# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Shigeru Shimada' _publ_contact_author_name 'Shigeru Shimada' _publ_contact_author_email S-SHIMADA@AIST.GO.JP _publ_section_title ; A Unique Bi-Bi Bond Forming Reaction Using Organobismuth Oxides and Phosphorus Compounds Bearing a P(=O)H group ; _publ_contact_author_address ; National Institute of Advanced Industrial Science and Technology, Tukuba Central 5, Tsukuba, Ibaraki 305-8565, Japan ; _publ_contact_author_fax +81-29-861-4511 _publ_contact_author_phone +81-29-861-6257 _publ_requested_journal 'Chemical Communications' # Attachment 'Compounds_1a_1b_1c_4_6a.cif' data_compound-1a _database_code_depnum_ccdc_archive 'CCDC 740995' _audit_creation_date 2008-01-13 _audit_creation_method 'by CrystalStructure 3.8' _audit_update_record ? #============================================================================== _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction CrystalStructure _computing_structure_solution 'DIRDIF99 (PATTY)' _computing_structure_refinement CRYSTALS _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C50 H58 Bi2 N2 ' _chemical_formula_moiety 'C36 H42 Bi2 N2, 2(C7 H8) ' _chemical_formula_weight 1104.98 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _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_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 +X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 9.5702(4) _cell_length_b 14.2358(6) _cell_length_c 15.7621(7) _cell_angle_alpha 90.0000 _cell_angle_beta 98.708(1) _cell_angle_gamma 90.0000 _cell_volume 2122.67(16) _cell_formula_units_Z 2 _cell_measurement_reflns_used 6950 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 28.2 _cell_measurement_temperature 153(2) #------------------------------------------------------------------------------ _exptl_crystal_description prismatic _exptl_crystal_colour orange _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.729 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1076.00 _exptl_absorpt_coefficient_mu 8.300 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.456 _exptl_absorpt_correction_T_max 0.517 _exptl_absorpt_process_details ; SADABS; Sheldrick 1996 ; #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean '8.366 [pixels/mm]' _diffrn_ambient_temperature 153(2) _diffrn_reflns_number 12618 _diffrn_reflns_av_R_equivalents 0.021 _diffrn_reflns_theta_max 28.21 _diffrn_measured_fraction_theta_max 0.922 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.967 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 4719 _reflns_number_gt 4103 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0178 _refine_ls_wR_factor_ref 0.0411 _atom_sites_solution_primary heavy _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 4719 _refine_ls_number_parameters 273 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[0.3300\s(Fo^2^) + 0.0800]/(4Fo^2^)' _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 0.73 _refine_diff_density_min -0.51 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Bi Bi -4.108 10.257 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Bi(1) Bi 0.032210(10) 0.081030(10) 0.063970(10) 0.01466(2) Uani 1.00 1 d . . . N(1) N 0.0522(2) 0.16135(17) 0.23402(16) 0.0181(6) Uani 1.00 1 d . . . C(1) C -0.1759(2) 0.0659(2) 0.11639(18) 0.0167(6) Uani 1.00 1 d . . . C(2) C -0.2826(3) 0.0066(2) 0.07785(18) 0.0175(6) Uani 1.00 1 d . . . C(3) C -0.4094(3) -0.0030(2) 0.1098(2) 0.0221(7) Uani 1.00 1 d . . . C(4) C -0.4311(3) 0.0469(2) 0.1817(2) 0.0234(7) Uani 1.00 1 d . . . C(5) C -0.3267(3) 0.1064(2) 0.2207(2) 0.0223(7) Uani 1.00 1 d . . . C(6) C -0.2000(3) 0.1175(2) 0.18864(19) 0.0189(7) Uani 1.00 1 d . . . C(7) C -0.0963(3) 0.1895(2) 0.2318(2) 0.0226(7) Uani 1.00 1 d . . . C(8) C 0.0822(3) 0.0764(2) 0.28645(18) 0.0200(7) Uani 1.00 1 d . . . C(9) C 0.1726(3) 0.0034(2) 0.25039(18) 0.0175(6) Uani 1.00 1 d . . . C(10) C 0.2612(3) -0.0529(2) 0.30747(19) 0.0202(7) Uani 1.00 1 d . . . C(11) C 0.3385(3) -0.1255(2) 0.2790(2) 0.0219(7) Uani 1.00 1 d . . . C(12) C 0.3269(3) -0.1430(2) 0.19195(19) 0.0204(7) Uani 1.00 1 d . . . C(13) C 0.2393(2) -0.0870(2) 0.13410(18) 0.0182(6) Uani 1.00 1 d . . . C(14) C 0.1618(2) -0.0134(2) 0.16221(18) 0.0164(6) Uani 1.00 1 d . . . C(15) C 0.1535(3) 0.2409(2) 0.2592(2) 0.0250(7) Uani 1.00 1 d . . . C(16) C 0.1265(3) 0.3196(2) 0.1921(2) 0.0371(10) Uani 1.00 1 d . . . C(17) C 0.1400(4) 0.2815(2) 0.3477(2) 0.0398(10) Uani 1.00 1 d . . . C(18) C 0.3040(3) 0.2058(2) 0.2584(2) 0.0316(9) Uani 1.00 1 d . . . C(19) C 0.6163(4) 0.1766(2) 0.4851(2) 0.0354(9) Uani 1.00 1 d . . . C(20) C 0.7610(4) 0.1940(2) 0.5007(2) 0.0412(10) Uani 1.00 1 d . . . C(21) C 0.8580(4) 0.1290(3) 0.4808(2) 0.0475(12) Uani 1.00 1 d . . . C(22) C 0.8124(4) 0.0443(3) 0.4450(2) 0.0455(11) Uani 1.00 1 d . . . C(23) C 0.6692(4) 0.0253(2) 0.4291(2) 0.0421(11) Uani 1.00 1 d . . . C(24) C 0.5731(4) 0.0904(2) 0.4483(2) 0.0343(9) Uani 1.00 1 d . . . C(25) C 0.5107(5) 0.2472(3) 0.5059(2) 0.0514(12) Uani 1.00 1 d . . . H(1) H -0.2684 -0.0282 0.0284 0.021 Uiso 1.00 1 c R . . H(2) H -0.4808 -0.0438 0.0823 0.026 Uiso 1.00 1 c R . . H(3) H -0.5172 0.0403 0.2043 0.029 Uiso 1.00 1 c R . . H(4) H -0.3418 0.1406 0.2703 0.027 Uiso 1.00 1 c R . . H(5) H -0.1135 0.1981 0.2891 0.027 Uiso 1.00 1 c R . . H(6) H -0.1113 0.2471 0.2014 0.027 Uiso 1.00 1 c R . . H(7) H 0.1296 0.0949 0.3412 0.024 Uiso 1.00 1 c R . . H(8) H -0.0055 0.0480 0.2926 0.024 Uiso 1.00 1 c R . . H(9) H 0.2689 -0.0412 0.3673 0.024 Uiso 1.00 1 c R . . H(10) H 0.3988 -0.1630 0.3188 0.026 Uiso 1.00 1 c R . . H(11) H 0.3786 -0.1930 0.1717 0.025 Uiso 1.00 1 c R . . H(12) H 0.2322 -0.0992 0.0743 0.022 Uiso 1.00 1 c R . . H(13) H 0.1973 0.3665 0.2043 0.044 Uiso 1.00 1 c R . . H(14) H 0.1293 0.2944 0.1366 0.044 Uiso 1.00 1 c R . . H(15) H 0.0362 0.3466 0.1939 0.044 Uiso 1.00 1 c R . . H(16) H 0.0522 0.3134 0.3448 0.047 Uiso 1.00 1 c R . . H(17) H 0.1443 0.2320 0.3884 0.047 Uiso 1.00 1 c R . . H(18) H 0.2152 0.3243 0.3646 0.048 Uiso 1.00 1 c R . . H(19) H 0.3317 0.1666 0.3068 0.038 Uiso 1.00 1 c R . . H(20) H 0.3075 0.1709 0.2073 0.037 Uiso 1.00 1 c R . . H(21) H 0.3664 0.2579 0.2604 0.038 Uiso 1.00 1 c R . . H(22) H 0.7936 0.2521 0.5258 0.048 Uiso 1.00 1 c R . . H(23) H 0.9561 0.1430 0.4917 0.056 Uiso 1.00 1 c R . . H(24) H 0.8788 -0.0008 0.4315 0.056 Uiso 1.00 1 c R . . H(25) H 0.6369 -0.0333 0.4048 0.051 Uiso 1.00 1 c R . . H(26) H 0.4750 0.0766 0.4362 0.040 Uiso 1.00 1 c R . . H(27) H 0.4654 0.2758 0.4545 0.060 Uiso 1.00 1 c R . . H(28) H 0.4421 0.2168 0.5339 0.060 Uiso 1.00 1 c R . . H(29) H 0.5578 0.2940 0.5426 0.060 Uiso 1.00 1 c 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Bi(1) 0.01294(5) 0.01618(6) 0.01486(5) 0.00134(4) 0.00206(4) 0.00131(4) N(1) 0.0168(11) 0.0165(12) 0.0206(12) -0.0000(9) 0.0014(9) -0.0023(9) C(1) 0.0153(12) 0.0163(14) 0.0187(13) 0.0030(10) 0.0033(10) 0.0034(10) C(2) 0.0175(13) 0.0186(14) 0.0164(13) 0.0010(11) 0.0022(10) -0.0004(11) C(3) 0.0183(14) 0.0190(14) 0.0290(16) -0.0023(11) 0.0033(12) 0.0018(12) C(4) 0.0187(14) 0.0248(15) 0.0284(16) -0.0013(12) 0.0090(12) 0.0034(13) C(5) 0.0232(15) 0.0214(15) 0.0238(15) 0.0034(12) 0.0089(12) -0.0016(12) C(6) 0.0190(14) 0.0171(13) 0.0199(14) 0.0024(11) 0.0011(11) 0.0010(11) C(7) 0.0191(14) 0.0249(15) 0.0241(15) 0.0017(12) 0.0038(11) -0.0073(12) C(8) 0.0223(14) 0.0206(14) 0.0166(13) -0.0008(12) 0.0016(11) -0.0005(11) C(9) 0.0162(13) 0.0166(13) 0.0198(14) -0.0035(11) 0.0026(10) 0.0001(11) C(10) 0.0227(14) 0.0208(14) 0.0164(13) -0.0032(11) 0.0006(11) 0.0033(11) C(11) 0.0212(15) 0.0203(15) 0.0230(15) 0.0001(12) -0.0011(12) 0.0083(12) C(12) 0.0182(14) 0.0174(14) 0.0259(15) 0.0012(11) 0.0042(11) -0.0007(12) C(13) 0.0172(13) 0.0211(14) 0.0166(13) -0.0026(11) 0.0035(10) -0.0017(11) C(14) 0.0119(12) 0.0176(13) 0.0195(13) -0.0019(10) 0.0019(10) 0.0012(11) C(15) 0.0214(14) 0.0180(14) 0.0341(17) -0.0024(12) -0.0012(12) -0.0064(13) C(16) 0.0299(18) 0.0192(16) 0.061(2) -0.0049(14) 0.0032(17) 0.0044(16) C(17) 0.0344(19) 0.036(2) 0.048(2) -0.0032(16) 0.0029(16) -0.0258(17) C(18) 0.0179(15) 0.0284(17) 0.047(2) -0.0034(13) 0.0006(14) -0.0043(15) C(19) 0.049(2) 0.0329(19) 0.0222(16) -0.0062(16) -0.0001(15) 0.0086(14) C(20) 0.060(2) 0.034(2) 0.0262(17) -0.0229(19) -0.0043(17) 0.0062(15) C(21) 0.042(2) 0.064(2) 0.036(2) -0.014(2) 0.0015(17) 0.014(2) C(22) 0.056(2) 0.054(2) 0.0280(19) 0.000(2) 0.0140(18) 0.0058(18) C(23) 0.061(2) 0.039(2) 0.0268(18) -0.0103(19) 0.0064(17) -0.0007(16) C(24) 0.0383(19) 0.037(2) 0.0262(16) -0.0105(16) -0.0012(14) 0.0057(15) C(25) 0.071(2) 0.040(2) 0.040(2) 0.010(2) -0.003(2) 0.0094(19) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 Bi(1) Bi(1) 3.0648(2) yes . 