# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Alagarsamy, Thirumurugan' _publ_contact_author_email akc30@cam.ac.uk _publ_section_title ; Bismuth 2,6-pyridinedicarboxylates: Assembly of molecular units into coordination polymers, CO2 sorption and photoluminescence ; loop_ _publ_author_name T.Alagarsamy 'Wei Li.' T.Cheetham # Attachment '- CIF1-6.txt' data_compound1 _database_code_depnum_ccdc_archive 'CCDC 851703' #TrackingRef '- CIF1-6.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H33 Bi N6 O12' _chemical_formula_weight 842.57 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' Bi Bi -4.1077 10.2566 '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' _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 11.8847(3) _cell_length_b 12.1913(2) _cell_length_c 12.2022(3) _cell_angle_alpha 77.2970(1) _cell_angle_beta 69.2800(1) _cell_angle_gamma 70.9250(1) _cell_volume 1551.92(6) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 17434 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.803 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 5.753 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5841 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Roper CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26435 _diffrn_reflns_av_R_equivalents 0.0469 _diffrn_reflns_av_sigmaI/netI 0.0424 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 27.49 _reflns_number_total 7103 _reflns_number_gt 6561 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0169P)^2^+3.0811P] 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 7103 _refine_ls_number_parameters 439 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0311 _refine_ls_R_factor_gt 0.0267 _refine_ls_wR_factor_ref 0.0555 _refine_ls_wR_factor_gt 0.0540 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 C1 C 0.9751(3) 0.2340(3) 0.8477(3) 0.0127(7) Uani 1 1 d . . . C2 C 0.9572(3) 0.3591(3) 0.8646(3) 0.0110(7) Uani 1 1 d . . . C3 C 0.8410(3) 0.4380(3) 0.9005(3) 0.0163(7) Uani 1 1 d . . . H3 H 0.7683 0.4150 0.9198 0.020 Uiso 1 1 calc R . . C4 C 0.8349(4) 0.5515(3) 0.9073(3) 0.0194(8) Uani 1 1 d . . . H4 H 0.7578 0.6062 0.9306 0.023 Uiso 1 1 calc R . . C5 C 0.9444(3) 0.5833(3) 0.8793(3) 0.0155(7) Uani 1 1 d . . . H5 H 0.9420 0.6595 0.8827 0.019 Uiso 1 1 calc R . . C6 C 1.0578(3) 0.4990(3) 0.8459(3) 0.0121(7) Uani 1 1 d . . . C7 C 1.1831(3) 0.5220(3) 0.8160(3) 0.0140(7) Uani 1 1 d . . . C11 C 1.2392(3) 0.3345(3) 0.4796(3) 0.0167(7) Uani 1 1 d . . . C12 C 1.2778(3) 0.2025(3) 0.4863(3) 0.0132(7) Uani 1 1 d . . . C13 C 1.2831(3) 0.1468(3) 0.3955(3) 0.0171(8) Uani 1 1 d . . . H13 H 1.2632 0.1901 0.3287 0.021 Uiso 1 1 calc R . . C14 C 1.3185(4) 0.0256(3) 0.4069(3) 0.0185(8) Uani 1 1 d . . . H14 H 1.3219 -0.0135 0.3480 0.022 Uiso 1 1 calc R . . C15 C 1.3488(3) -0.0363(3) 0.5066(3) 0.0156(7) Uani 1 1 d . . . H15 H 1.3729 -0.1176 0.5157 0.019 Uiso 1 1 calc R . . C16 C 1.3424(3) 0.0256(3) 0.5938(3) 0.0120(7) Uani 1 1 d . . . C17 C 1.3746(3) -0.0341(3) 0.7055(3) 0.0133(7) Uani 1 1 d . . . C21 C 1.2687(3) 0.1517(3) 1.0394(3) 0.0122(7) Uani 1 1 d . . . C22 C 1.4004(3) 0.1652(3) 0.9832(3) 0.0127(7) Uani 1 1 d . . . C23 C 1.4838(3) 0.1447(3) 1.0468(3) 0.0153(7) Uani 1 1 d . . . H23 H 1.4614 0.1199 1.1273 0.018 Uiso 1 1 calc R . . C24 C 1.6010(3) 0.1623(3) 0.9870(3) 0.0189(8) Uani 1 1 d . . . H24 H 1.6582 0.1508 1.0272 0.023 Uiso 1 1 calc R . . C25 C 1.6318(3) 0.1970(3) 0.8667(3) 0.0157(7) Uani 1 1 d . . . H25 H 1.7098 0.2094 0.8251 0.019 Uiso 1 1 calc R . . C26 C 1.5449(3) 0.2132(3) 0.8086(3) 0.0125(7) Uani 1 1 d . . . C27 C 1.5712(3) 0.2485(3) 0.6764(3) 0.0123(7) Uani 1 1 d . . . C31 C 0.4925(4) 0.5625(4) 0.8179(4) 0.0320(10) Uani 1 1 d . . . H31A H 0.4556 0.6012 0.8880 0.048 Uiso 1 1 calc R . . H31B H 0.5794 0.5605 0.7860 0.048 Uiso 1 1 calc R . . H31C H 0.4846 0.4842 0.8370 0.048 Uiso 1 1 calc R . . C32 C 0.4792(4) 0.5728(3) 0.6179(3) 0.0262(9) Uani 1 1 d . . . H32A H 0.4336 0.6177 0.5643 0.039 Uiso 1 1 calc R . . H32B H 0.4716 0.4944 0.6343 0.039 Uiso 1 1 calc R . . H32C H 0.5658 0.5713 0.5830 0.039 Uiso 1 1 calc R . . C33 C 1.0518(4) 0.6871(3) 0.5879(3) 0.0254(9) Uani 1 1 d . . . H33A H 1.0875 0.6748 0.6503 0.038 Uiso 1 1 calc R . . H33B H 0.9789 0.6587 0.6164 0.038 Uiso 1 1 calc R . . H33C H 1.0288 0.7691 0.5611 0.038 Uiso 1 1 calc R . . C34 C 1.0938(4) 0.6400(3) 0.3900(3) 0.0259(9) Uani 1 1 d . . . H34A H 1.1557 0.5979 0.3270 0.039 Uiso 1 1 calc R . . H34B H 1.0711 0.7217 0.3620 0.039 Uiso 1 1 calc R . . H34C H 1.0211 0.6113 0.4171 0.039 Uiso 1 1 calc R . . C35 C 0.9964(5) -0.0023(4) 1.3212(3) 0.0355(11) Uani 1 1 d . . . H35A H 1.0644 -0.0499 1.3502 0.053 Uiso 1 1 calc R . . H35B H 0.9324 -0.0420 1.3439 0.053 Uiso 1 1 calc R . . H35C H 0.9625 0.0708 1.3538 0.053 Uiso 1 1 calc R . . C36 C 0.9440(4) 0.0928(3) 1.1372(5) 0.0338(11) Uani 1 1 d . . . H36A H 0.9803 0.1037 1.0531 0.051 Uiso 1 1 calc R . . H36B H 0.9091 0.1675 1.1667 0.051 Uiso 1 1 calc R . . H36C H 0.8793 0.0546 1.1566 0.051 Uiso 1 1 calc R . . Bi1 Bi 1.274775(11) 0.238944(10) 0.761245(10) 0.00809(4) Uani 1 1 d . . . N1 N 1.0632(3) 0.3894(2) 0.8382(2) 0.0109(6) Uani 1 1 d . . . N2 N 1.3070(3) 0.1422(2) 0.5823(2) 0.0107(6) Uani 1 1 d . . . N3 N 1.4312(3) 0.1983(2) 0.8673(2) 0.0101(6) Uani 1 1 d . . . N4 N 0.4277(3) 0.6269(3) 0.7297(3) 0.0183(7) Uani 1 1 d . . . N5 N 1.1451(3) 0.6231(3) 0.4883(3) 0.0154(6) Uani 1 1 d . . . N6 N 1.0421(3) 0.0197(3) 1.1918(3) 0.0186(7) Uani 1 1 d . . . O1 O 1.2787(2) 0.4358(2) 0.8015(2) 0.0151(5) Uani 1 1 d . . . O2 O 1.1837(2) 0.6268(2) 0.8069(2) 0.0198(6) Uani 1 1 d . . . O3 O 1.0842(2) 0.1763(2) 0.7956(2) 0.0140(5) Uani 1 1 d . . . O4 O 0.8799(2) 0.1981(2) 0.8828(2) 0.0177(5) Uani 1 1 d . . . O5 O 1.3615(2) 0.0324(2) 0.7790(2) 0.0147(5) Uani 1 1 d . . . O6 O 1.4104(3) -0.1422(2) 0.7199(2) 0.0219(6) Uani 1 1 d . . . O7 O 1.2202(2) 0.3787(2) 0.5724(2) 0.0168(5) Uani 1 1 d . . . O8 O 1.2284(3) 0.3909(2) 0.3849(2) 0.0292(7) Uani 1 1 d . . . O9 O 1.1997(2) 0.1801(2) 0.9737(2) 0.0132(5) Uani 1 1 d . . . O10 O 1.2365(2) 0.1154(2) 1.1472(2) 0.0169(5) Uani 1 1 d . . . O11 O 1.4848(2) 0.2584(2) 0.6347(2) 0.0137(5) Uani 1 1 d . . . O12 O 1.6772(2) 0.2616(2) 0.6188(2) 0.0203(6) Uani 1 1 d . . . H41 H 0.332(5) 0.619(4) 0.771(4) 0.054(16) Uiso 1 1 d . . . H42 H 0.431(5) 0.703(4) 0.719(4) 0.040(14) Uiso 1 1 d . . . H51 H 1.173(4) 0.545(3) 0.512(3) 0.012(9) Uiso 1 1 d . . . H52 H 1.229(6) 0.656(5) 0.452(5) 0.08(2) Uiso 1 1 d . . . H61 H 1.076(4) -0.056(4) 1.160(4) 0.031(12) Uiso 1 1 d . . . H62 H 1.111(5) 0.057(4) 1.172(4) 0.039(13) 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 C1 0.0130(17) 0.0161(17) 0.0111(16) 0.0009(13) -0.0069(13) -0.0045(14) C2 0.0139(17) 0.0125(16) 0.0067(15) 0.0018(13) -0.0038(13) -0.0049(13) C3 0.0107(17) 0.0221(19) 0.0155(17) -0.0031(15) -0.0027(14) -0.0046(15) C4 0.0150(19) 0.0198(19) 0.0182(18) -0.0065(15) -0.0013(15) 0.0006(15) C5 0.0173(19) 0.0106(16) 0.0158(17) -0.0056(14) -0.0039(14) 0.0011(14) C6 0.0146(18) 0.0128(16) 0.0084(15) -0.0010(13) -0.0034(13) -0.0035(14) C7 0.0175(18) 0.0113(16) 0.0140(17) -0.0016(14) -0.0064(14) -0.0029(14) C11 0.0146(18) 0.0170(18) 0.0199(19) -0.0010(15) -0.0091(15) -0.0028(14) C12 0.0093(17) 0.0159(17) 0.0132(17) -0.0007(14) -0.0041(13) -0.0017(14) C13 0.0197(19) 0.0205(18) 0.0142(17) -0.0044(15) -0.0079(15) -0.0051(15) C14 0.022(2) 0.0219(19) 0.0144(18) -0.0097(15) -0.0069(15) -0.0034(16) C15 0.0164(19) 0.0143(17) 0.0182(18) -0.0070(14) -0.0054(15) -0.0035(14) C16 0.0102(17) 0.0108(16) 0.0155(17) -0.0041(13) -0.0043(13) -0.0015(13) C17 0.0106(17) 0.0116(16) 0.0183(18) -0.0023(14) -0.0056(14) -0.0024(13) C21 0.0124(17) 0.0066(15) 0.0166(17) -0.0021(13) -0.0033(14) -0.0021(13) C22 0.0148(18) 0.0058(15) 0.0165(17) -0.0006(13) -0.0040(14) -0.0028(13) C23 0.0174(19) 0.0164(17) 0.0140(17) 0.0006(14) -0.0072(14) -0.0061(15) C24 0.0161(19) 0.026(2) 0.0199(19) -0.0006(16) -0.0115(15) -0.0078(16) C25 0.0102(17) 0.0194(18) 0.0211(19) -0.0045(15) -0.0069(14) -0.0049(14) C26 0.0090(17) 0.0104(16) 0.0169(17) -0.0038(14) -0.0036(13) -0.0002(13) C27 0.0134(18) 0.0067(15) 0.0157(17) -0.0026(13) -0.0014(14) -0.0039(13) C31 0.030(2) 0.034(2) 0.035(2) -0.002(2) -0.015(2) -0.008(2) C32 0.031(2) 0.024(2) 0.023(2) -0.0045(17) -0.0031(18) -0.0119(18) C33 0.026(2) 0.024(2) 0.022(2) -0.0043(17) -0.0070(17) -0.0011(17) C34 0.034(2) 0.025(2) 0.022(2) -0.0004(17) -0.0194(18) -0.0022(18) C35 0.055(3) 0.043(3) 0.016(2) -0.0054(19) 0.002(2) -0.035(2) C36 0.025(2) 0.0161(19) 0.062(3) 0.003(2) -0.019(2) -0.0049(17) Bi1 0.00771(6) 0.00741(6) 0.00980(6) -0.00164(4) -0.00356(4) -0.00155(4) N1 0.0129(15) 0.0132(14) 0.0069(13) 0.0001(11) -0.0028(11) -0.0052(12) N2 0.0083(14) 0.0097(13) 0.0136(14) -0.0013(11) -0.0034(11) -0.0017(11) N3 0.0120(14) 0.0075(13) 0.0108(13) -0.0012(11) -0.0045(11) -0.0016(11) N4 0.0212(18) 0.0119(15) 0.0235(17) -0.0022(13) -0.0080(14) -0.0055(13) N5 0.0169(16) 0.0111(15) 0.0174(16) 0.0002(12) -0.0067(13) -0.0027(13) N6 0.0185(17) 0.0166(16) 0.0221(17) -0.0022(13) -0.0039(13) -0.0091(14) O1 0.0123(13) 0.0121(12) 0.0214(13) -0.0048(10) -0.0051(10) -0.0021(10) O2 0.0189(14) 0.0108(12) 0.0301(15) -0.0060(11) -0.0055(11) -0.0046(10) O3 0.0123(13) 0.0128(12) 0.0185(13) -0.0042(10) -0.0063(10) -0.0020(10) O4 0.0129(13) 0.0185(13) 0.0246(14) -0.0010(11) -0.0063(11) -0.0085(10) O5 