# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 _publ_contact_author_name 'Tatsuro Imakubo' _publ_contact_author_address ; Imakubo Initiative Research Unit RIKEN 2-1 Hirosawa Wako Saitama 351-0198 JAPAN ; _publ_contact_author_email IMAKUBO@RIKEN.JP _publ_section_title ; Supramolecular organic conductors based on diiodo-TTFs and spherical halide ion X- (X = Cl, Br) ; loop_ _publ_author_name 'Tatsuro Imakubo' 'Katel Herve' 'Lahcene Ouahab' 'Takashi Shirahata' data_diedost _database_code_depnum_ccdc_archive 'CCDC 281968' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H8 Cl I4 O4 S4 Se4' _chemical_formula_weight 1251.35 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' 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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 26.823(6) _cell_length_b 7.876(2) _cell_length_c 13.259(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.994(6) _cell_angle_gamma 90.00 _cell_volume 2785.8(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293 _cell_measurement_reflns_used 2206 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 27.29 _exptl_crystal_description block _exptl_crystal_colour black _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.984 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2260 _exptl_absorpt_coefficient_mu 10.121 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.1864 _exptl_absorpt_correction_T_max 0.4982 _exptl_absorpt_process_details ; SADABS; Sheldrick 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293 _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 8.366 _diffrn_standards_number 93 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2.0 _diffrn_reflns_number 9989 _diffrn_reflns_av_R_equivalents 0.0492 _diffrn_reflns_av_sigmaI/netI 0.0695 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 28.41 _reflns_number_total 3469 _reflns_number_gt 2815 _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^)+(0.0318P)^2^+27.0901P] 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 3469 _refine_ls_number_parameters 150 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0643 _refine_ls_R_factor_gt 0.0501 _refine_ls_wR_factor_ref 0.1194 _refine_ls_wR_factor_gt 0.1131 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 I1 I 0.09363(2) 0.22782(8) 0.66044(4) 0.03750(16) Uani 1 1 d . . . I2 I 0.074820(18) 0.20708(7) 0.37434(4) 0.03468(16) Uani 1 1 d . . . Se1 Se 0.20496(3) 0.40737(11) 0.62607(6) 0.0318(2) Uani 1 1 d . . . Se2 Se 0.18540(3) 0.40656(11) 0.38564(6) 0.0319(2) Uani 1 1 d . . . S1 S 0.31326(7) 0.6001(3) 0.60321(15) 0.0329(4) Uani 1 1 d . . . S2 S 0.29358(7) 0.5999(3) 0.37886(15) 0.0349(5) Uani 1 1 d . . . O1 O 0.4033(2) 0.7315(8) 0.5859(5) 0.0392(14) Uani 1 1 d . . . O2 O 0.3827(2) 0.7344(8) 0.3683(5) 0.0417(15) Uani 1 1 d . . . C1 C 0.1434(3) 0.3200(10) 0.5627(6) 0.0260(15) Uani 1 1 d . . . C2 C 0.1359(3) 0.3186(10) 0.4624(5) 0.0257(15) Uani 1 1 d . . . C3 C 0.2288(3) 0.4704(10) 0.5018(5) 0.0277(15) Uani 1 1 d . . . C4 C 0.2729(3) 0.5471(10) 0.4957(5) 0.0266(15) Uani 1 1 d . . . C5 C 0.3595(3) 0.6783(11) 0.5328(6) 0.0333(18) Uani 1 1 d . . . C6 C 0.3504(3) 0.6806(10) 0.4331(6) 0.0306(17) Uani 1 1 d . . . C7 C 0.4392(4) 0.773(2) 0.5187(10) 0.107(7) Uani 1 1 d . . . H7A H 0.4505 0.8876 0.5358 0.129 Uiso 1 1 calc R . . H7B H 0.4677 0.6992 0.5359 0.129 Uiso 1 1 calc R . . C8 C 0.4297(4) 0.768(2) 0.4198(10) 0.081(4) Uani 1 1 d . . . H8A H 0.4524 0.6849 0.3962 0.097 Uiso 1 1 calc R . . H8B H 0.4400 0.8775 0.3951 0.097 Uiso 1 1 calc R . . Cl1 Cl 0.0000 0.9699(4) 0.2500 0.0393(7) Uani 1 2 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 I1 0.0320(3) 0.0489(4) 0.0337(3) 0.0039(2) 0.0132(2) -0.0004(2) I2 0.0221(2) 0.0486(4) 0.0327(3) -0.0007(2) -0.0004(2) -0.0018(2) Se1 0.0265(4) 0.0454(5) 0.0236(4) 0.0000(3) 0.0029(3) -0.0038(3) Se2 0.0257(4) 0.0466(5) 0.0236(4) 0.0012(3) 0.0042(3) -0.0043(3) S1 0.0233(9) 0.0485(13) 0.0267(9) 0.0007(8) 0.0024(7) -0.0027(8) S2 0.0250(9) 0.0521(13) 0.0276(10) -0.0010(8) 0.0032(8) -0.0029(9) O1 0.021(3) 0.056(4) 0.040(3) -0.001(3) -0.005(2) -0.004(3) O2 0.029(3) 0.062(4) 0.038(3) 0.000(3) 0.017(3) -0.010(3) C1 0.019(3) 0.033(4) 0.028(4) 0.001(3) 0.011(3) 0.001(3) C2 0.024(3) 0.032(4) 0.022(3) 0.003(3) 0.003(3) -0.001(3) C3 0.026(4) 0.035(4) 0.023(3) 0.000(3) 0.004(3) 0.004(3) C4 0.022(3) 0.033(4) 0.025(4) 0.002(3) 0.007(3) 0.002(3) C5 0.025(4) 0.049(5) 0.027(4) 0.002(3) 0.006(3) 0.005(3) C6 0.022(3) 0.038(5) 0.032(4) 0.001(3) 0.003(3) -0.003(3) C7 0.035(6) 0.23(2) 0.056(8) 0.025(10) 0.004(6) -0.052(9) C8 0.038(6) 0.139(13) 0.070(8) -0.009(8) 0.025(6) -0.032(7) Cl1 0.0221(12) 0.0588(19) 0.0365(15) 0.000 0.0008(11) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C1 2.086(7) . ? I2 C2 2.103(7) . ? Se1 C3 1.894(7) . ? Se1 C1 1.901(7) . ? Se2 C2 1.887(7) . ? Se2 C3 1.898(8) . ? S1 C5 1.741(8) . ? S1 C4 1.749(8) . ? S2 C6 1.736(8) . ? S2 C4 1.749(7) . ? O1 C5 1.371(10) . ? O1 C7 1.415(12) . ? O2 C6 1.351(9) . ? O2 C8 1.395(13) . ? C1 C2 1.324(10) . ? C3 C4 1.339(10) . ? C5 C6 1.320(11) . ? C7 C8 1.311(18) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? 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 C3 Se1 C1 93.8(3) . . ? C2 Se2 C3 93.7(3) . . ? C5 S1 C4 93.6(4) . . ? C6 S2 C4 93.8(4) . . ? C5 O1 C7 110.5(7) . . ? C6 O2 C8 110.9(7) . . ? C2 C1 Se1 118.7(5) . . ? C2 C1 I1 125.6(6) . . ? Se1 C1 I1 115.7(4) . . ? C1 C2 Se2 119.8(6) . . ? C1 C2 I2 126.1(5) . . ? Se2 C2 I2 113.9(3) . . ? C4 C3 Se1 123.5(6) . . ? C4 C3 Se2 122.7(6) . . ? Se1 C3 Se2 113.8(4) . . ? C3 C4 S1 122.3(6) . . ? C3 C4 S2 121.7(6) . . ? S1 C4 S2 116.0(4) . . ? C6 C5 O1 124.7(7) . . ? C6 C5 S1 118.3(6) . . ? O1 C5 S1 117.0(6) . . ? C5 C6 O2 125.2(7) . . ? C5 C6 S2 118.3(6) . . ? O2 C6 S2 116.4(6) . . ? C8 C7 O1 123.3(10) . . ? C8 C7 H7A 106.5 . . ? O1 C7 H7A 106.5 . . ? C8 C7 H7B 106.5 . . ? O1 C7 H7B 106.5 . . ? H7A C7 H7B 106.5 . . ? C7 C8 O2 124.5(9) . . ? C7 C8 H8A 106.2 . . ? O2 C8 H8A 106.2 . . ? C7 C8 H8B 106.2 . . ? O2 C8 H8B 106.2 . . ? H8A C8 H8B 106.4 . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 28.41 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 1.247 _refine_diff_density_min -0.897 _refine_diff_density_rms 0.209 data_dietbr_face _database_code_depnum_ccdc_archive 'CCDC 281969' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H12 Br I4 O2 S12' _chemical_formula_weight 1208.49 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' 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' Br Br -0.2901 2.4595 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 7.8146(14) _cell_length_b 30.306(5) _cell_length_c 13.253(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3138.7(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6116 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 28.12 _exptl_crystal_description thick _exptl_crystal_colour black _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 2.557 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2252 _exptl_absorpt_coefficient_mu 6.061 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.1758 _exptl_absorpt_correction_T_max 0.7387 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 21950 _diffrn_reflns_av_R_equivalents 0.0771 _diffrn_reflns_av_sigmaI/netI 0.0442 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -39 _diffrn_reflns_limit_k_max 40 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.34 _diffrn_reflns_theta_max 28.42 _reflns_number_total 4016 _reflns_number_gt 3098 _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^)+(0.0933P)^2^+31.4388P] 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 4016 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0752 _refine_ls_R_factor_gt 0.0612 _refine_ls_wR_factor_ref 0.1880 _refine_ls_wR_factor_gt 0.1787 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 I1 I 1.01435(8) 0.680012(19) 0.81964(4) 0.03829(19) Uani 1 1 d . . . I2 I 1.03835(8) 0.678181(19) 0.52994(4) 0.0408(2) Uani 1 1 d . . . S1 S 0.8773(3) 0.58031(7) 0.78407(16) 0.0380(5) Uani 1 1 d . . . S2 S 0.8957(3) 0.57906(7) 0.56439(16) 0.0408(5) Uani 1 1 d . . . C2 C 0.9610(10) 0.6273(3) 0.6248(6) 0.0331(16) Uani 1 1 d . . . C1 C 0.9541(11) 0.6281(3) 0.7253(6) 0.0343(17) Uani 1 1 d . . . S5 S 0.5301(3) 0.39658(8) 0.79576(17) 0.0389(5) Uani 1 1 d . . . S3 S 0.7006(3) 0.48348(7) 0.78143(15) 0.0370(5) Uani 1 1 d . . . S4 S 0.7173(3) 0.48336(8) 0.56136(16) 0.0430(5) Uani 1 1 d . . . S6 S 0.5489(4) 0.39895(9) 0.53334(17) 0.0528(7) Uani 1 1 d . . . C5 C 0.6088(10) 0.4383(2) 0.7192(6) 0.0302(15) Uani 1 1 d . . . C4 C 0.7574(12) 0.5116(3) 0.6719(6) 0.0351(18) Uani 1 1 d . . . C3 C 0.8333(12) 0.5519(3) 0.6736(6) 0.0344(17) Uani 1 1 d . . . C6 C 0.6177(11) 0.4385(3) 0.6184(6) 0.0310(16) Uani 1 1 d . . . C8 C 0.4696(15) 0.3565(3) 0.6131(8) 0.054(3) Uani 1 1 d . . . H8A H 0.3501 0.3626 0.6272 0.065 Uiso 1 1 calc R . . H8B H 0.4744 0.3289 0.5764 0.065 Uiso 1 1 calc R . . C7 C 0.5598(13) 0.3506(3) 0.7107(8) 0.045(2) Uani 1 1 d . . . H7A H 0.6811 0.3468 0.6978 0.054 Uiso 1 1 calc R . . H7B H 0.5183 0.3239 0.7429 0.054 Uiso 1 1 calc R . . Br1 Br 0.1810(3) 0.7500 0.37291(16) 0.0806(6) Uani 1 2 d S . . O1 O 0.0337(16) 0.7500 -0.0223(8) 0.059(3) Uani 1 2 d S . . O2 O 0.2555(17) 0.7500 0.1383(9) 0.084(4) Uani 1 2 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 I1 0.0441(3) 0.0342(3) 0.0365(3) -0.0028(2) 0.0005(2) -0.0037(2) I2 0.0495(4) 0.0370(3) 0.0359(3) 0.0052(2) -0.0022(2) -0.0041(2) S1 0.0525(13) 0.0338(10) 0.0276(9) -0.0007(8) -0.0001(9) -0.0042(9) S2 0.0586(14) 0.0359(10) 0.0279(9) 0.0008(8) -0.0001(9) -0.0042(10) C2 0.030(4) 0.032(4) 0.038(4) 0.004(3) -0.001(3) 0.000(3) C1 0.038(4) 0.027(4) 0.037(4) 0.000(3) -0.001(3) -0.001(3) S5 0.0467(12) 0.0390(11) 0.0308(10) 0.0025(9) 0.0046(9) -0.0029(9) S3 0.0512(12) 0.0355(10) 0.0243(9) -0.0028(8) 0.0009(9) -0.0021(9) S4 0.0658(15) 0.0389(11) 0.0242(9) -0.0011(8) 0.0021(10) -0.0086(11) S6 0.0826(19) 0.0465(13) 0.0293(11) -0.0042(9) -0.0073(11) -0.0161(13) C5 0.034(4) 0.029(4) 0.028(4) -0.001(3) -0.002(3) 0.000(3) C4 0.046(5) 0.035(4) 0.025(4) -0.002(3) 0.001(3) 0.005(4) C3 0.042(4) 0.037(4) 0.025(4) 0.002(3) 0.000(3) 0.002(4) C6 0.038(4) 0.027(4) 0.028(4) -0.003(3) -0.001(3) -0.002(3) C8 0.076(7) 0.037(5) 0.050(6) -0.009(4) 0.010(5) -0.014(5) C7 0.051(5) 0.037(4) 0.047(5) 0.004(4) 0.003(4) -0.002(4) Br1 0.1001(15) 0.0787(12) 0.0632(11) 0.000 0.0170(11) 0.000 O1 0.092(8) 0.045(5) 0.039(5) 0.000 -0.007(5) 0.000 O2 0.066(8) 0.143(13) 0.045(6) 0.000 0.004(6) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C1 2.063(8) . ? I2 C2 2.079(8) . ? S1 C3 1.733(8) . ? S1 C1 1.751(8) . ? S2 C3 1.735(8) . ? S2 C2 1.743(9) . ? C2 C1 1.334(12) . ? S5 C5 1.735(8) . ? S5 C7 1.809(10) . ? S3 C4 1.741(8) . ? S3 C5 1.751(8) . ? S4 C4 1.726(8) . ? S4 C6 1.739(8) . ? S6 C6 1.732(8) . ? S6 C8 1.776(10) . ? C5 C6 1.338(11) . ? C4 C3 1.358(12) . ? C8 C7 1.485(15) . ? 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 C3 S1 C1 95.9(4) . . ? C3 S2 C2 95.6(4) . . ? C1 C2 S2 117.5(6) . . ? C1 C2 I2 127.0(6) . . ? S2 C2 I2 115.5(4) . . ? C2 C1 S1 116.3(6) . . ? C2 C1 I1 127.6(6) . . ? S1 C1 I1 116.1(4) . . ? C5 S5 C7 98.8(4) . . ? C4 S3 C5 95.4(4) . . ? C4 S4 C6 95.7(4) . . ? C6 S6 C8 102.8(4) . . ? C6 C5 S5 127.3(6) . . ? C6 C5 S3 116.5(6) . . ? S5 C5 S3 116.1(4) . . ? C3 C4 S4 122.6(6) . . ? C3 C4 S3 122.6(6) . . ? S4 C4 S3 114.8(5) . . ? C4 C3 S1 123.2(6) . . ? C4 C3 S2 122.4(6) . . ? S1 C3 S2 114.4(5) . . ? C5 C6 S6 129.1(6) . . ? C5 C6 S4 117.4(6) . . ? S6 C6 S4 113.4(4) . . ? C7 C8 S6 116.2(7) . . ? C8 C7 S5 112.8(7) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.42 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.096 _refine_diff_density_min -3.381 _refine_diff_density_rms 0.286 data_rt21 _database_code_depnum_ccdc_archive 'CCDC 281970' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H10 Cl3 I4 S4 Se8' _chemical_formula_weight 1588.12 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' Cl Cl 0.1484 0.1585 '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' Se Se -0.0929 2.2259 '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' _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 7.876(3) _cell_length_b 14.217(5) _cell_length_c 30.851(11) _cell_angle_alpha 90.00 _cell_angle_beta 95.721(7) _cell_angle_gamma 90.00 _cell_volume 3437(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2409 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 26.41 _exptl_crystal_description plate _exptl_crystal_colour black _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 3.069 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2844 _exptl_absorpt_coefficient_mu 12.588 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 11625 _diffrn_reflns_av_R_equivalents 0.0978 _diffrn_reflns_av_sigmaI/netI 0.1415 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 28.43 _reflns_number_total 4264 _reflns_number_gt 2802 _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^)+(0.0930P)^2^+388.2758P] 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 4264 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1525 _refine_ls_R_factor_gt 0.1135 _refine_ls_wR_factor_ref 0.3006 _refine_ls_wR_factor_gt 0.2782 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.100 _refine_ls_shift/su_max 0.010 _refine_ls_shift/su_mean 0.001 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 I2 I 1.39664(19) 0.59841(13) 1.12646(6) 0.0446(5) Uani 1 1 d . . . I1 I 1.01106(18) 0.47765(11) 1.16361(5) 0.0360(4) Uani 1 1 d . . . Se4 Se 0.9256(3) 0.70459(17) 0.93700(7) 0.0334(5) Uani 1 1 d . B . Se1 Se 0.8195(3) 0.54136(16) 1.06318(7) 0.0314(5) Uani 1 1 d . . . Se3 Se 0.5922(3) 0.60574(17) 0.96754(7) 0.0344(5) Uani 1 1 d . B . Se2 Se 1.1518(3) 0.64199(16) 1.03265(7) 0.0323(5) Uani 1 1 d . . . S2 S 0.7339(8) 0.7644(4) 0.8486(2) 0.0406(13) Uani 1 1 d . B . S1 S 0.3729(7) 0.6562(5) 0.8821(2) 0.0400(13) Uani 1 1 d . . . C2 C 1.161(3) 0.5872(15) 1.0889(7) 0.031(4) Uani 1 1 d . . . C1 C 1.025(3) 0.5457(15) 1.1024(6) 0.028(4) Uani 1 1 d . . . C5 C 0.575(3) 0.6657(14) 0.9114(7) 0.030(4) Uani 1 1 d . B . C6 C 0.716(3) 0.7074(14) 0.8990(7) 0.031(4) Uani 1 1 d . . . C3 C 0.919(3) 0.6131(16) 1.0187(7) 0.031(4) Uani 1 1 d . B . C4 C 0.825(2) 0.6384(14) 0.9814(6) 0.026(4) Uani 1 1 d . . . Cl2 Cl 0.3249(17) 0.4243(12) 0.7623(4) 0.127(5) Uani 1 1 d . . . Cl1 Cl 0.0000 0.6289(7) 0.7500 0.049(2) Uani 1 2 d S . . C9 C 0.5000 0.356(4) 0.7500 0.072(13) Uani 1 2 d S . . H9 H 0.4648 0.3158 0.7253 0.086 Uiso 1 1 d R . . C8 C 0.559(6) 0.711(5) 0.8178(12) 0.15(3) Uani 1 1 d . . . H8A H 0.4929 0.7639 0.8057 0.180 Uiso 1 1 calc R A 1 H8B H 0.6098 0.6833 0.7934 0.180 Uiso 1 1 calc R A 1 C7A C 0.439(6) 0.648(4) 0.8256(17) 0.044(13) Uani 0.50 1 d P B 1 H7A1 H 0.4812 0.5852 0.8210 0.053 Uiso 0.50 1 calc PR B 1 H7A2 H 0.3391 0.6579 0.8048 0.053 Uiso 0.50 1 calc PR B 1 C7B C 0.390(5) 0.706(5) 0.831(2) 0.057(17) Uani 0.50 1 d P B 2 H7B1 H 0.3188 0.6708 0.8095 0.068 Uiso 0.50 1 calc PR B 2 H7B2 H 0.3446 0.7698 0.8312 0.068 Uiso 0.50 1 calc PR B 2 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 I2 0.0300(7) 0.0499(10) 0.0531(10) 0.0107(8) -0.0004(6) -0.0082(7) I1 0.0360(7) 0.0361(8) 0.0363(8) 0.0046(6) 0.0050(5) -0.0069(6) Se4 0.0265(9) 0.0374(12) 0.0365(12) 0.0093(9) 0.0036(8) -0.0089(9) Se1 0.0263(9) 0.0322(12) 0.0361(11) 0.0076(9) 0.0046(8) -0.0086(8) Se3 0.0272(10) 0.0355(12) 