 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C33 C37 H37A 109.5 . . ? C33 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C33 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C35 C38 H38A 109.5 . . ? C35 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C35 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C40 C39 C44 121.2(3) . . ? C40 C39 N5 119.1(3) . . ? C44 C39 N5 119.6(3) . . ? C39 C40 C41 118.4(3) . . ? C39 C40 C45 120.7(3) . . ? C41 C40 C45 120.8(3) . . ? C42 C41 C40 122.0(3) . . ? C42 C41 H41 119.0 . . ? C40 C41 H41 119.0 . . ? C41 C42 C43 117.9(3) . . ? C41 C42 C46 121.3(4) . . ? C43 C42 C46 120.7(4) . . ? C44 C43 C42 122.2(3) . . ? C44 C43 H43 118.9 . . ? C42 C43 H43 118.9 . . ? C43 C44 C39 118.2(3) . . ? C43 C44 C47 121.3(3) . . ? C39 C44 C47 120.5(3) . . ? C40 C45 H45A 109.5 . . ? C40 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C40 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? C42 C46 H46A 109.5 . . ? C42 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C42 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? C44 C47 H47A 109.5 . . ? C44 C47 H47B 109.5 . . ? H47A C47 H47B 109.5 . . ? C44 C47 H47C 109.5 . . ? H47A C47 H47C 109.5 . . ? H47B C47 H47C 109.5 . . ? N6 C48 N5 120.6(3) . . ? N6 C48 Bi1 71.80(18) . . ? N5 C48 Bi1 48.84(15) . . ? N6 C48 H48 119.7 . . ? N5 C48 H48 119.7 . . ? Bi1 C48 H48 168.3 . . ? C50 C49 C54 120.0(3) . . ? C50 C49 N6 121.0(3) . . ? C54 C49 N6 119.0(3) . . ? C51 C50 C49 118.8(3) . . ? C51 C50 C55 119.6(3) . . ? C49 C50 C55 121.5(3) . . ? C50 C51 C52 122.7(3) . . ? C50 C51 H51 118.7 . . ? C52 C51 H51 118.7 . . ? C51 C52 C53 117.1(3) . . ? C51 C52 C56 121.7(3) . . ? C53 C52 C56 121.2(3) . . ? C54 C53 C52 122.6(3) . . ? C54 C53 H53 118.7 . . ? C52 C53 H53 118.7 . . ? C53 C54 C49 118.7(3) . . ? C53 C54 C57 120.4(3) . . ? C49 C54 C57 120.9(3) . . ? C50 C55 H55A 109.5 . . ? C50 C55 H55B 109.5 . . ? H55A C55 H55B 109.5 . . ? C50 C55 H55C 109.5 . . ? H55A C55 H55C 109.5 . . ? H55B C55 H55C 109.5 . . ? C52 C56 H56A 109.5 . . ? C52 C56 H56B 109.5 . . ? H56A C56 H56B 109.5 . . ? C52 C56 H56C 109.5 . . ? H56A C56 H56C 109.5 . . ? H56B C56 H56C 109.5 . . ? C54 C57 H57A 109.5 . . ? C54 C57 H57B 109.5 . . ? H57A C57 H57B 109.5 . . ? C54 C57 H57C 109.5 . . ? H57A C57 H57C 109.5 . . ? H57B C57 H57C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.834 _refine_diff_density_min -1.193 _refine_diff_density_rms 0.126 # Attachment '6a.CIF' data_6a _database_code_depnum_ccdc_archive 'CCDC 643181' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C54 H79 Bi N4' _chemical_formula_sum 'C54 H79 Bi N4' _chemical_formula_weight 993.19 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_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' _cell_length_a 10.6257(2) _cell_length_b 34.5254(9) _cell_length_c 14.7190(4) _cell_angle_alpha 90.00 _cell_angle_beta 109.626(1) _cell_angle_gamma 90.00 _cell_volume 5086.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.297 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2056 _exptl_absorpt_coefficient_mu 3.504 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5209 _exptl_absorpt_correction_T_max 0.7008 _exptl_absorpt_process_details SORTAV _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius KAPPA CCD' _diffrn_measurement_method '1.0 deg frames in phi and omega' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19826 _diffrn_reflns_av_R_equivalents 0.1273 _diffrn_reflns_av_sigmaI/netI 0.2734 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -44 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 27.50 _reflns_number_total 11152 _reflns_number_gt 5154 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed / POV-Ray' _computing_publication_material 'Microsoft Office 2000' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0158P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11152 _refine_ls_number_parameters 549 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1979 _refine_ls_R_factor_gt 0.0699 _refine_ls_wR_factor_ref 0.1180 _refine_ls_wR_factor_gt 0.0888 _refine_ls_goodness_of_fit_ref 0.937 _refine_ls_restrained_S_all 0.937 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 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 _atom_site_disorder_assembly _atom_site_disorder_group Bi1 Bi 0.89186(3) 0.104960(9) 0.17695(3) 0.01903(10) Uani 1 1 d . . . N1 N 0.8946(6) 0.17155(18) 0.1553(5) 0.0186(18) Uani 1 1 d . . . N2 N 0.8420(6) 0.14120(18) 0.0104(5) 0.0149(17) Uani 1 1 d . . . N3 N 1.0036(6) 0.1057(2) 0.3431(5) 0.0210(16) Uani 1 1 d . . . N4 N 0.9452(6) 0.04462(19) 0.2862(5) 0.0189(18) Uani 1 1 d . . . C1 C 1.0844(7) 0.0948(2) 0.1513(6) 0.023(2) Uani 1 1 d . . . H1A H 1.1212 0.1201 0.1409 0.028 Uiso 1 1 calc R . . H1B H 1.1488 0.0832 0.2100 0.028 Uiso 1 1 calc R . . C2 C 1.0735(8) 0.0686(2) 0.0654(6) 0.031(2) Uani 1 1 d . . . H2A H 1.0151 0.0810 0.0054 0.037 Uiso 1 1 calc R . . H2B H 1.0319 0.0437 0.0732 0.037 Uiso 1 1 calc R . . C3 C 1.2114(8) 0.0606(3) 0.0565(7) 0.044(3) Uani 1 1 d . . . H3A H 1.2700 0.0489 0.1174 0.053 Uiso 1 1 calc R . . H3B H 1.2518 0.0856 0.0478 0.053 Uiso 1 1 calc R . . C4 C 1.2064(9) 0.0335(2) -0.0280(7) 0.044(3) Uani 1 1 d . . . H4A H 1.1643 0.0089 -0.0210 0.066 Uiso 1 1 calc R . . H4B H 1.2975 0.0285 -0.0275 0.066 Uiso 1 1 calc R . . H4C H 1.1544 0.0458 -0.0891 0.066 Uiso 1 1 calc R . . C5 C 0.8475(7) 0.1726(2) 0.0590(7) 0.018(2) Uani 1 1 d . . . H5 H 0.8181 0.1964 0.0265 0.021 Uiso 1 1 calc R . . C6 C 0.8661(8) 0.2038(2) 0.2073(6) 0.021(2) Uani 1 1 d . . . C7 C 0.7319(8) 0.2121(2) 0.1980(6) 0.023(2) Uani 1 1 d . . . C8 C 0.7078(9) 0.2451(2) 0.2455(6) 0.024(2) Uani 1 1 d . . . H8 H 0.6192 0.2512 0.2420 0.029 Uiso 1 1 calc R . . C9 C 0.8123(10) 0.2687(3) 0.2972(7) 0.031(3) Uani 1 1 d . . . H9 H 0.7945 0.2911 0.3283 0.037 Uiso 1 1 calc R . . C10 C 0.9407(9) 0.2603(2) 0.3042(6) 0.027(2) Uani 1 1 d . . . H10 H 1.0104 0.2773 0.3393 0.032 Uiso 1 1 calc R . . C11 C 0.9725(8) 0.2274(2) 0.2614(6) 0.019(2) Uani 1 1 d . . . C12 C 0.6138(8) 0.1866(2) 0.1408(7) 0.026(2) Uani 1 1 d . . . H12 H 0.6499 0.1649 0.1119 0.031 Uiso 1 1 calc R . . C13 C 0.5421(9) 0.1688(2) 0.2053(7) 0.046(3) Uani 1 1 d . . . H13A H 0.5096 0.1895 0.2373 0.069 Uiso 1 1 calc R . . H13B H 0.6044 0.1522 0.2540 0.069 Uiso 1 1 calc R . . H13C H 0.4663 0.1532 0.1657 0.069 Uiso 1 1 calc R . . C14 C 0.5164(10) 0.2087(3) 0.0597(7) 0.053(3) Uani 1 1 d . . . H14A H 0.4775 0.2299 0.0860 0.080 Uiso 1 1 calc R . . H14B H 0.4451 0.1913 0.0220 0.080 Uiso 1 1 calc R . . H14C H 0.5627 