# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'K. C. Kumara Swamy' _publ_contact_author_email KCKSSC@UOHYD.ERNET.IN _publ_section_title ; Coordinatively polymeric and monomeric bismuth(III) complexes with pyridine carboxylic acids ; loop_ _publ_author_name 'K. C. Kumara Swamy' 'O. Anjaneyulu' 'T. K. Prasad' # Attachment 'kckman.cif' data_compd1 _database_code_depnum_ccdc_archive 'CCDC 749253' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H12 Bi N3 O6' _chemical_formula_weight 575.29 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 11.822(3) _cell_length_b 7.738(2) _cell_length_c 18.931(6) _cell_angle_alpha 90.00 _cell_angle_beta 91.165(4) _cell_angle_gamma 90.00 _cell_volume 1731.3(9) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 6537 _cell_measurement_theta_min 2.73 _cell_measurement_theta_max 28.29 _exptl_crystal_description Prism _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.207 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 10.228 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.1054 _exptl_absorpt_correction_T_max 0.1762 _exptl_absorpt_process_details Sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8676 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0338 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3371 _reflns_number_gt 2888 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0373P)^2^+5.7618P] 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 3371 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0408 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.0852 _refine_ls_wR_factor_gt 0.0822 _refine_ls_goodness_of_fit_ref 1.116 _refine_ls_restrained_S_all 1.116 _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 Bi Bi 0.258800(17) 0.25451(2) 0.217143(10) 0.01961(10) Uani 1 1 d . . . C1 C 0.0318(5) 0.0793(8) 0.1180(3) 0.0290(14) Uani 1 1 d . . . H1 H 0.0642 -0.0232 0.1342 0.035 Uiso 1 1 calc R . . C2 C -0.0604(6) 0.0707(9) 0.0719(4) 0.0380(17) Uani 1 1 d . . . H2 H -0.0900 -0.0354 0.0578 0.046 Uiso 1 1 calc R . . C3 C -0.1075(7) 0.2227(9) 0.0475(4) 0.0424(18) Uani 1 1 d . . . H3 H -0.1683 0.2209 0.0155 0.051 Uiso 1 1 calc R . . C4 C -0.0630(6) 0.3778(9) 0.0710(4) 0.0369(16) Uani 1 1 d . . . H4 H -0.0935 0.4820 0.0552 0.044 Uiso 1 1 calc R . . C5 C 0.0266(5) 0.3763(7) 0.1181(3) 0.0252(13) Uani 1 1 d . . . C6 C 0.0754(5) 0.5422(7) 0.1470(3) 0.0277(13) Uani 1 1 d . . . C7 C 0.5317(6) 0.0685(8) 0.1975(3) 0.0310(15) Uani 1 1 d . . . H7 H 0.4891 -0.0326 0.1976 0.037 Uiso 1 1 calc R . . C8 C 0.6472(6) 0.0573(9) 0.1910(4) 0.0367(16) Uani 1 1 d . . . H8 H 0.6819 -0.0501 0.1872 0.044 Uiso 1 1 calc R . . C9 C 0.7104(6) 0.2050(10) 0.1902(4) 0.0392(16) Uani 1 1 d . . . H9 H 0.7887 0.1995 0.1864 0.047 Uiso 1 1 calc R . . C10 C 0.6561(5) 0.3630(9) 0.1952(3) 0.0313(14) Uani 1 1 d . . . H10 H 0.6971 0.4654 0.1928 0.038 Uiso 1 1 calc R . . C11 C 0.5413(5) 0.3668(7) 0.2036(3) 0.0225(12) Uani 1 1 d . . . C12 C 0.4792(5) 0.5348(7) 0.2131(3) 0.0240(13) Uani 1 1 d . . . C13 C 0.3222(6) 0.4416(8) 0.0626(4) 0.0331(15) Uani 1 1 d . . . H13 H 0.3096 0.5426 0.0879 0.040 Uiso 1 1 calc R . . C14 C 0.3554(6) 0.4521(9) -0.0069(4) 0.0392(17) Uani 1 1 d . . . H14 H 0.3642 0.5589 -0.0286 0.047 Uiso 1 1 calc R . . C15 C 0.3752(8) 0.3008(11) -0.0433(4) 0.049(2) Uani 1 1 d . . . H15 H 0.3974 0.3045 -0.0901 0.058 Uiso 1 1 calc R . . C16 C 0.3619(7) 0.1443(9) -0.0097(4) 0.0398(17) Uani 1 1 d . . . H16 H 0.3755 0.0413 -0.0334 0.048 Uiso 1 1 calc R . . C17 C 0.3282(5) 0.1429(8) 0.0596(3) 0.0262(13) Uani 1 1 d . . . C18 C 0.3117(5) -0.0250(8) 0.0986(3) 0.0281(14) Uani 1 1 d . . . N1 N 0.0762(4) 0.2289(6) 0.1401(3) 0.0225(11) Uani 1 1 d . . . N2 N 0.4785(4) 0.2217(6) 0.2039(3) 0.0223(11) Uani 1 1 d . . . N3 N 0.3078(4) 0.2885(6) 0.0942(3) 0.0231(11) Uani 1 1 d . . . O1 O 0.1604(3) 0.5252(5) 0.1899(2) 0.0279(9) Uani 1 1 d . . . O2 O 0.0325(5) 0.6807(6) 0.1286(3) 0.0527(15) Uani 1 1 d . . . O3 O 0.3742(3) 0.5224(5) 0.2254(2) 0.0272(9) Uani 1 1 d . . . O4 O 0.5336(4) 0.6706(5) 0.2111(3) 0.0383(11) Uani 1 1 d . . . O5 O 0.2797(4) -0.0121(5) 0.1635(2) 0.0263(9) Uani 1 1 d . . . O6 O 0.3301(5) -0.1601(6) 0.0682(3) 0.0457(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi 0.02340(15) 0.01517(14) 0.02029(14) -0.00077(8) 0.00068(9) 0.00023(8) C1 0.028(4) 0.027(3) 0.032(4) -0.005(3) -0.001(3) -0.002(3) C2 0.036(4) 0.037(4) 0.041(4) -0.015(3) -0.002(3) -0.009(3) C3 0.035(4) 0.048(4) 0.044(4) -0.015(3) -0.009(3) -0.003(3) C4 0.032(4) 0.043(4) 0.034(4) 0.000(3) -0.014(3) 0.001(3) C5 0.030(4) 0.025(3) 0.021(3) 0.003(2) 0.003(3) 0.000(2) C6 0.026(3) 0.025(3) 0.032(3) 0.000(3) 0.001(3) 0.002(2) C7 0.036(4) 0.023(3) 0.034(4) 0.001(3) -0.004(3) 0.005(3) C8 0.033(4) 0.033(3) 0.044(4) -0.003(3) -0.004(3) 0.012(3) C9 0.018(3) 0.055(4) 0.044(4) -0.004(4) 0.003(3) 0.010(3) C10 0.022(3) 0.036(3) 0.036(4) 