3_555 Bi(1) N(1) 2.894(2) yes . . Bi(1) C(1) 2.279(2) yes . . Bi(1) C(14) 2.272(2) yes . . N(1) C(7) 1.472(3) yes . . N(1) C(8) 1.469(3) yes . . N(1) C(15) 1.504(3) yes . . C(1) C(2) 1.391(3) yes . . C(1) C(6) 1.404(4) yes . . C(2) C(3) 1.389(4) yes . . C(3) C(4) 1.380(4) yes . . C(4) C(5) 1.381(4) yes . . C(5) C(6) 1.391(4) yes . . C(6) C(7) 1.513(4) yes . . C(8) C(9) 1.516(4) yes . . C(9) C(10) 1.393(3) yes . . C(9) C(14) 1.399(4) yes . . C(10) C(11) 1.384(4) yes . . C(11) C(12) 1.382(4) yes . . C(12) C(13) 1.392(3) yes . . C(13) C(14) 1.394(4) yes . . C(15) C(16) 1.535(4) yes . . C(15) C(17) 1.532(5) yes . . C(15) C(18) 1.527(4) yes . . C(19) C(20) 1.391(5) yes . . C(19) C(24) 1.393(5) yes . . C(19) C(25) 1.496(6) yes . . C(20) C(21) 1.379(6) yes . . C(21) C(22) 1.374(6) yes . . C(22) C(23) 1.382(6) yes . . C(23) C(24) 1.371(5) yes . . C(2) H(1) 0.950 no . . C(3) H(2) 0.950 no . . C(4) H(3) 0.950 no . . C(5) H(4) 0.950 no . . C(7) H(5) 0.950 no . . C(7) H(6) 0.950 no . . C(8) H(7) 0.950 no . . C(8) H(8) 0.950 no . . C(10) H(9) 0.950 no . . C(11) H(10) 0.950 no . . C(12) H(11) 0.950 no . . C(13) H(12) 0.950 no . . C(16) H(13) 0.950 no . . C(16) H(14) 0.950 no . . C(16) H(15) 0.950 no . . C(17) H(16) 0.950 no . . C(17) H(17) 0.950 no . . C(17) H(18) 0.950 no . . C(18) H(19) 0.950 no . . C(18) H(20) 0.950 no . . C(18) H(21) 0.950 no . . C(20) H(22) 0.950 no . . C(21) H(23) 0.950 no . . C(22) H(24) 0.950 no . . C(23) H(25) 0.950 no . . C(24) H(26) 0.950 no . . C(25) H(27) 0.950 no . . C(25) H(28) 0.950 no . . C(25) H(29) 0.950 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 Bi(1) Bi(1) N(1) 152.31(4) yes 3_555 . . Bi(1) Bi(1) C(1) 93.87(7) yes 3_555 . . Bi(1) Bi(1) C(14) 92.18(7) yes 3_555 . . N(1) Bi(1) C(1) 68.94(8) yes . . . N(1) Bi(1) C(14) 69.48(8) yes . . . C(1) Bi(1) C(14) 96.54(10) yes . . . Bi(1) N(1) C(7) 99.02(16) yes . . . Bi(1) N(1) C(8) 100.12(16) yes . . . Bi(1) N(1) C(15) 119.46(18) yes . . . C(7) N(1) C(8) 110.1(2) yes . . . C(7) N(1) C(15) 112.5(2) yes . . . C(8) N(1) C(15) 114.1(2) yes . . . Bi(1) C(1) C(2) 121.5(2) yes . . . Bi(1) C(1) C(6) 120.28(19) yes . . . C(2) C(1) C(6) 118.2(2) yes . . . C(1) C(2) C(3) 121.7(2) yes . . . C(2) C(3) C(4) 119.7(2) yes . . . C(3) C(4) C(5) 119.5(3) yes . . . C(4) C(5) C(6) 121.4(2) yes . . . C(1) C(6) C(5) 119.6(2) yes . . . C(1) C(6) C(7) 122.8(2) yes . . . C(5) C(6) C(7) 117.5(2) yes . . . N(1) C(7) C(6) 113.1(2) yes . . . N(1) C(8) C(9) 115.3(2) yes . . . C(8) C(9) C(10) 118.6(2) yes . . . C(8) C(9) C(14) 121.9(2) yes . . . C(10) C(9) C(14) 119.3(2) yes . . . C(9) C(10) C(11) 121.5(2) yes . . . C(10) C(11) C(12) 119.3(2) yes . . . C(11) C(12) C(13) 119.8(2) yes . . . C(12) C(13) C(14) 121.2(2) yes . . . Bi(1) C(14) C(9) 121.8(2) yes . . . Bi(1) C(14) C(13) 119.33(19) yes . . . C(9) C(14) C(13) 118.8(2) yes . . . N(1) C(15) C(16) 109.5(2) yes . . . N(1) C(15) C(17) 112.6(2) yes . . . N(1) C(15) C(18) 108.7(2) yes . . . C(16) C(15) C(17) 108.9(2) yes . . . C(16) C(15) C(18) 107.0(2) yes . . . C(17) C(15) C(18) 109.9(2) yes . . . C(20) C(19) C(24) 117.0(3) yes . . . C(20) C(19) C(25) 121.9(3) yes . . . C(24) C(19) C(25) 121.0(3) yes . . . C(19) C(20) C(21) 121.8(3) yes . . . C(20) C(21) C(22) 119.9(4) yes . . . C(21) C(22) C(23) 119.4(4) yes . . . C(22) C(23) C(24) 120.5(3) yes . . . C(19) C(24) C(23) 121.4(3) yes . . . C(1) C(2) H(1) 119.2 no . . . C(3) C(2) H(1) 119.2 no . . . C(2) C(3) H(2) 120.1 no . . . C(4) C(3) H(2) 120.1 no . . . C(3) C(4) H(3) 120.2 no . . . C(5) C(4) H(3) 120.3 no . . . C(4) C(5) H(4) 119.3 no . . . C(6) C(5) H(4) 119.3 no . . . N(1) C(7) H(5) 108.5 no . . . N(1) C(7) H(6) 108.6 no . . . C(6) C(7) H(5) 108.6 no . . . C(6) C(7) H(6) 108.6 no . . . H(5) C(7) H(6) 109.5 no . . . N(1) C(8) H(7) 108.0 no . . . N(1) C(8) H(8) 108.0 no . . . C(9) C(8) H(7) 108.0 no . . . C(9) C(8) H(8) 108.0 no . . . H(7) C(8) H(8) 109.5 no . . . C(9) C(10) H(9) 119.3 no . . . C(11) C(10) H(9) 119.2 no . . . C(10) C(11) H(10) 120.4 no . . . C(12) C(11) H(10) 120.3 no . . . C(11) C(12) H(11) 120.1 no . . . C(13) C(12) H(11) 120.1 no . . . C(12) C(13) H(12) 119.4 no . . . C(14) C(13) H(12) 119.4 no . . . C(15) C(16) H(13) 109.5 no . . . C(15) C(16) H(14) 109.5 no . . . C(15) C(16) H(15) 109.4 no . . . H(13) C(16) H(14) 109.5 no . . . H(13) C(16) H(15) 109.5 no . . . H(14) C(16) H(15) 109.5 no . . . C(15) C(17) H(16) 109.4 no . . . C(15) C(17) H(17) 109.6 no . . . C(15) C(17) H(18) 109.5 no . . . H(16) C(17) H(17) 109.5 no . . . H(16) C(17) H(18) 109.5 no . . . H(17) C(17) H(18) 109.5 no . . . C(15) C(18) H(19) 109.5 no . . . C(15) C(18) H(20) 109.5 no . . . C(15) C(18) H(21) 109.4 no . . . H(19) C(18) H(20) 109.5 no . . . H(19) C(18) H(21) 109.5 no . . . H(20) C(18) H(21) 109.5 no . . . C(19) C(20) H(22) 118.9 no . . . C(21) C(20) H(22) 119.3 no . . . C(20) C(21) H(23) 120.0 no . . . C(22) C(21) H(23) 120.1 no . . . C(21) C(22) H(24) 120.3 no . . . C(23) C(22) H(24) 120.3 no . . . C(22) C(23) H(25) 119.9 no . . . C(24) C(23) H(25) 119.6 no . . . C(19) C(24) H(26) 119.1 no . . . C(23) C(24) H(26) 119.5 no . . . C(19) C(25) H(27) 109.7 no . . . C(19) C(25) H(28) 109.5 no . . . C(19) C(25) H(29) 109.3 no . . . H(27) C(25) H(28) 109.5 no . . . H(27) C(25) H(29) 109.5 no . . . H(28) C(25) H(29) 109.5 no . . . #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== data_compound-1b _database_code_depnum_ccdc_archive 'CCDC 740996' _audit_creation_date 2007-12-11 _audit_creation_method 'by CrystalStructure 3.8' _audit_update_record ? #============================================================================== _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction CrystalStructure _computing_structure_solution 'DIRDIF99 (PATTY)' _computing_structure_refinement CRYSTALS _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C56 H70 Bi2 N2 ' _chemical_formula_moiety 'C44 H58 Bi2 N2, 2(C6 H6) ' _chemical_formula_weight 1189.14 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2-X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 1/2+X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 12.5428(5) _cell_length_b 15.0866(6) _cell_length_c 12.9830(5) _cell_angle_alpha 90.0000 _cell_angle_beta 92.749(1) _cell_angle_gamma 90.0000 _cell_volume 2453.92(17) _cell_formula_units_Z 2 _cell_measurement_reflns_used 8013 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 28.1 _cell_measurement_temperature 153(2) #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour orange-red _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.609 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1172.00 _exptl_absorpt_coefficient_mu 7.186 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.336 _exptl_absorpt_correction_T_max 0.561 _exptl_absorpt_process_details ; SADABS; Sheldrick 1996 ; #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean '8.366 [pixels/mm]' _diffrn_ambient_temperature 153(2) _diffrn_reflns_number 14654 _diffrn_reflns_av_R_equivalents 0.020 _diffrn_reflns_theta_max 28.29 _diffrn_measured_fraction_theta_max 0.918 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.973 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 16 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 5473 _reflns_number_gt 4719 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0184 _refine_ls_wR_factor_ref 0.0443 _atom_sites_solution_primary heavy _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 5473 _refine_ls_number_parameters 306 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[0.1000\s(Fo^2^) + 0.0500]/(4Fo^2^)' _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 0.90 _refine_diff_density_min -0.64 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Bi Bi -4.108 10.257 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Bi(1) Bi 0.093740(10) 0.041220(10) 0.446350(10) 0.02143(2) Uani 1.00 1 d . . . N(1) N 0.27701(19) 0.03449(15) 0.31442(18) 0.0226(5) Uani 1.00 1 d . . . C(1) C 0.2117(2) -0.06553(19) 0.5012(2) 0.0241(6) Uani 1.00 1 d . . . C(2) C 0.1843(2) -0.1314(2) 0.5708(2) 0.0270(7) Uani 1.00 1 d . . . C(3) C 0.2575(2) -0.1947(2) 0.6062(2) 0.0312(8) Uani 1.00 1 d . . . C(4) C 0.3593(2) -0.1942(2) 0.5704(2) 0.0322(8) Uani 1.00 1 d . . . C(5) C 0.3875(2) -0.1299(2) 0.5005(2) 0.0282(7) Uani 1.00 1 d . . . C(6) C 0.3159(2) -0.06414(19) 0.4668(2) 0.0241(6) Uani 1.00 1 d . . . C(7) C 0.3561(2) 0.0073(2) 0.3965(2) 0.0272(7) Uani 1.00 1 d . . . C(8) C 0.2427(2) -0.04114(19) 0.2488(2) 0.0245(6) Uani 1.00 1 d . . . C(9) C 0.1241(2) -0.04411(19) 0.2212(2) 0.0247(6) Uani 1.00 1 d . . . C(10) C 0.0907(2) -0.0746(2) 0.1236(2) 0.0315(8) Uani 1.00 1 d . . . C(11) C -0.0167(3) -0.0827(2) 0.0940(2) 0.0369(8) Uani 1.00 1 d . . . C(12) C -0.0929(2) -0.0603(2) 0.1632(2) 0.0362(8) Uani 1.00 1 d . . . C(13) C -0.0604(2) -0.0297(2) 0.2609(2) 0.0301(7) Uani 1.00 1 d . . . C(14) C 0.0472(2) -0.02112(19) 0.2910(2) 0.0251(7) Uani 1.00 1 d . . . C(15) C 0.3116(2) 0.1158(2) 0.2557(2) 0.0274(7) Uani 1.00 1 d . . . C(16) C 0.3150(2) 0.1943(2) 0.3310(2) 0.0326(8) Uani 1.00 1 d . . . C(17) C 0.2241(2) 0.1352(2) 0.1725(2) 0.0352(8) Uani 1.00 1 d . . . C(18) C 0.4227(2) 0.0986(2) 0.2129(2) 0.0279(7) Uani 1.00 1 d . . . C(19) C 0.4710(3) 0.1541(2) 0.1259(2) 0.0358(8) Uani 1.00 1 d . . . C(20) C 0.5885(3) 0.1239(2) 0.1234(3) 0.0488(11) Uani 1.00 1 d . . . C(21) C 0.4695(3) 0.2540(2) 0.1459(2) 0.0449(10) Uani 1.00 1 d . . . C(22) C 0.4182(3) 0.1352(2) 0.0201(2) 0.0506(11) Uani 1.00 1 d . . . C(23) C 0.9395(3) 0.2144(2) 0.1817(3) 0.0465(10) Uani 1.00 1 d . . . C(24) C 0.9857(3) 0.2780(2) 0.2441(3) 0.0473(11) Uani 1.00 1 d . . . C(25) C 0.9427(3) 0.3619(2) 0.2450(3) 0.0534(12) Uani 1.00 1 d . . . C(26) C 0.8546(4) 0.3819(3) 0.1836(3) 0.0640(14) Uani 1.00 1 d . . . C(27) C 0.8090(3) 0.3180(4) 0.1225(3) 0.0722(16) Uani 1.00 1 d . . . C(28) C 0.8515(3) 0.2351(3) 0.1213(3) 0.0585(13) Uani 1.00 1 d . . . H(1) H 0.1131 -0.1329 0.5947 0.032 Uiso 1.00 1 c R . . H(2) H 0.2375 -0.2383 0.6555 0.037 Uiso 1.00 1 c R . . H(3) H 0.4103 -0.2382 0.5938 0.038 Uiso 1.00 1 c R . . H(4) H 0.4580 -0.1303 0.4748 0.034 Uiso 1.00 1 c R . . H(5) H 0.4201 -0.0156 0.3634 0.033 Uiso 1.00 1 c R . . H(6) H 0.3759 0.0599 0.4388 0.033 Uiso 1.00 1 c R . . H(7) H 0.2809 -0.0375 0.1840 0.029 Uiso 1.00 1 c R . . H(8) H 0.2630 -0.0966 0.2855 0.030 Uiso 1.00 1 c R . . H(9) H 0.1434 -0.0904 0.0756 0.038 Uiso 1.00 1 c R . . H(10) H -0.0379 -0.1035 0.0262 0.044 Uiso 1.00 1 c R . . H(11) H -0.1674 -0.0658 0.1439 0.043 Uiso 1.00 1 c R . . H(12) H -0.1134 -0.0141 0.3087 0.036 Uiso 1.00 1 c R . . H(13) H 0.3748 0.1866 0.3816 0.039 Uiso 1.00 1 c R . . H(14) H 0.3244 0.2496 0.2928 0.039 Uiso 1.00 1 c R . . H(15) H 0.2480 0.1969 0.3668 0.040 Uiso 1.00 1 c R . . H(16) H 0.2253 0.0894 0.1190 0.042 Uiso 1.00 1 c R . . H(17) H 0.1544 0.1350 0.2035 0.042 Uiso 1.00 1 c R . . H(18) H 0.2366 0.1933 0.1416 0.042 Uiso 1.00 1 c R . . H(19) H 0.4742 0.1030 0.2729 0.034 Uiso 1.00 1 c R . . H(20) H 0.4206 0.0368 0.1872 0.034 Uiso 1.00 1 c R . . H(21) H 0.6288 0.1470 0.1841 0.059 Uiso 1.00 1 c R . . H(22) H 0.5917 0.0590 0.1235 0.059 Uiso 1.00 1 c R . . H(23) H 0.6195 0.1466 0.0607 0.060 Uiso 1.00 1 c R . . H(24) H 0.3955 0.2751 0.1404 0.054 Uiso 1.00 1 c R . . H(25) H 0.5002 0.2664 0.2152 0.054 Uiso 1.00 1 c R . . H(26) H 0.5112 0.2845 0.0947 0.054 Uiso 1.00 1 c R . . H(27) H 0.4258 0.0721 0.0039 0.061 Uiso 1.00 1 c R . . H(28) H 0.3423 0.1504 0.0207 0.061 Uiso 1.00 1 c R . . H(29) H 0.4522 0.1708 -0.0322 0.061 Uiso 1.00 1 c R . . H(30) H 0.9690 0.1557 0.1807 0.056 Uiso 1.00 1 c R . . H(31) H 1.0478 0.2640 0.2872 0.057 Uiso 1.00 1 c R . . H(32) H 0.9751 0.4066 0.2888 0.065 Uiso 1.00 1 c R . . H(33) H 0.8248 0.4405 0.1835 0.078 Uiso 1.00 1 c R . . H(34) H 0.7463 0.3312 0.0800 0.087 Uiso 1.00 1 c R . . H(35) H 0.8190 0.1907 0.0771 0.070 Uiso 1.00 1 c 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Bi(1) 0.02216(6) 0.01953(5) 0.02260(6) 0.00069(4) 0.00117(4) -0.00085(4) N(1) 0.0256(11) 0.0165(11) 0.0257(11) -0.0012(9) 0.0003(9) 0.0024(9) C(1) 0.0258(14) 0.0229(13) 0.0233(13) 0.0022(11) -0.0017(11) -0.0013(11) C(2) 0.0252(14) 0.0299(15) 0.0260(14) -0.0021(12) 0.0011(11) 0.0029(12) C(3) 0.0365(16) 0.0297(16) 0.0273(15) -0.0003(13) 0.0015(12) 0.0081(12) C(4) 0.0312(16) 0.0306(16) 0.0343(16) 0.0083(13) -0.0024(13) 0.0057(13) C(5) 0.0253(14) 0.0313(15) 0.0280(14) 0.0031(12) 0.0026(11) 0.0026(12) C(6) 0.0258(14) 0.0245(14) 0.0217(13) -0.0013(11) -0.0013(11) 0.0018(11) C(7) 0.0260(14) 0.0285(15) 0.0274(14) -0.0012(12) 0.0025(11) 0.0030(12) C(8) 0.0318(14) 0.0193(13) 0.0228(13) 0.0011(11) 0.0044(11) -0.0003(11) C(9) 0.0328(15) 0.0171(12) 0.0242(13) -0.0027(11) 0.0029(11) 0.0022(11) C(10) 0.0451(18) 0.0251(15) 0.0246(14) -0.0046(13) 0.0043(13) -0.0018(12) C(11) 0.052(2) 0.0323(17) 0.0252(15) -0.0101(15) -0.0081(14) 0.0008(13) C(12) 0.0362(17) 0.0349(18) 0.0365(17) -0.0096(14) -0.0084(14) 0.0007(14) C(13) 0.0300(15) 0.0282(15) 0.0318(15) -0.0028(12) -0.0018(12) 0.0010(12) C(14) 0.0325(15) 0.0177(13) 0.0249(14) -0.0021(11) -0.0013(11) 0.0014(10) C(15) 0.0319(15) 0.0205(14) 0.0301(15) -0.0004(12) 0.0053(12) 0.0016(11) C(16) 0.0408(18) 0.0204(14) 0.0374(17) -0.0015(13) 0.0085(14) -0.0001(12) C(17) 0.0405(18) 0.0260(15) 0.0388(17) -0.0013(13) -0.0021(14) 0.0095(13) C(18) 0.0337(16) 0.0206(14) 0.0299(15) -0.0018(11) 0.0066(12) 0.0007(11) C(19) 0.050(2) 0.0277(16) 0.0308(16) -0.0083(14) 0.0137(14) 0.0006(13) C(20) 0.055(2) 0.046(2) 0.048(2) -0.0130(18) 0.0261(18) -0.0006(18) C(21) 0.068(2) 0.0284(17) 0.0395(19) -0.0123(17) 0.0120(18) 0.0047(15) C(22) 0.077(2) 0.047(2) 0.0283(17) -0.005(2) 0.0106(18) 0.0018(16) C(23) 0.042(2) 0.042(2) 0.056(2) 0.0041(16) 0.0144(17) 0.0005(18) C(24) 0.0374(19) 0.060(2) 0.044(2) 0.0001(18) -0.0004(16) 0.0032(18) C(25) 0.070(2) 0.044(2) 0.048(2) -0.016(2) 0.024(2) -0.0055(18) C(26) 0.086(3) 0.053(2) 0.057(2) 0.030(2) 0.035(2) 0.026(2) C(27) 0.052(2) 0.123(4) 0.041(2) 0.037(3) 0.000(2) 0.016(2) C(28) 0.046(2) 0.083(3) 0.047(2) -0.011(2) 0.0057(18) -0.019(2) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 Bi(1) Bi(1) 3.05474(18) yes . 3_556 Bi(1) N(1) 2.934(2) yes . . Bi(1) C(1) 2.278(2) yes . . Bi(1) C(14) 2.276(2) yes . . N(1) C(7) 1.479(3) yes . . N(1) C(8) 1.475(3) yes . . N(1) C(15) 1.518(3) yes . . C(1) C(2) 1.396(4) yes . . C(1) C(6) 1.402(4) yes . . C(2) C(3) 1.388(4) yes . . C(3) C(4) 1.379(4) yes . . C(4) C(5) 1.387(4) yes . . C(5) C(6) 1.394(4) yes . . C(6) C(7) 1.514(4) yes . . C(8) C(9) 1.515(4) yes . . C(9) C(10) 1.394(4) yes . . C(9) C(14) 1.399(4) yes . . C(10) C(11) 1.388(5) yes . . C(11) C(12) 1.385(5) yes . . C(12) C(13) 1.392(4) yes . . C(13) C(14) 1.393(4) yes . . C(15) C(16) 1.536(4) yes . . C(15) C(17) 1.531(4) yes . . C(15) C(18) 1.547(4) yes . . C(18) C(19) 1.552(4) yes . . C(19) C(20) 1.544(5) yes . . C(19) C(21) 1.529(4) yes . . C(19) C(22) 1.524(4) yes . . C(23) C(24) 1.366(5) yes . . C(23) C(28) 1.360(5) yes . . C(24) C(25) 1.376(6) yes . . C(25) C(26) 1.365(6) yes . . C(26) C(27) 1.357(7) yes . . C(27) C(28) 1.360(8) yes . . C(2) H(1) 0.960 no . . C(3) H(2) 0.960 no . . C(4) H(3) 0.960 no . . C(5) H(4) 0.960 no . . C(7) H(5) 0.990 no . . C(7) H(6) 0.990 no . . C(8) H(7) 0.990 no . . C(8) H(8) 0.990 no . . C(10) H(9) 0.960 no . . C(11) H(10) 0.960 no . . C(12) H(11) 0.960 no . . C(13) H(12) 0.960 no . . C(16) H(13) 0.980 no . . C(16) H(14) 0.980 no . . C(16) H(15) 0.980 no . . C(17) H(16) 0.980 no . . C(17) H(17) 0.980 no . . C(17) H(18) 0.980 no . . C(18) H(19) 0.990 no . . C(18) H(20) 0.990 no . . C(20) H(21) 0.980 no . . C(20) H(22) 0.980 no . . C(20) H(23) 0.980 no . . C(21) H(24) 0.980 no . . C(21) H(25) 0.980 no . . C(21) H(26) 0.980 no . . C(22) H(27) 0.980 no . . C(22) H(28) 0.980 no . . C(22) H(29) 0.980 no . . C(23) H(30) 0.960 no . . C(24) H(31) 0.960 no . . C(25) H(32) 0.960 no . . C(26) H(33) 0.960 no . . C(27) H(34) 0.960 no . . C(28) H(35) 0.960 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 Bi(1) Bi(1) N(1) 153.39(4) yes 3_556 . . Bi(1) Bi(1) C(1) 94.13(7) yes 3_556 . . Bi(1) Bi(1) C(14) 93.76(7) yes 3_556 . . N(1) Bi(1) C(1) 69.08(8) yes . . . N(1) Bi(1) C(14) 69.09(9) yes . . . C(1) Bi(1) C(14) 96.90(10) yes . . . Bi(1) N(1) C(7) 96.11(16) yes . . . Bi(1) N(1) C(8) 98.57(16) yes . . . Bi(1) N(1) C(15) 121.05(16) yes . . . C(7) N(1) C(8) 111.6(2) yes . . . C(7) N(1) C(15) 112.8(2) yes . . . C(8) N(1) C(15) 114.7(2) yes . . . Bi(1) C(1) C(2) 122.0(2) yes . . . Bi(1) C(1) C(6) 119.4(2) yes . . . C(2) C(1) C(6) 118.6(2) yes . . . C(1) C(2) C(3) 121.7(2) yes . . . C(2) C(3) C(4) 119.5(2) yes . . . C(3) C(4) C(5) 119.6(2) yes . . . C(4) C(5) C(6) 121.5(2) yes . . . C(1) C(6) C(5) 119.1(2) yes . . . C(1) C(6) C(7) 123.1(2) yes . . . C(5) C(6) C(7) 117.8(2) yes . . . N(1) C(7) C(6) 113.6(2) yes . . . N(1) C(8) C(9) 114.5(2) yes . . . C(8) C(9) C(10) 118.3(2) yes . . . C(8) C(9) C(14) 122.6(2) yes . . . C(10) C(9) C(14) 119.0(2) yes . . . C(9) C(10) C(11) 121.8(3) yes . . . C(10) C(11) C(12) 119.3(3) yes . . . C(11) C(12) C(13) 119.5(3) yes . . . C(12) C(13) C(14) 121.6(3) yes . . . Bi(1) C(14) C(9) 121.4(2) yes . . . Bi(1) C(14) C(13) 119.4(2) yes . . . C(9) C(14) C(13) 119.0(2) yes . . . N(1) C(15) C(16) 107.7(2) yes . . . N(1) C(15) C(17) 107.3(2) yes . . . N(1) C(15) C(18) 109.2(2) yes . . . C(16) C(15) C(17) 107.4(2) yes . . . C(16) C(15) C(18) 111.1(2) yes . . . C(17) C(15) C(18) 114.0(2) yes . . . C(15) C(18) C(19) 124.1(2) yes . . . C(18) C(19) C(20) 105.3(2) yes . . . C(18) C(19) C(21) 113.6(2) yes . . . C(18) C(19) C(22) 112.7(2) yes . . . C(20) C(19) C(21) 108.3(3) yes . . . C(20) C(19) C(22) 107.4(3) yes . . . C(21) C(19) C(22) 109.2(2) yes . . . C(24) C(23) C(28) 119.4(4) yes . . . C(23) C(24) C(25) 119.7(3) yes . . . C(24) C(25) C(26) 120.3(4) yes . . . C(25) C(26) C(27) 119.4(4) yes . . . C(26) C(27) C(28) 120.4(4) yes . . . C(23) C(28) C(27) 120.8(4) yes . . . C(1) C(2) H(1) 119.2 no . . . C(3) C(2) H(1) 119.2 no . . . C(2) C(3) H(2) 120.1 no . . . C(4) C(3) H(2) 120.3 no . . . C(3) C(4) H(3) 120.2 no . . . C(5) C(4) H(3) 120.2 no . . . C(4) C(5) H(4) 119.4 no . . . C(6) C(5) H(4) 119.1 no . . . N(1) C(7) H(5) 108.3 no . . . N(1) C(7) H(6) 108.6 no . . . C(6) C(7) H(5) 108.3 no . . . C(6) C(7) H(6) 108.6 no . . . H(5) C(7) H(6) 109.5 no . . . N(1) C(8) H(7) 107.9 no . . . N(1) C(8) H(8) 108.4 no . . . C(9) C(8) H(7) 108.1 no . . . C(9) C(8) H(8) 108.4 no . . . H(7) C(8) H(8) 109.5 no . . . C(9) C(10) H(9) 119.1 no . . . C(11) C(10) H(9) 119.2 no . . . C(10) C(11) H(10) 120.4 no . . . C(12) C(11) H(10) 120.4 no . . . C(11) C(12) H(11) 120.1 no . . . C(13) C(12) H(11) 120.4 no . . . C(12) C(13) H(12) 119.3 no . . . C(14) C(13) H(12) 119.1 no . . . C(15) C(16) H(13) 109.4 no . . . C(15) C(16) H(14) 109.6 no . . . C(15) C(16) H(15) 109.5 no . . . H(13) C(16) H(14) 109.5 no . . . H(13) C(16) H(15) 109.5 no . . . H(14) C(16) H(15) 109.5 no . . . C(15) C(17) H(16) 109.3 no . . . C(15) C(17) H(17) 109.4 no . . . C(15) C(17) H(18) 109.7 no . . . H(16) C(17) H(17) 109.5 no . . . H(16) C(17) H(18) 109.5 no . . . H(17) C(17) H(18) 109.5 no . . . C(15) C(18) H(19) 105.8 no . . . C(15) C(18) H(20) 105.6 no . . . C(19) C(18) H(19) 105.9 no . . . C(19) C(18) H(20) 105.5 no . . . H(19) C(18) H(20) 109.5 no . . . C(19) C(20) H(21) 109.5 no . . . C(19) C(20) H(22) 109.5 no . . . C(19) C(20) H(23) 109.4 no . . . H(21) C(20) H(22) 109.5 no . . . H(21) C(20) H(23) 109.5 no . . . H(22) C(20) H(23) 109.5 no . . . C(19) C(21) H(24) 109.1 no . . . C(19) C(21) H(25) 109.6 no . . . C(19) C(21) H(26) 109.7 no . . . H(24) C(21) H(25) 109.5 no . . . H(24) C(21) H(26) 109.5 no . . . H(25) C(21) H(26) 109.5 no . . . C(19) C(22) H(27) 109.5 no . . . C(19) C(22) H(28) 109.2 no . . . C(19) C(22) H(29) 109.7 no . . . H(27) C(22) H(28) 109.5 no . . . H(27) C(22) H(29) 109.5 no . . . H(28) C(22) H(29) 109.5 no . . . C(24) C(23) H(30) 120.2 no . . . C(28) C(23) H(30) 120.4 no . . . C(23) C(24) H(31) 120.0 no . . . C(25) C(24) H(31) 120.3 no . . . C(24) C(25) H(32) 119.8 no . . . C(26) C(25) H(32) 119.9 no . . . C(25) C(26) H(33) 120.5 no . . . C(27) C(26) H(33) 120.1 no . . . C(26) C(27) H(34) 119.9 no . . . C(28) C(27) H(34) 119.8 no . . . C(23) C(28) H(35) 119.7 no . . . C(27) C(28) H(35) 119.6 no . . . loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 Bi(1) Bi(1) C(1) C(2) -6.3(2) ? 