0.0404(12) 0.0085(10) 0.0025(8) -0.0123(9) Se2 0.0245(9) 0.0356(12) 0.0370(12) 0.0062(9) 0.0046(8) -0.0093(8) S2 0.044(3) 0.036(3) 0.041(3) 0.012(3) -0.001(2) -0.007(3) S1 0.025(2) 0.039(3) 0.054(4) 0.004(3) -0.004(2) -0.003(2) C2 0.029(9) 0.028(11) 0.034(11) 0.009(9) -0.001(8) -0.011(8) C1 0.031(9) 0.033(11) 0.022(9) 0.003(8) 0.005(7) -0.010(8) C5 0.043(11) 0.018(9) 0.031(11) 0.000(8) 0.013(8) -0.012(8) C6 0.035(10) 0.014(9) 0.045(13) -0.001(9) 0.012(9) -0.003(8) C3 0.032(10) 0.033(11) 0.031(11) 0.004(9) 0.012(8) -0.010(9) C4 0.018(8) 0.029(10) 0.030(10) -0.008(8) 0.004(7) -0.020(7) Cl2 0.100(9) 0.174(15) 0.111(10) 0.029(9) 0.025(7) 0.047(10) Cl1 0.081(6) 0.038(5) 0.029(4) 0.000 0.009(4) 0.000 C9 0.08(3) 0.06(3) 0.07(3) 0.000 -0.01(2) 0.000 C8 0.12(4) 0.28(8) 0.04(2) 0.03(3) -0.04(2) -0.11(5) C7A 0.03(2) 0.05(3) 0.06(3) -0.02(3) 0.01(2) -0.03(2) C7B 0.008(18) 0.09(5) 0.08(4) -0.02(4) 0.013(19) 0.00(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I2 C2 2.09(2) . ? I1 C1 2.134(19) . ? Se4 C4 1.898(19) . ? Se4 C6 1.93(2) . ? Se1 C1 1.92(2) . ? Se1 C3 1.94(2) . ? Se3 C4 1.898(17) . ? Se3 C5 1.92(2) . ? Se2 C3 1.89(2) . ? Se2 C2 1.90(2) . ? S2 C8 1.77(4) . ? S2 C6 1.77(2) . ? S1 C7B 1.75(7) . ? S1 C5 1.75(2) . ? S1 C7A 1.87(5) . ? C2 C1 1.33(3) . ? C5 C6 1.35(3) . ? C3 C4 1.35(3) . ? Cl2 C9 1.76(3) . ? C9 Cl2 1.76(3) 2_656 ? C8 C7A 1.34(6) . ? C8 C7B 1.43(6) . ? 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 C4 Se4 C6 93.2(8) . . ? C1 Se1 C3 93.2(9) . . ? C4 Se3 C5 94.2(9) . . ? C3 Se2 C2 93.9(9) . . ? C8 S2 C6 98.5(16) . . ? C7B S1 C5 106.5(16) . . ? C7B S1 C7A 30(3) . . ? C5 S1 C7A 99.4(17) . . ? C1 C2 Se2 120.7(15) . . ? C1 C2 I2 124.0(16) . . ? Se2 C2 I2 115.2(9) . . ? C2 C1 Se1 118.2(15) . . ? C2 C1 I1 126.4(15) . . ? Se1 C1 I1 115.4(9) . . ? C6 C5 S1 128.3(18) . . ? C6 C5 Se3 117.6(17) . . ? S1 C5 Se3 114.1(10) . . ? C5 C6 S2 126.0(18) . . ? C5 C6 Se4 120.0(17) . . ? S2 C6 Se4 114.0(11) . . ? C4 C3 Se2 124.9(14) . . ? C4 C3 Se1 121.2(15) . . ? Se2 C3 Se1 113.9(11) . . ? C3 C4 Se3 124.0(14) . . ? C3 C4 Se4 120.9(13) . . ? Se3 C4 Se4 115.0(10) . . ? Cl2 C9 Cl2 113(3) . 2_656 ? C7A C8 C7B 39(4) . . ? C7A C8 S2 136(4) . . ? C7B C8 S2 124(4) . . ? C8 C7A S1 113(4) . . ? C8 C7B S1 116(4) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 28.43 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 3.735 _refine_diff_density_min -2.249 _refine_diff_density_rms 0.481 data_dietse6_face _database_code_depnum_ccdc_archive 'CCDC 281971' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H10 Br Cl2 I4 S4 Se8' _chemical_formula_weight 1632.58 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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' _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 7.834(3) _cell_length_b 14.257(5) _cell_length_c 30.885(9) _cell_angle_alpha 90.00 _cell_angle_beta 95.789(7) _cell_angle_gamma 90.00 _cell_volume 3431.8(19) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1918 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 25.46 _exptl_crystal_description plate _exptl_crystal_colour black _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 3.160 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2916 _exptl_absorpt_coefficient_mu 13.694 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.1250 _exptl_absorpt_correction_T_max 0.5476 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 12430 _diffrn_reflns_av_R_equivalents 0.0950 _diffrn_reflns_av_sigmaI/netI 0.1210 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_theta_min 1.33 _diffrn_reflns_theta_max 28.54 _reflns_number_total 4304 _reflns_number_gt 2518 _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^)+(0.0365P)^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_number_reflns 4304 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1015 _refine_ls_R_factor_gt 0.0544 _refine_ls_wR_factor_ref 0.1126 _refine_ls_wR_factor_gt 0.1004 _refine_ls_goodness_of_fit_ref 0.890 _refine_ls_restrained_S_all 0.890 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I2 I 1.39799(8) 0.59723(6) 1.12464(2) 0.0426(2) Uani 1 1 d . . . I1 I 1.01153(8) 0.47776(5) 1.16193(2) 0.03420(19) Uani 1 1 d . . . Se4 Se 0.92517(12) 0.70447(8) 0.93728(3) 0.0347(3) Uani 1 1 d . B . Se1 Se 0.82063(12) 0.54196(8) 1.06244(3) 0.0326(3) Uani 1 1 d . . . Se3 Se 0.59143(12) 0.60698(8) 0.96775(3) 0.0355(3) Uani 1 1 d . B . Se2 Se 1.15198(12) 0.64115(8) 1.03185(3) 0.0336(3) Uani 1 1 d . . . S2 S 0.7344(4) 0.7642(2) 0.84973(8) 0.0431(8) Uani 1 1 d . B . S1 S 0.3745(3) 0.6571(2) 0.88346(9) 0.0456(8) Uani 1 1 d . . . C2 C 1.1599(12) 0.5858(7) 1.0881(3) 0.029(2) Uani 1 1 d . . . C1 C 1.0220(12) 0.5456(7) 1.1015(3) 0.028(2) Uani 1 1 d . . . C5 C 0.5755(12) 0.6665(7) 0.9124(3) 0.032(2) Uani 1 1 d . B . C6 C 0.7168(11) 0.7050(7) 0.8993(3) 0.029(2) Uani 1 1 d . . . C3 C 0.9158(11) 0.6131(7) 1.0188(3) 0.031(2) Uani 1 1 d . B . C4 C 0.8279(10) 0.6379(7) 0.9820(3) 0.023(2) Uani 1 1 d . . . Cl2 Cl 0.3310(6) 0.4354(4) 0.76333(15) 0.129(2) Uani 1 1 d . . . Br1 Br 1.0000 0.63036(13) 0.7500 0.0547(5) Uani 1 2 d S . . C9 C 0.5000 0.3709(13) 0.7500 0.064(6) Uani 1 2 d S . . H9 H 0.4648 0.3307 0.7253 0.077 Uiso 1 1 d R . . C8 C 0.558(2) 0.7131(16) 0.8164(4) 0.143(10) Uani 1 1 d . . . H8A H 0.5203 0.7605 0.7950 0.172 Uiso 1 1 calc R A 1 H8B H 0.6068 0.6628 0.8004 0.172 Uiso 1 1 calc R A 1 C7 C 0.4209(18) 0.6794(18) 0.8299(4) 0.162(12) Uani 1 1 d . B 1 H7A H 0.4026 0.6200 0.8149 0.194 Uiso 1 1 calc R B 1 H7B H 0.3295 0.7204 0.8178 0.194 Uiso 1 1 calc R B 1 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 I2 0.0280(4) 0.0589(5) 0.0389(4) 0.0104(4) -0.0065(3) -0.0081(4) I1 0.0341(4) 0.0434(4) 0.0246(3) 0.0055(3) 0.0008(3) -0.0058(3) Se4 0.0272(5) 0.0496(8) 0.0265(5) 0.0090(5) -0.0007(4) -0.0092(5) Se1 0.0258(5) 0.0454(7) 0.0262(5) 0.0081(5) 0.0008(4) -0.0082(5) Se3 0.0272(5) 0.0476(7) 0.0309(5) 0.0083(5) -0.0014(4) -0.0100(5) Se2 0.0255(5) 0.0477(7) 0.0273(5) 0.0067(5) 0.0013(4) -0.0090(5) S2 0.0437(16) 0.053(2) 0.0296(14) 0.0136(14) -0.0085(12) -0.0136(15) S1 0.0279(14) 0.061(2) 0.0446(16) 0.0041(16) -0.0112(12) -0.0046(14) C2 0.030(5) 0.030(6) 0.025(5) 0.005(5) -0.003(4) -0.005(5) C1 0.035(5) 0.025(6) 0.024(5) 0.004(4) 0.004(4) 0.005(5) C5 0.032(5) 0.032(6) 0.030(5) -0.002(5) -0.002(4) 0.000(5) C6 0.024(5) 0.030(6) 0.032(5) 0.006(5) -0.001(4) 0.004(4) C3 0.024(5) 0.045(7) 0.025(5) 0.003(5) 0.005(4) 0.003(5) C4 0.016(4) 0.027(6) 0.027(5) 0.003(4) 0.003(4) -0.012(4) Cl2 0.101(4) 0.181(6) 0.103(4) 0.009(4) 0.005(3) 0.063(4) Br1 0.0867(13) 0.0454(11) 0.0310(8) 0.000 0.0015(8) 0.000 C9 0.113(16) 0.046(12) 0.035(9) 0.000 0.013(10) 0.000 C8 0.105(13) 0.27(3) 0.043(8) 0.014(13) -0.032(9) -0.117(16) C7 0.079(11) 0.38(4) 0.026(7) 0.026(13) -0.008(7) -0.119(17) _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 I2 C2 2.087(9) . ? I1 C1 2.113(9) . ? Se4 C4 1.898(9) . ? Se4 C6 1.911(9) . ? Se1 C1 1.887(9) . ? Se1 C3 1.898(10) . ? Se3 C5 1.900(10) . ? Se3 C4 1.912(8) . ? Se2 C3 1.896(9) . ? Se2 C2 1.904(9) . ? S2 C6 1.767(10) . ? S2 C8 1.792(13) . ? S1 C5 1.736(10) . ? S1 C7 1.758(12) . ? C2 C1 1.324(13) . ? C5 C6 1.334(13) . ? C3 C4 1.317(12) . ? Cl2 C9 1.696(11) . ? C9 Cl2 1.696(11) 2_656 ? C9 H9 0.9710 . ? C8 C7 1.285(17) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? 