0.000(3) 0.002(3) -0.004(3) C11 0.021(3) 0.026(3) 0.020(3) 0.001(2) 0.001(2) 0.002(2) C12 0.028(3) 0.025(3) 0.019(3) 0.002(2) -0.002(3) 0.002(2) C13 0.033(4) 0.030(3) 0.036(4) 0.000(3) -0.004(3) -0.001(3) C14 0.052(5) 0.032(3) 0.033(4) 0.013(3) 0.008(3) 0.002(3) C15 0.069(6) 0.055(4) 0.023(4) 0.004(3) 0.014(4) 0.011(4) C16 0.055(5) 0.032(3) 0.033(4) -0.009(3) 0.007(3) 0.006(3) C17 0.030(4) 0.025(3) 0.024(3) -0.004(2) -0.002(3) 0.002(2) C18 0.024(3) 0.027(3) 0.033(4) -0.003(3) -0.004(3) -0.003(2) N1 0.024(3) 0.022(2) 0.022(3) -0.0002(19) -0.002(2) -0.0015(19) N2 0.020(3) 0.019(2) 0.028(3) 0.002(2) 0.001(2) 0.0023(19) N3 0.025(3) 0.026(2) 0.019(3) 0.005(2) 0.001(2) 0.005(2) O1 0.025(2) 0.028(2) 0.030(2) -0.0074(18) -0.0114(18) 0.0000(17) O2 0.061(4) 0.028(2) 0.068(4) 0.008(3) -0.030(3) 0.004(2) O3 0.016(2) 0.027(2) 0.038(3) -0.0039(19) 0.0013(18) 0.0009(16) O4 0.037(3) 0.024(2) 0.054(3) -0.001(2) 0.006(2) -0.010(2) O5 0.028(2) 0.026(2) 0.025(2) 0.0017(17) 0.0025(18) 0.0005(17) O6 0.072(4) 0.024(2) 0.041(3) -0.010(2) 0.004(3) 0.004(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 Bi O5 2.315(4) . ? Bi N3 2.425(5) . ? Bi O1 2.446(4) . ? Bi O3 2.484(4) . ? Bi N1 2.588(5) . ? Bi N2 2.627(5) . ? Bi O3 2.636(4) 2_545 ? Bi O1 2.662(4) 2_545 ? C1 N1 1.334(7) . ? C1 C2 1.384(9) . ? C1 H1 0.9300 . ? C2 C3 1.377(10) . ? C2 H2 0.9300 . ? C3 C4 1.381(9) . ? C3 H3 0.9300 . ? C4 C5 1.371(9) . ? C4 H4 0.9300 . ? C5 N1 1.344(7) . ? C5 C6 1.506(8) . ? C6 O2 1.233(7) . ? C6 O1 1.285(7) . ? C7 N2 1.348(7) . ? C7 C8 1.377(9) . ? C7 H7 0.9300 . ? C8 C9 1.366(10) . ? C8 H8 0.9300 . ? C9 C10 1.386(9) . ? C9 H9 0.9300 . ? C10 C11 1.370(8) . ? C10 H10 0.9300 . ? C11 N2 1.346(7) . ? C11 C12 1.506(8) . ? C12 O4 1.233(7) . ? C12 O3 1.272(7) . ? C13 N3 1.339(8) . ? C13 C14 1.383(9) . ? C13 H13 0.9300 . ? C14 C15 1.382(10) . ? C14 H14 0.9300 . ? C15 C16 1.378(10) . ? C15 H15 0.9300 . ? C16 C17 1.379(9) . ? C16 H16 0.9300 . ? C17 N3 1.328(7) . ? C17 C18 1.509(8) . ? C18 O6 1.215(7) . ? C18 O5 1.297(7) . ? O1 Bi 2.662(4) 2 ? O3 Bi 2.636(4) 2 ? 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 O5 Bi N3 69.26(15) . . ? O5 Bi O1 136.50(14) . . ? N3 Bi O1 80.02(15) . . ? O5 Bi O3 135.06(14) . . ? N3 Bi O3 80.12(15) . . ? O1 Bi O3 63.70(13) . . ? O5 Bi N1 77.28(15) . . ? N3 Bi N1 71.31(17) . . ? O1 Bi N1 63.83(13) . . ? O3 Bi N1 123.34(14) . . ? O5 Bi N2 75.96(15) . . ? N3 Bi N2 70.29(17) . . ? O1 Bi N2 121.99(14) . . ? O3 Bi N2 62.88(13) . . ? N1 Bi N2 138.89(16) . . ? O5 Bi O3 69.12(13) . 2_545 ? N3 Bi O3 128.76(15) . 2_545 ? O1 Bi O3 112.66(13) . 2_545 ? O3 Bi O3 150.89(6) . 2_545 ? N1 Bi O3 71.53(14) . 2_545 ? N2 Bi O3 124.94(13) . 2_545 ? O5 Bi O1 69.87(14) . 2_545 ? N3 Bi O1 128.12(15) . 2_545 ? O1 Bi O1 150.78(7) . 2_545 ? O3 Bi O1 108.98(13) . 2_545 ? N1 Bi O1 127.28(13) . 2_545 ? N2 Bi O1 69.91(14) . 2_545 ? O3 Bi O1 58.83(13) 2_545 2_545 ? N1 C1 C2 122.6(6) . . ? N1 C1 H1 118.7 . . ? C2 C1 H1 118.7 . . ? C3 C2 C1 118.6(6) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C2 C3 C4 119.0(7) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C5 C4 C3 119.1(6) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? N1 C5 C4 122.3(6) . . ? N1 C5 C6 116.7(5) . . ? C4 C5 C6 121.0(6) . . ? O2 C6 O1 125.4(6) . . ? O2 C6 C5 119.0(6) . . ? O1 C6 C5 115.5(5) . . ? N2 C7 C8 121.9(6) . . ? N2 C7 H7 119.1 . . ? C8 C7 H7 119.1 . . ? C9 C8 C7 119.5(6) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C8 C9 C10 118.9(6) . . ? C8 C9 H9 120.6 . . ? C10 C9 H9 120.6 . . ? C11 C10 C9 119.2(6) . . ? C11 C10 H10 120.4 . . ? C9 C10 H10 120.4 . . ? N2 C11 C10 122.0(5) . . ? N2 C11 C12 116.7(5) . . ? C10 C11 C12 121.3(5) . . ? O4 C12 O3 125.6(6) . . ? O4 C12 C11 118.4(5) . . ? O3 C12 C11 115.9(5) . . ? N3 C13 C14 121.2(6) . . ? N3 C13 H13 119.4 . . ? C14 C13 H13 119.4 . . ? C15 C14 C13 118.6(6) . . ? C15 C14 H14 120.7 . . ? C13 C14 H14 120.7 . . ? C16 C15 C14 119.5(6) . . ? C16 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? C15 C16 C17 119.0(6) . . ? C15 C16 H16 120.5 . . ? C17 C16 H16 120.5 . . ? N3 C17 C16 121.4(6) . . ? N3 C17 C18 117.5(5) . . ? C16 C17 C18 121.0(5) . . ? O6 C18 O5 125.0(6) . . ? O6 C18 C17 118.8(6) . . ? O5 C18 C17 116.2(5) . . ? C1 N1 C5 118.2(5) . . ? C1 N1 Bi 124.1(4) . . ? C5 N1 Bi 117.6(4) . . ? C11 N2 C7 118.4(5) . . ? C11 N2 Bi 117.8(4) . . ? C7 N2 Bi 123.8(4) . . ? C17 N3 C13 120.3(5) . . ? C17 N3 Bi 115.5(4) . . ? C13 N3 Bi 124.0(4) . . ? C6 O1 Bi 125.7(4) . . ? C6 O1 Bi 127.9(4) . 2 ? Bi O1 Bi 105.58(14) . 2 ? C12 O3 Bi 126.0(4) . . ? C12 O3 Bi 128.1(4) . 2 ? Bi O3 Bi 105.26(14) . 