3_556 . . . Bi(1) Bi(1) C(1) C(6) 175.5(2) ? 3_556 . . . C(1) Bi(1) Bi(1) C(14) 82.79(10) ? . . 3_556 3_556 Bi(1) Bi(1) C(14) C(9) -149.0(2) ? 3_556 . . . Bi(1) Bi(1) C(14) C(13) 36.5(2) ? 3_556 . . . C(14) Bi(1) Bi(1) C(1) -82.79(10) ? . . 3_556 3_556 C(1) Bi(1) C(14) C(9) -54.4(2) ? . . . . C(1) Bi(1) C(14) C(13) 131.1(2) ? . . . . C(14) Bi(1) C(1) C(2) -100.6(2) ? . . . . C(14) Bi(1) C(1) C(6) 81.2(2) ? . . . . C(7) N(1) C(8) C(9) 137.9(2) ? . . . . C(8) N(1) C(7) C(6) -58.5(3) ? . . . . C(7) N(1) C(15) C(16) -65.8(3) ? . . . . C(7) N(1) C(15) C(17) 178.9(2) ? . . . . C(7) N(1) C(15) C(18) 54.9(3) ? . . . . C(15) N(1) C(7) C(6) 170.7(2) ? . . . . C(8) N(1) C(15) C(16) 164.9(2) ? . . . . C(8) N(1) C(15) C(17) 49.6(3) ? . . . . C(8) N(1) C(15) C(18) -74.4(2) ? . . . . C(15) N(1) C(8) C(9) -92.3(2) ? . . . . Bi(1) C(1) C(2) C(3) -178.1(2) ? . . . . Bi(1) C(1) C(6) C(5) -179.8(2) ? . . . . Bi(1) C(1) C(6) C(7) 2.0(3) ? . . . . C(2) C(1) C(6) C(5) 2.0(4) ? . . . . C(2) C(1) C(6) C(7) -176.3(2) ? . . . . C(6) C(1) C(2) C(3) 0.1(3) ? . . . . C(1) C(2) C(3) C(4) -1.4(4) ? . . . . C(2) C(3) C(4) C(5) 0.7(4) ? . . . . C(3) C(4) C(5) C(6) 1.4(4) ? . . . . C(4) C(5) C(6) C(1) -2.8(4) ? . . . . C(4) C(5) C(6) C(7) 175.6(2) ? . . . . C(1) C(6) C(7) N(1) -40.0(3) ? . . . . C(5) C(6) C(7) N(1) 141.7(2) ? . . . . N(1) C(8) C(9) C(10) 144.2(2) ? . . . . N(1) C(8) C(9) C(14) -38.6(3) ? . . . . C(8) C(9) C(10) C(11) 177.3(2) ? . . . . C(8) C(9) C(14) Bi(1) 8.5(3) ? . . . . C(8) C(9) C(14) C(13) -177.0(2) ? . . . . C(10) C(9) C(14) Bi(1) -174.2(2) ? . . . . C(10) C(9) C(14) C(13) 0.3(4) ? . . . . C(14) C(9) C(10) C(11) -0.0(4) ? . . . . C(9) C(10) C(11) C(12) -0.2(4) ? . . . . C(10) C(11) C(12) C(13) 0.2(4) ? . . . . C(11) C(12) C(13) C(14) 0.0(4) ? . . . . C(12) C(13) C(14) Bi(1) 174.3(2) ? . . . . C(12) C(13) C(14) C(9) -0.3(4) ? . . . . N(1) C(15) C(18) C(19) 163.0(2) ? . . . . C(16) C(15) C(18) C(19) -78.4(3) ? . . . . C(17) C(15) C(18) C(19) 43.0(3) ? . . . . C(15) C(18) C(19) C(20) 170.1(2) ? . . . . C(15) C(18) C(19) C(21) 51.8(4) ? . . . . C(15) C(18) C(19) C(22) -73.1(3) ? . . . . C(24) C(23) C(28) C(27) -0.2(5) ? . . . . C(28) C(23) C(24) C(25) -0.1(4) ? . . . . C(23) C(24) C(25) C(26) -0.2(5) ? . . . . C(24) C(25) C(26) C(27) 0.7(7) ? . . . . C(25) C(26) C(27) C(28) -0.9(7) ? . . . . C(26) C(27) C(28) C(23) 0.7(7) ? . . . . #============================================================================== # End of CIF #============================================================================== data_compound-1c _database_code_depnum_ccdc_archive 'CCDC 740997' _audit_creation_date 2007-12-12 _audit_creation_method 'by CrystalStructure 3.8' _audit_update_record ? #============================================================================== _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction CrystalStructure _computing_structure_solution 'DIRDIF99 (PATTY)' _computing_structure_refinement CRYSTALS _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C37 H38 Bi2 N2 ' _chemical_formula_moiety 'C30 H30 Bi2 N2, C7 H8 ' _chemical_formula_weight 928.68 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,-Y,-Z #------------------------------------------------------------------------------ _cell_length_a 8.8609(6) _cell_length_b 9.3401(6) _cell_length_c 11.5513(8) _cell_angle_alpha 69.858(1) _cell_angle_beta 70.943(1) _cell_angle_gamma 65.058(1) _cell_volume 795.16(9) _cell_formula_units_Z 1 _cell_measurement_reflns_used 3394 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 28.2 _cell_measurement_temperature 153(2) #------------------------------------------------------------------------------ _exptl_crystal_description prismatic _exptl_crystal_colour orange-red _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.939 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440.00 _exptl_absorpt_coefficient_mu 11.058 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.269 _exptl_absorpt_correction_T_max 0.414 _exptl_absorpt_process_details ; SADABS; Sheldrick 1996 ; #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean '8.366 [pixels/mm]' _diffrn_ambient_temperature 153(2) _diffrn_reflns_number 4831 _diffrn_reflns_av_R_equivalents 0.014 _diffrn_reflns_theta_max 28.24 _diffrn_measured_fraction_theta_max 0.878 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.963 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 10 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 3355 _reflns_number_gt 3177 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0229 _refine_ls_wR_factor_ref 0.0582 _atom_sites_solution_primary heavy _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 3355 _refine_ls_number_parameters 214 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[1.0000\s(Fo^2^) + 0.0800]/(4Fo^2^)' _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 0.92 _refine_diff_density_min -1.30 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Bi Bi -4.108 10.257 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Bi(1) Bi 0.11741(2) 0.06421(2) 0.02449(2) 0.01781(4) Uani 1.00 1 d . . . N(1) N 0.2161(5) 0.1649(5) 0.1777(4) 0.0234(10) Uani 1.00 1 d . . . C(1) C -0.0988(6) 0.2745(5) 0.1006(4) 0.0216(11) Uani 1.00 1 d . . . C(2) C -0.2689(6) 0.3149(5) 0.0982(4) 0.0247(12) Uani 1.00 1 d . . . C(3) C -0.3977(6) 0.4454(6) 0.1429(5) 0.0330(13) Uani 1.00 1 d . . . C(4) C -0.3600(7) 0.5383(6) 0.1912(5) 0.0344(14) Uani 1.00 1 d . . . C(5) C -0.1911(7) 0.5015(6) 0.1947(5) 0.0304(13) Uani 1.00 1 d . . . C(6) C -0.0606(6) 0.3715(5) 0.1490(4) 0.0249(12) Uani 1.00 1 d . . . C(7) C 0.1215(6) 0.3387(6) 0.1502(5) 0.0288(13) Uani 1.00 1 d . . . C(8) C 0.1572(7) 0.0808(6) 0.3059(4) 0.0281(13) Uani 1.00 1 d . . . C(9) C 0.1666(6) -0.0872(6) 0.3123(4) 0.0226(11) Uani 1.00 1 d . . . C(10) C 0.1925(7) -0.2070(6) 0.4239(5) 0.0321(14) Uani 1.00 1 d . . . C(11) C 0.1911(8) -0.3603(7) 0.4392(5) 0.0376(15) Uani 1.00 1 d . . . C(12) C 0.1688(7) -0.3967(6) 0.3412(5) 0.0339(14) Uani 1.00 1 d . . . C(13) C 0.1457(6) -0.2792(6) 0.2290(4) 0.0271(12) Uani 1.00 1 d . . . C(14) C 0.1457(5) -0.1237(5) 0.2128(4) 0.0202(11) Uani 1.00 1 d . . . C(15) C 0.4010(7) 0.1247(7) 0.1459(6) 0.0382(16) Uani 1.00 1 d . . . C(16) C 0.3165(15) 0.0132(18) 0.6249(11) 0.045(3) Uani 0.50 1 d P . . C(17) C 0.3083(12) 0.1780(11) 0.5964(8) 0.072(2) Uani 1.00 1 d . . . C(18) C 0.4491(18) 0.2078(16) 0.4865(15) 0.051(4) Uani 0.50 1 d P . . C(19) C 0.5627(8) 0.0988(7) 0.4307(6) 0.0419(17) Uani 1.00 1 d . . . C(20) C 0.5745(14) -0.0642(14) 0.4607(10) 0.035(2) Uani 0.50 1 d P . . H(1) H -0.2971 0.2503 0.0651 0.030 Uiso 1.00 1 c R . . H(2) H -0.5131 0.4711 0.1391 0.037 Uiso 1.00 1 c R . . H(3) H -0.4490 0.6277 0.2230 0.037 Uiso 1.00 1 c R . . H(4) H -0.1644 0.5664 0.2286 0.037 Uiso 1.00 1 c R . . H(5) H 0.1221 0.3849 0.2154 0.038 Uiso 1.00 1 c R . . H(6) H 0.1764 0.3910 0.0663 0.038 Uiso 1.00 1 c R . . H(7) H 0.2289 0.0708 0.3605 0.036 Uiso 1.00 1 c R . . H(8) H 0.0374 0.1457 0.3368 0.036 Uiso 1.00 1 c R . . H(9) H 0.2114 -0.1827 0.4911 0.040 Uiso 1.00 1 c R . . H(10) H 0.2058 -0.4406 0.5173 0.045 Uiso 1.00 1 c R . . H(11) H 0.1689 -0.5029 0.3505 0.040 Uiso 1.00 1 c R . . H(12) H 0.1298 -0.3051 0.1612 0.033 Uiso 1.00 1 c R . . H(13) H 0.4358 0.1422 0.2107 0.049 Uiso 1.00 1 c R . . H(14) H 0.4575 0.0104 0.1418 0.049 Uiso 1.00 1 c R . . H(15) H 0.4334 0.1945 0.0639 0.049 Uiso 1.00 1 c 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Bi(1) 0.01675(9) 0.01980(9) 0.01875(9) -0.00501(6) -0.00576(6) -0.00671(6) N(1) 0.021(2) 0.030(2) 0.030(2) -0.0133(17) -0.0097(16) -0.0105(17) C(1) 0.025(2) 0.022(2) 0.020(2) -0.0099(19) -0.0033(18) -0.0065(18) C(2) 0.020(2) 0.022(2) 0.032(2) -0.0064(19) -0.0056(19) -0.009(2) C(3) 0.022(2) 0.030(2) 0.040(3) -0.004(2) -0.007(2) -0.007(2) C(4) 0.035(3) 0.024(2) 0.032(2) -0.000(2) -0.002(2) -0.011(2) C(5) 0.039(3) 0.023(2) 0.030(2) -0.008(2) -0.008(2) -0.012(2) C(6) 0.030(2) 0.021(2) 0.024(2) -0.009(2) -0.008(2) -0.0043(19) C(7) 0.036(2) 0.026(2) 0.033(2) -0.014(2) -0.013(2) -0.008(2) C(8) 0.035(2) 0.032(2) 0.024(2) -0.011(2) -0.012(2) -0.010(2) C(9) 0.020(2) 0.027(2) 0.023(2) -0.0068(19) -0.0082(18) -0.0081(19) C(10) 0.037(3) 0.037(2) 0.025(2) -0.013(2) -0.012(2) -0.006(2) C(11) 0.051(3) 0.035(2) 0.025(2) -0.017(2) -0.014(2) 0.002(2) C(12) 0.045(3) 0.024(2) 0.032(2) -0.011(2) -0.012(2) -0.003(2) C(13) 0.031(2) 0.025(2) 0.028(2) -0.008(2) -0.010(2) -0.008(2) C(14) 0.018(2) 0.023(2) 0.020(2) -0.0047(17) -0.0057(17) -0.0059(18) C(15) 0.027(2) 0.045(3) 0.049(3) -0.018(2) -0.013(2) -0.008(2) C(16) 0.029(6) 0.073(9) 0.031(6) -0.023(6) -0.002(4) -0.009(6) C(17) 0.074(5) 0.067(5) 0.067(5) -0.010(4) -0.028(4) -0.015(4) C(18) 0.048(7) 0.037(6) 0.069(9) -0.005(6) -0.036(7) -0.002(6) C(19) 0.046(3) 0.038(3) 0.043(3) -0.015(2) -0.029(2) 0.007(2) C(20) 0.028(5) 0.039(6) 0.030(5) 0.004(4) -0.019(4) -0.007(4) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 Bi(1) Bi(1) 3.0707(3) yes . 