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 C4 Se4 C6 93.9(4) . . ? C1 Se1 C3 94.3(4) . . ? C5 Se3 C4 94.5(4) . . ? C3 Se2 C2 92.7(4) . . ? C6 S2 C8 100.4(6) . . ? C5 S1 C7 102.0(6) . . ? C1 C2 Se2 120.7(7) . . ? C1 C2 I2 125.3(7) . . ? Se2 C2 I2 113.9(5) . . ? C2 C1 Se1 118.0(7) . . ? C2 C1 I1 125.4(7) . . ? Se1 C1 I1 116.6(5) . . ? C6 C5 S1 127.7(8) . . ? C6 C5 Se3 118.4(7) . . ? S1 C5 Se3 113.8(5) . . ? C5 C6 S2 126.8(7) . . ? C5 C6 Se4 119.7(7) . . ? S2 C6 Se4 113.4(5) . . ? C4 C3 Se2 122.7(7) . . ? C4 C3 Se1 123.2(7) . . ? Se2 C3 Se1 114.0(5) . . ? C3 C4 Se4 123.3(7) . . ? C3 C4 Se3 123.1(7) . . ? Se4 C4 Se3 113.5(4) . . ? Cl2 C9 Cl2 114.4(11) 2_656 . ? Cl2 C9 H9 107.2 2_656 . ? Cl2 C9 H9 110.1 . . ? C7 C8 S2 125.9(12) . . ? C7 C8 H8A 105.9 . . ? S2 C8 H8A 105.9 . . ? C7 C8 H8B 105.9 . . ? S2 C8 H8B 105.9 . . ? H8A C8 H8B 106.2 . . ? C8 C7 S1 129.3(11) . . ? C8 C7 H7A 105.0 . . ? S1 C7 H7A 105.0 . . ? C8 C7 H7B 105.0 . . ? S1 C7 H7B 105.0 . . ? H7A C7 H7B 105.8 . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 28.54 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 1.154 _refine_diff_density_min -1.405 _refine_diff_density_rms 0.272 data_diedo3 _database_code_depnum_ccdc_archive 'CCDC 281972' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H8 Cl I4 O4 S8' _chemical_formula_weight 1063.75 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' 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' Cl Cl 0.1484 0.1585 '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' _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 7.5692(12) _cell_length_b 13.544(2) _cell_length_c 13.781(2) _cell_angle_alpha 91.385(4) _cell_angle_beta 101.128(3) _cell_angle_gamma 104.257(3) _cell_volume 1339.8(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293 _cell_measurement_reflns_used 5362 _cell_measurement_theta_min 2.84 _cell_measurement_theta_max 28.35 _exptl_crystal_description needle _exptl_crystal_colour black _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.637 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 986 _exptl_absorpt_coefficient_mu 5.400 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2334 _exptl_absorpt_correction_T_max 0.7740 _exptl_absorpt_process_details ; SADABS; Sheldrick 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293 _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 8.366 _diffrn_standards_number 165 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2.0 _diffrn_reflns_number 9927 _diffrn_reflns_av_R_equivalents 0.0160 _diffrn_reflns_av_sigmaI/netI 0.0316 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 28.38 _reflns_number_total 6512 _reflns_number_gt 6044 _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^)+(0.0494P)^2^+3.9402P] 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 6512 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0506 _refine_ls_R_factor_gt 0.0467 _refine_ls_wR_factor_ref 0.1150 _refine_ls_wR_factor_gt 0.1124 _refine_ls_goodness_of_fit_ref 1.166 _refine_ls_restrained_S_all 1.166 _refine_ls_shift/su_max 0.015 _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 I1 I 0.38563(6) 0.61870(3) 0.17955(3) 0.03774(11) Uani 1 1 d . . . I2 I 0.29920(6) 0.33095(3) 0.16696(3) 0.03822(11) Uani 1 1 d . . . I3 I 0.68261(8) 0.16472(4) 0.21212(3) 0.04678(13) Uani 1 1 d . . . I4 I 0.69067(6) -0.11218(3) 0.20886(3) 0.03481(11) Uani 1 1 d . . . Cl1 Cl 0.5420(3) 0.75498(13) 0.00854(12) 0.0467(4) Uani 1 1 d . . . S1 S 0.3113(2) 0.58614(12) 0.40180(11) 0.0367(3) Uani 1 1 d . . . S2 S 0.2303(3) 0.36323(13) 0.39086(12) 0.0418(4) Uani 1 1 d . . . S3 S 0.2489(2) 0.58856(13) 0.62595(11) 0.0386(3) Uani 1 1 d . . . S4 S 0.1620(3) 0.36307(14) 0.61323(13) 0.0500(4) Uani 1 1 d . . . S5 S 0.7335(3) 0.14493(13) 0.44817(11) 0.0429(4) Uani 1 1 d . . . S6 S 0.7401(2) -0.07032(12) 0.44827(11) 0.0386(3) Uani 1 1 d . . . S7 S 0.7772(3) 0.16310(12) 0.67912(11) 0.0379(3) Uani 1 1 d . . . S8 S 0.7780(2) -0.05460(13) 0.68940(11) 0.0388(3) Uani 1 1 d . . . O1 O 0.2039(8) 0.5863(4) 0.8114(3) 0.0498(12) Uani 1 1 d . . . O2 O 0.1158(9) 0.3678(4) 0.7987(4) 0.0575(14) Uani 1 1 d . . . O3 O 0.8298(7) 0.1831(4) 0.8734(3) 0.0414(10) Uani 1 1 d . . . O4 O 0.8184(7) -0.0304(4) 0.8848(3) 0.0428(11) Uani 1 1 d . . . C1 C 0.3152(8) 0.5243(5) 0.2897(4) 0.0324(12) Uani 1 1 d . . . C2 C 0.2775(8) 0.4229(5) 0.2854(4) 0.0305(12) Uani 1 1 d . . . C3 C 0.2521(8) 0.4753(5) 0.4618(4) 0.0329(12) Uani 1 1 d . . . C4 C 0.2239(8) 0.4751(5) 0.5559(4) 0.0355(13) Uani 1 1 d . . . C5 C 0.1968(9) 0.5264(5) 0.7302(4) 0.0366(13) Uani 1 1 d . . . C6 C 0.1571(10) 0.4251(6) 0.7235(5) 0.0431(15) Uani 1 1 d . . . C7 C 0.1369(13) 0.5312(7) 0.8877(5) 0.058(2) Uani 1 1 d . . . H1 H 0.0039 0.5243 0.8785 0.070 Uiso 1 1 calc R . . H2 H 0.1960 0.5697 0.9508 0.070 Uiso 1 1 calc R . . C8 C 0.1714(13) 0.4276(7) 0.8915(5) 0.059(2) Uani 1 1 d . . . H3 H 0.3033 0.4350 0.9162 0.071 Uiso 1 1 calc R . . H4 H 0.1053 0.3907 0.9387 0.071 Uiso 1 1 calc R . . C9 C 0.7225(9) 0.0814(5) 0.3351(4) 0.0329(12) Uani 1 1 d . . . C10 C 0.7261(8) -0.0159(5) 0.3350(4) 0.0314(12) Uani 1 1 d . . . C11 C 0.7480(9) 0.0404(5) 0.5173(4) 0.0352(13) Uani 1 1 d . . . C12 C 0.7662(9) 0.0472(5) 0.6171(4) 0.0332(12) Uani 1 1 d . . . C13 C 0.8045(8) 0.1154(5) 0.7950(4) 0.0329(12) Uani 1 1 d . . . C14 C 0.8038(8) 0.0180(5) 0.7998(4) 0.0322(12) Uani 1 1 d . . . C15 C 0.8811(11) 0.1380(6) 0.9659(5) 0.0476(17) Uani 1 1 d . . . H5 H 0.8547 0.1757 1.0199 0.057 Uiso 1 1 calc R . . H6 H 1.0137 0.1430 0.9794 0.057 Uiso 1 1 calc R . . C16 C 0.7770(10) 0.0294(6) 0.9610(5) 0.0428(15) Uani 1 1 d . . . H7 H 0.8094 0.0021 1.0246 0.051 Uiso 1 1 calc R . . H8 H 0.6444 0.0245 0.9478 0.051 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.0448(2) 0.0376(2) 0.0307(2) 0.00582(15) 0.00908(16) 0.00892(17) I2 0.0484(2) 0.0396(2) 0.02670(19) -0.00410(15) 0.00483(16) 0.01415(18) I3 0.0749(3) 0.0410(2) 0.0325(2) 0.01022(17) 0.0237(2) 0.0193(2) I4 0.0392(2) 0.0343(2) 0.0317(2) -0.00255(15) 0.01306(15) 0.00682(16) Cl1 0.0751(12) 0.0390(8) 0.0292(7) -0.0021(6) 0.0187(7) 0.0148(8) S1 0.0482(9) 0.0378(8) 0.0269(7) 0.0005(6) 0.0088(6) 0.0154(7) S2 0.0617(10) 0.0369(8) 0.0279(7) 0.0042(6) 0.0148(7) 0.0100(7) S3 0.0481(9) 0.0454(9) 0.0246(7) 0.0023(6) 0.0112(6) 0.0135(7) S4 0.0703(12) 0.0441(9) 0.0314(8) -0.0017(7) 0.0196(8) 0.0005(8) S5 0.0701(11) 0.0346(8) 0.0257(7) 0.0011(6) 0.0121(7) 0.0150(8) S6 0.0538(9) 0.0354(8) 0.0281(7) 0.0028(6) 0.0078(6) 0.0147(7) S7 0.0557(9) 0.0364(8) 0.0239(7) 0.0058(6) 0.0110(6) 0.0132(7) S8 0.0512(9) 0.0380(8) 0.0290(7) 0.0038(6) 0.0078(6) 0.0152(7) O1 0.060(3) 0.063(3) 0.026(2) -0.006(2) 0.014(2) 0.011(3) O2 0.079(4) 0.057(3) 0.033(3) 0.005(2) 0.025(3) -0.002(3) O3 0.055(3) 0.044(3) 0.027(2) 0.0004(18) 0.0086(19) 0.016(2) O4 0.059(3) 0.046(3) 0.028(2) 0.0126(19) 0.010(2) 0.019(2) C1 0.039(3) 0.042(3) 0.019(2) 0.000(2) 0.006(2) 0.016(3) C2 0.032(3) 0.041(3) 0.020(2) -0.003(2) 0.003(2) 0.013(2) C3 0.034(3) 0.043(3) 0.024(3) 0.003(2) 0.007(2) 0.013(2) C4 0.031(3) 0.050(4) 0.023(3) -0.004(2) 0.004(2) 0.008(3) C5 0.040(3) 0.047(4) 0.022(3) -0.001(2) 0.010(2) 0.007(3) C6 0.048(4) 0.056(4) 0.026(3) 0.002(3) 0.016(3) 0.006(3) C7 0.065(5) 0.070(5) 0.034(4) -0.003(3) 0.016(3) 0.003(4) C8 0.078(6) 0.089(6) 0.028(3) 0.014(4) 0.019(3) 0.047(5) C9 0.038(3) 0.040(3) 0.023(3) 0.000(2) 0.011(2) 0.010(2) C10 0.034(3) 0.038(3) 0.022(3) -0.001(2) 0.011(2) 0.005(2) C11 0.041(3) 0.040(3) 0.025(3) 0.001(2) 0.007(2) 0.011(3) C12 0.037(3) 0.036(3) 0.027(3) 0.003(2) 0.006(2) 0.011(2) C13 0.036(3) 0.044(3) 0.020(3) 0.002(2) 0.006(2) 0.013(3) C14 0.032(3) 0.040(3) 0.026(3) 0.007(2) 0.009(2) 0.011(2) C15 0.060(4) 0.059(4) 0.023(3) 0.002(3) 0.007(3) 0.017(4) C16 0.051(4) 0.056(4) 0.026(3) 0.015(3) 0.010(3) 0.019(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 I1 C1 2.073(6) . ? I2 C2 2.085(5) . ? I3 C9 2.073(6) . ? I4 C10 2.081(6) . ? S1 C3 1.735(6) . ? S1 C1 1.748(6) . ? S2 C2 1.734(6) . ? S2 C3 1.740(6) . ? S3 C5 1.744(6) . ? S3 C4 1.745(7) . ? S4 C4 1.731(7) . ? S4 C6 1.730(7) . ? S5 C9 1.739(6) . ? S5 C11 1.739(6) . ? S6 C11 1.738(6) . ? S6 C10 1.739(6) . ? S7 C13 1.732(6) . ? S7 C12 1.745(6) . ? S8 C12 1.730(6) . ? S8 C14 1.743(6) . ? O1 C5 1.350(7) . ? O1 C7 1.406(9) . ? O2 C6 1.348(8) . ? O2 C8 1.430(9) . ? O3 C13 1.353(7) . ? O3 C15 1.454(8) . ? O4 C14 1.355(7) . ? O4 C16 1.438(8) . ? C1 C2 1.330(9) . ? C3 C4 1.355(8) . ? C5 C6 1.327(10) . ? C7 C8 1.489(12) . ? C7 H1 0.9700 . ? C7 H2 0.9700 . ? C8 H3 0.9700 . ? C8 H4 0.9700 . ? C9 C10 1.325(9) . ? C11 C12 1.355(8) . ? C13 C14 1.320(9) . ? C15 C16 1.481(10) . ? C15 H5 0.9700 . ? C15 H6 0.9700 . ? C16 H7 0.9700 . ? C16 H8 0.9700 . ? 