data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Jain, Vimal K.' _publ_contact_author_email jainvk@barc.gov.in _publ_section_title ; 2-Pyridyl selenolates of antimony and bismuth: Synthesis, characterization, structures and their use as single source molecular precursor for the preparation of metal selenide nanostructures and thin films ; _publ_author_name V.K.Jain # Attachment '- GK-19a.cif' data_[Sb{Se-C5H3(Me-3)N}3] _database_code_depnum_ccdc_archive 'CCDC 765903' #TrackingRef '- GK-19a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 N3 O2 Sb Se3' _chemical_formula_weight 666.98 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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 14.853(3) _cell_length_b 11.604(2) _cell_length_c 14.490(2) _cell_angle_alpha 90.00 _cell_angle_beta 113.709(13) _cell_angle_gamma 90.00 _cell_volume 2286.6(7) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.1 _cell_measurement_theta_max 13.1 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.937 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 5.999 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.3800 _exptl_absorpt_correction_T_max 0.5853 _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC7S' _diffrn_measurement_method \w-2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% -10.98 _diffrn_reflns_number 6292 _diffrn_reflns_av_R_equivalents 0.0867 _diffrn_reflns_av_sigmaI/netI 0.1274 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5247 _reflns_number_gt 2794 _reflns_threshold_expression >2sigma(I) _computing_data_collection WinAFC _computing_cell_refinement WinAFC _computing_data_reduction CrystalStructure _computing_structure_solution SIR-92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep 3 for windows' _computing_publication_material 'WinGX 1.70.01' _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^)+(0.0503P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0011(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5247 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1333 _refine_ls_R_factor_gt 0.0500 _refine_ls_wR_factor_ref 0.1340 _refine_ls_wR_factor_gt 0.1068 _refine_ls_goodness_of_fit_ref 0.993 _refine_ls_restrained_S_all 0.993 _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 Sb1 Sb 0.34514(4) 0.03319(4) 0.39482(4) 0.04246(17) Uani 1 1 d . . . Se3 Se 0.34294(7) -0.19171(7) 0.42407(7) 0.0530(2) Uani 1 1 d . . . Se2 Se 0.41081(6) 0.03908(6) 0.59505(6) 0.0503(2) Uani 1 1 d . . . Se1 Se 0.16499(7) 0.05774(8) 0.37378(8) 0.0622(3) Uani 1 1 d . . . O1 O 0.0064(15) 0.014(3) 0.027(2) 0.187(8) Uani 1 1 d . . . N2 N 0.3725(5) 0.2405(5) 0.4878(5) 0.0498(16) Uani 1 1 d . . . C8 C 0.4427(5) 