# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Yunlong Fu' _publ_contact_author_email YUNLONGFU@DNS.SXNU.EDU.CN _publ_section_title ; Synthesis and Structural Characterization of Four New Organically Directed Bismuth Sulfates ; loop_ _publ_author_name 'Fu Yunlong.' 'Zhiwei Xu.' 'Yu Zhang.' # Attachment 'I-en-revised.cif' data_bb _database_code_depnum_ccdc_archive 'CCDC 675233' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H42 Bi2 N6 O30 S6' _chemical_formula_weight 1288.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.5542(5) _cell_length_b 26.373(2) _cell_length_c 10.0681(8) _cell_angle_alpha 90.00 _cell_angle_beta 104.5340(10) _cell_angle_gamma 90.00 _cell_volume 1684.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description column _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.541 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1244 _exptl_absorpt_coefficient_mu 10.920 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.1710 _exptl_absorpt_correction_T_max 0.6692 _exptl_absorpt_process_details ? _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8561 _diffrn_reflns_av_R_equivalents 0.0366 _diffrn_reflns_av_sigmaI/netI 0.0450 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3050 _reflns_number_gt 2705 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0265P)^2^+0.8600P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3050 _refine_ls_number_parameters 253 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0372 _refine_ls_R_factor_gt 0.0311 _refine_ls_wR_factor_ref 0.0644 _refine_ls_wR_factor_gt 0.0621 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Bi1 Bi 0.54239(3) 0.324522(9) 0.45969(2) 0.01381(8) Uani 1 1 d . . . S1 S 0.4098(2) 0.43405(6) 0.24699(15) 0.0177(3) Uani 1 1 d . . . S2 S 0.5325(2) 0.24977(6) 0.71289(15) 0.0161(3) Uani 1 1 d . . . S3 S 1.0408(2) 0.34458(6) 0.53864(15) 0.0166(3) Uani 1 1 d . . . O1 O 0.4345(7) 0.46247(17) 0.3760(4) 0.0270(10) Uani 1 1 d . . . O2 O 0.2006(7) 0.44427(18) 0.1591(5) 0.0306(11) Uani 1 1 d . . . O3 O 0.5737(7) 0.44636(18) 0.1800(5) 0.0310(11) Uani 1 1 d . . . O4 O 0.4219(7) 0.37804(17) 0.2791(4) 0.0278(11) Uani 1 1 d . . . O5 O 0.5618(7) 0.30524(17) 0.7202(4) 0.0252(10) Uani 1 1 d . . . O6 O 0.3565(6) 0.23414(16) 0.7717(4) 0.0198(10) Uani 1 1 d . . . O7 O 0.4926(6) 0.23503(17) 0.5678(4) 0.0218(10) Uani 1 1 d . . . O8 O 1.1781(6) 0.32646(17) 0.4526(4) 0.0254(11) Uani 1 1 d . . . O9 O 1.1584(6) 0.37650(19) 0.6492(5) 0.0312(12) Uani 1 1 d . . . O10 O 0.9430(7) 0.30135(19) 0.5910(5) 0.0300(11) Uani 1 1 d . . . O11 O 0.8648(6) 0.37404(17) 0.4505(4) 0.0243(10) Uani 1 1 d . . . O12 O 0.7212(6) 0.27622(16) 0.2958(4) 0.0224(10) Uani 1 1 d . . . O13 O 0.5313(8) 0.40174(17) 0.5851(5) 0.0252(10) Uani 1 1 d D . . O14 O 0.5293(10) 0.3854(3) 0.9101(7) 0.075(2) Uani 1 1 d D . . O15 O 0.2326(9) 0.4685(2) 0.8926(5) 0.0408(13) Uani 1 1 d D . . C1 C 1.0160(10) 0.3390(3) -0.0481(7) 0.0258(15) Uani 1 1 d . . . H1A H 0.8988 0.3547 -0.1133 0.031 Uiso 1 1 calc R . . H1B H 1.1317 0.3630 -0.0268 0.031 Uiso 1 1 calc R . . C2 C 0.9514(10) 0.3254(3) 0.0806(7) 0.0262(15) Uani 1 1 d . . . H2A H 0.8419 0.2997 0.0597 0.031 Uiso 1 1 calc R . . H2B H 1.0713 0.3113 0.1472 0.031 Uiso 1 1 calc R . . C3 C 1.0535(11) 0.4996(3) 0.5765(6) 0.0294(16) Uani 1 1 d . . . H3A H 1.1901 0.4833 0.5916 0.035 Uiso 1 1 calc R . . H3B H 1.0751 0.5340 0.6111 0.035 Uiso 1 1 calc R . . N1 N 1.0818(8) 0.2927(2) -0.1084(5) 0.0262(13) Uani 1 1 d . . . H4C H 1.2051 0.2821 -0.0565 0.039 Uiso 1 1 calc R . . H4D H 1.0945 0.2994 -0.1926 0.039 Uiso 1 1 calc R . . H4E H 0.9853 0.2685 -0.1126 0.039 Uiso 1 1 calc R . . N2 N 0.8726(8) 0.3704(2) 0.1397(5) 0.0287(14) Uani 1 1 d . . . H5A H 0.9696 0.3947 0.1532 0.043 Uiso 1 1 calc R . . H5B H 0.8460 0.3621 0.2193 0.043 Uiso 1 1 calc R . . H5C H 0.7548 0.3814 0.0821 0.043 Uiso 1 1 calc R . . N3 N 0.9202(8) 0.4716(2) 0.6499(5) 0.0277(13) Uani 1 1 d . . . H6C H 0.8941 0.4407 0.6142 0.042 Uiso 1 1 calc R . . H6D H 0.7992 0.4881 0.6415 0.042 Uiso 1 1 calc R . . H6E H 0.9869 0.4691 0.7383 0.042 Uiso 1 1 calc R . . H3 H 0.524(16) 0.363(3) 0.842(8) 0.10(4) Uiso 1 1 d D . . H4 H 0.424(8) 0.407(2) 0.902(7) 0.03(2) Uiso 1 1 d D . . H5 H 0.21(2) 0.459(5) 0.974(7) 0.16(6) Uiso 1 1 d D . . H6 H 0.182(19) 0.497(3) 0.849(12) 0.15(6) Uiso 1 1 d D . . H1 H 0.42(3) 0.417(12) 0.53(2) 0.5(2) Uiso 1 1 d D . . H2 H 0.666(11) 0.404(8) 0.634(18) 0.29(10) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi1 0.01350(13) 0.01250(14) 0.01570(13) -0.00048(10) 0.00419(8) -0.00033(9) S1 0.0193(8) 0.0147(9) 0.0187(8) 0.0020(6) 0.0043(6) 0.0011(6) S2 0.0164(7) 0.0166(9) 0.0159(7) 0.0029(6) 0.0052(6) 0.0015(6) S3 0.0131(7) 0.0165(9) 0.0210(8) -0.0030(6) 0.0054(6) 0.0003(6) O1 0.036(3) 0.020(3) 0.025(2) -0.001(2) 0.006(2) 0.006(2) O2 0.027(3) 0.029(3) 0.031(3) 0.006(2) -0.001(2) 0.004(2) O3 0.033(3) 0.028(3) 0.036(3) 0.001(2) 0.017(2) -0.003(2) O4 0.039(3) 0.013(3) 0.026(2) 