0.0199(14) 0.0116(12) 0.0151(12) -0.0029(10) -0.0086(10) -0.0028(10) O6 0.0313(16) 0.0089(12) 0.0283(15) -0.0021(11) -0.0152(12) -0.0025(11) O7 0.0207(14) 0.0132(12) 0.0158(12) -0.0035(10) -0.0057(11) -0.0025(10) O8 0.050(2) 0.0183(14) 0.0213(15) 0.0041(12) -0.0196(14) -0.0074(13) O9 0.0114(12) 0.0176(12) 0.0126(12) -0.0015(10) -0.0048(10) -0.0056(10) O10 0.0186(14) 0.0238(13) 0.0109(12) 0.0018(10) -0.0044(10) -0.0118(11) O11 0.0137(13) 0.0148(12) 0.0124(12) -0.0033(10) -0.0040(10) -0.0022(10) O12 0.0134(13) 0.0272(14) 0.0193(13) -0.0004(11) 0.0006(11) -0.0119(11) _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 C1 O4 1.247(4) . ? C1 O3 1.264(4) . ? C1 C2 1.519(5) . ? C2 N1 1.338(4) . ? C2 C3 1.384(5) . ? C3 C4 1.382(5) . ? C3 H3 0.9300 . ? C4 C5 1.384(5) . ? C4 H4 0.9300 . ? C5 C6 1.389(5) . ? C5 H5 0.9300 . ? C6 N1 1.340(4) . ? C6 C7 1.507(5) . ? C7 O1 1.260(4) . ? C7 O2 1.260(4) . ? C11 O8 1.234(4) . ? C11 O7 1.276(4) . ? C11 C12 1.515(5) . ? C12 N2 1.332(4) . ? C12 C13 1.395(5) . ? C13 C14 1.387(5) . ? C13 H13 0.9300 . ? C14 C15 1.381(5) . ? C14 H14 0.9300 . ? C15 C16 1.402(5) . ? C15 H15 0.9300 . ? C16 N2 1.334(4) . ? C16 C17 1.511(5) . ? C17 O6 1.239(4) . ? C17 O5 1.275(4) . ? C21 O10 1.252(4) . ? C21 O9 1.263(4) . ? C21 C22 1.518(5) . ? C22 N3 1.333(4) . ? C22 C23 1.394(5) . ? C23 C24 1.388(5) . ? C23 H23 0.9300 . ? C24 C25 1.385(5) . ? C24 H24 0.9300 . ? C25 C26 1.389(5) . ? C25 H25 0.9300 . ? C26 N3 1.338(4) . ? C26 C27 1.520(5) . ? C27 O12 1.249(4) . ? C27 O11 1.261(4) . ? C31 N4 1.479(5) . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C32 N4 1.488(5) . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 N5 1.488(5) . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? C34 N5 1.476(5) . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C35 N6 1.470(5) . ? C35 H35A 0.9600 . ? C35 H35B 0.9600 . ? C35 H35C 0.9600 . ? C36 N6 1.485(5) . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? Bi1 O5 2.381(2) . ? Bi1 O9 2.449(2) . ? Bi1 O11 2.484(2) . ? Bi1 N3 2.489(3) . ? Bi1 O3 2.492(2) . ? Bi1 N2 2.560(3) . ? Bi1 O1 2.571(2) . ? Bi1 N1 2.577(3) . ? Bi1 O7 2.691(2) . ? N4 H41 1.10(5) . ? N4 H42 0.92(5) . ? N5 H51 0.91(4) . ? N5 H52 1.11(6) . ? N6 H61 0.98(4) . ? N6 H62 1.00(5) . ? 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 O4 C1 O3 125.3(3) . . ? O4 C1 C2 117.1(3) . . ? O3 C1 C2 117.6(3) . . ? N1 C2 C3 121.9(3) . . ? N1 C2 C1 114.9(3) . . ? C3 C2 C1 123.3(3) . . ? C4 C3 C2 118.7(3) . . ? C4 C3 H3 120.6 . . ? C2 C3 H3 120.6 . . ? C3 C4 C5 119.6(3) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C4 C5 C6 118.6(3) . . ? C4 C5 H5 120.7 . . ? C6 C5 H5 120.7 . . ? N1 C6 C5 121.6(3) . . ? N1 C6 C7 114.7(3) . . ? C5 C6 C7 123.7(3) . . ? O1 C7 O2 125.1(3) . . ? O1 C7 C6 117.9(3) . . ? O2 C7 C6 117.0(3) . . ? O8 C11 O7 125.2(3) . . ? O8 C11 C12 117.4(3) . . ? O7 C11 C12 117.5(3) . . ? N2 C12 C13 121.6(3) . . ? N2 C12 C11 117.1(3) . . ? C13 C12 C11 121.3(3) . . ? C14 C13 C12 118.6(3) . . ? C14 C13 H13 120.7 . . ? C12 C13 H13 120.7 . . ? C15 C14 C13 119.4(3) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C14 C15 C16 118.8(3) . . ? C14 C15 H15 120.6 . . ? C16 C15 H15 120.6 . . ? N2 C16 C15 121.2(3) . . ? N2 C16 C17 116.0(3) . . ? C15 C16 C17 122.8(3) . . ? O6 C17 O5 124.8(3) . . ? O6 C17 C16 118.8(3) . . ? O5 C17 C16 116.4(3) . . ? O10 C21 O9 125.2(3) . . ? O10 C21 C22 117.8(3) . . ? O9 C21 C22 117.0(3) . . ? N3 C22 C23 121.9(3) . . ? N3 C22 C21 114.9(3) . . ? C23 C22 C21 123.2(3) . . ? C24 C23 C22 118.4(3) . . ? C24 C23 H23 120.8 . . ? C22 C23 H23 120.8 . . ? C25 C24 C23 119.1(3) . . ? C25 C24 H24 120.5 . . ? C23 C24 H24 120.5 . . ? C24 C25 C26 119.3(3) . . ? C24 C25 H25 120.3 . . ? C26 C25 H25 120.3 . . ? N3 C26 C25 121.2(3) . . ? N3 C26 C27 115.7(3) . . ? C25 C26 C27 123.1(3) . . ? O12 C27 O11 126.1(3) . . ? O12 C27 C26 117.3(3) . . ? O11 C27 C26 116.6(3) . . ? N4 C31 H31A 109.5 . . ? N4 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? N4 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? N4 C32 H32A 109.5 . . ? N4 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? N4 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? N5 C33 H33A 109.5 . . ? N5 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? N5 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? N5 C34 H34A 109.5 . . ? N5 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? N5 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? N6 C35 H35A 109.5 . . ? N6 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? N6 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? N6 C36 H36A 109.5 . . ? N6 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? N6 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? O5 Bi1 O9 76.64(8) . . ? O5 Bi1 O11 88.43(8) . . ? O9 Bi1 O11 129.87(8) . . ? O5 Bi1 N3 74.11(8) . . ? O9 Bi1 N3 65.05(8) . . ? O11 Bi1 N3 64.85(8) . . ? O5 Bi1 O3 80.33(8) . . ? O9 Bi1 O3 73.84(8) . . ? O11 Bi1 O3 150.61(8) . . ? N3 Bi1 O3 135.34(8) . . ? O5 Bi1 N2 65.11(8) . . ? O9 Bi1 N2 131.94(8) . . ? O11 Bi1 N2 78.55(8) . . ? N3 Bi1 N2 125.14(9) . . ? O3 Bi1 N2 72.08(8) . . ? O5 Bi1 O1 146.27(8) . . ? O9 Bi1 O1 90.20(8) . . ? O11 Bi1 O1 76.33(7) . . ? N3 Bi1 O1 72.18(8) . . ? O3 Bi1 O1 126.06(7) . . ? N2 Bi1 O1 137.52(8) . . ? O5 Bi1 N1 138.60(9) . . ? O9 Bi1 N1 74.27(8) . . ? O11 Bi1 N1 132.94(8) . . ? N3 Bi1 N1 117.50(8) . . ? O3 Bi1 N1 63.71(8) . . ? N2 Bi1 N1 117.36(9) . . ? O1 Bi1 N1 62.37(8) . . ? O5 Bi1 O7 127.28(7) . . ? O9 Bi1 O7 146.52(8) . . ? O11 Bi1 O7 78.75(8) . . ? N3 Bi1 O7 137.90(8) . . ? O3 Bi1 O7 86.61(8) . . ? N2 Bi1 O7 62.26(8) . . ? O1 Bi1 O7 79.52(7) . . ? N1 Bi1 O7 72.73(8) . . ? C2 N1 C6 119.6(3) . . ? C2 N1 Bi1 119.4(2) . . ? C6 N1 Bi1 120.9(2) . . ? C12 N2 C16 120.3(3) . . ? C12 N2 Bi1 122.7(2) . . ? C16 N2 Bi1 116.6(2) . . ? C22 N3 C26 120.0(3) . . ? C22 N3 Bi1 120.0(2) . . ? C26 N3 Bi1 120.0(2) . . ? C31 N4 C32 113.0(3) . . ? C31 N4 H41 104(3) . . ? C32 N4 H41 107(3) . . ? C31 N4 H42 107(3) . . ? C32 N4 H42 113(3) . . ? H41 N4 H42 112(4) . . ? C34 N5 C33 111.2(3) . . ? C34 N5 H51 110(2) . . ? C33 N5 H51 112(2) . . ? C34 N5 H52 107(3) . . ? C33 N5 H52 111(3) . . ? H51 N5 H52 106(4) . . ? C35 N6 C36 114.0(4) . . ? C35 N6 H61 108(3) . . ? C36 N6 H61 108(3) . . ? C35 N6 H62 107(3) . . ? C36 N6 H62 111(3) . . ? H61 N6 H62 109(4) . . ? C7 O1 Bi1 121.5(2) . . ? C1 O3 Bi1 123.2(2) . . ? C17 O5 Bi1 125.2(2) . . ? C11 O7 Bi1 119.8(2) . . ? C21 O9 Bi1 122.9(2) . . ? C27 O11 Bi1 122.6(2) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.736 _refine_diff_density_min -1.396 _refine_diff_density_rms 0.137 #===END data_compound2 _database_code_depnum_ccdc_archive 'CCDC 851704' #TrackingRef '- CIF1-6.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H37 Bi N6 O14' _chemical_formula_weight 878.61 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Bi Bi -4.0111 8.9310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 16.7930(3) _cell_length_b 10.5974(2) _cell_length_c 18.5857(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3307.55(11) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.764 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1744 _exptl_absorpt_coefficient_mu 11.132 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.348 _exptl_absorpt_correction_T_max 0.515 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1183 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22185 _diffrn_reflns_av_R_equivalents 0.0324 _diffrn_reflns_av_sigmaI/netI 0.0170 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 4.76 _diffrn_reflns_theta_max 71.19 _reflns_number_total 3193 _reflns_number_gt 2577 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; DFIX N3 H3a 0.95 0.01 DFIX N3 H3b 0.95 0.01 DFIX N4 C32 1.485 0.01 DFIX N4 C31 1.485 0.01 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^)+(0.0304P)^2^+18.1416P] 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 3193 _refine_ls_number_parameters 246 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0478 _refine_ls_R_factor_gt 0.0377 _refine_ls_wR_factor_ref 0.0943 _refine_ls_wR_factor_gt 0.0888 _refine_ls_goodness_of_fit_ref 1.206 _refine_ls_restrained_S_all 1.206 _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 C1 C 0.1593(4) 0.6183(5) 0.1396(4) 0.0382(15) Uani 1 1 d . . . C2 C 0.1827(4) 0.7212(6) 0.1911(4) 0.0381(15) Uani 1 1 d . . . C3 C 0.2545(4) 0.7874(7) 0.1859(4) 0.0447(18) Uani 1 1 d . . . C4 C 0.2710(4) 0.8823(7) 0.2359(3) 0.0442(19) Uani 1 1 d . . . H4 H 0.3186 0.9270 0.2338 0.053 Uiso 1 1 calc R . . C5 C 0.2163(4) 0.9082(7) 0.2875(4) 0.0481(19) Uani 1 1 d . . . H5 H 0.2258 0.9720 0.3208 0.058 Uiso 1 1 calc R . . C6 C 0.1460(4) 0.8392(6) 0.2905(4) 0.0365(15) Uani 1 1 d . . . C7 C 0.0832(4) 0.8595(5) 0.3477(4) 0.0363(15) Uani 1 1 d . . . C11 C 0.0857(3) 0.4058(5) 0.3534(3) 0.0302(13) Uani 1 1 d . . . C12 C 0.0405(3) 0.3240(5) 0.3004(3) 0.0241(11) Uani 1 1 d . . . C13 C 0.0424(4) 0.1946(6) 0.3023(4) 0.0392(15) Uani 1 1 d . . . H13 H 0.0712 0.1522 0.3375 0.047 Uiso 1 1 calc R . . C14 C 0.0000 0.1283(8) 0.2500 0.052(3) Uani 1 2 d S . . H14 H 0.0000 0.0405 0.2500 0.062 Uiso 1 2 calc SR . . C21 C 0.0934(5) 0.3610(8) 0.0068(4) 0.059(2) Uani 1 1 d . . . H21A H 0.0653 0.3313 -0.0349 0.089 Uiso 1 1 calc R . . H21B H 0.0592 0.4151 0.0344 0.089 Uiso 1 1 calc R . . H21C