2 ? C18 O5 Bi 121.3(4) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 1.377 _refine_diff_density_min -2.032 _refine_diff_density_rms 0.153 #===END data_compd2 _database_code_depnum_ccdc_archive 'CCDC 749254' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H18 Bi2 N4 O18' _chemical_formula_weight 1116.42 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 P21/c 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 12.341(3) _cell_length_b 11.886(2) _cell_length_c 21.485(4) _cell_angle_alpha 90.00 _cell_angle_beta 103.96(3) _cell_angle_gamma 90.00 _cell_volume 3058.6(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plates _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.424 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2096 _exptl_absorpt_coefficient_mu 11.587 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2754 _exptl_absorpt_correction_T_max 0.3904 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30287 _diffrn_reflns_av_R_equivalents 0.0521 _diffrn_reflns_av_sigmaI/netI 0.0393 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 26.33 _reflns_number_total 6118 _reflns_number_gt 5075 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0388P)^2^+7.0281P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6118 _refine_ls_number_parameters 483 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0456 _refine_ls_R_factor_gt 0.0329 _refine_ls_wR_factor_ref 0.0816 _refine_ls_wR_factor_gt 0.0767 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.100 _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 0.522961(19) 0.43431(2) 0.249030(12) 0.02639(8) Uani 1 1 d . . . Bi2 Bi 0.289315(19) 0.27823(2) 0.087916(12) 0.02521(8) Uani 1 1 d . . . O1 O 0.6239(4) 0.5023(5) 0.3514(2) 0.0459(14) Uani 1 1 d . . . O2 O 0.3322(4) 0.3545(4) 0.2129(2) 0.0305(11) Uani 1 1 d . . . O3 O 0.1657(4) 0.3294(5) 0.2338(2) 0.0373(12) Uani 1 1 d . . . O4 O 0.6188(4) 0.5927(4) 0.4415(2) 0.0356(12) Uani 1 1 d . . . O5 O 0.5401(4) 0.2573(4) 0.2845(2) 0.0366(12) Uani 1 1 d . . . O6 O 0.6889(4) 0.5891(4) 0.2402(3) 0.0404(13) Uani 1 1 d . . . O7 O 0.8728(4) 0.6122(5) 0.2596(3) 0.0547(16) Uani 1 1 d . . . H7 H 0.8555 0.6789 0.2553 0.082 Uiso 1 1 calc R . . O8 O 0.6275(5) 0.0937(5) 0.2870(3) 0.0485(14) Uani 1 1 d . . . O9 O 0.4923(4) 0.3346(5) 0.1425(2) 0.0364(12) Uani 1 1 d . . . O10 O 0.1918(4) 0.2639(4) -0.0157(2) 0.0325(11) Uani 1 1 d . . . O11 O 0.1810(4) 0.2934(5) -0.1194(2) 0.0450(14) Uani 1 1 d . . . O12 O 0.6583(5) 0.3815(7) 0.1275(3) 0.074(2) Uani 1 1 d . . . O13 O 0.1343(4) 0.1222(4) 0.0898(3) 0.0422(13) Uani 1 1 d . . . O14 O 0.2734(4) 0.4644(4) 0.0724(2) 0.0354(12) Uani 1 1 d . . . O15 O -0.0403(5) 0.0910(5) 0.0942(3) 0.0566(17) Uani 1 1 d . . . H15 H -0.0253 0.0262 0.0862 0.085 Uiso 1 1 calc R . . O16 O 0.1833(5) 0.6262(5) 0.0731(3) 0.0572(16) Uani 1 1 d . . . N1 N 0.4121(4) 0.4497(5) 0.3280(3) 0.0254(12) Uani 1 1 d . . . N2 N 0.7184(4) 0.3676(5) 0.2677(3) 0.0282(13) Uani 1 1 d . . . N3 N 0.4057(4) 0.3198(4) 0.0162(2) 0.0222(11) Uani 1 1 d . . . N4 N 0.1016(4) 0.3460(5) 0.0871(3) 0.0283(13) Uani 1 1 d . . . C1 C 0.5753(5) 0.5349(6) 0.3935(3) 0.0289(15) Uani 1 1 d . . . C2 C 0.4553(5) 0.5048(6) 0.3825(3) 0.0277(15) Uani 1 1 d . . . C3 C 0.3917(6) 0.5333(7) 0.4246(3) 0.0372(17) Uani 1 1 d . . . H3 H 0.4232 0.5716 0.4624 0.045 Uiso 1 1 calc R . . C4 C 0.2807(6) 0.5039(8) 0.4098(4) 0.048(2) Uani 1 1 d . . . H4 H 0.2359 0.5207 0.4377 0.057 Uiso 1 1 calc R . . C5 C 0.2365(6) 0.4483(7) 0.3517(4) 0.0413(19) Uani 1 1 d . . . H5 H 0.1613 0.4288 0.3404 0.050 Uiso 1 1 calc R . . C6 C 0.3043(5) 0.4227(6) 0.3118(3) 0.0282(15) Uani 1 1 d . . . C7 C 0.2628(6) 0.3638(6) 0.2475(3) 0.0298(15) Uani 1 1 d . . . C8 C 0.6258(6) 0.1956(6) 0.2826(3) 0.0321(16) Uani 1 1 d . . . C9 C 0.7281(6) 0.2567(6) 0.2760(3) 0.0293(16) Uani 1 1 d . . . C10 C 0.8292(7) 0.2010(7) 0.2809(4) 0.045(2) Uani 1 1 d . . . H10 H 0.8352 0.1236 0.2872 0.054 Uiso 1 1 calc R . . C11 C 0.9201(7) 0.2650(8) 0.2762(4) 0.051(2) Uani 1 1 d . . . H11 H 0.9889 0.2309 0.2788 0.062 Uiso 1 1 calc R . . C12 C 0.9086(6) 0.3801(7) 0.2676(4) 0.0391(18) Uani 1 1 d . . . H12 H 0.9696 0.4244 0.2652 0.047 Uiso 1 1 calc R . . C13 C 0.8061(6) 0.4278(6) 0.2628(3) 0.0309(16) Uani 1 1 d . . . C14 C 0.7827(6) 0.5510(7) 0.2526(4) 0.0364(17) Uani 1 1 d . . . C15 C 0.5610(6) 0.3533(7) 0.1078(3) 0.0361(18) Uani 1 1 d . . . C16 C 0.5139(5) 0.3430(6) 0.0358(3) 0.0273(15) Uani 1 1 d . . . C17 C 0.5784(6) 0.3595(7) -0.0074(3) 0.0364(17) Uani 1 1 d . . . H17 H 0.6543 0.3748 0.0066 0.044 Uiso 1 1 calc R . . C18 C 0.5277(6) 0.3529(7) -0.0718(3) 0.042(2) Uani 1 1 d . . . H18 H 0.5701 0.3649 -0.1016 0.051 Uiso 1 1 calc R . . C19 C 0.4166(6) 0.3289(6) -0.0930(3) 0.0348(17) Uani 1 1 d . . . H19 H 0.3824 0.3234 -0.1365 0.042 Uiso 1 1 calc R . . C20 C 0.3570(6) 0.3132(6) -0.0465(3) 0.0276(15) Uani 1 1 d . . . C21 C 0.2332(6) 0.2890(6) -0.0642(3) 0.0291(15) Uani 1 1 d . . . C22 C 0.0425(6) 0.1558(7) 0.0922(4) 0.0396(19) Uani 1 1 d . . . C23 C 0.0166(6) 0.2800(7) 0.0928(3) 0.0329(17) Uani 1 1 d . . . C24 C -0.0822(6) 0.3245(8) 0.0994(4) 0.047(2) Uani 1 1 d . . . H24 H -0.1401 0.2779 0.1043 0.057 Uiso 1 1 calc R . . C25 C -0.0946(7) 0.4412(8) 0.0986(4) 0.053(2) Uani 1 1 d . . . H25 H -0.1612 0.4730 0.1029 0.063 Uiso 1 1 calc R . . C26 C -0.0078(7) 0.5094(8) 0.0915(4) 0.047(2) Uani 1 1 d . . . H26 H -0.0149 0.5873 0.0902 0.056 Uiso 1 1 calc R . . C27 C 0.0898(6) 0.4578(6) 0.0862(3) 0.0323(16) Uani 1 1 d . . . C28 C 0.1881(7) 0.5234(7) 0.0768(3) 0.0377(18) Uani 1 1 d . . . O17 O -0.0083(6) 0.8867(6) 0.0729(4) 0.068(2) Uani 1 1 d . . . H17A H 0.035(11) 0.836(11) 0.070(7) 0.102 Uiso 1 1 d . . . H17B H 0.010(11) 0.909(10) 0.035(6) 0.102 Uiso 1 1 d . . . O18 O 0.1994(7) 0.8573(6) 0.0538(4) 0.083(2) Uani 1 1 d D . . H18A H 0.251(9) 0.802(8) 0.077(4) 0.125 Uiso 1 1 d D . . H18B H 0.169(10) 0.917(7) 0.074(4) 0.125 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi1 0.01571(13) 0.03450(16) 0.02911(14) -0.00135(11) 0.00568(10) -0.00234(10) Bi2 0.01455(12) 0.03216(16) 0.02929(14) -0.00059(11) 0.00604(10) -0.00260(10) O1 0.023(3) 0.080(4) 0.039(3) -0.016(3) 0.015(2) -0.012(3) O2 0.019(2) 0.040(3) 0.035(3) -0.008(2) 0.011(2) -0.008(2) O3 0.018(2) 0.049(3) 0.043(3) 0.000(2) 0.004(2) -0.007(2) O4 0.031(3) 0.040(3) 0.036(3) -0.007(2) 0.008(2) -0.013(2) O5 0.028(3) 0.038(3) 0.048(3) 0.009(2) 0.016(2) 0.000(2) O6 0.018(3) 0.042(3) 0.060(3) 0.010(3) 0.008(2) 0.006(2) O7 0.023(3) 0.050(4) 0.091(5) 0.018(4) 0.013(3) -0.004(3) O8 0.034(3) 0.034(3) 0.074(4) -0.006(3) 0.009(3) -0.010(2) O9 0.019(2) 0.064(4) 0.028(2) -0.004(2) 0.011(2) -0.007(2) O10 0.016(2) 0.048(3) 0.031(2) 0.000(2) 0.0003(19) -0.004(2) O11 0.027(3) 0.072(4) 0.031(3) -0.004(3) -0.003(2) 0.000(3) O12 0.026(3) 0.157(7) 0.036(3) 0.001(4) 0.001(2) -0.036(4) O13 0.023(3) 0.037(3) 0.069(4) 0.002(3) 0.017(3) -0.005(2) O14 0.026(3) 0.034(3) 0.051(3) -0.001(2) 0.018(2) -0.005(2) O15 0.025(3) 0.059(4) 0.087(5) 0.008(4) 0.014(3) -0.017(3) O16 0.063(4) 0.028(3) 0.085(5) 0.004(3) 0.028(4) -0.001(3) N1 0.020(3) 0.028(3) 0.029(3) 0.003(2) 0.008(2) -0.001(2) N2 0.013(3) 0.042(4) 0.029(3) 0.000(3) 0.004(2) 0.001(3) N3 0.015(3) 0.028(3) 0.024(3) -0.001(2) 0.006(2) -0.001(2) N4 0.014(3) 0.039(4) 0.033(3) 0.003(3) 0.006(2) -0.001(2) C1 0.021(3) 0.037(4) 0.028(3) 0.001(3) 0.005(3) 0.000(3) C2 0.023(3) 0.029(4) 0.031(3) 0.003(3) 0.007(3) 0.003(3) C3 0.031(4) 0.048(5) 0.033(4) -0.010(3) 0.009(3) 0.004(4) C4 0.026(4) 0.074(6) 0.047(5) -0.003(4) 0.017(4) 0.000(4) C5 0.019(3) 0.063(5) 0.044(4) 0.004(4) 0.013(3) 0.003(4) C6 0.018(3) 0.033(4) 0.033(4) 0.001(3) 0.005(3) -0.001(3) C7 0.022(3) 0.034(4) 0.032(4) 0.002(3) 0.005(3) 0.001(3) C8 0.031(4) 0.034(4) 0.030(4) 0.000(3) 0.005(3) -0.005(3) C9 0.022(3) 0.042(4) 0.026(3) -0.002(3) 0.009(3) 0.002(3) C10 0.034(4) 0.039(5) 0.066(6) -0.001(4) 0.020(4) 0.011(4) C11 0.025(4) 0.061(6) 0.072(6) 0.010(5) 0.018(4) 0.009(4) C12 0.023(4) 0.044(5) 0.052(5) 0.005(4) 0.012(3) -0.007(3) C13 0.019(3) 0.047(5) 0.027(3) 0.004(3) 0.005(3) -0.001(3) C14 0.024(4) 0.046(5) 0.041(4) 0.009(4) 0.010(3) -0.005(3) C15 0.019(4) 0.058(5) 0.030(4) 0.000(4) 0.006(3) -0.009(3) C16 0.014(3) 0.039(4) 0.028(3) 0.004(3) 0.004(3) -0.002(3) C17 0.022(4) 0.055(5) 0.035(4) -0.005(4) 0.012(3) -0.008(3) C18 0.035(4) 0.066(6) 0.031(4) -0.001(4) 0.017(3) -0.007(4) C19 0.037(4) 0.047(5) 0.021(3) -0.003(3) 0.008(3) -0.005(4) C20 0.023(3) 0.029(4) 0.029(3) 0.000(3) 0.003(3) 0.001(3) C21 0.025(4) 0.031(4) 0.031(4) -0.004(3) 0.007(3) 0.002(3) C22 0.025(4) 0.055(5) 0.040(4) -0.002(4) 0.010(3) -0.011(4) C23 0.019(3) 0.047(5) 0.032(4) 0.003(3) 0.006(3) -0.009(3) C24 0.011(3) 0.079(7) 0.052(5) 0.005(4) 0.009(3) -0.002(4) C25 0.027(4) 0.067(6) 0.068(6) 0.005(5) 0.018(4) 0.014(4) C26 0.031(4) 0.057(5) 0.051(5) 0.003(4) 0.010(4) 0.015(4) C27 0.024(4) 0.041(5) 0.032(4) 0.005(3) 0.008(3) 0.006(3) C28 0.036(4) 0.041(5) 0.034(4) -0.001(3) 0.006(3) -0.005(4) O17 0.053(5) 0.053(4) 0.096(5) -0.009(4) 0.012(4) -0.021(3) O18 0.076(6) 0.054(5) 0.115(6) -0.005(4) 0.014(5) 0.001(4) _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 O5 2.230(5) . ? Bi1 O1 2.391(5) . ? Bi1 N1 2.429(5) . ? Bi1 N2 2.478(5) . ? Bi1 O2 2.483(4) . ? Bi1 O9 2.524(5) . ? Bi1 O8 2.635(5) 2_655 ? Bi2 O14 2.239(5) . ? Bi2 O10 2.268(5) . ? Bi2 N3 2.398(5) . ? Bi2 N4 2.449(5) . ? Bi2 O9 2.584(5) . ? Bi2 O4 2.625(5) 2_645 ? Bi2 O13 2.672(5) . ? O1 C1 1.263(8) . ? O2 C7 1.267(8) . ? O3 C7 1.232(8) . ? O4 C1 1.246(8) . ? O4 Bi2 2.625(5) 2_655 ? O5 C8 1.296(9) . ? O6 C14 1.212(9) . ? O7 C14 1.307(9) . ? O7 H7 0.8200 . ? O8 C8 1.214(9) . ? O8 Bi1 2.635(5) 2_645 ? O9 C15 1.278(8) . ? O10 C21 1.300(8) . ? O11 C21 1.207(8) . ? O12 C15 1.220(8) . ? O13 C22 1.214(9) . ? O14 C28 1.287(9) . ? O15 C22 1.288(9) . ? O15 H15 0.8200 . ? O16 C28 1.225(9) . ? N1 C6 1.331(8) . ? N1 C2 1.335(8) . ? N2 C13 1.323(9) . ? N2 C9 1.331(9) . ? N3 C16 1.328(8) . ? N3 C20 1.339(8) . ? N4 C27 1.336(9) . ? N4 C23 1.340(8) . ? C1 C2 