0.0037(19) -0.001(2) 0.002(2) O5 0.031(2) 0.015(3) 0.028(3) 0.001(2) 0.006(2) 0.001(2) O6 0.011(2) 0.025(3) 0.023(2) -0.0005(19) 0.0040(17) -0.0012(18) O7 0.030(2) 0.021(3) 0.015(2) -0.0010(18) 0.0063(18) 0.0010(19) O8 0.016(2) 0.037(3) 0.026(2) -0.011(2) 0.0081(18) -0.0014(19) O9 0.019(2) 0.038(3) 0.036(3) -0.019(2) 0.008(2) -0.002(2) O10 0.035(3) 0.028(3) 0.030(3) 0.010(2) 0.012(2) -0.001(2) O11 0.017(2) 0.020(3) 0.036(3) 0.005(2) 0.0066(19) 0.0032(18) O12 0.017(2) 0.026(3) 0.024(2) -0.0047(19) 0.0030(18) -0.0028(18) O13 0.033(3) 0.014(3) 0.029(3) -0.006(2) 0.007(2) 0.002(2) O14 0.058(4) 0.095(6) 0.055(4) -0.035(4) -0.015(3) 0.043(4) O15 0.051(3) 0.039(4) 0.026(3) 0.008(3) -0.002(2) -0.002(3) C1 0.028(4) 0.017(4) 0.036(4) -0.002(3) 0.015(3) -0.001(3) C2 0.029(4) 0.021(4) 0.031(4) -0.001(3) 0.012(3) -0.001(3) C3 0.031(4) 0.027(4) 0.031(4) -0.007(3) 0.009(3) -0.005(3) N1 0.028(3) 0.022(4) 0.030(3) -0.003(3) 0.011(2) 0.004(2) N2 0.026(3) 0.039(4) 0.025(3) -0.005(3) 0.014(2) 0.004(3) N3 0.032(3) 0.019(3) 0.033(3) -0.001(3) 0.010(2) 0.006(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Bi1 O4 2.280(4) . ? Bi1 O8 2.371(4) 1_455 ? Bi1 O13 2.407(4) . ? Bi1 O11 2.505(4) . ? Bi1 O6 2.510(4) 4_565 ? Bi1 O12 2.586(4) . ? Bi1 O5 2.643(4) . ? Bi1 O7 2.654(4) . ? Bi1 O10 2.697(4) . ? S1 O3 1.442(4) . ? S1 O2 1.458(4) . ? S1 O1 1.473(4) . ? S1 O4 1.510(5) . ? S2 O7 1.470(4) . ? S2 O5 1.475(5) . ? S2 O12 1.476(4) 4_566 ? S2 O6 1.481(4) . ? S3 O9 1.453(4) . ? S3 O10 1.469(5) . ? S3 O8 1.476(4) . ? S3 O11 1.486(4) . ? O6 Bi1 2.510(4) 4_566 ? O8 Bi1 2.371(4) 1_655 ? O12 S2 1.476(4) 4_565 ? O13 H1 0.90(2) . ? O13 H2 0.90(2) . ? O14 H3 0.90(2) . ? O14 H4 0.88(2) . ? O15 H5 0.90(2) . ? O15 H6 0.90(2) . ? C1 N1 1.476(8) . ? C1 C2 1.504(9) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 N2 1.477(8) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N3 1.476(8) . ? C3 C3 1.524(12) 3_766 ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? N1 H4C 0.8900 . ? N1 H4D 0.8900 . ? N1 H4E 0.8900 . ? N2 H5A 0.8900 . ? N2 H5B 0.8900 . ? N2 H5C 0.8900 . ? N3 H6C 0.8900 . ? N3 H6D 0.8900 . ? N3 H6E 0.8900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Bi1 O8 79.53(16) . 1_455 ? O4 Bi1 O13 81.06(16) . . ? O8 Bi1 O13 80.48(15) 1_455 . ? O4 Bi1 O11 76.96(15) . . ? O8 Bi1 O11 147.12(14) 1_455 . ? O13 Bi1 O11 73.46(15) . . ? O4 Bi1 O6 76.99(15) . 4_565 ? O8 Bi1 O6 72.32(13) 1_455 4_565 ? O13 Bi1 O6 147.57(15) . 4_565 ? O11 Bi1 O6 123.20(14) . 4_565 ? O4 Bi1 O12 85.29(15) . . ? O8 Bi1 O12 127.27(13) 1_455 . ? O13 Bi1 O12 146.07(15) . . ? O11 Bi1 O12 73.25(14) . . ? O6 Bi1 O12 55.06(12) 4_565 . ? O4 Bi1 O5 146.20(15) . . ? O8 Bi1 O5 80.28(14) 1_455 . ? O13 Bi1 O5 69.05(15) . . ? O11 Bi1 O5 107.81(14) . . ? O6 Bi1 O5 121.53(13) 4_565 . ? O12 Bi1 O5 128.44(13) . . ? O4 Bi1 O7 145.49(14) . . ? O8 Bi1 O7 78.74(14) 1_455 . ? O13 Bi1 O7 120.94(14) . . ? O11 Bi1 O7 132.11(13) . . ? O6 Bi1 O7 71.03(13) 4_565 . ? O12 Bi1 O7 86.90(13) . . ? O5 Bi1 O7 53.27(13) . . ? O4 Bi1 O10 129.11(15) . . ? O8 Bi1 O10 150.30(14) 1_455 . ? O13 Bi1 O10 95.08(16) . . ? O11 Bi1 O10 53.83(13) . . ? O6 Bi1 O10 117.29(14) 4_565 . ? O12 Bi1 O10 70.12(13) . . ? O5 Bi1 O10 70.82(13) . . ? O7 Bi1 O10 78.59(13) . . ? O3 S1 O2 111.8(3) . . ? O3 S1 O1 111.6(3) . . ? O2 S1 O1 108.6(3) . . ? O3 S1 O4 108.4(3) . . ? O2 S1 O4 107.6(3) . . ? O1 S1 O4 108.7(3) . . ? O7 S2 O5 107.5(3) . . ? O7 S2 O12 110.7(2) . 4_566 ? O5 S2 O12 110.6(3) . 4_566 ? O7 S2 O6 111.2(2) . . ? O5 S2 O6 111.1(2) . . ? O12 S2 O6 105.7(2) 4_566 . ? O9 S3 O10 111.7(3) . . ? O9 S3 O8 110.6(2) . . ? O10 S3 O8 110.1(3) . . ? O9 S3 O11 109.7(3) . . ? O10 S3 O11 106.1(3) . . ? O8 S3 O11 108.4(3) . . ? S1 O4 Bi1 139.9(3) . . ? S2 O5 Bi1 99.7(2) . . ? S2 O6 Bi1 101.17(19) . 4_566 ? S2 O7 Bi1 99.4(2) . . ? S3 O8 Bi1 138.3(3) . 1_655 ? S3 O10 Bi1 96.2(2) . . ? S3 O11 Bi1 103.9(2) . . ? S2 O12 Bi1 98.06(19) 4_565 . ? Bi1 O13 H1 100(10) . . ? Bi1 O13 H2 101(10) . . ? H1 O13 H2 148(10) . . ? H3 O14 H4 118(8) . . ? H5 O15 H6 123(10) . . ? N1 C1 C2 109.4(6) . . ? N1 C1 H1A 109.8 . . ? C2 C1 H1A 109.8 . . ? N1 C1 H1B 109.8 . . ? C2 C1 H1B 109.8 . . ? H1A C1 H1B 108.2 . . ? N2 C2 C1 111.0(6) . . ? N2 C2 H2A 109.4 . . ? C1 C2 H2A 109.4 . . ? N2 C2 H2B 109.4 . . ? C1 C2 H2B 109.4 . . ? H2A C2 H2B 108.0 . . ? N3 C3 C3 109.5(7) . 