data_compoundI _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Bi-2,6-pyridine dicarboxylate' _chemical_melting_point ? _chemical_formula_moiety 'C32 H20 Bi2 N6 O18' _chemical_formula_sum 'C32 H20 Bi2 N6 O18' _chemical_formula_weight 1194.50 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source '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' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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' _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 7.1116(11) _cell_length_b 10.9029(14) _cell_length_c 12.2212(18) _cell_angle_alpha 113.391(4) _cell_angle_beta 97.047(4) _cell_angle_gamma 92.829(4) _cell_volume 858.1(2) _cell_formula_units_Z 1 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used 3018 _cell_measurement_theta_min 2.05 _cell_measurement_theta_max 25.07 _exptl_crystal_description 'diamond' _exptl_crystal_colour 'light brown' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 564 _exptl_absorpt_coefficient_mu 10.334 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.1475 _exptl_absorpt_correction_T_max 0.5315 _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction,2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 300(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Xcalibur,Eos(Nova) CCD detector' _diffrn_measurement_method 'f\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16773 _diffrn_reflns_av_R_equivalents 0.0682 _diffrn_reflns_av_sigmaI/netI 0.0480 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 25.07 _reflns_number_total 3018 _reflns_number_gt 2678 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro CCD (Oxford Diffraction, 2009)' _computing_cell_refinement 'CrysAlisPro CCD (Oxford Diffraction, 2009)' _computing_data_reduction 'CrysAlisPro RED (Oxford Diffraction, 2009)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0365P)^2^+0.5807P] 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 3018 _refine_ls_number_parameters 272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0378 _refine_ls_R_factor_gt 0.0305 _refine_ls_wR_factor_ref 0.0733 _refine_ls_wR_factor_gt 0.0702 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 0.62373(3) 0.68915(2) 0.63610(2) 0.02757(10) Uani 1 1 d . . . O1 O 0.5564(7) 0.5340(5) 0.4058(4) 0.0416(12) Uani 1 1 d . . . O2 O 0.5298(12) 0.5211(6) 0.2177(5) 0.086(2) Uani 1 1 d . . . O3 O 0.6938(7) 0.9202(4) 0.7348(4) 0.0356(11) Uani 1 1 d . . . O4 O 0.7957(9) 1.1151(5) 0.7339(5) 0.0586(16) Uani 1 1 d . . . O5 O 0.7876(7) 0.7073(5) 0.8414(4) 0.0429(13) Uani 1 1 d . . . O6 O 0.7648(8) 0.7600(6) 1.0355(5) 0.0532(15) Uani 1 1 d . . . O7 O 0.3205(6) 0.7152(5) 0.5695(4) 0.0383(12) Uani 1 1 d . . . O8 O 0.0249(7) 0.7544(7) 0.6034(5) 0.0579(16) Uani 1 1 d . . . O9 O 0.924(2) 0.4991(14) 0.6172(13) 0.072(6) Uani 0.53(2) 1 d P A 1 O9A O 0.957(3) 0.417(2) 0.6597(14) 0.097(8) Uani 0.47(2) 1 d P A 2 N1 N 0.6573(7) 0.7992(5) 0.4963(5) 0.0263(12) Uani 1 1 d . . . N2 N 0.4363(7) 0.7661(5) 0.7976(4) 0.0247(12) Uani 