1.486(9) . ? C2 C3 1.376(9) . ? C3 C4 1.375(10) . ? C3 H3 0.9300 . ? C4 C5 1.401(11) . ? C4 H4 0.9300 . ? C5 C6 1.369(9) . ? C5 H5 0.9300 . ? C6 C7 1.523(10) . ? C8 C9 1.493(10) . ? C9 C10 1.395(10) . ? C10 C11 1.380(11) . ? C10 H10 0.9300 . ? C11 C12 1.384(12) . ? C11 H11 0.9300 . ? C12 C13 1.367(10) . ? C12 H12 0.9300 . ? C13 C14 1.499(11) . ? C15 C16 1.519(9) . ? C16 C17 1.376(9) . ? C17 C18 1.377(10) . ? C17 H17 0.9300 . ? C18 C19 1.367(10) . ? C18 H18 0.9300 . ? C19 C20 1.388(9) . ? C19 H19 0.9300 . ? C20 C21 1.510(9) . ? C22 C23 1.512(11) . ? C23 C24 1.367(10) . ? C24 C25 1.395(12) . ? C24 H24 0.9300 . ? C25 C26 1.381(12) . ? C25 H25 0.9300 . ? C26 C27 1.380(10) . ? C26 H26 0.9300 . ? C27 C28 1.498(10) . ? O17 H17A 0.82(13) . ? O17 H17B 0.93(11) . ? O18 H18A 0.97(2) . ? O18 H18B 0.95(2) . ? 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 O5 Bi1 O1 91.1(2) . . ? O5 Bi1 N1 81.68(18) . . ? O1 Bi1 N1 65.72(17) . . ? O5 Bi1 N2 68.56(18) . . ? O1 Bi1 N2 71.86(18) . . ? N1 Bi1 N2 126.96(18) . . ? O5 Bi1 O2 75.57(18) . . ? O1 Bi1 O2 131.36(15) . . ? N1 Bi1 O2 66.13(16) . . ? N2 Bi1 O2 137.82(18) . . ? O5 Bi1 O9 81.23(18) . . ? O1 Bi1 O9 157.46(16) . . ? N1 Bi1 O9 132.99(16) . . ? N2 Bi1 O9 85.62(17) . . ? O2 Bi1 O9 67.28(14) . . ? O5 Bi1 O8 141.30(18) . 2_655 ? O1 Bi1 O8 101.6(2) . 2_655 ? N1 Bi1 O8 71.04(18) . 2_655 ? N2 Bi1 O8 150.13(19) . 2_655 ? O2 Bi1 O8 68.58(17) . 2_655 ? O9 Bi1 O8 97.52(18) . 2_655 ? O14 Bi2 O10 85.50(18) . . ? O14 Bi2 N3 75.26(17) . . ? O10 Bi2 N3 69.06(17) . . ? O14 Bi2 N4 67.96(18) . . ? O10 Bi2 N4 74.97(18) . . ? N3 Bi2 N4 129.78(18) . . ? O14 Bi2 O9 81.49(18) . . ? O10 Bi2 O9 133.75(15) . . ? N3 Bi2 O9 64.72(16) . . ? N4 Bi2 O9 136.85(18) . . ? O14 Bi2 O4 145.27(16) . 2_645 ? O10 Bi2 O4 81.87(16) . 2_645 ? N3 Bi2 O4 70.01(16) . 2_645 ? N4 Bi2 O4 137.51(18) . 2_645 ? O9 Bi2 O4 84.21(16) . 2_645 ? O14 Bi2 O13 130.61(17) . . ? O10 Bi2 O13 75.56(17) . . ? N3 Bi2 O13 134.02(17) . . ? N4 Bi2 O13 63.20(18) . . ? O9 Bi2 O13 142.37(17) . . ? O4 Bi2 O13 76.87(16) 2_645 . ? C1 O1 Bi1 122.1(4) . . ? C7 O2 Bi1 120.5(4) . . ? C1 O4 Bi2 112.9(4) . 2_655 ? C8 O5 Bi1 122.3(4) . . ? C14 O7 H7 109.5 . . ? C8 O8 Bi1 134.1(5) . 2_645 ? C15 O9 Bi1 118.2(4) . . ? C15 O9 Bi2 119.2(4) . . ? Bi1 O9 Bi2 116.76(17) . . ? C21 O10 Bi2 123.5(4) . . ? C22 O13 Bi2 116.8(5) . . ? C28 O14 Bi2 124.9(5) . . ? C22 O15 H15 109.5 . . ? C6 N1 C2 120.6(6) . . ? C6 N1 Bi1 119.7(4) . . ? C2 N1 Bi1 118.5(4) . . ? C13 N2 C9 119.8(6) . . ? C13 N2 Bi1 126.7(5) . . ? C9 N2 Bi1 113.0(4) . . ? C16 N3 C20 120.3(5) . . ? C16 N3 Bi2 123.4(4) . . ? C20 N3 Bi2 116.2(4) . . ? C27 N4 C23 119.9(6) . . ? C27 N4 Bi2 115.3(4) . . ? C23 N4 Bi2 124.5(5) . . ? O4 C1 O1 125.3(6) . . ? O4 C1 C2 118.7(6) . . ? O1 C1 C2 116.0(6) . . ? N1 C2 C3 121.9(6) . . ? N1 C2 C1 115.4(6) . . ? C3 C2 C1 122.7(6) . . ? C4 C3 C2 118.7(7) . . ? C4 C3 H3 120.7 . . ? C2 C3 H3 120.7 . . ? C3 C4 C5 118.6(7) . . ? C3 C4 H4 120.7 . . ? C5 C4 H4 120.7 . . ? C6 C5 C4 119.8(7) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? N1 C6 C5 120.4(7) . . ? N1 C6 C7 116.3(6) . . ? C5 C6 C7 123.2(6) . . ? O3 C7 O2 126.0(7) . . ? O3 C7 C6 117.6(6) . . ? O2 C7 C6 116.4(6) . . ? O8 C8 O5 124.2(7) . . ? O8 C8 C9 119.5(7) . . ? O5 C8 C9 116.3(6) . . ? N2 C9 C10 122.0(7) . . ? N2 C9 C8 116.3(6) . . ? C10 C9 C8 121.6(7) . . ? C11 C10 C9 117.5(8) . . ? C11 C10 H10 121.3 . . ? C9 C10 H10 121.3 . . ? C10 C11 C12 119.7(7) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? C13 C12 C11 118.9(7) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? N2 C13 C12 122.0(7) . . ? N2 C13 C14 114.1(6) . . ? C12 C13 C14 123.9(7) . . ? O6 C14 O7 124.0(8) . . ? O6 C14 C13 122.5(7) . . ? O7 C14 C13 113.5(6) . . ? O12 C15 O9 125.6(7) . . ? O12 C15 C16 118.6(6) . . ? O9 C15 C16 115.8(6) . . ? N3 C16 C17 121.1(6) . . ? N3 C16 C15 116.7(5) . . ? C17 C16 C15 122.2(6) . . ? C16 C17 C18 118.3(7) . . ? C16 C17 H17 120.9 . . ? C18 C17 H17 120.9 . . ? C19 C18 C17 121.5(6) . . ? C19 C18 H18 119.3 . . ? C17 C18 H18 119.3 . . ? C18 C19 C20 116.9(6) . . ? C18 C19 H19 121.6 . . ? C20 C19 H19 121.6 . . ? N3 C20 C19 121.9(6) . . ? N3 C20 C21 116.5(6) . . ? C19 C20 C21 121.6(6) . . ? O11 C21 O10 125.3(7) . . ? O11 C21 C20 120.5(6) . . ? O10 C21 C20 114.2(6) . . ? O13 C22 O15 124.1(8) . . ? O13 C22 C23 121.5(7) . . ? O15 C22 C23 114.4(7) . . ? N4 C23 C24 121.4(8) . . ? N4 C23 C22 113.6(6) . . ? C24 C23 C22 125.1(7) . . ? C23 C24 C25 118.8(7) . . ? C23 C24 H24 120.6 . . ? C25 C24 H24 120.6 . . ? C26 C25 C24 119.9(7) . . ? C26 C25 H25 120.0 . . ? C24 C25 H25 120.0 . . ? C27 C26 C25 117.6(8) . . ? C27 C26 H26 121.2 . . ? C25 C26 H26 121.2 . . ? N4 C27 C26 122.4(7) . . ? N4 C27 C28 115.5(6) . . ? C26 C27 C28 122.1(8) . . ? O16 C28 O14 124.6(7) . . ? O16 C28 C27 120.0(7) . . ? O14 C28 C27 115.5(7) . . ? H17A O17 H17B 80(10) . . ? H18A