3_766 ? N3 C3 H3A 109.8 . . ? C3 C3 H3A 109.8 3_766 . ? N3 C3 H3B 109.8 . . ? C3 C3 H3B 109.8 3_766 . ? H3A C3 H3B 108.2 . . ? C1 N1 H4C 109.5 . . ? C1 N1 H4D 109.5 . . ? H4C N1 H4D 109.5 . . ? C1 N1 H4E 109.5 . . ? H4C N1 H4E 109.5 . . ? H4D N1 H4E 109.5 . . ? C2 N2 H5A 109.5 . . ? C2 N2 H5B 109.5 . . ? H5A N2 H5B 109.5 . . ? C2 N2 H5C 109.5 . . ? H5A N2 H5C 109.5 . . ? H5B N2 H5C 109.5 . . ? C3 N3 H6C 109.5 . . ? C3 N3 H6D 109.5 . . ? H6C N3 H6D 109.5 . . ? C3 N3 H6E 109.5 . . ? H6C N3 H6E 109.5 . . ? H6D N3 H6E 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H4C O7 0.89 2.03 2.921(7) 174.5 4_665 N1 H4D O10 0.89 2.16 2.942(7) 146.9 1_554 N1 H4E O12 0.89 2.11 2.945(7) 156.4 4_565 N2 H5A O2 0.89 1.99 2.872(7) 171.0 1_655 N2 H5B O11 0.89 2.32 3.144(7) 153.8 . N2 H5B O12 0.89 2.59 3.225(7) 129.1 . N2 H5C O14 0.89 1.98 2.820(8) 157.5 1_554 N2 H5C O3 0.89 2.43 2.902(7) 113.5 . N3 H6C O9 0.89 2.38 2.956(7) 122.1 . N3 H6C O11 0.89 2.38 3.228(7) 158.2 . N3 H6C O13 0.89 2.54 3.080(7) 119.8 . N3 H6D O1 0.89 1.98 2.862(7) 168.2 3_666 N3 H6E O15 0.89 1.94 2.767(7) 154.6 1_655 O14 H3 O5 0.90(2) 2.01(3) 2.893(8) 167(10) . O15 H5 O2 0.90(2) 1.92(3) 2.817(7) 171(13) 1_556 O15 H6 O3 0.90(2) 2.26(12) 2.767(7) 116(10) 3_666 O13 H1 O1 0.90(2) 2.0(2) 2.594(7) 125(24) . O13 H2 N3 0.90(2) 2.41(16) 3.080(7) 131(17) . _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.864 _refine_diff_density_min -1.299 _refine_diff_density_rms 0.166 # Attachment 'II-N-Pip-revised.cif' data_aa _database_code_depnum_ccdc_archive 'CCDC 675234' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H19 Bi N2 O14 S3' _chemical_formula_weight 636.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.5483(4) _cell_length_b 24.8079(17) _cell_length_c 10.1736(7) _cell_angle_alpha 90.00 _cell_angle_beta 102.5450(10) _cell_angle_gamma 90.00 _cell_volume 1613.24(19) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description column _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.620 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1224 _exptl_absorpt_coefficient_mu 11.396 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.1426 _exptl_absorpt_correction_T_max 0.6585 _exptl_absorpt_process_details ? _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7112 _diffrn_reflns_av_R_equivalents 0.0365 _diffrn_reflns_av_sigmaI/netI 0.0540 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 25.99 _reflns_number_total 3068 _reflns_number_gt 2799 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0562P)^2^+2.7169P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3068 _refine_ls_number_parameters 249 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0396 _refine_ls_R_factor_gt 0.0358 _refine_ls_wR_factor_ref 0.0974 _refine_ls_wR_factor_gt 0.0944 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.489 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Bi1 Bi 0.44166(5) 0.328461(14) 0.99680(3) 0.01835(17) Uani 1 1 d D . . O1 O 0.4186(19) 0.4687(5) 1.2049(17) 0.112(6) Uani 1 1 d U . . O2 O 0.7465(18) 0.4478(4) 1.3406(9) 0.067(3) Uani 1 1 d . . . O3 O 0.5710(11) 0.3824(3) 1.1866(7) 0.0306(16) Uani 1 1 d . . . O4 O 0.701(3) 0.4635(6) 1.1047(11) 0.111(6) Uani 1 1 d . . . O5 O 0.4543(12) 0.3188(3) 0.7286(8) 0.0361(18) Uani 1 1 d D . . O6 O 0.4773(11) 0.2425(3) 0.8628(6) 0.0284(16) Uani 1 1 d . . . O7 O 0.6356(11) 0.2380(3) 0.6687(7) 0.0280(16) Uani 1 1 d . . . O8 O 0.2682(10) 0.2372(3) 0.6343(6) 0.0258(15) Uani 1 1 d . . . O9 O 0.0698(11) 0.3194(3) 0.8587(7) 0.0257(15) Uani 1 1 d . . . O10 O -0.1392(10) 0.4008(3) 0.8467(7) 0.0292(16) Uani 1 1 d . . . O11 O 0.1319(10) 0.3789(3) 1.0429(7) 0.0295(16) Uani 1 1 d . . . O12 O 0.4461(12) 0.4128(3) 0.8744(7) 0.0286(16) Uani 1 1 d D . . O13 O -0.1918(11) 0.3282(3) 0.9926(8) 0.0285(17) Uani 1 1 d . . . O14 O 0.068(2) 0.5002(6) 0.204(3) 0.059(9) Uani 0.59(4) 1 d P A 1 O14' O 0.041(3) 0.4972(8) 0.096(4) 0.048(9) Uani 0.41(4) 1 d P A 2 S1 S 0.6103(4) 0.44063(11) 1.2131(2) 0.0273(5) Uani 1 1 d . . . S2 S 0.4600(3) 0.26043(10) 0.7213(2) 0.0193(5) Uani 1 1 d . . . S3 S -0.0351(3) 0.35749(9) 0.9351(2) 0.0185(5) Uani 1 1 d . . . C1 C 0.1868(16) 0.3519(4) 0.3965(10) 0.029(2) Uani 1 1 d . . . H1A H 0.2397 0.3649 0.3202 0.035 Uiso 1 1 calc R . . H1B H 0.3003 0.3338 0.4576 0.035 Uiso 1 1 calc R . . C2 C 0.0124(17) 0.3129(5) 0.3485(11) 0.034(2) Uani 1 1 d . . . H2A H 0.0645 0.2820 0.3075 0.041 Uiso 1 1 calc R . . H2B H -0.0958 0.3300 0.2810 0.041 Uiso 1 1 calc R . . C3 C 0.0173(17) 0.3808(5) 0.5782(10) 0.034(2) Uani 1 1 d . . . H3A H -0.0390 0.4119 0.6162 0.040 Uiso 1 1 calc R . . H3B H 0.1240 0.3648 0.6485 0.040 Uiso 1 1 calc R . . C4 C -0.1540(18) 0.3407(5) 0.5325(12) 0.039(3) Uani 1 1 d . . . H4A H -0.2055 0.3280 0.6094 0.047 Uiso 1 1 calc R . . H4B H -0.2690 0.3579 0.4705 0.047 Uiso 1 1 calc R . . C5 C 0.288(2) 0.4373(6) 0.5188(13) 0.054(4) Uani 1 1 d . . . H5A H 0.3922 0.4199 0.5862 0.081 Uiso 1 1 calc R . . H5B H 0.2340 0.4681 0.5576 0.081 Uiso 1 1 calc R . . H5C H 0.3490 0.4488 0.4459 0.081 Uiso 1 1 calc R . . N1 N 0.1137(14) 0.3988(4) 0.4671(8) 0.0282(19) Uani 1 1 d . . . N2 N -0.0783(14) 0.2948(4) 0.4657(10) 0.039(2) Uani 1 1 d . . . H2C H -0.1848 0.2718 0.4359 0.047 Uiso 1 1 calc R . . H2D H 0.0204 0.2770 0.5255 0.047 Uiso 1 1 calc R . . H1 H 0.011(15) 0.413(4) 0.410(9) 0.01(2) Uiso 1 1 d . . . H2 H 0.581(13) 0.417(9) 0.87(4) 0.3(2) Uiso 1 1 d D . . H3 H 0.447(16) 0.439(3) 0.920(8) 0.01(3) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi1 0.0167(2) 0.0173(3) 0.0215(2) 0.00133(12) 0.00511(15) -0.00010(12) O1 0.060(7) 