# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_1 _database_code_depnum_ccdc_archive 'CCDC 871627' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H3 Bi3 Cu N4 O11' _chemical_formula_weight 1045.64 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' Cu Cu 0.3201 1.2651 '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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.0862(5) _cell_length_b 9.8582(7) _cell_length_c 12.1267(8) _cell_angle_alpha 71.132(4) _cell_angle_beta 83.785(4) _cell_angle_gamma 86.867(4) _cell_volume 796.73(10) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5207 _cell_measurement_theta_min 2.89 _cell_measurement_theta_max 32.21 _exptl_crystal_description stick _exptl_crystal_colour blue _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 4.359 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 914 _exptl_absorpt_coefficient_mu 34.424 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.0675 _exptl_absorpt_correction_T_max 0.4249 _exptl_absorpt_process_details Sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 21057 _diffrn_reflns_av_R_equivalents 0.0635 _diffrn_reflns_av_sigmaI/netI 0.0653 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 30.03 _reflns_number_total 4619 _reflns_number_gt 3585 _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^)+(0.0438P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4619 _refine_ls_number_parameters 266 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0604 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_ref 0.0955 _refine_ls_wR_factor_gt 0.0887 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 Cu1 Cu 0.41371(16) 0.65390(12) 0.24169(11) 0.0208(3) Uani 1 1 d . . . Bi1 Bi 0.30085(5) 0.17903(4) 0.36272(3) 0.01779(10) Uani 1 1 d . . . Bi2 Bi 0.31709(5) 0.09505(4) 0.05737(3) 0.01579(10) Uani 1 1 d . . . Bi3 Bi 0.71226(5) 0.00808(4) 0.23213(3) 0.01485(10) Uani 1 1 d . . . C1 C -0.0483(13) 0.2623(10) 0.1917(8) 0.019(2) Uani 1 1 d . . . C2 C 0.0186(13) 0.4053(10) 0.1804(9) 0.019(2) Uani 1 1 d . . . C3 C -0.0618(14) 0.5406(10) 0.1399(8) 0.0191(19) Uani 1 1 d . . . H3 H -0.1740 0.5686 0.1046 0.023 Uiso 1 1 calc R . . C4 C 0.0714(13) 0.6265(10) 0.1660(9) 0.019(2) Uani 1 1 d . . . C5 C 0.0793(13) 0.7776(10) 0.1527(9) 0.0190(19) Uani 1 1 d . . . C6 C 0.7176(14) 0.1388(11) 0.4757(9) 0.024(2) Uani 1 1 d . . . C7 C 0.6923(13) 