2_555 Bi(1) N(1) 2.763(6) yes . . Bi(1) C(1) 2.284(4) yes . . Bi(1) C(14) 2.287(4) yes . . N(1) C(7) 1.453(6) yes . . N(1) C(8) 1.457(6) yes . . N(1) C(15) 1.464(7) yes . . C(1) C(2) 1.398(7) yes . . C(1) C(6) 1.407(9) yes . . C(2) C(3) 1.389(6) yes . . C(3) C(4) 1.369(11) yes . . C(4) C(5) 1.398(9) yes . . C(5) C(6) 1.396(6) yes . . C(6) C(7) 1.514(8) yes . . C(8) C(9) 1.513(8) yes . . C(9) C(10) 1.396(6) yes . . C(9) C(14) 1.391(9) yes . . C(10) C(11) 1.386(10) yes . . C(11) C(12) 1.380(11) yes . . C(12) C(13) 1.389(6) yes . . C(13) C(14) 1.399(8) yes . . C(16) C(17) 1.43(2) yes . . C(16) C(19) 1.313(14) yes . 2_656 C(17) C(18) 1.504(16) yes . . C(18) C(19) 1.276(15) yes . . C(19) C(20) 1.406(15) yes . . C(19) C(20) 1.487(12) yes . 2_656 C(2) H(1) 0.960 no . . C(3) H(2) 0.960 no . . C(4) H(3) 0.960 no . . C(5) H(4) 0.960 no . . C(7) H(5) 0.990 no . . C(7) H(6) 0.990 no . . C(8) H(7) 0.990 no . . C(8) H(8) 0.990 no . . C(10) H(9) 0.960 no . . C(11) H(10) 0.960 no . . C(12) H(11) 0.960 no . . C(13) H(12) 0.960 no . . C(15) H(13) 0.980 no . . C(15) H(14) 0.980 no . . C(15) H(15) 0.980 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 Bi(1) Bi(1) N(1) 152.06(8) yes 2_555 . . Bi(1) Bi(1) C(1) 95.00(17) yes 2_555 . . Bi(1) Bi(1) C(14) 92.55(16) yes 2_555 . . N(1) Bi(1) C(1) 68.44(18) yes . . . N(1) Bi(1) C(14) 68.94(18) yes . . . C(1) Bi(1) C(14) 98.12(15) yes . . . Bi(1) N(1) C(7) 101.6(3) yes . . . Bi(1) N(1) C(8) 105.1(4) yes . . . Bi(1) N(1) C(15) 110.8(4) yes . . . C(7) N(1) C(8) 113.0(3) yes . . . C(7) N(1) C(15) 113.4(4) yes . . . C(8) N(1) C(15) 112.1(4) yes . . . Bi(1) C(1) C(2) 122.8(4) yes . . . Bi(1) C(1) C(6) 119.3(3) yes . . . C(2) C(1) C(6) 117.9(4) yes . . . C(1) C(2) C(3) 121.7(6) yes . . . C(2) C(3) C(4) 120.1(5) yes . . . C(3) C(4) C(5) 119.6(5) yes . . . C(4) C(5) C(6) 120.7(6) yes . . . C(1) C(6) C(5) 120.0(5) yes . . . C(1) C(6) C(7) 120.8(4) yes . . . C(5) C(6) C(7) 119.2(6) yes . . . N(1) C(7) C(6) 110.5(5) yes . . . N(1) C(8) C(9) 112.0(4) yes . . . C(8) C(9) C(10) 118.1(5) yes . . . C(8) C(9) C(14) 122.2(4) yes . . . C(10) C(9) C(14) 119.7(5) yes . . . C(9) C(10) C(11) 121.1(6) yes . . . C(10) C(11) C(12) 119.4(5) yes . . . C(11) C(12) C(13) 119.9(6) yes . . . C(12) C(13) C(14) 121.1(6) yes . . . Bi(1) C(14) C(9) 120.9(3) yes . . . Bi(1) C(14) C(13) 120.4(4) yes . . . C(9) C(14) C(13) 118.7(4) yes . . . C(17) C(16) C(19) 124.7(10) yes . . 2_656 C(17) C(16) C(20) 58.4(9) yes . . 2_656 C(19) C(16) C(20) 66.3(8) yes 2_656 . 2_656 C(16) C(17) C(18) 110.4(9) yes . . . C(16) C(17) C(20) 54.1(8) yes . . 2_656 C(18) C(17) C(20) 56.3(8) yes . . 2_656 C(17) C(18) C(19) 124.1(12) yes . . . C(17) C(18) C(20) 55.0(8) yes . . 2_656 C(19) C(18) C(20) 69.1(9) yes . . 2_656 C(16) C(19) C(18) 178.0(14) yes 2_656 . . C(16) C(19) C(20) 54.9(8) yes 2_656 . . C(16) C(19) C(20) 123.1(9) yes 2_656 . 2_656 C(18) C(19) C(20) 125.8(9) yes . . . C(18) C(19) C(20) 57.6(8) yes . . 2_656 C(20) C(19) C(20) 68.2(7) yes . . 2_656 C(16) C(20) C(17) 67.5(9) yes 2_656 . 2_656 C(16) C(20) C(18) 136.1(12) yes 2_656 . 2_656 C(16) C(20) C(19) 58.7(9) yes 2_656 . . C(16) C(20) C(19) 170.1(14) yes 2_656 . 2_656 C(16) C(20) C(20) 116.9(12) yes 2_656 . 2_656 C(17) C(20) C(18) 68.7(9) yes 2_656 . 2_656 C(17) C(20) C(19) 126.2(9) yes 2_656 . . C(17) C(20) C(19) 122.0(10) yes 2_656 . 2_656 C(17) C(20) C(20) 175.5(11) yes 2_656 . 2_656 C(18) C(20) C(19) 165.0(10) yes 2_656 . . C(18) C(20) C(19) 53.3(7) yes 2_656 . 2_656 C(18) C(20) C(20) 106.8(9) yes 2_656 . 2_656 C(19) C(20) C(19) 111.8(8) yes . . 2_656 C(19) C(20) C(20) 58.2(6) yes . . 2_656 C(19) C(20) C(20) 53.5(6) yes 2_656 . 2_656 C(1) C(2) H(1) 118.9 no . . . C(3) C(2) H(1) 119.3 no . . . C(2) C(3) H(2) 119.9 no . . . C(4) C(3) H(2) 120.0 no . . . C(3) C(4) H(3) 120.2 no . . . C(5) C(4) H(3) 120.2 no . . . C(4) C(5) H(4) 119.8 no . . . C(6) C(5) H(4) 119.6 no . . . N(1) C(7) H(5) 109.3 no . . . N(1) C(7) H(6) 109.2 no . . . C(6) C(7) H(5) 109.4 no . . . C(6) C(7) H(6) 109.0 no . . . H(5) C(7) H(6) 109.5 no . . . N(1) C(8) H(7) 108.9 no . . . N(1) C(8) H(8) 108.7 no . . . C(9) C(8) H(7) 109.0 no . . . C(9) C(8) H(8) 108.8 no . . . H(7) C(8) H(8) 109.5 no . . . C(9) C(10) H(9) 119.5 no . . . C(11) C(10) H(9) 119.4 no . . . C(10) C(11) H(10) 120.3 no . . . C(12) C(11) H(10) 120.3 no . . . C(11) C(12) H(11) 120.1 no . . . C(13) C(12) H(11) 120.0 no . . . C(12) C(13) H(12) 119.5 no . . . C(14) C(13) H(12) 119.3 no . . . N(1) C(15) H(13) 109.5 no . . . N(1) C(15) H(14) 109.5 no . . . N(1) C(15) H(15) 109.4 no . . . H(13) C(15) H(14) 109.5 no . . . H(13) C(15) H(15) 109.5 no . . . H(14) C(15) H(15) 109.5 no . . . #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== data_compound-4 _database_code_depnum_ccdc_archive 'CCDC 740998' _audit_creation_date 2008-01-13 _audit_creation_method 'by CrystalStructure 3.8' _audit_update_record ? #============================================================================== _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction CrystalStructure _computing_structure_solution 'DIRDIF99 (PATTY)' _computing_structure_refinement CRYSTALS _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C30 H31 Bi N O2 P ' _chemical_formula_moiety 'C30 H31 Bi N O2 P ' _chemical_formula_weight 677.53 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2-X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 1/2+X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 12.6960(6) _cell_length_b 11.9372(5) _cell_length_c 18.0921(8) _cell_angle_alpha 90.0000 _cell_angle_beta 105.403(1) _cell_angle_gamma 90.0000 _cell_volume 2643.5(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 8702 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 28.1 _cell_measurement_temperature 153(2) #------------------------------------------------------------------------------ _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.702 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328.00 _exptl_absorpt_coefficient_mu 6.746 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.335 _exptl_absorpt_correction_T_max 0.443 _exptl_absorpt_process_details ; SADABS; Sheldrick 1996 ; #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean '8.366 [pixels/mm]' _diffrn_ambient_temperature 153(2) _diffrn_reflns_number 15606 _diffrn_reflns_av_R_equivalents 0.019 _diffrn_reflns_theta_max 28.28 _diffrn_measured_fraction_theta_max 0.915 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.967 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 23 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 5874 _reflns_number_gt 5205 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0180 _refine_ls_wR_factor_ref 0.0406 _atom_sites_solution_primary heavy _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 5873 _refine_ls_number_parameters 347 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[0.3000\s(Fo^2^) + 0.0500]/(4Fo^2^)' _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 0.56 _refine_diff_density_min -0.50 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; P P 0.102 0.094 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Bi Bi -4.108 10.257 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Bi(1) Bi 0.239610(10) 0.162030(10) 0.162200(10) 0.01890(2) Uani 1.00 1 d . . . P(1) P 0.39505(6) 0.25672(6) 0.05144(4) 0.02325(16) Uani 1.00 1 d . . . O(1) O 0.38400(15) 0.16672(16) 0.10996(11) 0.0251(4) Uani 1.00 1 d . . . O(2) O 0.32209(18) 0.35482(18) 0.04458(13) 0.0371(6) Uani 1.00 1 d . . . N(1) N 0.12003(17) 0.06140(19) 0.23407(12) 0.0212(5) Uani 1.00 1 d . . . C(1) C 0.1836(2) 0.0037(2) 0.09841(15) 0.0233(6) Uani 1.00 1 d . . . C(2) C 0.2292(2) -0.0389(2) 0.04230(16) 0.0293(7) Uani 1.00 1 d . . . C(3) C 0.1862(2) -0.1349(2) 0.00267(18) 0.0384(8) Uani 1.00 1 d . . . C(4) C 0.0983(3) -0.1883(2) 0.01822(19) 0.0417(9) Uani 1.00 1 d . . . C(5) C 0.0525(2) -0.1459(2) 0.07403(17) 0.0345(8) Uani 1.00 1 d . . . C(6) C 0.0942(2) -0.0490(2) 0.11415(15) 0.0258(6) Uani 1.00 1 d . . . C(7) C 0.0404(2) -0.0009(2) 0.17245(15) 0.0269(6) Uani 1.00 1 d . . . C(8) C 0.1941(2) -0.0216(2) 0.28393(15) 0.0244(6) Uani 1.00 1 d . . . C(9) C 0.3119(2) 0.0162(2) 0.31046(15) 0.0228(6) Uani 1.00 1 d . . . C(10) C 0.3795(2) -0.0244(2) 0.37910(15) 0.0270(7) Uani 1.00 1 d . . . C(11) C 0.4896(2) 0.0035(2) 0.40039(16) 0.0298(7) Uani 1.00 1 d . . . C(12) C 0.5324(2) 0.0732(2) 0.35488(16) 0.0300(7) Uani 1.00 1 d . . . C(13) C 0.4657(2) 0.1159(2) 