1 1 d . . . N3 N 0.117(3) 0.6216(18) 1.0721(10) 0.238(12) Uani 1 1 d . . . C1 C 0.6334(9) 0.7308(7) 0.3765(6) 0.0304(15) Uani 1 1 d . . . C2 C 0.6684(10) 0.7936(7) 0.3016(6) 0.0362(17) Uani 1 1 d . . . H2 H 0.6467 0.7460 0.2182 0.043 Uiso 1 1 calc R . . C3 C 0.7361(10) 0.9282(8) 0.3525(6) 0.0410(18) Uani 1 1 d . . . H3 H 0.7660 0.9715 0.3040 0.049 Uiso 1 1 calc R . . C4 C 0.7590(10) 0.9980(7) 0.4766(6) 0.0369(17) Uani 1 1 d . . . H4 H 0.8004 1.0894 0.5126 0.044 Uiso 1 1 calc R . . C5 C 0.7192(9) 0.9292(7) 0.5455(6) 0.0276(15) Uani 1 1 d . . . C6 C 0.5680(11) 0.5823(8) 0.3282(6) 0.0432(19) Uani 1 1 d . . . C7 C 0.7385(10) 0.9955(7) 0.6818(6) 0.0350(17) Uani 1 1 d . . . C8 C 0.2624(9) 0.7977(7) 0.7719(6) 0.0308(15) Uani 1 1 d . . . C9 C 0.1543(10) 0.8619(7) 0.8597(6) 0.0345(16) Uani 1 1 d . . . H9 H 0.0343 0.8844 0.8399 0.041 Uiso 1 1 calc R . . C10 C 0.2291(11) 0.8916(8) 0.9780(6) 0.0414(19) Uani 1 1 d . . . H10 H 0.1596 0.9356 1.0394 0.050 Uiso 1 1 calc R . . C11 C 0.4074(10) 0.8563(7) 1.0058(6) 0.0355(17) Uani 1 1 d . . . H11 H 0.4581 0.8750 1.0853 0.043 Uiso 1 1 calc R . . C12 C 0.5090(9) 0.7923(6) 0.9124(5) 0.0273(15) Uani 1 1 d . . . C13 C 0.1948(9) 0.7542(8) 0.6397(6) 0.0358(17) Uani 1 1 d . . . C14 C 0.7047(10) 0.7498(7) 0.9316(6) 0.0317(16) Uani 1 1 d . . . C15 C 0.1377(15) 0.5412(10) 0.9436(10) 0.077(3) Uani 1 1 d . . . H15A H 0.1202 0.5978 0.8995 0.093 Uiso 1 1 calc R . . H15B H 0.2667 0.5164 0.9409 0.093 Uiso 1 1 calc R . . C16 C 0.0037(14) 0.4177(14) 0.8810(9) 0.110(5) Uani 1 1 d . . . H16A H -0.0653 0.4259 0.8110 0.132 Uiso 1 1 calc R . . H16B H 0.0815 0.3446 0.8502 0.132 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 0.03344(15) 0.02824(17) 0.02063(14) 0.00788(11) 0.00880(10) 0.00611(10) O1 0.067(3) 0.024(3) 0.031(3) 0.006(2) 0.017(2) -0.007(2) O2 0.166(7) 0.050(4) 0.030(3) 0.007(3) 0.020(4) -0.038(4) O3 0.054(3) 0.029(3) 0.022(2) 0.007(2) 0.008(2) 0.003(2) O4 0.095(5) 0.035(4) 0.037(3) 0.008(3) 0.010(3) -0.013(3) O5 0.037(3) 0.069(4) 0.037(3) 0.034(3) 0.011(2) 0.017(3) O6 0.057(3) 0.075(4) 0.033(3) 0.029(3) -0.003(2) 0.015(3) O7 0.030(2) 0.064(3) 0.023(2) 0.019(2) 0.0051(19) 0.009(2) O8 0.038(3) 0.102(5) 0.037(3) 0.031(3) 0.002(2) 0.019(3) O9 0.087(10) 0.056(9) 0.068(10) 0.019(7) 0.014(7) 0.006(7) O9A 0.130(15) 0.109(17) 0.050(10) 0.033(10) 0.001(9) 0.020(11) N1 0.027(3) 0.026(3) 0.024(3) 0.009(2) 0.003(2) 0.004(2) N2 0.030(3) 0.027(3) 0.017(3) 0.007(2) 0.008(2) 0.005(2) N3 0.32(2) 0.278(19) 0.043(6) 0.025(9) 0.000(9) -0.240(17) C1 0.034(4) 0.036(4) 0.021(3) 0.011(3) 0.006(3) 0.001(3) C2 0.048(4) 0.040(5) 0.024(3) 0.015(3) 0.010(3) 0.002(3) C3 0.054(5) 0.049(5) 0.033(4) 0.029(4) 0.010(3) 0.006(4) C4 0.045(4) 0.031(4) 0.038(4) 0.018(3) 0.006(3) 0.001(3) C5 0.030(3) 0.026(4) 0.030(4) 0.014(3) 0.004(3) 0.008(3) C6 0.058(5) 0.039(5) 0.024(4) 0.002(3) 0.016(3) -0.005(4) C7 0.046(4) 0.028(4) 0.028(4) 0.008(3) 0.006(3) 0.007(3) C8 0.033(4) 0.036(4) 0.025(3) 0.014(3) 0.007(3) 0.000(3) C9 0.033(4) 0.037(4) 0.032(4) 0.010(3) 0.008(3) 