0.2942(11) 0.4345(9) 0.022(2) Uani 1 1 d . . . C8 C 0.7819(14) 0.4052(10) 0.4604(9) 0.021(2) Uani 1 1 d . . . H8 H 0.8782 0.3981 0.5085 0.025 Uiso 1 1 calc R . . C9 C 0.6866(12) 0.5273(10) 0.3943(8) 0.0170(19) Uani 1 1 d . . . C10 C 0.7023(13) 0.6812(12) 0.3778(8) 0.024(2) Uani 1 1 d . . . N1 N 0.1846(11) 0.4072(8) 0.2294(8) 0.0223(18) Uani 1 1 d . . . N2 N 0.2112(11) 0.5451(8) 0.2152(7) 0.0183(17) Uani 1 1 d . . . N3 N 0.5590(10) 0.3516(8) 0.3582(7) 0.0174(16) Uani 1 1 d . . . N4 N 0.5570(11) 0.4914(8) 0.3377(7) 0.0205(17) Uani 1 1 d . . . O1 O 0.0372(9) 0.1533(7) 0.2564(6) 0.0234(15) Uani 1 1 d . . . O2 O -0.1836(9) 0.2495(8) 0.1359(6) 0.0241(16) Uani 1 1 d . . . O3 O -0.0531(9) 0.8657(7) 0.1135(6) 0.0251(16) Uani 1 1 d . . . O4 O 0.2301(9) 0.8170(7) 0.1835(6) 0.0224(15) Uani 1 1 d . . . O5 O 0.6313(10) 0.0713(7) 0.4222(6) 0.0225(15) Uani 1 1 d . . . O6 O 0.8155(11) 0.0797(7) 0.5570(7) 0.040(2) Uani 1 1 d . . . O7 O 0.8053(11) 0.7315(8) 0.4279(7) 0.0310(17) Uani 1 1 d . . . O8 O 0.5809(9) 0.7608(7) 0.3051(6) 0.0219(15) Uani 1 1 d . . . O9 O 0.4396(9) 0.1166(7) 0.2275(6) 0.0199(14) Uani 1 1 d . . . O10 O 0.6001(9) 0.0056(7) 0.0779(5) 0.0165(13) Uani 1 1 d . . . O11 O 0.5568(11) 0.7073(8) 0.0532(7) 0.0293(17) Uani 1 1 d . . . H11A H 0.506(19) 0.758(16) -0.004(13) 0.06(5) Uiso 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 Cu1 0.0213(6) 0.0118(5) 0.0302(7) -0.0046(5) -0.0133(5) -0.0009(4) Bi1 0.02237(18) 0.01514(18) 0.01836(19) -0.00772(15) -0.00567(14) 0.00026(14) Bi2 0.01637(17) 0.01488(17) 0.01827(19) -0.00759(15) -0.00513(13) 0.00238(13) Bi3 0.01730(17) 0.01245(17) 0.01706(18) -0.00615(14) -0.00642(13) -0.00139(12) C1 0.025(5) 0.017(5) 0.009(4) 0.002(4) 0.010(4) -0.005(4) C2 0.020(4) 0.018(5) 0.024(5) -0.014(4) 0.000(4) -0.002(4) C3 0.022(4) 0.019(5) 0.020(5) -0.009(4) -0.009(4) 0.003(4) C4 0.019(4) 0.014(4) 0.027(5) -0.010(4) -0.001(4) -0.001(4) C5 0.021(4) 0.015(4) 0.019(5) -0.001(4) -0.002(4) -0.002(4) C6 0.026(5) 0.020(5) 0.019(5) 0.000(4) -0.003(4) 0.005(4) C7 0.024(5) 0.019(5) 0.026(5) -0.011(4) -0.011(4) -0.003(4) C8 0.026(5) 0.017(5) 0.020(5) -0.004(4) -0.006(4) -0.006(4) C9 0.015(4) 0.015(4) 0.021(5) -0.006(4) -0.004(4) 0.001(3) C10 0.016(4) 0.034(6) 0.014(5) 0.003(5) -0.006(4) 0.003(4) N1 0.026(4) 0.008(3) 0.034(5) -0.006(4) -0.009(4) -0.004(3) N2 0.022(4) 0.008(3) 0.028(5) -0.006(3) -0.012(3) -0.002(3) N3 