Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Nicolas Mercier' _publ_contact_author_address ; Chemistry University of Angers 2 Boulevard Lavoisier Angers 49045 FRANCE ; _publ_contact_author_email NICOLAS.MERCIER@UNIV-ANGERS.FR _publ_section_title ; Type Structure, Which Is Composed of Organic Diammonium, Triiodide and Hexaiodobismuthate, Varies According to different structures of incorporated Cations ; loop_ _publ_author_name N.Mercier 'Wenhua Bi.' N.Louvain J.Luc B.Sahraoui # Attachment 'revised_SSBiI6I3(1).cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2006-07-13 at 23:20:58 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\program files\wingx\files\cifdoc.dat # CIF files read : nanny absorb struct data_3 _database_code_depnum_ccdc_archive 'CCDC 620818' _audit_creation_date 2006-07-13T23:20:58-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_formula_moiety '2(C4 H14 N2 S2),(Bi I6), I3' _chemical_formula_sum 'C8 H28 Bi I9 N4 S4' _chemical_formula_weight 1659.66 #------------------ UNIT CELL INFORMATION -----------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/m 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 11.954(2) _cell_length_b 12.521(2) _cell_length_c 11.888(2) _cell_angle_alpha 90 _cell_angle_beta 95.680(10) _cell_angle_gamma 90 _cell_volume 1770.5(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 #------------------ CRYSTAL INFORMATION -------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour brown _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_diffrn 3.113 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1456 _exptl_absorpt_coefficient_mu 13.068 _exptl_absorpt_correction_type gaussian _exptl_absorpt_correction_T_min 0.2889 _exptl_absorpt_correction_T_max 0.5915 #------------------ DATA COLLECTION INFORMATION -----------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device_type area_detector _diffrn_measurement_method CCD _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_detector_area_resol_mean 9 _diffrn_reflns_number 25214 _diffrn_reflns_av_R_equivalents 0.0769 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.68 _diffrn_reflns_theta_max 27.51 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measured_fraction_theta_full 0.991 _reflns_number_total 2122 _reflns_number_gt 1654 _reflns_threshold_expression >2sigma(I) #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #------------------ REFINEMENT INFORMATION ----------------------------------# _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^)+(0.0565P)^2^+7.0786P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 2122 _refine_ls_number_parameters 67 _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.1085 _refine_ls_goodness_of_fit_ref 1.125 _refine_ls_restrained_S_all 1.125 _refine_ls_shift/su_max 0 _refine_diff_density_max 1.848 _refine_diff_density_min -1.111 #------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------# 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 0 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_group _atom_site_disorder_assembly Bi Bi 0.5 0.5 0 0.04138(19) Uani 1 d S . . I5 I 0.5 0.74667(5) 0 0.0549(2) Uani 1 d S . . I4 I 0.25157(6) 0.5 0.04531(8) 0.0585(2) Uani 1 d S . . I1 I 0 0.5 -0.5 0.0704(4) Uani 1 d S . . I3 I 0.42576(8) 0.5 -0.25515(7) 0.0711(3) Uani 1 d S . . I2 I 0.02108(9) 0.5 -0.25223(10) 0.0807(3) Uani 1 d S . . S1 S 0.2930(6) 0.3581(5) -0.5072(5) 0.0883(18) Uani 0.5 d P 2 A C1 C 0.3323(13) 0.2664(13) -0.6942(13) 0.116(5) Uiso 1 d . . A H1A H 0.3626 0.208 -0.6471 0.139 Uiso 1 calc R . . H1B H 0.394 0.3124 -0.7104 0.139 Uiso 1 calc R . . C2 C 0.2545(13) 0.3245(16) -0.6375(13) 0.131(6) Uiso 1 d . . . H2A H 0.2229 0.3786 -0.6898 0.157 Uiso 0.5 calc PR 1 A H2B H 0.2971 