H 0.1093 0.2903 0.0358 0.089 Uiso 1 1 calc R . . C22 C 0.2308(5) 0.3522(8) -0.0398(4) 0.065(3) Uani 1 1 d . . . H22A H 0.2444 0.2932 -0.0025 0.098 Uiso 1 1 calc R . . H22B H 0.2760 0.4046 -0.0501 0.098 Uiso 1 1 calc R . . H22C H 0.2157 0.3070 -0.0824 0.098 Uiso 1 1 calc R . . C31 C 0.0754(10) 0.8373(12) 0.0243(9) 0.029(4) Uiso 0.50 1 d PD A 1 H31A H 0.0558 0.8006 -0.0194 0.044 Uiso 0.50 1 calc PR A 1 H31B H 0.0631 0.7828 0.0641 0.044 Uiso 0.50 1 calc PR A 1 H31C H 0.1320 0.8480 0.0210 0.044 Uiso 0.50 1 calc PR A 1 C32 C 0.0943(7) 1.0125(13) 0.0890(7) 0.035(3) Uani 0.50 1 d PD A 1 H32A H 0.1467 1.0146 0.0685 0.053 Uiso 0.50 1 calc PR A 1 H32B H 0.0945 0.9597 0.1310 0.053 Uiso 0.50 1 calc PR A 1 H32C H 0.0786 1.0965 0.1023 0.053 Uiso 0.50 1 calc PR A 1 N1 N 0.1306(3) 0.7488(4) 0.2426(3) 0.0317(11) Uani 1 1 d . . . N2 N 0.0000 0.3864(6) 0.2500 0.0243(13) Uani 1 2 d S . . N3 N 0.1641(4) 0.4314(7) -0.0158(3) 0.0512(16) Uani 1 1 d D . . N4 N 0.0374(5) 0.9613(8) 0.0356(5) 0.029(2) Uani 0.50 1 d PD A 1 H4A H -0.0121 0.9540 0.0538 0.035 Uiso 0.50 1 calc PR A 1 H4B H 0.0361 1.0076 -0.0049 0.035 Uiso 0.50 1 calc PR A 1 O1 O 0.0933(2) 0.5649(4) 0.1502(2) 0.0351(10) Uani 1 1 d . . . O2 O 0.2084(3) 0.5913(5) 0.0912(3) 0.0498(12) Uani 1 1 d . . . O3 O 0.0197(2) 0.7959(4) 0.3408(3) 0.0471(13) Uani 1 1 d . . . O4 O 0.0983(3) 0.9367(4) 0.3961(3) 0.0433(11) Uani 1 1 d . . . O5 O 0.0900(2) 0.5230(4) 0.3389(2) 0.0348(10) Uani 1 1 d . . . O6 O 0.1167(3) 0.3525(4) 0.4060(3) 0.0430(11) Uani 1 1 d . . . Bi1A Bi 0.0000 0.62870(2) 0.2500 0.02819(11) Uani 1 2 d S . . O8 O 0.1220(6) 1.0752(11) 0.0789(6) 0.051(3) Uani 0.50 1 d P B 2 O7 O 0.0599(7) 0.8356(10) 0.0124(6) 0.036(3) Uiso 0.50 1 d P C 2 H3 H 0.279(4) 0.771(7) 0.151(4) 0.043 Uiso 1 1 d . . . H3A H 0.151(5) 0.487(6) -0.054(3) 0.06(2) Uiso 1 1 d D . . H3B H 0.178(5) 0.476(7) 0.027(3) 0.07(3) 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 C1 0.025(3) 0.025(3) 0.064(4) 0.015(3) -0.002(3) 0.008(2) C2 0.027(3) 0.027(3) 0.061(4) 0.018(3) -0.008(3) 0.002(2) C3 0.024(3) 0.052(4) 0.058(5) 0.028(4) -0.010(3) -0.007(3) C4 0.034(3) 0.053(4) 0.045(4) 0.030(3) -0.014(3) -0.029(3) C5 0.044(4) 0.044(4) 0.057(4) 0.020(3) -0.022(4) -0.023(3) C6 0.026(3) 0.022(3) 0.062(4) 0.015(3) -0.014(3) -0.006(2) C7 0.026(3) 0.017(3) 0.066(4) 0.012(3) -0.016(3) 0.000(2) C11 0.021(3) 0.030(3) 0.039(3) -0.012(3) -0.003(2) 0.003(2) C12 0.023(3) 0.022(3) 0.027(3) -0.001(2) -0.004(2) -0.001(2) C13 0.055(4) 0.025(3) 0.038(3) 0.009(3) -0.014(3) 0.001(3) C14 0.087(8) 0.016(4) 0.052(6) 0.000 -0.041(6) 0.000 C21 0.061(5) 0.070(5) 0.047(4) -0.023(4) -0.015(4) -0.008(4) C22 0.064(5) 0.082(6) 0.049(4) -0.028(4) -0.019(4) 0.027(5) C32 0.032(7) 0.037(8) 0.037(7) 0.005(6) -0.006(6) -0.009(6) N1 0.023(2) 0.020(2) 0.052(3) 0.011(2) -0.008(2) 0.0029(19) N2 0.021(3) 0.022(3) 0.031(3) 0.000 -0.002(3) 0.000 N3 0.057(4) 0.069(4) 0.027(3) 0.020(3) -0.001(3) 0.021(3) N4 0.030(5) 0.034(5) 0.024(5) 0.006(4) 0.002(4) 0.002(4) O1 0.021(2) 0.027(2) 0.057(3) 0.005(2) 0.0033(19) -0.0011(16) O2 0.031(2) 0.042(3) 0.076(4) 0.007(3) 0.014(2) -0.002(2) O3 0.025(2) 0.023(2) 0.093(4) -0.011(2) -0.004(2) -0.0037(17) O4 0.036(2) 0.024(2) 0.070(3) -0.002(2) -0.013(2) -0.0065(19) O5 0.025(2) 0.024(2) 0.055(3) -0.0142(19) -0.0023(19) 0.0002(17) O6 0.046(3) 0.038(2) 0.045(3) -0.014(2) -0.023(2) 0.008(2) Bi1A 0.01780(16) 0.01469(15) 0.0521(2) 0.000 -0.00650(14) 0.000 O8 0.039(6) 0.045(6) 0.068(7) -0.012(6) -0.010(5) -0.004(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 C1 O2 1.254(8) . ? C1 O1 1.260(7) . ? C1 C2 1.502(10) . ? C2 N1 1.329(8) . ? C2 C3 1.399(9) . ? C3 C4 1.398(11) . ? C3 H3 0.78(7) . ? C4 C5 1.356(11) . ? C4 H4 0.9300 . ? C5 C6 1.390(8) . ? C5 H5 0.9300 . ? C6 N1 1.332(8) . ? C6 C7 1.513(10) . ? C7 O4 1.242(8) . ? C7 O3 1.269(7) . ? C11 O6 1.244(7) . ? C11 O5 1.272(7) . ? C11 C12 1.516(7) . ? C12 N2 1.333(6) . ? C12 C13 1.372(8) . ? C13 C14 1.394(8) . ? C13 H13 0.9300 . ? C14 C13 1.394(8) 4 ? C14 H14 0.9300 . ? C21 N3 1.464(10) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 N3 1.470(9) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C31 N4 1.476(9) . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C32 N4 1.482(9) . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? N1 Bi1A 2.540(5) . ? N2 C12 1.333(6) 4 ? N2 Bi1A 2.568(6) . ? N3 H3A 0.950(10) . ? N3 H3B 0.950(10) . ? N4 H4A 0.9000 . ? N4 H4B 0.9000 . ? O1 Bi1A 2.521(4) . ? O3 Bi1A 2.469(5) . ? O5 Bi1A 2.504(4) . ? Bi1A O3 2.469(5) 4 ? Bi1A O5 2.504(4) 4 ? Bi1A O1 2.521(4) 4 ? Bi1A N1 2.540(5) 4 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C1 O1 126.0(7) . . ? O2 C1 C2 116.8(6) . . ? O1 C1 C2 117.2(6) . . ? N1 C2 C3 120.4(7) . . ? N1 C2 C1 116.6(5) . . ? C3 C2 C1 123.0(7) . . ? C4 C3 C2 119.1(7) . . ? C4 C3 H3 127(6) . . ? C2 C3 H3 114(6) . . ? C5 C4 C3 118.8(6) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? C4 C5 C6 119.8(7) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? N1 C6 C5 121.1(7) . . ? N1 C6 C7 115.9(5) . . ? C5 C6 C7 123.0(7) . . ? O4 C7 O3 126.5(7) . . ? O4 C7 C6 117.5(5) . . ? O3 C7 C6 116.0(6) . . ? O6 C11 O5 125.9(6) . . ? O6 C11 C12 117.4(5) . . ? O5 C11 C12 116.7(5) . . ? N2 C12 C13 121.7(5) . . ? N2 C12 C11 115.4(5) . . ? C13 C12 C11 122.9(5) . . ? C12 C13 C14 118.3(6) . . ? C12 C13 H13 120.8 . . ? C14 C13 H13 120.8 . . ? C13 C14 C13 119.4(8) . 4 ? C13 C14 H14 120.3 . . ? C13 C14 H14 120.3 4 . ? N3 C21 H21A 109.5 . . ? N3 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N3 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N3 C22 H22A 109.5 . . ? N3 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N3 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C2 N1 C6 120.8(5) . . ? C2 N1 Bi1A 119.8(4) . . ? C6 N1 Bi1A 119.4(4) . . ? C12 N2 C12 120.5(7) . 4 ? C12 N2 Bi1A 119.7(3) . . ? C12 N2 Bi1A 119.7(3) 4 . ? C21 N3 C22 114.5(7) . . ? C21 N3 H3A 110(5) . . ? C22 N3 H3A 108(5) . . ? C21 N3 H3B 102(5) . . ? C22 N3 H3B 110(5) . . ? H3A N3 H3B 112(7) . . ? C31 N4 C32 98.2(10) . . ? C31 N4 H4A 112.1 . . ? C32 N4 H4A 112.1 . . ? C31 N4 H4B 112.1 . . ? C32 N4 H4B 112.1 . . ? H4A N4 H4B 109.8 . . ? C1 O1 Bi1A 122.7(4) . . ? C7 O3 Bi1A 124.3(5) . . ? C11 O5 Bi1A 122.8(4) . . ? O3 Bi1A O3 88.3(2) . 4 ? O3 Bi1A O5 148.54(14) . 4 ? O3 Bi1A O5 77.82(14) 4 4 ? O3 Bi1A O5 77.82(14) . . ? O3 Bi1A O5 148.54(14) 4 . ? O5 Bi1A O5 126.84(17) 4 . ? O3 Bi1A O1 76.84(15) . 4 ? O3 Bi1A O1 127.77(14) 4 4 ? O5 Bi1A O1 89.48(14) 4 4 ? O5 Bi1A O1 76.65(14) . 4 ? O3 Bi1A O1 127.77(14) . . ? O3 Bi1A O1 76.84(15) 4 . ? O5 Bi1A O1 76.65(14) 4 . ? O5 Bi1A O1 89.48(14) . . ? O1 Bi1A O1 148.88(18) 4 . ? O3 Bi1A N1 64.01(16) . . ? O3 Bi1A N1 73.70(14) 4 . ? O5 Bi1A N1 135.22(15) 4 . ? O5 Bi1A N1 74.84(14) . . ? O1 Bi1A N1 135.30(16) 4 . ? O1 Bi1A N1 63.76(15) . . ? O3 Bi1A N1 73.70(14) . 4 ? O3 Bi1A N1 64.01(16) 4 4 ? O5 Bi1A N1 74.84(14) 4 4 ? O5 Bi1A N1 135.22(15) . 4 ? O1 Bi1A N1 63.76(15) 4 4 ? O1 Bi1A N1 135.30(16) . 4 ? N1 Bi1A N1 119.9(2) . 4 ? O3 Bi1A N2 135.84(12) . . ? O3 Bi1A N2 135.84(12) 4 . ? O5 Bi1A N2 63.42(9) 4 . ? O5 Bi1A N2 63.42(9) . . ? O1 Bi1A N2 74.44(9) 4 . ? O1 Bi1A N2 74.44(9) . . ? N1 Bi1A N2 120.07(10) . . ? N1 Bi1A N2 120.07(10) 4 . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 71.19 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.914 _refine_diff_density_min -2.021 _refine_diff_density_rms 0.115 #===END data_compound3 _database_code_depnum_ccdc_archive 'CCDC 851705' #TrackingRef '- CIF1-6.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H42 Bi2 N8 O18' _chemical_formula_weight 1316.76 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2386(5) _cell_length_b 10.7144(6) _cell_length_c 12.2516(6) _cell_angle_alpha 79.607(4) _cell_angle_beta 68.550(5) _cell_angle_gamma 78.703(5) _cell_volume 1098.98(10) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5849 _cell_measurement_theta_min 3.2902 _cell_measurement_theta_max 29.0886 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.990 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 636 _exptl_absorpt_coefficient_mu 8.