0.042(7) 0.209(16) -0.017(8) -0.029(9) 0.021(6) O2 0.094(7) 0.037(6) 0.049(5) -0.015(4) -0.030(5) 0.015(5) O3 0.039(4) 0.022(4) 0.028(3) -0.003(3) 0.000(3) -0.001(3) O4 0.165(14) 0.119(11) 0.060(7) -0.021(7) 0.051(8) -0.100(11) O5 0.032(4) 0.019(4) 0.054(5) 0.003(3) 0.004(4) 0.000(3) O6 0.030(4) 0.032(4) 0.023(3) -0.003(3) 0.006(3) -0.003(3) O7 0.023(3) 0.031(4) 0.031(4) -0.006(3) 0.008(3) 0.002(3) O8 0.017(3) 0.032(4) 0.028(3) -0.006(3) 0.004(3) 0.001(3) O9 0.027(4) 0.025(4) 0.027(3) -0.002(3) 0.011(3) 0.006(3) O10 0.025(3) 0.029(4) 0.036(4) 0.010(3) 0.012(3) 0.005(3) O11 0.023(3) 0.036(5) 0.029(3) -0.004(3) 0.004(3) -0.003(3) O12 0.034(4) 0.021(4) 0.031(4) 0.000(3) 0.007(3) 0.000(3) O13 0.017(3) 0.034(5) 0.036(4) 0.013(3) 0.009(3) 0.001(3) O14 0.046(9) 0.042(11) 0.09(2) 0.010(9) 0.025(9) -0.005(8) O14' 0.057(13) 0.033(14) 0.06(2) 0.000(10) 0.022(11) -0.007(11) S1 0.0301(12) 0.0225(14) 0.0269(12) -0.0019(10) 0.0012(9) -0.0002(10) S2 0.0181(10) 0.0203(12) 0.0192(10) -0.0036(9) 0.0035(8) 0.0001(9) S3 0.0148(10) 0.0190(13) 0.0231(11) 0.0013(9) 0.0070(8) 0.0003(9) C1 0.032(5) 0.028(6) 0.030(5) -0.002(4) 0.012(4) 0.001(5) C2 0.032(6) 0.028(6) 0.039(6) -0.014(5) 0.002(5) 0.005(5) C3 0.040(6) 0.037(7) 0.026(5) -0.001(4) 0.012(4) 0.008(5) C4 0.028(6) 0.049(8) 0.043(7) 0.011(6) 0.017(5) 0.000(5) C5 0.063(8) 0.045(8) 0.052(7) -0.009(6) 0.008(6) -0.029(7) N1 0.033(4) 0.026(5) 0.026(4) -0.001(4) 0.006(4) 0.000(4) N2 0.026(5) 0.024(5) 0.062(6) 0.007(5) -0.002(4) 0.000(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Bi1 O3 2.350(7) . ? Bi1 O13 2.410(7) 1_655 ? Bi1 O12 2.438(7) . ? Bi1 O11 2.513(7) . ? Bi1 O7 2.535(7) 4_566 ? Bi1 O9 2.543(7) . ? Bi1 O8 2.567(6) 4_566 ? Bi1 O6 2.568(7) . ? Bi1 O5 2.759(8) . ? O1 S1 1.422(12) . ? O2 S1 1.417(8) . ? O3 S1 1.482(8) . ? O4 S1 1.474(11) . ? O5 S2 1.451(8) . ? O6 S2 1.487(7) . ? O7 S2 1.479(7) . ? O7 Bi1 2.535(7) 4_565 ? O8 S2 1.486(7) . ? O8 Bi1 2.567(6) 4_565 ? O9 S3 1.483(7) . ? O10 S3 1.470(7) . ? O11 S3 1.470(7) . ? O12 H2 0.90(3) . ? O12 H3 0.79(3) . ? O13 S3 1.478(7) . ? O13 Bi1 2.410(7) 1_455 ? C1 C2 1.496(15) . ? C1 N1 1.498(13) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 N2 1.512(15) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N1 1.477(13) . ? C3 C4 1.496(17) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 N2 1.468(16) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 N1 1.493(14) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? N1 H1 0.87(10) . ? N2 H2C 0.9000 . ? N2 H2D 0.9000 . ? 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 O3 Bi1 O13 80.4(3) . 1_655 ? O3 Bi1 O12 83.6(2) . . ? O13 Bi1 O12 82.6(2) 1_655 . ? O3 Bi1 O11 74.0(2) . . ? O13 Bi1 O11 148.5(2) 1_655 . ? O12 Bi1 O11 76.6(2) . . ? O3 Bi1 O7 76.5(3) . 4_566 ? O13 Bi1 O7 70.0(2) 1_655 4_566 ? O12 Bi1 O7 148.3(2) . 4_566 ? O11 Bi1 O7 119.9(2) . 4_566 ? O3 Bi1 O9 129.4(2) . . ? O13 Bi1 O9 145.9(2) 1_655 . ? O12 Bi1 O9 84.8(2) . . ? O11 Bi1 O9 55.4(2) . . ? O7 Bi1 O9 126.9(2) 4_566 . ? O3 Bi1 O8 92.1(2) . 4_566 ? O13 Bi1 O8 124.6(2) 1_655 4_566 ? O12 Bi1 O8 151.5(2) . 4_566 ? O11 Bi1 O8 75.1(2) . 4_566 ? O7 Bi1 O8 55.0(2) 4_566 4_566 ? O9 Bi1 O8 76.2(2) . 4_566 ? O3 Bi1 O6 148.3(2) . . ? O13 Bi1 O6 77.5(2) 1_655 . ? O12 Bi1 O6 115.4(3) . . ? O11 Bi1 O6 133.0(2) . . ? O7 Bi1 O6 74.7(2) 4_566 . ? O9 Bi1 O6 79.6(2) . . ? O8 Bi1 O6 82.2(2) 4_566 . ? O3 Bi1 O5 141.2(2) . . ? O13 Bi1 O5 74.8(2) 1_655 . ? O12 Bi1 O5 64.1(2) . . ? O11 Bi1 O5 115.3(2) . . ? O7 Bi1 O5 120.5(2) 4_566 . ? O9 Bi1 O5 71.1(2) . . ? O8 Bi1 O5 126.6(2) 4_566 . ? O6 Bi1 O5 51.5(2) . . ? S1 O3 Bi1 136.2(4) . . ? S2 O5 Bi1 98.3(4) . . ? S2 O6 Bi1 105.6(4) . . ? S2 O7 Bi1 100.5(3) . 4_565 ? S2 O8 Bi1 98.9(3) . 4_565 ? S3 O9 Bi1 98.7(3) . . ? S3 O11 Bi1 100.4(4) . . ? Bi1 O12 H2 104(3) . . ? Bi1 O12 H3 113(7) . . ? H2 O12 H3 93(10) . . ? S3 O13 Bi1 141.8(4) . 1_455 ? O2 S1 O1 111.4(8) . . ? O2 S1 O4 111.2(8) . . ? O1 S1 O4 105.0(10) . . ? O2 S1 O3 109.8(5) . . ? O1 S1 O3 110.6(6) . . ? O4 S1 O3 108.7(6) . . ? O5 S2 O7 115.1(5) . . ? O5 S2 O8 112.9(4) . . ? O7 S2 O8 105.2(4) . . ? O5 S2 O6 104.3(5) . . ? O7 S2 O6 109.7(4) . . ? O8 S2 O6 109.7(4) . . ? O11 S3 O10 111.3(4) . . ? O11 S3 O13 110.5(4) . . ? O10 S3 O13 109.4(4) . . ? O11 S3 O9 105.5(4) . . ? O10 S3 O9 110.5(4) . . ? O13 S3 O9 109.5(4) . . ? C2 C1 N1 110.9(9) . . ? C2 C1 H1A 109.5 . . ? N1 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 108.0 . . ? C1 C2 N2 109.8(8) . . ? C1 C2 H2A 109.7 . . ? N2 C2 H2A 109.7 . . ? C1 C2 H2B 109.7 . . ? N2 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? N1 C3 C4 112.2(8) . . ? N1 C3 H3A 109.2 . . ? C4 C3 H3A 109.2 . . ? N1 C3 H3B 109.2 . . ? C4 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? N2 C4 C3 110.8(9) . . ? N2 C4 H4A 109.5 . . ? C3 C4 H4A 109.5 . . ? N2 C4 H4B 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 108.1 . . ? N1 C5 H5A 109.5 . . ? N1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C3 