0.362 -0.576 0.157 Uiso 0.5 calc PR 1 A H2C H 0.1868 0.2816 -0.6377 0.157 Uiso 0.5 d PR 2 A H2D H 0.2344 0.3892 -0.6796 0.157 Uiso 0.5 d PR 2 A N1 N 0.2695(7) 0.2203(8) -0.8106(7) 0.078(2) Uani 1 d . . . H1C H 0.3181 0.1831 -0.847 0.116 Uiso 1 calc R . A H1D H 0.2426 0.2743 -0.8538 0.116 Uiso 1 calc R . . H1E H 0.2131 0.178 -0.7952 0.116 Uiso 1 calc R . . S2 S 0.1441(6) 0.2646(6) -0.5818(6) 0.100(2) Uani 0.5 d P 1 A 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 Bi 0.0386(3) 0.0382(3) 0.0475(3) 0 0.0050(2) 0 I5 0.0545(4) 0.0327(4) 0.0785(6) 0 0.0123(4) 0 I4 0.0368(4) 0.0605(5) 0.0798(6) 0 0.0144(4) 0 I1 0.0432(6) 0.0596(7) 0.1084(10) 0 0.0076(6) 0 I3 0.0778(6) 0.0831(6) 0.0522(5) 0 0.0061(4) 0 I2 0.0751(6) 0.0709(6) 0.0948(7) 0 0.0026(5) 0 S1 0.127(5) 0.072(3) 0.064(3) -0.007(3) -0.001(3) 0.011(3) N1 0.072(5) 0.082(6) 0.080(6) -0.011(5) 0.012(4) -0.010(4) S2 0.103(5) 0.096(5) 0.102(5) 0.005(4) 0.015(4) 0.030(4) #------------------ MOLECULAR GEOMETRY --------------------------------------# _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 Bi I4 3.0701(9) . ? Bi I4 3.0701(9) 5_665 ? Bi I3 3.0749(10) . ? Bi I3 3.0749(10) 5_665 ? Bi I5 3.0885(8) 5_665 ? Bi I5 3.0885(8) . ? I1 I2 2.9313(13) 5_564 ? I1 I2 2.9313(13) . ? S1 C2 1.627(16) . ? C1 C2 1.404(19) . ? C1 N1 1.615(16) . ? C2 S2 1.707(18) . ? 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 I4 Bi I4 180 . 5_665 ? I4 Bi I3 89.04(3) . . ? I4 Bi I3 90.96(3) 5_665 . ? I4 Bi I3 90.96(3) . 5_665 ? I4 Bi I3 89.04(3) 5_665 5_665 ? I3 Bi I3 180 . 5_665 ? I4 Bi I5 90 . 5_665 ? I4 Bi I5 90 5_665 5_665 ? I3 Bi I5 90 . 5_665 ? I3 Bi I5 90 5_665 5_665 ? I4 Bi I5 90 . . ? I4 Bi I5 90 5_665 . ? I3 Bi I5 90 . . ? I3 Bi I5 90 5_665 . ? I5 Bi I5 180 5_665 . ? I2 I1 I2 180 5_564 . ? C2 C1 N1 108.8(12) . . ? C1 C2 S1 116.9(13) . . ? C1 C2 S2 122.2(15) . . ? S1 C2 S2 84.3(8) . . ? #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_sad _database_code_depnum_ccdc_archive 'CCDC 620819' _audit_creation_date 2006-07-13T18:05:16-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_formula_moiety '2(C4 H14 N2 S2), (Bi I6), (I3), 0.5H2O' _chemical_formula_sum 'C8 H29 Bi I9 N4 O0.50 S4' _chemical_formula_weight 1668.66 _chemical_absolute_configuration ad #------------------ UNIT CELL INFORMATION -----------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 23.450(5) _cell_length_b 12.724(3) _cell_length_c 12.401(3) _cell_angle_alpha 90 _cell_angle_beta 108.45(3) _cell_angle_gamma 90 _cell_volume 3510.0(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 #------------------ CRYSTAL INFORMATION -------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour brown _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 3.156 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2928 _exptl_absorpt_coefficient_mu 13.185 _exptl_absorpt_correction_type none #------------------ DATA COLLECTION INFORMATION -----------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device_type area_detector _diffrn_measurement_method CCD _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_detector_area_resol_mean 9 _diffrn_reflns_number 35506 _diffrn_reflns_av_R_equivalents 0.0668 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 30.01 _diffrn_reflns_theta_full 30.01 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measured_fraction_theta_full 0.993 _reflns_number_total 9998 _reflns_number_gt 6394 _reflns_threshold_expression >2sigma(I) #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #------------------ REFINEMENT INFORMATION ----------------------------------# _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^)+(0.0441P)^2^+21.9408P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr. _refine_ls_extinction_method none _refine_ls_number_reflns 9998 _refine_ls_number_parameters 246 _refine_ls_number_restraints 1 _refine_ls_R_factor_gt 0.0485 _refine_ls_wR_factor_ref 0.1198 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _refine_ls_shift/su_max 0.001 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.279(8) _refine_diff_density_max 2.947 _refine_diff_density_min -1.663 _refine_special_details ; The structure was first solved in the centric C2/m space group. But we could not locate the molecules and some heavy atoms were disordered over two positions, the reliability factor being around 9. By working in the C2 space group, we rapidly found a good solution, the reliability factor dropping to low values. We then tried to check if there was a mirror plane (and so a symmetry center). By looking accurately at the structure, we saw that the iodine atoms belonging to I3 entities and some iodides belonging to BiI6 polyhedra were not located on a mirror, and that the mirror would imply some disordered iodine atoms. Moreover, it would also imply a disorder of the water molecule and the organic molecules over two positions. On the contrary, by working in the C2 space group, we do not see any disorder. The acentric nature of compound 2 was unmbiguously proved by chi(2) measurements. ; #------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------# 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 0 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_group _atom_site_disorder_assembly Bi Bi 0.741575(16) 0.18097(5) 0.23492(3) 0.02915(10) Uani 1 d . . . I7 I 0.5 0.19117(12) 0.5 0.0341(2) Uani 1 d S . . I6 I 0.74668(5) 0.42431(7) 0.23306(10) 0.0377(3) Uani 1 d . . . I4 I 0.87540(3) 0.17561(10) 0.25581(7) 0.0420(2) Uani 1 d . . . I5 I 0.74631(5) -0.06034(7) 0.24171(11) 0.0417(3) Uani 1 d . . . I1 I 0.77672(3) 0.18658(11) 0.50025(6) 0.0442(2) Uani 1 d . . . I9 I 1 0.19117(12) 0 0.0378(3) Uani 1 d S . . I2 I 0.71505(3) 0.18058(11) -0.02183(6) 0.04125(18) Uani 1 d . . . I8 I 0.62620(4) 0.19301(10) 0.64224(7) 0.0470(2) Uani 1 d . . . I10 I 0.87105(4) 0.18872(11) -0.12108(7) 0.0480(2) Uani 1 d . . . I3 I 0.60621(4) 0.16966(10) 0.20649(9) 0.0516(3) Uani 1 d . . . S2 S 0.9880(2) 0.3251(3) -0.3000(4) 0.0489(11) Uani 1 d . . . S3 S 1.0240(2) 0.0210(3) 0.2600(4) 0.0461(11) Uani 1 d . . . S1 S 1.0416(2) 0.4509(4) -0.3022(5) 0.0520(13) Uani 1 d . . . S4 S 0.9675(2) -0.0952(4) 0.2728(4) 0.0494(12) Uani 1 d . . . C8 C 0.9118(8) -0.0879(13) 0.0385(13) 0.041(4) Uani 1 d . . . H8A H 0.9012 -0.128 -0.0316 0.049 Uiso 1 calc R . . H8B H 0.9371 -0.0298 0.0314 0.049 Uiso 1 calc R . . N4 N 0.8540(7) -0.0449(12) 0.0576(13) 0.050(4) Uani 1 d . . . H4A H 0.8639 -0.0064 0.1208 0.074 Uiso 1 calc R . . H4B H 0.8309 -0.0983 0.0644 0.074 Uiso 1 calc R . . H4C H 0.8341 -0.0051 -0.0013 0.074 Uiso 1 calc R . . C7 C 0.9455(7) -0.1565(12) 0.1354(14) 0.041(4) Uani 1 d . . . H7A H 0.9814 -0.182 0.121 0.049 Uiso 1 calc R . . H7B H 0.9207 -0.2171 0.1374 0.049 Uiso 1 calc R . . C3 C 0.9158(7) 0.3812(11) -0.3311(16) 0.047(4) Uani 1 d . . . H3A H 0.8877 0.3274 -0.325 0.056 Uiso 1 calc R . . H3B H 0.9167 0.4352 -0.2754 0.056 Uiso 1 calc R . . C4 C 0.8939(7) 0.4292(14) -0.4500(13) 0.044(4) Uani 1 d . . . H4D H 0.9223 0.4818 -0.4575 0.052 Uiso 1 calc R . . H4E H 0.891 0.3751 -0.5065 0.052 Uiso 1 calc R . . C5 C 1.1155(8) -0.0926(16) 0.4168(15) 0.056(5) Uani 1 d . . . H5A H 1.156 -0.1198 0.4333 0.067 Uiso 1 calc R . . H5B H 1.0888 -0.152 0.411 0.067 Uiso 1 calc R . . N2 N 0.8332(5) 0.4790(10) -0.4693(11) 0.053(3) Uani 1 d . . . H2A H 0.8055 0.429 -0.479 0.079 Uiso 1 calc R . . H2B H 0.8242 0.5194 -0.531 0.079 Uiso 1 calc R . . H2C H 0.834 0.518 -0.4093 0.079 Uiso 1 calc R . . N3 N 1.1129(5) -0.0246(12) 0.5129(10) 0.058(4) Uani 1 d . . . H3C