0.009(3) C10 0.055(5) 0.041(5) 0.024(4) 0.005(3) 0.017(3) 0.012(4) C11 0.047(4) 0.037(4) 0.018(3) 0.007(3) 0.006(3) 0.009(3) C12 0.037(4) 0.026(4) 0.018(3) 0.009(3) 0.002(3) 0.004(3) C13 0.027(4) 0.057(5) 0.025(4) 0.019(3) 0.003(3) 0.010(3) C14 0.038(4) 0.034(4) 0.027(4) 0.018(3) 0.001(3) 0.001(3) C15 0.088(8) 0.071(7) 0.082(8) 0.031(6) 0.047(6) 0.008(6) C16 0.052(6) 0.151(12) 0.043(6) -0.043(7) -0.002(5) -0.004(7) _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 O7 2.282(4) . ? Bi1 O3 2.316(5) . ? Bi1 N2 2.412(5) . ? Bi1 N1 2.473(5) . ? Bi1 O1 2.523(5) 2_666 ? Bi1 O5 2.562(5) . ? Bi1 O1 2.612(5) . ? O1 C6 1.263(9) . ? O1 Bi1 2.523(5) 2_666 ? O2 C6 1.233(9) . ? O3 C7 1.281(8) . ? O4 C7 1.223(9) . ? O5 C14 1.248(8) . ? O6 C14 1.247(8) . ? O7 C13 1.285(8) . ? O8 C13 1.235(8) . ? N1 C5 1.327(8) . ? N1 C1 1.338(8) . ? N2 C8 1.334(8) . ? N2 C12 1.345(7) . ? N3 C16 1.239(15) 2_567 ? N3 C15 1.494(16) . ? C1 C2 1.380(9) . ? C1 C6 1.511(10) . ? C2 C3 1.380(10) . ? C3 C4 1.384(10) . ? C4 C5 1.376(10) . ? C5 C7 1.514(9) . ? C8 C9 1.376(9) . ? C8 C13 1.499(9) . ? C9 C10 1.379(10) . ? C10 C11 1.385(10) . ? C11 C12 1.390(9) . ? C12 C14 1.509(9) . ? C15 C16 1.478(14) . ? C16 N3 1.239(15) 2_567 ? 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 O7 Bi1 O3 90.35(17) . . ? O7 Bi1 N2 68.10(16) . . ? O3 Bi1 N2 72.54(17) . . ? O7 Bi1 N1 74.65(17) . . ? O3 Bi1 N1 67.14(16) . . ? N2 Bi1 N1 123.84(17) . . ? O7 Bi1 O1 77.42(18) . 2_666 ? O3 Bi1 O1 154.35(17) . 2_666 ? N2 Bi1 O1 81.96(16) . 2_666 ? N1 Bi1 O1 128.77(16) . 2_666 ? O7 Bi1 O5 132.31(15) . . ? O3 Bi1 O5 80.06(16) . . ? N2 Bi1 O5 64.43(16) . . ? N1 Bi1 O5 138.37(17) . . ? O1 Bi1 O5 91.54(16) 2_666 . ? O7 Bi1 O1 73.94(16) . . ? O3 Bi1 O1 130.44(15) . . ? N2 Bi1 O1 135.70(16) . . ? N1 Bi1 O1 63.42(16) . . ? O1 Bi1 O1 67.99(18) 2_666 . ? O5 Bi1 O1 143.80(17) . . ? C6 O1 Bi1 124.6(5) . 2_666 ? C6 O1 Bi1 120.7(4) . . ? Bi1 O1 Bi1 112.01(18) 2_666 . ? C7 O3 Bi1 123.4(4) . . ? C14 O5 Bi1 120.5(4) . . ? C13 O7 Bi1 122.7(4) . . ? C5 N1 C1 120.1(6) . . ? C5 N1 Bi1 116.9(4) . . ? C1 N1 Bi1 122.6(4) . . ? C8 N2 C12 120.0(5) . . ? C8 N2 Bi1 117.3(4) . . ? C12 N2 Bi1 122.2(4) . . ? C16 N3 C15 120.0(10) 2_567 . ? N1 C1 C2 121.1(6) . . ? N1 C1 C6 116.7(6) . . ? C2 C1 C6 122.2(6) . . ? C3 C2 C1 118.9(6) . . ? C2 C3 C4 119.4(7) . . ? C5 C4 C3 118.5(7) . . ? N1 C5 C4 121.9(6) . . ? N1 C5 C7 115.1(6) . . ? C4 C5 C7 123.0(6) . . ? O2 C6 O1 126.7(7) . . ? O2 C6 C1 117.0(7) . . ? O1 C6 C1 116.3(6) . . ? O4 C7 O3 124.4(7) . . ? O4 C7 C5 119.0(7) . . ? O3 C7 C5 116.6(6) . . ? N2 C8 C9 122.5(6) . . ? N2 C8 C13 114.1(5) . . ? C9 C8 C13 123.4(6) . . ? C8 C9 C10 118.0(6) . . ? C9 C10 C11 120.2(6) . . ? C10 C11 C12 118.7(6) . . ? N2 C12 C11 120.7(6) . . ? N2 C12 C14 115.9(5) . . ? C11 C12 C14 123.5(6) . . ? O8 C13 O7 123.6(6) . . ? O8 C13 C8 119.8(6) . . ? O7 C13 C8 116.6(5) . . ? O6 C14 O5 127.3(7) . . ? O6 C14 C12 116.4(6) . . ? O5 C14 C12 116.3(6) . . ? C16 C15 N3 115.1(8) . . ? N3 C16 C15 124.8(10) 2_567 . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.07 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.544 _refine_diff_density_min -1.034 _refine_diff_density_rms 0.152 ######END####### data_compoundII _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Bi-imidazole dicarboxylate' _chemical_melting_point ? _chemical_formula_moiety 'C10 H4 Bi N4 O8' _chemical_formula_sum 'C10 H4 Bi N4 O8' _chemical_formula_weight 517.15 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' '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 'Triclinic' _symmetry_space_group_name_H-M 'P-1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9550(7) _cell_length_b 6.9973(7) _cell_length_c 12.8905(12) _cell_angle_alpha 81.541(8) _cell_angle_beta 81.012(8) _cell_angle_gamma 78.708(8) _cell_volume 603.22(10) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2233 _cell_measurement_theta_min 2.99 _cell_measurement_theta_max 26.00 _exptl_crystal_description 'rectangular' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.847 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 478 _exptl_absorpt_coefficient_mu 14.673 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.3216 _exptl_absorpt_correction_T_max 0.6673 _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction,2009)' _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 'Oxford Xcalibur,Eos(Nova) CCD detector' _diffrn_measurement_method 'f\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7805 _diffrn_reflns_av_R_equivalents 0.0505 _diffrn_reflns_av_sigmaI/netI 0.0434 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2374 _reflns_number_gt 2233 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro CCD (Oxford Diffraction, 2009)' _computing_cell_refinement 'CrysAlisPro CCD (Oxford Diffraction, 2009)' _computing_data_reduction 'CrysAlisPro RED (Oxford Diffraction, 2009)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0359P)^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 2374 _refine_ls_number_parameters 212 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0292 _refine_ls_R_factor_gt 0.0267 _refine_ls_wR_factor_ref 0.0652 _refine_ls_wR_factor_gt 0.0635 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 0.02422(3) 0.88349(3) 0.858598(16) 0.01504(9) Uani 1 1 d . . . O1 O -0.2661(6) 0.7581(5) 0.8604(3) 0.0186(9) Uani 1 1 d . . . O6 O 0.2290(7) 1.1753(6) 0.5396(4) 0.0291(11) Uani 1 1 d . . . O5 O 0.1166(6) 1.1137(6) 0.7118(3) 0.0223(10) Uani 1 1 d . . . O2 O -0.5929(6) 0.8045(6) 0.8670(4) 0.0246(10) Uani 1 1 d . . . O3 O -0.8868(6) 1.1477(6) 0.9426(3) 0.0184(9) Uani 1 1 d . . . O4 O -0.8753(6) 1.4655(6) 0.8932(4) 0.0239(10) Uani 1 1 d . . . O7 O 0.3862(9) 0.6554(8) 0.3608(4) 0.0508(16) Uani 1 1 d . . . O8 O 0.3489(8) 0.9717(7) 0.3793(4) 0.0439(14) Uani 1 1 d . . . H1 H 0.3053 1.0412 0.4266 0.066 Uiso 1 1 calc R . . N1 N -0.2522(7) 1.1313(6) 0.8573(4) 0.0166(10) Uani 1 1 d . . . N3 N 0.0910(9) 0.7436(8) 0.6926(4) 0.0289(13) Uani 1 1 d . . . N4 N 0.1893(9) 0.5671(8) 0.5623(4) 0.0299(13) Uani 1 1 d . . . N2 