0.019(4) 0.007(3) 0.028(5) -0.008(3) -0.007(3) 0.002(3) N4 0.022(4) 0.015(4) 0.028(5) -0.008(4) -0.015(4) 0.006(3) O1 0.024(3) 0.012(3) 0.035(4) -0.006(3) -0.013(3) -0.001(3) O2 0.022(3) 0.023(4) 0.031(4) -0.008(3) -0.017(3) -0.006(3) O3 0.024(3) 0.020(3) 0.032(4) -0.006(3) -0.011(3) 0.006(3) O4 0.025(3) 0.015(3) 0.028(4) -0.006(3) -0.013(3) 0.002(3) O5 0.033(4) 0.016(3) 0.023(4) -0.008(3) -0.013(3) -0.001(3) O6 0.047(5) 0.013(3) 0.059(6) 0.004(4) -0.044(5) -0.002(3) O7 0.045(4) 0.020(4) 0.033(4) -0.010(3) -0.023(4) 0.001(3) O8 0.021(3) 0.018(3) 0.024(4) -0.001(3) -0.009(3) -0.001(3) O9 0.019(3) 0.025(4) 0.022(4) -0.014(3) -0.008(3) 0.004(3) O10 0.020(3) 0.021(3) 0.014(3) -0.013(3) -0.006(3) 0.004(3) O11 0.038(4) 0.020(4) 0.028(4) -0.003(4) -0.008(4) -0.006(3) _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 Cu1 N2 1.950(7) . ? Cu1 N4 1.956(8) . ? Cu1 O8 1.991(7) . ? Cu1 O4 2.003(7) . ? Cu1 O11 2.304(8) . ? Bi1 O9 2.067(6) . ? Bi1 O1 2.450(7) . ? Bi1 N1 2.467(8) . ? Bi1 N3 2.549(7) . ? Bi1 O6 2.566(7) 2_656 ? Bi1 O5 2.594(7) . ? Bi2 O11 2.153(8) 2_665 ? Bi2 O10 2.153(6) . ? Bi2 O10 2.191(6) 2_655 ? Bi2 O9 2.397(6) . ? Bi2 O4 2.739(7) 1_545 ? Bi2 Bi2 3.5415(7) 2_655 ? Bi2 Bi3 3.5938(5) . ? Bi3 O10 2.118(6) . ? Bi3 O9 2.154(6) . ? Bi3 O2 2.404(7) 1_655 ? Bi3 O8 2.504(7) 1_545 ? Bi3 O5 2.575(6) . ? Bi3 O3 2.709(7) 1_645 ? C1 O2 1.266(12) . ? C1 O1 1.275(11) . ? C1 C2 1.471(13) . ? C2 N1 1.378(12) . ? C2 C3 1.378(13) . ? C3 C4 1.427(13) . ? C3 H3 0.9300 . ? C4 N2 1.309(12) . ? C4 C5 1.449(13) . ? C5 O3 1.265(11) . ? C5 O4 1.287(11) . ? C6 O6 1.235(12) . ? C6 O5 1.284(12) . ? C6 C7 1.457(13) . ? C7 N3 1.364(12) . ? C7 C8 1.428(13) . ? C8 C9 1.397(13) . ? C8 H8 0.9300 . ? C9 N4 1.330(12) . ? C9 C10 1.474(14) . ? C10 O7 1.216(12) . ? C10 O8 1.332(11) . ? N1 N2 1.335(10) . ? N3 N4 1.318(10) . ? O2 Bi3 2.404(7) 1_455 ? O3 Bi3 2.709(7) 1_465 ? O4 Bi2 2.739(7) 1_565 ? O6 Bi1 2.566(7) 2_656 ? O8 Bi3 2.504(7) 1_565 ? O10 Bi2 2.191(6) 2_655 ? O11 Bi2 2.153(8) 2_665 ? O11 H11A 0.82(14) . ? 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 Cu1 N4 97.5(3) . . ? N2 Cu1 O8 165.9(3) . . ? N4 Cu1 O8 81.2(3) . . ? N2 Cu1 O4 81.9(3) . . ? N4 Cu1 O4 165.1(3) . . ? O8 Cu1 O4 95.8(3) . . ? N2 Cu1 O11 94.2(3) . . ? N4 Cu1 O11 106.4(3) . . ? O8 Cu1 O11 99.6(3) . . ? O4 Cu1 O11 88.4(3) . . ? O9 Bi1 O1 77.8(2) . . ? O9 Bi1 N1 93.3(3) . . ? O1 Bi1 N1 65.9(2) . . ? O9 Bi1 N3 93.8(2) . . ? O1 Bi1 N3 142.1(2) . . ? N1 Bi1 N3 78.0(3) . . ? O9 Bi1 O6 85.0(3) . 