H 1.1339 0.0339 0.5137 0.087 Uiso 1 calc R . . H3D H 1.1285 -0.0589 0.5781 0.087 Uiso 1 calc R . . H3E H 1.0748 -0.0081 0.5041 0.087 Uiso 1 calc R . . N1 N 1.1461(6) 0.4085(12) -0.0690(13) 0.057(5) Uani 1 d . . . H1A H 1.1434 0.3937 -0.1406 0.086 Uiso 1 calc R . . H1B H 1.1578 0.3514 -0.0263 0.086 Uiso 1 calc R . . H1C H 1.1728 0.4596 -0.0432 0.086 Uiso 1 calc R . . C1 C 1.0888(8) 0.4417(15) -0.0642(16) 0.055(5) Uani 1 d . . . H1D H 1.0942 0.4834 0.0037 0.066 Uiso 1 calc R . . H1E H 1.0649 0.3805 -0.0599 0.066 Uiso 1 calc R . . C2 C 1.0548(8) 0.5085(13) -0.1719(16) 0.050(5) Uani 1 d . . . H2D H 1.0777 0.5722 -0.1705 0.06 Uiso 1 calc R . . H2E H 1.0163 0.5293 -0.1648 0.06 Uiso 1 calc R . . C6 C 1.0990(6) -0.0387(12) 0.3092(15) 0.044(4) Uani 1 d . . . H6A H 1.102 -0.0882 0.2518 0.053 Uiso 1 calc R . . H6B H 1.1284 0.0162 0.3139 0.053 Uiso 1 calc R . . O O 1 0.0922(12) 0.5 0.062(4) Uani 1 d S . . 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 Bi 0.02642(18) 0.0281(2) 0.0311(2) -0.0003(3) 0.00645(15) -0.0016(3) I7 0.0451(5) 0.0256(6) 0.0289(5) 0 0.0080(4) 0 I6 0.0416(7) 0.0271(5) 0.0397(7) 0.0002(5) 0.0062(6) 0.0005(5) I4 0.0256(3) 0.0433(5) 0.0539(5) 0.0028(6) 0.0078(3) -0.0025(6) I5 0.0444(8) 0.0248(5) 0.0517(8) -0.0009(5) 0.0094(6) -0.0016(5) I1 0.0503(4) 0.0507(5) 0.0310(4) -0.0045(7) 0.0120(3) -0.0097(7) I9 0.0566(6) 0.0262(6) 0.0333(5) 0 0.0183(5) 0 I2 0.0454(4) 0.0487(5) 0.0265(4) -0.0012(6) 0.0069(3) -0.0016(7) I8 0.0404(4) 0.0495(6) 0.0440(5) 0.0043(6) 0.0035(3) -0.0010(6) I10 0.0506(4) 0.0429(5) 0.0484(5) -0.0010(7) 0.0125(4) 0.0047(6) I3 0.0313(4) 0.0442(6) 0.0814(7) 0.0015(6) 0.0210(4) -0.0001(5) S2 0.044(2) 0.037(2) 0.056(3) 0.0067(17) 0.003(2) 0.0000(16) S3 0.058(3) 0.037(2) 0.034(2) 0.0077(16) 0.0018(19) -0.0014(17) S1 0.048(3) 0.049(2) 0.057(3) 0.021(2) 0.013(2) -0.0025(19) S4 0.040(2) 0.056(3) 0.045(3) 0.020(2) 0.003(2) -0.0035(19) C8 0.059(11) 0.044(9) 0.022(7) -0.007(6) 0.016(7) -0.014(8) N4 0.054(11) 0.061(9) 0.037(9) -0.003(7) 0.019(8) -0.016(8) C7 0.028(8) 0.041(8) 0.053(11) -0.013(7) 0.011(7) -0.010(6) C3 0.031(8) 0.030(8) 0.081(13) 0.014(8) 0.021(8) 0.007(6) C4 0.026(7) 0.066(11) 0.025(8) 0.010(7) -0.014(7) 0.002(7) C5 0.048(10) 0.067(12) 0.053(11) 0.003(9) 0.017(9) 0.015(9) N2 0.031(6) 0.065(9) 0.051(8) 0.009(7) -0.002(6) 0.009(6) N3 0.022(6) 0.104(12) 0.031(7) 0.030(7) -0.016(6) 0.005(6) N1 0.038(9) 0.065(10) 0.051(10) -0.001(8) -0.011(7) 0.014(8) C1 0.044(11) 0.073(13) 0.053(12) -0.021(9) 0.025(9) -0.021(9) C2 0.054(11) 0.040(9) 0.066(13) -0.002(8) 0.034(10) 0.000(7) C6 0.023(8) 0.042(8) 0.060(11) 0.010(7) 0.004(7) 0.007(6) O 0.058(10) 0.075(11) 0.052(10) 0 0.015(8) 0 #------------------ MOLECULAR GEOMETRY --------------------------------------# _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 Bi I2 3.0449(11) . ? Bi I4 3.0668(11) . ? Bi I5 3.0726(13) . ? Bi I3 3.0844(11) . ? Bi I6 3.0989(13) . ? Bi I1 3.1295(12) . ? I7 I8 2.9269(13) 2_656 ? I7 I8 2.9269(13) . ? I9 I10 2.9200(12) . ? I9 I10 2.9200(12) 2_755 ? S2 C3 1.764(15) . ? S2 S1 2.040(6) . ? S3 C6 1.834(14) . ? S3 S4 2.025(6) . ? S1 C2 1.710(18) . ? S4 C7 1.794(16) . ? C8 C7 1.49(2) . ? C8 N4 1.55(2) . ? C3 C4 1.53(2) . ? C4 N2 1.506(18) . ? C5 C6 1.44(2) . ? C5 N3 1.49(2) . ? N1 C1 1.43(2) . ? C1 C2 1.57(2) . ? 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 I2 Bi I4 87.32(4) . . ? I2 Bi I5 91.19(4) . . ? I4 Bi I5 87.04(4) . . ? I2 Bi I3 91.03(4) . . ? I4 Bi I3 175.73(4) . . ? I5 Bi I3 89.05(3) . . ? I2 Bi I6 89.39(4) . . ? I4 Bi I6 88.96(3) . . ? I5 Bi I6 175.93(2) . . ? I3 Bi I6 94.97(3) . . ? I2 Bi I1 176.49(3) . . ? I4 Bi I1 89.41(4) . . ? I5 Bi I1 89.93(4) . . ? I3 Bi I1 92.32(4) . . ? I6 Bi I1 89.26(4) . . ? I8 I7 I8 179.09(8) 2_656 . ? I10 I9 I10 178.78(9) . 