0.2758(6) 0.6661(6) 0.0452(18) Uani 1 1 d . . . N3 N 0.2767(5) -0.0993(5) 0.2346(5) 0.0491(16) Uani 1 1 d . . . N1 N 0.2102(5) 0.1869(6) 0.2382(6) 0.0567(18) Uani 1 1 d . . . C18 C 0.2893(7) -0.4195(6) 0.2821(8) 0.070(3) Uani 1 1 d . . . H18A H 0.2708 -0.4815 0.2342 0.104 Uiso 1 1 calc R . . H18B H 0.2512 -0.4236 0.3221 0.104 Uiso 1 1 calc R . . H18C H 0.3579 -0.4259 0.3252 0.104 Uiso 1 1 calc R . . C9 C 0.4354(6) 0.3924(7) 0.6448(7) 0.060(2) Uani 1 1 d . . . H9 H 0.4555 0.4448 0.6978 0.072 Uiso 1 1 calc R . . O2 O -0.1026(7) -0.0626(9) 0.0903(7) 0.149(4) Uani 1 1 d . . . C10 C 0.3991(7) 0.4334(7) 0.5471(8) 0.069(3) Uani 1 1 d . . . H10 H 0.3958 0.5121 0.5342 0.082 Uiso 1 1 calc R . . C14 C 0.2707(6) -0.3071(6) 0.2276(7) 0.050(2) Uani 1 1 d . . . C7 C 0.4092(5) 0.2026(6) 0.5823(6) 0.0431(17) Uani 1 1 d . . . C13 C 0.2923(6) -0.2016(6) 0.2817(6) 0.0480(19) Uani 1 1 d . . . C1 C 0.1395(6) 0.1704(7) 0.2704(7) 0.054(2) Uani 1 1 d . . . C17 C 0.2396(6) -0.0945(8) 0.1352(7) 0.063(3) Uani 1 1 d . . . H17 H 0.2278 -0.0230 0.1035 0.076 Uiso 1 1 calc R . . C12 C 0.4821(6) 0.2315(7) 0.7731(7) 0.061(2) Uani 1 1 d . . . H12A H 0.5448 0.1954 0.7890 0.092 Uiso 1 1 calc R . . H12B H 0.4370 0.1762 0.7798 0.092 Uiso 1 1 calc R . . H12C H 0.4897 0.2945 0.8184 0.092 Uiso 1 1 calc R . . C5 C 0.1939(7) 0.2629(8) 0.1641(8) 0.073(3) Uani 1 1 d . . . H5 H 0.2428 0.2736 0.1402 0.087 Uiso 1 1 calc R . . C4 C 0.1082(8) 0.3267(8) 0.1208(8) 0.079(3) Uani 1 1 d . . . H4 H 0.1005 0.3790 0.0695 0.095 Uiso 1 1 calc R . . C11 C 0.3680(6) 0.3556(7) 0.4699(7) 0.059(2) Uani 1 1 d . . . H11 H 0.3434 0.3821 0.4038 0.071 Uiso 1 1 calc R . . C2 C 0.0472(7) 0.2295(8) 0.2286(9) 0.075(3) Uani 1 1 d . . . C3 C 0.0356(8) 0.3119(10) 0.1541(10) 0.096(4) Uani 1 1 d . . . H3 H -0.0214 0.3561 0.1277 0.115 Uiso 1 1 calc R . . C16 C 0.2181(7) -0.1930(8) 0.0772(8) 0.070(3) Uani 1 1 d . . . H16 H 0.1941 -0.1886 0.0073 0.084 Uiso 1 1 calc R . . C15 C 0.2329(7) -0.2976(8) 0.1248(7) 0.066(2) Uani 1 1 d . . . H15 H 0.2167 -0.3644 0.0860 0.079 Uiso 1 1 calc R . . C6 C -0.0314(9) 0.2030(12) 0.2686(13) 0.159(8) Uani 1 1 d . . . H6A H -0.0325 0.1216 0.2802 0.238 Uiso 1 1 calc R . . H6B H -0.0945 0.2269 0.2199 0.238 Uiso 1 1 calc R . . H6C H -0.0166 0.2437 0.3306 0.238 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Sb1 0.0435(3) 0.0376(3) 0.0476(3) 0.0021(2) 0.0197(2) -0.0001(2) Se3 0.0704(6) 0.0389(4) 0.0536(5) 0.0030(4) 0.0289(4) -0.0023(4) Se2 0.0595(5) 0.0397(4) 0.0482(5) 0.0046(4) 0.0180(4) -0.0001(4) Se1 0.0477(5) 0.0719(6) 0.0734(6) 0.0112(5) 0.0310(5) 0.0003(4) O1 0.039(6) 0.209(15) 0.23(3) -0.124(13) -0.029(10) 0.039(8) N2 0.062(5) 0.041(3) 0.044(4) 0.003(3) 0.018(3) 0.010(3) C8 0.041(5) 