2_656 ? O1 Bi1 O6 70.4(2) . 2_656 ? N1 Bi1 O6 135.6(2) . 2_656 ? N3 Bi1 O6 146.5(2) . 2_656 ? O9 Bi1 O5 71.3(2) . . ? O1 Bi1 O5 142.6(2) . . ? N1 Bi1 O5 135.2(2) . . ? N3 Bi1 O5 62.1(2) . . ? O6 Bi1 O5 86.1(2) 2_656 . ? O11 Bi2 O10 87.7(3) 2_665 . ? O11 Bi2 O10 90.5(3) 2_665 2_655 ? O10 Bi2 O10 70.8(3) . 2_655 ? O11 Bi2 O9 92.1(3) 2_665 . ? O10 Bi2 O9 67.8(2) . . ? O10 Bi2 O9 138.3(2) 2_655 . ? O11 Bi2 O4 167.3(3) 2_665 1_545 ? O10 Bi2 O4 80.7(2) . 1_545 ? O10 Bi2 O4 80.7(2) 2_655 1_545 ? O9 Bi2 O4 88.4(2) . 1_545 ? O11 Bi2 Bi2 88.9(2) 2_665 2_655 ? O10 Bi2 Bi2 35.73(15) . 2_655 ? O10 Bi2 Bi2 35.02(16) 2_655 2_655 ? O9 Bi2 Bi2 103.46(15) . 2_655 ? O4 Bi2 Bi2 78.61(14) 1_545 2_655 ? O11 Bi2 Bi3 91.8(2) 2_665 . ? O10 Bi2 Bi3 32.40(15) . . ? O10 Bi2 Bi3 102.84(16) 2_655 . ? O9 Bi2 Bi3 35.53(14) . . ? O4 Bi2 Bi3 81.27(14) 1_545 . ? Bi2 Bi2 Bi3 67.926(12) 2_655 . ? O10 Bi3 O9 73.2(2) . . ? O10 Bi3 O2 90.5(2) . 1_655 ? O9 Bi3 O2 81.4(2) . 1_655 ? O10 Bi3 O8 81.0(2) . 1_545 ? O9 Bi3 O8 95.2(2) . 1_545 ? O2 Bi3 O8 171.4(2) 1_655 1_545 ? O10 Bi3 O5 143.3(2) . . ? O9 Bi3 O5 70.5(2) . . ? O2 Bi3 O5 88.9(2) 1_655 . ? O8 Bi3 O5 97.4(2) 1_545 . ? O10 Bi3 O3 68.4(2) . 1_645 ? O9 Bi3 O3 141.5(2) . 1_645 ? O2 Bi3 O3 100.4(2) 1_655 1_645 ? O8 Bi3 O3 77.3(2) 1_545 1_645 ? O5 Bi3 O3 147.4(2) . 1_645 ? O10 Bi3 Bi2 33.00(16) . . ? O9 Bi3 Bi2 40.30(16) . . ? O2 Bi3 Bi2 87.70(15) 1_655 . ? O8 Bi3 Bi2 84.70(15) 1_545 . ? O5 Bi3 Bi2 110.37(15) . . ? O3 Bi3 Bi2 101.25(14) 1_645 . ? O2 C1 O1 121.6(9) . . ? O2 C1 C2 120.3(9) . . ? O1 C1 C2 118.0(9) . . ? N1 C2 C3 111.6(8) . . ? N1 C2 C1 115.6(8) . . ? C3 C2 C1 132.4(9) . . ? C2 C3 C4 102.1(8) . . ? C2 C3 H3 129.0 . . ? C4 C3 H3 129.0 . . ? N2 C4 C3 109.6(8) . . ? N2 C4 C5 116.4(8) . . ? C3 C4 C5 134.0(9) . . ? O3 C5 O4 121.9(9) . . ? O3 C5 C4 122.4(9) . . ? O4 C5 C4 115.7(8) . . ? O6 C6 O5 124.0(9) . . ? O6 C6 C7 120.8(10) . . ? O5 C6 C7 115.3(9) . . ? N3 C7 C8 110.3(8) . . ? N3 C7 C6 118.0(8) . . ? C8 C7 C6 131.7(9) . . ? C9 C8 C7 101.5(8) . . ? C9 C8 H8 129.3 . . ? C7 C8 H8 129.3 . . ? N4 C9 C8 110.6(8) . . ? N4 C9 C10 116.8(8) . . ? C8 C9 C10 132.7(9) . . ? O7 C10 O8 122.9(10) . . ? O7 C10 C9 125.2(9) . . ? O8 C10 C9 111.8(9) . . ? N2 N1 C2 105.2(7) . . ? N2 N1 Bi1 134.0(6) . . ? C2 N1 Bi1 117.7(6) . . ? C4 N2 N1 111.5(8) . . ? C4 N2 Cu1 113.0(6) . . ? N1 N2 Cu1 135.4(6) . . ? N4 N3 C7 106.8(8) . . ? N4 N3 Bi1 132.2(6) . . ? C7 N3 Bi1 114.5(6) . . ? N3 N4 C9 110.9(7) . . ? N3 N4 Cu1 134.8(6) . . ? C9 N4 Cu1 114.3(6) . . ? C1 O1 Bi1 121.4(6) . . ? C1 O2 Bi3 104.4(6) . 