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 C3 S1 C1 95.5(3) . . ? C2 S2 C3 95.5(3) . . ? C5 S3 C4 93.7(3) . . ? C4 S4 C6 94.0(3) . . ? C9 S5 C11 95.1(3) . . ? C11 S6 C10 95.3(3) . . ? C13 S7 C12 93.7(3) . . ? C12 S8 C14 93.5(3) . . ? C5 O1 C7 113.4(6) . . ? C6 O2 C8 111.4(6) . . ? C13 O3 C15 110.6(5) . . ? C14 O4 C16 109.0(5) . . ? C2 C1 S1 116.8(5) . . ? C2 C1 I1 127.4(4) . . ? S1 C1 I1 115.8(3) . . ? C1 C2 S2 117.6(4) . . ? C1 C2 I2 124.9(4) . . ? S2 C2 I2 117.1(3) . . ? C4 C3 S1 123.2(5) . . ? C4 C3 S2 122.3(5) . . ? S1 C3 S2 114.5(3) . . ? C3 C4 S4 122.1(5) . . ? C3 C4 S3 121.5(5) . . ? S4 C4 S3 116.5(3) . . ? C6 C5 O1 125.8(6) . . ? C6 C5 S3 117.5(5) . . ? O1 C5 S3 116.7(5) . . ? C5 C6 O2 123.5(6) . . ? C5 C6 S4 118.4(5) . . ? O2 C6 S4 118.1(6) . . ? O1 C7 C8 113.4(7) . . ? O1 C7 H1 108.9 . . ? C8 C7 H1 108.9 . . ? O1 C7 H2 108.9 . . ? C8 C7 H2 108.9 . . ? H1 C7 H2 107.7 . . ? O2 C8 C7 114.8(6) . . ? O2 C8 H3 108.6 . . ? C7 C8 H3 108.6 . . ? O2 C8 H4 108.6 . . ? C7 C8 H4 108.6 . . ? H3 C8 H4 107.6 . . ? C10 C9 S5 117.7(5) . . ? C10 C9 I3 126.7(4) . . ? S5 C9 I3 115.4(3) . . ? C9 C10 S6 117.2(4) . . ? C9 C10 I4 125.2(4) . . ? S6 C10 I4 117.3(3) . . ? C12 C11 S6 123.8(5) . . ? C12 C11 S5 121.5(5) . . ? S6 C11 S5 114.7(3) . . ? C11 C12 S8 123.5(5) . . ? C11 C12 S7 119.9(5) . . ? S8 C12 S7 116.6(3) . . ? C14 C13 O3 125.8(5) . . ? C14 C13 S7 118.0(5) . . ? O3 C13 S7 116.2(5) . . ? C13 C14 O4 124.5(6) . . ? C13 C14 S8 118.2(4) . . ? O4 C14 S8 117.3(5) . . ? O3 C15 C16 111.0(6) . . ? O3 C15 H5 109.4 . . ? C16 C15 H5 109.4 . . ? O3 C15 H6 109.4 . . ? C16 C15 H6 109.4 . . ? H5 C15 H6 108.0 . . ? O4 C16 C15 111.4(6) . . ? O4 C16 H7 109.3 . . ? C15 C16 H7 109.3 . . ? O4 C16 H8 109.3 . . ? C15 C16 H8 109.3 . . ? H7 C16 H8 108.0 . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 28.38 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 2.190 _refine_diff_density_min -0.818 _refine_diff_density_rms 0.171 data_diedo1 _database_code_depnum_ccdc_archive 'CCDC 281973' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H8 Br I4 O4 S8' _chemical_formula_weight 1108.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' Br Br -0.2901 2.4595 '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' _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 7.6511(16) _cell_length_b 13.700(3) _cell_length_c 14.006(3) _cell_angle_alpha 90.804(5) _cell_angle_beta 101.885(4) _cell_angle_gamma 104.209(4) _cell_volume 1389.5(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293 _cell_measurement_reflns_used 4128 _cell_measurement_theta_min 2.81 _cell_measurement_theta_max 28.27 _exptl_crystal_description block _exptl_crystal_colour black _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.649 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1022 _exptl_absorpt_coefficient_mu 6.548 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.3853 _exptl_absorpt_correction_T_max 0.6224 _exptl_absorpt_process_details ; SADABS; Sheldrick 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293 _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 8.366 _diffrn_standards_number 126 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2.0 _diffrn_reflns_number 10317 _diffrn_reflns_av_R_equivalents 0.0194 _diffrn_reflns_av_sigmaI/netI 0.0405 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 28.33 _reflns_number_total 6782 _reflns_number_gt 5788 _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^)+(0.0623P)^2^+0.8005P] 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 6782 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0547 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1166 _refine_ls_wR_factor_gt 0.1110 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _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 I1 I 0.38640(6) 0.61847(3) 0.18272(3) 0.03659(11) Uani 1 1 d . . . I2 I 0.29286(6) 0.33207(3) 0.17191(3) 0.03804(12) Uani 1 1 d . . . I3 I 0.68506(7) 0.16400(3) 0.21647(3) 0.04471(13) Uani 1 1 d . . . I4 I 0.69655(6) -0.11065(3) 0.21731(3) 0.03506(11) Uani 1 1 d . . . Br1 Br 0.54368(11) 0.75641(5) 0.00755(5) 0.04240(17) Uani 1 1 d . . . S1 S 0.3136(2) 0.58698(12) 0.40371(11) 0.0360(3) Uani 1 1 d . . . S2 S 0.2241(3) 0.36482(12) 0.39330(12) 0.0407(4) Uani 1 1 d . . . S3 S 0.2510(2) 0.58961(13) 0.62610(12) 0.0378(3) Uani 1 1 d . . . S4 S 0.1548(3) 0.36481(14) 0.61277(13) 0.0466(4) Uani 1 1 d . . . S5 S 0.7338(3) 0.14490(12) 0.45177(12) 0.0425(4) Uani 1 1 d . . . S6 S 0.7418(2) -0.06901(12) 0.45464(12) 0.0376(3) Uani 1 1 d . . . S7 S 0.7767(2) 0.16360(12) 0.68141(11) 0.0374(4) Uani 1 1 d . . . S8 S 0.7769(2) -0.05335(12) 0.69346(12) 0.0370(3) Uani 1 1 d . . . O1 O 0.2066(7) 0.5863(4) 0.8097(3) 0.0455(11) Uani 1 1 d . . . O2 O 0.1134(8) 0.3686(4) 0.7976(4) 0.0548(14) Uani 1 1 d . . . O3 O 0.8290(6) 0.1831(3) 0.8744(3) 0.0378(10) Uani 1 1 d . . . O4 O 0.8166(7) -0.0302(4) 0.8876(3) 0.0416(11) Uani 1 1 d . . . C1 C 0.3138(8) 0.5245(5) 0.2934(4) 0.0314(12) Uani 1 1 d . . . C2 C 0.2746(8) 0.4244(5) 0.2889(4) 0.0306(12) Uani 1 1 d . . . C3 C 0.2510(8) 0.4768(5) 0.4638(4) 0.0314(12) Uani 1 1 d . . . C4 C 0.2220(9) 0.4777(5) 0.5562(4) 0.0339(13) Uani 1 1 d . . . C5 C 0.1993(9) 0.5283(5) 0.7299(4) 0.0365(14) Uani 1 1 d . . . C6 C 0.1551(9) 0.4268(5) 0.7235(4) 0.0380(14) Uani 1 1 d . . . C7 C 0.1370(12) 0.5306(6) 0.8849(5) 0.0542(19) Uani 1 1 d . . . H1 H 0.0051 0.5238 0.8740 0.065 Uiso 1 1 calc R . . H2 H 0.1942 0.5681 0.9474 0.065 Uiso 1 1 calc R . . C8 C 0.1716(13) 0.4282(6) 0.8892(5) 0.057(2) Uani 1 1 d . . . H3 H 0.3028 0.4355 0.9131 0.069 Uiso 1 1 calc R . . H4 H 0.1082 0.3918 0.9363 0.069 Uiso 1 1 calc R . . C9 C 0.7242(8) 0.0822(5) 0.3396(4) 0.0325(13) Uani 1 1 d . . . C10 C 0.7298(8) -0.0147(4) 0.3410(4) 0.0302(12) Uani 1 1 d . . . C11 C 0.7501(9) 0.0414(5) 0.5221(4) 0.0334(13) Uani 1 1 d . . . C12 C 0.7657(8) 0.0482(4) 0.6205(4) 0.0313(12) Uani 1 1 d . . . C13 C 0.8034(8) 0.1161(5) 0.7971(4) 0.0316(12) Uani 1 1 d . . . C14 C 0.8023(8) 0.0173(5) 0.8024(4) 0.0303(12) Uani 1 1 d . . . C15 C 0.8826(10) 0.1388(5) 0.9667(5) 0.0415(15) Uani 1 1 d . . . H5 H 0.8601 0.1769 1.0198 0.050 Uiso 1 1 calc R . . H6 H 1.0135 0.1421 0.9793 0.050 Uiso 1 1 calc R . . C16 C 0.7730(10) 0.0296(5) 0.9624(5) 0.0427(16) Uani 1 1 d . . . H7 H 0.8026 0.0024 1.0255 0.051 Uiso 1 1 calc R . . H8 H 0.6419 0.0261 0.9473 0.051 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.0438(2) 0.0363(2) 0.0302(2) 0.00600(16) 0.01092(17) 0.00852(17) I2 0.0496(3) 0.0394(2) 0.0266(2) -0.00331(16) 0.00700(17) 0.01551(18) I3 0.0725(3) 0.0395(2) 0.0294(2) 0.00995(17) 0.0220(2) 0.0183(2) I4 0.0410(2) 0.0345(2) 0.0308(2) -0.00379(16) 0.01351(17) 0.00731(16) Br1 0.0649(4) 0.0375(3) 0.0279(3) 0.0000(3) 0.0165(3) 0.0135(3) S1 0.0483(9) 0.0359(8) 0.0266(8) 0.0012(6) 0.0100(7) 0.0143(7) S2 0.0619(11) 0.0348(8) 0.0282(8) 0.0037(6) 0.0166(7) 0.0117(7) S3 0.0481(9) 0.0424(9) 0.0245(7) 0.0027(6) 0.0106(7) 0.0119(7) S4 0.0686(12) 0.0402(9) 0.0295(8) -0.0021(7) 0.0203(8) 0.0030(8) S5 0.0747(12) 0.0324(8) 0.0238(8) 0.0015(6) 0.0138(8) 0.0173(8) S6 