0.2195 0.0180 0.080 Uiso 1 1 calc R . . C15 C 1.1139(8) 0.2182(3) 0.2679(7) 0.034(3) Uani 1 1 d . . . H15 H 1.1229 0.1894 0.2675 0.040 Uiso 1 1 calc R . . C16 C 1.2179(9) 0.2334(3) 0.3603(8) 0.049(3) Uani 1 1 d . . . H16A H 1.2244 0.2616 0.3564 0.073 Uiso 1 1 calc R . . H16B H 1.3049 0.2217 0.3679 0.073 Uiso 1 1 calc R . . H16C H 1.1911 0.2266 0.4158 0.073 Uiso 1 1 calc R . . C17 C 1.1432(9) 0.2343(3) 0.1793(7) 0.042(3) Uani 1 1 d . . . H17A H 1.0794 0.2233 0.1204 0.063 Uiso 1 1 calc R . . H17B H 1.2342 0.2272 0.1834 0.063 Uiso 1 1 calc R . . H17C H 1.1347 0.2626 0.1779 0.063 Uiso 1 1 calc R . . C18 C 0.7958(8) 0.1432(2) -0.0911(7) 0.020(2) Uani 1 1 d . . . C19 C 0.6664(8) 0.1297(2) -0.1438(7) 0.021(2) Uani 1 1 d . . . C20 C 0.6204(9) 0.1311(3) -0.2420(7) 0.032(3) Uani 1 1 d . . . H20 H 0.5337 0.1214 -0.2765 0.038 Uiso 1 1 calc R . . C21 C 0.6991(10) 0.1465(2) -0.2927(7) 0.037(3) Uani 1 1 d . . . H21 H 0.6649 0.1489 -0.3610 0.044 Uiso 1 1 calc R . . C22 C 0.8266(9) 0.1581(2) -0.2417(7) 0.032(3) Uani 1 1 d . . . H22 H 0.8818 0.1672 -0.2762 0.038 Uiso 1 1 calc R . . C23 C 0.8785(8) 0.1570(2) -0.1423(7) 0.020(2) Uani 1 1 d . . . C24 C 0.5811(8) 0.1111(2) -0.0877(6) 0.027(2) Uani 1 1 d . . . H24 H 0.6083 0.1230 -0.0220 0.033 Uiso 1 1 calc R . . C25 C 0.6090(9) 0.0684(2) -0.0758(7) 0.039(3) Uani 1 1 d . . . H25A H 0.5814 0.0560 -0.1393 0.058 Uiso 1 1 calc R . . H25B H 0.5590 0.0571 -0.0372 0.058 Uiso 1 1 calc R . . H25C H 0.7049 0.0642 -0.0431 0.058 Uiso 1 1 calc R . . C26 C 0.4316(8) 0.1182(2) -0.1371(8) 0.053(3) Uani 1 1 d . . . H26A H 0.4162 0.1457 -0.1535 0.080 Uiso 1 1 calc R . . H26B H 0.3835 0.1108 -0.0933 0.080 Uiso 1 1 calc R . . H26C H 0.3992 0.1026 -0.1960 0.080 Uiso 1 1 calc R . . C27 C 1.0216(8) 0.1694(2) -0.0878(7) 0.026(2) Uani 1 1 d . . . H27 H 1.0430 0.1616 -0.0189 0.031 Uiso 1 1 calc R . . C28 C 1.0374(8) 0.2128(2) -0.0902(7) 0.035(3) Uani 1 1 d . . . H28A H 1.1316 0.2197 -0.0588 0.052 Uiso 1 1 calc R . . H28B H 0.9834 0.2252 -0.0560 0.052 Uiso 1 1 calc R . . H28C H 1.0076 0.2217 -0.1573 0.052 Uiso 1 1 calc R . . C29 C 1.1200(9) 0.1483(2) -0.1273(8) 0.048(3) Uani 1 1 d . . . H29A H 1.1039 0.1204 -0.1283 0.072 Uiso 1 1 calc R . . H29B H 1.2118 0.1539 -0.0859 0.072 Uiso 1 1 calc R . . H29C H 1.1070 0.1574 -0.1930 0.072 Uiso 1 1 calc R . . C30 C 0.9970(7) 0.0675(2) 0.3587(6) 0.019(2) Uani 1 1 d . . . H30 H 1.0302 0.0574 0.4224 0.023 Uiso 1 1 calc R . . C31 C 1.0773(8) 0.1301(2) 0.4229(6) 0.019(2) Uani 1 1 d . . . C32 C 1.0066(9) 0.1534(2) 0.4655(7) 0.024(2) Uani 1 1 d . . . C33 C 1.0791(9) 0.1766(2) 0.5437(7) 0.027(2) Uani 1 1 d . . . H33 H 1.0324 0.1928 0.5736 0.032 Uiso 1 1 calc R . . C34 C 1.2174(9) 0.1762(2) 0.5784(6) 0.027(2) Uani 1 1 d . . . H34 H 1.2655 0.1920 0.6316 0.032 Uiso 1 1 calc R . . C35 C 1.2843(8) 0.1525(2) 0.5342(7) 0.029(2) Uani 1 1 d . . . H35 H 1.3792 0.1523 0.5574 0.034 Uiso 1 1 calc R . . C36 C 1.2167(8) 0.1289(2) 0.4573(6) 0.020(2) Uani 1 1 d . . . C37 C 0.8552(8) 0.1537(2) 0.4317(7) 0.023(2) Uani 1 1 d . . . H37 H 0.8226 0.1519 0.3598 0.028 Uiso 1 1 calc R . . C38 C 0.7939(8) 0.1902(2) 0.4587(6) 0.032(3) Uani 1 1 d . . . H38A H 0.8056 0.1896 0.5277 0.048 Uiso 1 1 calc R . . H38B H 0.6983 0.1913 0.4211 0.048 Uiso 1 1 calc R . . H38C H 0.8384 0.2132 0.4446 0.048 Uiso 1 1 calc R . . C39 C 0.8012(8) 0.1186(2) 0.4694(6) 0.033(3) Uani 1 1 d . . . H39A H 0.8455 0.0951 0.4579 0.050 Uiso 1 1 calc R . . H39B H 0.7047 0.1165 0.4357 0.050 Uiso 1 1 calc R . . H39C H 0.8185 0.1216 0.5387 0.050 Uiso 1 1 calc R . . C40 C 1.3005(7) 0.1038(2) 0.4150(6) 0.024(2) Uani 1 1 d . . . H40 H 1.2376 0.0867 0.3654 0.028 Uiso 1 1 calc R . . C41 C 1.3967(9) 0.0777(2) 0.4888(7) 0.041(3) Uani 1 1 d . . . H41A H 1.4645 0.0935 0.5358 0.061 Uiso 1 1 calc R . . H41B H 1.4403 0.0601 0.4563 0.061 Uiso 1 1 calc R . . H41C H 1.3476 0.0625 0.5222 0.061 Uiso 1 1 calc R . . C42 C 1.3769(9) 0.1287(2) 0.3628(7) 0.040(3) Uani 1 1 d . . . H42A H 1.4414 0.1454 0.4097 0.060 Uiso 1 1 calc R . . H42B H 1.3133 0.1448 0.3136 0.060 Uiso 1 1 calc R . . H42C H 1.4244 0.1116 0.3320 0.060 Uiso 1 1 calc R . . C43 C 0.9157(8) 0.0054(2) 0.3000(6) 0.024(2) Uani 1 1 d . . . C44 C 0.7882(8) -0.0044(2) 0.3004(6) 0.020(2) Uani 1 1 d . . . C45 C 0.7645(8) -0.0428(2) 0.3164(6) 0.026(2) Uani 1 1 d . . . H45 H 0.6796 -0.0497 0.3198 0.031 Uiso 1 1 calc R . . C46 C 0.8592(9) -0.0716(2) 0.3278(6) 0.028(2) Uani 1 1 d . . . H46 H 0.8405 -0.0976 0.3400 0.033 Uiso 1 1 calc R . . C47 C 0.9814(8) -0.0616(2) 0.3209(7) 0.031(3) Uani 1 1 d . . . H47 H 1.0454 -0.0813 0.3250 0.037 Uiso 1 1 calc R . . C48 C 1.0136(8) -0.0231(2) 0.3082(6) 0.015(2) Uani 1 1 d . . . C49 C 0.6791(8) 0.0262(2) 0.2782(6) 0.022(2) Uani 1 1 d . . . H49 H 0.7217 0.0513 0.3061 0.026 Uiso 1 1 calc R . . C50 C 0.6173(8) 0.0313(2) 0.1700(6) 0.028(2) Uani 1 1 d . . . H50A H 0.6882 0.0335 0.1416 0.042 Uiso 1 1 calc R . . H50B H 0.5627 0.0549 0.1561 0.042 Uiso 1 1 calc R . . H50C H 0.5610 0.0089 0.1423 0.042 Uiso 1 1 calc R . . C51 C 0.5686(8) 0.0173(3) 0.3214(7) 0.045(3) Uani 1 1 d . . . H51A H 0.5180 -0.0055 0.2894 0.067 Uiso 1 1 calc R . . H51B H 0.5083 0.0396 0.3117 0.067 Uiso 1 1 calc R . . H51C H 0.6093 0.0121 0.3906 0.067 Uiso 1 1 calc R . . C52 C 1.1504(8) -0.0134(3) 0.3040(7) 0.029(3) Uani 1 1 d . . . H52 H 1.1532 0.0153 0.2946 0.035 Uiso 1 1 calc R . . C53 C 1.2604(9) -0.0232(3) 0.3970(8) 0.067(4) Uani 1 1 d . . . H53A H 1.2402 -0.0116 0.4514 0.100 Uiso 1 1 calc R . . H53B H 1.3455 -0.0130 0.3951 0.100 Uiso 1 1 calc R . . H53C H 1.2668 -0.0514 0.4050 0.100 Uiso 1 1 calc R . . C54 C 1.1764(10) -0.0327(3) 0.2190(8) 0.056(3) Uani 1 1 d . . . H54A H 1.1708 -0.0609 0.2246 0.085 Uiso 1 1 calc R . . H54B H 1.2658 -0.0257 0.2190 0.085 Uiso 1 1 calc R . . H54C H 1.1094 -0.0241 0.1586 0.085 Uiso 1 1 calc R . . 