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.268 _exptl_absorpt_correction_T_max 0.379 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 119.7(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 'Xcalibur, Eos, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1183 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8431 _diffrn_reflns_av_R_equivalents 0.0310 _diffrn_reflns_av_sigmaI/netI 0.0338 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.30 _diffrn_reflns_theta_max 29.15 _reflns_number_total 5022 _reflns_number_gt 4840 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; DFIX N4 H4A 0.95 0.01 DFIX N4 H4B 0.95 0.01 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^)+(0.0240P)^2^+0.4510P] 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 5022 _refine_ls_number_parameters 310 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0205 _refine_ls_R_factor_gt 0.0195 _refine_ls_wR_factor_ref 0.0480 _refine_ls_wR_factor_gt 0.0475 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6696(3) 0.0570(3) 0.6173(3) 0.0145(5) Uani 1 1 d . . . C2 C 0.8091(3) 0.1218(3) 0.5358(3) 0.0131(5) Uani 1 1 d . . . C3 C 0.9278(3) 0.1409(3) 0.5739(3) 0.0164(6) Uani 1 1 d . . . H3 H 0.9204 0.1186 0.6526 0.020 Uiso 1 1 calc R . . C4 C 1.0561(3) 0.1933(3) 0.4926(3) 0.0168(6) Uani 1 1 d . . . H4 H 1.1383 0.2034 0.5155 0.020 Uiso 1 1 calc R . . C5 C 1.0623(3) 0.2312(3) 0.3757(3) 0.0158(6) Uani 1 1 d . . . H5 H 1.1481 0.2659 0.3195 0.019 Uiso 1 1 calc R . . C6 C 0.9355(3) 0.2153(3) 0.3462(3) 0.0132(5) Uani 1 1 d . . . C7 C 0.9211(3) 0.2659(3) 0.2260(2) 0.0133(5) Uani 1 1 d . . . C11 C 0.5014(3) 0.2273(3) 0.1090(3) 0.0135(5) Uani 1 1 d . . . C12 C 0.6179(3) 0.1082(3) 0.0724(3) 0.0126(5) Uani 1 1 d . . . C13 C 0.6628(3) 0.0671(3) -0.0376(3) 0.0177(6) Uani 1 1 d . . . H13 H 0.6214 0.1127 -0.0942 0.021 Uiso 1 1 calc R . . C14 C 0.7711(4) -0.0437(3) -0.0620(3) 0.0209(6) Uani 1 1 d . . . H14 H 0.8011 -0.0739 -0.1348 0.025 Uiso 1 1 calc R . . C15 C 0.8337(4) -0.1084(3) 0.0231(3) 0.0206(6) Uani 1 1 d . . . H15 H 0.9069 -0.1820 0.0082 0.025 Uiso 1 1 calc R . . C16 C 0.7841(3) -0.0607(3) 0.1312(3) 0.0141(5) Uani 1 1 d . . . C17 C 0.8464(3) -0.1203(3) 0.2304(3) 0.0160(6) Uani 1 1 d . . . C21 C 0.3266(5) 0.4158(4) 0.7440(4) 0.0342(8) Uani 1 1 d . . . H21A H 0.4151 0.3649 0.7612 0.051 Uiso 1 1 calc R . . H21B H 0.2314 0.3877 0.7999 0.051 Uiso 1 1 calc R . . H21C H 0.3259 0.5042 0.7493 0.051 Uiso 1 1 calc R . . C22 C 0.2054(4) 0.4608(4) 0.5873(4) 0.0360(9) Uani 1 1 d . . . H22A H 0.1957 0.5523 0.5828 0.054 Uiso 1 1 calc R . . H22B H 0.1108 0.4318 0.6432 0.054 Uiso 1 1 calc R . . H22C H 0.2226 0.4376 0.5110 0.054 Uiso 1 1 calc R . . C23 C 0.4675(5) 0.3466(3) 0.5483(4) 0.0313(8) Uani 1 1 d . . . H23 H 0.5508 0.3122 0.5749 0.038 Uiso 1 1 calc R . . C31 C 0.8012(4) 0.4215(3) -0.0231(3) 0.0199(6) Uani 1 1 d . . . H31A H 0.7052 0.3954 0.0334 0.030 Uiso 1 1 calc R . . H31B H 0.8480 0.4655 0.0143 0.030 Uiso 1 1 calc R . . H31C H 0.8724 0.3472 -0.0527 0.030 Uiso 1 1 calc R . . C32 C 0.7243(4) 0.4431(3) -0.2011(3) 0.0223(6) Uani 1 1 d . . . H32A H 0.8103 0.3797 -0.2362 0.033 Uiso 1 1 calc R . . H32B H 0.7017 0.5049 -0.2620 0.033 Uiso 1 1 calc R . . H32C H 0.6333 0.4023 -0.1557 0.033 Uiso 1 1 calc R . . N1 N 0.8151(3) 0.1593(2) 0.4235(2) 0.0123(5) Uani 1 1 d . . . N2 N 0.6778(3) 0.0448(2) 0.1544(2) 0.0123(5) Uani 1 1 d . . . N3 N 0.3376(3) 0.4015(3) 0.6252(3) 0.0261(6) Uani 1 1 d . . . N4 N 0.7670(3) 0.5086(2) -0.1225(2) 0.0153(5) Uani 1 1 d D . . O1 O 0.5770(2) 0.0370(2) 0.56661(18) 0.0163(4) Uani 1 1 d . . . O2 O 0.6547(3) 0.0287(2) 0.7213(2) 0.0257(5) Uani 1 1 d . . . O3 O 0.8105(2) 0.2316(2) 0.20406(18) 0.0161(4) Uani 1 1 d . . . O4 O 1.0132(2) 0.3378(2) 0.15819(19) 0.0191(4) Uani 1 1 d . . . O5 O 0.4673(2) 0.2531(2) 0.21281(19) 0.0173(4) Uani 1 1 d . . . O6 O 0.4505(2) 0.2930(2) 0.03158(19) 0.0201(5) Uani 1 1 d . . . O7 O 0.7912(2) -0.06033(19) 0.32350(19) 0.0170(4) Uani 1 1 d . . . O8 O 0.9422(3) -0.2173(2) 0.2179(2) 0.0248(5) Uani 1 1 d . . . O9 O 0.4868(3) 0.3374(2) 0.4455(2) 0.0366(6) Uani 1 1 d . . . Bi1 Bi 0.613966(10) 0.120103(9) 0.341613(8) 0.01075(4) Uani 1 1 d . . . H4A H 0.687(4) 0.576(3) -0.088(4) 0.044(13) Uiso 1 1 d D . . H4B H 0.853(3) 0.555(3) -0.166(3) 0.018(9) 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 C1 0.0190(14) 0.0114(13) 0.0135(14) -0.0006(11) -0.0067(11) -0.0017(10) C2 0.0144(13) 0.0120(13) 0.0131(13) -0.0015(10) -0.0059(11) 0.0001(10) C3 0.0204(14) 0.0170(14) 0.0144(14) 0.0005(11) -0.0107(12) -0.0018(11) C4 0.0175(14) 0.0164(14) 0.0203(15) 0.0004(12) -0.0126(12) -0.0013(11) C5 0.0147(13) 0.0134(14) 0.0188(15) 0.0015(11) -0.0068(12) -0.0019(10) C6 0.0155(13) 0.0126(13) 0.0109(13) -0.0009(10) -0.0047(11) -0.0009(10) C7 0.0157(13) 0.0131(13) 0.0095(13) -0.0001(10) -0.0037(11) -0.0011(10) C11 0.0154(13) 0.0106(13) 0.0151(14) 0.0010(11) -0.0066(11) -0.0028(10) C12 0.0142(13) 0.0108(13) 0.0129(13) 0.0010(10) -0.0058(11) -0.0021(10) C13 0.0226(15) 0.0184(15) 0.0134(14) 0.0000(11) -0.0098(12) -0.0004(11) C14 0.0260(16) 0.0239(17) 0.0132(14) -0.0066(12) -0.0082(12) 0.0024(12) C15 0.0250(15) 0.0183(15) 0.0186(15) -0.0064(12) -0.0101(13) 0.0057(12) C16 0.0138(13) 0.0129(14) 0.0154(14) -0.0028(11) -0.0062(11) 0.0015(10) C17 0.0183(14) 0.0158(14) 0.0159(14) -0.0010(11) -0.0098(12) 0.0002(11) C21 0.041(2) 0.033(2) 0.029(2) -0.0151(16) -0.0101(17) -0.0017(16) C22 0.0328(19) 0.031(2) 0.044(2) -0.0112(17) -0.0143(18) 0.0059(15) C23 0.037(2) 0.0183(17) 0.037(2) -0.0114(15) -0.0120(17) 0.0053(14) C31 0.0248(15) 0.0161(15) 0.0202(16) 0.0048(12) -0.0131(13) -0.0017(12) C32 0.0270(16) 0.0230(17) 0.0199(16) -0.0039(13) -0.0106(13) -0.0039(12) N1 0.0144(11) 0.0113(11) 0.0116(11) -0.0012(9) -0.0057(9) -0.0006(9) N2 0.0137(11) 0.0131(12) 0.0102(11) 0.0005(9) -0.0053(9) -0.0016(9) N3 0.0305(15) 0.0202(14) 0.0279(16) -0.0102(12) -0.0097(13) 0.0018(11) N4 0.0172(12) 0.0140(12) 0.0150(12) 0.0005(10) -0.0073(10) -0.0015(9) O1 0.0193(10) 0.0214(11) 0.0110(10) 0.0031(8) -0.0075(8) -0.0096(8) O2 0.0258(12) 0.0426(15) 0.0115(11) 0.0039(10) -0.0079(9) -0.0151(10) O3 0.0162(10) 0.0215(11) 0.0117(10) 0.0029(8) -0.0061(8) -0.0069(8) O4 0.0221(11) 0.0226(12) 0.0149(11) 0.0041(9) -0.0082(9) -0.0107(9) O5 0.0192(10) 0.0173(11) 0.0152(10) -0.0027(8) -0.0083(9) 0.0033(8) O6 0.0244(11) 0.0186(11) 0.0180(11) 0.0004(9) -0.0128(9) 0.0039(8) O7 0.0223(10) 0.0147(10) 0.0146(10) -0.0019(8) -0.0099(9) 0.0034(8) O8 0.0288(12) 0.0218(12) 0.0250(13) -0.0076(10) -0.0160(10) 0.0112(9) O9 0.0507(16) 0.0219(13) 0.0273(14) -0.0082(11) -0.0051(12) 0.0057(11) Bi1 0.01232(6) 0.01103(6) 0.00870(6) 0.00013(4) -0.00433(4) -0.00096(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 C1 O2 1.218(4) . ? C1 O1 1.292(3) . ? C1 C2 1.516(4) . ? C2 N1 1.345(4) . ? C2 C3 1.400(4) . ? C3 C4 1.382(4) . ? C3 H3 0.9300 . ? C4 C5 1.400(4) . ? C4 H4 0.9300 . ? C5 C6 1.394(4) . ? C5 H5 0.9300 . ? C6 N1 1.334(4) . ? C6 C7 1.519(4) . ? C7 O4 1.231(3) . ? C7 O3 1.279(3) . ? C11 O6 1.254(3) . ? C11 O5 1.262(4) . ? C11 C12 1.518(4) . ? C12 N2 1.338(3) . ? C12 C13 1.383(4) . ? C13 C14 1.394(4) . ? C13 H13 0.9300 . ? C14 C15 1.387(4) . ? C14 H14 0.9300 . ? C15 C16 1.391(4) . ? C15 H15 0.9300 . ? C16 N2 1.341(4) . ? C16 C17 1.518(4) . ? C17 O8 1.218(4) . ? C17 O7 1.298(4) . ? C21 N3 1.456(5) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 N3 1.454(4) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 O9 1.225(5) . ? C23 N3 1.330(4) . ? C23 H23 0.9300 . ? C31 N4 1.487(4) . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C32 N4 1.484(4) . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? N1 Bi1 2.541(2) . ? N2 Bi1 2.399(2) . ? N4 H4A 0.957(10) . ? N4 H4B 0.950(10) . ? O1 Bi1 2.498(2) 2_656 ? O1 Bi1 2.656(2) . ? O3 Bi1 2.334(2) . ? O5 Bi1 2.521(2) . ? O7 Bi1 2.2622(19) . ? O9 Bi1 2.707(2) . ? Bi1 O1 2.498(2) 2_656 ? 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 O2 C1 O1 126.4(3) . . ? O2 C1 C2 118.9(3) . . ? O1 C1 C2 114.8(2) . . ? N1 C2 C3 121.0(3) . . ? N1 C2 C1 116.8(2) . . ? C3 C2 C1 122.2(3) . . ? C4 C3 C2 118.8(3) . . ? C4 C3 H3 120.6 . . ? C2 C3 H3 120.6 . . ? C3 C4 C5 119.9(3) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C6 C5 C4 117.8(3) . . ? C6 C5 H5 121.1 . . ? C4 C5 H5 121.1 . . ? N1 C6 C5 122.1(3) . . ? N1 C6 C7 115.4(2) . . ? C5 C6 C7 122.4(3) . . ? O4 C7 O3 124.9(3) . . ? O4 C7 C6 118.6(2) . . ? O3 C7 C6 116.5(2) . . ? O6 C11 O5 125.9(3) . . ? O6 C11 C12 116.4(3) . . ? O5 C11 C12 117.6(2) . . ? N2 C12 C13 121.4(3) . . ? N2 C12 C11 115.0(2) . . ? C13 C12 C11 123.6(3) . . ? C12 C13 C14 118.9(3) . . ? C12 C13 H13 120.6 . . ? C14 C13 H13 120.6 . . ? C15 C14 C13 119.5(3) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C14 C15 C16 118.4(3) . . ? C14 C15 H15 120.8 . . ? C16 C15 H15 120.8 . . ? N2 C16 C15 121.6(3) . . ? N2 C16 C17 114.8(2) . . ? C15 C16 C17 123.6(3) . . ? O8 C17 O7 125.3(3) . . ? O8 C17 C16 119.5(3) . . ? O7 C17 C16 115.3(2) . . ? N3 C21 H21A 109.5 . . ? N3 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N3 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N3 C22 H22A 109.5 . . ? N3 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N3 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O9 C23 N3 125.7(4) . . ? O9 C23 H23 117.1 . . ? N3 C23 H23 117.1 . . ? N4 C31 H31A 109.5 . . ? N4 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? N4 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? N4 C32 H32A 109.5 . . ? N4 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? N4 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C6 N1 C2 120.3(2) . . ? C6 N1 Bi1 115.86(18) . . ? C2 N1 Bi1 123.80(18) . . ? C12 N2 C16 120.3(2) . . ? C12 N2 Bi1 122.16(18) . . ? C16 N2 Bi1 117.41(18) . . ? C23 N3 C22 119.6(3) . . ? C23 N3 C21 122.6(3) . . ? C22 N3 C21 117.6(3) . . ? C32 N4 C31 113.8(2) . . ? C32 N4 H4A 113(3) . . ? C31 N4 H4A 107(3) . . ? C32 N4 H4B 112(2) . . ? C31 N4 H4B 110(2) . . ? H4A N4 H4B 101(3) . . ? C1 O1 Bi1 122.23(18) . 2_656 ? C1 O1 Bi1 122.73(18) . . ? Bi1 O1 Bi1 113.86(7) 2_656 . ? C7 O3 Bi1 124.86(18) . . ? C11 O5 Bi1 119.10(17) . . ? C17 O7 Bi1 123.73(17) . . ? C23 O9 Bi1 124.2(2) . . ? O7 Bi1 O3 88.73(8) . . ? O7 Bi1 N2 68.78(7) . . ? O3 Bi1 N2 72.45(8) . . ? O7 Bi1 O1 82.53(7) . 2_656 ? O3 Bi1 O1 161.58(7) . 2_656 ? N2 Bi1 O1 89.25(7) . 