0.041(4) 0.051(5) 0.000(4) 0.016(4) 0.003(3) N3 0.059(5) 0.048(4) 0.038(4) 0.005(3) 0.016(3) 0.002(3) N1 0.049(4) 0.063(4) 0.063(5) 0.006(4) 0.028(4) 0.000(4) C18 0.091(7) 0.029(4) 0.100(8) -0.004(4) 0.050(6) 0.006(4) C9 0.057(6) 0.051(5) 0.068(6) -0.017(5) 0.020(5) -0.003(4) O2 0.135(9) 0.200(11) 0.103(8) 0.072(7) 0.038(6) 0.075(7) C10 0.090(8) 0.042(5) 0.079(7) -0.003(5) 0.039(6) -0.001(4) C14 0.045(5) 0.045(4) 0.066(6) -0.009(4) 0.030(4) -0.003(4) C7 0.039(4) 0.053(4) 0.042(4) 0.005(4) 0.022(4) 0.004(3) C13 0.039(5) 0.049(4) 0.055(5) -0.005(4) 0.019(4) -0.006(4) C1 0.041(5) 0.057(5) 0.061(5) -0.005(4) 0.017(4) -0.001(4) C17 0.062(6) 0.059(5) 0.076(7) 0.020(5) 0.035(5) 0.018(5) C12 0.057(6) 0.062(5) 0.060(6) -0.006(4) 0.020(4) -0.003(4) C5 0.061(6) 0.075(6) 0.095(8) 0.010(6) 0.044(6) 0.005(5) C4 0.081(8) 0.075(6) 0.086(8) 0.027(6) 0.038(6) 0.018(6) C11 0.072(7) 0.045(5) 0.061(6) 0.006(4) 0.028(5) 0.005(4) C2 0.040(5) 0.078(7) 0.111(9) 0.018(6) 0.033(6) 0.012(5) C3 0.069(8) 0.094(8) 0.133(11) 0.035(8) 0.049(8) 0.037(6) C16 0.070(7) 0.077(7) 0.063(6) 0.003(5) 0.027(5) 0.018(5) C15 0.068(7) 0.064(6) 0.066(6) -0.009(5) 0.027(5) 0.007(5) C6 0.093(10) 0.193(15) 0.24(2) 0.092(14) 0.123(13) 0.067(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Sb1 Se1 2.5842(11) . ? Sb1 Se3 2.6462(10) . ? Sb1 Se2 2.6641(11) . ? Se3 C13 1.894(8) . ? Se2 C7 1.906(7) . ? Se1 C1 1.908(9) . ? O1 O1 0.79(4) 3 ? N2 C7 1.329(9) . ? N2 C11 1.358(10) . ? C8 C9 1.382(10) . ? C8 C7 1.398(10) . ? C8 C12 1.510(11) . ? N3 C17 1.320(11) . ? N3 C13 1.342(9) . ? N1 C1 1.323(10) . ? N1 C5 1.334(12) . ? C18 C14 1.492(11) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C9 C10 1.381(13) . ? C9 H9 0.9300 . ? C10 C11 1.365(12) . ? C10 H10 0.9300 . ? C14 C15 1.370(12) . ? C14 C13 1.420(10) . ? C1 C2 1.431(11) . ? C17 C16 1.378(12) . ? C17 H17 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C5 C4 1.386(12) . ? C5 H5 0.9300 . ? C4 C3 1.358(14) . ? C4 H4 0.9300 . ? C11 H11 0.9300 . ? C2 C3 1.400(14) . ? C2 C6 1.529(13) . ? C3 H3 0.9300 . ? C16 C15 1.369(13) . ? C16 H16 0.9300 . ? C15 H15 0.9300 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? 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 Se1 Sb1 Se3 92.79(3) . . ? Se1 Sb1 Se2 91.95(4) . . ? Se3 Sb1 Se2 82.74(3) . . ? C13 Se3 Sb1 84.9(2) . . ? C7 Se2 Sb1 86.3(2) . . ? C1 Se1 Sb1 92.2(2) . . ? C7 N2 C11 119.4(7) . . ? C9 C8 C7 115.6(8) . . ? C9 C8 C12 121.7(8) . . ? C7 C8 C12 122.6(7) . . ? C17 N3 C13 120.2(7) . . ? C1 N1 C5 117.8(8) . . ? C14 C18 H18A 109.5 . . ? C14 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C14 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C10 C9 C8 121.9(8) . . ? C10 C9 H9 