N -0.4732(6) 1.3975(6) 0.8750(4) 0.0176(11) Uani 1 1 d . . . C1 C -0.4345(8) 1.0786(8) 0.8705(4) 0.0149(12) Uani 1 1 d . . . C2 C -0.5779(8) 1.2470(8) 0.8812(4) 0.0144(12) Uani 1 1 d . . . C3 C -0.2794(9) 1.3244(8) 0.8605(5) 0.0195(13) Uani 1 1 d . . . H3 H -0.1788 1.3974 0.8537 0.023 Uiso 1 1 calc R . . C4 C -0.4374(8) 0.8686(7) 0.8650(4) 0.0156(12) Uani 1 1 d . . . C5 C -0.7935(9) 1.2927(8) 0.9064(4) 0.0163(12) Uani 1 1 d . . . C6 C 0.1707(9) 0.8571(8) 0.6080(5) 0.0221(14) Uani 1 1 d . . . C7 C 0.2374(10) 0.7487(9) 0.5244(5) 0.0263(15) Uani 1 1 d . . . C8 C 0.1079(12) 0.5701(9) 0.6606(6) 0.0361(18) Uani 1 1 d . . . H8 H 0.0668 0.4623 0.7030 0.043 Uiso 1 1 calc R . . C9 C 0.1725(9) 1.0640(9) 0.6190(5) 0.0229(14) Uani 1 1 d . . . C10 C 0.3286(11) 0.7878(10) 0.4144(5) 0.0304(16) Uani 1 1 d . . . H2 H 0.218(9) 0.453(9) 0.533(5) 0.015(15) 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 Bi1 0.01339(13) 0.00907(13) 0.02218(15) -0.00426(9) 0.00045(9) -0.00125(9) O1 0.014(2) 0.0074(18) 0.036(2) -0.0039(17) -0.0045(18) -0.0016(16) O6 0.044(3) 0.014(2) 0.029(3) -0.0005(19) 0.001(2) -0.010(2) O5 0.030(2) 0.012(2) 0.023(2) -0.0020(17) 0.004(2) -0.0049(18) O2 0.013(2) 0.010(2) 0.052(3) -0.007(2) -0.006(2) -0.0021(17) O3 0.018(2) 0.017(2) 0.022(2) -0.0052(17) 0.0026(18) -0.0106(17) O4 0.018(2) 0.012(2) 0.040(3) -0.0037(19) -0.002(2) 0.0014(17) O7 0.077(4) 0.035(3) 0.035(3) -0.016(2) 0.007(3) -0.001(3) O8 0.060(4) 0.032(3) 0.034(3) -0.003(2) 0.009(3) -0.006(3) N1 0.015(2) 0.008(2) 0.026(3) -0.002(2) -0.001(2) -0.0005(19) N3 0.048(4) 0.018(3) 0.022(3) -0.004(2) 0.002(3) -0.011(3) N4 0.052(4) 0.017(3) 0.023(3) -0.007(2) -0.006(3) -0.008(3) N2 0.014(3) 0.011(2) 0.028(3) -0.003(2) -0.002(2) -0.003(2) C1 0.017(3) 0.010(3) 0.019(3) 0.000(2) -0.004(2) -0.005(2) C2 0.017(3) 0.007(3) 0.020(3) -0.005(2) -0.001(2) -0.004(2) C3 0.014(3) 0.011(3) 0.034(4) -0.003(3) -0.004(3) -0.005(2) C4 0.019(3) 0.007(3) 0.021(3) -0.002(2) -0.003(3) -0.001(2) C5 0.018(3) 0.016(3) 0.015(3) -0.005(2) 0.003(2) -0.006(2) C6 0.027(3) 0.013(3) 0.026(3) -0.004(2) 0.001(3) -0.003(3) C7 0.032(4) 0.019(3) 0.027(3) -0.004(3) -0.001(3) -0.004(3) C8 0.061(5) 0.015(3) 0.033(4) -0.001(3) 0.000(4) -0.015(3) C9 0.024(3) 0.016(3) 0.030(4) -0.006(3) -0.002(3) -0.005(3) C10 0.035(4) 0.026(4) 0.028(4) -0.007(3) -0.002(3) 0.000(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 Bi1 N1 2.323(5) . ? Bi1 O1 2.349(4) . ? Bi1 O5 2.391(4) . ? Bi1 N3 2.425(5) . ? Bi1 O3 2.494(4) 1_655 ? Bi1 O3 2.585(4) 2_477 ? Bi1 O2 2.628(4) 1_655 ? O1 C4 1.285(7) . ? O6 C9 1.253(8) . ? O5 C9 1.276(7) . ? O2 C4 1.244(7) . ? O2 Bi1 2.628(4) 1_455 ? O3 C5 1.301(7) . ? O3 Bi1 2.494(4) 1_455 ? O3 Bi1 2.585(4) 2_477 ? O4 C5 1.231(7) . ? O7 C10 1.205(8) . ? O8 C10 1.327(8) . ? N1 C3 1.334(7) . ? N1 C1 1.368(7) . ? N3 C8 1.317(8) . ? N3 C6 1.362(8) . ? N4 C8 1.306(9) . ? N4 C7 1.377(8) . ? N2 C3 1.339(7) . ? N2 C2 1.380(7) . ? C1 C2 1.396(7) . ? C1 C4 1.486(7) . ? C2 C5 1.465(8) . ? C6 C7 1.378(8) . ? C6 C9 1.478(8) . ? C7 C10 1.470(9) . ? 