0.28736(16) 0.0266(7) Uani 1.00 1 d . . . C(14) C 0.3559(2) 0.0865(2) 0.26458(14) 0.0216(6) Uani 1.00 1 d . . . C(15) C 0.0645(2) 0.1406(2) 0.27839(16) 0.0270(7) Uani 1.00 1 d . . . C(16) C 0.0129(2) 0.2372(2) 0.22640(18) 0.0342(8) Uani 1.00 1 d . . . C(17) C -0.0237(2) 0.0798(2) 0.30737(19) 0.0373(8) Uani 1.00 1 d . . . C(18) C 0.1506(2) 0.1889(2) 0.34677(17) 0.0341(8) Uani 1.00 1 d . . . C(19) C 0.3738(2) 0.1851(2) -0.03966(15) 0.0228(6) Uani 1.00 1 d . . . C(20) C 0.4551(2) 0.1202(2) -0.05682(16) 0.0262(6) Uani 1.00 1 d . . . C(21) C 0.4343(2) 0.0600(2) -0.12463(17) 0.0324(7) Uani 1.00 1 d . . . C(22) C 0.3322(2) 0.0640(2) -0.17542(17) 0.0370(8) Uani 1.00 1 d . . . C(23) C 0.2514(2) 0.1285(3) -0.15937(18) 0.0406(8) Uani 1.00 1 d . . . C(24) C 0.2712(2) 0.1898(2) -0.09214(17) 0.0338(8) Uani 1.00 1 d . . . C(25) C 0.5377(2) 0.2944(2) 0.07762(15) 0.0228(6) Uani 1.00 1 d . . . C(26) C 0.6122(2) 0.2429(2) 0.13824(15) 0.0246(6) Uani 1.00 1 d . . . C(27) C 0.7210(2) 0.2755(2) 0.15926(16) 0.0300(7) Uani 1.00 1 d . . . C(28) C 0.7562(2) 0.3598(2) 0.11949(18) 0.0320(7) Uani 1.00 1 d . . . C(29) C 0.6840(2) 0.4112(2) 0.05785(18) 0.0325(7) Uani 1.00 1 d . . . C(30) C 0.5754(2) 0.3771(2) 0.03661(16) 0.0289(7) Uani 1.00 1 d . . . H(1) H 0.2899 -0.0024 0.0313 0.035 Uiso 1.00 1 c R . . H(2) H 0.2174 -0.1641 -0.0356 0.046 Uiso 1.00 1 c R . . H(3) H 0.0690 -0.2540 -0.0092 0.048 Uiso 1.00 1 c R . . H(4) H -0.0078 -0.1831 0.0850 0.041 Uiso 1.00 1 c R . . H(5) H 0.0099 -0.0604 0.1949 0.033 Uiso 1.00 1 c R . . H(6) H -0.0160 0.0490 0.1472 0.033 Uiso 1.00 1 c R . . H(7) H 0.1683 -0.0348 0.3279 0.029 Uiso 1.00 1 c R . . H(8) H 0.1914 -0.0893 0.2560 0.029 Uiso 1.00 1 c R . . H(9) H 0.3502 -0.0710 0.4113 0.033 Uiso 1.00 1 c R . . H(10) H 0.5357 -0.0255 0.4466 0.035 Uiso 1.00 1 c R . . H(11) H 0.6079 0.0918 0.3698 0.036 Uiso 1.00 1 c R . . H(12) H 0.4950 0.1652 0.2566 0.033 Uiso 1.00 1 c R . . H(13) H -0.0197 0.2879 0.2543 0.043 Uiso 1.00 1 c R . . H(14) H 0.0676 0.2750 0.2090 0.043 Uiso 1.00 1 c R . . H(15) H -0.0413 0.2091 0.1836 0.043 Uiso 1.00 1 c R . . H(16) H -0.0783 0.0515 0.2648 0.047 Uiso 1.00 1 c R . . H(17) H 0.0085 0.0196 0.3398 0.047 Uiso 1.00 1 c R . . H(18) H -0.0560 0.1309 0.3352 0.047 Uiso 1.00 1 c R . . H(19) H 0.1819 0.1303 0.3811 0.041 Uiso 1.00 1 c R . . H(20) H 0.2061 0.2248 0.3291 0.042 Uiso 1.00 1 c R . . H(21) H 0.1172 0.2419 0.3725 0.041 Uiso 1.00 1 c R . . H(22) H 0.5254 0.1171 -0.0216 0.031 Uiso 1.00 1 c R . . H(23) H 0.4904 0.0161 -0.1360 0.040 Uiso 1.00 1 c R . . H(24) H 0.3176 0.0222 -0.2217 0.044 Uiso 1.00 1 c R . . H(25) H 0.1812 0.1308 -0.1947 0.047 Uiso 1.00 1 c R . . H(26) H 0.2155 0.2353 -0.0818 0.041 Uiso 1.00 1 c R . . H(27) H 0.5882 0.1847 0.1657 0.030 Uiso 1.00 1 c R . . H(28) H 0.7711 0.2398 0.2011 0.036 Uiso 1.00 1 c R . . H(29) H 0.8305 0.3828 0.1346 0.040 Uiso 1.00 1 c R . . H(30) H 0.7085 0.4689 0.0303 0.041 Uiso 1.00 1 c R . . H(31) H 0.5259 0.4107 -0.0065 0.036 Uiso 1.00 1 c 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Bi(1) 0.02091(5) 0.01789(5) 0.01961(5) 0.00104(4) 0.00836(3) 0.00128(4) P(1) 0.0243(3) 0.0252(3) 0.0234(3) 0.0036(2) 0.0117(2) 0.0037(2) O(1) 0.0262(9) 0.0275(10) 0.0250(9) 0.0020(8) 0.0126(7) 0.0055(8) O(2) 0.0399(12) 0.0355(12) 0.0419(12) 0.0121(9) 0.0212(10) 0.0068(9) N(1) 0.0199(10) 0.0240(11) 0.0207(10) -0.0007(8) 0.0072(8) 0.0004(8) C(1) 0.0267(13) 0.0205(12) 0.0216(12) 0.0032(10) 0.0043(10) 0.0006(10) C(2) 0.0357(15) 0.0301(15) 0.0225(13) 0.0035(12) 0.0083(11) 0.0010(11) C(3) 0.054(2) 0.0359(17) 0.0259(14) 0.0065(14) 0.0120(13) -0.0068(12) C(4) 0.056(2) 0.0314(16) 0.0334(16) -0.0078(15) 0.0052(15) -0.0111(13) C(5) 0.0373(16) 0.0321(16) 0.0325(15) -0.0081(13) 0.0064(12) -0.0039(12) C(6) 0.0273(13) 0.0268(14) 0.0222(12) -0.0013(11) 0.0045(10) 0.0006(10) C(7) 0.0243(12) 0.0312(15) 0.0268(13) -0.0041(11) 0.0093(10) -0.0009(11) C(8) 0.0303(13) 0.0197(12) 0.0236(13) 0.0004(10) 0.0078(10) 0.0050(10) C(9) 0.0274(13) 0.0205(12) 0.0215(12) 0.0017(10) 0.0083(10) -0.0022(10) C(10) 0.0343(15) 0.0249(13) 0.0232(13) 0.0032(11) 0.0102(11) 0.0010(11) C(11) 0.0332(15) 0.0332(15) 0.0207(12) 0.0106(12) 0.0031(11) -0.0011(11) C(12) 0.0248(13) 0.0359(16) 0.0290(14) 0.0031(12) 0.0068(11) -0.0046(12) C(13) 0.0276(14) 0.0288(14) 0.0257(13) -0.0003(11) 0.0112(11) -0.0017(11) C(14) 0.0256(13) 0.0209(12) 0.0196(12) 0.0032(10) 0.0079(10) -0.0018(10) C(15) 0.0261(13) 0.0307(15) 0.0280(13) 0.0005(11) 0.0141(11) -0.0017(11) C(16) 0.0332(16) 0.0362(16) 0.0383(16) 0.0105(13) 0.0183(13) 0.0023(13) C(17) 0.0338(16) 0.0451(18) 0.0392(17) -0.0052(14) 0.0206(13) -0.0027(14) C(18) 0.0325(15) 0.0407(17) 0.0306(15) 0.0012(13) 0.0111(12) -0.0105(13) C(19) 0.0241(12) 0.0252(13) 0.0205(12) -0.0006(10) 0.0083(10) 0.0067(10) C(20) 0.0266(13) 0.0270(13) 0.0247(13) 0.0014(11) 0.0064(11) 0.0024(11) C(21) 0.0400(16) 0.0298(15) 0.0295(15) 0.0025(13) 0.0128(12) -0.0003(12) C(22) 0.0497(19) 0.0339(16) 0.0254(14) -0.0114(14) 0.0066(13) -0.0012(12) C(23) 0.0323(16) 0.056(2) 0.0285(15) -0.0073(15) -0.0013(12) 0.0089(14) C(24) 0.0238(14) 0.0456(18) 0.0321(15) 0.0023(12) 0.0073(11) 0.0081(13) C(25) 0.0270(13) 0.0201(12) 0.0248(13) 0.0002(10) 0.0131(10) -0.0033(10) C(26) 0.0288(14) 0.0252(13) 0.0214(12) -0.0017(11) 0.0095(10) 0.0021(10) C(27) 0.0294(15) 0.0342(15) 0.0270(14) -0.0024(12) 0.0084(12) -0.0018(12) C(28) 0.0308(15) 0.0319(15) 0.0364(16) -0.0097(12) 0.0145(12) -0.0074(12) C(29) 0.0414(17) 0.0249(14) 0.0372(16) -0.0084(12) 0.0207(13) 0.0003(12) C(30) 0.0394(16) 0.0242(13) 0.0260(14) 0.0003(12) 0.0138(12) 0.0029(11) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 Bi(1) O(1) 2.275(2) yes . . Bi(1) N(1) 2.547(2) yes . . Bi(1) C(1) 2.230(2) yes . . Bi(1) C(14) 2.230(2) yes . . P(1) O(1) 1.541(2) yes . . P(1) O(2) 1.478(2) yes . . P(1) C(19) 1.812(2) yes . . P(1) C(25) 1.803(2) yes . . N(1) C(7) 1.489(3) yes . . N(1) C(8) 1.492(3) yes . . N(1) C(15) 1.528(3) yes . . C(1) C(2) 1.392(4) yes . . C(1) C(6) 1.392(4) yes . . C(2) C(3) 1.385(4) yes . . C(3) C(4) 1.378(5) yes . . C(4) C(5) 1.388(5) yes . . C(5) C(6) 1.393(4) yes . . C(6) C(7) 1.513(4) yes . . C(8) C(9) 1.514(3) yes . . C(9) C(10) 1.396(3) yes . . C(9) C(14) 1.397(4) yes . . C(10) C(11) 1.388(4) yes . . C(11) C(12) 1.380(4) yes . . C(12) C(13) 1.386(3) yes . . C(13) C(14) 1.390(3) yes . . C(15) C(16) 1.522(4) yes . . C(15) C(17) 1.539(4) yes . . C(15) C(18) 1.530(3) yes . . C(19) C(20) 1.390(4) yes . . C(19) C(24) 1.394(3) yes . . C(20) C(21) 1.385(4) yes . . C(21) C(22) 1.376(4) yes . . C(22) C(23) 1.374(5) yes . . C(23) C(24) 1.384(4) yes . . C(25) C(26) 1.387(3) yes . . C(25) C(30) 1.394(4) yes . . C(26) C(27) 1.387(3) yes . . C(27) C(28) 1.378(4) yes . . C(28) C(29) 1.385(3) yes . . C(29) C(30) 1.389(4) yes . . C(2) H(1) 0.950 no . . C(3) H(2) 0.950 no . . C(4) H(3) 0.950 no . . C(5) H(4) 0.950 no . . C(7) H(5) 0.950 no . . C(7) H(6) 0.950 no . . C(8) H(7) 0.950 no . . C(8) H(8) 0.950 no . . C(10) H(9) 0.950 no . . C(11) H(10) 0.950 no . . C(12) H(11) 0.950 no . . C(13) H(12) 0.950 no . . C(16) H(13) 0.950 no . . C(16) H(14) 0.950 no . . C(16) H(15) 0.950 no . . C(17) H(16) 0.950 no . . C(17) H(17) 0.950 no . . C(17) H(18) 0.950 no . . C(18) H(19) 0.950 no . . C(18) H(20) 0.950 no . . C(18) H(21) 0.950 no . . C(20) H(22) 0.950 no . . C(21) H(23) 0.950 no . . C(22) H(24) 0.950 no . . C(23) H(25) 0.950 no . . C(24) H(26) 0.950 no . . C(26) H(27) 0.950 no . . C(27) H(28) 0.950 no . . C(28) H(29) 0.950 no . . C(29) H(30) 0.950 no . . C(30) H(31) 0.950 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 O(1) Bi(1) N(1) 151.51(6) yes . . . O(1) Bi(1) C(1) 89.28(9) yes . . . O(1) Bi(1) C(14) 85.78(8) yes . . . N(1) Bi(1) C(1) 73.32(9) yes . . . N(1) Bi(1) C(14) 74.81(8) yes . . . C(1) Bi(1) C(14) 97.87(9) yes . . . O(1) P(1) O(2) 116.16(13) yes . . . O(1) P(1) C(19) 106.09(11) yes . . . O(1) P(1) C(25) 105.18(11) yes . . . O(2) P(1) C(19) 111.04(12) yes . . . O(2) P(1) C(25) 112.82(12) yes . . . C(19) P(1) C(25) 104.67(13) yes . . . Bi(1) O(1) P(1) 122.21(10) yes . . . Bi(1) N(1) C(7) 103.37(16) yes . . . Bi(1) N(1) C(8) 104.86(16) yes . . . Bi(1) N(1) C(15) 113.38(16) yes . . . C(7) N(1) C(8) 108.3(2) yes . . . C(7) N(1) C(15) 112.7(2) yes . . . C(8) N(1) C(15) 113.4(2) yes . . . Bi(1) C(1) C(2) 123.3(2) yes . . . Bi(1) C(1) C(6) 116.3(2) yes . . . C(2) C(1) C(6) 120.3(2) yes . . . C(1) C(2) C(3) 119.8(3) yes . . . C(2) C(3) C(4) 120.4(3) yes . . . C(3) C(4) C(5) 119.9(3) yes . . . C(4) C(5) C(6) 120.4(3) yes . . . C(1) C(6) C(5) 119.1(2) yes . . . C(1) C(6) C(7) 120.9(2) yes . . . C(5) C(6) C(7) 119.9(2) yes . . . N(1) C(7) C(6) 111.7(2) yes . . . N(1) C(8) C(9) 113.9(2) yes . . . C(8) C(9) C(10) 120.1(2) yes . . . C(8) C(9) C(14) 120.5(2) yes . . . C(10) C(9) C(14) 119.3(2) yes . . . C(9) C(10) C(11) 120.0(2) yes . . . C(10) C(11) C(12) 120.4(2) yes . . . C(11) C(12) C(13) 120.2(2) yes . . . C(12) C(13) C(14) 119.9(2) yes . . . Bi(1) C(14) C(9) 117.10(17) yes . . . Bi(1) C(14) C(13) 122.32(19) yes . . . C(9) C(14) C(13) 120.2(2) yes . . . N(1) C(15) C(16) 109.1(2) yes . . . N(1) C(15) C(17) 111.5(2) yes . . . N(1) C(15) C(18) 109.1(2) yes . . . C(16) C(15) C(17) 109.6(2) yes . . . C(16) C(15) C(18) 108.2(2) yes . . . C(17) C(15) C(18) 109.3(2) yes . . . P(1) C(19) C(20) 121.74(18) yes . . . P(1) C(19) C(24) 119.1(2) yes . . . C(20) C(19) C(24) 119.0(2) yes . . . C(19) C(20) C(21) 120.6(2) yes . . . C(20) C(21) C(22) 119.8(3) yes . . . C(21) C(22) C(23) 120.1(2) yes . . . C(22) C(23) C(24) 120.7(2) yes . . . C(19) C(24) C(23) 119.8(2) yes . . . P(1) C(25) C(26) 121.6(2) yes . . . P(1) C(25) C(30) 120.00(19) yes . . . C(26) C(25) C(30) 118.4(2) yes . . . C(25) C(26) C(27) 120.8(2) yes . . . C(26) C(27) C(28) 119.9(2) yes . . . C(27) C(28) C(29) 120.4(2) yes . . . C(28) C(29) C(30) 119.3(2) yes . . . C(25) C(30) C(29) 121.0(2) yes . . . C(1) C(2) H(1) 120.2 no . . . C(3) C(2) H(1) 120.0 no . . . C(2) C(3) H(2) 119.8 no . . . C(4) C(3) H(2) 119.8 no . . . C(3) C(4) H(3) 120.0 no . . . C(5) C(4) H(3) 120.0 no . . . C(4) C(5) H(4) 119.9 no . . . C(6) C(5) H(4) 119.7 no . . . N(1) C(7) H(5) 109.0 no . . . N(1) C(7) H(6) 108.8 no . . . C(6) C(7) H(5) 109.0 no . . . C(6) C(7) H(6) 108.9 no . . . H(5) C(7) H(6) 109.5 no . . . N(1) C(8) H(7) 108.4 no . . . N(1) C(8) H(8) 108.4 no . . . C(9) C(8) H(7) 108.3 no . . . C(9) C(8) H(8) 108.3 no . . . H(7) C(8) H(8) 109.5 no . . . C(9) C(10) H(9) 120.1 no . . . C(11) C(10) H(9) 120.0 no . . . C(10) C(11) H(10) 119.7 no . . . C(12) C(11) H(10) 119.8 no . . . C(11) C(12) H(11) 119.9 no . . . C(13) C(12) H(11) 119.9 no . . . C(12) C(13) H(12) 120.1 no . . . C(14) C(13) H(12) 120.0 no . . . C(15) C(16) H(13) 109.4 no . . . C(15) C(16) H(14) 109.4 no . . . C(15) C(16) H(15) 109.6 no . . . H(13) C(16) H(14) 109.5 no . . . H(13) C(16) H(15) 109.5 no . . . H(14) C(16) H(15) 109.5 no . . . C(15) C(17) H(16) 109.4 no . . . C(15) C(17) H(17) 109.5 no . . . C(15) C(17) H(18) 109.5 no . . . H(16) C(17) H(17) 109.5 no . . . H(16) C(17) H(18) 109.5 no . . . H(17) C(17) H(18) 109.5 no . . . C(15) C(18) H(19) 109.6 no . . . C(15) C(18) H(20) 109.4 no . . . C(15) C(18) H(21) 109.4 no . . . H(19) C(18) H(20) 109.5 no . . . H(19) C(18) H(21) 109.5 no . . . H(20) C(18) H(21) 109.5 no . . . C(19) C(20) H(22) 119.5 no . . . C(21) C(20) H(22) 119.9 no . . . C(20) C(21) H(23) 120.0 no . . . C(22) C(21) H(23) 120.1 no . . . C(21) C(22) H(24) 119.9 no . . . C(23) C(22) H(24) 120.0 no . . . C(22) C(23) H(25) 119.6 no . . . C(24) C(23) H(25) 119.7 no . . . C(19) C(24) H(26) 119.9 no . . . C(23) C(24) H(26) 120.3 no . . . C(25) C(26) H(27) 119.4 no . . . C(27) C(26) H(27) 119.7 no . . . C(26) C(27) H(28) 120.0 no . . . C(28) C(27) H(28) 120.1 no . . . C(27) C(28) H(29) 119.7 no . . . C(29) C(28) H(29) 119.8 no . . . C(28) C(29) H(30) 120.3 no . . . C(30) C(29) H(30) 120.4 no . . . C(25) C(30) H(31) 119.3 no . . . C(29) C(30) H(31) 119.7 no . . . #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== data_compound-6a _database_code_depnum_ccdc_archive 'CCDC 740999' _audit_creation_date 2008-03-04 _audit_creation_method 'by CrystalStructure 3.8' _audit_update_record ? #============================================================================== _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction CrystalStructure _computing_structure_solution 'DIRDIF99 (PATTY)' _computing_structure_refinement CRYSTALS _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C30 H29 Bi N O3 P ' _chemical_formula_moiety 'C30 H29 Bi N O3 P ' _chemical_formula_weight 691.52 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _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_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 +X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 11.8574(5) _cell_length_b 12.9440(5) _cell_length_c 17.2181(7) _cell_angle_alpha 90.0000 _cell_angle_beta 104.122(1) _cell_angle_gamma 90.0000 _cell_volume 2562.81(18) _cell_formula_units_Z 4 _cell_measurement_reflns_used 8399 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 28.3 _cell_measurement_temperature 153(2) #------------------------------------------------------------------------------ _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.792 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1352.00 _exptl_absorpt_coefficient_mu 6.963 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.312 _exptl_absorpt_correction_T_max 0.434 _exptl_absorpt_process_details ; SADABS; Sheldrick 1996 ; #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean '8.366 [pixels/mm]' _diffrn_ambient_temperature 153(2) _diffrn_reflns_number 15216 _diffrn_reflns_av_R_equivalents 0.020 _diffrn_reflns_theta_max 28.27 _diffrn_measured_fraction_theta_max 0.921 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.971 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 9 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 5721 _reflns_number_gt 5045 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0214 _refine_ls_wR_factor_ref 0.0488 _atom_sites_solution_primary heavy _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 5720 _refine_ls_number_parameters 354 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[0.2000\s(Fo^2^) + 0.0600]/(4Fo^2^)' _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 2.31 _refine_diff_density_min -1.18 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; Bi Bi -4.108 10.257 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; P P 0.102 0.094 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Bi(1) Bi 0.195210(10) 0.020990(10) 0.177510(10) 0.01732(2) Uani 1.00 1 d . . . P(1) P 0.26103(7) -0.23477(6) 0.13576(5) 0.02038(19) Uani 1.00 1 d . . . O(1) O 0.2272(2) -0.15639(19) 0.19086(14) 0.0279(6) Uani 1.00 1 d . . . O(2) O 0.1692(2) -0.2772(2) 0.07006(15) 0.0289(6) Uani 1.00 1 d . . . O(3) O 0.3610(2) -0.17667(18) 0.10180(14) 0.0244(5) Uani 1.00 1 d . . . N(1) N 0.0882(2) 0.1828(2) 0.19582(15) 0.0177(6) Uani 1.00 1 d . . . C(1) C 0.0101(2) -0.0053(2) 0.11223(18) 0.0191(7) Uani 1.00 1 d . . . C(2) C -0.0362(2) -0.1012(2) 0.08457(19) 0.0225(7) Uani 1.00 1 d . . . C(3) C -0.1531(3) -0.1094(2) 0.04522(19) 0.0253(8) Uani 1.00 1 d . . . C(4) C -0.2220(3) -0.0215(3) 0.0313(2) 0.0269(8) Uani 1.00 1 d . . . C(5) C -0.1754(2) 0.0741(2) 0.05745(19) 0.0242(8) Uani 1.00 1 d . . . C(6) C -0.0584(2) 0.0833(2) 0.09737(18) 0.0202(7) Uani 1.00 1 d . . . C(7) C -0.0070(2) 0.1890(2) 0.12086(19) 0.0218(7) Uani 1.00 1 d . . . C(8) C 0.0342(2) 0.1606(2) 0.26398(19) 0.0218(7) Uani 1.00 1 d . . . C(9) C 0.1007(2) 0.0833(2) 0.32419(19) 0.0196(7) Uani 1.00 1 d . . . C(10) C 0.0839(3) 0.0824(2) 0.4020(2) 0.0248(8) Uani 1.00 1 d . . . C(11) C 0.1364(3) 0.0062(2) 0.4553(2) 0.0282(9) Uani 1.00 1 d . . . C(12) C 0.2053(3) -0.0680(2) 0.4327(2) 0.0269(8) Uani 1.00 1 d . . . C(13) C 0.2226(2) -0.0677(2) 0.3551(2) 0.0232(7) Uani 1.00 1 d . . . C(14) C 0.1696(2) 0.0083(2) 0.30103(18) 0.0188(7) Uani 1.00 1 d . . . C(15) C 0.1658(2) 0.2786(2) 0.20980(19) 0.0208(7) Uani 1.00 1 d . . . C(16) C 0.2284(3) 0.2891(3) 0.1418(2) 0.0306(9) Uani 1.00 1 d . . . C(17) C 0.0962(3) 0.3774(2) 0.2127(2) 0.0289(9) Uani 1.00 1 d . . . C(18) C 0.2579(3) 0.2642(2) 0.2882(2) 0.0279(8) Uani 1.00 1 d . . . C(19) C 0.3454(2) -0.3352(2) 0.1928(2) 0.0222(7) Uani 1.00 1 d . . . C(20) C 0.3213(3) -0.3738(2) 0.2626(2) 0.0273(8) Uani 1.00 1 d . . . C(21) C 0.3820(3) -0.4570(2) 0.3020(2) 0.0307(9) Uani 1.00 1 d . . . C(22) C 0.4674(3) -0.5033(2) 0.2724(2) 0.0317(9) Uani 1.00 1 d . . . C(23) C 0.4953(3) -0.4651(2) 0.2039(2) 0.0282(9) Uani 1.00 1 d . . . C(24) C 0.4355(2) -0.3794(2) 0.1631(2) 0.0226(7) Uani 1.00 1 d . . . C(25) C 0.4672(2) -0.3352(2) 0.09275(19) 0.0216(7) Uani 1.00 1 d . . . C(26) C 0.5402(3) -0.3857(3) 0.0521(2) 0.0294(9) Uani 1.00 1 d . . . C(27) C 0.5734(3) -0.3411(3) -0.0116(2) 0.0388(11) Uani 1.00 1 d . . . C(28) C 0.5365(3) -0.2426(3) -0.0366(2) 0.0425(12) Uani 1.00 1 d . . . C(29) C 0.4657(3) -0.1898(3) 0.0021(2) 0.0349(10) Uani 1.00 1 d . . . C(30) C 0.4307(2) -0.2353(2) 0.0649(2) 0.0232(8) Uani 1.00 1 d . . . H(1) H 0.0124 -0.1606 0.0925 0.027 Uiso 1.00 1 c R . . H(2) H -0.1858 -0.1749 0.0280 0.031 Uiso 1.00 1 c R . . H(3) H -0.3014 -0.0269 0.0033 0.031 Uiso 1.00 1 c R . . H(4) H -0.2234 0.1338 0.0486 0.029 Uiso 1.00 1 c R . . H(5) H -0.0687 0.2355 0.1303 0.025 Uiso 1.00 1 c R . . H(6) H 0.0245 0.2170 0.0770 0.025 Uiso 1.00 1 c R . . H(7) H 0.0296 0.2262 0.2925 0.027 Uiso 1.00 1 c R . . H(8) H -0.0452 0.1334 0.2419 0.027 Uiso 1.00 1 c R . . H(9) H 0.0366 0.1333 0.4182 0.030 Uiso 1.00 1 c R . . H(10) H 0.1252 0.0052 0.5080 0.034 Uiso 1.00 1 c R . . H(11) H 0.2413 -0.1193 0.4700 0.031 Uiso 1.00 1 c R . . H(12) H 0.2698 -0.1189 0.3392 0.027 Uiso 1.00 1 c R . . H(13) H 0.1713 0.3045 0.0915 0.039 Uiso 1.00 1 c R . . H(14) H 0.2853 0.3453 0.1543 0.038 Uiso 1.00 1 c R . . H(15) H 0.2684 0.2243 0.1362 0.039 Uiso 1.00 1 c R . . H(16) H 0.0600 0.3741 0.2581 0.034 Uiso 1.00 1 c R . . H(17) H 0.1484 0.4372 0.2190 0.034 Uiso 1.00 1 c R . . H(18) H 0.0357 0.3844 0.1628 0.034 Uiso 1.00 1 c R . . H(19) H 0.3119 0.3228 0.2963 0.032 Uiso 1.00 1 c R . . H(20) H 0.2201 0.2606 0.3327 0.032 Uiso 1.00 1 c R . . H(21) H 0.3009 0.2001 0.2859 0.032 Uiso 1.00 1 c R . . H(22) H 0.2619 -0.3424 0.2829 0.033 Uiso 1.00 1 c R . . H(23) H 0.3651 -0.4822 0.3498 0.036 Uiso 1.00 1 c R . . H(24) H 0.5074 -0.5619 0.2989 0.037 Uiso 1.00 1 c R . . H(25) H 0.5550 -0.4970 0.1843 0.033 Uiso 1.00 1 c R . . H(26) H 0.5675 -0.4531 0.0688 0.035 Uiso 1.00 1 c R . . H(27) H 0.6223 -0.3781 -0.0381 0.048 Uiso 1.00 1 c R . . H(28) H 