119.0 . . ? C8 C9 H9 119.0 . . ? C11 C10 C9 118.5(8) . . ? C11 C10 H10 120.8 . . ? C9 C10 H10 120.8 . . ? C15 C14 C13 115.7(8) . . ? C15 C14 C18 123.7(8) . . ? C13 C14 C18 120.6(8) . . ? N2 C7 C8 123.3(7) . . ? N2 C7 Se2 114.4(6) . . ? C8 C7 Se2 122.3(6) . . ? N3 C13 C14 121.8(8) . . ? N3 C13 Se3 114.4(6) . . ? C14 C13 Se3 123.8(6) . . ? N1 C1 C2 122.8(8) . . ? N1 C1 Se1 116.1(6) . . ? C2 C1 Se1 121.0(7) . . ? N3 C17 C16 121.5(8) . . ? N3 C17 H17 119.2 . . ? C16 C17 H17 119.2 . . ? C8 C12 H12A 109.5 . . ? C8 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C8 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N1 C5 C4 123.6(9) . . ? N1 C5 H5 118.2 . . ? C4 C5 H5 118.2 . . ? C3 C4 C5 119.2(10) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? N2 C11 C10 121.3(8) . . ? N2 C11 H11 119.3 . . ? C10 C11 H11 119.3 . . ? C3 C2 C1 117.0(8) . . ? C3 C2 C6 123.6(9) . . ? C1 C2 C6 119.4(10) . . ? C4 C3 C2 119.4(9) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C15 C16 C17 118.5(10) . . ? C15 C16 H16 120.7 . . ? C17 C16 H16 120.7 . . ? C16 C15 C14 122.1(9) . . ? C16 C15 H15 118.9 . . ? C14 C15 H15 118.9 . . ? C2 C6 H6A 109.5 . . ? C2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.985 _refine_diff_density_min -1.316 _refine_diff_density_rms 0.178 # Attachment '- gk-17.cif' data_[Bi{Se-C5H3(Me-3)N}3] _database_code_depnum_ccdc_archive 'CCDC 765904' #TrackingRef '- gk-17.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 Bi N3 O2 Se3' _chemical_formula_weight 754.21 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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/a' _symmetry_space_group_name_Hall '-P 2yab' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 14.590(3) _cell_length_b 11.6058(17) _cell_length_c 14.852(3) _cell_angle_alpha 90.00 _cell_angle_beta 113.745(16) _cell_angle_gamma 90.00 _cell_volume 2302.0(8) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.1 _cell_measurement_theta_max 14.5 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.130 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1360 _exptl_absorpt_coefficient_mu 12.414 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.1474 _exptl_absorpt_correction_T_max 0.4770 _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC7S' _diffrn_measurement_method \w-2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% -2.69 _diffrn_reflns_number 6325 _diffrn_reflns_av_R_equivalents 0.0519 _diffrn_reflns_av_sigmaI/netI 0.2037 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.81 _diffrn_reflns_theta_max 27.54 _reflns_number_total 5283 _reflns_number_gt 2204 _reflns_threshold_expression >2sigma(I) _computing_data_collection WinAFC _computing_cell_refinement