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 O1 68.39(15) . . ? N1 Bi1 O5 76.66(15) . . ? O1 Bi1 O5 118.18(15) . . ? N1 Bi1 N3 110.02(19) . . ? O1 Bi1 N3 78.58(17) . . ? O5 Bi1 N3 67.62(15) . . ? N1 Bi1 O3 75.44(15) . 1_655 ? O1 Bi1 O3 135.19(13) . 1_655 ? O5 Bi1 O3 76.20(14) . 1_655 ? N3 Bi1 O3 140.34(16) . 1_655 ? N1 Bi1 O3 79.83(15) . 2_477 ? O1 Bi1 O3 77.76(14) . 2_477 ? O5 Bi1 O3 143.01(12) . 2_477 ? N3 Bi1 O3 148.53(15) . 2_477 ? O3 Bi1 O3 70.46(14) 1_655 2_477 ? N1 Bi1 O2 144.62(14) . 1_655 ? O1 Bi1 O2 146.84(12) . 1_655 ? O5 Bi1 O2 82.78(15) . 1_655 ? N3 Bi1 O2 87.64(18) . 1_655 ? O3 Bi1 O2 71.84(12) 1_655 1_655 ? O3 Bi1 O2 101.21(14) 2_477 1_655 ? C4 O1 Bi1 122.0(3) . . ? C9 O5 Bi1 121.9(4) . . ? C4 O2 Bi1 147.7(4) . 1_455 ? C5 O3 Bi1 133.4(3) . 1_455 ? C5 O3 Bi1 117.0(3) . 2_477 ? Bi1 O3 Bi1 109.54(14) 1_455 2_477 ? C3 N1 C1 107.7(5) . . ? C3 N1 Bi1 133.4(4) . . ? C1 N1 Bi1 118.2(3) . . ? C8 N3 C6 105.3(5) . . ? C8 N3 Bi1 137.8(5) . . ? C6 N3 Bi1 115.5(4) . . ? C8 N4 C7 108.7(5) . . ? C3 N2 C2 109.0(5) . . ? N1 C1 C2 108.4(5) . . ? N1 C1 C4 116.4(5) . . ? C2 C1 C4 135.2(5) . . ? N2 C2 C1 105.1(5) . . ? N2 C2 C5 117.8(5) . . ? C1 C2 C5 136.7(5) . . ? N1 C3 N2 109.8(5) . . ? O2 C4 O1 122.9(5) . . ? O2 C4 C1 122.8(5) . . ? O1 C4 C1 114.2(5) . . ? O4 C5 O3 123.9(5) . . ? O4 C5 C2 118.3(5) . . ? O3 C5 C2 117.8(5) . . ? N3 C6 C7 110.0(5) . . ? N3 C6 C9 118.4(5) . . ? C7 C6 C9 131.6(6) . . ? N4 C7 C6 103.9(5) . . ? N4 C7 C10 120.3(6) . . ? C6 C7 C10 135.7(6) . . ? N4 C8 N3 112.1(6) . . ? O6 C9 O5 125.1(5) . . ? O6 C9 C6 119.3(5) . . ? O5 C9 C6 115.6(5) . . ? O7 C10 O8 122.6(7) . . ? O7 C10 C7 120.3(6) . . ? O8 C10 C7 117.1(6) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.356 _refine_diff_density_min -1.345 _refine_diff_density_rms 0.200 ######END####### data_CompoundIII _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Bi-3,4-pyridine dicarboxylate' _chemical_melting_point ? _chemical_formula_moiety 'C7 H3 Bi N O5' _chemical_formula_sum 'C7 H3 Bi N O5' _chemical_formula_weight 390.08 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 'Triclinic' _symmetry_space_group_name_H-M 'P-1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2623(13) _cell_length_b 7.5389(12) _cell_length_c 8.1125(14) _cell_angle_alpha 97.699(6) _cell_angle_beta 101.048(6) _cell_angle_gamma 113.210(5) _cell_volume 389.69(12) _cell_formula_units_Z 2 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used 1359 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 24.98 _exptl_crystal_description 'block' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 350 _exptl_absorpt_coefficient_mu 22.615 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.0930 _exptl_absorpt_correction_T_max 0.4649 _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction,2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 300(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Xcalibur,Eos(Nova) CCD detector' _diffrn_measurement_method 