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 0.01672(16) 0.01759(17) 0.02150(19) -0.0004(2) 0.00474(13) -0.0013(2) N1 0.011(4) 0.019(4) 0.024(5) 0.004(4) 0.004(4) -0.006(3) N2 0.015(4) 0.006(4) 0.020(5) -0.005(4) 0.002(4) -0.003(3) N3 0.021(4) 0.018(4) 0.025(4) 0.001(5) 0.010(3) 0.000(4) N4 0.011(4) 0.022(4) 0.023(5) -0.008(4) 0.004(4) -0.004(3) C1 0.019(5) 0.028(6) 0.026(6) 0.002(5) 0.011(4) 0.005(4) C2 0.029(6) 0.026(6) 0.029(6) 0.000(5) -0.001(5) 0.007(4) C3 0.025(6) 0.062(8) 0.046(8) 0.011(6) 0.013(6) 0.006(5) C4 0.049(7) 0.035(7) 0.056(8) -0.016(6) 0.028(7) 0.009(5) C5 0.012(5) 0.020(5) 0.023(6) 0.011(5) 0.008(4) 0.001(4) C6 0.022(5) 0.014(5) 0.025(6) 0.001(5) 0.005(5) 0.001(4) C7 0.032(6) 0.016(5) 0.024(6) 0.002(5) 0.012(5) 0.001(4) C8 0.027(6) 0.024(5) 0.026(6) 0.009(5) 0.017(5) 0.004(4) C9 0.046(7) 0.034(6) 0.019(6) 0.002(5) 0.019(6) 0.011(5) C10 0.035(6) 0.022(6) 0.024(6) -0.012(5) 0.009(5) -0.011(5) C11 0.030(6) 0.006(5) 0.018(6) -0.001(4) 0.002(5) -0.007(4) C12 0.024(6) 0.025(5) 0.032(7) -0.006(5) 0.013(5) 0.002(4) C13 0.036(7) 0.052(7) 0.045(8) -0.004(6) 0.006(6) -0.017(5) C14 0.049(7) 0.066(8) 0.034(7) 0.009(6) 0.001(6) -0.020(6) C15 0.021(6) 0.028(6) 0.044(7) 0.003(5) 0.002(5) -0.005(4) C16 0.032(7) 0.039(7) 0.067(9) -0.005(6) 0.005(7) -0.006(5) C17 0.027(6) 0.068(8) 0.030(7) -0.007(6) 0.009(5) -0.012(5) C18 0.019(5) 0.012(5) 0.025(6) 0.002(5) 0.004(5) 0.006(4) C19 0.025(5) 0.017(5) 0.029(6) -0.001(5) 0.020(5) 0.005(4) C20 0.025(6) 0.041(7) 0.024(7) -0.004(6) 0.000(5) 0.001(5) C21 0.050(7) 0.042(7) 0.018(6) 0.006(5) 0.011(6) 0.013(6) C22 0.029(6) 0.043(7) 0.029(7) -0.002(6) 0.019(6) -0.002(5) C23 0.021(5) 0.017(5) 0.023(6) 0.004(5) 0.008(5) 0.008(4) C24 0.021(5) 0.042(7) 0.018(5) -0.009(5) 0.005(4) 0.004(5) C25 0.048(7) 0.034(6) 0.038(7) 0.010(6) 0.020(6) -0.001(5) C26 0.025(6) 0.042(7) 0.094(10) 0.004(6) 0.022(7) 0.012(5) C27 0.025(5) 0.022(5) 0.042(7) 0.001(5) 0.025(5) -0.006(4) C28 0.029(6) 0.041(6) 0.041(7) 0.007(6) 0.020(5) -0.002(5) C29 0.034(6) 0.040(7) 0.079(9) -0.002(6) 0.032(7) -0.002(5) C30 0.009(5) 0.026(6) 0.019(6) 0.009(5) 0.002(4) 0.002(4) C31 0.020(5) 0.015(5) 0.023(6) 0.000(4) 0.008(5) -0.006(4) C32 0.029(6) 0.027(6) 0.017(6) -0.005(5) 0.009(5) -0.008(5) C33 0.033(6) 0.020(5) 0.028(6) 0.006(5) 0.010(5) 0.010(4) C34 0.035(6) 0.022(5) 0.020(6) -0.007(5) 0.006(5) -0.007(4) C35 0.014(5) 0.026(6) 0.045(7) -0.003(5) 0.009(5) -0.002(4) C36 0.016(5) 0.017(5) 0.018(6) 0.003(4) -0.005(4) 0.001(4) C37 0.032(6) 0.022(5) 0.019(6) 0.003(5) 0.012(5) 0.002(4) C38 0.036(6) 0.028(6) 0.036(7) 0.001(5) 0.016(5) 0.015(5) C39 0.015(5) 0.052(7) 0.028(6) 0.001(5) 0.002(5) 0.010(4) C40 0.016(4) 0.009(4) 0.049(6) 0.003(6) 0.015(5) -0.001(4) C41 0.052(7) 0.030(6) 0.050(8) 0.009(6) 0.030(6) 0.027(5) C42 0.041(7) 0.031(6) 0.054(8) 0.004(6) 0.023(6) 0.000(5) C43 0.019(5) 0.024(6) 0.026(6) 0.000(5) 0.004(5) -0.003(4) C44 0.026(5) 0.020(5) 0.015(6) -0.007(5) 0.006(5) -0.006(4) C45 0.017(5) 0.032(6) 0.027(6) -0.002(5) 0.006(5) -0.018(4) C46 0.044(6) 0.010(5) 0.027(6) 0.003(5) 0.009(5) -0.003(5) C47 0.018(5) 0.022(6) 0.050(8) 0.003(5) 0.008(5) 0.000(4) C48 0.012(5) 0.016(5) 0.018(6) 0.005(4) 0.006(4) -0.006(4) C49 0.026(5) 0.014(5) 0.029(6) 0.002(5) 0.013(5) 0.000(4) C50 0.025(6) 0.017(5) 0.038(7) 0.007(5) 0.005(5) 0.001(4) C51 0.033(7) 0.055(7) 0.050(8) -0.009(6) 0.018(6) 0.009(5) C52 0.019(6) 0.030(6) 0.040(7) -0.008(6) 0.013(5) 0.003(4) C53 0.021(6) 0.106(10) 0.065(10) 0.014(8) 0.003(6) -0.008(6) C54 0.040(7) 0.066(8) 0.065(10) 0.003(7) 0.020(7) -0.005(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Bi1 C1 2.230(7) . ? Bi1 N1 2.323(6) . ? Bi1 N3 2.333(7) . ? Bi1 N4 2.576(7) . ? Bi1 N2 2.643(7) . ? Bi1 C30 2.842(9) . ? Bi1 C5 2.853(8) . ? N1 C5 1.335(10) . ? N1 C6 1.441(9) . ? N2 C5 1.290(9) . ? N2 C18 1.409(10) . ? N3 C30 1.344(9) . ? N3 C31 1.445(10) . ? N4 C30 1.292(9) . ? N4 C43 1.419(9) . ? C1 C2 1.528(10) . ? C2 C3 1.539(10) . ? C3 C4 1.544(11) . ? C6 C11 1.404(10) . ? C6 C7 1.415(10) . ? C7 C8 1.405(10) . ? C7 C12 1.531(11) . ? C8 C9 1.382(11) . ? C9 C10 1.365(11) . ? C10 C11 1.393(10) . ? C11 C15 1.507(11) . ? C12 C14 1.500(11) . ? C12 C13 1.531(11) . ? C15 C16 1.528(12) . ? C15 C17 1.543(11) . ? C18 C19 1.411(11) . ? C18 C23 1.418(11) . ? C19 C20 1.362(12) . ? C19 C24 1.557(10) . ? C20 C21 1.401(11) . ? C21 C22 1.369(11) . ? C22 C23 1.380(12) . ? C23 C27 1.524(11) . ? C24 C25 1.503(10) . ? C24 C26 1.528(11) . ? C27 C28 1.510(9) . ? C27 C29 1.539(10) . ? C31 C32 1.386(10) . ? C31 C36 1.395(10) . ? C32 C33 1.401(11) . ? C32 C37 1.516(11) . ? C33 C34 1.385(10) . ? C34 C35 1.382(10) . ? C35 C36 1.382(11) . ? C36 C40 1.519(10) . ? C37 C39 1.523(10) . ? C37 C38 1.533(9) . ? C40 C41 1.514(10) . ? C40 C42 1.553(10) . ? C43 C44 1.398(10) . ? C43 C48 1.409(10) . ? C44 C45 1.384(10) . ? C44 C49 1.522(10) . ? C45 C46 1.384(10) . ? C46 C47 1.380(10) . ? C47 C48 1.400(10) . ? C48 C52 1.514(10) . ? C49 C50 1.516(11) . ? C49 C51 1.542(10) . ? C52 C53 1.510(12) . ? C52 C54 1.524(11) . ? 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 C1 Bi1 N1 94.5(2) . . ? C1 Bi1 N3 90.4(3) . . ? N1 Bi1 N3 96.2(2) . . ? C1 Bi1 N4 87.5(2) . . ? N1 Bi1 N4 151.1(2) . . ? N3 Bi1 N4 55.0(2) . . ? C1 Bi1 N2 80.0(2) . . ? N1 Bi1 N2 54.0(2) . . ? N3 Bi1 N2 147.2(2) . . ? N4 Bi1 N2 153.6(2) . . ? C1 Bi1 C30 89.7(3) . . ? N1 Bi1 C30 124.1(2) . . ? N3 Bi1 C30 28.0(2) . . ? N4 Bi1 C30 27.03(19) . . ? N2 Bi1 C30 169.13(19) . . ? C1 Bi1 C5 89.9(2) . . ? N1 Bi1 C5 27.5(2) . . ? N3 Bi1 C5 123.4(3) . . ? N4 Bi1 C5 177.0(2) . . ? N2 Bi1 C5 26.80(19) . . ? C30 Bi1 C5 151.4(3) . . ? C5 N1 C6 118.1(7) . . ? C5 N1 Bi1 98.9(5) . . ? C6 N1 Bi1 132.7(5) . . ? C5 N2 C18 118.8(7) . . ? C5 N2 Bi1 85.7(5) . . ? C18 N2 Bi1 153.7(5) . . ? C30 N3 C31 118.7(7) . . ? C30 N3 Bi1 97.6(5) . . ? C31 N3 Bi1 143.5(5) . . ? C30 N4 C43 121.2(8) . . ? C30 N4 Bi1 88.0(5) . . ? C43 N4 Bi1 148.0(6) . . ? C2 C1 Bi1 114.5(5) . . ? C1 C2 C3 111.5(7) . . ? C2 C3 C4 113.6(8) . . ? N2 C5 N1 119.8(8) . . ? N2 C5 Bi1 67.5(5) . . ? N1 C5 Bi1 53.5(4) . . ? C11 C6 C7 122.2(8) . . ? C11 C6 N1 118.5(7) . . ? C7 C6 N1 119.2(7) . . ? C8 C7 C6 117.4(8) . . ? C8 C7 C12 119.1(8) . . ? C6 C7 C12 123.5(8) . . ? C9 C8 C7 120.4(8) . . ? C10 C9 C8 120.8(9) . . ? C9 C10 C11 121.9(8) . . ? C10 C11 C6 117.2(8) . . ? C10 C11 C15 122.1(8) . . ? C6 C11 C15 120.6(8) . . ? C14 C12 C7 111.4(7) . . ? C14 C12 C13 110.1(7) . . ? C7 C12 C13 112.1(8) . . ? C11 C15 C16 113.1(8) . . ? C11 C15 C17 110.5(8) . . ? C16 C15 C17 109.7(7) . . ? N2 C18 C19 119.7(8) . . ? N2 C18 C23 121.5(8) . . ? C19 C18 C23 118.8(8) . . ? C20 C19 C18 120.5(8) . . ? C20 C19 C24 120.8(8) . . ? C18 C19 C24 118.6(8) . . ? C19 C20 C21 120.9(9) . . ? C22 C21 C20 118.4(10) . . ? C21 C22 C23 122.9(9) . . ? C22 C23 C18 118.3(8) . . ? C22 C23 C27 121.5(8) . . ? C18 C23 C27 120.2(8) . . ? C25 C24 C26 110.2(7) . . ? C25 C24 C19 109.9(6) . . ? C26 C24 C19 112.3(7) . . ? C28 C27 C23 111.5(7) . . ? C28 C27 C29 111.4(7) . . ? C23 C27 C29 110.7(7) . . ? N4 C30 N3 119.3(8) . . ? N4 C30 Bi1 65.0(5) . . ? N3 C30 Bi1 54.5(4) . . ? C32 C31 C36 121.6(8) . . ? C32 C31 N3 118.5(7) . . ? C36 C31 N3 119.9(7) . . ? C31 C32 C33 118.1(8) . . ? C31 C32 C37 122.2(8) . . ? C33 C32 C37 119.7(8) . . ? C34 C33 C32 121.4(8) . . ? C35 C34 C33 118.7(8) . . ? C36 C35 C34 121.8(8) . . ? C35 C36 C31 