WinAFC _computing_data_reduction CrystalStructure _computing_structure_solution SIR92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for windows' _computing_publication_material WinGX-1.70.01' _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^)+(0.0513P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5283 _refine_ls_number_parameters 242 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2031 _refine_ls_R_factor_gt 0.0536 _refine_ls_wR_factor_ref 0.1546 _refine_ls_wR_factor_gt 0.1110 _refine_ls_goodness_of_fit_ref 0.925 _refine_ls_restrained_S_all 0.925 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Bi1 Bi 0.89101(4) 0.52745(5) 0.84464(5) 0.03993(18) Uani 1 1 d . . . Se3 Se 1.09937(11) 0.53495(13) 0.91952(12) 0.0457(4) Uani 1 1 d . . . Se2 Se 0.92051(12) 0.29436(13) 0.84151(14) 0.0507(5) Uani 1 1 d . . . Se1 Se 0.87637(14) 0.55454(16) 0.65990(14) 0.0627(5) Uani 1 1 d . . . N3 N 0.9889(10) 0.7331(11) 0.8748(10) 0.054(4) Uani 1 1 d . . . N2 N 0.7349(9) 0.3916(10) 0.7775(10) 0.050(4) Uani 1 1 d . . . N1 N 0.7425(11) 0.6787(11) 0.7094(10) 0.054(4) Uani 1 1 d . . . C8 C 0.7257(13) 0.1841(13) 0.7675(13) 0.053(4) Uani 1 1 d . . . C6 C 0.7690(18) 0.710(2) 0.4677(17) 0.138(5) Uani 1 1 d . . . H6A H 0.8384 0.7313 0.4931 0.206 Uiso 1 1 calc R . . H6B H 0.7315 0.7574 0.4122 0.206 Uiso 1 1 calc R . . H6C H 0.7621 0.6305 0.4477 0.206 Uiso 1 1 calc R . . C15 C 1.1429(12) 0.8906(13) 0.9362(12) 0.054(5) Uani 1 1 d . . . H15 H 1.1943 0.9446 0.9572 0.065 Uiso 1 1 calc R . . C16 C 1.0440(14) 0.9269(15) 0.8971(14) 0.064(5) Uani 1 1 d . . . H16 H 1.0291 1.0052 0.8896 0.076 Uiso 1 1 calc R . . C17 C 0.9688(12) 0.8482(14) 0.8696(13) 0.055(5) Uani 1 1 d . . . H17 H 0.9028 0.8732 0.8469 0.066 Uiso 1 1 calc R . . C14 C 1.1652(12) 0.7747(13) 0.9443(11) 0.044(4) Uani 1 1 d . . . C11 C 0.6336(13) 0.3952(15) 0.7387(12) 0.058(5) Uani 1 1 d . . . H11 H 0.6028 0.4669 0.7289 0.070 Uiso 1 1 calc R . . C5 C 0.6686(15) 0.7513(16) 0.6968(16) 0.070(5) Uani 1 1 d . . . H5 H 0.6449 0.7575 0.7462 0.084 Uiso 1 1 calc R . . C1 C 0.7741(12) 0.6651(13) 0.6376(11) 0.048(4) Uani 1 1 d . . . C2 C 0.7294(16) 0.7260(19) 0.5474(15) 0.081(6) Uani 1 1 d . . . C18 C 1.2741(11) 0.7299(13) 0.9860(13) 0.057(5) Uani 1 1 d . . . H18A H 1.3195 0.7940 1.0050 0.086 Uiso 1 1 calc R . . H18B H 1.2850 0.6856 0.9365 0.086 Uiso 1 1 calc R . . H18C H 1.2855 0.6821 1.0422 0.086 Uiso 1 1 calc R . . C12 C 0.7794(14) 0.0693(12) 0.7896(15) 0.070(6) Uani 1 1 d . . . H12A H 0.7348 0.0102 0.7510 0.105 Uiso 1 1 calc R . . H12B H 0.8005 0.0519 0.8582 0.105 Uiso 1 1 calc R . . H12C H 0.8368 0.0731 0.7735 0.105 Uiso 1 1 calc R . . C7 C 0.7779(12) 0.2882(12) 0.7907(12) 0.044(4) Uani 1 1 