N1 C5 110.1(9) . . ? C3 N1 C1 111.6(8) . . ? C5 N1 C1 111.5(9) . . ? C3 N1 H1 104(6) . . ? C5 N1 H1 113(6) . . ? C1 N1 H1 106(6) . . ? C4 N2 C2 111.3(9) . . ? C4 N2 H2C 109.4 . . ? C2 N2 H2C 109.4 . . ? C4 N2 H2D 109.4 . . ? C2 N2 H2D 109.4 . . ? H2C N2 H2D 108.0 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2C O6 0.90 2.21 3.016(11) 149.7 4_465 N2 H2C O13 0.90 2.55 3.165(12) 126.1 4_565 N2 H2D O8 0.90 2.01 2.905(11) 170.3 . O12 H3 O4 0.79(3) 2.30(8) 2.855(13) 128(9) . O12 H3 O4 0.79(3) 2.60(7) 3.236(19) 138(9) 3_667 O12 H2 O10 0.90(3) 1.94(10) 2.806(10) 162(26) 1_655 N1 H1 O2 0.87(10) 1.92(10) 2.752(13) 160(8) 1_454 _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 2.058 _refine_diff_density_min -1.547 _refine_diff_density_rms 0.227 # Attachment 'III-deta.cif' data_bb _database_code_depnum_ccdc_archive 'CCDC 675235' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H18 Bi N3 O13 S3' _chemical_formula_weight 621.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P2(1)2(1)2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.4037(4) _cell_length_b 13.2705(8) _cell_length_c 17.8484(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1516.76(16) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description column _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.721 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1192 _exptl_absorpt_coefficient_mu 12.114 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.0803 _exptl_absorpt_correction_T_max 0.4441 _exptl_absorpt_process_details ? _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7896 _diffrn_reflns_av_R_equivalents 0.0459 _diffrn_reflns_av_sigmaI/netI 0.0524 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 25.49 _reflns_number_total 2794 _reflns_number_gt 2636 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0150P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.009(6) _refine_ls_number_reflns 2794 _refine_ls_number_parameters 238 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0320 _refine_ls_R_factor_gt 0.0250 _refine_ls_wR_factor_ref 0.0560 _refine_ls_wR_factor_gt 0.0544 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _refine_ls_shift/su_max 0.004 _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 0.00243(4) 0.712187(14) 0.896347(9) 0.01858(8) Uani 1 1 d . . . S1 S 0.4891(2) 0.72577(10) 0.90299(6) 0.0174(3) Uani 1 1 d . . . S2 S 0.0783(2) 0.70859(12) 0.72207(7) 0.0208(3) Uani 1 1 d . . . S3 S -0.0908(2) 0.47120(11) 0.98640(8) 0.0209(3) Uani 1 1 d . . . O1 O 0.6103(6) 0.7502(3) 0.97193(19) 0.0264(10) Uani 1 1 d . . . O2 O 0.3469(6) 0.8080(3) 0.8835(2) 0.0268(9) Uani 1 1 d . . . O3 O 0.3596(6) 0.6353(3) 0.9140(2) 0.0245(9) Uani 1 1 d . . . O4 O 0.0218(8) 0.8037(3) 0.7587(2) 0.0358(10) Uani 1 1 d . . . O5 O 0.0687(6) 0.6303(3) 0.78270(19) 0.0290(10) Uani 1 1 d . . . O6 O -0.0724(7) 0.6825(4) 0.6645(2) 0.0398(12) Uani 1 1 d . . . O7 O 0.2875(7) 0.7143(4) 0.6912(2) 0.0354(11) Uani 1 1 d . . . O8 O -0.2816(6) 0.4776(4) 1.0317(3) 0.0342(11) Uani 1 1 d . . . O9 O 0.0912(7) 0.4856(4) 1.0345(3) 0.0378(11) Uani 1 1 d . . . O10 O -0.0828(7) 0.3737(3) 0.9495(2) 0.0351(11) Uani 1 1 d . . . O11 O -0.0948(7) 0.5506(3) 0.9282(2) 0.0362(11) Uani 1 1 d . . . O12 O 0.6466(6) 0.7111(3) 0.8429(2) 0.0261(9) Uani 1 1 d . . . O13 O -0.0766(7) 0.8970(3) 0.9113(2) 0.0257(9) Uani 1 1 d D . . C1 C 0.4032(10) 0.3042(5) 0.9328(3) 0.0312(14) Uani 1 1 d . . . H1A H 0.2797 0.2639 0.9233 0.037 Uiso 1 1 calc R . . H1B H 0.5250 0.2627 0.9231 0.037 Uiso 1 1 calc R . . C2 C 0.4047(11) 0.3939(5) 0.8814(3) 0.0359(16) Uani 1 1 d . B . H2A H 0.2851 0.4366 0.8918 0.043 Uiso 1 1 calc R . . H2B H 0.5305 0.4332 0.8894 0.043 Uiso 1 1 calc R . . C3 C 0.3948(12) 0.4409(6) 0.7476(3) 0.0353(17) Uani 1 1 d . B . H3A H 0.2761 0.4840 0.7583 0.042 Uiso 1 1 calc R . . H3B H 0.3742 0.4127 0.6980 0.042 Uiso 1 1 calc R . . C4 C 0.5868(14) 0.5045(8) 0.7463(4) 0.055(2) Uani 1 1 d . . . H4A H 0.5822 0.5519 0.7876 0.065 Uiso 1 1 calc R A 1 H4B H 0.7084 0.4619 0.7530 0.065 Uiso 1 1 calc R A 1 N1 N 0.4045(8) 0.3374(4) 1.0123(3) 0.0303(12) Uani 1 1 d . . . H1C H 0.5191 0.3734 1.0211 0.045 Uiso 1 1 calc R . . H1D H 0.4029 0.2837 1.0421 0.045 Uiso 1 1 calc R . . H1E H 0.2922 0.3751 1.0212 0.045 Uiso 1 1 calc R . . N2 N 0.3965(8) 0.3580(4) 0.8022(3) 0.0344(13) Uani 1 1 d . . . H2C H 0.5079 0.3184 0.7934 0.041 Uiso 1 1 calc R B . H2D H 0.2809 0.3203 0.7959 0.041 Uiso 1 1 calc R . . N3 N 0.605(2) 0.5543(10) 0.6831(7) 0.034(4) Uani 0.416(12) 1 d P B 1 H3C H 0.7371 0.5726 0.6765 0.051 Uiso 0.416(12) 1 calc PR B 1 H3D H 0.5242 0.6089 0.6846 0.051 Uiso 0.416(12) 1 calc PR B 1 H3E H 0.5649 0.5151 0.6452 0.051 Uiso 0.416(12) 1 calc PR B 1 N4 N 0.7507(16) 0.4842(7) 0.6959(5) 0.039(3) Uani 0.584(12) 1 d P B 2 H4C H 0.7046 0.4906 0.6491 0.059 Uiso 0.584(12) 1 calc PR B 2 H4D H 0.7965 0.4216 0.7031 0.059 Uiso 0.584(12) 1 calc PR B 2 H4E H 0.8546 0.5275 0.7038 0.059 Uiso 0.584(12) 1 calc