118.5(8) . . ? C35 C36 C40 117.2(7) . . ? C31 C36 C40 124.4(8) . . ? C32 C37 C39 111.3(7) . . ? C32 C37 C38 114.7(7) . . ? C39 C37 C38 108.4(7) . . ? C41 C40 C36 113.2(7) . . ? C41 C40 C42 110.2(6) . . ? C36 C40 C42 111.3(7) . . ? C44 C43 C48 121.2(8) . . ? C44 C43 N4 119.6(7) . . ? C48 C43 N4 119.1(7) . . ? C45 C44 C43 117.7(8) . . ? C45 C44 C49 122.2(7) . . ? C43 C44 C49 120.0(7) . . ? C46 C45 C44 122.8(8) . . ? C47 C46 C45 118.4(8) . . ? C46 C47 C48 121.7(8) . . ? C47 C48 C43 117.9(7) . . ? C47 C48 C52 119.8(7) . . ? C43 C48 C52 122.2(7) . . ? C50 C49 C44 109.6(7) . . ? C50 C49 C51 109.6(7) . . ? C44 C49 C51 113.8(7) . . ? C53 C52 C48 112.0(8) . . ? C53 C52 C54 110.3(8) . . ? C48 C52 C54 112.2(8) . . ? _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 1.691 _refine_diff_density_min -1.438 _refine_diff_density_rms 0.210 data_bilcl2ab _database_code_depnum_ccdc_archive 'CCDC 645997' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C83 H121 Bi3 Cl6 N6 O2, 2(C7 H8)' _chemical_formula_sum 'C97 H137 Bi3 Cl6 N6 O2' _chemical_formula_weight 2258.77 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_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' _cell_length_a 46.047(9) _cell_length_b 16.728(3) _cell_length_c 28.311(6) _cell_angle_alpha 90.00 _cell_angle_beta 112.74(3) _cell_angle_gamma 90.00 _cell_volume 20112(8) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.492 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 9024 _exptl_absorpt_coefficient_mu 5.443 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.3990 _exptl_absorpt_correction_T_max 0.7625 _exptl_absorpt_process_details SORTAV _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius KAPPA CCD' _diffrn_measurement_method '1 deg frames in phi and omega' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 95936 _diffrn_reflns_av_R_equivalents 0.0853 _diffrn_reflns_av_sigmaI/netI 0.0755 _diffrn_reflns_limit_h_min -59 _diffrn_reflns_limit_h_max 59 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 27.49 _reflns_number_total 22992 _reflns_number_gt 15964 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Burker AXS, 2004)' _computing_cell_refinement 'DNZO-SMN (Otwinoski and Minor 1997)' _computing_data_reduction 'DNZO-SMN (Otwinoski and Minor 1997)' _computing_structure_solution 'sir92 (?)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0519P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 22992 _refine_ls_number_parameters 1018 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.0805 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1047 _refine_ls_wR_factor_gt 0.0923 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 _atom_site_disorder_assembly _atom_site_disorder_group Bi1 Bi 0.088898(5) -0.133121(12) 0.066755(8) 0.02649(6) Uani 1 1 d . . . Cl1 Cl 0.12250(4) -0.13886(8) 0.00305(6) 0.0371(4) Uani 1 1 d . . . O1 O 0.04430(9) -0.0612(2) 0.08680(16) 0.0392(10) Uani 1 1 d . . . N1 N 0.08289(11) -0.2226(2) 0.12675(17) 0.0274(10) Uani 1 1 d . . . C1 C 0.10491(13) -0.2706(3) 0.1246(2) 0.0309(13) Uani 1 1 d . . . H1 H 0.1108 -0.3177 0.1448 0.037 Uiso 1 1 calc R . . Bi2 Bi 0.139343(5) 0.019532(12) 0.016768(7) 0.02549(6) Uani 1 1 d . . . Cl2 Cl 0.04427(4) -0.19906(9) -0.00291(6) 0.0432(4) Uani 1 1 d . . . O2 O 0.08925(11) 0.2358(3) 0.10456(18) 0.0571(13) Uani 1 1 d . . . N2 N 0.11837(11) -0.2500(3) 0.09308(17) 0.0314(11) Uani 1 1 d . . . C2 C 0.06259(14) -0.2426(3) 0.1519(2) 0.0335(14) Uani 1 1 d . . . Bi3 Bi 0.136684(5) 0.140198(12) 0.138287(7) 0.02311(6) Uani 1 1 d . . . Cl3 Cl 0.15565(4) 0.16956(8) 0.03798(5) 0.0353(3) Uani 1 1 d . . . N3 N 0.16988(10) 0.0130(2) -0.03706(16) 0.0250(10) Uani 1 1 d . . . C3 C 0.06397(15) -0.1952(3) 0.1940(2) 0.0378(15) Uani 1 1 d . . . Cl4 Cl 0.08404(3) 0.05315(9) 0.01482(5) 0.0350(3) Uani 1 1 d . . . N4 N 0.11829(10) 0.0394(3) -0.06868(15) 0.0265(10) Uani 1 1 d . . . C4 C 0.04330(17) -0.2141(4) 0.2182(3) 0.0511(18) Uani 1 1 d . . . H4 H 0.0438 -0.1837 0.2468 0.061 Uiso 1 1 calc R . . Cl5 Cl 0.11651(4) 0.12418(9) 0.20705(5) 0.0387(4) Uani 1 1 d . . . N5 N 0.18815(10) 0.1439(2) 0.19478(15) 0.0230(10) Uani 1 1 d . . . C5 C 0.02209(17) -0.2770(5) 0.2003(3) 0.058(2) Uani 1 1 d . . . H5 H 0.0082 -0.2891 0.2169 0.069 Uiso 1 1 calc R . . Cl6 Cl 0.14545(4) -0.02227(8) 0.13680(5) 0.0366(3) Uani 1 1 d . . . N6 N 0.16273(10) 0.2611(3) 0.17729(17) 0.0279(11) Uani 1 1 d . . . C6 C 0.02088(16) -0.3219(4) 0.1591(3) 0.0542(19) Uani 1 1 d . . . H6 H 0.0064 -0.3650 0.1478 0.065 Uiso 1 1 calc R . . C7 C 0.04076(14) -0.3050(4) 0.1335(3) 0.0423(16) Uani 1 1 d . . . C8 C 0.08844(17) -0.1301(4) 0.2137(2) 0.0478(18) Uani 1 1 d . . . H8 H 0.0909 -0.1053 0.1834 0.057 Uiso 1 1 calc R . . C9 C 0.0794(2) -0.0634(4) 0.2426(3) 0.068(2) Uani 1 1 d . . . H9A H 0.0583 -0.0436 0.2216 0.102 Uiso 1 1 calc R . . H9B H 0.0946 -0.0196 0.2496 0.102 Uiso 1 1 calc R . . H9C H 0.0795 -0.0844 0.2750 0.102 Uiso 1 1 calc R . . C10 C 0.12028(17) -0.1672(5) 0.2473(3) 0.064(2) Uani 1 1 d . . . H10A H 0.1186 -0.1927 0.2773 0.096 Uiso 1 1 calc R . . H10B H 0.1364 -0.1253 0.2585 0.096 Uiso 1 1 calc R . . H10C H 0.1262 -0.2073 0.2274 0.096 Uiso 1 1 calc R . . C11 C 0.03811(16) -0.3558(4) 0.0879(3) 0.0492(18) Uani 1 1 d . . . H11 H 0.0521 -0.3315 0.0722 0.059 Uiso 1 1 calc R . . C12 C 0.00477(17) -0.3573(5) 0.0467(3) 0.076(3) Uani 1 1 d . . . H12A H -0.0097 -0.3795 0.0611 0.114 Uiso 1 1 calc R . . H12B H 0.0044 -0.3907 0.0180 0.114 Uiso 1 1 calc R . . H12C H -0.0017 -0.3028 0.0345 0.114 Uiso 1 1 calc R . . C13 C 0.05001(19) -0.4414(4) 0.1045(4) 0.072(2) Uani 1 1 d . . . H13A H 0.0711 -0.4393 0.1317 0.108 Uiso 1 1 calc R . . H13B H 0.0508 -0.4708 0.0751 0.108 Uiso 1 1 calc R . . H13C H 0.0356 -0.4686 0.1173 0.108 Uiso 1 1 calc R . . C14 C 0.14553(13) -0.2896(3) 0.0912(2) 0.0299(13) Uani 1 1 d . . . C15 C 0.17490(14) -0.2805(3) 0.1318(2) 0.0320(13) Uani 1 1 d . . . C16 C 0.20048(14) -0.3227(3) 0.1294(2) 0.0387(15) Uani 1 1 d . . . H16 H 0.2204 -0.3191 0.1570 0.046 Uiso 1 1 calc R . . C17 C 0.19721(15) -0.3700(4) 0.0872(3) 0.0431(16) Uani 1 1 d . . . H17 H 0.2147 -0.3988 0.0862 0.052 Uiso 1 1 calc R . . C18 C 0.16840(15) -0.3749(3) 0.0469(2) 0.0401(15) Uani 1 1 d . . . H18 H 0.1666 -0.4056 0.0177 0.048 Uiso 1 1 calc R . . C19 C 0.14180(14) -0.3360(3) 0.0479(2) 0.0340(14) Uani 1 1 d . . . C20 C 0.10982(15) -0.3460(4) 0.0042(2) 0.0390(15) Uani 1 1 d . . . H20 H 0.0971 -0.2972 0.0035 0.047 Uiso 1 1 calc R . . C21 C 0.1115(2) -0.3542(5) -0.0485(3) 0.071(2) Uani 1 1 d . . . H21A H 0.1238 -0.3100 -0.0539 0.107 Uiso 1 1 calc R . . H21B