2_755 ? C3 S2 S1 103.5(5) . . ? C6 S3 S4 104.7(5) . . ? C2 S1 S2 104.5(6) . . ? C7 S4 S3 104.0(6) . . ? C7 C8 N4 110.5(13) . . ? C8 C7 S4 115.5(11) . . ? C4 C3 S2 112.3(12) . . ? N2 C4 C3 109.6(13) . . ? C6 C5 N3 113.4(15) . . ? N1 C1 C2 110.9(16) . . ? C1 C2 S1 117.6(12) . . ? C5 C6 S3 117.0(12) . . ? # Attachment 'revised_C4BiI6I3H2O(3).cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2006-07-13 at 23:58:29 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\program files\wingx\files\cifdoc.dat # CIF files read : sad data_2 _database_code_depnum_ccdc_archive 'CCDC 620820' _audit_creation_date 2006-07-13T23:58:29-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_formula_moiety '2(C4 H14 N2), (Bi I6), 0.5(I3), 0.5(I H4 O2)' _chemical_formula_sum 'C8 H30 Bi I8 N4 O' _chemical_formula_weight 1422.1 #------------------ UNIT CELL INFORMATION -----------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5276(17) _cell_length_b 10.405(2) _cell_length_c 17.504(4) _cell_angle_alpha 77.92(3) _cell_angle_beta 87.39(3) _cell_angle_gamma 85.29(3) _cell_volume 1513.0(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) #------------------ CRYSTAL INFORMATION -------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour brown _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 3.118 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1238 _exptl_absorpt_coefficient_mu 13.994 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.168 _exptl_absorpt_correction_T_max 0.350 #------------------ DATA COLLECTION INFORMATION -----------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device_type area_detector _diffrn_measurement_method CCD _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_detector_area_resol_mean 9 _diffrn_reflns_number 52561 _diffrn_reflns_av_R_equivalents 0.0549 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 30.03 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measured_fraction_theta_full 0.995 _reflns_number_total 8798 _reflns_number_gt 5330 _reflns_threshold_expression >2sigma(I) #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #------------------ REFINEMENT INFORMATION ----------------------------------# _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^)+(0.0355P)^2^+3.8232P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 8798 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.0943 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.001 _refine_diff_density_max 1.742 _refine_diff_density_min -1.637 #------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_group _atom_site_disorder_assembly Bi Bi 0.46559(3) 0.48933(2) 0.250356(16) 0.03959(8) Uani 1 d . . . I1 I 0.21947(7) 0.53901(6) 0.12870(3) 0.06356(16) Uani 1 d . . . I2 I 0.21524(6) 0.48845(6) 0.38714(3) 0.06007(15) Uani 1 d . . . I3 I 0.72284(6) 0.43372(5) 0.37984(3) 0.05314(14) Uani 1 d . . . I4 I 0.72173(6) 0.49914(6) 0.12543(3) 0.06023(15) Uani 1 d . . . I5 I 0.47763(7) 0.78880(5) 0.23718(3) 0.06031(16) Uani 1 d . . . I6 I 0.45435(6) 0.19036(5) 0.25686(3) 0.05641(15) Uani 1 d . . . I7 I 0 0 0 0.0757(3) Uani 1 d S . . I8 I 0.04900(9) 0.24591(7) 0.04850(4) 0.0869(2) Uani 1 d . . . I9 I 0 0 0.5 0.0975(3) Uani 1 d S . . O O 0.8635(8) 0.7385(6) 0.4242(4) 0.0843(19) Uiso 1 d . . . N1A N 0.0393(15) 0.2253(14) 0.3165(9) 0.075(4) Uani 0.67 d P 1 A H1A1 H -0.0094 0.3016 0.3227 0.112 Uiso 0.66 calc PR 1 A H1A2 H 0.1279 0.2405 0.2882 0.112 Uiso 0.66 calc PR 1 A H1A3 H 0.0621 0.1755 0.3631 0.112 Uiso 0.66 calc PR 1 A N1B N 0.019(4) 0.270(3) 0.265(2) 0.090(11) Uani 0.33 d P 2 A H1B1 H -0.0455 0.3376 0.2731 0.135 Uiso 0.33 calc PR 2 A H1B2 H 0.0612 0.2875 0.2172 0.135 Uiso 0.33 calc PR 2 A H1B3 H 0.0956 0.2555 0.2999 0.135 Uiso 0.33 calc PR 2 A N2 N -0.0764(13) -0.2938(9) 