'f\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5131 _diffrn_reflns_av_R_equivalents 0.0743 _diffrn_reflns_av_sigmaI/netI 0.0679 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 24.98 _reflns_number_total 1359 _reflns_number_gt 1217 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro CCD (Oxford Diffraction, 2009)' _computing_cell_refinement 'CrysAlisPro CCD (Oxford Diffraction, 2009)' _computing_data_reduction 'CrysAlisPro RED (Oxford Diffraction, 2009)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^+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 1359 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0408 _refine_ls_R_factor_gt 0.0359 _refine_ls_wR_factor_ref 0.0787 _refine_ls_wR_factor_gt 0.0776 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 0.35821(6) 0.24047(5) 0.02436(5) 0.01382(16) Uani 1 1 d . . . O1 O 0.4055(11) 0.5472(10) 0.1005(9) 0.0144(16) Uani 1 1 d . . . O2 O 0.6773(11) 0.3266(10) 0.2127(9) 0.0176(16) Uani 1 1 d . . . O3 O 0.3097(13) 0.2584(12) 0.3070(11) 0.030(2) Uani 1 1 d . . . O4 O 0.4527(12) 0.0001(11) -0.1972(10) 0.0213(17) Uani 1 1 d . . . O5 O 0.0018(13) 0.1858(12) 0.1315(10) 0.0269(19) Uani 1 1 d . . . N1 N 0.1093(15) 0.2496(14) -0.2570(12) 0.020(2) Uani 1 1 d . . . C1 C -0.1635(17) 0.2109(14) -0.5718(13) 0.013(2) Uani 1 1 d . . . C2 C -0.2216(18) 0.2141(16) -0.4168(14) 0.020(3) Uani 1 1 d . . . H2 H -0.3523 0.2064 -0.4157 0.024 Uiso 1 1 calc R . . C3 C -0.0873(17) 0.2283(16) -0.2675(14) 0.018(2) Uani 1 1 d . . . H3 H -0.1328 0.2232 -0.1678 0.021 Uiso 1 1 calc R . . C4 C 0.1666(18) 0.2497(15) -0.4043(14) 0.018(2) Uani 1 1 d . . . H4 H 0.3004 0.2631 -0.4000 0.022 Uiso 1 1 calc R . . C5 C 0.0373(17) 0.2308(14) -0.5652(13) 0.012(2) Uani 1 1 d . . . C6 C 0.6761(17) 0.1719(16) 0.2651(13) 0.014(2) Uani 1 1 d . . . C7 C 0.1147(18) 0.2239(15) 0.2789(15) 0.018(3) 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 Bi1 0.0143(3) 0.0169(2) 0.0110(3) 0.00466(18) 0.00334(19) 0.00706(19) O1 0.018(4) 0.012(4) 0.013(4) 0.003(3) 0.002(3) 0.006(4) O2 0.013(4) 0.019(4) 0.014(4) 0.004(3) -0.006(3) 0.004(4) O3 0.017(5) 0.046(5) 0.027(5) 0.014(4) 0.010(4) 0.010(5) O4 0.015(4) 0.015(4) 0.021(4) -0.002(3) -0.003(4) -0.002(4) O5 0.023(5) 0.049(5) 0.009(4) 0.003(4) -0.002(4) 0.020(5) N1 0.021(6) 0.025(5) 0.015(5) 0.005(4) 0.005(5) 0.011(5) C1 0.018(6) 0.006(5) 0.008(5) -0.004(4) -0.003(5) 0.002(5) C2 0.021(7) 0.030(6) 0.011(6) 0.002(5) 0.004(5) 0.013(6) C3 0.018(6) 0.028(6) 0.006(5) 0.001(5) 0.003(5) 0.011(6) C4 0.016(6) 0.024(6) 0.012(6) 0.006(5) -0.001(5) 0.008(6) C5 0.015(6) 0.008(5) 0.006(5) -0.002(4) 0.001(5) 0.000(5) C6 0.016(6) 0.024(6) 0.009(5) 0.006(5) 0.008(5) 0.012(6) C7 0.020(7) 0.012(5) 0.019(7) 0.004(5) 0.008(6) 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 O1 2.181(6) . ? Bi1 O2 2.306(7) . ? Bi1 O1 2.338(7) 2_665 ? Bi1 O3 2.380(8) . ? Bi1 N1 2.653(9) . ? Bi1 O4 2.751(7) . ? O1 Bi1 2.338(7) 2_665 ? O2 C6 1.292(12) . ? O3 C7 1.302(13) . ? O4 C6 1.231(13) 2_655 ? O5 C7 1.237(14) . ? N1 C4 1.339(13) . ? N1 C3 1.357(14) . ? C1 C5 1.396(14) . ? C1 C2 1.401(15) . ? C1 C6 1.493(15) 1_454 ? C2 C3 1.363(16) . ? C4 C5 1.407(15) . ? C5 C7 1.482(14) 1_554 ? C6 O4 1.231(13) 2_655 ? C6 C1 1.493(15) 1_656 ? C7 C5 1.482(14) 1_556 ? 