0.0542(10) 0.0337(8) 0.0274(8) 0.0024(6) 0.0093(7) 0.0151(7) S7 0.0579(10) 0.0351(8) 0.0232(7) 0.0060(6) 0.0119(7) 0.0162(7) S8 0.0493(9) 0.0343(8) 0.0297(8) 0.0048(6) 0.0103(7) 0.0135(7) O1 0.058(3) 0.052(3) 0.025(2) -0.009(2) 0.014(2) 0.007(2) O2 0.083(4) 0.044(3) 0.035(3) 0.008(2) 0.027(3) -0.001(3) O3 0.051(3) 0.041(2) 0.024(2) 0.0045(18) 0.0104(19) 0.015(2) O4 0.056(3) 0.047(3) 0.024(2) 0.0098(19) 0.008(2) 0.018(2) C1 0.033(3) 0.038(3) 0.026(3) 0.005(2) 0.008(2) 0.014(2) C2 0.032(3) 0.036(3) 0.025(3) 0.000(2) 0.006(2) 0.012(2) C3 0.032(3) 0.040(3) 0.023(3) 0.000(2) 0.005(2) 0.011(2) C4 0.039(3) 0.038(3) 0.025(3) 0.000(2) 0.007(2) 0.009(3) C5 0.038(3) 0.045(4) 0.025(3) -0.001(3) 0.007(3) 0.007(3) C6 0.046(4) 0.045(4) 0.022(3) 0.002(3) 0.011(3) 0.007(3) C7 0.067(5) 0.064(5) 0.031(4) 0.004(3) 0.020(4) 0.009(4) C8 0.086(6) 0.077(6) 0.025(4) 0.013(4) 0.021(4) 0.042(5) C9 0.037(3) 0.037(3) 0.021(3) 0.003(2) 0.007(2) 0.006(3) C10 0.039(3) 0.033(3) 0.020(3) 0.000(2) 0.008(2) 0.010(2) C11 0.045(3) 0.034(3) 0.025(3) 0.004(2) 0.010(3) 0.014(3) C12 0.040(3) 0.030(3) 0.025(3) 0.003(2) 0.008(2) 0.011(2) C13 0.035(3) 0.040(3) 0.024(3) 0.003(2) 0.012(2) 0.014(3) C14 0.033(3) 0.038(3) 0.024(3) 0.009(2) 0.009(2) 0.015(2) C15 0.050(4) 0.049(4) 0.024(3) -0.001(3) 0.005(3) 0.013(3) C16 0.051(4) 0.056(4) 0.023(3) 0.014(3) 0.011(3) 0.015(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 I1 C1 2.104(6) . ? I2 C2 2.104(6) . ? I3 C9 2.080(6) . ? I4 C10 2.094(6) . ? S1 C3 1.750(6) . ? S1 C1 1.756(6) . ? S2 C2 1.751(6) . ? S2 C3 1.758(6) . ? S3 C4 1.750(6) . ? S3 C5 1.755(6) . ? S4 C6 1.757(6) . ? S4 C4 1.759(6) . ? S5 C11 1.752(6) . ? S5 C9 1.759(6) . ? S6 C11 1.753(6) . ? S6 C10 1.762(6) . ? S7 C13 1.746(6) . ? S7 C12 1.762(6) . ? S8 C12 1.746(6) . ? S8 C14 1.746(6) . ? O1 C5 1.346(7) . ? O1 C7 1.424(8) . ? O2 C6 1.361(7) . ? O2 C8 1.437(9) . ? O3 C13 1.360(7) . ? O3 C15 1.461(7) . ? O4 C14 1.364(7) . ? O4 C16 1.461(8) . ? C1 C2 1.328(8) . ? C3 C4 1.358(8) . ? C5 C6 1.346(9) . ? C7 C8 1.491(11) . ? C7 H1 0.9700 . ? C7 H2 0.9700 . ? C8 H3 0.9700 . ? C8 H4 0.9700 . ? C9 C10 1.339(8) . ? C11 C12 1.359(8) . ? C13 C14 1.355(8) . ? C15 C16 1.518(10) . ? C15 H5 0.9700 . ? C15 H6 0.9700 . ? C16 H7 0.9700 . ? C16 H8 0.9700 . ? 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 C3 S1 C1 95.3(3) . . ? C2 S2 C3 95.5(3) . . ? C4 S3 C5 94.4(3) . . ? C6 S4 C4 93.9(3) . . ? C11 S5 C9 95.6(3) . . ? C11 S6 C10 95.5(3) . . ? C13 S7 C12 93.9(3) . . ? C12 S8 C14 94.2(3) . . ? C5 O1 C7 113.6(5) . . ? C6 O2 C8 110.4(5) . . ? C13 O3 C15 110.9(5) . . ? C14 O4 C16 109.3(5) . . ? C2 C1 S1 117.7(5) . . ? C2 C1 I1 126.7(5) . . ? S1 C1 I1 115.6(3) . . ? C1 C2 S2 117.3(5) . . ? C1 C2 I2 125.4(4) . . ? S2 C2 I2 117.1(3) . . ? C4 C3 S1 122.9(5) . . ? C4 C3 S2 122.8(5) . . ? S1 C3 S2 114.3(3) . . ? C3 C4 S3 122.5(5) . . ? C3 C4 S4 121.3(5) . . ? S3 C4 S4 116.2(3) . . ? O1 C5 C6 124.9(6) . . ? O1 C5 S3 117.7(5) . . ? C6 C5 S3 117.4(5) . . ? C5 C6 O2 124.4(6) . . ? C5 C6 S4 118.0(5) . . ? O2 C6 S4 117.6(5) . . ? O1 C7 C8 113.0(6) . . ? O1 C7 H1 109.0 . . ? C8 C7 H1 109.0 . . ? O1 C7 H2 109.0 . . ? C8 C7 H2 109.0 . . ? H1 C7 H2 107.8 . . ? O2 C8 C7 114.8(6) . . ? O2 C8 H3 108.6 . . ? C7 C8 H3 108.6 . . ? O2 C8 H4 108.6 . . ? C7 C8 H4 108.6 . . ? H3 C8 H4 107.5 . . ? C10 C9 S5 117.2(4) . . ? C10 C9 I3 126.6(4) . . ? S5 C9 I3 116.0(3) . . ? C9 C10 S6 117.1(4) . . ? C9 C10 I4 125.2(4) . . ? S6 C10 I4 117.3(3) . . ? C12 C11 S5 121.6(5) . . ? C12 C11 S6 124.0(5) . . ? S5 C11 S6 114.4(3) . . ? C11 C12 S8 123.4(5) . . ? C11 C12 S7 120.3(5) . . ? S8 C12 S7 116.3(3) . . ? C14 C13 O3 125.8(5) . . ? C14 C13 S7 117.7(5) . . ? O3 C13 S7 116.5(4) . . ? C13 C14 O4 123.8(6) . . ? C13 C14 S8 117.8(4) . . ? O4 C14 S8 118.4(4) . . ? O3 C15 C16 110.2(5) . . ? O3 C15 H5 109.6 . . ? C16 C15 H5 109.6 . . ? O3 C15 H6 109.6 . . ? C16 C15 H6 109.6 . . ? H5 C15 H6 108.1 . . ? O4 C16 C15 110.1(5) . . ? O4 C16 H7 109.6 . . ? C15 C16 H7 109.6 . . ? O4 C16 H8 109.6 . . ? C15 C16 H8 109.6 . . ? H7 C16 H8 108.1 . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 1.643 _refine_diff_density_min -0.664 _refine_diff_density_rms 0.179 data_diedost_1 _database_code_depnum_ccdc_archive 'CCDC 281974' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H8 Cl I4 O4 S4 Se4' _chemical_formula_weight 1251.35 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' 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6396(19) _cell_length_b 13.416(3) _cell_length_c 14.049(3) _cell_angle_alpha 91.468(6) _cell_angle_beta 100.217(5) _cell_angle_gamma 105.839(6) _cell_volume 1359.1(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293 _cell_measurement_reflns_used 2299 _cell_measurement_theta_min 2.82 _cell_measurement_theta_max 27.98 _exptl_crystal_description block _exptl_crystal_colour black _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.058 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1130 _exptl_absorpt_coefficient_mu 10.372 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.1813 _exptl_absorpt_correction_T_max 0.6251 _exptl_absorpt_process_details ; SADABS; Sheldrick 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293 _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 8.366 _diffrn_standards_number 80 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2.0 _diffrn_reflns_number 10164 _diffrn_reflns_av_R_equivalents 0.0489 _diffrn_reflns_av_sigmaI/netI 0.0952 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 28.47 _reflns_number_total 6676 _reflns_number_gt 4545 _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^)+(0.0772P)^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_number_reflns 6676 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0908 _refine_ls_R_factor_gt 0.0658 _refine_ls_wR_factor_ref 0.1699 _refine_ls_wR_factor_gt 0.1573 _refine_ls_goodness_of_fit_ref 0.967 _refine_ls_restrained_S_all 0.967 _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 I1 I 0.36836(10) 0.61338(6) 0.17842(5) 0.0377(2) Uani 1 1 d . . . I2 I 0.30134(10) 0.32448(6) 0.16708(5) 0.0383(2) Uani 1 1 d . . . I3 I 0.69612(13) 0.16927(6) 0.21324(6) 0.0458(2) Uani 1 1 d . . . I4 I 0.68769(10) -0.11107(5) 0.20624(5) 0.03472(19) Uani 1 1 d . . . Cl1 Cl 0.5353(4) 0.7559(2) 0.0081(2) 0.0443(7) Uani 1 1 d . . . Se1 Se 0.29535(16) 0.58682(9) 0.40522(8) 0.0357(3) Uani 1 1 d . . . Se2 Se 0.23559(17) 0.34376(9) 0.39644(8) 0.0393(3) Uani 1 1 d . . . S1 S 0.2403(4) 0.5784(2) 0.6322(2) 0.0396(7) Uani 1 1 d . . . S2 S 0.1884(4) 0.3519(2) 0.6256(2) 0.0415(7) Uani 1 1 d . . . Se3 Se 0.74078(17) 0.15661(9) 0.45246(8) 0.0380(3) Uani 1 1 d . . . Se4 Se 0.73458(16) -0.08034(9) 0.44902(8) 0.0368(3) Uani 1 1 d . . . S3 S 0.7800(4) 0.1636(2) 0.6846(2) 0.0365(6) Uani 1 1 d . . . S4 S 0.7741(4) -0.0575(2) 0.6916(2) 0.0373(6) Uani 1 1 d . . . O1 O 0.1982(14) 0.5751(7) 0.8141(6) 0.060(3) Uani 1 1 d . . . O2 O 0.1475(13) 0.3555(7) 0.8066(6) 0.055(2) Uani 1 1 d . . . O3 O 0.8294(11) 0.1817(6) 0.8743(5) 0.0409(19) Uani 1 1 d . . . O4 O 0.8147(11) -0.0345(6) 0.8828(5) 0.0405(19) Uani 1 1 d . . . C1 C 0.2984(14) 0.5156(8) 0.2900(7) 0.030(2) Uani 1 1 d . . . C2 C 0.2771(13) 0.4146(8) 0.2842(7) 0.029(2) Uani 1 1 d . . . C3 C 0.2471(14) 0.4629(8) 0.4713(8) 0.033(2) Uani 1 1 d . . . C4 C 0.2283(13) 0.4637(9) 0.5651(7) 0.033(2) Uani 1 1 d . . . C5 C 0.1970(14) 0.5150(10) 0.7356(8) 0.038(3) Uani 1 1 d . . . C6 C 0.1761(15) 0.4153(9) 0.7327(8) 0.037(3) Uani 1 1 d . . . C7 C 0.183(4) 0.5196(13) 0.8917(11) 0.145(12) Uani 1 1 d . . . H7A H 0.0695 0.5248 0.9111 0.174 Uiso 1 1 calc R . . H7B H 0.2835 0.5577 0.9429 0.174 Uiso 1 1 calc R . . C8 C 0.180(3) 0.4174(15) 0.8966(9) 0.080(6) Uani 1 1 d . . . H8A H 0.0844 