0.2462(8) 0.144(5) Uani 1 d . . . H2A H -0.1363 -0.2896 0.2887 0.216 Uiso 1 calc R . . H2B H -0.0027 -0.36 0.2573 0.216 Uiso 1 calc R . . H2C H -0.1359 -0.3072 0.2085 0.216 Uiso 1 calc R . . N3 N 0.5167(9) 0.7268(6) 0.4514(4) 0.0646(19) Uani 1 d . . . H3A H 0.6214 0.7184 0.4506 0.097 Uiso 1 calc R . . H3B H 0.4818 0.6977 0.4114 0.097 Uiso 1 calc R . . H3C H 0.4797 0.6799 0.4961 0.097 Uiso 1 calc R . . N4 N 0.4882(10) 0.2801(6) 0.0396(4) 0.073(2) Uani 1 d . . . H4A H 0.4538 0.3256 -0.0062 0.11 Uiso 1 calc R . . H4B H 0.5609 0.3235 0.0564 0.11 Uiso 1 calc R . . H4C H 0.4081 0.27 0.0742 0.11 Uiso 1 calc R . . C1 C -0.0663(10) 0.1550(8) 0.2751(6) 0.064(2) Uani 1 d . . . H1A H -0.1627 0.1389 0.3059 0.077 Uiso 0.5 calc PR 1 A H1B H -0.0938 0.2108 0.2251 0.077 Uiso 0.5 calc PR 1 A H1C H -0.1426 0.185 0.2345 0.077 Uiso 0.5 d PR 2 A H1D H -0.1255 0.1361 0.3243 0.077 Uiso 0.5 d PR 2 A C2 C 0.0104(11) 0.0273(8) 0.2619(6) 0.071(3) Uani 1 d . . A H2D H 0.0932 0.0455 0.2222 0.085 Uiso 1 calc R . . H2E H 0.0595 -0.019 0.3098 0.085 Uiso 1 calc R . . C3 C -0.0933(12) -0.0569(9) 0.2384(7) 0.089(3) Uani 1 d . . . H3D H -0.1454 -0.0101 0.1914 0.107 Uiso 1 calc R . A H3E H -0.1737 -0.0787 0.279 0.107 Uiso 1 calc R . . C4 C -0.0095(17) -0.1831(10) 0.2227(9) 0.125(5) Uani 1 d . . A H4D H 0.0096 -0.1713 0.1667 0.15 Uiso 1 calc R . . H4E H 0.0925 -0.1934 0.2465 0.15 Uiso 1 calc R . . C5 C 0.5235(12) 0.9276(8) 0.5036(6) 0.073(3) Uani 1 d . . . H5A H 0.6375 0.9157 0.5011 0.087 Uiso 1 calc R . . H5B H 0.4886 0.8811 0.5547 0.087 Uiso 1 calc R . . C6 C 0.4620(13) 0.8673(8) 0.4449(6) 0.086(3) Uani 1 d . . . H6A H 0.4926 0.9158 0.3936 0.103 Uiso 1 calc R . . H6B H 0.3479 0.8746 0.4491 0.103 Uiso 1 calc R . . C7 C 0.4665(11) 0.0640(8) 0.0063(6) 0.071(3) Uani 1 d . . . H7A H 0.4196 0.1093 -0.0424 0.085 Uiso 1 calc R . . H7B H 0.3805 0.0466 0.0443 0.085 Uiso 1 calc R . . C8 C 0.5555(13) 0.1538(10) 0.0305(8) 0.106(4) Uani 1 d . . . H8A H 0.6439 0.1689 -0.0063 0.127 Uiso 1 calc R . . H8B H 0.5987 0.1101 0.0804 0.127 Uiso 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Bi 0.03340(15) 0.04276(15) 0.04459(16) -0.01300(12) -0.00051(11) -0.00455(11) I1 0.0526(3) 0.0770(4) 0.0681(4) -0.0317(3) -0.0237(3) 0.0098(3) I2 0.0441(3) 0.0795(4) 0.0556(3) -0.0139(3) 0.0091(2) -0.0052(3) I3 0.0415(3) 0.0621(3) 0.0594(3) -0.0211(3) -0.0116(2) 0.0030(2) I4 0.0466(3) 0.0753(4) 0.0569(3) -0.0125(3) 0.0129(2) -0.0038(3) I5 0.0681(4) 0.0382(3) 0.0755(4) -0.0115(3) -0.0089(3) -0.0060(2) I6 0.0544(3) 0.0384(3) 0.0764(4) -0.0117(2) 0.0006(3) -0.0054(2) I7 0.0589(6) 0.0990(7) 0.0672(6) -0.0184(5) -0.0016(4) 0.0089(5) I8 0.0924(5) 0.0825(4) 0.0859(5) -0.0229(4) 0.0009(4) 0.0047(4) I9 0.0938(8) 0.0956(7) 0.1061(8) -0.0221(6) -0.0116(6) -0.0177(6) N1A 0.046(7) 0.069(9) 0.122(13) -0.047(9) 0.001(8) -0.010(7) N1B 0.09(2) 0.07(2) 0.12(3) -0.04(2) -0.03(2) 0.041(16) N2 0.111(9) 0.069(6) 0.245(15) -0.029(8) 0.048(9) -0.005(6) N3 0.080(5) 0.050(4) 0.070(5) -0.025(4) -0.002(4) -0.006(4) N4 0.100(6) 0.050(4) 0.076(5) -0.027(4) -0.010(4) -0.002(4) C1 0.057(6) 0.053(5) 0.083(6) -0.016(5) 0.004(5) 0.000(4) C2 0.069(7) 0.062(5) 0.080(7) -0.019(5) -0.002(5) 0.011(5) C3 0.077(7) 0.057(5) 0.145(10) -0.049(6) 0.029(7) -0.017(5) C4 0.148(12) 0.066(7) 0.173(13) -0.059(8) 0.079(10) -0.037(7) C5 0.076(7) 0.060(5) 0.088(7) -0.032(5) 0.001(5) 0.003(5) C6 0.100(8) 0.054(5) 0.110(8) -0.033(6) -0.032(7) 0.018(5) C7 0.075(6) 0.054(5) 0.091(7) -0.029(5) -0.015(5) 0.000(4) C8 0.075(8) 0.080(7) 0.179(13) -0.065(8) -0.038(8) 0.013(6) #------------------ MOLECULAR GEOMETRY --------------------------------------# _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 Bi I1 2.9957(11) . ? Bi I4 3.0120(11) . ? Bi I5 3.0859(8) . ? Bi I6 3.0982(8) . ? Bi I2 