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 Bi1 O2 88.4(2) . . ? O1 Bi1 O1 67.8(3) . 2_665 ? O2 Bi1 O1 76.3(2) . 2_665 ? O1 Bi1 O3 78.0(3) . . ? O2 Bi1 O3 73.1(3) . . ? O1 Bi1 O3 134.1(3) 2_665 . ? O1 Bi1 N1 81.7(3) . . ? O2 Bi1 N1 154.1(3) . . ? O1 Bi1 N1 77.8(3) 2_665 . ? O3 Bi1 N1 127.2(3) . . ? O1 Bi1 O4 141.6(2) . . ? O2 Bi1 O4 87.5(2) . . ? O1 Bi1 O4 74.2(2) 2_665 . ? O3 Bi1 O4 136.3(2) . . ? N1 Bi1 O4 85.5(2) . . ? Bi1 O1 Bi1 112.2(3) . 2_665 ? C6 O2 Bi1 108.7(7) . . ? C7 O3 Bi1 102.5(7) . . ? C6 O4 Bi1 119.8(6) 2_655 . ? C4 N1 C3 116.5(10) . . ? C4 N1 Bi1 119.4(7) . . ? C3 N1 Bi1 123.5(7) . . ? C5 C1 C2 117.6(10) . . ? C5 C1 C6 124.0(9) . 1_454 ? C2 C1 C6 118.3(9) . 1_454 ? C3 C2 C1 120.3(10) . . ? N1 C3 C2 123.3(10) . . ? N1 C4 C5 124.2(10) . . ? C1 C5 C4 118.0(9) . . ? C1 C5 C7 122.6(10) . 1_554 ? C4 C5 C7 119.4(10) . 1_554 ? O4 C6 O2 125.1(10) 2_655 . ? O4 C6 C1 118.8(9) 2_655 1_656 ? O2 C6 C1 116.0(9) . 1_656 ? O5 C7 O3 122.0(10) . . ? O5 C7 C5 122.6(10) . 1_556 ? O3 C7 C5 115.4(10) . 1_556 ? 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 O2 Bi1 O1 Bi1 75.9(3) . . . 2_665 ? O1 Bi1 O1 Bi1 0.0 2_665 . . 2_665 ? O3 Bi1 O1 Bi1 148.9(4) . . . 2_665 ? N1 Bi1 O1 Bi1 -80.1(3) . . . 2_665 ? O4 Bi1 O1 Bi1 -8.2(6) . . . 2_665 ? O1 Bi1 O2 C6 152.2(6) . . . . ? O1 Bi1 O2 C6 -140.3(6) 2_665 . . . ? O3 Bi1 O2 C6 74.3(6) . . . . ? N1 Bi1 O2 C6 -140.6(7) . . . . ? O4 Bi1 O2 C6 -66.0(6) . . . . ? O1 Bi1 O3 C7 84.8(7) . . . . ? O2 Bi1 O3 C7 176.9(7) . . . . ? O1 Bi1 O3 C7 126.6(6) 2_665 . . . ? N1 Bi1 O3 C7 15.1(8) . . . . ? O4 Bi1 O3 C7 -115.7(6) . . . . ? O1 Bi1 O4 C6 -143.3(7) . . . 2_655 ? O2 Bi1 O4 C6 132.3(8) . . . 2_655 ? O1 Bi1 O4 C6 -151.2(8) 2_665 . . 2_655 ? O3 Bi1 O4 C6 70.1(8) . . . 2_655 ? N1 Bi1 O4 C6 -72.6(8) . . . 2_655 ? O1 Bi1 N1 C4 108.0(8) . . . . ? O2 Bi1 N1 C4 39.4(11) . . . . ? O1 Bi1 N1 C4 39.1(8) 2_665 . . . ? O3 Bi1 N1 C4 176.0(7) . . . . ? O4 Bi1 N1 C4 -35.6(8) . . . . ? O1 Bi1 N1 C3 -80.8(8) . . . . ? O2 Bi1 N1 C3 -149.5(8) . . . . ? O1 Bi1 N1 C3 -149.8(9) 2_665 . . . ? O3 Bi1 N1 C3 -12.8(10) . . . . ? O4 Bi1 N1 C3 135.5(8) . . . . ? C5 C1 C2 C3 -2.5(16) . . . . ? C6 C1 C2 C3 173.1(9) 1_454 . . . ? C4 N1 C3 C2 -2.1(16) . . . . ? Bi1 N1 C3 C2 -173.5(8) . . . . ? C1 C2 C3 N1 3.3(17) . . . . ? C3 N1 C4 C5 0.5(16) . . . . ? Bi1 N1 C4 C5 172.2(8) . . . . ? C2 C1 C5 C4 0.9(14) . . . . ? C6 C1 C5 C4 -174.5(9) 1_454 . . . ? C2 C1 C5 C7 178.2(9) . . . 1_554 ? C6 C1 C5 C7 2.8(15) 1_454 . . 1_554 ? N1 C4 C5 C1 0.1(16) . . . . ? N1 C4 C5 C7 -177.3(9) . . . 1_554 ? Bi1 O2 C6 O4 15.4(12) . . . 2_655 ? Bi1 O2 C6 C1 -160.2(6) . . . 1_656 ? Bi1 O3 C7 O5 2.4(12) . . . . ? Bi1 O3 C7 C5 -178.4(7) . . . 1_556 ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.794 _refine_diff_density_min -1.979 _refine_diff_density_rms 0.360