H 0.0901 -0.3529 -0.0751 0.107 Uiso 1 1 calc R . . H21C H 0.1215 -0.4051 -0.0504 0.107 Uiso 1 1 calc R . . C22 C 0.09281(17) -0.4176(4) 0.0156(3) 0.066(2) Uani 1 1 d . . . H22A H 0.1035 -0.4671 0.0132 0.099 Uiso 1 1 calc R . . H22B H 0.0710 -0.4191 -0.0093 0.099 Uiso 1 1 calc R . . H22C H 0.0930 -0.4125 0.0502 0.099 Uiso 1 1 calc R . . C23 C 0.18026(14) -0.2259(3) 0.1774(2) 0.0370(15) Uani 1 1 d . . . H23 H 0.1605 -0.1949 0.1704 0.044 Uiso 1 1 calc R . . C24 C 0.20712(16) -0.1656(4) 0.1847(3) 0.061(2) Uani 1 1 d . . . H24A H 0.2273 -0.1939 0.1967 0.092 Uiso 1 1 calc R . . H24B H 0.2075 -0.1253 0.2101 0.092 Uiso 1 1 calc R . . H24C H 0.2036 -0.1393 0.1520 0.092 Uiso 1 1 calc R . . C25 C 0.18710(18) -0.2750(4) 0.2264(2) 0.056(2) Uani 1 1 d . . . H25A H 0.1684 -0.3060 0.2232 0.084 Uiso 1 1 calc R . . H25B H 0.1926 -0.2388 0.2558 0.084 Uiso 1 1 calc R . . H25C H 0.2047 -0.3115 0.2315 0.084 Uiso 1 1 calc R . . C26 C 0.14447(13) 0.0293(3) -0.0772(2) 0.0282(13) Uani 1 1 d . . . H26 H 0.1447 0.0337 -0.1105 0.034 Uiso 1 1 calc R . . C27 C 0.08731(13) 0.0433(4) -0.1080(2) 0.0353(15) Uani 1 1 d . . . C28 C 0.07082(14) 0.1169(4) -0.1155(2) 0.0418(16) Uani 1 1 d . . . C29 C 0.04037(16) 0.1194(5) -0.1521(2) 0.057(2) Uani 1 1 d . . . H29 H 0.0287 0.1678 -0.1576 0.068 Uiso 1 1 calc R . . C30 C 0.02668(17) 0.0528(7) -0.1806(3) 0.073(3) Uani 1 1 d . . . H30 H 0.0056 0.0556 -0.2051 0.088 Uiso 1 1 calc R . . C31 C 0.04297(18) -0.0172(5) -0.1741(2) 0.059(2) Uani 1 1 d . . . H31 H 0.0334 -0.0618 -0.1951 0.071 Uiso 1 1 calc R . . C32 C 0.07389(15) -0.0245(4) -0.1367(2) 0.0414(16) Uani 1 1 d . . . C33 C 0.09129(18) -0.1023(4) -0.1311(2) 0.053(2) Uani 1 1 d . . . H33 H 0.1103 -0.0996 -0.0984 0.063 Uiso 1 1 calc R . . C34 C 0.10259(19) -0.1161(4) -0.1735(3) 0.057(2) Uani 1 1 d . . . H34A H 0.0846 -0.1151 -0.2065 0.086 Uiso 1 1 calc R . . H34B H 0.1130 -0.1683 -0.1688 0.086 Uiso 1 1 calc R . . H34C H 0.1175 -0.0740 -0.1729 0.086 Uiso 1 1 calc R . . C35 C 0.0713(2) -0.1752(5) -0.1272(3) 0.088(3) Uani 1 1 d . . . H35A H 0.0529 -0.1809 -0.1594 0.132 Uiso 1 1 calc R . . H35B H 0.0644 -0.1668 -0.0989 0.132 Uiso 1 1 calc R . . H35C H 0.0841 -0.2239 -0.1209 0.132 Uiso 1 1 calc R . . C36 C 0.08665(15) 0.1909(4) -0.0873(2) 0.0445(16) Uani 1 1 d . . . H36 H 0.1023 0.1742 -0.0530 0.053 Uiso 1 1 calc R . . C37 C 0.10477(18) 0.2313(4) -0.1163(3) 0.060(2) Uani 1 1 d . . . H37A H 0.1207 0.1944 -0.1185 0.090 Uiso 1 1 calc R . . H37B H 0.1150 0.2798 -0.0980 0.090 Uiso 1 1 calc R . . H37C H 0.0901 0.2455 -0.1509 0.090 Uiso 1 1 calc R . . C38 C 0.06411(19) 0.2517(5) -0.0783(3) 0.070(2) Uani 1 1 d . . . H38A H 0.0509 0.2763 -0.1109 0.106 Uiso 1 1 calc R . . H38B H 0.0764 0.2931 -0.0545 0.106 Uiso 1 1 calc R . . H38C H 0.0507 0.2241 -0.0637 0.106 Uiso 1 1 calc R . . C39 C 0.20078(13) 0.0182(3) -0.03547(19) 0.0277(12) Uani 1 1 d . . . C40 C 0.22088(13) -0.0473(3) -0.0150(2) 0.0313(13) Uani 1 1 d . . . C41 C 0.25180(14) -0.0427(4) -0.0118(2) 0.0396(15) Uani 1 1 d . . . H41 H 0.2657 -0.0866 0.0014 0.048 Uiso 1 1 calc R . . C42 C 0.26245(16) 0.0252(4) -0.0277(3) 0.0498(18) Uani 1 1 d . . . H42 H 0.2834 0.0271 -0.0264 0.060 Uiso 1 1 calc R . . C43 C 0.24279(14) 0.0905(4) -0.0455(2) 0.0398(15) Uani 1 1 d . . . H43 H 0.2507 0.1375 -0.0552 0.048 Uiso 1 1 calc R . . C44 C 0.21202(13) 0.0889(3) -0.0495(2) 0.0319(13) Uani 1 1 d . . . C45 C 0.20827(15) -0.1212(4) 0.0027(2) 0.0394(15) Uani 1 1 d . . . H45 H 0.1930 -0.1019 0.0174 0.047 Uiso 1 1 calc R . . C46 C 0.19020(16) -0.1768(4) -0.0420(2) 0.0488(17) Uani 1 1 d . . . H46A H 0.1733 -0.1468 -0.0682 0.073 Uiso 1 1 calc R . . H46B H 0.1811 -0.2210 -0.0295 0.073 Uiso 1 1 calc R . . H46C H 0.2046 -0.1982 -0.0568 0.073 Uiso 1 1 calc R . . C47 C 0.23392(17) -0.1689(4) 0.0450(3) 0.0543(19) Uani 1 1 d . . . H47A H 0.2243 -0.2151 0.0547 0.081 Uiso 1 1 calc R . . H47B H 0.2439 -0.1345 0.0750 0.081 Uiso 1 1 calc R . . H47C H 0.2498 -0.1873 0.0323 0.081 Uiso 1 1 calc R . . C48 C 0.19194(14) 0.1643(3) -0.0664(2) 0.0318(13) Uani 1 1 d . . . H48 H 0.1714 0.1534 -0.0634 0.038 Uiso 1 1 calc R . . C49 C 0.20651(16) 0.2369(4) -0.0334(2) 0.0463(17) Uani 1 1 d . . . H49A H 0.2126 0.2231 0.0028 0.069 Uiso 1 1 calc R . . H49B H 0.1912 0.2807 -0.0425 0.069 Uiso 1 1 calc R . . H49C H 0.2252 0.2538 -0.0393 0.069 Uiso 1 1 calc R . . C50 C 0.18488(15) 0.1833(4) -0.1227(2) 0.0444(16) Uani 1 1 d . . . H50A H 0.1714 0.2308 -0.1330 0.067 Uiso 1 1 calc R . . H50B H 0.1740 0.1378 -0.1440 0.067 Uiso 1 1 calc R . . H50C H 0.2047 0.1934 -0.1270 0.067 Uiso 1 1 calc R . . C51 C 0.18896(13) 0.2222(3) 0.2017(2) 0.0281(13) Uani 1 1 d . . . H51 H 0.2076 0.2488 0.2233 0.034 Uiso 1 1 calc R . . C52 C 0.21481(12) 0.0928(3) 0.21976(19) 0.0250(12) Uani 1 1 d . . . C53 C 0.23464(13) 0.0742(3) 0.1943(2) 0.0304(13) Uani 1 1 d . . . C54 C 0.26082(14) 0.0248(3) 0.2204(2) 0.0359(14) Uani 1 1 d . . . H54 H 0.2751 0.0120 0.2048 0.043 Uiso 1 1 calc R . . C55 C 0.26589(15) -0.0047(4) 0.2678(2) 0.0419(16) Uani 1 1 d . . . H55 H 0.2834 -0.0385 0.2846 0.050 Uiso 1 1 calc R . . C56 C 0.24581(14) 0.0141(4) 0.2916(2) 0.0384(15) Uani 1 1 d . . . H56 H 0.2499 -0.0069 0.3247 0.046 Uiso 1 1 calc R . . C57 C 0.21979(13) 0.0627(3) 0.2687(2) 0.0317(13) Uani 1 1 d . . . C58 C 0.19703(14) 0.0797(4) 0.2941(2) 0.0407(16) Uani 1 1 d . . . H58 H 0.1799 0.1147 0.2707 0.049 Uiso 1 1 calc R . . C59 C 0.2124(2) 0.1222(8) 0.3445(4) 0.144(6) Uani 1 1 d . . . H59A H 0.1974 0.1267 0.3612 0.216 Uiso 1 1 calc R . . H59B H 0.2190 0.1757 0.3386 0.216 Uiso 1 1 calc R . . H59C H 0.2309 0.0917 0.3665 0.216 Uiso 1 1 calc R . . C60 C 0.1825(3) 0.0049(6) 0.3032(6) 0.155(6) Uani 1 1 d . . . H60A H 0.1751 -0.0276 0.2720 0.232 Uiso 1 1 calc R . . H60B H 0.1646 0.0183 0.3123 0.232 Uiso 1 1 calc R . . H60C H 0.1981 -0.0252 0.3312 0.232 Uiso 1 1 calc R . . C61 C 0.22903(14) 0.1039(4) 0.1411(2) 0.0353(14) Uani 1 1 d . . . H61 H 0.2085 0.1332 0.1285 0.042 Uiso 1 1 calc R . . C62 C 0.22557(18) 0.0351(4) 0.1038(3) 0.060(2) Uani 1 1 d . . . H62A H 0.2446 0.0021 0.1164 0.090 Uiso 1 1 calc R . . H62B H 0.2225 0.0568 0.0701 0.090 Uiso 1 1 calc R . . H62C H 0.2073 0.0024 0.1010 0.090 Uiso 1 1 calc R . . C63 C 0.25420(16) 0.1638(4) 0.1415(3) 0.0558(19) Uani 1 1 d . . . H63A H 0.2548 0.2086 0.1641 0.084 Uiso 1 1 calc R . . H63B H 0.2492 0.1838 0.1066 0.084 Uiso 1 1 calc R . . H63C H 0.2748 0.1374 0.1538 0.084 Uiso 1 1 calc R . . C64 C 0.15876(13) 0.3455(3) 0.1794(2) 0.0321(14) Uani 1 1 d . . . C65 C 0.15865(13) 0.3924(3) 0.1378(2) 0.0339(14) Uani 1 1 d . . . C66 C 0.15293(14) 0.4734(3) 0.1392(2) 0.0418(16) Uani 