2_656 ? O7 Bi1 O5 134.49(7) . . ? O3 Bi1 O5 79.17(7) . . ? N2 Bi1 O5 65.73(7) . . ? O1 Bi1 O5 95.45(7) 2_656 . ? O7 Bi1 N1 74.63(7) . . ? O3 Bi1 N1 66.38(7) . . ? N2 Bi1 N1 124.50(7) . . ? O1 Bi1 N1 125.85(7) 2_656 . ? O5 Bi1 N1 134.98(7) . . ? O7 Bi1 O1 78.99(7) . . ? O3 Bi1 O1 128.05(6) . . ? N2 Bi1 O1 141.81(7) . . ? O1 Bi1 O1 66.14(7) 2_656 . ? O5 Bi1 O1 141.27(7) . . ? N1 Bi1 O1 61.68(7) . . ? O7 Bi1 O9 148.05(8) . . ? O3 Bi1 O9 88.26(8) . . ? N2 Bi1 O9 139.37(8) . . ? O1 Bi1 O9 107.66(8) 2_656 . ? O5 Bi1 O9 75.86(8) . . ? N1 Bi1 O9 75.05(8) . . ? O1 Bi1 O9 77.99(8) . . ? _diffrn_measured_fraction_theta_max 0.846 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.123 _refine_diff_density_min -1.030 _refine_diff_density_rms 0.118 #===END data_compound4 _database_code_depnum_ccdc_archive 'CCDC 851706' #TrackingRef '- CIF1-6.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H24 Bi2 N4 O18' _chemical_formula_weight 1170.51 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 9.1117(4) _cell_length_b 10.1375(3) _cell_length_c 10.8648(4) _cell_angle_alpha 67.217(3) _cell_angle_beta 71.802(3) _cell_angle_gamma 81.548(3) _cell_volume 878.61(6) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 7479 _cell_measurement_theta_min 3.1548 _cell_measurement_theta_max 29.2357 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.212 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 554 _exptl_absorpt_coefficient_mu 10.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.310 _exptl_absorpt_correction_T_max 0.446 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 120(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 'Xcalibur, Eos, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1183 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12997 _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_sigmaI/netI 0.0357 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 29.30 _reflns_number_total 4226 _reflns_number_gt 3986 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0370P)^2^+3.1537P] 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 4226 _refine_ls_number_parameters 255 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0330 _refine_ls_R_factor_gt 0.0307 _refine_ls_wR_factor_ref 0.0764 _refine_ls_wR_factor_gt 0.0746 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 C1 C 0.5736(6) -0.1092(6) 0.3203(5) 0.0252(10) Uani 1 1 d . . . C2 C 0.4206(6) -0.0625(6) 0.4008(5) 0.0233(10) Uani 1 1 d . . . C3 C 0.3451(6) -0.1475(6) 0.5345(6) 0.0303(11) Uani 1 1 d . . . H3 H 0.3860 -0.2370 0.5781 0.036 Uiso 1 1 calc R . . C4 C 0.2061(6) -0.0962(7) 0.6026(6) 0.0317(12) Uani 1 1 d . . . H4 H 0.1510 -0.1522 0.6916 0.038 Uiso 1 1 calc R . . C5 C 0.1518(6) 0.0385(6) 0.5362(5) 0.0281(11) Uani 1 1 d . . . H5 H 0.0615 0.0764 0.5812 0.034 Uiso 1 1 calc R . . C6 C 0.2332(6) 0.1172(6) 0.4013(5) 0.0237(10) Uani 1 1 d . . . C7 C 0.1791(6) 0.2608(6) 0.3189(5) 0.0263(10) Uani 1 1 d . . . C8 C 0.0002(8) 0.4515(7) 0.3303(7) 0.0427(15) Uani 1 1 d . . . H8A H 0.0790 0.5211 0.2912 0.064 Uiso 1 1 calc R . . H8B H -0.0845 0.4778 0.3962 0.064 Uiso 1 1 calc R . . H8C H -0.0357 0.4479 0.2574 0.064 Uiso 1 1 calc R . . C11 C 0.7858(6) 0.0500(5) -0.1401(5) 0.0218(9) Uani 1 1 d . . . C12 C 0.8652(5) 0.1447(5) -0.1025(5) 0.0207(9) Uani 1 1 d . . . C13 C 1.0246(6) 0.1585(6) -0.1456(5) 0.0242(10) Uani 1 1 d . . . H13 H 1.0879 0.1124 -0.2033 0.029 Uiso 1 1 calc R . . C14 C 1.0870(6) 0.2421(6) -0.1009(6) 0.0272(10) Uani 1 1 d . . . H14 H 1.1932 0.2538 -0.1295 0.033 Uiso 1 1 calc R . . C15 C 0.9906(6) 0.3089(6) -0.0127(5) 0.0256(10) Uani 1 1 d . . . H15 H 1.0308 0.3631 0.0207 0.031 Uiso 1 1 calc R . . C16 C 0.8316(6) 0.2914(5) 0.0235(5) 0.0226(9) Uani 1 1 d . . . C17 C 0.7144(6) 0.3600(5) 0.1163(5) 0.0244(10) Uani 1 1 d . . . C21 C 0.5942(9) 0.4130(9) -0.3026(8) 0.0528(18) Uani 1 1 d . . . H21A H 0.6335 0.5051 -0.3261 0.079 Uiso 1 1 calc R . . H21B H 0.5341 0.4202 -0.3636 0.079 Uiso 1 1 calc R . . H21C H 0.6789 0.3458 -0.3126 0.079 Uiso 1 1 calc R . . N1 N 0.3657(5) 0.0656(5) 0.3342(4) 0.0226(8) Uani 1 1 d . . . N2 N 0.7727(5) 0.2109(4) -0.0207(4) 0.0222(8) Uani 1 1 d . . . O1 O 0.6302(4) -0.0218(4) 0.1942(4) 0.0252(7) Uani 1 1 d . . . O2 O 0.6361(5) -0.2207(4) 0.3765(4) 0.0358(9) Uani 1 1 d . . . O3 O 0.2346(4) 0.3221(4) 0.1945(4) 0.0304(8) Uani 1 1 d . . . O4 O 0.0630(5) 0.3125(4) 0.3995(4) 0.0349(9) Uani 1 1 d . . . O5 O 0.6365(4) 0.0520(4) -0.0949(4) 0.0241(7) Uani 1 1 d . . . O6 O 0.8635(4) -0.0236(4) -0.2050(4) 0.0287(8) Uani 1 1 d . . . O7 O 0.5751(4) 0.3188(4) 0.1554(4) 0.0275(8) Uani 1 1 d . . . O8 O 0.7568(5) 0.4469(4) 0.1498(4) 0.0325(9) Uani 1 1 d . . . O9 O 0.5006(9) 0.3659(7) -0.1642(6) 0.091(3) Uani 1 1 d . . . Bi1 Bi 0.502564(19) 0.162373(18) 0.076833(17) 0.02086(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.021(2) 0.030(3) 0.023(2) -0.011(2) -0.0020(19) -0.0028(19) C2 0.018(2) 0.030(3) 0.024(2) -0.014(2) -0.0030(19) -0.0036(18) C3 0.026(3) 0.035(3) 0.026(3) -0.010(2) -0.003(2) -0.001(2) C4 0.025(3) 0.043(3) 0.024(3) -0.012(2) -0.002(2) -0.004(2) C5 0.024(2) 0.040(3) 0.020(2) -0.015(2) -0.0011(19) 0.000(2) C6 0.018(2) 0.032(3) 0.022(2) -0.015(2) 0.0009(18) -0.0011(19) C7 0.021(2) 0.034(3) 0.026(3) -0.016(2) -0.003(2) 0.000(2) C8 0.046(4) 0.041(3) 0.040(3) -0.020(3) -0.013(3) 0.015(3) C11 0.021(2) 0.027(2) 0.016(2) -0.0077(19) -0.0028(18) -0.0026(18) C12 0.016(2) 0.026(2) 0.017(2) -0.0076(18) 0.0015(17) -0.0028(17) C13 0.018(2) 0.028(2) 0.026(2) -0.012(2) -0.0015(19) 0.0001(18) C14 0.019(2) 0.029(3) 0.029(3) -0.011(2) -0.001(2) -0.0036(19) C15 0.023(2) 0.028(3) 0.025(3) -0.010(2) -0.002(2) -0.0052(19) C16 0.020(2) 0.026(2) 0.020(2) -0.0082(19) -0.0014(18) -0.0014(18) C17 0.021(2) 0.025(2) 0.024(2) -0.009(2) -0.0008(19) -0.0037(18) C21 0.050(4) 0.054(4) 0.047(4) -0.014(3) -0.007(3) -0.008(3) N1 0.0162(19) 0.032(2) 0.021(2) -0.0121(17) -0.0031(16) -0.0007(16) N2 0.0181(19) 0.025(2) 0.0191(19) -0.0067(16) 0.0004(15) -0.0025(15) O1 0.0173(16) 0.0307(19) 0.0234(18) -0.0101(15) -0.0001(13) 0.0004(13) O2 0.027(2) 0.038(2) 0.032(2) -0.0084(18) -0.0021(17) 0.0051(16) O3 0.0262(19) 0.035(2) 0.0266(19) -0.0124(16) -0.0031(15) 0.0013(15) O4 0.032(2) 0.040(2) 0.027(2) -0.0145(17) -0.0024(16) 0.0106(17) O5 0.0162(16) 0.0345(19) 0.0222(17) -0.0152(15) 0.0003(13) -0.0014(13) O6 0.0198(17) 0.041(2) 0.0301(19) -0.0229(17) 0.0001(15) -0.0007(15) O7 0.0228(18) 0.035(2) 0.0283(19) -0.0212(16) 0.0005(15) -0.0020(15) O8 0.031(2) 0.035(2) 0.034(2) -0.0208(17) 0.0011(16) -0.0076(16) O9 0.113(5) 0.065(4) 0.034(3) 0.001(3) 0.008(3) 0.060(4) Bi1 0.01666(10) 0.02688(11) 0.01910(10) -0.01202(8) -0.00099(7) 0.00072(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.212(7) . ? C1 O1 1.296(6) . ? C1 C2 1.516(7) . ? C2 N1 1.330(7) . ? C2 C3 1.381(7) . ? C3 C4 1.393(8) . ? C3 H3 0.9300 . ? C4 C5 1.376(8) . ? C4 H4 0.9300 . ? C5 C6 1.386(7) . ? C5 H5 0.9300 . ? C6 N1 1.350(6) . ? C6 C7 1.490(7) . ? C7 O3 1.218(6) . ? C7 O4 1.332(6) . ? C8 O4 1.446(7) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C11 O6 1.222(6) . ? C11 O5 1.294(6) . ? C11 C12 1.519(7) . ? C12 N2 1.333(6) . ? C12 C13 1.390(7) . ? C13 C14 1.382(7) . ? C13 H13 0.9300 . ? C14 C15 1.396(7) . ? C14 H14 0.9300 . ? C15 C16 1.396(7) . ? C15 H15 0.9300 . ? C16 N2 1.334(7) . ? C16 C17 1.514(7) . ? C17 O8 1.224(6) . ? C17 O7 1.283(6) . ? C21 O9 1.406(9) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? N1 Bi1 2.529(4) . ? N2 Bi1 2.397(4) . ? O1 Bi1 2.216(4) . ? O5 Bi1 2.453(3) . ? O5 Bi1 2.587(4) 2_655 ? O7 Bi1 2.322(4) . ? O9 Bi1 2.636(5) . ? Bi1 O5 2.587(4) 2_655 ? 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 O2 C1 O1 124.6(5) . . ? O2 C1 C2 119.5(5) . . ? O1 C1 C2 115.8(4) . . ? N1 C2 C3 122.7(5) . . ? N1 C2 C1 115.4(4) . . ? C3 C2 C1 121.9(5) . . ? C2 C3 C4 118.5(5) . . ? C2 C3 H3 120.7 . . ? C4 C3 H3 120.7 . . ? C5 C4 C3 119.0(5) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? C4 C5 C6 119.2(5) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? N1 C6 C5 121.6(5) . . ? N1 C6 C7 115.4(4) . . ? C5 C6 C7 123.0(4) . . ? O3 C7 O4 124.9(5) . . ? O3 C7 C6 124.1(5) . . ? O4 C7 C6 110.9(4) . . ? O4 C8 H8A 109.5 . . ? O4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O6 C11 O5 125.2(5) . . ? O6 C11 C12 119.7(4) . . ? O5 C11 C12 115.0(4) . . ? N2 C12 C13 121.5(5) . . ? N2 C12 C11 115.7(4) . . ? C13 C12 C11 122.7(4) . . ? C14 C13 C12 118.5(5) . . ? C14 C13 H13 120.7 . . ? C12 C13 H13 120.7 . . ? C13 C14 C15 120.0(5) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C14 C15 C16 117.7(5) . . ? C14 C15 H15 121.2 . . ? C16 C15 H15 121.2 . . ? N2 C16 C15 121.8(5) . . ? N2 C16 C17 115.3(4) . . ? C15 C16 C17 123.0(5) . . ? O8 C17 O7 124.9(5) . . ? O8 C17 C16 119.5(4) . . ? O7 C17 C16 115.6(4) . . ? O9 C21 H21A 109.5 . . ? O9 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O9 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C2 N1 C6 118.9(4) . . ? C2 N1 Bi1 113.0(3) . . ? C6 N1 Bi1 127.1(3) . . ? C12 N2 C16 120.5(4) . . ? C12 N2 Bi1 121.1(3) . . ? C16 N2 Bi1 117.9(3) . . ? C1 O1 Bi1 125.2(3) . . ? C7 O4 C8 115.8(4) . . ? C11 O5 Bi1 120.7(3) . . ? C11 O5 Bi1 116.9(3) . 2_655 ? Bi1 O5 Bi1 114.53(13) . 2_655 ? C17 O7 Bi1 122.5(3) . . ? C21 O9 Bi1 138.8(5) . . ? O1 Bi1 O7 93.07(14) . . ? O1 Bi1 N2 72.42(13) . . ? O7 Bi1 N2 68.13(13) . . ? O1 Bi1 O5 77.16(13) . . ? O7 Bi1 O5 134.06(12) . . ? N2 Bi1 O5 66.12(13) . . ? O1 Bi1 N1 67.61(13) . . ? O7 Bi1 N1 77.61(13) . . ? N2 Bi1 N1 124.85(13) . . ? O5 Bi1 N1 134.20(13) . . ? O1 Bi1 O5 78.28(12) . 2_655 ? O7 Bi1 O5 156.75(12) . 