d . . . C3 C 0.6543(17) 0.8073(17) 0.5410(19) 0.103(8) Uani 1 1 d . . . H3 H 0.6256 0.8530 0.4851 0.124 Uiso 1 1 calc R . . C10 C 0.5741(13) 0.2992(17) 0.7130(15) 0.069(6) Uani 1 1 d . . . H10 H 0.5046 0.3049 0.6853 0.083 Uiso 1 1 calc R . . C13 C 1.0856(11) 0.6972(12) 0.9142(10) 0.035(3) Uani 1 1 d . . . C9 C 0.6222(13) 0.1920(16) 0.7303(14) 0.065(5) Uani 1 1 d . . . H9 H 0.5840 0.1250 0.7166 0.078 Uiso 1 1 calc R . . C4 C 0.6248(16) 0.8185(18) 0.6134(16) 0.080(6) Uani 1 1 d . . . H4 H 0.5749 0.8711 0.6086 0.096 Uiso 1 1 calc R . . O1 O 0.4752(19) 0.485(3) 0.497(3) 0.179(6) Uani 1 1 d . . . O2 O 0.4135(12) 0.5644(18) 0.6039(16) 0.177(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi1 0.0434(3) 0.0352(3) 0.0423(3) 0.0003(3) 0.0184(3) -0.0002(3) Se3 0.0434(9) 0.0364(8) 0.0553(11) -0.0006(8) 0.0178(8) 0.0046(7) Se2 0.0514(10) 0.0382(9) 0.0661(13) -0.0025(8) 0.0275(10) 0.0033(7) Se1 0.0746(13) 0.0714(13) 0.0513(12) 0.0015(9) 0.0348(11) 0.0137(9) N3 0.063(10) 0.047(8) 0.049(9) 0.000(7) 0.020(8) -0.015(7) N2 0.035(8) 0.047(8) 0.074(11) -0.008(7) 0.028(8) 0.002(6) N1 0.069(10) 0.052(8) 0.052(10) 0.005(7) 0.037(8) 0.005(7) C8 0.078(13) 0.031(9) 0.058(12) 0.000(8) 0.034(11) -0.003(8) C6 0.160 0.203 0.067(18) 0.037(17) 0.062(15) 0.063(19) C15 0.050(11) 0.045(10) 0.062(13) -0.006(9) 0.018(10) -0.017(8) C16 0.077(13) 0.049(10) 0.075(14) 0.011(9) 0.040(12) 0.006(10) C17 0.042(10) 0.049(10) 0.078(14) 0.015(9) 0.028(10) 0.009(8) C14 0.065(11) 0.050(10) 0.026(9) -0.011(7) 0.029(9) -0.006(8) C11 0.071(13) 0.058(12) 0.048(12) 0.012(9) 0.028(11) 0.012(10) C5 0.077(14) 0.072(13) 0.074(16) 0.009(12) 0.044(13) -0.007(11) C1 0.060(11) 0.056(10) 0.021(9) 0.005(8) 0.011(8) 0.005(8) C2 0.092(16) 0.109(18) 0.042(13) 0.008(11) 0.027(12) -0.014(13) C18 0.054(11) 0.051(10) 0.077(14) -0.001(9) 0.037(10) -0.005(8) C12 0.106(15) 0.029(9) 0.102(17) 0.003(9) 0.069(14) -0.008(9) C7 0.064(11) 0.036(9) 0.046(10) -0.002(7) 0.037(9) 0.008(8) C3 0.12(2) 0.073(16) 0.10(2) 0.038(14) 0.023(17) 0.053(14) C10 0.039(10) 0.076(14) 0.088(16) 0.002(11) 0.022(11) -0.016(10) C13 0.045(9) 0.037(8) 0.024(8) 0.002(6) 0.016(8) -0.002(7) C9 0.062(12) 0.068(13) 0.069(14) -0.006(10) 0.030(11) -0.031(10) C4 0.093(16) 0.081(15) 0.066(16) -0.023(13) 0.033(14) -0.005(12) O1 0.200 0.170 0.110 0.067(12) 0.00(2) -0.103(17) O2 0.102(14) 0.23(2) 0.22(2) 0.101(18) 0.080(16) 0.080(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Bi1 N2 2.616(12) . ? Bi1 Se1 2.683(2) . ? Bi1 N3 2.724(12) . ? Bi1 Se2 2.7426(16) . ? Bi1 Se3 2.7863(17) . ? Se3 C13 1.892(14) . ? Se2 C7 1.908(15) . ? Se1 C1 1.893(16) . ? N3 C13 1.358(17) . ? N3 C17 1.363(19) . ? N2 C7 1.331(16) . ? N2 C11 1.352(19) . ? N1 C5 1.32(2) . ? N1 