1_455 ? C5 O3 Bi3 127.2(6) . 1_465 ? C5 O4 Cu1 112.6(6) . . ? C5 O4 Bi2 111.8(6) . 1_565 ? Cu1 O4 Bi2 126.9(3) . 1_565 ? C6 O5 Bi3 134.1(6) . . ? C6 O5 Bi1 114.6(6) . . ? Bi3 O5 Bi1 92.9(2) . . ? C6 O6 Bi1 104.5(6) . 2_656 ? C10 O8 Cu1 115.9(6) . . ? C10 O8 Bi3 105.5(6) . 1_565 ? Cu1 O8 Bi3 134.1(3) . 1_565 ? Bi1 O9 Bi3 125.1(3) . . ? Bi1 O9 Bi2 129.3(3) . . ? Bi3 O9 Bi2 104.2(2) . . ? Bi3 O10 Bi2 114.6(3) . . ? Bi3 O10 Bi2 135.4(3) . 2_655 ? Bi2 O10 Bi2 109.2(3) . 2_655 ? Bi2 O11 Cu1 128.6(3) 2_665 . ? Bi2 O11 H11A 59(10) 2_665 . ? Cu1 O11 H11A 123(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O11 Bi2 Bi3 O10 -82.9(4) 2_665 . . . ? O10 Bi2 Bi3 O10 8.1(5) 2_655 . . . ? O9 Bi2 Bi3 O10 -174.0(4) . . . . ? O4 Bi2 Bi3 O10 86.4(4) 1_545 . . . ? Bi2 Bi2 Bi3 O10 5.3(3) 2_655 . . . ? O11 Bi2 Bi3 O9 91.1(3) 2_665 . . . ? O10 Bi2 Bi3 O9 174.0(4) . . . . ? O10 Bi2 Bi3 O9 -177.9(3) 2_655 . . . ? O4 Bi2 Bi3 O9 -99.6(3) 1_545 . . . ? Bi2 Bi2 Bi3 O9 179.2(3) 2_655 . . . ? O11 Bi2 Bi3 O2 11.6(3) 2_665 . . 1_655 ? O10 Bi2 Bi3 O2 94.5(4) . . . 1_655 ? O10 Bi2 Bi3 O2 102.6(2) 2_655 . . 1_655 ? O9 Bi2 Bi3 O2 -79.5(3) . . . 1_655 ? O4 Bi2 Bi3 O2 -179.1(2) 1_545 . . 1_655 ? Bi2 Bi2 Bi3 O2 99.76(17) 2_655 . . 1_655 ? O11 Bi2 Bi3 O8 -164.5(3) 2_665 . . 1_545 ? O10 Bi2 Bi3 O8 -81.6(4) . . . 1_545 ? O10 Bi2 Bi3 O8 -73.5(2) 2_655 . . 1_545 ? O9 Bi2 Bi3 O8 104.4(3) . . . 1_545 ? O4 Bi2 Bi3 O8 4.8(2) 1_545 . . 1_545 ? Bi2 Bi2 Bi3 O8 -76.34(16) 2_655 . . 1_545 ? O11 Bi2 Bi3 O5 99.6(3) 2_665 . . . ? O10 Bi2 Bi3 O5 -177.5(4) . . . . ? O10 Bi2 Bi3 O5 -169.4(2) 2_655 . . . ? O9 Bi2 Bi3 O5 8.5(3) . . . . ? O4 Bi2 Bi3 O5 -91.1(2) 1_545 . . . ? Bi2 Bi2 Bi3 O5 -172.24(16) 2_655 . . . ? O11 Bi2 Bi3 O3 -88.5(3) 2_665 . . 1_645 ? O10 Bi2 Bi3 O3 -5.7(4) . . . 1_645 ? O10 Bi2 Bi3 O3 2.4(2) 2_655 . . 1_645 ? O9 Bi2 Bi3 O3 -179.6(3) . . . 1_645 ? O4 Bi2 Bi3 O3 80.8(2) 1_545 . . 1_645 ? Bi2 Bi2 Bi3 O3 -0.42(15) 2_655 . . 