1 1 d . . . H66 H 0.1523 0.5063 0.1115 0.050 Uiso 1 1 calc R . . C67 C 0.14814(15) 0.5077(4) 0.1805(3) 0.0468(18) Uani 1 1 d . . . H67 H 0.1443 0.5635 0.1805 0.056 Uiso 1 1 calc R . . C68 C 0.14898(16) 0.4615(4) 0.2212(3) 0.0529(19) Uani 1 1 d . . . H68 H 0.1463 0.4860 0.2496 0.063 Uiso 1 1 calc R . . C69 C 0.15368(16) 0.3793(4) 0.2212(3) 0.0426(16) Uani 1 1 d . . . C70 C 0.1552(2) 0.3299(4) 0.2674(3) 0.071(3) Uani 1 1 d . . . H70 H 0.1552 0.2723 0.2579 0.086 Uiso 1 1 calc R . . C71 C 0.1264(3) 0.3437(5) 0.2799(4) 0.104(4) Uani 1 1 d . . . H71A H 0.1243 0.4009 0.2855 0.156 Uiso 1 1 calc R . . H71B H 0.1286 0.3140 0.3110 0.156 Uiso 1 1 calc R . . H71C H 0.1075 0.3251 0.2514 0.156 Uiso 1 1 calc R . . C72 C 0.1863(3) 0.3460(6) 0.3135(3) 0.100(3) Uani 1 1 d . . . H72A H 0.2042 0.3355 0.3036 0.151 Uiso 1 1 calc R . . H72B H 0.1877 0.3108 0.3419 0.151 Uiso 1 1 calc R . . H72C H 0.1869 0.4018 0.3242 0.151 Uiso 1 1 calc R . . C73 C 0.16592(16) 0.3543(3) 0.0958(2) 0.0415(16) Uani 1 1 d . . . H73 H 0.1583 0.2978 0.0927 0.050 Uiso 1 1 calc R . . C74 C 0.20141(18) 0.3513(4) 0.1098(3) 0.055(2) Uani 1 1 d . . . H74A H 0.2091 0.4049 0.1067 0.083 Uiso 1 1 calc R . . H74B H 0.2060 0.3147 0.0866 0.083 Uiso 1 1 calc R . . H74C H 0.2119 0.3324 0.1451 0.083 Uiso 1 1 calc R . . C75 C 0.1489(2) 0.3944(4) 0.0429(3) 0.065(2) Uani 1 1 d . . . H75A H 0.1262 0.3967 0.0350 0.098 Uiso 1 1 calc R . . H75B H 0.1526 0.3630 0.0165 0.098 Uiso 1 1 calc R . . H75C H 0.1571 0.4486 0.0436 0.098 Uiso 1 1 calc R . . C76 C 0.01133(14) -0.0838(4) 0.0748(3) 0.0463(17) Uani 1 1 d . . . H76A H 0.0096 -0.1165 0.1028 0.056 Uiso 1 1 calc R . . H76B H 0.0028 -0.1148 0.0426 0.056 Uiso 1 1 calc R . . C77 C -0.00582(15) -0.0076(4) 0.0695(3) 0.0504(18) Uani 1 1 d . . . H77A H -0.0248 -0.0146 0.0775 0.061 Uiso 1 1 calc R . . H77B H -0.0122 0.0142 0.0344 0.061 Uiso 1 1 calc R . . C78 C 0.01812(17) 0.0462(4) 0.1085(3) 0.062(2) Uani 1 1 d . . . H78A H 0.0138 0.1033 0.0991 0.074 Uiso 1 1 calc R . . H78B H 0.0184 0.0377 0.1432 0.074 Uiso 1 1 calc R . . C79 C 0.04871(16) 0.0198(4) 0.1054(3) 0.0490(17) Uani 1 1 d . . . H79A H 0.0541 0.0549 0.0818 0.059 Uiso 1 1 calc R . . H79B H 0.0660 0.0225 0.1397 0.059 Uiso 1 1 calc R . . C80 C 0.07966(19) 0.2710(4) 0.0553(3) 0.064(2) Uani 1 1 d . . . H80A H 0.0609 0.2436 0.0305 0.077 Uiso 1 1 calc R . . H80B H 0.0968 0.2688 0.0424 0.077 Uiso 1 1 calc R . . C81 C 0.0720(2) 0.3574(5) 0.0638(4) 0.093(3) Uani 1 1 d . . . H81A H 0.0910 0.3918 0.0742 0.112 Uiso 1 1 calc R . . H81B H 0.0554 0.3800 0.0327 0.112 Uiso 1 1 calc R . . C82 C 0.0607(3) 0.3477(6) 0.1060(5) 0.135(5) Uani 1 1 d . . . H82A H 0.0683 0.3929 0.1303 0.161 Uiso 1 1 calc R . . H82B H 0.0374 0.3476 0.0919 0.161 Uiso 1 1 calc R . . C83 C 0.0725(2) 0.2741(5) 0.1318(4) 0.095(3) Uani 1 1 d . . . H83A H 0.0549 0.2400 0.1316 0.114 Uiso 1 1 calc R . . H83B H 0.0867 0.2842 0.1678 0.114 Uiso 1 1 calc R . . C84 C -0.0038(2) 0.2899(6) 0.1425(4) 0.086(3) Uani 1 1 d . . . H84 H -0.0076 0.2373 0.1289 0.103 Uiso 1 1 calc R . . C85 C -0.0191(3) 0.3506(7) 0.1120(5) 0.104(4) Uani 1 1 d . . . H85 H -0.0323 0.3411 0.0772 0.125 Uiso 1 1 calc R . . C86 C -0.0151(3) 0.4277(7) 0.1319(5) 0.108(4) Uani 1 1 d . . . H86 H -0.0269 0.4713 0.1123 0.130 Uiso 1 1 calc R . . C87 C 0.0072(3) 0.4386(9) 0.1824(6) 0.125(4) Uani 1 1 d . . . H87 H 0.0115 0.4914 0.1955 0.151 Uiso 1 1 calc R . . C88 C 0.0230(4) 0.3752(9) 0.2138(6) 0.136(5) Uani 1 1 d . . . H88 H 0.0373 0.3836 0.2481 0.163 Uiso 1 1 calc R . . C89 C 0.0169(2) 0.2992(7) 0.1922(4) 0.090(3) Uani 1 1 d . . . C90 C 0.0332(3) 0.2316(8) 0.2224(5) 0.153(6) Uani 1 1 d . . . H90A H 0.0259 0.2226 0.2502 0.230 Uiso 1 1 calc R . . H90B H 0.0559 0.2423 0.2369 0.230 Uiso 1 1 calc R . . H90C H 0.0290 0.1840 0.2006 0.230 Uiso 1 1 calc R . . C93 C 0.1453(3) 0.3921(6) -0.1799(4) 0.103(3) Uiso 1 1 d D . . H93 H 0.1580 0.3667 -0.1950 0.124 Uiso 1 1 calc R . . C92 C 0.1151(3) 0.3905(7) -0.2083(4) 0.128(4) Uiso 1 1 d D . . H92 H 0.1061 0.3649 -0.2407 0.154 Uiso 1 1 calc R . . C94 C 0.1621(3) 0.4241(8) -0.1317(5) 0.155(5) Uiso 1 1 d D . . H94 H 0.1844 0.4208 -0.1157 0.186 Uiso 1 1 calc R . . C96 C 0.1125(3) 0.4632(7) -0.1355(5) 0.142(5) Uiso 1 1 d D . . H96 H 0.0999 0.4877 -0.1197 0.170 Uiso 1 1 calc R . . C91 C 0.0979(4) 0.4310(11) -0.1849(7) 0.210(8) Uiso 1 1 d D . . C95 C 0.1448(4) 0.4597(10) -0.1097(5) 0.211(8) Uiso 1 1 d D . . H95 H 0.1545 0.4826 -0.0765 0.253 Uiso 1 1 calc R . . C97 C 0.0652(4) 0.4265(16) -0.2058(9) 0.367(16) Uiso 1 1 d D . . H97A H 0.0570 0.4548 -0.2387 0.550 Uiso 1 1 calc R . . H97B H 0.0568 0.4512 -0.1824 0.550 Uiso 1 1 calc R . . H97C H 0.0587 0.3703 -0.2112 0.550 Uiso 1 1 calc R . . 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 0.02926(13) 0.02492(12) 0.02638(11) -0.00047(8) 0.01195(9) 0.00126(9) Cl1 0.0547(10) 0.0298(8) 0.0375(8) -0.0028(6) 0.0295(7) 0.0004(7) O1 0.036(3) 0.039(2) 0.049(3) -0.0063(19) 0.023(2) -0.001(2) N1 0.031(3) 0.025(3) 0.031(3) 0.0056(19) 0.017(2) 0.000(2) C1 0.027(3) 0.031(3) 0.031(3) 0.002(2) 0.007(3) 0.005(3) Bi2 0.02746(12) 0.03049(12) 0.02119(10) -0.00076(8) 0.01233(8) 0.00211(9) Cl2 0.0425(9) 0.0425(9) 0.0397(8) -0.0062(7) 0.0103(7) 0.0014(7) O2 0.054(3) 0.067(3) 0.054(3) 0.010(2) 0.025(3) 0.030(3) N2 0.033(3) 0.034(3) 0.031(3) -0.002(2) 0.017(2) -0.001(2) C2 0.030(3) 0.038(4) 0.038(3) 0.006(3) 0.018(3) 0.006(3) Bi3 0.02421(12) 0.02389(11) 0.02250(10) -0.00013(8) 0.01041(8) -0.00066(9) Cl3 0.0399(9) 0.0319(8) 0.0318(8) -0.0040(6) 0.0112(7) -0.0010(7) N3 0.023(3) 0.027(2) 0.026(2) -0.0028(19) 0.011(2) 0.000(2) C3 0.044(4) 0.036(4) 0.038(3) 0.011(3) 0.020(3) 0.009(3) Cl4 0.0288(8) 0.0485(9) 0.0336(8) 0.0064(6) 0.0185(6) 0.0060(7) N4 0.022(2) 0.040(3) 0.018(2) 0.0015(19) 0.0083(19) -0.002(2) C4 0.055(5) 0.063(5) 0.046(4) 0.014(3) 0.031(4) 0.021(4) Cl5 0.0377(9) 0.0537(10) 0.0315(8) -0.0006(6) 0.0209(7) -0.0091(7) N5 0.022(2) 0.026(3) 0.021(2) 0.0011(18) 0.0085(19) -0.003(2) C5 0.043(4) 0.064(5) 0.081(6) 0.026(4) 0.041(4) 0.007(4) Cl6 0.0467(9) 0.0276(8) 0.0309(7) 0.0027(6) 0.0100(7) 0.0033(7) N6 0.027(3) 0.025(3) 0.032(3) -0.005(2) 0.012(2) -0.003(2) C6 0.037(4) 0.048(4) 0.092(6) 0.015(4) 0.041(4) 0.000(3) C7 0.029(4) 0.042(4) 0.061(4) 0.010(3) 0.023(3) 0.006(3) C8 0.062(5) 0.060(5) 0.028(3) -0.002(3) 0.025(3) -0.004(4) C9 0.113(7) 0.052(5) 0.062(5) -0.016(4) 0.060(5) -0.018(5) C10 0.059(5) 0.084(6) 0.037(4) -0.002(4) 0.006(4) -0.019(4) C11 0.039(4) 0.037(4) 0.074(5) 0.000(3) 0.025(4) -0.001(3) C12 0.036(5) 0.089(7) 0.093(7) -0.028(5) 0.015(4) -0.012(4) C13 0.080(6) 0.029(4) 0.125(8) -0.003(4) 