3.1337(11) . ? Bi I3 3.1590(11) . ? I7 I8 2.9257(10) 2 ? I7 I8 2.9257(10) . ? N1A C1 1.504(15) . ? N1B C1 1.43(3) . ? N2 C4 1.308(12) . ? N3 C6 1.480(10) . ? N4 C8 1.427(11) . ? C1 C2 1.489(11) . ? C2 C3 1.426(13) . ? C3 C4 1.512(13) . ? C5 C6 1.449(12) . ? C5 C5 1.508(16) 2_676 ? C7 C8 1.393(12) . ? C7 C7 1.461(15) 2_655 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag I1 Bi I4 90.54(2) . . ? I1 Bi I5 90.30(3) . . ? I4 Bi I5 89.12(4) . . ? I1 Bi I6 88.27(3) . . ? I4 Bi I6 89.31(4) . . ? I5 Bi I6 177.867(18) . . ? I1 Bi I2 92.87(2) . . ? I4 Bi I2 175.866(17) . . ? I5 Bi I2 88.52(4) . . ? I6 Bi I2 93.13(3) . . ? I1 Bi I3 179.248(19) . . ? I4 Bi I3 89.93(2) . . ? I5 Bi I3 90.30(3) . . ? I6 Bi I3 91.15(3) . . ? I2 Bi I3 86.68(2) . . ? I8 I7 I8 180.00(3) 2 . ? N1B C1 C2 121.5(14) . . ? N1B C1 N1A 37.0(11) . . ? C2 C1 N1A 111.8(9) . . ? C3 C2 C1 114.6(8) . . ? C2 C3 C4 112.8(10) . . ? N2 C4 C3 119.0(11) . . ? C6 C5 C5 115.4(10) . 2_676 ? C5 C6 N3 113.9(8) . . ? C8 C7 C7 122.7(11) . 2_655 ? C7 C8 N4 121.6(9) . . ? data_1 _database_code_depnum_ccdc_archive 'CCDC 628688' _audit_creation_date 2006-10-31T19:13:22-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_formula_moiety '4(C8 H16 N O2), 2(I3), (Bi I6), (H3 O)' _chemical_formula_sum 'C32 H67 Bi I12 N4 O9' _chemical_formula_weight 2383.68 #------------------ UNIT CELL INFORMATION -----------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/m 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 11.792(2) _cell_length_b 12.737(2) _cell_length_c 21.908(3) _cell_angle_alpha 90 _cell_angle_beta 94.290(10) _cell_angle_gamma 90 _cell_volume 3281.2(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 #------------------ CRYSTAL INFORMATION -------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.07 _exptl_crystal_density_diffrn 2.413 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2156 _exptl_absorpt_coefficient_mu 8.371 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.321 _exptl_absorpt_correction_T_max 0.529 #------------------ DATA COLLECTION INFORMATION -----------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device_type area_detector _diffrn_measurement_method CCD _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_detector_area_resol_mean 9 _diffrn_reflns_number 24342 _diffrn_reflns_av_R_equivalents 0.0355 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.52 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measured_fraction_theta_full 0.992 _reflns_number_total 3915 _reflns_number_gt 3032 _reflns_threshold_expression >2sigma(I) #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #------------------ REFINEMENT INFORMATION ----------------------------------# _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^)+(0.0338P)^2^+22.9584P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.00020(3) _refine_ls_number_reflns 3915 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0593 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_ref 0.0892 _refine_ls_wR_factor_gt 0.0833 _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_restrained_S_all 1.095 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.526 _refine_diff_density_min -1.2 _refine_diff_density_rms 0.137 #------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_group _atom_site_disorder_assembly Bi Bi 0 0 0 0.03738(14) Uani 1 d S . . I3 I 0.06199(6) 0 0.13837(3) 0.05274(18) Uani 1 d S . . I1 I 0 0.24255(5) 0 0.05603(19) Uani 1 d S . . I2 I 0.25603(5) 0 -0.01652(3) 0.05311(18) Uani 1 d S . . I4 I 0.49427(7) 0 0.14818(4) 0.0780(3) Uani 1 d S . . I5 I 0.48566(7) 0 0.28255(4) 0.0729(2) Uani 1 d S . . O3 O 0.1089(14) 0 0.4106(7) 0.068(4) Uani 0.5 d SP . . C7 C 0.1945(8) 0.2309(10) 0.2399(4) 0.102(4) Uani 1 d . . . H7A1 H 