C1 1.331(18) . ? C8 C9 1.39(2) . ? C8 C7 1.40(2) . ? C8 C12 1.51(2) . ? C6 C2 1.52(3) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C15 C14 1.377(19) . ? C15 C16 1.39(2) . ? C15 H15 0.9300 . ? C16 C17 1.36(2) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C14 C13 1.393(19) . ? C14 C18 1.54(2) . ? C11 C10 1.37(2) . ? C11 H11 0.9300 . ? C5 C4 1.38(3) . ? C5 H5 0.9300 . ? C1 C2 1.42(2) . ? C2 C3 1.42(3) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C3 C4 1.32(3) . ? C3 H3 0.9300 . ? C10 C9 1.40(2) . ? C10 H10 0.9300 . ? C9 H9 0.9300 . ? C4 H4 0.9300 . ? O1 O1 0.78(4) 3_666 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Bi1 Se1 89.0(3) . . ? N2 Bi1 N3 155.4(4) . . ? Se1 Bi1 N3 83.5(3) . . ? N2 Bi1 Se2 61.1(3) . . ? Se1 Bi1 Se2 92.68(6) . . ? N3 Bi1 Se2 142.3(3) . . ? N2 Bi1 Se3 144.5(3) . . ? Se1 Bi1 Se3 91.68(6) . . ? N3 Bi1 Se3 59.4(3) . . ? Se2 Bi1 Se3 83.35(5) . . ? C13 Se3 Bi1 86.2(4) . . ? C7 Se2 Bi1 83.7(4) . . ? C1 Se1 Bi1 89.5(5) . . ? C13 N3 C17 119.2(13) . . ? C13 N3 Bi1 100.8(9) . . ? C17 N3 Bi1 139.7(11) . . ? C7 N2 C11 117.4(14) . . ? C7 N2 Bi1 101.6(9) . . ? C11 N2 Bi1 141.0(11) . . ? C5 N1 C1 119.2(15) . . ? C9 C8 C7 116.0(15) . . ? C9 C8 C12 122.0(15) . . ? C7 C8 C12 121.8(16) . . ? C2 C6 H6A 109.5 . . ? C2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C14 C15 C16 120.2(15) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C17 C16 C15 119.9(16) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 N3 120.9(15) . . ? C16 C17 H17 119.5 . . ? N3 C17 H17 119.5 . . ? C15 C14 C13 117.7(15) . . ? C15 C14 C18 122.2(14) . . ? C13 C14 C18 120.1(13) . . ? N2 C11 C10 123.7(16) . . ? N2 C11 H11 118.1 . . ? C10 C11 H11 118.1 . . ? N1 C5 C4 122.8(19) . . ? N1 C5 H5 118.6 . . ? C4 C5 H5 118.6 . . ? N1 C1 C2 121.4(16) . . ? N1 C1 Se1 116.3(11) . . ? C2 C1 Se1 122.2(14) . . ? C1 C2 C3 116.3(18) . . ? C1 C2 C6 120(2) . . ? C3 C2 C6 124(2) . . ? C14 C18 H18A 109.5 . . ? C14 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C14 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C8 C12 H12A 109.5 . . ? C8 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C8 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N2 C7 C8 124.5(15) . . ? N2 C7 Se2 113.5(11) . . ? C8 C7 Se2 121.9(12) . . ? C4 C3 C2 121(2) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C11 C10 C9 117.2(16) . . ? C11 C10 H10 121.4 . . ? C9 C10 H10 121.4 . . ? N3 C13 C14 121.8(13) . . ? N3 C13 Se3 113.5(10) . . ? C14 C13 Se3 124.7(11) . . ? C8 C9 C10 121.2(15) . . ? C8 C9 H9 119.4 . . ? C10 C9 H9 119.4 . . ? C3 C4 C5 119(2) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.369 _refine_diff_density_min -1.839 _refine_diff_density_rms 0.240