1_645 ? O2 C1 C2 N1 -170.1(8) . . . . ? O1 C1 C2 N1 8.2(12) . . . . ? O2 C1 C2 C3 17.4(16) . . . . ? O1 C1 C2 C3 -164.3(10) . . . . ? N1 C2 C3 C4 1.2(11) . . . . ? C1 C2 C3 C4 173.9(10) . . . . ? C2 C3 C4 N2 0.4(11) . . . . ? C2 C3 C4 C5 -177.5(11) . . . . ? N2 C4 C5 O3 -175.3(9) . . . . ? C3 C4 C5 O3 2.5(18) . . . . ? N2 C4 C5 O4 4.6(13) . . . . ? C3 C4 C5 O4 -177.6(10) . . . . ? O6 C6 C7 N3 -169.5(10) . . . . ? O5 C6 C7 N3 10.1(14) . . . . ? O6 C6 C7 C8 9.5(18) . . . . ? O5 C6 C7 C8 -170.9(10) . . . . ? N3 C7 C8 C9 0.8(11) . . . . ? C6 C7 C8 C9 -178.2(11) . . . . ? C7 C8 C9 N4 0.3(11) . . . . ? C7 C8 C9 C10 179.8(10) . . . . ? N4 C9 C10 O7 175.6(9) . . . . ? C8 C9 C10 O7 -3.8(18) . . . . ? N4 C9 C10 O8 -0.8(12) . . . . ? C8 C9 C10 O8 179.8(10) . . . . ? C3 C2 N1 N2 -2.3(11) . . . . ? C1 C2 N1 N2 -176.4(8) . . . . ? C3 C2 N1 Bi1 160.7(6) . . . . ? C1 C2 N1 Bi1 -13.3(10) . . . . ? O9 Bi1 N1 N2 -118.0(9) . . . . ? O1 Bi1 N1 N2 166.9(10) . . . . ? N3 Bi1 N1 N2 -24.8(9) . . . . ? O6 Bi1 N1 N2 155.8(8) 2_656 . . . ? O5 Bi1 N1 N2 -51.5(10) . . . . ? O9 Bi1 N1 C2 85.0(7) . . . . ? O1 Bi1 N1 C2 9.9(6) . . . . ? N3 Bi1 N1 C2 178.2(7) . . . . ? O6 Bi1 N1 C2 -1.2(9) 2_656 . . . ? O5 Bi1 N1 C2 151.6(6) . . . . ? C3 C4 N2 N1 -1.9(11) . . . . ? C5 C4 N2 N1 176.4(8) . . . . ? C3 C4 N2 Cu1 174.7(6) . . . . ? C5 C4 N2 Cu1 -7.0(11) . . . . ? C2 N1 N2 C4 2.6(11) . . . . ? Bi1 N1 N2 C4 -156.3(7) . . . . ? C2 N1 N2 Cu1 -173.0(7) . . . . ? Bi1 N1 N2 Cu1 28.1(14) . . . . ? N4 Cu1 N2 C4 170.4(7) . . . . ? O8 Cu1 N2 C4 86.8(14) . . . . ? O4 Cu1 N2 C4 5.4(7) . . . . ? O11 Cu1 N2 C4 -82.3(7) . . . . ? N4 Cu1 N2 N1 -14.0(10) . . . . ? O8 Cu1 N2 N1 -97.7(14) . . . . ? O4 Cu1 N2 N1 -179.0(10) . . . . ? O11 Cu1 N2 N1 93.2(10) . . . . ? C8 C7 N3 N4 -1.7(11) . . . . ? C6 C7 N3 N4 177.5(9) . . . . ? C8 C7 N3 Bi1 -157.1(6) . . . . ? C6 C7 N3 Bi1 22.2(11) . . . . ? O9 Bi1 N3 N4 118.6(8) . . . . ? O1 Bi1 N3 N4 43.6(10) . . . . ? N1 Bi1 N3 N4 26.0(8) . . . . ? O6 Bi1 N3 N4 -154.7(8) 2_656 . . . ? O5 Bi1 N3 N4 -174.9(9) . . . . ? O9 Bi1 N3 C7 -94.0(7) . . . . ? O1 Bi1 N3 C7 -169.0(6) . . . . ? N1 Bi1 N3 C7 173.4(7) . . . . ? O6 Bi1 N3 C7 -7.4(9) 2_656 . . . ? O5 Bi1 N3 C7 -27.5(6) . . . . ? C7 N3 N4 C9 1.9(11) . . . . ? Bi1 N3 N4 C9 151.1(7) . . . . ? C7 N3 N4 Cu1 -180.0(7) . . . . ? Bi1 N3 N4 Cu1 -30.8(14) . . . . ? C8 C9 N4 N3 -1.5(11) . . . . ? C10 C9 N4 N3 179.0(8) . . . . ? C8 C9 N4 Cu1 -180.0(6) . . . . ? C10 C9 N4 Cu1 0.5(11) . . . . ? N2 Cu1 N4 N3 16.0(10) . . . . ? O8 Cu1 N4 N3 -178.2(10) . . . . ? O4 