PR B 2 H1 H -0.043(11) 0.947(3) 0.942(3) 0.04(2) Uiso 1 1 d D . . H2 H -0.186(9) 0.893(8) 0.942(4) 0.10(4) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi1 0.01461(12) 0.01966(12) 0.02147(11) -0.00250(7) -0.00104(13) 0.00049(14) S1 0.0124(6) 0.0213(7) 0.0185(6) -0.0003(5) -0.0007(7) -0.0012(7) S2 0.0174(6) 0.0256(8) 0.0195(6) 0.0015(6) 0.0001(5) -0.0014(6) S3 0.0186(6) 0.0156(7) 0.0285(7) 0.0036(6) 0.0020(6) -0.0007(6) O1 0.017(2) 0.042(3) 0.0200(19) -0.0051(19) 0.0000(16) -0.0087(19) O2 0.021(2) 0.024(2) 0.036(2) 0.0069(19) 0.0026(17) 0.0051(19) O3 0.020(2) 0.023(2) 0.031(2) -0.0046(19) -0.0052(16) -0.0045(18) O4 0.034(3) 0.028(2) 0.046(2) -0.0033(18) 0.004(2) -0.002(3) O5 0.032(2) 0.031(2) 0.0235(18) 0.0074(19) 0.0020(16) 0.001(2) O6 0.041(3) 0.053(3) 0.026(2) 0.009(2) -0.0149(19) -0.013(2) O7 0.026(2) 0.041(3) 0.039(3) 0.000(2) 0.009(2) -0.006(2) O8 0.024(2) 0.035(3) 0.044(3) -0.004(2) 0.008(2) -0.006(2) O9 0.030(2) 0.039(3) 0.044(3) 0.001(2) -0.010(2) -0.002(2) O10 0.043(3) 0.015(2) 0.047(2) -0.0039(19) 0.005(2) 0.002(2) O11 0.043(3) 0.026(3) 0.039(2) 0.012(2) -0.004(2) -0.009(2) O12 0.021(2) 0.034(3) 0.024(2) -0.0008(18) 0.0036(16) 0.003(2) O13 0.024(2) 0.019(2) 0.035(2) -0.0037(19) 0.0058(18) 0.0005(18) C1 0.029(3) 0.025(4) 0.040(3) -0.005(3) 0.006(3) -0.002(3) C2 0.038(4) 0.035(4) 0.035(3) -0.004(3) 0.002(3) -0.005(3) C3 0.035(4) 0.034(4) 0.037(4) -0.009(3) 0.005(3) 0.003(4) C4 0.046(5) 0.083(7) 0.035(4) -0.010(4) 0.015(3) -0.030(5) N1 0.023(3) 0.031(3) 0.038(3) 0.002(2) -0.001(2) 0.001(2) N2 0.024(3) 0.032(3) 0.048(3) -0.013(3) -0.008(3) 0.004(3) N3 0.035(8) 0.028(8) 0.041(8) 0.020(6) -0.011(6) -0.005(7) N4 0.046(6) 0.027(6) 0.046(6) -0.007(5) 0.008(5) -0.013(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Bi1 O11 2.305(4) . ? Bi1 O5 2.340(4) . ? Bi1 O12 2.471(4) 1_455 ? Bi1 O1 2.501(4) 4_467 ? Bi1 O13 2.519(4) . ? Bi1 O3 2.524(4) . ? Bi1 O2 2.556(4) . ? Bi1 O4 2.743(4) . ? Bi1 S1 3.1239(14) . ? S1 O2 1.463(4) . ? S1 O3 1.472(4) . ? S1 O12 1.486(4) . ? S1 O1 1.490(4) . ? S2 O7 1.450(4) . ? S2 O6 1.452(4) . ? S2 O4 1.467(4) . ? S2 O5 1.501(4) . ? S3 O10 1.453(5) . ? S3 O9 1.460(5) . ? S3 O8 1.468(4) . ? S3 O11 1.479(4) . ? O1 Bi1 2.501(4) 4_567 ? O12 Bi1 2.471(4) 1_655 ? O13 H1 0.89(2) . ? O13 H2 0.89(2) . ? C1 N1 1.485(7) . ? C1 C2 1.503(9) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 N2 1.492(7) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N2 1.471(8) . ? C3 C4 1.491(10) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 N3 1.312(13) . ? C4 N4 1.408(12) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? N1 H1C 0.8900 . ? N1 H1D 0.8900 . ? N1 H1E 0.8900 . ? N2 H2C 0.9000 . ? N2 H2D 0.9000 . ? N3 H3C 0.8900 . ? N3 H3D 0.8900 . ? N3 H3E 0.8900 . ? N4 H4C 0.8900 . ? N4 H4D 0.8900 . ? N4 H4E 0.8900 . ? 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 O11 Bi1 O5 80.28(15) . . ? O11 Bi1 O12 80.84(16) . 1_455 ? O5 Bi1 O12 80.19(13) . 1_455 ? O11 Bi1 O1 91.62(15) . 4_467 ? O5 Bi1 O1 149.05(13) . 4_467 ? O12 Bi1 O1 128.26(12) 1_455 4_467 ? O11 Bi1 O13 145.66(16) . . ? O5 Bi1 O13 125.50(14) . . ? O12 Bi1 O13 82.04(14) 1_455 . ? O1 Bi1 O13 76.18(14) 4_467 . ? O11 Bi1 O3 80.67(15) . . ? O5 Bi1 O3 75.87(13) . . ? O12 Bi1 O3 151.82(13) 1_455 . ? O1 Bi1 O3 73.34(12) 4_467 . ? O13 Bi1 O3 124.23(14) . . ? O11 Bi1 O2 135.91(15) . . ? O5 Bi1 O2 89.80(14) . . ? O12 Bi1 O2 139.82(13) 1_455 . ? O1 Bi1 O2 75.33(13) 4_467 . ? O13 Bi1 O2 72.46(14) . . ? O3 Bi1 O2 55.28(13) . . ? O11 Bi1 O4 130.19(14) . . ? O5 Bi1 O4 54.62(13) . . ? O12 Bi1 O4 72.43(14) 1_455 . ? O1 Bi1 O4 137.82(14) 4_467 . ? O13 Bi1 O4 70.92(13) . . ? O3 Bi1 O4 104.46(14) . . ? O2 Bi1 O4 70.15(14) . . ? O11 Bi1 S1 108.29(12) . . ? O5 Bi1 S1 83.03(10) . . ? O12 Bi1 S1 159.25(9) 1_455 . ? O1 Bi1 S1 71.17(9) 4_467 . ? O13 Bi1 S1 98.06(10) . . ? O3 Bi1 S1 27.70(10) . . ? O2 Bi1 S1 27.61(9) . . ? O4 Bi1 S1 87.90(11) . . ? O2 S1 O3 106.8(2) . . ? O2 S1 O12 110.4(2) . . ? O3 S1 O12 111.8(2) . . ? O2 S1 O1 111.0(2) . . ? O3 S1 O1 111.1(2) . . ? O12 S1 O1 105.8(2) . . ? O2 S1 Bi1 54.06(17) . . ? O3 S1 Bi1 52.85(16) . . ? O12 S1 Bi1 129.95(16) . . ? O1 S1 Bi1 124.29(16) . . ? O7 S2 O6 111.0(3) . . ? O7 S2 O4 110.7(3) . . ? O6 S2 O4 110.9(3) . . ? O7 S2 O5 110.4(3) . . ? O6 S2 O5 108.5(2) . . ? O4 S2 O5 105.3(2) . . ? O10 S3 O9 110.8(3) . . ? O10 S3 O8 109.3(3) . . ? O9 S3 O8 109.4(3) . . ? O10 S3 O11 108.5(3) . . ? O9 S3 O11 109.5(3) . . ? O8 S3 O11 109.4(3) . . ? S1 O1 Bi1 132.5(2) . 4_567 ? S1 O2 Bi1 98.3(2) . . ? S1 O3 Bi1 99.4(2) . . ? S2 O4 Bi1 91.7(2) . . ? S2 O5 Bi1 108.1(2) . . ? S3 O11 Bi1 146.2(3) . . ? S1 O12 Bi1 110.2(2) . 