0.059(6) -0.006(4) C14 0.029(3) 0.023(3) 0.042(3) 0.002(2) 0.018(3) 0.005(2) C15 0.031(3) 0.029(3) 0.039(3) 0.006(2) 0.017(3) 0.000(3) C16 0.030(4) 0.037(4) 0.048(4) 0.006(3) 0.015(3) 0.005(3) C17 0.036(4) 0.038(4) 0.061(5) 0.007(3) 0.025(3) 0.015(3) C18 0.048(4) 0.037(4) 0.044(4) -0.004(3) 0.028(3) 0.010(3) C19 0.043(4) 0.025(3) 0.037(3) 0.001(2) 0.018(3) 0.001(3) C20 0.037(4) 0.033(3) 0.043(4) -0.008(3) 0.011(3) 0.005(3) C21 0.071(6) 0.097(7) 0.040(4) -0.018(4) 0.014(4) 0.010(5) C22 0.049(5) 0.049(5) 0.076(6) 0.004(4) -0.004(4) -0.005(4) C23 0.030(3) 0.036(4) 0.040(4) -0.001(3) 0.008(3) 0.004(3) C24 0.044(4) 0.044(4) 0.092(6) -0.017(4) 0.023(4) -0.003(3) C25 0.072(5) 0.046(4) 0.035(4) -0.002(3) 0.004(4) 0.015(4) C26 0.026(3) 0.037(3) 0.023(3) -0.006(2) 0.011(2) -0.007(3) C27 0.026(3) 0.066(4) 0.020(3) -0.002(3) 0.015(2) -0.008(3) C28 0.030(4) 0.076(5) 0.026(3) 0.008(3) 0.018(3) 0.013(3) C29 0.031(4) 0.113(7) 0.029(4) 0.008(4) 0.014(3) 0.020(4) C30 0.027(4) 0.170(9) 0.025(4) 0.003(5) 0.012(3) -0.002(5) C31 0.045(5) 0.107(7) 0.028(4) -0.015(4) 0.018(3) -0.034(5) C32 0.041(4) 0.064(5) 0.023(3) -0.001(3) 0.016(3) -0.017(3) C33 0.069(5) 0.056(5) 0.033(4) -0.006(3) 0.020(3) -0.036(4) C34 0.097(6) 0.038(4) 0.051(4) -0.008(3) 0.045(4) -0.012(4) C35 0.133(8) 0.084(6) 0.049(5) -0.014(4) 0.037(5) -0.076(6) C36 0.040(4) 0.055(4) 0.040(4) 0.003(3) 0.017(3) 0.020(3) C37 0.060(5) 0.064(5) 0.060(5) 0.008(4) 0.028(4) 0.012(4) C38 0.074(6) 0.088(6) 0.052(5) -0.002(4) 0.026(4) 0.038(5) C39 0.028(3) 0.039(3) 0.021(3) -0.008(2) 0.014(2) -0.002(3) C40 0.030(3) 0.040(3) 0.024(3) -0.004(2) 0.010(2) 0.008(3) C41 0.031(4) 0.047(4) 0.038(4) -0.002(3) 0.011(3) 0.014(3) C42 0.031(4) 0.070(5) 0.058(4) -0.006(4) 0.028(3) -0.004(4) C43 0.037(4) 0.053(4) 0.035(3) -0.008(3) 0.020(3) -0.006(3) C44 0.027(3) 0.044(4) 0.027(3) -0.004(3) 0.013(3) -0.006(3) C45 0.045(4) 0.040(4) 0.039(4) 0.006(3) 0.023(3) 0.012(3) C46 0.057(5) 0.041(4) 0.052(4) -0.002(3) 0.025(4) 0.000(3) C47 0.066(5) 0.056(4) 0.042(4) 0.010(3) 0.023(4) 0.020(4) C48 0.030(3) 0.031(3) 0.036(3) -0.001(3) 0.014(3) -0.007(3) C49 0.048(4) 0.047(4) 0.046(4) -0.012(3) 0.021(3) -0.009(3) C50 0.042(4) 0.052(4) 0.040(4) 0.000(3) 0.017(3) -0.003(3) C51 0.029(3) 0.035(3) 0.024(3) -0.002(2) 0.013(2) -0.006(3) C52 0.018(3) 0.027(3) 0.025(3) -0.003(2) 0.003(2) -0.006(2) C53 0.026(3) 0.032(3) 0.028(3) -0.007(2) 0.005(2) -0.005(3) C54 0.025(3) 0.037(4) 0.041(4) -0.009(3) 0.007(3) 0.004(3) C55 0.030(4) 0.038(4) 0.044(4) 0.005(3) 0.000(3) 0.009(3) C56 0.031(4) 0.045(4) 0.034(3) 0.015(3) 0.007(3) 0.000(3) C57 0.028(3) 0.035(3) 0.032(3) 0.007(3) 0.011(3) -0.005(3) C58 0.032(4) 0.067(5) 0.028(3) 0.023(3) 0.017(3) 0.007(3) C59 0.058(6) 0.301(17) 0.086(8) -0.089(9) 0.042(6) -0.012(8) C60 0.138(11) 0.100(8) 0.303(19) 0.087(10) 0.170(12) 0.013(7) C61 0.027(3) 0.051(4) 0.027(3) -0.003(3) 0.010(3) 0.011(3) C62 0.060(5) 0.077(5) 0.036(4) -0.019(4) 0.011(3) 0.011(4) C63 0.050(5) 0.078(5) 0.040(4) 0.010(4) 0.018(3) -0.013(4) C64 0.023(3) 0.025(3) 0.046(4) -0.011(3) 0.011(3) -0.007(2) C65 0.029(3) 0.027(3) 0.037(3) -0.003(3) 0.003(3) -0.006(3) C66 0.039(4) 0.028(3) 0.047(4) 0.004(3) 0.003(3) -0.008(3) C67 0.042(4) 0.020(3) 0.074(5) -0.004(3) 0.019(4) 0.005(3) C68 0.058(5) 0.038(4) 0.077(5) -0.015(4) 0.041(4) -0.004(3) C69 0.049(4) 0.034(4) 0.052(4) -0.006(3) 0.028(3) -0.006(3) C70 0.132(8) 0.041(4) 0.074(6) -0.017(4) 0.078(6) -0.019(5) C71 0.158(10) 0.074(6) 0.136(9) -0.041(6) 0.119(8) -0.039(6) C72 0.158(10) 0.105(7) 0.043(5) -0.005(5) 0.044(6) -0.021(7) C73 0.061(5) 0.027(3) 0.034(3) 0.000(3) 0.016(3) -0.011(3) C74 0.069(5) 0.054(5) 0.059(5) -0.010(3) 0.042(4) -0.011(4) C75 0.110(7) 0.035(4) 0.044(4) 0.001(3) 0.022(4) -0.010(4) C76 0.036(4) 0.045(4) 0.061(4) -0.007(3) 0.022(3) -0.004(3) C77 0.033(4) 0.067(5) 0.053(4) 0.004(4) 0.018(3) 0.010(3) C78 0.058(5) 0.057(5) 0.080(6) -0.016(4) 0.036(4) -0.002(4) C79 0.056(5) 0.044(4) 0.059(4) -0.014(3) 0.036(4) -0.013(3) C80 0.066(5) 0.066(5) 0.048(5) 0.004(4) 0.010(4) 0.026(4) C81 0.102(8) 0.067(6) 0.099(8) 0.015(5) 0.026(6) 0.033(5) C82 0.218(14) 0.072(7) 0.202(13) 0.064(7) 0.178(12) 0.070(8) C83 0.120(8) 0.073(6) 0.134(9) 0.030(6) 0.095(7) 0.052(6) C84 0.057(6) 0.103(8) 0.096(8) 0.023(6) 0.027(6) -0.004(6) C85 0.090(8) 0.100(9) 0.126(10) -0.006(8) 0.045(7) 0.017(7) C86 0.112(9) 0.083(8) 0.126(10) -0.007(7) 0.042(8) -0.007(7) C87 0.134(12) 0.112(11) 0.142(13) -0.037(9) 0.065(10) -0.029(9) C88 0.196(16) 0.103(10) 0.160(14) -0.026(10) 0.124(13) -0.018(10) C89 0.080(7) 0.116(9) 0.092(8) 0.029(7) 0.051(6) 0.013(7) C90 0.133(11) 0.208(14) 0.152(12) 0.106(11) 0.091(10) 0.062(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Bi1 N2 2.333(5) . ? Bi1 N1 2.359(4) . ? Bi1 Cl2 2.4892(17) . ? Bi1 O1 2.624(4) . ? Bi1 Cl1 2.7953(16) . ? Bi1 Cl6 3.1874(17) . ? Cl1 Bi2 2.7460(15) . ? O1 C79 1.440(7) . ? O1 C76 1.471(7) . ? N1 C1 1.313(7) . ? N1 C2 1.417(7) . ? C1 N2 1.314(7) . ? Bi2 N4 2.256(4) . ? Bi2 N3 2.443(4) . ? Bi2 Cl4 2.5876(15) . ? Bi2 Cl3 2.6220(15) . ? Bi2 Cl6 3.3731(16) . ? O2 C80 1.419(8) . ? O2 C83 1.438(9) . ? O2 Bi3 2.574(4) . ? N2 C14 1.434(7) . ? C2 C7 1.403(8) . ? C2 C3 1.412(8) . ? Bi3 N5 2.291(4) . ? Bi3 N6 2.392(4) . ? Bi3 Cl5 2.4746(15) . ? Bi3 Cl6 2.7504(15) . ? Bi3 Cl3 3.3146(16) . ? N3 C26 1.306(6) . ? N3 C39 1.409(7) . ? C3 C4 1.405(8) . ? C3 C8 1.510(9) . ? N4 C26 1.328(7) . ? N4 C27 1.432(7) . ? C4 C5 1.392(10) . ? N5 C51 1.323(6) . ? N5 C52 1.437(6) . ? C5 C6 1.371(10) . ? N6 C51 1.309(7) . ? N6 C64 1.429(7) . ? C6 C7 1.398(9) . ? C7 C11 1.510(9) . ? C8 C9 1.532(9) . ? C8 C10 1.536(9) . ? C11 C12 1.528(9) . ? C11 C13 1.541(9) . ? C14 C15 1.404(8) . ? C14 C19 1.406(8) . ? C15 C16 1.397(8) . ? C15 C23 1.521(8) . ? C16 C17 1.392(9) . ? C17 C18 1.378(9) . ? C18 C19 1.396(8) . ? C19 C20 1.522(8) . ? C20 C21 1.531(9) . ? C20 C22 1.532(9) . ? C23 C25 1.538(8) . ? C23 C24 1.546(9) . ? C27 C32 1.393(8) . ? C27 C28 1.419(8) . ? C28 C29 1.385(8) . ? C28 C36 1.500(9) . ? C29 C30 1.378(11) . ? C30 C31 1.364(11) . ? C31 C32 1.414(9) . ? C32 C33 1.504(10) . ? C33 C34 1.497(9) . ? C33 C35 1.558(9) . ? C36 C37 1.535(9) . ? C36 C38 1.542(8) . ? C39 C40 1.407(8) . ? C39 C44 1.408(8) . ? C40 C41 1.393(8) . ? C40 C45 1.529(8) . ? C41 C42 1.379(9) . ? C42 C43 1.384(9) . ? C43 C44 1.378(8) . ? C44 C48 1.528(8) . ? C45 C46 1.531(8) . ? C45 C47 1.541(8) . ? C48 C49 1.521(8) . ? C48 C50 1.530(8) . ? C52 C53 1.401(8) . ? C52 C57 1.409(7) . ? C53 C54 1.411(8) . ? C53 C61 1.509(8) . ? C54 C55 1.363(8) . ? C55 C56 1.373(9) . ? C56 C57 1.384(8) . ? C57 C58 1.508(8) . ? C58 C60 1.488(10) . ? C58 C59 1.504(10) . ? C61 C62 1.528(8) . ? C61 C63 1.529(9) . ? C64 C69 1.409(8) . ? C64 C65 1.415(8) . ? C65 C66 1.383(8) . ? C65 C73 1.496(8) . ? C66 C67 1.393(9) . ? C67 C68 1.376(9) . ? C68 C69 1.393(8) . ? C69 C70 1.525(9) . ? C70 C71 1.521(11) . ? C70 C72 1.543(12) . ? C73 C74 1.526(9) . ? C73 C75 1.551(9) . ? C76 C77 1.475(9) . ? C77 C78 1.518(9) . ? C78 C79 1.510(9) . ? C80 C81 1.529(10) . ? C81 C82 1.484(13) . ? C82 C83 1.428(11) . ? C84 C85 1.343(12) . ? C84 C89 1.369(13) . ? C85 C86 1.391(13) . ? C86 C87 1.411(15) . ? C87 C88 1.395(17) . ? C88 C89 1.391(14) . ? C89 C90 1.442(13) . ? C93 C92 1.310(11) . ? C93 C94 1.389(12) . ? C92 C91 1.390(13) . ? C94 C95 1.328(14) . ? C96 C95 1.384(13) . ? C96 C91 1.402(13) . ? C91 C97 1.391(15) . ? 