Cu1 N4 N3 102.6(14) . . . . ? O11 Cu1 N4 N3 -80.7(9) . . . . ? N2 Cu1 N4 C9 -166.0(7) . . . . ? O8 Cu1 N4 C9 -0.1(7) . . . . ? O4 Cu1 N4 C9 -79.3(14) . . . . ? O11 Cu1 N4 C9 97.4(7) . . . . ? O2 C1 O1 Bi1 179.5(6) . . . . ? C2 C1 O1 Bi1 1.2(11) . . . . ? O9 Bi1 O1 C1 -105.1(7) . . . . ? N1 Bi1 O1 C1 -5.8(6) . . . . ? N3 Bi1 O1 C1 -24.7(9) . . . . ? O6 Bi1 O1 C1 166.0(7) 2_656 . . . ? O5 Bi1 O1 C1 -139.8(6) . . . . ? O1 C1 O2 Bi3 18.6(10) . . . 1_455 ? C2 C1 O2 Bi3 -163.2(7) . . . 1_455 ? O4 C5 O3 Bi3 -67.2(11) . . . 1_465 ? C4 C5 O3 Bi3 112.7(9) . . . 1_465 ? O3 C5 O4 Cu1 -179.9(7) . . . . ? C4 C5 O4 Cu1 0.1(10) . . . . ? O3 C5 O4 Bi2 -29.8(11) . . . 1_565 ? C4 C5 O4 Bi2 150.3(7) . . . 1_565 ? N2 Cu1 O4 C5 -3.0(6) . . . . ? N4 Cu1 O4 C5 -91.7(13) . . . . ? O8 Cu1 O4 C5 -169.0(6) . . . . ? O11 Cu1 O4 C5 91.5(6) . . . . ? N2 Cu1 O4 Bi2 -147.7(4) . . . 1_565 ? N4 Cu1 O4 Bi2 123.6(11) . . . 1_565 ? O8 Cu1 O4 Bi2 46.3(4) . . . 1_565 ? O11 Cu1 O4 Bi2 -53.2(4) . . . 1_565 ? O6 C6 O5 Bi3 -95.9(12) . . . . ? C7 C6 O5 Bi3 84.5(11) . . . . ? O6 C6 O5 Bi1 142.8(9) . . . . ? C7 C6 O5 Bi1 -36.9(10) . . . . ? O10 Bi3 O5 C6 -134.4(8) . . . . ? O9 Bi3 O5 C6 -126.3(9) . . . . ? O2 Bi3 O5 C6 -45.0(8) 1_655 . . . ? O8 Bi3 O5 C6 140.8(8) 1_545 . . . ? O3 Bi3 O5 C6 62.8(10) 1_645 . . . ? Bi2 Bi3 O5 C6 -132.2(8) . . . . ? O10 Bi3 O5 Bi1 -5.5(5) . . . . ? O9 Bi3 O5 Bi1 2.6(2) . . . . ? O2 Bi3 O5 Bi1 83.9(2) 1_655 . . . ? O8 Bi3 O5 Bi1 -90.2(2) 1_545 . . . ? O3 Bi3 O5 Bi1 -168.2(3) 1_645 . . . ? Bi2 Bi3 O5 Bi1 -3.2(2) . . . . ? O9 Bi1 O5 C6 139.3(7) . . . . ? O1 Bi1 O5 C6 175.3(6) . . . . ? N1 Bi1 O5 C6 64.1(7) . . . . ? N3 Bi1 O5 C6 34.4(6) . . . . ? O6 Bi1 O5 C6 -134.6(7) 2_656 . . . ? O9 Bi1 O5 Bi3 -2.7(2) . . . . ? O1 Bi1 O5 Bi3 33.3(4) . . . . ? N1 Bi1 O5 Bi3 -78.0(4) . . . . ? N3 Bi1 O5 Bi3 -107.7(3) . . . . ? O6 Bi1 O5 Bi3 83.3(3) 2_656 . . . ? O5 C6 O6 Bi1 -21.3(12) . . . 2_656 ? C7 C6 O6 Bi1 158.4(8) . . . 2_656 ? O7 C10 O8 Cu1 -175.8(8) . . . . ? C9 C10 O8 Cu1 0.7(10) . . . . ? O7 C10 O8 Bi3 24.4(11) . . . 1_565 ? C9 C10 O8 Bi3 -159.1(6) . . . 1_565 ? N2 Cu1 O8 C10 85.4(13) . . . . ? N4 Cu1 O8 C10 -0.3(7) . . . . ? O4 Cu1 O8 C10 165.0(6) . . . . ? O11 Cu1 O8 C10 -105.7(7) . . . . ? N2 Cu1 O8 Bi3 -122.3(11) . . . 1_565 ? N4 Cu1 O8 Bi3 152.0(5) . . . 1_565 ? O4 Cu1 O8 Bi3 -42.7(5) . . . 1_565 ? O11 Cu1 O8 Bi3 46.6(5) . . . 