1_655 ? Bi1 O13 H1 139(4) . . ? Bi1 O13 H2 99(7) . . ? H1 O13 H2 82(7) . . ? N1 C1 C2 110.4(5) . . ? N1 C1 H1A 109.6 . . ? C2 C1 H1A 109.6 . . ? N1 C1 H1B 109.6 . . ? C2 C1 H1B 109.6 . . ? H1A C1 H1B 108.1 . . ? N2 C2 C1 109.0(5) . . ? N2 C2 H2A 109.9 . . ? C1 C2 H2A 109.9 . . ? N2 C2 H2B 109.9 . . ? C1 C2 H2B 109.9 . . ? H2A C2 H2B 108.3 . . ? N2 C3 C4 115.4(6) . . ? N2 C3 H3A 108.4 . . ? C4 C3 H3A 108.4 . . ? N2 C3 H3B 108.4 . . ? C4 C3 H3B 108.4 . . ? H3A C3 H3B 107.5 . . ? N3 C4 N4 58.8(8) . . ? N3 C4 C3 111.8(8) . . ? N4 C4 C3 121.1(7) . . ? N3 C4 H4A 109.3 . . ? N4 C4 H4A 129.2 . . ? C3 C4 H4A 109.3 . . ? N3 C4 H4B 109.3 . . ? N4 C4 H4B 50.9 . . ? C3 C4 H4B 109.3 . . ? H4A C4 H4B 107.9 . . ? C1 N1 H1C 109.5 . . ? C1 N1 H1D 109.5 . . ? H1C N1 H1D 109.5 . . ? C1 N1 H1E 109.5 . . ? H1C N1 H1E 109.5 . . ? H1D N1 H1E 109.5 . . ? C3 N2 C2 112.9(5) . . ? C3 N2 H2C 109.0 . . ? C2 N2 H2C 109.0 . . ? C3 N2 H2D 109.0 . . ? C2 N2 H2D 109.0 . . ? H2C N2 H2D 107.8 . . ? C4 N3 H3C 109.5 . . ? C4 N3 H3D 109.5 . . ? C4 N3 H3E 109.5 . . ? C4 N4 H4C 109.5 . . ? C4 N4 H4D 109.5 . . ? H4C N4 H4D 109.5 . . ? C4 N4 H4E 109.5 . . ? H4C N4 H4E 109.5 . . ? H4D N4 H4E 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O13 H2 O3 0.89(2) 2.62(8) 3.174(5) 122(7) 4_467 O13 H2 O1 0.89(2) 2.36(9) 2.998(6) 129(9) 1_455 O13 H2 O9 0.89(2) 2.20(9) 2.809(6) 125(9) 4_467 O13 H1 O8 0.89(2) 2.00(5) 2.715(6) 136(6) 4_567 N4 H4E O5 0.89 2.39 3.210(10) 152.7 1_655 N4 H4E O6 0.89 2.22 2.919(10) 134.8 1_655 N4 H4D O2 0.89 2.35 2.805(10) 112.1 3_646 N4 H4D O4 0.89 2.07 2.918(12) 160.0 3_646 N4 H4C O8 0.89 2.19 2.980(11) 147.2 2_564 N3 H3E O8 0.89 2.46 2.959(14) 116.1 2_564 N3 H3E O9 0.89 2.21 2.981(14) 144.0 2_564 N3 H3D O7 0.89 2.07 2.942(15) 168.0 . N3 H3C O6 0.89 1.91 2.698(14) 146.2 1_655 N2 H2D O6 0.90 2.37 3.176(7) 148.5 3_546 N2 H2D O4 0.90 2.18 2.979(8) 147.5 3_546 N2 H2C O7 0.90 1.92 2.783(7) 159.0 3_646 N1 H1E O9 0.89 1.97 2.837(7) 165.8 . N1 H1D O6 0.89 2.48 2.935(6) 112.1 2_565 N1 H1D O10 0.89 2.10 2.884(7) 147.2 4_557 N1 H1C O8 0.89 1.89 2.761(7) 165.2 1_655 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.102 _refine_diff_density_min -1.126 _refine_diff_density_rms 0.178 # Attachment 'IV-TETA-revised.cif' data_cc _database_code_depnum_ccdc_archive 'CCDC 675236' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H34 Bi2 N4 O26 S5' _chemical_formula_weight 1156.63 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.732(2) _cell_length_b 10.0011(8) _cell_length_c 14.4245(12) _cell_angle_alpha 90.00 _cell_angle_beta 97.434(2) _cell_angle_gamma 90.00 _cell_volume 2822.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.722 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2208 _exptl_absorpt_coefficient_mu 12.935 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.1125 _exptl_absorpt_correction_T_max 0.5108 _exptl_absorpt_process_details ? _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6833 _diffrn_reflns_av_R_equivalents 0.0427 _diffrn_reflns_av_sigmaI/netI 0.0457 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2612 _reflns_number_gt 1946 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0361P)^2^+5.4412P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2612 _refine_ls_number_parameters 220 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0438 _refine_ls_R_factor_gt 0.0276 _refine_ls_wR_factor_ref 0.0770 _refine_ls_wR_factor_gt 0.0658 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.201 _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 0.008008(12) 0.25006(3) 0.037421(16) 0.01967(13) Uani 1 1 d D . . S1 S 0.11054(9) -0.0404(2) 0.03180(12) 0.0219(4) Uani 1 1 d . . . S2 S 0.0000 0.2519(3) 0.2500 0.0237(6) Uani 1 2 d SD . . S3 S 0.11244(9) 0.5266(2) 0.08905(12) 0.0244(4) Uani 1 1 d . . . O1 O 0.1774(3) -0.0684(7) 0.0808(5) 0.0519(18) Uani 1 1 d . . . O2 O 0.1030(2) 0.1074(5) 0.0212(3) 0.0269(12) Uani 1 1 d . . . O3 O 0.0443(2) 0.1658(5) 0.1991(3) 0.0297(12) Uani 1 1 d . . . O4 O -0.0398(3) 0.3355(6) 0.1788(3) 0.0321(13) Uani 1 1 d . . . O5 O 0.1051(3) 0.3772(5) 0.0856(4) 0.0364(14) Uani 1 1 d . . . O6 O 0.1827(4) 0.5556(10) 0.0866(8) 0.106(3) Uani 1 1 d . . . O7 O 0.0895(3) 0.5796(6) 0.1725(4) 0.0497(17) Uani 1 1 d . . . O8 O 0.0696(4) 0.5769(7) 0.0083(4) 0.075(3) Uani 1 1 d . . . O9 O -0.1016(3) 0.1012(5) 0.0621(4) 0.0377(14) Uani 1 1 d . . . O10 O -0.0555(3) 0.0922(5) -0.0804(3) 0.0305(13) Uani 1 1 d . . . O11 O 0.0404(3) 0.3119(7) -0.1132(3) 0.0319(13) Uani 1 1 d D . . O12 O 0.8374(3) 0.5093(7) 0.1513(4) 0.0405(14) Uani 1 1 d D . . O13 O 0.0887(3) 0.1130(7) 0.7884(4) 0.0450(16) Uani 1 1 d D . . N1 N 0.2105(4) 0.2436(6) 0.3725(5) 0.0344(18) Uani 1 1 d . . . H1A H 0.2450 0.2011 0.4061 0.052 Uiso 1 1 calc R . . H1B H 0.1723 0.2297 0.3976 0.052 Uiso 1 1 calc R . . H1C H 0.2194 0.3308 0.3721 0.052 Uiso 1 1 calc R . . N2 N 0.2291(3) 0.2108(7) 0.1192(4) 0.0270(15) Uani 1 1 d . . . H2A H 0.2398 0.1233 0.1192 0.032 Uiso 1 1 calc R . . H2B H 0.1837 0.2175 0.1027 0.032 Uiso 1 1 calc R . . C1 C 0.2022(4) 0.1931(9) 0.2774(5) 0.0328(19) Uani 1 1 d . . . H1D H 0.1547 0.2026 0.2509 0.039 Uiso 1 1 calc R . . H1E H 0.2131 0.0984 0.2788 0.039 Uiso 1 1 calc R . . C2 C 0.2455(4) 0.2616(7) 0.2157(5) 0.027(2) Uani 1 1 d . . . H2C H 