O18 H18B 124(4) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O15 H15 O17 0.82 1.70 2.520(10) 172.8 1_545 O7 H7 O3 0.82 1.83 2.634(8) 166.2 2_655 O18 H18A O16 0.97(2) 2.24(12) 2.793(9) 115(10) . O18 H18B O17 0.95(2) 2.21(13) 2.715(11) 112(10) . O17 H17A O18 0.82(13) 2.15(14) 2.715(11) 126(12) . _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 26.33 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 1.965 _refine_diff_density_min -2.393 _refine_diff_density_rms 0.179 #===END data_compd3 _database_code_depnum_ccdc_archive 'CCDC 749255' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H23 Bi N4 O11' _chemical_formula_weight 824.50 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 Cc 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' _cell_length_a 9.6810(6) _cell_length_b 18.5747(12) _cell_length_c 16.5929(11) _cell_angle_alpha 90.00 _cell_angle_beta 100.5850(10) _cell_angle_gamma 90.00 _cell_volume 2933.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needles _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.867 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1608 _exptl_absorpt_coefficient_mu 6.082 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4623 _exptl_absorpt_correction_T_max 0.5814 _exptl_absorpt_process_details 'SADABS, Sheldrick 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 14019 _diffrn_reflns_av_R_equivalents 0.0300 _diffrn_reflns_av_sigmaI/netI 0.0368 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 25.05 _reflns_number_total 5182 _reflns_number_gt 4992 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0264P)^2^+8.0711P] 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 mixed _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 0.00(1) _refine_ls_number_reflns 5182 _refine_ls_number_parameters 427 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0253 _refine_ls_R_factor_gt 0.0240 _refine_ls_wR_factor_ref 0.0599 _refine_ls_wR_factor_gt 0.0593 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.094 _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 Bi Bi 0.29793(4) 0.730010(9) 0.54441(3) 0.01402(6) Uani 1 1 d . . . O3 O 0.1597(7) 0.6399(4) 0.4857(4) 0.0251(17) Uani 1 1 d . . . O4 O -0.0316(7) 0.5752(4) 0.4842(4) 0.0292(17) Uani 1 1 d . . . O2 O 0.6410(8) 0.5815(4) 0.5844(4) 0.0327(18) Uani 1 1 d . . . O1 O 0.4632(7) 0.6545(4) 0.5991(4) 0.0176(14) Uani 1 1 d . . . O7 O 0.1612(8) 0.8467(4) 0.4690(4) 0.0351(17) Uani 1 1 d . . . C30 C 0.0640(12) 0.6123(6) 0.5212(7) 0.025(3) Uani 1 1 d . . . O5 O 0.5142(7) 0.8135(3) 0.5369(4) 0.0283(16) Uani 1 1 d . . . O6 O 0.4083(9) 0.8362(4) 0.6426(4) 0.043(2) Uani 1 1 d . . . O8 O 0.0433(7) 0.7856(4) 0.5440(4) 0.0359(17) Uani 1 1 d . . . N2 N 0.1826(8) 0.6654(4) 0.6493(5) 0.0131(16) Uani 1 1 d . . . N4 N 0.0679(9) 0.8429(5) 0.5162(5) 0.030(2) Uani 1 1 d . . . C29 C 0.1987(10) 0.6777(4) 0.7317(6) 0.0159(19) Uani 1 1 d . . . C21 C 0.0730(10) 0.6250(5) 0.6098(6) 0.019(2) Uani 1 1 d . . . C2 C 0.6142(10) 0.6147(4) 0.4163(6) 0.025(2) Uani 1 1 d . . . H2 H 0.6927 0.5879 0.4395 0.030 Uiso 1 1 calc R . . C24 C 0.1049(9) 0.6449(4) 0.7776(5) 0.0169(17) Uani 1 1 d . . . C3 C 0.5833(10) 0.6302(4) 0.3327(5) 0.026(2) Uani 1 1 d . . . H3 H 0.6386 0.6113 0.2975 0.031 Uiso 1 1 calc R . . C1 C 0.5177(10) 0.6424(5) 0.4638(5) 0.018(2) Uani 1 1 d . . . C27 C 0.3241(9) 0.7337(4) 0.8532(5) 0.0197(17) Uani 1 1 d . . . H27 H 0.3959 0.7635 0.8792 0.024 Uiso 1 1 calc R . . C6 C 0.3218(10) 0.7369(4) 0.1898(5) 0.0284(19) Uani 1 1 d . . . H6 H 0.2989 0.7481 0.1343 0.034 Uiso 1 1 calc R . . C16 C 0.9512(8) 1.0477(4) 0.8314(4) 0.0229(15) Uani 1 1 d . . . H16 H 1.0243 1.0758 0.8592 0.027 Uiso 1 1 calc R . . N3 N 0.6288(5) 0.9170(3) 0.7131(3) 0.0156(11) Uani 1 1 d . . . H3N H 0.5695 0.8991 0.7403 0.019 Uiso 1 1 calc R . . C11 C 0.6140(6) 0.9013(3) 0.6343(4) 0.0172(13) Uani 1 1 d . . . C13 C 0.8061(7) 0.9785(3) 0.6224(4) 0.0194(13) Uani 1 1 d . . . H13 H 0.8645 1.0003 0.5909 0.023 Uiso 1 1 calc R . . C15 C 0.9353(8) 1.0389(3) 0.7482(4) 0.0207(14) Uani 1 1 d . . . H15 H 0.9959 1.0619 0.7190 0.025 Uiso 1 1 calc R . . C12 C 0.7031(7) 0.9316(3) 0.5863(4) 0.0210(14) Uani 1 1 d . . . H12 H 0.6929 0.9203 0.5309 0.025 Uiso 1 1 calc R . . C19 C 0.7327(8) 0.9600(3) 0.7536(4) 0.0152(13) Uani 1 1 d . . . C4 C 0.4676(8) 0.6748(4) 0.3015(5) 0.0190(17) Uani 1 1 d . . . C22 C -0.0164(8) 0.5895(4) 0.6554(5) 0.0181(18) Uani 1 1 d . . . H22 H -0.0859 0.5584 0.6293 0.022 Uiso 1 1 calc R . . C9 C 0.3854(11) 0.7033(4) 0.3564(6) 0.018(2) Uani 1 1 d . . . N1 N 0.4150(8) 0.6865(3) 0.4380(5) 0.0123(16) Uani 1 1 d . . . C10 C 0.5445(11) 0.6239(6) 0.5564(7) 0.021(2) Uani 1 1 d . . . C20 C 0.5070(10) 0.8465(5) 0.6010(5) 0.020(2) Uani 1 1 d . . . C23 C -0.0004(8) 0.6008(4) 0.7365(5) 0.0187(17) Uani 1 1 d . . . H23 H -0.0616 0.5786 0.7658 0.022 Uiso 1 1 calc R . . C28 