1_565 ? O1 Bi1 O9 Bi3 -154.6(4) . . . . ? N1 Bi1 O9 Bi3 141.0(4) . . . . ? N3 Bi1 O9 Bi3 62.9(4) . . . . ? O6 Bi1 O9 Bi3 -83.5(4) 2_656 . . . ? O5 Bi1 O9 Bi3 4.0(3) . . . . ? O1 Bi1 O9 Bi2 9.7(4) . . . . ? N1 Bi1 O9 Bi2 -54.8(4) . . . . ? N3 Bi1 O9 Bi2 -132.9(4) . . . . ? O6 Bi1 O9 Bi2 80.7(4) 2_656 . . . ? O5 Bi1 O9 Bi2 168.2(5) . . . . ? O10 Bi3 O9 Bi1 170.9(5) . . . . ? O2 Bi3 O9 Bi1 -96.0(4) 1_655 . . . ? O8 Bi3 O9 Bi1 91.9(4) 1_545 . . . ? O5 Bi3 O9 Bi1 -4.1(3) . . . . ? O3 Bi3 O9 Bi1 168.0(3) 1_645 . . . ? Bi2 Bi3 O9 Bi1 167.5(6) . . . . ? O10 Bi3 O9 Bi2 3.4(2) . . . . ? O2 Bi3 O9 Bi2 96.6(3) 1_655 . . . ? O8 Bi3 O9 Bi2 -75.5(3) 1_545 . . . ? O5 Bi3 O9 Bi2 -171.5(3) . . . . ? O3 Bi3 O9 Bi2 0.6(5) 1_645 . . . ? O11 Bi2 O9 Bi1 103.1(4) 2_665 . . . ? O10 Bi2 O9 Bi1 -170.2(5) . . . . ? O10 Bi2 O9 Bi1 -163.7(3) 2_655 . . . ? O4 Bi2 O9 Bi1 -89.6(4) 1_545 . . . ? Bi2 Bi2 O9 Bi1 -167.5(3) 2_655 . . . ? Bi3 Bi2 O9 Bi1 -166.8(6) . . . . ? O11 Bi2 O9 Bi3 -90.2(3) 2_665 . . . ? O10 Bi2 O9 Bi3 -3.5(2) . . . . ? O10 Bi2 O9 Bi3 3.0(5) 2_655 . . . ? O4 Bi2 O9 Bi3 77.2(3) 1_545 . . . ? Bi2 Bi2 O9 Bi3 -0.7(3) 2_655 . . . ? O9 Bi3 O10 Bi2 -4.1(3) . . . . ? O2 Bi3 O10 Bi2 -85.0(3) 1_655 . . . ? O8 Bi3 O10 Bi2 94.2(3) 1_545 . . . ? O5 Bi3 O10 Bi2 3.9(6) . . . . ? O3 Bi3 O10 Bi2 174.0(4) 1_645 . . . ? O9 Bi3 O10 Bi2 -172.8(5) . . . 2_655 ? O2 Bi3 O10 Bi2 106.3(5) 1_655 . . 2_655 ? O8 Bi3 O10 Bi2 -74.6(4) 1_545 . . 2_655 ? O5 Bi3 O10 Bi2 -164.8(3) . . . 2_655 ? O3 Bi3 O10 Bi2 5.3(4) 1_645 . . 2_655 ? Bi2 Bi3 O10 Bi2 -168.7(7) . . . 2_655 ? O11 Bi2 O10 Bi3 97.0(3) 2_665 . . . ? O10 Bi2 O10 Bi3 -171.6(5) 2_655 . . . ? O9 Bi2 O10 Bi3 3.8(3) . . . . ? O4 Bi2 O10 Bi3 -88.3(3) 1_545 . . . ? Bi2 Bi2 O10 Bi3 -171.6(5) 2_655 . . . ? O11 Bi2 O10 Bi2 -91.4(3) 2_665 . . 2_655 ? O10 Bi2 O10 Bi2 0.0 2_655 . . 2_655 ? O9 Bi2 O10 Bi2 175.4(4) . . . 2_655 ? O4 Bi2 O10 Bi2 83.4(3) 1_545 . . 2_655 ? Bi3 Bi2 O10 Bi2 171.6(5) . . . 2_655 ? N2 Cu1 O11 Bi2 140.3(5) . . . 2_665 ? N4 Cu1 O11 Bi2 -120.6(5) . . . 2_665 ? O8 Cu1 O11 Bi2 -37.1(5) . . . 2_665 ? O4 Cu1 O11 Bi2 58.5(5) . . . 2_665 ? 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 O11 H11A O10 0.82(14) 2.33(14) 2.984(10) 138(13) 2_665 O11 H11A O9 0.82(14) 2.58(15) 3.281(11) 144(12) 2_665 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 3.420 _refine_diff_density_min -3.096 _refine_diff_density_rms 0.416