0.2933 0.2455 0.2379 0.032 Uiso 1 1 calc R . . H2D H 0.2374 0.3572 0.2168 0.032 Uiso 1 1 calc R . . C3 C 0.2631(4) 0.2769(8) 0.0476(5) 0.0273(18) Uani 1 1 d . . . H3A H 0.3120 0.2623 0.0603 0.033 Uiso 1 1 calc R . . H3B H 0.2547 0.3724 0.0492 0.033 Uiso 1 1 calc R . . H1 H 0.021(9) 0.385(8) -0.140(7) 0.26(10) Uiso 1 1 d D . . H2 H 0.044(5) 0.244(5) -0.152(5) 0.03(3) Uiso 1 1 d D . . H3 H 0.087(4) 0.098(8) 0.7265(19) 0.05(3) Uiso 1 1 d D . . H4 H 0.067(6) 0.046(9) 0.816(5) 0.13(5) Uiso 1 1 d D . . H5 H 0.848(8) 0.595(6) 0.142(10) 0.21(8) Uiso 1 1 d D . . H6 H 0.858(6) 0.477(11) 0.206(5) 0.12(5) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi1 0.01708(18) 0.0223(2) 0.01951(18) -0.00072(11) 0.00187(12) 0.00132(12) S1 0.0176(9) 0.0185(10) 0.0297(10) -0.0012(8) 0.0032(7) 0.0016(8) S2 0.0219(14) 0.0310(17) 0.0184(12) 0.000 0.0031(10) 0.000 S3 0.0222(10) 0.0198(10) 0.0301(10) -0.0008(8) -0.0007(7) -0.0004(8) O1 0.022(3) 0.055(5) 0.074(4) 0.008(3) -0.012(3) 0.000(3) O2 0.025(3) 0.019(3) 0.038(3) 0.000(2) 0.008(2) -0.001(2) O3 0.033(3) 0.026(3) 0.031(3) 0.003(2) 0.007(2) 0.009(2) O4 0.037(3) 0.035(4) 0.024(3) 0.001(2) -0.001(2) 0.015(3) O5 0.035(3) 0.016(3) 0.055(4) 0.003(3) -0.004(3) -0.001(2) O6 0.036(5) 0.080(7) 0.210(10) -0.045(6) 0.049(5) -0.025(4) O7 0.073(5) 0.044(4) 0.031(3) 0.000(3) 0.001(3) 0.030(3) O8 0.130(7) 0.058(5) 0.030(3) -0.005(3) -0.011(4) 0.062(5) O9 0.050(4) 0.030(3) 0.037(3) -0.014(3) 0.021(3) -0.003(3) O10 0.032(3) 0.031(3) 0.030(3) -0.008(2) 0.011(2) -0.011(2) O11 0.033(3) 0.032(4) 0.032(3) 0.002(3) 0.010(2) 0.005(3) O12 0.038(3) 0.044(4) 0.038(3) 0.005(3) -0.001(3) 0.003(3) O13 0.059(4) 0.041(4) 0.036(4) -0.003(3) 0.011(3) 0.002(3) N1 0.036(4) 0.043(5) 0.025(3) 0.002(3) 0.010(3) -0.012(3) N2 0.029(4) 0.025(4) 0.026(3) 0.001(3) 0.000(3) -0.005(3) C1 0.036(5) 0.037(5) 0.026(4) -0.003(4) 0.006(3) -0.013(4) C2 0.026(5) 0.030(6) 0.025(4) -0.003(3) 0.003(4) -0.006(3) C3 0.032(5) 0.025(5) 0.025(4) 0.006(3) 0.004(3) -0.002(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Bi1 O5 2.330(5) . ? Bi1 O8 2.347(6) 5_565 ? Bi1 O2 2.391(5) . ? Bi1 O11 2.423(5) . ? Bi1 O3 2.496(5) . ? Bi1 O4 2.505(5) . ? Bi1 O10 2.530(5) . ? Bi1 O9 2.687(5) . ? S1 O1 1.442(6) . ? S1 O10 1.460(5) 5 ? S1 O9 1.474(5) 5 ? S1 O2 1.492(5) . ? S2 O4 1.471(5) 2 ? S2 O4 1.471(5) . ? S2 O3 1.486(5) 2 ? S2 O3 1.486(5) . ? S2 Bi1 3.0908(4) 2 ? S3 O6 1.421(7) . ? S3 O8 1.439(6) . ? S3 O7 1.441(6) . ? S3 O5 1.501(5) . ? O8 Bi1 2.347(6) 5_565 ? O9 S1 1.474(5) 5 ? O10 S1 1.460(5) 5 ? N1 C1 1.452(9) . ? N2 C3 1.459(10) . ? N2 C2 1.478(8) . ? C1 C2 1.478(10) . ? C3 C3 1.503(15) 7 ? 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 O5 Bi1 O8 99.4(2) . 5_565 ? O5 Bi1 O2 74.33(19) . . ? O8 Bi1 O2 154.6(2) 5_565 . ? O5 Bi1 O11 80.00(19) . . ? O8 Bi1 O11 78.3(2) 5_565 . ? O2 Bi1 O11 76.31(18) . . ? O5 Bi1 O3 77.31(18) . . ? O8 Bi1 O3 127.51(19) 5_565 . ? O2 Bi1 O3 75.92(16) . . ? O11 Bi1 O3 147.92(17) . . ? O5 Bi1 O4 87.31(19) . . ? O8 Bi1 O4 71.13(19) 5_565 . ? O2 Bi1 O4 131.75(16) . . ? O11 Bi1 O4 144.5(2) . . ? O3 Bi1 O4 56.43(15) . . ? O5 Bi1 O10 149.11(18) . . ? O8 Bi1 O10 91.3(2) 5_565 . ? O2 Bi1 O10 83.60(16) . . ? O11 Bi1 O10 73.87(18) . . ? O3 Bi1 O10 118.29(17) . . ? O4 Bi1 O10 123.58(16) . . ? O5 Bi1 O9 155.23(18) . . ? O8 Bi1 O9 86.5(3) 5_565 . ? O2 Bi1 O9 109.69(17) . . ? O11 Bi1 O9 124.76(17) . . ? O3 Bi1 O9 80.06(17) . . ? O4 Bi1 O9 71.74(16) . . ? O10 Bi1 O9 53.53(15) . . ? O1 S1 O10 112.7(4) . 5 ? O1 S1 O9 111.3(4) . 5 ? O10 S1 O9 106.7(3) 5 5 ? O1 S1 O2 108.4(4) . . ? O10 S1 O2 109.3(3) 5 . ? O9 S1 O2 108.4(3) 5 . ? O4 S2 O4 110.8(5) 2 . ? O4 S2 O3 106.2(3) 2 2 ? O4 S2 O3 112.3(3) . 2 ? O4 S2 O3 112.3(3) 2 . ? O4 S2 O3 106.2(3) . . ? O3 S2 O3 109.2(5) 2 . ? O4 S2 Bi1 53.24(19) 2 2 ? O4 S2 Bi1 127.3(2) . 2 ? O3 S2 Bi1 52.98(18) 2 2 ? O3 S2 Bi1 126.5(2) . 2 ? O6 S3 O8 112.4(6) . . ? O6 S3 O7 111.0(5) . . ? O8 S3 O7 109.4(4) . . ? O6 S3 O5 107.0(4) . . ? O8 S3 O5 106.1(4) . . ? O7 S3 O5 110.8(4) . . ? S1 O2 Bi1 130.6(3) . . ? S2 O3 Bi1 98.6(2) . . ? S2 O4 Bi1 98.7(2) . . ? S3 O5 Bi1 128.7(3) . . ? S3 O8 Bi1 141.1(4) . 5_565 ? S1 O9 Bi1 96.3(2) 5 . ? S1 O10 Bi1 103.5(2) 5 . ? C3 N2 C2 116.5(6) . . ? N1 C1 C2 113.8(7) . . ? C1 C2 N2 109.6(6) . . ? N2 C3 C3 110.5(8) . 7 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O12 H6 O4 0.89(2) 2.54(12) 2.967(8) 110(9) 1_655 O12 H6 O7 0.89(2) 2.18(9) 2.842(8) 131(9) 2_655 O12 H5 O11 0.90(2) 2.47(14) 3.108(9) 128(13) 5_665 O13 H4 O9 0.91(2) 2.33(9) 3.026(9) 133(10) 5_556 N2 H2B O5 0.90 2.22 2.947(8) 137.9 . N2 H2B O2 0.90 2.16 2.890(8) 138.3 . N2 H2A O1 0.90 2.31 3.000(9) 133.7 . N2 H2A O12 0.90 2.23 2.929(9) 133.7 3_445 N1 H1C O1 0.89 2.29 2.914(9) 126.7 4 N1 H1C O12 0.89 2.11 2.827(9) 136.8 2_655 N1 H1B O9 0.89 2.04 2.840(8) 149.7 2 N1 H1A O6 0.89 2.03 2.828(10) 148.5 4_545 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.917 _refine_diff_density_min -1.376 _refine_diff_density_rms 0.233