2_655 ? N2 Bi1 O5 127.50(12) . 2_655 ? O5 Bi1 O5 65.47(13) . 2_655 ? N1 Bi1 O5 79.14(12) . 2_655 ? O1 Bi1 O9 147.03(15) . . ? O7 Bi1 O9 92.4(2) . . ? N2 Bi1 O9 79.6(2) . . ? O5 Bi1 O9 75.78(15) . . ? N1 Bi1 O9 145.12(15) . . ? O5 Bi1 O9 106.7(2) 2_655 . ? _diffrn_measured_fraction_theta_max 0.882 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.699 _refine_diff_density_min -1.723 _refine_diff_density_rms 0.176 #===END data_compound5 _database_code_depnum_ccdc_archive 'CCDC 851707' #TrackingRef '- CIF1-6.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H27 Bi Li N5 O13' _chemical_formula_weight 821.44 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' Li Li -0.0003 0.0001 '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 14.249(5) _cell_length_b 10.089(5) _cell_length_c 21.025(5) _cell_angle_alpha 90.000 _cell_angle_beta 101.954(5) _cell_angle_gamma 90.000 _cell_volume 2957.0(19) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 13339 _cell_measurement_theta_min 3.1677 _cell_measurement_theta_max 70.9827 _exptl_crystal_description Rod _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.845 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1608 _exptl_absorpt_coefficient_mu 12.362 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.431 _exptl_absorpt_correction_T_max 0.610 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1183 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23864 _diffrn_reflns_av_R_equivalents 0.0175 _diffrn_reflns_av_sigmaI/netI 0.0134 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 25.86 _reflns_number_total 5668 _reflns_number_gt 5296 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0257P)^2^+9.7414P] 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 5668 _refine_ls_number_parameters 434 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0251 _refine_ls_R_factor_gt 0.0237 _refine_ls_wR_factor_ref 0.0626 _refine_ls_wR_factor_gt 0.0618 _refine_ls_goodness_of_fit_ref 1.137 _refine_ls_restrained_S_all 1.137 _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 C1 C 0.7149(2) 0.4633(3) 0.54129(16) 0.0147(7) Uani 1 1 d . . . C2 C 0.7029(2) 0.3324(3) 0.57417(16) 0.0146(7) Uani 1 1 d . . . C3 C 0.6919(3) 0.3242(4) 0.63857(17) 0.0194(7) Uani 1 1 d . . . H3 H 0.6921 0.4004 0.6635 0.023 Uiso 1 1 calc R . . C4 C 0.6810(3) 0.2007(4) 0.66437(17) 0.0209(7) Uani 1 1 d . . . H4 H 0.6723 0.1930 0.7069 0.025 Uiso 1 1 calc R . . C5 C 0.6828(2) 0.0886(4) 0.62692(16) 0.0178(7) Uani 1 1 d . . . H5 H 0.6754 0.0047 0.6435 0.021 Uiso 1 1 calc R . . C6 C 0.6961(2) 0.1046(3) 0.56375(16) 0.0142(7) Uani 1 1 d . . . C7 C 0.7052(2) -0.0113(3) 0.51977(16) 0.0146(7) Uani 1 1 d . . . C11 C 0.5024(3) 0.2253(4) 0.37257(17) 0.0156(7) Uani 1 1 d . . . C12 C 0.5376(2) 0.1334(3) 0.32486(15) 0.0149(7) Uani 1 1 d . . . C13 C 0.4750(2) 0.0626(4) 0.27652(16) 0.0168(7) Uani 1 1 d . . . H13 H 0.4089 0.0722 0.2712 0.020 Uiso 1 1 calc R . . C14 C 0.5136(3) -0.0218(4) 0.23684(17) 0.0195(7) Uani 1 1 d . . . H14 H 0.4736 -0.0700 0.2045 0.023 Uiso 1 1 calc R . . C15 C 0.6124(2) -0.0339(3) 0.24565(16) 0.0167(7) Uani 1 1 d . . . H15 H 0.6395 -0.0919 0.2201 0.020 Uiso 1 1 calc R . . C16 C 0.6704(2) 0.0426(3) 0.29359(15) 0.0137(6) Uani 1 1 d . . . C17 C 0.7793(2) 0.0400(3) 0.30725(15) 0.0120(6) Uani 1 1 d . . . C21 C 0.7788(2) 0.4634(3) 0.31299(15) 0.0125(6) Uani 1 1 d . . . C22 C 0.8796(2) 0.4471(3) 0.35399(15) 0.0149(7) Uani 1 1 d . . . C23 C 0.9602(3) 0.5005(4) 0.33591(17) 0.0198(7) Uani 1 1 d . . . H23 H 0.9544 0.5510 0.2983 0.024 Uiso 1 1 calc R . . C24 C 1.0497(3) 0.4768(4) 0.37548(18) 0.0233(8) Uani 1 1 d . . . H24 H 1.1050 0.5090 0.3639 0.028 Uiso 1 1 calc R . . C25 C 1.0558(2) 0.4050(4) 0.43206(17) 0.0205(7) Uani 1 1 d . . . H25 H 1.1149 0.3902 0.4596 0.025 Uiso 1 1 calc R . . C26 C 0.9720(2) 0.3554(3) 0.44717(16) 0.0154(7) Uani 1 1 d . . . C27 C 0.9703(3) 0.2693(4) 0.50619(17) 0.0176(7) Uani 1 1 d . . . C31 C 0.9391(3) 0.1523(4) 0.6709(2) 0.0303(9) Uani 1 1 d . . . H31A H 0.8916 0.1985 0.6397 0.045 Uiso 1 1 calc R . . H31B H 0.9756 0.2149 0.7004 0.045 Uiso 1 1 calc R . . H31C H 0.9081 0.0909 0.6947 0.045 Uiso 1 1 calc R . . C32 C 0.9572(3) -0.0379(4) 0.6003(2) 0.0355(10) Uani 1 1 d . . . H32A H 0.9338 -0.0961 0.6296 0.053 Uiso 1 1 calc R . . H32B H 1.0031 -0.0840 0.5808 0.053 Uiso 1 1 calc R . . H32C H 0.9046 -0.0090 0.5669 0.053 Uiso 1 1 calc R . . C33 C 0.7189(4) -0.2632(4) 0.3835(2) 0.0393(12) Uani 1 1 d . . . H33A H 0.6901 -0.3095 0.3445 0.059 Uiso 1 1 calc R . . H33B H 0.7836 -0.2934 0.3983 0.059 Uiso 1 1 calc R . . H33C H 0.7191 -0.1698 0.3749 0.059 Uiso 1 1 calc R . . C34 C 0.5658(5) -0.2587(12) 0.4146(5) 0.166(7) Uani 1 1 d . . . H34A H 0.5551 -0.1687 0.4261 0.249 Uiso 1 1 calc R . . H34B H 0.5296 -0.3172 0.4364 0.249 Uiso 1 1 calc R . . H34C H 0.5456 -0.2697 0.3685 0.249 Uiso 1 1 calc R . . N1 N 0.70440(19) 0.2244(3) 0.53817(13) 0.0112(5) Uani 1 1 d . . . N2 N 0.63254(19) 0.1242(3) 0.33187(12) 0.0127(5) Uani 1 1 d . . . N3 N 0.88621(19) 0.3761(3) 0.40824(13) 0.0138(6) Uani 1 1 d . . . N4 N 1.0039(2) 0.0792(3) 0.63670(15) 0.0217(6) Uani 1 1 d . . . N5 N 0.6640(3) -0.2888(4) 0.43354(18) 0.0344(9) Uani 1 1 d . . . O1 O 0.72761(17) 0.4577(2) 0.48327(11) 0.0160(5) Uani 1 1 d . . . O2 O 0.71268(18) 0.5661(2) 0.57294(12) 0.0204(5) Uani 1 1 d . . . O3 O 0.71094(19) 0.0153(2) 0.46220(11) 0.0199(5) Uani 1 1 d . . . O4 O 0.70714(18) -0.1262(2) 0.54295(11) 0.0189(5) Uani 1 1 d . . . O5 O 0.56548(18) 0.2839(3) 0.41377(12) 0.0201(5) Uani 1 1 d . . . O6 O 0.41433(18) 0.2345(2) 0.36668(13) 0.0192(5) Uani 1 1 d . . . O7 O 0.82278(16) 0.1117(3) 0.35283(11) 0.0191(5) Uani 1 1 d . . . O8 O 0.81909(17) -0.0337(2) 0.27281(11) 0.0190(5) Uani 1 1 d . . . O9 O 0.71170(17) 0.4046(3) 0.33299(11) 0.0191(5) Uani 1 1 d . . . O10 O 0.76933(18) 0.5332(3) 0.26366(11) 0.0194(5) Uani 1 1 d . . . O11 O 0.89085(18) 0.2190(3) 0.51005(12) 0.0214(5) Uani 1 1 d . . . O12 O 1.0474(2) 0.2542(2) 0.54655(13) 0.0219(6) Uani 1 1 d . . . O13 O 0.8027(2) 0.7531(3) 0.68838(13) 0.0155(5) Uani 1 1 d . . . Bi1 Bi 0.739382(8) 0.248650(11) 0.424967(5) 0.01053(6) Uani 1 1 d . . . Li1 Li 0.7035(4) 0.7395(5) 0.6077(3) 0.0149(12) Uani 1 1 d . . . H4NA H 1.024(4) 0.137(6) 0.606(3) 0.052(16) Uiso 1 1 d . . . H4NB H 1.062(3) 0.039(4) 0.6678(19) 0.018(10) Uiso 1 1 d . . . H5NA H 0.683(5) -0.232(6) 0.460(3) 0.053(19) Uiso 1 1 d . . . H5NB H 0.673(6) -0.380(9) 0.442(4) 0.12(3) Uiso 1 1 d . . . 13OA H 0.802(3) 0.690(5) 0.710(2) 0.019(11) Uiso 1 1 d . . . 13OB H 0.800(3) 0.813(5) 0.713(2) 0.027(13) 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 C1 0.0094(15) 0.0175(18) 0.0161(16) -0.0044(13) 0.0000(12) 0.0003(13) C2 0.0123(15) 0.0173(17) 0.0134(15) -0.0025(13) 0.0011(12) 0.0008(13) C3 0.0229(18) 0.0194(19) 0.0159(16) -0.0048(14) 0.0045(14) 0.0022(14) C4 0.0254(19) 0.025(2) 0.0126(16) 0.0017(14) 0.0044(14) 0.0010(16) C5 0.0228(17) 0.0169(18) 0.0142(16) 0.0042(13) 0.0054(13) 0.0021(14) C6 0.0112(15) 0.0177(18) 0.0130(15) 0.0021(13) 0.0007(12) 0.0000(13) C7 0.0159(16) 0.0140(17) 0.0134(15) 0.0020(13) 0.0019(12) -0.0014(13) C11 0.0157(17) 0.0192(17) 0.0118(16) 0.0048(13) 0.0026(13) 0.0015(14) C12 0.0133(15) 0.0171(17) 0.0138(15) 0.0056(13) 0.0020(12) -0.0006(13) C13 0.0113(15) 0.0228(19) 0.0152(16) 0.0048(14) 0.0001(12) -0.0029(13) C14 0.0185(17) 0.0228(19) 0.0146(16) 0.0024(14) -0.0023(13) -0.0074(14) C15 0.0193(17) 0.0167(17) 0.0137(15) -0.0007(13) 0.0025(13) -0.0016(14) C16 0.0151(16) 0.0146(17) 0.0110(15) 0.0035(12) 0.0018(12) -0.0016(13) C17 0.0135(15) 0.0116(16) 0.0104(15) 0.0015(12) 0.0009(12) -0.0011(12) C21 0.0163(16) 0.0098(16) 0.0110(15) -0.0005(12) 0.0017(12) -0.0007(13) C22 0.0178(16) 0.0133(17) 0.0127(15) -0.0024(12) 0.0012(13) 0.0000(13) C23 0.0219(18) 0.0220(19) 0.0163(16) 0.0012(14) 0.0055(14) -0.0051(15) C24 0.0152(17) 0.029(2) 0.0263(19) 0.0003(16) 0.0053(14) -0.0049(15) C25 0.0136(16) 0.024(2) 0.0220(18) -0.0020(15) 0.0002(13) -0.0030(14) C26 0.0153(16) 0.0156(17) 0.0142(15) -0.0023(13) 0.0007(12) 0.0003(13) C27 0.0162(17) 0.0225(19) 0.0131(17) -0.0005(13) 0.0005(14) 0.0023(14) C31 0.028(2) 0.037(2) 0.027(2) 0.0059(18) 0.0076(16) 0.0059(18) C32 0.026(2) 0.024(2) 0.050(3) -0.0012(19) -0.0062(19) 0.0013(17) C33 0.060(3) 0.031(3) 0.029(2) -0.0060(17) 0.015(2) 0.002(2) C34 0.028(3) 0.324(17) 0.141(9) -0.180(11) 0.007(4) -0.023(6) N1 0.0104(13) 0.0144(14) 0.0085(13) -0.0002(10) 0.0014(10) 0.0004(11) N2 0.0133(13) 0.0143(14) 0.0096(12) 0.0041(10) 0.0004(10) -0.0014(11) N3 0.0131(13) 0.0155(14) 0.0124(13) -0.0008(11) 0.0014(10) -0.0006(11) N4 0.0168(15) 0.0233(17) 0.0234(16) 0.0043(13) 0.0000(12) 0.0025(13) N5 0.058(3) 0.024(2) 0.0211(18) -0.0081(16) 0.0079(16) -0.0099(19) O1 0.0214(12) 0.0114(12) 0.0161(12) -0.0017(9) 0.0064(9) -0.0014(9) O2 0.0262(13) 0.0148(13) 0.0203(12) -0.0054(10) 0.0049(10) 0.0016(10) O3 0.0351(15) 0.0130(12) 0.0126(11) 0.0021(9) 0.0072(10) -0.0005(11) O4 0.0291(13) 0.0118(12) 0.0161(12) 0.0036(9) 0.0055(10) -0.0003(10) O5 0.0153(12) 0.0286(14) 0.0159(12) -0.0029(11) 0.0016(10) 0.0015(11) O6 0.0106(12) 0.0249(14) 0.0225(14) -0.0001(10) 0.0041(10) 0.0007(9) O7 0.0124(11) 0.0245(14) 0.0191(12) -0.0080(10) 0.0005(9) -0.0011(10) O8 0.0177(12) 0.0213(13) 0.0174(12) -0.0067(10) 0.0023(10) 0.0021(10) O9 0.0147(12) 0.0236(14) 0.0170(12) 0.0083(10) -0.0015(9) -0.0020(10) O10 0.0238(13) 0.0198(13) 0.0136(12) 0.0056(10) 0.0012(10) -0.0023(10) O11 0.0145(12) 0.0328(14) 0.0155(12) 0.0089(11) -0.0003(10) -0.0005(11) O12 0.0160(13) 0.0300(16) 0.0175(14) 0.0053(10) -0.0020(11) 0.0007(10) O13 0.0214(14) 0.0129(14) 0.0117(13) -0.0004(10) 0.0023(10) 0.0017(9) Bi1 0.01293(8) 0.01125(8) 0.00696(8) 0.00030(4) 0.00103(5) -0.00021(4) Li1 0.017(3) 0.015(3) 0.012(3) 0.000(2) 0.002(2) 0.001(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 C1 O2 1.236(4) . ? C1 O1 1.271(4) . ? C1 C2 1.517(5) . ? C2 N1 1.330(4) . ? C2 C3 1.397(5) . ? C3 C4 1.381(6) . ? C3 H3 0.9300 . ? C4 C5 1.382(5) . ? C4 H4 0.9300 . ? C5 C6 1.389(5) . ? C5 H5 0.9300 . ? C6 N1 1.338(4) . ? C6 C7 1.513(5) . ? C7 O4 1.256(4) . ? C7 O3 1.259(4) . ? C11 O6 1.238(4) . ? C11 O5 1.259(4) . ? C11 C12 1.526(5) . ? C12 N2 1.334(4) . ? C12 C13 1.401(5) . ? C13 C14 1.384(5) . ? C13 H13 0.9300 . ? C14 C15 1.386(5) . ? C14 H14 0.9300 . ? C15 C16 1.396(5) . ? C15 H15 0.9300 . ? C16 N2 1.340(4) . ? C16 C17 1.519(4) . ? C17 O8 1.253(4) . ? C17 O7 1.256(4) . ? C21 O10 1.237(4) . ? C21 O9 1.269(4) . ? C21 C22 1.523(4) . ? C22 N3 1.334(4) . ? C22 C23 1.390(5) . ? C23 C24 1.392(5) . ? C23 H23 0.9300 . ? C24 C25 1.380(5) . ? C24 H24 0.9300 . ? C25 C26 1.392(5) . ? C25 H25 0.9300 . ? C26 N3 1.339(4) . ? C26 C27 1.519(5) . ? C27 O12 1.250(5) . ? C27 O11 1.258(5) . ? C31 N4 1.478(5) . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C32 N4 1.488(5) . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 N5 1.458(6) . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? C34 N5 1.406(9) . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? N1 Bi1 2.542(3) . ? N2 Bi1 2.548(3) . ? N3 Bi1 2.542(3) . ? N4 H4NA 0.96(6) . ? N4 H4NB 1.03(4) . ? N5 H5NA 0.80(6) . ? N5 H5NB 0.94(9) . ? O1 Bi1 2.463(2) . ? O2 Li1 1.911(6) . ? O3 Bi1 2.540(3) . ? O4 Li1 1.929(6) 1_545 ? O5 Bi1 2.466(3) . ? O6 Li1 1.885(7) 3_666 ? O7 Bi1 2.524(2) . ? O9 Bi1 2.461(2) . ? O11 Bi1 2.520(3) . ? O13 Li1 1.975(7) . ? O13 13OA 0.79(5) . ? O13 13OB 0.80(5) . ? Li1 O6 1.885(7) 3_666 ? Li1 O4 1.929(6) 1_565 ? 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 O2 C1 O1 125.4(3) . . ? O2 C1 C2 117.8(3) . . ? O1 C1 C2 116.8(3) . . ? N1 C2 C3 121.5(3) . . ? N1 C2 C1 115.9(3) . . ? C3 C2 C1 122.6(3) . . ? C4 C3 C2 118.6(3) . . ? C4 C3 H3 120.7 . . ? C2 C3 H3 120.7 . . ? C3 C4 C5 119.9(3) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C4 C5 C6 118.2(3) . . ? C4 C5 H5 120.9 . . ? C6 C5 H5 120.9 . . ? N1 C6 C5 122.0(3) . . ? N1 C6 C7 115.2(3) . . ? C5 C6 C7 122.7(3) . . ? O4 C7 O3 124.7(3) . . ? O4 C7 C6 118.3(3) . . ? O3 C7 C6 117.0(3) . . ? O6 C11 O5 126.7(3) . . ? O6 C11 C12 116.4(3) . . ? O5 C11 C12 116.9(3) . . ? N2 C12 C13 121.6(3) . . ? N2 C12 C11 115.7(3) . . ? C13 C12 C11 122.7(3) . . ? C14 C13 C12 118.6(3) . . ? C14 C13 H13 120.7 . . ? C12 C13 H13 120.7 . . ? C13 C14 C15 119.6(3) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C14 C15 C16 118.7(3) . . ? C14 C15 H15 120.6 . . ? C16 C15 H15 120.6 . . ? N2 C16 C15 121.4(3) . . ? N2 C16 C17 114.8(3) . . ? C15 C16 C17 123.8(3) . . ? O8 C17 O7 124.9(3) . . ? O8 C17 C16 117.9(3) . . ? O7 C17 C16 117.2(3) . . ? O10 C21 O9 125.8(3) . . ? O10 C21 C22 117.5(3) . . ? O9 C21 C22 116.7(3) . . ? N3 C22 C23 121.8(3) . . ? N3 C22 C21 115.6(3) . . ? C23 C22 C21 122.6(3) . . ? C22 C23 C24 118.4(3) . . ? C22 C23 H23 120.8 . . ? C24 C23 H23 120.8 . . ? C25 C24 C23 119.5(3) . . ? C25 C24 H24 120.3 . . ? C23 C24 H24 120.3 . . ? C24 C25 C26 118.8(3) . . ? C24 C25 H25 120.6 . . ? C26 C25 H25 120.6 . . ? N3 C26 C25 121.5(3) . . ? N3 C26 C27 115.0(3) . . ? C25 C26 C27 123.5(3) . . ? O12 C27 O11 125.6(3) . . ? O12 C27 C26 117.7(3) . . ? O11 C27 C26 116.7(3) . . ? N4 C31 H31A 109.5 . . ? N4 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? N4 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? N4 C32 H32A 109.5 . . ? N4 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? N4 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? N5 C33 H33A 109.5 . . ? N5 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? N5 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? N5 C34 H34A 109.5 . . ? N5 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? N5 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C2 N1 C6 119.9(3) . . ? C2 N1 Bi1 118.9(2) . . ? C6 N1 Bi1 121.0(2) . . ? C12 N2 C16 120.1(3) . . ? C12 N2 Bi1 118.8(2) . . ? C16 N2 Bi1 120.9(2) . . ? C22 N3 C26 120.0(3) . . ? C22 N3 Bi1 118.4(2) . . ? C26 N3 Bi1 120.6(2) . . ? C31 N4 C32 112.9(3) . . ? C31 N4 H4NA 109(3) . . ? C32 N4 H4NA 108(3) . . ? C31 N4 H4NB 113(2) . . ? C32 N4 H4NB 103(2) . . ? H4NA N4 H4NB 111(4) . . ? C34 N5 C33 114.1(6) . . ? C34 N5 H5NA 102(5) . . ? C33 N5 H5NA 102(5) . . ? C34 N5 H5NB 110(5) . . ? C33 N5 H5NB 104(5) . . ? H5NA N5 H5NB 124(7) . . ? C1 O1 Bi1 123.6(2) . . ? C1 O2 Li1 170.2(3) . . ? C7 O3 Bi1 122.7(2) . . ? C7 O4 Li1 157.0(3) . 1_545 ? C11 O5 Bi1 124.0(2) . . ? C11 O6 Li1 157.8(3) . 3_666 ? C17 O7 Bi1 123.7(2) . . ? C21 O9 Bi1 123.4(2) . . ? C27 O11 Bi1 123.8(2) . . ? Li1 O13 13OA 111(3) . . ? Li1 O13 13OB 119(3) . . ? 13OA O13 13OB 103(5) . . ? O9 Bi1 O1 80.04(9) . . ? O9 Bi1 O5 80.70(8) . . ? O1 Bi1 O5 75.72(8) . . ? O9 Bi1 O11 127.45(8) . . ? O1 Bi1 O11 83.38(9) . . ? O5 Bi1 O11 141.35(8) . . ? O9 Bi1 O7 84.07(9) . . ? O1 Bi1 O7 149.01(8) . . ? O5 Bi1 O7 127.63(8) . . ? O11 Bi1 O7 85.47(8) . . ? O9 Bi1 O3 145.60(8) . . ? O1 Bi1 O3 127.51(8) . . ? O5 Bi1 O3 86.66(9) . . ? O11 Bi1 O3 80.75(9) . . ? O7 Bi1 O3 78.62(8) . . ? O9 Bi1 N3 64.55(8) . . ? O1 Bi1 N3 77.19(9) . . ? O5 Bi1 N3 138.90(9) . . ? O11 Bi1 N3 63.23(9) . . ? O7 Bi1 N3 71.96(9) . . ? O3 Bi1 N3 134.44(9) . . ? O9 Bi1 N1 140.05(9) . . ? O1 Bi1 N1 64.52(9) . . ? O5 Bi1 N1 73.46(8) . . ? O11 Bi1 N1 68.23(9) . . ? O7 Bi1 N1 135.87(9) . . ? O3 Bi1 N1 63.10(8) . . ? N3 Bi1 N1 120.32(9) . . ? O9 Bi1 N2 74.84(9) . . ? O1 Bi1 N2 135.49(8) . . ? O5 Bi1 N2 64.47(9) . . ? O11 Bi1 N2 140.78(9) . . ? O7 Bi1 N2 63.20(8) . . ? O3 Bi1 N2 70.84(8) . . ? N3 Bi1 N2 121.41(8) . . ? N1 Bi1 N2 118.02(9) . . ? O6 Li1 O2 111.8(3) 3_666 . ? O6 Li1 O4 105.0(3) 3_666 1_565 ? O2 Li1 O4 111.0(3) . 1_565 ? O6 Li1 O13 105.4(3) 3_666 . ? O2 Li1 O13 107.4(3) . . ? O4 Li1 O13 116.0(3) 1_565 . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.86 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 2.384 _refine_diff_density_min -1.132 _refine_diff_density_rms 0.111 #===END data_compound6 _database_code_depnum_ccdc_archive 'CCDC 851708' #TrackingRef '- CIF1-6.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H16 Bi Li5 N4 O18' _chemical_formula_weight 940.13 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' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Li Li -0.0003 0.0001 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 9.674(5) _cell_length_b 11.078(5) _cell_length_c 16.972(5) _cell_angle_alpha 90.00 _cell_angle_beta 115.427(18) _cell_angle_gamma 90.00 _cell_volume 1642.7(12) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9757 _cell_measurement_theta_min 3.9773 _cell_measurement_theta_max 68.1179 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.080 _exptl_crystal_size_mid 0.050 _exptl_crystal_size_min 0.040 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.901 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 908 _exptl_absorpt_coefficient_mu 11.325 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.757 _exptl_absorpt_correction_T_max 0.804 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1183 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15105 _diffrn_reflns_av_R_equivalents 0.0629 _diffrn_reflns_av_sigmaI/netI 0.0354 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 25.39 _reflns_number_total 2977 _reflns_number_gt 2883 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; DFIX O9 H1 0.85 0.01 DFIX O9 H9 0.85 0.01 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^)+(0.0520P)^2^+2.3256P] 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 2977 _refine_ls_number_parameters 262 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0294 _refine_ls_R_factor_gt 0.0285 _refine_ls_wR_factor_ref 0.0783 _refine_ls_wR_factor_gt 0.0777 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.080 _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 C1 C 0.3811(5) 0.4395(4) 0.3115(3) 0.0153(8) Uani 1 1 d . . . C2 C 0.3770(5) 0.5483(4) 0.3649(3) 0.0192(9) Uani 1 1 d . . . C3 C 0.5067(5) 0.6078(5) 0.4218(3) 0.0290(10) Uani 1 1 d . . . H3 H 0.6057 0.5796 0.4318 0.035 Uiso 1 1 calc R . . C4 C 0.4891(6) 0.7107(5) 0.4642(4) 0.0387(13) Uani 1 1 d . . . H4 H 0.5762 0.7556 0.5019 0.046 Uiso 1 1 calc R . . C5 C 0.3450(5) 0.7463(4) 0.4510(3) 0.0283(10) Uani 1 1 d . . . H5 H 0.3311 0.8149 0.4805 0.034 Uiso 1 1 calc R . . C6 C 0.2203(5) 0.6810(4) 0.3943(3) 0.0173(8) Uani 1 1 d . . . C7 C 0.0585(5) 0.7106(4) 0.3787(3) 0.0172(9) Uani 1 1 d . . . C11 C 0.1026(5) 0.2667(4) 0.4065(3) 0.0156(8) Uani 1 1 d . . . C12 C 0.0522(5) 0.1900(4) 0.3249(3) 0.0153(8) Uani 1 1 d . . . C13 C 0.0580(5) 0.0636(4) 0.3281(3) 0.0204(9) Uani 1 1 d . . . H13 H 0.1004 0.0219 0.3823 0.025 Uiso 1 1 calc R . . C14 C 0.0000 0.0019(6) 0.2500 0.0263(16) Uani 1 2 d S . . H14 H 0.0000 -0.0839 0.2500 0.032 Uiso 1 2 calc SR . . C21 C 0.7469(4) 0.0865(4) 0.3722(3) 0.0154(8) Uani 1 1 d . A . C22 C 0.6192(6) 0.0084(4) 0.3086(3) 0.0205(10) Uani 1 1 d . . . C23B C 0.6110(12) -0.1180(9) 0.3194(7) 0.018(2) Uiso 0.50 1 d P A -2 Bi1 Bi 0.0000 0.476704(16) 0.2500 0.01291(10) Uani 1 2 d S . . Li1 Li 0.7315(8) 0.3694(7) 0.3684(5) 0.0207(15) Uani 1 1 d . . . Li2 Li -0.0381(8) 0.8853(6) 0.4793(5) 0.0189(14) Uani 1 1 d . . . N1 N 0.2371(4) 0.5839(3) 0.3521(2) 0.0140(7) Uani 1 1 d . . . N2 N 0.0000 0.2495(4) 0.2500 0.0135(9) Uani 1 2 d S . . N3 N 0.5000 0.0686(4) 0.2500 0.0158(10) Uani 1 2 d S . . O2 O 0.5037(3) 0.3839(3) 0.3335(2) 0.0194(6) Uani 1 1 d . . . O1 O 0.2565(3) 0.4133(3) 0.24678(18) 0.0169(6) Uani 1 1 d . . . O3 O -0.0450(3) 0.6351(3) 0.3348(2) 0.0196(6) Uani 1 1 d . . . O4 O 0.0376(4) 0.8062(3) 0.4093(2) 0.0202(6) Uani 1 1 d . . . O5 O 0.0961(4) 0.3805(3) 0.39622(19) 0.0192(6) Uani 1 1 d . . . O6 O 0.1474(3) 0.2148(3) 0.47822(19) 0.0199(6) Uani 1 1 d . . . O7 O 0.7290(3) 0.1986(3) 0.36110(19) 0.0186(6) Uani 1 1 d . . . O8 O 0.8591(4) 0.0353(2) 0.4304(2) 0.0155(6) Uani 1 1 d . . . O9 O 0.8335(4) 0.5059(3) 0.4379(2) 0.0217(7) Uani 1 1 d D . . Li3 Li 0.5000 0.2505(10) 0.2500 0.030(3) Uani 1 2 d S . . C23A C 0.6386(11) -0.1167(8) 0.3029(6) 0.016(2) Uiso 0.50 1 d P . 