C 0.3069(13) 0.7227(4) 0.7709(8) 0.021(2) Uani 1 1 d . . . H28 H 0.3667 0.7450 0.7407 0.025 Uiso 1 1 calc R . . C25 C 0.1268(8) 0.6587(4) 0.8625(4) 0.0215(17) Uani 1 1 d . . . H25 H 0.0661 0.6388 0.8939 0.026 Uiso 1 1 calc R . . C5 C 0.4329(11) 0.6941(5) 0.2160(6) 0.033(2) Uani 1 1 d . . . H5 H 0.4870 0.6770 0.1792 0.040 Uiso 1 1 calc R . . C14 C 0.8231(8) 0.9933(3) 0.7061(4) 0.0175(13) Uani 1 1 d . . . C8 C 0.2709(13) 0.7477(5) 0.3254(7) 0.021(2) Uani 1 1 d . . . H8 H 0.2151 0.7655 0.3608 0.025 Uiso 1 1 calc R . . C17 C 0.8599(8) 1.0153(4) 0.8736(5) 0.0196(14) Uani 1 1 d . . . H17 H 0.8722 1.0234 0.9298 0.024 Uiso 1 1 calc R . . C18 C 0.7498(8) 0.9708(4) 0.8383(4) 0.0185(13) Uani 1 1 d . . . H18 H 0.6904 0.9494 0.8694 0.022 Uiso 1 1 calc R . . C26 C 0.2338(10) 0.7002(4) 0.8988(5) 0.0216(17) Uani 1 1 d . . . H26 H 0.2483 0.7069 0.9553 0.026 Uiso 1 1 calc R . . C7 C 0.2392(9) 0.7653(5) 0.2435(5) 0.0282(19) Uani 1 1 d . . . H7 H 0.1641 0.7956 0.2239 0.034 Uiso 1 1 calc R . . O9 O 0.0019(7) 0.8993(3) 0.5262(3) 0.0585(19) Uani 1 1 d . . . O10 O 0.4376(5) 0.9028(3) 0.8121(3) 0.0298(11) Uani 1 1 d D . . H10A H 0.441(7) 0.914(4) 0.8686(15) 0.045 Uiso 1 1 d D . . H10B H 0.365(6) 0.922(4) 0.772(3) 0.045 Uiso 1 1 d D . . O11 O 0.2385(4) 0.9555(2) 0.6862(2) 0.0125(8) Uani 1 1 d D . . H11A H 0.200(6) 0.987(3) 0.712(3) 0.019 Uiso 1 1 d D . . H11B H 0.239(6) 0.930(3) 0.643(3) 0.019 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi 0.01480(9) 0.01627(10) 0.01110(9) -0.00001(17) 0.00270(6) -0.00093(18) O3 0.029(3) 0.026(3) 0.022(3) -0.005(2) 0.008(3) -0.008(3) O4 0.024(3) 0.034(4) 0.029(3) 0.000(3) 0.004(3) -0.015(3) O2 0.021(3) 0.037(4) 0.040(4) 0.012(3) 0.004(3) 0.008(3) O1 0.019(3) 0.023(3) 0.010(3) 0.002(2) 0.000(2) 0.007(2) O7 0.036(4) 0.031(4) 0.036(4) 0.013(3) 0.000(3) 0.006(3) C30 0.029(5) 0.029(5) 0.013(4) 0.002(4) -0.004(4) 0.001(4) O5 0.032(4) 0.036(4) 0.021(3) -0.014(3) 0.016(3) -0.012(3) O6 0.057(4) 0.053(4) 0.020(3) -0.014(3) 0.014(3) -0.029(3) O8 0.032(4) 0.045(4) 0.033(3) 0.016(3) 0.011(3) 0.012(3) N2 0.014(3) 0.009(3) 0.016(3) 0.005(3) 0.004(3) -0.001(3) N4 0.032(4) 0.037(5) 0.018(5) 0.004(4) -0.003(4) 0.007(4) C29 0.014(4) 0.017(4) 0.017(4) 0.009(3) 0.002(3) 0.008(3) C21 0.013(4) 0.025(5) 0.017(4) -0.003(3) -0.004(3) -0.007(3) C2 0.022(4) 0.009(4) 0.047(6) -0.004(4) 0.012(4) -0.006(3) C24 0.020(4) 0.016(4) 0.017(4) 0.003(3) 0.011(3) 0.001(3) C3 0.036(5) 0.018(4) 0.031(5) -0.010(4) 0.025(4) -0.012(4) C1 0.024(5) 0.022(5) 0.008(4) -0.005(3) 0.000(3) -0.001(3) C27 0.025(4) 0.021(4) 0.013(4) -0.005(3) 0.002(3) 0.005(3) C6 0.040(5) 0.030(5) 0.012(4) 0.004(3) -0.004(4) -0.020(4) C16 0.021(4) 0.017(3) 0.028(4) -0.001(3) -0.004(3) 0.001(3) N3 0.020(3) 0.015(3) 0.013(3) 0.001(2) 0.005(2) -0.001(2) C11 0.017(3) 0.019(3) 0.016(3) -0.002(2) 0.006(2) -0.001(2) C13 0.021(3) 0.017(3) 0.021(3) 0.001(3) 0.005(3) -0.003(3) C15 0.023(4) 0.013(3) 0.024(4) -0.001(3) -0.003(3) -0.004(3) C12 0.028(4) 0.022(3) 0.014(3) -0.002(3) 0.005(3) 0.000(3) C19 0.020(4) 0.008(3) 0.017(3) 0.005(3) 0.002(3) 0.007(3) C4 0.016(4) 0.018(4) 0.022(4) -0.006(3) 0.002(3) -0.007(3) C22 0.013(3) 0.017(4) 0.025(4) 0.013(3) 0.006(3) 0.008(3) C9 0.022(5) 0.017(4) 0.017(4) -0.013(4) 0.010(3) -0.013(4) N1 0.012(3) 0.013(4) 0.011(3) -0.006(2) 0.000(2) -0.008(3) C10 0.012(4) 0.016(4) 0.034(6) 0.000(4) 0.002(4) 0.000(3) C20 0.026(5) 0.018(4) 0.014(5) -0.011(3) -0.006(4) -0.007(4) C23 0.020(4) 0.019(4) 0.021(4) 0.012(3) 0.015(3) 0.014(3) C28 0.023(5) 0.018(4) 0.023(5) 0.004(4) 0.009(4) 0.004(4) C25 0.031(4) 0.020(4) 0.016(3) 0.009(3) 0.010(3) 0.014(3) C5 0.035(6) 0.038(6) 0.030(5) -0.014(5) 0.016(4) -0.022(5) C14 0.031(4) 0.008(3) 0.013(3) 0.001(3) 0.004(3) -0.005(3) C8 0.025(5) 0.028(4) 0.009(4) -0.002(4) 0.003(3) -0.005(4) C17 0.023(4) 0.019(4) 0.017(4) 0.004(3) 0.003(3) -0.002(3) C18 0.020(4) 0.017(3) 0.016(3) 0.007(3) -0.003(3) 0.002(3) C26 0.035(5) 0.017(4) 0.015(4) 0.005(3) 0.011(4) 0.010(4) C7 0.029(5) 0.036(6) 0.020(4) 0.002(4) 0.004(3) -0.004(4) O9 0.084(5) 0.058(4) 0.034(3) 0.004(3) 0.012(3) 0.056(4) O10 0.022(3) 0.052(3) 0.015(2) 0.002(2) 0.0012(19) 0.004(2) O11 0.014(2) 0.018(2) 0.0080(19) 0.0079(16) 0.0066(16) 0.0026(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 Bi O1 2.195(6) . ? Bi O3 2.250(7) . ? Bi N1 2.407(8) . ? Bi N2 2.535(8) . ? Bi O5 2.627(6) . ? Bi O6 2.654(7) . ? Bi O8 2.671(7) . ? Bi O7 2.721(7) . ? O3 C30 1.291(13) . ? O4 C30 1.225(14) . ? O2 C10 1.245(13) . ? O1 C10 1.283(13) . ? O7 N4 1.303(10) . ? C30 C21 1.476(14) . ? O5 C20 1.241(10) . ? O6 C20 1.292(12) . ? O8 N4 1.201(11) . ? N2 C21 1.365(12) . ? N2 C29 1.366(12) . ? N4 O9 1.253(10) . ? C29 C28 1.404(15) . ? C29 C24 1.425(12) . ? C21 C22 1.412(12) . ? C2 C3 1.394(13) . ? C2 C1 1.425(13) . ? C2 H2 0.9300 . ? C24 C23 1.386(11) . ? C24 C25 1.409(11) . ? C3 C4 1.413(11) . ? C3 H3 0.9300 . ? C1 N1 1.299(12) . ? C1 C10 1.549(14) . ? C27 C28 1.360(15) . ? C27 C26 1.403(12) . ? C27 H27 0.9300 . ? C6 C5 1.343(14) . ? C6 C7 1.405(13) . ? C6 H6 0.9300 . ? C16 C17 1.364(10) . ? C16 C15 1.372(9) . ? C16 H16 0.9300 . ? N3 C11 1.321(8) . ? N3 C19 1.360(9) . ? N3 H3N 0.8600 . ? C11 C12 1.396(8) . ? C11 C20 1.485(11) . ? C13 C12 1.375(9) . ? C13 C14 1.396(9) . ? C13 H13 0.9300 . ? C15 C14 1.451(9) . ? C15 H15 0.9300 . ? C12 H12 0.9300 . ? C19 C18 1.400(9) . ? C19 C14 1.423(9) . ? C4 C9 1.417(12) . ? C4 C5 1.443(12) . ? C22 C23 1.343(12) . ? C22 H22 0.9300 . ? C9 N1 1.368(13) . ? C9 C8 1.401(15) . ? C23 H23 0.9300 . ? C28 H28 0.9300 . ? C25 C26 1.341(12) . ? C25 H25 0.9300 . ? C5 H5 0.9300 . ? C8 C7 1.376(13) . ? C8 H8 0.9300 . ? C17 C18 1.390(10) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C26 H26 0.9300 . ? C7 H7 0.9300 . ? O10 H10A 0.95(2) . ? O10 H10B 0.95(2) . ? O11 H11A 0.857(18) . ? O11 H11B 0.857(18) . ? 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 O1 Bi O3 91.93(19) . . ? O1 Bi N1 71.5(3) . . ? O3 Bi N1 75.8(2) . . ? O1 Bi N2 78.1(2) . . ? O3 Bi N2 69.1(2) . . ? N1 Bi N2 132.12(19) . . ? O1 Bi O5 82.5(2) . . ? O3 Bi O5 146.5(2) . . ? N1 Bi O5 71.1(2) . . ? N2 Bi O5 140.1(2) . . ? O1 Bi O6 92.3(3) . . ? O3 Bi O6 163.5(2) . . ? N1 Bi O6 120.6(2) . . ? N2 Bi O6 96.2(2) . . ? O5 Bi O6 49.92(19) . . ? O1 Bi O8 148.3(2) . . ? O3 Bi O8 79.1(2) . . ? N1 Bi O8 133.4(2) . . ? N2 Bi O8 70.3(2) . . ? O5 Bi O8 121.0(2) . . ? O6 Bi O8 89.0(2) . . ? O1 Bi O7 162.8(2) . . ? O3 Bi O7 101.1(3) . . ? N1 Bi O7 100.7(2) . . ? N2 Bi O7 117.0(2) . . ? O5 Bi O7 80.4(2) . . ? O6 Bi O7 78.32(19) . . ? O8 Bi O7 47.2(2) . . ? C30 O3 Bi 121.1(7) . . ? C10 O1 Bi 122.0(7) . . ? N4 O7 Bi 90.8(6) . . ? O4 C30 O3 122.3(10) . . ? O4 C30 C21 119.3(10) . . ? O3 C30 C21 118.4(10) . . ? C20 O5 Bi 94.6(6) . . ? C20 O6 Bi 92.1(5) . . ? N4 O8 Bi 95.5(6) . . ? C21 N2 C29 120.5(8) . . ? C21 N2 Bi 109.4(6) . . ? C29 N2 Bi 128.7(6) . . ? O8 N4 O9 123.3(9) . . ? O8 N4 O7 119.1(9) . . ? O9 N4 O7 117.5(9) . . ? N2 C29 C28 120.1(9) . . ? N2 C29 C24 119.9(8) . . ? C28 C29 C24 120.1(9) . . ? N2 C21 C22 119.9(9) . . ? N2 C21 C30 117.7(9) . . ? C22 C21 C30 121.9(9) . . ? C3 C2 C1 115.7(8) . . ? C3 C2 H2 122.2 . . ? C1 C2 H2 122.2 . . ? C23 C24 C25 124.2(7) . . ? C23 C24 C29 118.2(8) . . ? C25 C24 C29 117.6(8) . . ? C2 C3 C4 119.7(8) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? N1 C1 C2 125.8(9) . . ? N1 C1 C10 116.5(9) . . ? C2 C1 C10 117.5(9) . . ? C28 C27 C26 120.1(8) . . ? C28 C27 H27 120.0 . . ? C26 C27 H27 120.0 . . ? C5 C6 C7 122.1(8) . . ? C5 C6 H6 118.9 . . ? C7 C6 H6 118.9 . . ? C17 C16 C15 120.0(7) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C11 N3 C19 123.7(6) . . ? C11 N3 H3N 118.2 . . ? C19 N3 H3N 118.2 . . ? N3 C11 C12 120.6(6) . . ? N3 C11 C20 117.5(6) . . ? C12 C11 C20 121.7(6) . . ? C12 C13 C14 120.1(6) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C16 C15 C14 119.4(7) . . ? C16 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? C13 C12 C11 118.8(6) . . ? C13 C12 H12 120.6 . . ? C11 C12 H12 120.6 . . ? N3 C19 C18 121.4(7) . . ? N3 C19 C14 117.1(6) . . ? C18 C19 C14 121.4(6) . . ? C3 C4 C9 119.1(8) . . ? C3 C4 C5 122.1(8) . . ? C9 C4 C5 118.8(8) . . ? C23 C22 C21 119.6(8) . . ? C23 C22 H22 120.2 . . ? C21 C22 H22 120.2 . . ? N1 C9 C8 120.4(9) . . ? N1 C9 C4 120.6(9) . . ? C8 C9 C4 118.9(9) . . ? C1 N1 C9 118.7(8) . . ? C1 N1 Bi 113.9(7) . . ? C9 N1 Bi 127.4(6) . . ? O2 C10 O1 124.7(11) . . ? O2 C10 C1 119.2(10) . . ? O1 C10 C1 116.2(9) . . ? O5 C20 O6 123.2(9) . . ? O5 C20 C11 120.9(9) . . ? O6 C20 C11 115.9(8) . . ? C22 C23 C24 121.7(7) . . ? C22 C23 H23 119.1 . . ? C24 C23 H23 119.1 . . ? C27 C28 C29 119.9(9) . . ? C27 C28 H28 120.1 . . ? C29 C28 H28 120.1 . . ? C26 C25 C24 121.0(7) . . ? C26 C25 H25 119.5 . . ? C24 C25 H25 119.5 . . ? C6 C5 C4 119.5(8) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C13 C14 C19 119.5(6) . . ? C13 C14 C15 122.4(6) . . ? C19 C14 C15 118.0(6) . . ? C7 C8 C9 121.3(9) . . ? C7 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? C16 C17 C18 124.4(7) . . ? C16 C17 H17 117.8 . . ? C18 C17 H17 117.8 . . ? C17 C18 C19 116.7(6) . . ? C17 C18 H18 121.6 . . ? C19 C18 H18 121.6 . . ? C25 C26 C27 121.3(7) . . ? C25 C26 H26 119.4 . . ? C27 C26 H26 119.4 . . ? C8 C7 C6 119.2(9) . . ? C8 C7 H7 120.4 . . ? C6 C7 H7 120.4 . . ? H10A O10 H10B 120(3) . . ? H11A O11 H11B 151(5) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O10 H10A O4 0.95(2) 1.90(2) 2.845(8) 171(6) 4_565 O11 H11A O2 0.857(18) 2.73(6) 2.938(8) 96(4) 3_455 N3 H3N O10 0.86 1.90 2.704(7) 154.8 . O10 H10B O11 0.95(2) 1.81(2) 2.750(6) 173(6) . O11 H11B O6 0.857(18) 2.39(5) 2.929(9) 121(5) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.204 _refine_diff_density_min -0.420 _refine_diff_density_rms 0.106 #===END