0.1705 0.1679 0.2177 0.122 Uiso 1 calc R . . H7A2 H 0.1381 0.2847 0.2297 0.122 Uiso 1 calc R . . C3 C 0.3577(10) 0.3469(9) 0.2570(4) 0.110(4) Uani 1 d . . . H3A1 H 0.3194 0.413 0.2478 0.132 Uiso 1 calc R . . H3A2 H 0.4357 0.3543 0.2464 0.132 Uiso 1 calc R . . N N 0.2706(7) 0.2089(7) 0.1078(3) 0.092(3) Uani 1 d . . . H1A1 H 0.2693 0.2343 0.0699 0.138 Uiso 1 calc R . . H1A2 H 0.2015 0.1863 0.1151 0.138 Uiso 1 calc R . . H1A3 H 0.3197 0.1559 0.1118 0.138 Uiso 1 calc R . . C4 C 0.3584(9) 0.3272(9) 0.3247(4) 0.098(3) Uani 1 d . . . H4A1 H 0.4132 0.2725 0.3361 0.118 Uiso 1 calc R . . H4A2 H 0.3825 0.3906 0.3465 0.118 Uiso 1 calc R . . C6 C 0.1954(9) 0.2087(9) 0.3068(3) 0.095(3) Uani 1 d . . . H6A1 H 0.1182 0.1965 0.3174 0.114 Uiso 1 calc R . . H6A2 H 0.239 0.1454 0.3161 0.114 Uiso 1 calc R . . C1 C 0.3059(8) 0.2924(7) 0.1519(3) 0.074(2) Uani 1 d . . . H1A4 H 0.2572 0.3529 0.1433 0.089 Uiso 1 calc R . . H1A5 H 0.3829 0.3133 0.1447 0.089 Uiso 1 calc R . . C8 C 0.2484(9) 0.2717(9) 0.4124(4) 0.089(3) Uani 1 d . . . C2 C 0.3027(7) 0.2653(6) 0.2184(3) 0.0600(18) Uani 1 d . . . H2A H 0.3528 0.2041 0.2242 0.072 Uiso 1 calc R . . C5 C 0.2446(8) 0.2952(8) 0.3437(4) 0.085(3) Uani 1 d . . . H5A H 0.194 0.3556 0.3363 0.102 Uiso 1 calc R . . O1 O 0.3082(8) 0.3351(8) 0.4475(3) 0.146(4) Uani 1 d . . . O2 O 0.1948(8) 0.2000(6) 0.4331(3) 0.122(3) Uani 1 d . . . I6 I 0.47972(16) 0 0.41378(5) 0.1473(6) Uani 1 d S . . 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 Bi 0.0386(3) 0.0430(3) 0.0309(2) 0 0.00468(18) 0 I3 0.0573(4) 0.0699(4) 0.0315(3) 0 0.0070(2) 0 I1 0.0739(4) 0.0365(3) 0.0602(4) 0 0.0212(3) 0 I2 0.0368(3) 0.0820(5) 0.0412(3) 0 0.0076(2) 0 I4 0.0802(5) 0.1011(6) 0.0530(4) 0 0.0081(4) 0 I5 0.0925(6) 0.0618(5) 0.0647(5) 0 0.0073(4) 0 O3 0.096(11) 0.039(7) 0.065(9) 0 -0.010(8) 0 C7 0.096(7) 0.162(10) 0.050(5) -0.020(6) 0.018(4) -0.063(7) C3 0.155(10) 0.130(9) 0.049(5) -0.009(5) 0.030(5) -0.082(8) N 0.104(6) 0.131(7) 0.042(4) -0.003(4) 0.010(4) -0.048(5) C4 0.109(7) 0.140(9) 0.046(5) -0.014(5) 0.012(5) -0.061(7) C6 0.117(7) 0.132(8) 0.038(4) -0.013(5) 0.022(4) -0.063(7) C1 0.113(7) 0.071(5) 0.038(4) 0.007(4) 0.008(4) -0.017(5) C8 0.106(7) 0.116(8) 0.047(5) -0.023(5) 0.023(5) -0.038(6) C2 0.071(5) 0.071(5) 0.039(4) 0.005(3) 0.007(3) -0.004(4) C5 0.113(7) 0.095(7) 0.050(5) -0.009(4) 0.024(5) -0.011(6) O1 0.213(9) 0.173(8) 0.054(4) -0.030(5) 0.031(5) -0.116(7) O2 0.183(8) 0.136(6) 0.051(4) -0.021(4) 0.039(4) -0.080(6) I6 0.2358(17) 0.1516(11) 0.0556(6) 0 0.0184(7) 0 #------------------ MOLECULAR GEOMETRY --------------------------------------# _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 Bi I3 3.0647(7) . ? Bi I3 3.0647(7) 5 ? Bi I2 3.0674(8) 5 ? Bi I2 3.0674(8) . ? Bi I1 3.0894(8) 5 ? Bi I1 3.0894(8) . ? I4 I5 2.9531(12) . ? I5 I6 2.8810(14) . ? C7 C2 1.459(11) . ? C7 C6 1.491(11) . ? C3 C2 1.462(11) . ? C3 C4 1.503(11) . ? N C1 1.475(10) . ? C4 C5 1.491(12) . ? C6 C5 1.460(12) . ? C1 C2 1.501(9) . ? C8 O2 1.218(11) . ? C8 O1 1.288(11) . ? C8 C5 1.531(12) . ? 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 I3 Bi I3 180.000(5) . 5 ? I3 Bi I2 92.712(19) . 5 ? I3 Bi I2 87.288(19) 5 5 ? I3 Bi I2 87.288(19) . . ? I3 Bi I2 92.712(19) 5 . ? I2 Bi I2 180.00(2) 5 . ? I3 Bi I1 90 . 5 ? I3 Bi I1 90 5 5 ? I2 Bi I1 90 5 5 ? I2 Bi I1 90 . 5 ? I3 Bi I1 90 . . ? I3 Bi I1 90 5 . ? I2 Bi I1 90 5 . ? I2 Bi I1 90 . . ? I1 Bi I1 180 5 . ? I6 I5 I4 179.42(5) . . ? C2 C7 C6 115.6(8) . . ? C2 C3 C4 115.0(8) . . ? C5 C4 C3 112.4(8) . . ? C5 C6 C7 112.0(8) . . ? N C1 C2 116.3(7) . . ? O2 C8 O1 121.5(8) . . ? O2 C8 C5 122.4(8) . . ? O1 C8 C5 116.1(9) . . ? C7 C2 C3 112.7(7) . . ? C7 C2 C1 117.9(7) . . ? C3 C2 C1 110.9(7) . . ? C6 C5 C4 112.4(8) . . ? C6 C5 C8 112.2(8) . . ? C4 C5 C8 111.5(8) . . ?