1 C24A C 0.5159(12) -0.1793(7) 0.2411(7) 0.021(2) Uiso 0.50 1 d P . 1 H1 H 0.863(6) 0.550(5) 0.407(3) 0.025(14) Uiso 1 1 d D . . H9 H 0.870(8) 0.528(5) 0.4910(13) 0.033(18) 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 C1 0.0124(19) 0.0162(19) 0.018(2) 0.0000(17) 0.0072(16) -0.0005(17) C2 0.021(2) 0.0149(18) 0.024(2) 0.0010(18) 0.0116(19) 0.0023(18) C3 0.017(2) 0.035(3) 0.032(3) -0.013(2) 0.0073(19) 0.000(2) C4 0.020(2) 0.038(3) 0.049(3) -0.024(3) 0.006(2) -0.002(2) C5 0.022(2) 0.025(2) 0.036(3) -0.015(2) 0.011(2) -0.0048(19) C6 0.0153(19) 0.0159(19) 0.020(2) -0.0016(17) 0.0064(16) 0.0017(16) C7 0.021(2) 0.017(2) 0.018(2) 0.0006(17) 0.0124(17) 0.0000(17) C11 0.0129(18) 0.017(2) 0.017(2) 0.0010(17) 0.0067(16) -0.0001(16) C12 0.0170(19) 0.0124(18) 0.019(2) 0.0006(16) 0.0102(16) -0.0001(16) C13 0.032(2) 0.012(2) 0.023(2) 0.0045(18) 0.017(2) 0.0037(19) C14 0.043(5) 0.015(3) 0.031(4) 0.000 0.025(4) 0.000 C21 0.0134(18) 0.019(2) 0.0127(18) 0.0012(16) 0.0041(15) 0.0045(16) C22 0.023(3) 0.016(2) 0.018(2) 0.0028(18) 0.005(2) 0.0047(18) Bi1 0.01373(14) 0.00958(14) 0.01559(15) 0.000 0.00645(10) 0.000 Li1 0.018(3) 0.019(3) 0.024(4) 0.000(3) 0.009(3) 0.001(3) Li2 0.016(3) 0.018(3) 0.020(3) -0.001(3) 0.005(3) 0.002(3) N1 0.0108(15) 0.0175(17) 0.0133(16) -0.0012(14) 0.0048(13) 0.0015(13) N2 0.013(2) 0.011(2) 0.017(2) 0.000 0.0063(19) 0.000 N3 0.016(2) 0.011(2) 0.018(2) 0.000 0.004(2) 0.000 O2 0.0168(14) 0.0177(14) 0.0237(15) -0.0015(12) 0.0088(12) 0.0034(12) O1 0.0180(14) 0.0150(13) 0.0184(14) -0.0027(11) 0.0085(12) -0.0006(11) O3 0.0178(14) 0.0163(14) 0.0268(16) -0.0063(12) 0.0117(13) -0.0010(12) O4 0.0237(15) 0.0154(14) 0.0250(16) -0.0036(12) 0.0138(13) 0.0015(13) O5 0.0277(16) 0.0126(14) 0.0160(14) -0.0020(12) 0.0082(12) -0.0020(12) O6 0.0186(15) 0.0220(15) 0.0181(15) 0.0025(12) 0.0069(12) -0.0033(12) O7 0.0177(14) 0.0138(14) 0.0213(15) 0.0022(12) 0.0056(12) 0.0021(12) O8 0.0133(15) 0.0138(14) 0.0160(15) 0.0003(11) 0.0032(13) 0.0019(11) O9 0.0193(17) 0.0231(14) 0.025(2) -0.0077(14) 0.0120(15) -0.0067(13) Li3 0.031(6) 0.019(5) 0.042(7) 0.000 0.018(5) 0.000 _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 C1 O2 1.243(5) . ? C1 O1 1.268(5) . ? C1 C2 1.519(6) . ? C2 N1 1.335(6) . ? C2 C3 1.379(7) . ? C3 C4 1.397(7) . ? C3 H3 0.9500 . ? C4 C5 1.372(7) . ? C4 H4 0.9500 . ? C5 C6 1.381(6) . ? C5 H5 0.9500 . ? C6 N1 1.340(5) . ? C6 C7 1.507(6) . ? C7 O4 1.234(5) . ? C7 O3 1.271(5) . ? C11 O6 1.243(5) . ? C11 O5 1.270(5) . ? C11 C12 1.516(6) . ? C12 N2 1.324(5) . ? C12 C13 1.401(6) . ? C13 C14 1.379(6) . ? C13 H13 0.9500 . ? C14 C13 1.379(6) 2 ? C14 H14 0.9500 . ? C21 O8 1.246(5) . ? C21 O7 1.257(5) . ? C21 C22 1.516(6) . ? C22 N3 1.334(6) . ? C22 C23A 1.407(10) . ? C22 C23B 1.419(11) . ? Bi1 O3 2.424(3) 2 ? Bi1 O3 2.424(3) . ? Bi1 O5 2.486(3) 2 ? Bi1 O5 2.486(3) . ? Bi1 N1 2.502(3) . ? Bi1 N1 2.502(3) 2 ? Bi1 N2 2.517(5) . ? Bi1 O1 2.601(3) 2 ? Bi1 O1 2.601(3) . ? Li1 O7 1.896(8) . ? Li1 O9 1.911(8) . ? Li1 O2 2.028(8) . ? Li1 O1 2.066(8) 2_655 ? Li1 Li3 2.632(9) . ? Li1 H1 2.31(5) . ? Li2 O4 1.861(7) . ? Li2 O6 1.877(8) 3_566 ? Li2 O8 1.932(8) 1_465 ? Li2 O8 1.961(8) 3_666 ? Li2 Li2 2.656(14) 3_576 ? N2 C12 1.324(5) 2 ? N3 C22 1.334(6) 2_655 ? N3 Li3 2.015(13) . ? O2 Li3 2.037(9) . ? O1 Li1 2.066(8) 2_655 ? O6 Li2 1.877(8) 3_566 ? O7 Li3 2.282(4) . ? O8 Li2 1.932(8) 1_645 ? O8 Li2 1.961(8) 3_666 ? O9 H1 0.850(10) . ? O9 H9 0.850(10) . ? Li3 O2 2.037(9) 2_655 ? Li3 O7 2.282(4) 2_655 ? Li3 Li1 2.632(9) 2_655 ? C23A C24A 1.385(15) . ? C23A C24A 1.520(13) 2_655 ? C24A C24A 0.514(16) 2_655 ? C24A C23A 1.520(13) 2_655 ? 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 O2 C1 O1 125.3(4) . . ? O2 C1 C2 118.7(4) . . ? O1 C1 C2 116.1(4) . . ? N1 C2 C3 121.8(4) . . ? N1 C2 C1 115.0(4) . . ? C3 C2 C1 123.3(4) . . ? C2 C3 C4 118.4(4) . . ? C2 C3 H3 120.8 . . ? C4 C3 H3 120.8 . . ? C5 C4 C3 119.4(5) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C4 C5 C6 119.1(4) . . ? C4 C5 H5 120.5 . . ? C6 C5 H5 120.5 . . ? N1 C6 C5 121.5(4) . . ? N1 C6 C7 115.8(4) . . ? C5 C6 C7 122.6(4) . . ? O4 C7 O3 125.6(4) . . ? O4 C7 C6 117.3(4) . . ? O3 C7 C6 117.2(4) . . ? O6 C11 O5 124.7(4) . . ? O6 C11 C12 118.4(4) . . ? O5 C11 C12 116.9(4) . . ? N2 C12 C13 121.8(4) . . ? N2 C12 C11 116.0(4) . . ? C13 C12 C11 122.2(4) . . ? C14 C13 C12 117.7(4) . . ? C14 C13 H13 121.2 . . ? C12 C13 H13 121.2 . . ? C13 C14 C13 120.5(6) . 2 ? C13 C14 H14 119.7 . . ? C13 C14 H14 119.7 2 . ? O8 C21 O7 125.9(4) . . ? O8 C21 C22 118.1(4) . . ? O7 C21 C22 116.1(4) . . ? N3 C22 C23A 122.7(5) . . ? N3 C22 C23B 120.8(6) . . ? C23A C22 C23B 18.8(5) . . ? N3 C22 C21 115.1(4) . . ? C23A C22 C21 121.3(5) . . ? C23B C22 C21 123.0(5) . . ? O3 Bi1 O3 87.23(15) 2 . ? O3 Bi1 O5 78.67(11) 2 2 ? O3 Bi1 O5 144.84(10) . 2 ? O3 Bi1 O5 144.84(10) 2 . ? O3 Bi1 O5 78.67(11) . . ? O5 Bi1 O5 129.20(14) 2 . ? O3 Bi1 N1 73.90(11) 2 . ? O3 Bi1 N1 65.80(11) . . ? O5 Bi1 N1 137.20(10) 2 . ? O5 Bi1 N1 70.94(11) . . ? O3 Bi1 N1 65.80(11) 2 2 ? O3 Bi1 N1 73.90(11) . 2 ? O5 Bi1 N1 70.94(11) 2 2 ? O5 Bi1 N1 137.20(10) . 2 ? N1 Bi1 N1 123.33(16) . 2 ? O3 Bi1 N2 136.38(7) 2 . ? O3 Bi1 N2 136.38(7) . . ? O5 Bi1 N2 64.60(7) 2 . ? O5 Bi1 N2 64.60(7) . . ? N1 Bi1 N2 118.33(8) . . ? N1 Bi1 N2 118.33(8) 2 . ? O3 Bi1 O1 128.58(9) 2 2 ? O3 Bi1 O1 76.53(10) . 2 ? O5 Bi1 O1 87.36(10) 2 2 ? O5 Bi1 O1 79.31(10) . 2 ? N1 Bi1 O1 135.43(10) . 2 ? N1 Bi1 O1 62.85(10) 2 2 ? N2 Bi1 O1 74.35(6) . 2 ? O3 Bi1 O1 76.53(10) 2 . ? O3 Bi1 O1 128.58(9) . . ? O5 Bi1 O1 79.31(10) 2 . ? O5 Bi1 O1 87.36(10) . . ? N1 Bi1 O1 62.85(10) . . ? N1 Bi1 O1 135.43(10) 2 . ? N2 Bi1 O1 74.35(6) . . ? O1 Bi1 O1 148.69(13) 2 . ? O7 Li1 O9 145.0(4) . . ? O7 Li1 O2 94.5(3) . . ? O9 Li1 O2 109.0(4) . . ? O7 Li1 O1 100.2(3) . 2_655 ? O9 Li1 O1 100.0(4) . 2_655 ? O2 Li1 O1 101.6(3) . 2_655 ? O7 Li1 Li3 57.8(3) . . ? O9 Li1 Li3 155.8(4) . . ? O2 Li1 Li3 49.8(2) . . ? O1 Li1 Li3 76.7(3) 2_655 . ? O7 Li1 H1 150.8(15) . . ? O9 Li1 H1 20.6(9) . . ? O2 Li1 H1 114.4(15) . . ? O1 Li1 H1 79.5(10) 2_655 . ? Li3 Li1 H1 146.7(13) . . ? O4 Li2 O6 114.1(4) . 3_566 ? O4 Li2 O8 113.7(4) . 1_465 ? O6 Li2 O8 113.7(4) 3_566 1_465 ? O4 Li2 O8 104.6(4) . 3_666 ? O6 Li2 O8 114.8(4) 3_566 3_666 ? O8 Li2 O8 93.9(3) 1_465 3_666 ? O4 Li2 Li2 118.6(5) . 3_576 ? O6 Li2 Li2 127.0(5) 3_566 3_576 ? O8 Li2 Li2 47.4(2) 1_465 3_576 ? O8 Li2 Li2 46.5(2) 3_666 3_576 ? C2 N1 C6 119.8(4) . . ? C2 N1 Bi1 122.4(3) . . ? C6 N1 Bi1 117.7(3) . . ? C12 N2 C12 120.3(5) 2 . ? C12 N2 Bi1 119.9(2) 2 . ? C12 N2 Bi1 119.9(2) . . ? C22 N3 C22 119.9(5) 2_655 . ? C22 N3 Li3 120.0(3) 2_655 . ? C22 N3 Li3 120.0(3) . . ? C1 O2 Li1 154.7(4) . . ? C1 O2 Li3 114.9(3) . . ? Li1 O2 Li3 80.7(2) . . ? C1 O1 Li1 117.0(3) . 2_655 ? C1 O1 Bi1 118.8(2) . . ? Li1 O1 Bi1 121.7(2) 2_655 . ? C7 O3 Bi1 121.9(3) . . ? C7 O4 Li2 148.6(4) . . ? C11 O5 Bi1 122.6(3) . . ? C11 O6 Li2 129.2(4) . 3_566 ? C21 O7 Li1 168.3(4) . . ? C21 O7 Li3 113.3(4) . . ? Li1 O7 Li3 77.5(4) . . ? C21 O8 Li2 147.6(4) . 1_645 ? C21 O8 Li2 126.3(3) . 3_666 ? Li2 O8 Li2 86.1(3) 1_645 3_666 ? Li1 O9 H1 107(4) . . ? Li1 O9 H9 139(4) . . ? H1 O9 H9 113(6) . . ? N3 Li3 O2 136.5(2) . . ? N3 Li3 O2 136.5(2) . 2_655 ? O2 Li3 O2 87.0(5) . 2_655 ? N3 Li3 O7 75.4(3) . 2_655 ? O2 Li3 O7 118.6(3) . 2_655 ? O2 Li3 O7 83.51(16) 2_655 2_655 ? N3 Li3 O7 75.4(3) . . ? O2 Li3 O7 83.51(16) . . ? O2 Li3 O7 118.6(3) 2_655 . ? O7 Li3 O7 150.8(6) 2_655 . ? N3 Li3 Li1 120.0(3) . . ? O2 Li3 Li1 49.5(2) . . ? O2 Li3 Li1 85.6(4) 2_655 . ? O7 Li3 Li1 164.4(5) 2_655 . ? O7 Li3 Li1 44.69(19) . . ? N3 Li3 Li1 120.0(3) . 2_655 ? O2 Li3 Li1 85.6(4) . 2_655 ? O2 Li3 Li1 49.5(2) 2_655 2_655 ? O7 Li3 Li1 44.69(19) 2_655 2_655 ? O7 Li3 Li1 164.4(5) . 2_655 ? Li1 Li3 Li1 119.9(5) . 2_655 ? C24A C23A C22 116.6(8) . . ? C24A C23A C24A 19.7(7) . 2_655 ? C22 C23A C24A 110.5(7) . 2_655 ? C24A C24A C23A 95(2) 2_655 . ? C24A C24A C23A 65(2) 2_655 2_655 ? C23A C24A C23A 119.1(9) . 2_655 ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.39 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 1.106 _refine_diff_density_min -1.906 _refine_diff_density_rms 0.141 #===END