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 N2 Bi1 N1 56.89(16) . . ? N2 Bi1 Cl2 94.69(12) . . ? N1 Bi1 Cl2 89.92(12) . . ? N2 Bi1 O1 136.26(15) . . ? N1 Bi1 O1 79.38(14) . . ? Cl2 Bi1 O1 84.21(10) . . ? N2 Bi1 Cl1 77.21(12) . . ? N1 Bi1 Cl1 133.72(11) . . ? Cl2 Bi1 Cl1 88.10(5) . . ? O1 Bi1 Cl1 146.09(10) . . ? N2 Bi1 Cl6 93.13(12) . . ? N1 Bi1 Cl6 102.48(11) . . ? Cl2 Bi1 Cl6 167.54(5) . . ? O1 Bi1 Cl6 96.78(9) . . ? Cl1 Bi1 Cl6 84.18(4) . . ? Bi2 Cl1 Bi1 94.13(4) . . ? C79 O1 C76 108.2(4) . . ? C79 O1 Bi1 120.0(3) . . ? C76 O1 Bi1 131.0(3) . . ? C1 N1 C2 123.4(5) . . ? C1 N1 Bi1 92.7(3) . . ? C2 N1 Bi1 142.7(4) . . ? N1 C1 N2 116.6(5) . . ? N4 Bi2 N3 56.63(15) . . ? N4 Bi2 Cl4 86.21(12) . . ? N3 Bi2 Cl4 142.70(11) . . ? N4 Bi2 Cl3 94.05(12) . . ? N3 Bi2 Cl3 90.15(10) . . ? Cl4 Bi2 Cl3 89.38(5) . . ? N4 Bi2 Cl1 90.57(12) . . ? N3 Bi2 Cl1 93.90(10) . . ? Cl4 Bi2 Cl1 89.13(5) . . ? Cl3 Bi2 Cl1 175.04(4) . . ? N4 Bi2 Cl6 160.88(11) . . ? N3 Bi2 Cl6 140.83(11) . . ? Cl4 Bi2 Cl6 76.38(5) . . ? Cl3 Bi2 Cl6 93.60(4) . . ? Cl1 Bi2 Cl6 81.45(4) . . ? C80 O2 C83 108.4(6) . . ? C80 O2 Bi3 121.3(4) . . ? C83 O2 Bi3 129.3(5) . . ? C1 N2 C14 123.5(5) . . ? C1 N2 Bi1 93.8(3) . . ? C14 N2 Bi1 141.6(4) . . ? C7 C2 C3 121.5(6) . . ? C7 C2 N1 120.4(5) . . ? C3 C2 N1 118.0(5) . . ? N5 Bi3 N6 57.05(15) . . ? N5 Bi3 Cl5 93.17(11) . . ? N6 Bi3 Cl5 90.12(11) . . ? N5 Bi3 O2 137.96(15) . . ? N6 Bi3 O2 81.28(16) . . ? Cl5 Bi3 O2 80.58(12) . . ? N5 Bi3 Cl6 85.36(11) . . ? N6 Bi3 Cl6 142.37(11) . . ? Cl5 Bi3 Cl6 90.40(5) . . ? O2 Bi3 Cl6 135.77(12) . . ? N5 Bi3 Cl3 92.87(11) . . ? N6 Bi3 Cl3 91.10(11) . . ? Cl5 Bi3 Cl3 173.47(4) . . ? O2 Bi3 Cl3 93.27(11) . . ? Cl6 Bi3 Cl3 92.55(4) . . ? Bi2 Cl3 Bi3 84.68(4) . . ? C26 N3 C39 124.7(5) . . ? C26 N3 Bi2 89.7(3) . . ? C39 N3 Bi2 142.7(3) . . ? C4 C3 C2 117.8(6) . . ? C4 C3 C8 122.1(6) . . ? C2 C3 C8 120.0(5) . . ? C26 N4 C27 124.5(4) . . ? C26 N4 Bi2 97.6(3) . . ? C27 N4 Bi2 136.5(3) . . ? C5 C4 C3 120.3(7) . . ? C51 N5 C52 123.1(4) . . ? C51 N5 Bi3 95.3(3) . . ? C52 N5 Bi3 141.6(3) . . ? C6 C5 C4 121.1(7) . . ? Bi3 Cl6 Bi1 119.67(5) . . ? Bi3 Cl6 Bi2 81.66(3) . . ? Bi1 Cl6 Bi2 76.35(4) . . ? C51 N6 C64 125.2(5) . . ? C51 N6 Bi3 91.1(3) . . ? C64 N6 Bi3 143.7(4) . . ? C5 C6 C7 120.7(7) . . ? C6 C7 C2 118.4(6) . . ? C6 C7 C11 118.5(6) . . ? C2 C7 C11 123.1(6) . . ? C3 C8 C9 113.9(6) . . ? C3 C8 C10 109.5(5) . . ? C9 C8 C10 110.8(6) . . ? C7 C11 C12 112.8(6) . . ? C7 C11 C13 111.1(6) . . ? C12 C11 C13 110.5(6) . . ? C15 C14 C19 121.9(5) . . ? C15 C14 N2 119.9(5) . . ? C19 C14 N2 118.2(5) . . ? C16 C15 C14 118.0(5) . . ? C16 C15 C23 118.8(5) . . ? C14 C15 C23 123.2(5) . . ? C17 C16 C15 121.0(6) . . ? C18 C17 C16 119.6(6) . . ? C17 C18 C19 121.8(6) . . ? C18 C19 C14 117.5(6) . . ? C18 C19 C20 120.9(5) . . ? C14 C19 C20 121.5(5) . . ? C19 C20 C21 113.9(6) . . ? C19 C20 C22 109.2(5) . . ? C21 C20 C22 110.9(6) . . ? C15 C23 C25 110.7(5) . . ? C15 C23 C24 111.5(5) . . ? C25 C23 C24 110.7(5) . . ? N3 C26 N4 116.1(5) . . ? C32 C27 C28 121.9(6) . . ? C32 C27 N4 120.1(6) . . ? C28 C27 N4 118.0(5) . . ? C29 C28 C27 117.8(7) . . ? C29 C28 C36 121.1(6) . . ? C27 C28 C36 121.0(5) . . ? C30 C29 C28 121.1(7) . . ? C31 C30 C29 120.8(7) . . ? C30 C31 C32 121.2(7) . . ? C27 C32 C31 117.2(7) . . ? C27 C32 C33 123.0(6) . . ? C31 C32 C33 119.7(6) . . ? C34 C33 C32 112.7(5) . . ? C34 C33 C35 109.5(6) . . ? C32 C33 C35 112.3(7) . . ? C28 C36 C37 109.4(5) . . ? C28 C36 C38 114.3(6) . . ? C37 C36 C38 109.8(6) . . ? C40 C39 C44 121.0(5) . . ? C40 C39 N3 117.4(5) . . ? C44 C39 N3 121.3(5) . . ? C41 C40 C39 118.5(6) . . ? C41 C40 C45 122.1(5) . . ? C39 C40 C45 119.4(5) . . ? C42 C41 C40 120.5(6) . . ? C41 C42 C43 120.3(6) . . ? C44 C43 C42 121.4(6) . . ? C43 C44 C39 118.2(6) . . ? C43 C44 C48 119.2(5) . . ? C39 C44 C48 122.5(5) . . ? C40 C45 C46 112.0(5) . . ? C40 C45 C47 113.6(5) . . ? C46 C45 C47 109.6(5) . . ? C49 C48 C44 113.4(5) . . ? C49 C48 C50 109.8(5) . . ? C44 C48 C50 110.9(5) . . ? N6 C51 N5 116.5(5) . . ? C53 C52 C57 122.5(5) . . ? C53 C52 N5 118.8(5) . . ? C57 C52 N5 118.7(5) . . ? C52 C53 C54 117.1(5) . . ? C52 C53 C61 123.1(5) . . ? C54 C53 C61 119.9(5) . . ? C55 C54 C53 121.0(6) . . ? C54 C55 C56 120.5(6) . . ? C55 C56 C57 122.1(6) . . ? C56 C57 C52 116.9(5) . . ? C56 C57 C58 121.6(5) . . ? C52 C57 C58 121.4(5) . . ? C60 C58 C59 108.1(8) . . ? C60 C58 C57 111.4(6) . . ? C59 C58 C57 112.4(6) . . ? C53 C61 C62 111.9(5) . . ? C53 C61 C63 111.9(5) . . ? C62 C61 C63 111.9(6) . . ? C69 C64 C65 121.9(5) . . ? C69 C64 N6 119.8(5) . . ? C65 C64 N6 118.2(5) . . ? C66 C65 C64 117.2(6) . . ? C66 C65 C73 123.0(6) . . ? C64 C65 C73 119.7(5) . . ? C65 C66 C67 121.5(6) . . ? C68 C67 C66 120.6(6) . . ? C67 C68 C69 120.6(6) . . ? C68 C69 C64 118.2(6) . . ? C68 C69 C70 119.4(6) . . ? C64 C69 C70 122.3(6) . . ? C71 C70 C69 111.2(8) . . ? C71 C70 C72 112.7(7) . . ? C69 C70 C72 110.5(7) . . ? C65 C73 C74 110.7(5) . . ? C65 C73 C75 113.5(6) . . ? C74 C73 C75 110.8(6) . . ? O1 C76 C77 105.4(5) . . ? C76 C77 C78 103.2(6) . . ? C79 C78 C77 102.5(6) . . ? O1 C79 C78 107.1(5) . . ? O2 C80 C81 103.9(6) . . ? C82 C81 C80 101.4(7) . . ? C83 C82 C81 109.0(7) . . ? C82 C83 O2 106.6(7) . . ? C85 C84 C89 123.9(11) . . ? C84 C85 C86 119.1(12) . . ? C85 C86 C87 117.4(12) . . ? C88 C87 C86 123.0(13) . . ? C89 C88 C87 116.5(14) . . ? C84 C89 C88 119.9(11) . . ? C84 C89 C90 121.0(12) . . ? C88 C89 C90 119.0(13) . . ? C92 C93 C94 131.9(11) . . ? C93 C92 C91 111.2(11) . . ? C95 C94 C93 115.2(13) . . ? C95 C96 C91 120.9(12) . . ? C92 C91 C97 119.5(14) . . ? C92 C91 C96 121.4(13) . . ? C97 C91 C96 117.8(14) . . ? C94 C95 C96 119.3(12) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.238 _refine_diff_density_min -1.966 _refine_diff_density_rms 0.162