0.5598 -0.2118 -0.0803 0.052 Uiso 1.00 1 c R . . H(29) H 0.4404 -0.1218 -0.0144 0.042 Uiso 1.00 1 c 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Bi(1) 0.01700(6) 0.01869(6) 0.01624(6) 0.00345(5) 0.00397(4) -0.00053(5) P(1) 0.0236(4) 0.0164(3) 0.0208(3) 0.0044(3) 0.0047(3) -0.0016(3) O(1) 0.0388(14) 0.0206(12) 0.0249(12) 0.0076(10) 0.0087(10) -0.0006(9) O(2) 0.0257(12) 0.0283(13) 0.0312(13) 0.0035(10) 0.0043(10) -0.0084(10) O(3) 0.0254(12) 0.0200(11) 0.0283(12) 0.0031(9) 0.0074(9) 0.0014(9) N(1) 0.0206(13) 0.0145(12) 0.0181(12) 0.0024(10) 0.0049(10) 0.0018(10) C(1) 0.0223(15) 0.0221(16) 0.0146(13) 0.0021(12) 0.0076(11) 0.0009(11) C(2) 0.0257(16) 0.0242(16) 0.0178(14) 0.0000(13) 0.0056(12) 0.0028(12) C(3) 0.0296(17) 0.0287(18) 0.0187(15) -0.0056(14) 0.0080(13) -0.0030(13) C(4) 0.0208(16) 0.0363(19) 0.0215(15) -0.0011(14) 0.0009(12) -0.0015(14) C(5) 0.0222(16) 0.0297(18) 0.0204(15) 0.0059(13) 0.0044(12) 0.0024(13) C(6) 0.0224(15) 0.0230(16) 0.0149(13) 0.0027(12) 0.0040(11) 0.0018(12) C(7) 0.0220(16) 0.0208(16) 0.0206(15) 0.0035(12) 0.0015(12) 0.0045(12) C(8) 0.0229(16) 0.0236(16) 0.0207(15) 0.0008(13) 0.0090(12) -0.0001(12) C(9) 0.0204(15) 0.0187(15) 0.0196(14) -0.0037(12) 0.0049(11) -0.0003(12) C(10) 0.0323(18) 0.0225(17) 0.0216(15) -0.0032(13) 0.0106(13) -0.0023(12) C(11) 0.0361(19) 0.033(2) 0.0150(14) -0.0106(15) 0.0056(13) 0.0003(13) C(12) 0.0268(17) 0.0284(18) 0.0214(15) -0.0077(14) -0.0018(13) 0.0096(14) C(13) 0.0201(15) 0.0194(15) 0.0281(16) -0.0013(12) 0.0019(12) 0.0007(13) C(14) 0.0190(14) 0.0190(15) 0.0170(13) -0.0030(11) 0.0018(11) 0.0002(11) C(15) 0.0250(16) 0.0150(14) 0.0221(15) -0.0016(12) 0.0053(12) 0.0014(12) C(16) 0.036(2) 0.0280(18) 0.0324(18) -0.0074(15) 0.0170(16) 0.0007(15) C(17) 0.0360(19) 0.0181(16) 0.0316(18) 0.0034(14) 0.0064(15) 0.0014(14) C(18) 0.0269(17) 0.0214(17) 0.0316(18) -0.0024(14) -0.0001(14) -0.0004(14) C(19) 0.0244(16) 0.0177(15) 0.0230(15) 0.0001(12) 0.0029(12) -0.0022(12) C(20) 0.0284(17) 0.0258(18) 0.0286(17) -0.0017(14) 0.0086(14) -0.0017(14) C(21) 0.036(2) 0.0284(19) 0.0263(17) -0.0028(15) 0.0056(15) 0.0052(14) C(22) 0.0289(18) 0.0255(18) 0.0367(19) 0.0031(14) 0.0001(15) 0.0103(15) C(23) 0.0224(16) 0.0267(18) 0.0340(18) 0.0028(13) 0.0042(14) 0.0021(14) C(24) 0.0183(15) 0.0232(16) 0.0242(15) -0.0020(12) 0.0009(12) -0.0041(13) C(25) 0.0145(14) 0.0248(16) 0.0234(15) 0.0011(12) 0.0007(12) -0.0028(13) C(26) 0.0240(17) 0.0306(19) 0.0332(18) 0.0078(14) 0.0063(14) -0.0004(15) C(27) 0.0300(19) 0.051(2) 0.038(2) 0.0102(18) 0.0150(16) 0.0036(19) C(28) 0.033(2) 0.059(2) 0.038(2) 0.0055(19) 0.0146(17) 0.013(2) C(29) 0.0299(19) 0.035(2) 0.040(2) 0.0022(16) 0.0095(16) 0.0108(17) C(30) 0.0181(15) 0.0260(17) 0.0235(15) 0.0014(13) 0.0010(12) -0.0045(13) #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 Bi(1) O(1) 2.329(2) yes . . Bi(1) N(1) 2.508(2) yes . . Bi(1) C(1) 2.234(3) yes . . Bi(1) C(14) 2.227(3) yes . . P(1) O(1) 1.509(2) yes . . P(1) O(2) 1.472(2) yes . . P(1) O(3) 1.629(2) yes . . P(1) C(19) 1.782(3) yes . . O(3) C(30) 1.384(4) yes . . N(1) C(7) 1.496(3) yes . . N(1) C(8) 1.495(4) yes . . N(1) C(15) 1.528(4) yes . . C(1) C(2) 1.393(4) yes . . C(1) C(6) 1.393(4) yes . . C(2) C(3) 1.391(4) yes . . C(3) C(4) 1.386(5) yes . . C(4) C(5) 1.385(5) yes . . C(5) C(6) 1.394(4) yes . . C(6) C(7) 1.513(4) yes . . C(8) C(9) 1.516(4) yes . . C(9) C(10) 1.402(5) yes . . C(9) C(14) 1.388(4) yes . . C(10) C(11) 1.387(4) yes . . C(11) C(12) 1.377(5) yes . . C(12) C(13) 1.401(5) yes . . C(13) C(14) 1.394(4) yes . . C(15) C(16) 1.537(5) yes . . C(15) C(17) 1.530(4) yes . . C(15) C(18) 1.526(4) yes . . C(19) C(20) 1.394(5) yes . . C(19) C(24) 1.413(5) yes . . C(20) C(21) 1.379(4) yes . . C(21) C(22) 1.376(5) yes . . C(22) C(23) 1.392(5) yes . . C(23) C(24) 1.409(4) yes . . C(24) C(25) 1.468(5) yes . . C(25) C(26) 1.401(5) yes . . C(25) C(30) 1.410(4) yes . . C(26) C(27) 1.380(6) yes . . C(27) C(28) 1.382(6) yes . . C(28) C(29) 1.374(6) yes . . C(29) C(30) 1.383(5) yes . . C(2) H(1) 0.950 no . . C(3) H(2) 0.950 no . . C(4) H(3) 0.950 no . . C(5) H(4) 0.950 no . . C(7) H(5) 0.990 no . . C(7) H(6) 0.990 no . . C(8) H(7) 0.990 no . . C(8) H(8) 0.990 no . . C(10) H(9) 0.950 no . . C(11) H(10) 0.950 no . . C(12) H(11) 0.950 no . . C(13) H(12) 0.950 no . . C(16) H(13) 0.980 no . . C(16) H(14) 0.980 no . . C(16) H(15) 0.980 no . . C(17) H(16) 0.980 no . . C(17) H(17) 0.980 no . . C(17) H(18) 0.980 no . . C(18) H(19) 0.980 no . . C(18) H(20) 0.980 no . . C(18) H(21) 0.980 no . . C(20) H(22) 0.950 no . . C(21) H(23) 0.950 no . . C(22) H(24) 0.950 no . . C(23) H(25) 0.950 no . . C(26) H(26) 0.950 no . . C(27) H(27) 0.950 no . . C(28) H(28) 0.950 no . . C(29) H(29) 0.950 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 O(1) Bi(1) N(1) 152.36(9) yes . . . O(1) Bi(1) C(1) 90.90(10) yes . . . O(1) Bi(1) C(14) 83.69(10) yes . . . N(1) Bi(1) C(1) 74.08(10) yes . . . N(1) Bi(1) C(14) 75.54(10) yes . . . C(1) Bi(1) C(14) 97.07(11) yes . . . O(1) P(1) O(2) 118.28(14) yes . . . O(1) P(1) O(3) 104.11(13) yes . . . O(1) P(1) C(19) 110.09(15) yes . . . O(2) P(1) O(3) 111.30(14) yes . . . O(2) P(1) C(19) 111.27(14) yes . . . O(3) P(1) C(19) 100.04(14) yes . . . Bi(1) O(1) P(1) 131.51(14) yes . . . P(1) O(3) C(30) 118.7(2) yes . . . Bi(1) N(1) C(7) 103.62(18) yes . . . Bi(1) N(1) C(8) 105.36(18) yes . . . Bi(1) N(1) C(15) 113.23(19) yes . . . C(7) N(1) C(8) 108.1(2) yes . . . C(7) N(1) C(15) 113.0(2) yes . . . C(8) N(1) C(15) 112.9(2) yes . . . Bi(1) C(1) C(2) 124.4(2) yes . . . Bi(1) C(1) C(6) 115.1(2) yes . . . C(2) C(1) C(6) 120.5(2) yes . . . C(1) C(2) C(3) 119.8(3) yes . . . C(2) C(3) C(4) 119.8(3) yes . . . C(3) C(4) C(5) 120.3(3) yes . . . C(4) C(5) C(6) 120.4(3) yes . . . C(1) C(6) C(5) 119.1(2) yes . . . C(1) C(6) C(7) 121.1(2) yes . . . C(5) C(6) C(7) 119.8(2) yes . . . N(1) C(7) C(6) 110.6(2) yes . . . N(1) C(8) C(9) 114.4(2) yes . . . C(8) C(9) C(10) 119.2(3) yes . . . C(8) C(9) C(14) 120.6(2) yes . . . C(10) C(9) C(14) 119.9(2) yes . . . C(9) C(10) C(11) 119.5(3) yes . . . C(10) C(11) C(12) 120.7(3) yes . . . C(11) C(12) C(13) 120.1(3) yes . . . C(12) C(13) C(14) 119.5(3) yes . . . Bi(1) C(14) C(9) 116.7(2) yes . . . Bi(1) C(14) C(13) 123.1(2) yes . . . C(9) C(14) C(13) 120.2(3) yes . . . N(1) C(15) C(16) 109.6(2) yes . . . N(1) C(15) C(17) 112.1(2) yes . . . N(1) C(15) C(18) 108.3(2) yes . . . C(16) C(15) C(17) 108.4(2) yes . . . C(16) C(15) C(18) 108.0(2) yes . . . C(17) C(15) C(18) 110.4(2) yes . . . P(1) C(19) C(20) 122.0(2) yes . . . P(1) C(19) C(24) 117.9(2) yes . . . C(20) C(19) C(24) 120.0(3) yes . . . C(19) C(20) C(21) 120.8(3) yes . . . C(20) C(21) C(22) 120.0(3) yes . . . C(21) C(22) C(23) 120.5(3) yes . . . C(22) C(23) C(24) 120.5(3) yes . . . C(19) C(24) C(23) 118.1(3) yes . . . C(19) C(24) C(25) 120.6(2) yes . . . C(23) C(24) C(25) 121.3(3) yes . . . C(24) C(25) C(26) 123.0(3) yes . . . C(24) C(25) C(30) 121.2(3) yes . . . C(26) C(25) C(30) 115.7(3) yes . . . C(25) C(26) C(27) 122.2(3) yes . . . C(26) C(27) C(28) 120.3(4) yes . . . C(27) C(28) C(29) 119.5(4) yes . . . C(28) C(29) C(30) 120.2(3) yes . . . O(3) C(30) C(25) 121.0(3) yes . . . O(3) C(30) C(29) 116.9(3) yes . . . C(25) C(30) C(29) 122.1(3) yes . . . C(1) C(2) H(1) 119.8 no . . . C(3) C(2) H(1) 120.4 no . . . C(2) C(3) H(2) 120.1 no . . . C(4) C(3) H(2) 120.1 no . . . C(3) C(4) H(3) 119.8 no . . . C(5) C(4) H(3) 119.9 no . . . C(4) C(5) H(4) 119.9 no . . . C(6) C(5) H(4) 119.7 no . . . N(1) C(7) H(5) 108.9 no . . . N(1) C(7) H(6) 109.4 no . . . C(6) C(7) H(5) 109.2 no . . . C(6) C(7) H(6) 109.3 no . . . H(5) C(7) H(6) 109.5 no . . . N(1) C(8) H(7) 108.1 no . . . N(1) C(8) H(8) 108.5 no . . . C(9) C(8) H(7) 108.0 no . . . C(9) C(8) H(8) 108.4 no . . . H(7) C(8) H(8) 109.5 no . . . C(9) C(10) H(9) 120.4 no . . . C(11) C(10) H(9) 120.1 no . . . C(10) C(11) H(10) 119.8 no . . . C(12) C(11) H(10) 119.5 no . . . C(11) C(12) H(11) 119.8 no . . . C(13) C(12) H(11) 120.1 no . . . C(12) C(13) H(12) 120.3 no . . . C(14) C(13) H(12) 120.1 no . . . C(15) C(16) H(13) 109.5 no . . . C(15) C(16) H(14) 109.4 no . . . C(15) C(16) H(15) 109.5 no . . . H(13) C(16) H(14) 109.5 no . . . H(13) C(16) H(15) 109.5 no . . . H(14) C(16) H(15) 109.5 no . . . C(15) C(17) H(16) 109.5 no . . . C(15) C(17) H(17) 109.4 no . . . C(15) C(17) H(18) 109.5 no . . . H(16) C(17) H(17) 109.5 no . . . H(16) C(17) H(18) 109.5 no . . . H(17) C(17) H(18) 109.5 no . . . C(15) C(18) H(19) 109.5 no . . . C(15) C(18) H(20) 109.4 no . . . C(15) C(18) H(21) 109.5 no . . . H(19) C(18) H(20) 109.5 no . . . H(19) C(18) H(21) 109.5 no . . . H(20) C(18) H(21) 109.5 no . . . C(19) C(20) H(22) 119.4 no . . . C(21) C(20) H(22) 119.8 no . . . C(20) C(21) H(23) 119.9 no . . . C(22) C(21) H(23) 120.1 no . . . C(21) C(22) H(24) 119.7 no . . . C(23) C(22) H(24) 119.8 no . . . C(22) C(23) H(25) 120.0 no . . . C(24) C(23) H(25) 119.5 no . . . C(25) C(26) H(26) 118.9 no . . . C(27) C(26) H(26) 118.9 no . . . C(26) C(27) H(27) 119.7 no . . . C(28) C(27) H(27) 120.0 no . . . C(27) C(28) H(28) 120.1 no . . . C(29) C(28) H(28) 120.4 no . . . C(28) C(29) H(29) 120.0 no . . . C(30) C(29) H(29) 119.7 no . . . #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #==============================================================================