0.3846 0.9323 0.096 Uiso 1 1 calc R . . H8B H 0.2975 0.4149 0.9344 0.096 Uiso 1 1 calc R . . C9 C 0.7295(14) 0.0846(8) 0.3330(7) 0.031(2) Uani 1 1 d . . . C10 C 0.7258(13) -0.0143(8) 0.3320(7) 0.029(2) Uani 1 1 d . . . C11 C 0.7486(14) 0.0410(8) 0.5250(8) 0.031(2) Uani 1 1 d . . . C12 C 0.7681(14) 0.0483(8) 0.6219(8) 0.033(2) Uani 1 1 d . . . C13 C 0.8041(13) 0.1149(9) 0.7978(7) 0.032(2) Uani 1 1 d . . . C14 C 0.8006(13) 0.0158(8) 0.8012(7) 0.031(2) Uani 1 1 d . . . C15 C 0.882(2) 0.1348(9) 0.9625(8) 0.051(3) Uani 1 1 d . . . H15A H 0.8622 0.1731 1.0171 0.061 Uiso 1 1 calc R . . H15B H 1.0131 0.1399 0.9719 0.061 Uiso 1 1 calc R . . C16 C 0.7765(18) 0.0251(9) 0.9605(8) 0.047(3) Uani 1 1 d . . . H16A H 0.8114 -0.0020 1.0222 0.057 Uiso 1 1 calc R . . H16B H 0.6449 0.0190 0.9503 0.057 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.0466(4) 0.0373(4) 0.0283(4) 0.0072(3) 0.0029(3) 0.0125(3) I2 0.0518(4) 0.0374(4) 0.0243(4) -0.0041(3) 0.0023(3) 0.0142(3) I3 0.0750(6) 0.0402(5) 0.0287(4) 0.0096(3) 0.0185(4) 0.0209(4) I4 0.0427(4) 0.0324(4) 0.0289(4) -0.0039(3) 0.0099(3) 0.0090(3) Cl1 0.0723(19) 0.0360(16) 0.0270(15) -0.0028(11) 0.0135(13) 0.0170(14) Se1 0.0519(7) 0.0335(6) 0.0251(6) 0.0008(4) 0.0048(5) 0.0193(5) Se2 0.0600(7) 0.0318(6) 0.0280(6) 0.0031(5) 0.0122(5) 0.0138(5) S1 0.0563(17) 0.0414(17) 0.0250(15) 0.0007(12) 0.0068(12) 0.0212(14) S2 0.0554(18) 0.0371(16) 0.0285(16) 0.0004(12) 0.0088(13) 0.0068(13) Se3 0.0640(7) 0.0307(6) 0.0211(6) 0.0011(4) 0.0084(5) 0.0162(5) Se4 0.0542(7) 0.0333(6) 0.0254(6) 0.0010(4) 0.0051(5) 0.0180(5) S3 0.0567(17) 0.0309(15) 0.0220(14) 0.0024(11) 0.0068(12) 0.0129(12) S4 0.0510(16) 0.0308(15) 0.0302(16) 0.0022(11) 0.0035(12) 0.0145(12) O1 0.098(7) 0.069(6) 0.017(5) -0.012(4) 0.004(4) 0.037(6) O2 0.073(6) 0.061(6) 0.026(5) 0.010(4) 0.015(4) 0.007(5) O3 0.066(5) 0.036(5) 0.024(4) 0.000(3) 0.002(4) 0.023(4) O4 0.064(5) 0.040(5) 0.023(4) 0.013(3) 0.004(4) 0.025(4) C1 0.035(5) 0.032(6) 0.024(6) 0.012(4) 0.002(4) 0.013(4) C2 0.034(5) 0.032(6) 0.020(5) -0.005(4) 0.004(4) 0.008(4) C3 0.032(5) 0.038(6) 0.029(6) -0.004(5) -0.002(4) 0.013(5) C4 0.029(5) 0.054(7) 0.018(5) -0.001(5) -0.002(4) 0.020(5) C5 0.031(5) 0.064(8) 0.018(6) 0.001(5) 0.005(4) 0.014(5) C6 0.039(6) 0.044(7) 0.022(6) 0.002(5) 0.004(4) 0.003(5) C7 0.28(3) 0.063(12) 0.031(10) -0.025(8) 0.039(13) -0.066(15) C8 0.116(13) 0.146(17) 0.013(7) 0.019(8) 0.017(7) 0.093(13) C9 0.036(5) 0.040(6) 0.019(5) 0.010(4) 0.008(4) 0.012(5) C10 0.026(5) 0.032(6) 0.026(6) -0.004(4) -0.002(4) 0.008(4) C11 0.036(5) 0.034(6) 0.026(6) 0.004(4) 0.010(4) 0.010(4) C12 0.031(5) 0.033(6) 0.029(6) -0.007(4) -0.003(4) 0.005(4) C13 0.024(5) 0.056(7) 0.015(5) 0.008(5) 0.004(4) 0.008(5) C14 0.030(5) 0.038(6) 0.025(6) 0.007(4) 0.009(4) 0.008(4) C15 0.087(10) 0.047(8) 0.021(6) 0.004(5) 0.004(6) 0.027(7) C16 0.064(8) 0.046(8) 0.026(7) 0.011(5) 0.009(5) 0.005(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C1 2.118(11) . ? I2 C2 2.082(9) . ? I3 C9 2.072(10) . ? I4 C10 2.094(9) . ? Se1 C1 1.865(10) . ? Se1 C3 1.905(12) . ? Se2 C3 1.864(10) . ? Se2 C2 1.892(11) . ? S1 C5 1.740(12) . ? S1 C4 1.756(10) . ? S2 C4 1.724(12) . ? S2 C6 1.740(11) . ? Se3 C11 1.886(11) . ? Se3 C9 1.892(10) . ? Se4 C10 1.887(11) . ? Se4 C11 1.891(10) . ? S3 C12 1.733(10) . ? S3 C13 1.734(11) . ? S4 C12 1.752(12) . ? S4 C14 1.755(10) . ? O1 C7 1.340(19) . ? O1 C5 1.346(12) . ? O2 C6 1.340(14) . ? O2 C8 1.439(15) . ? O3 C13 1.334(12) . ? O3 C15 1.447(14) . ? O4 C14 1.348(13) . ? O4 C16 1.453(13) . ? C1 C2 1.318(14) . ? C3 C4 1.351(15) . ? C5 C6 1.301(16) . ? C7 C8 1.37(2) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.319(14) . ? C11 C12 1.340(14) . ? C13 C14 1.324(15) . ? C15 C16 1.469(17) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? 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 C1 Se1 C3 92.6(4) . . ? C3 Se2 C2 94.4(5) . . ? C5 S1 C4 93.4(6) . . ? C4 S2 C6 93.8(5) . . ? C11 Se3 C9 93.9(4) . . ? C10 Se4 C11 93.7(4) . . ? C12 S3 C13 94.6(6) . . ? C12 S4 C14 93.2(5) . . ? C7 O1 C5 111.1(12) . . ? C6 O2 C8 111.5(11) . . ? C13 O3 C15 109.6(8) . . ? C14 O4 C16 109.0(8) . . ? C2 C1 Se1 121.5(8) . . ? C2 C1 I1 124.2(8) . . ? Se1 C1 I1 114.0(5) . . ? C1 C2 Se2 117.3(8) . . ? C1 C2 I2 127.1(8) . . ? Se2 C2 I2 115.5(5) . . ? C4 C3 Se2 123.9(9) . . ? C4 C3 Se1 121.9(8) . . ? Se2 C3 Se1 114.1(6) . . ? C3 C4 S2 121.9(8) . . ? C3 C4 S1 121.9(9) . . ? S2 C4 S1 116.1(6) . . ? C6 C5 O1 125.5(12) . . ? C6 C5 S1 117.9(9) . . ? O1 C5 S1 116.5(10) . . ? C5 C6 O2 125.5(11) . . ? C5 C6 S2 118.7(9) . . ? O2 C6 S2 115.8(9) . . ? O1 C7 C8 126.6(14) . . ? O1 C7 H7A 105.7 . . ? C8 C7 H7A 105.7 . . ? O1 C7 H7B 105.7 . . ? C8 C7 H7B 105.7 . . ? H7A C7 H7B 106.1 . . ? C7 C8 O2 117.6(12) . . ? C7 C8 H8A 107.9 . . ? O2 C8 H8A 107.9 . . ? C7 C8 H8B 107.9 . . ? O2 C8 H8B 107.9 . . ? H8A C8 H8B 107.2 . . ? C10 C9 Se3 118.8(8) . . ? C10 C9 I3 126.5(8) . . ? Se3 C9 I3 114.3(5) . . ? C9 C10 Se4 119.7(8) . . ? C9 C10 I4 124.6(8) . . ? Se4 C10 I4 115.5(5) . . ? C12 C11 Se3 121.3(8) . . ? C12 C11 Se4 124.8(8) . . ? Se3 C11 Se4 113.9(5) . . ? C11 C12 S3 121.1(9) . . ? C11 C12 S4 122.6(8) . . ? S3 C12 S4 116.3(6) . . ? C14 C13 O3 125.7(10) . . ? C14 C13 S3 117.6(8) . . ? O3 C13 S3 116.7(8) . . ? C13 C14 O4 125.1(9) . . ? C13 C14 S4 118.3(8) . . ? O4 C14 S4 116.6(8) . . ? O3 C15 C16 112.6(10) . . ? O3 C15 H15A 109.1 . . ? C16 C15 H15A 109.1 . . ? O3 C15 H15B 109.1 . . ? C16 C15 H15B 109.1 . . ? H15A C15 H15B 107.8 . . ? O4 C16 C15 109.6(10) . . ? O4 C16 H16A 109.8 . . ? C15 C16 H16A 109.8 . . ? O4 C16 H16B 109.8 . . ? C15 C16 H16B 109.8 . . ? H16A C16 H16B 108.2 . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 28.47 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 2.129 _refine_diff_density_min -1.405 _refine_diff_density_rms 0.331 data_diedost_2 _database_code_depnum_ccdc_archive 'CCDC 281975' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H8 Br I4 O4 S4 Se4' _chemical_formula_weight 1295.81 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' 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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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' _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 7.709(2) _cell_length_b 13.546(4) _cell_length_c 14.219(4) _cell_angle_alpha 90.866(7) _cell_angle_beta 100.943(6) _cell_angle_gamma 105.857(6) _cell_volume 1398.9(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293 _cell_measurement_reflns_used 1641 _cell_measurement_theta_min 2.80 _cell_measurement_theta_max 25.95 _exptl_crystal_description plate _exptl_crystal_colour black _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.076 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1166 _exptl_absorpt_coefficient_mu 11.410 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2087 _exptl_absorpt_correction_T_max 0.5993 _exptl_absorpt_process_details ; SADABS; Sheldrick 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293 _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 8.366 _diffrn_standards_number 66 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2.0 _diffrn_reflns_number 10515 _diffrn_reflns_av_R_equivalents 0.0515 _diffrn_reflns_av_sigmaI/netI 0.1132 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 28.57 _reflns_number_total 6878 _reflns_number_gt 4360 _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^)+(0.0586P)^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_number_reflns 6878 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1163 _refine_ls_R_factor_gt 0.0736 _refine_ls_wR_factor_ref 0.1638 _refine_ls_wR_factor_gt 0.1441 _refine_ls_goodness_of_fit_ref 0.979 _refine_ls_restrained_S_all 0.979 _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 I1 I 0.36799(12) 0.61363(7) 0.18016(6) 0.0366(2) Uani 1 1 d . . . I2 I 0.29737(13) 0.32589(7) 0.17091(6) 0.0382(2) Uani 1 1 d . . . I3 I 0.69620(14) 0.16843(7) 0.21593(7) 0.0438(3) Uani 1 1 d . . . I4 I 0.69195(12) -0.10924(6) 0.21309(6) 0.0352(2) Uani 1 1 d . . . Br1 Br 0.5308(2) 0.75705(10) 0.00645(10) 0.0432(4) Uani 1 1 d . . . Se1 Se 0.29600(19) 0.58690(10) 0.40568(10) 0.0356(3) Uani 1 1 d . . . Se2 Se 0.2320(2) 0.34483(10) 0.39816(10) 0.0392(3) Uani 1 1 d . . . S1 S 0.2418(5) 0.5777(3) 0.6313(3) 0.0399(8) Uani 1 1 d . . . S2 S 0.1857(5) 0.3517(3) 0.6253(3) 0.0424(9) Uani 1 1 d . . . Se3 Se 0.7417(2) 0.15696(10) 0.45433(10) 0.0381(3) Uani 1 1 d . . . Se4 Se 0.73611(19) -0.07896(10) 0.45392(10) 0.0351(3) Uani 1 1 d . . . S3 S 0.7792(5) 0.1637(2) 0.6854(2) 0.0348(8) Uani 1 1 d . . . S4 S 0.7736(5) -0.0557(2) 0.6947(2) 0.0350(7) Uani 1 1 d . . . O1 O 0.2043(15) 0.5742(8) 0.8132(7) 0.055(3) Uani 1 1 d . . . O2 O 0.1461(15) 0.3539(8) 0.8061(8) 0.062(3) Uani 1 1 d . . . O3 O 0.8292(13) 0.1815(7) 0.8752(6) 0.040(2) Uani 1 1 d . . . O4 O 0.8136(14) -0.0334(7) 0.8852(7) 0.043(2) Uani 1 1 d . . . C1 C 0.3018(18) 0.5183(10) 0.2905(9) 0.035(3) Uani 1 1 d . . . C2 C 0.2718(16) 0.4151(10) 0.2871(9) 0.032(3) Uani 1 1 d . . . C3 C 0.2488(19) 0.4660(9) 0.4723(10) 0.036(3) Uani 1 1 d . . . C4 C 0.2282(16) 0.4640(10) 0.5644(10) 0.035(3) Uani 1 1 d . . . C5 C 0.2003(17) 0.5153(12) 0.7359(9) 0.041(4) Uani 1 1 d . . . C6 C 0.1777(18) 0.4133(11) 0.7324(10) 0.040(3) Uani 1 1 d . . . C7 C 0.186(5) 0.5193(17) 0.8909(13) 0.167(16) Uani 1 1 d . . . H7A H 0.0737 0.5255 0.9087 0.200 Uiso 1 1 calc R . . H7B H 0.2861 0.5561 0.9421 0.200 Uiso 1 1 calc R . . C8 C 0.180(3) 0.4168(16) 0.8962(12) 0.082(7) Uani 1 1 d . . . H8A H 0.0842 0.3851 0.9309 0.098 Uiso 1 1 calc R . . H8B H 0.2958 0.4132 0.9346 0.098 Uiso 1 1 calc R . . C9 C 0.7307(17) 0.0838(9) 0.3351(8) 0.028(3) Uani 1 1 d . . . C10 C 0.7280(16) -0.0149(9) 0.3369(9) 0.032(3) Uani 1 1 d . . . C11 C 0.7502(15) 0.0422(9) 0.5276(9) 0.028(3) Uani 1 1 d . . . C12 C 0.7661(16) 0.0482(9) 0.6244(9) 0.028(3) Uani 1 1 d . . . C13 C 0.8064(17) 0.1139(10) 0.7982(8) 0.030(3) Uani 1 1 d . . . C14 C 0.8028(17) 0.0160(10) 0.8041(10) 0.035(3) Uani 1 1 d . . . C15 C 0.882(2) 0.1372(10) 0.9638(10) 0.041(3) Uani 1 1 d . . . H15A H 0.8599 0.1750 1.0167 0.049 Uiso 1 1 calc R . . H15B H 1.0124 0.1427 0.9749 0.049 Uiso 1 1 calc R . . C16 C 0.775(2) 0.0271(10) 0.9599(10) 0.042(3) Uani 1 1 d . . . H16A H 0.8059 -0.0002 1.0215 0.050 Uiso 1 1 calc R . . H16B H 0.6443 0.0218 0.9475 0.050 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.0442(5) 0.0369(5) 0.0279(5) 0.0077(4) 0.0035(4) 0.0127(4) I2 0.0522(5) 0.0372(5) 0.0247(5) -0.0035(4) 0.0032(4) 0.0149(4) I3 0.0704(7) 0.0400(5) 0.0268(5) 0.0098(4) 0.0149(4) 0.0211(5) I4 0.0432(5) 0.0334(5) 0.0290(5) -0.0045(4) 0.0089(4) 0.0099(4) Br1 0.0695(10) 0.0352(8) 0.0254(8) -0.0008(6) 0.0099(7) 0.0152(7) Se1 0.0524(8) 0.0325(7) 0.0265(8) 0.0023(5) 0.0059(6) 0.0208(6) Se2 0.0619(9) 0.0307(7) 0.0265(8) 0.0041(5) 0.0115(6) 0.0137(6) S1 0.053(2) 0.039(2) 0.030(2) -0.0015(15) 0.0051(16) 0.0193(16) S2 0.058(2) 0.038(2) 0.025(2) 0.0021(14) 0.0065(16) 0.0059(16) Se3 0.0662(9) 0.0287(7) 0.0211(7) 0.0008(5) 0.0071(6) 0.0172(6) Se4 0.0535(8) 0.0306(7) 0.0235(7) 0.0025(5) 0.0053(6) 0.0174(6) S3 0.056(2) 0.0293(17) 0.0197(18) 0.0036(13) 0.0038(14) 0.0154(15) S4 0.052(2) 0.0310(18) 0.0239(18) 0.0041(13) 0.0043(15) 0.0165(15) O1 0.074(7) 0.070(7) 0.022(6) -0.011(5) -0.001(5) 0.030(6) O2 0.072(7) 0.066(8) 0.032(7) 0.014(5) 0.015(5) -0.010(6) O3 0.072(7) 0.039(5) 0.012(5) -0.002(4) 0.013(4) 0.018(5) O4 0.073(7) 0.033(5) 0.025(6) 0.010(4) 0.007(5) 0.022(5) C1 0.052(8) 0.043(8) 0.018(7) 0.012(5) 0.005(6) 0.027(6) C2 0.032(7) 0.042(8) 0.024(7) -0.003(5) 0.007(5) 0.015(6) C3 0.052(8) 0.027(7) 0.029(8) 0.004(5) -0.004(6) 0.016(6) C4 0.028(6) 0.039(8) 0.036(8) -0.006(6) 0.004(6) 0.005(5) C5 0.031(7) 0.085(12) 0.011(7) 0.005(7) -0.002(5) 0.029(7) C6 0.032(7) 0.044(9) 0.038(9) -0.001(6) 0.006(6) -0.001(6) C7 0.32(4) 0.086(17) 0.022(11) -0.036(11) 0.068(17) -0.07(2) C8 0.136(18) 0.110(17) 0.031(11) 0.004(10) 0.012(11) 0.090(15) C9 0.042(7) 0.027(6) 0.015(6) 0.003(5) 0.003(5) 0.012(5) C10 0.032(6) 0.037(7) 0.018(7) -0.019(5) -0.001(5) 0.004(5) C11 0.027(6) 0.033(7) 0.026(7) 0.010(5) 0.003(5) 0.015(5) C12 0.033(7) 0.033(7) 0.023(7) 0.004(5) 0.008(5) 0.013(5) C13 0.038(7) 0.043(8) 0.014(6) 0.006(5) 0.005(5) 0.021(6) C14 0.038(7) 0.032(7) 0.030(8) -0.003(6) 0.005(6) 0.002(6) C15 0.058(9) 0.041(8) 0.020(7) 0.007(6) 0.006(6) 0.010(7) C16 0.060(9) 0.042(8) 0.026(8) 0.013(6) 0.016(7) 0.012(7) _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 I1 C1 2.097(13) . ? I2 C2 2.103(12) . ? I3 C9 2.077(12) . ? I4 C10 2.089(10) . ? Se1 C1 1.884(13) . ? Se1 C3 1.888(13) . ? Se2 C2 1.887(14) . ? Se2 C3 1.898(12) . ? S1 C5 1.761(15) . ? S1 C4 1.765(13) . ? S2 C4 1.744(15) . ? S2 C6 1.745(15) . ? Se3 C11 1.894(12) . ? Se3 C9 1.927(11) . ? Se4 C10 1.886(14) . ? Se4 C11 1.900(12) . ? S3 C12 1.747(12) . ? S3 C13 1.747(12) . ? S4 C12 1.746(13) . ? S4 C14 1.767(13) . ? O1 C5 1.339(15) . ? O1 C7 1.35(2) . ? O2 C6 1.349(17) . ? O2 C8 1.469(18) . ? O3 C13 1.369(13) . ? O3 C15 1.440(15) . ? O4 C14 1.341(16) . ? O4 C16 1.455(15) . ? C1 C2 1.352(17) . ? C3 C4 1.349(19) . ? C5 C6 1.344(19) . ? C7 C8 1.38(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.332(16) . ? C11 C12 1.357(16) . ? C13 C14 1.323(17) . ? C15 C16 1.489(18) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? 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 C1 Se1 C3 94.3(6) . . ? C2 Se2 C3 93.7(6) . . ? C5 S1 C4 94.5(7) . . ? C4 S2 C6 94.6(7) . . ? C11 Se3 C9 93.7(5) . . ? C10 Se4 C11 94.0(5) . . ? C12 S3 C13 93.6(6) . . ? C12 S4 C14 94.3(6) . . ? C5 O1 C7 112.0(14) . . ? C6 O2 C8 111.2(13) . . ? C13 O3 C15 110.7(10) . . ? C14 O4 C16 108.6(10) . . ? C2 C1 Se1 118.6(10) . . ? C2 C1 I1 126.0(10) . . ? Se1 C1 I1 115.3(6) . . ? C1 C2 Se2 119.2(9) . . ? C1 C2 I2 124.6(10) . . ? Se2 C2 I2 115.7(6) . . ? C4 C3 Se1 123.9(9) . . ? C4 C3 Se2 122.0(10) . . ? Se1 C3 Se2 114.1(7) . . ? C3 C4 S2 123.4(10) . . ? C3 C4 S1 121.0(11) . . ? S2 C4 S1 115.6(8) . . ? O1 C5 C6 125.8(14) . . ? O1 C5 S1 117.3(12) . . ? C6 C5 S1 116.8(10) . . ? C5 C6 O2 124.5(13) . . ? C5 C6 S2 118.5(11) . . ? O2 C6 S2 117.0(11) . . ? O1 C7 C8 126.0(17) . . ? O1 C7 H7A 105.8 . . ? C8 C7 H7A 105.8 . . ? O1 C7 H7B 105.8 . . ? C8 C7 H7B 105.8 . . ? H7A C7 H7B 106.2 . . ? C7 C8 O2 118.1(15) . . ? C7 C8 H8A 107.8 . . ? O2 C8 H8A 107.8 . . ? C7 C8 H8B 107.8 . . ? O2 C8 H8B 107.8 . . ? H8A C8 H8B 107.1 . . ? C10 C9 Se3 118.1(9) . . ? C10 C9 I3 128.0(9) . . ? Se3 C9 I3 113.6(5) . . ? C9 C10 Se4 120.1(9) . . ? C9 C10 I4 123.1(10) . . ? Se4 C10 I4 116.6(6) . . ? C12 C11 Se3 121.9(9) . . ? C12 C11 Se4 124.0(9) . . ? Se3 C11 Se4 114.1(6) . . ? C11 C12 S4 123.4(9) . . ? C11 C12 S3 120.4(9) . . ? S4 C12 S3 116.3(7) . . ? C14 C13 O3 124.7(12) . . ? C14 C13 S3 119.3(10) . . ? O3 C13 S3 116.0(9) . . ? C13 C14 O4 125.7(12) . . ? C13 C14 S4 116.4(10) . . ? O4 C14 S4 117.8(9) . . ? O3 C15 C16 110.4(11) . . ? O3 C15 H15A 109.6 . . ? C16 C15 H15A 109.6 . . ? O3 C15 H15B 109.6 . . ? C16 C15 H15B 109.6 . . ? H15A C15 H15B 108.1 . . ? O4 C16 C15 111.2(11) . . ? O4 C16 H16A 109.4 . . ? C15 C16 H16A 109.4 . . ? O4 C16 H16B 109.4 . . ? C15 C16 H16B 109.4 . . ? H16A C16 H16B 108.0 . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 28.57 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 1.885 _refine_diff_density_min -1.349 _refine_diff_density_rms 0.276 data_dietcl_face _database_code_depnum_ccdc_archive 'CCDC 281976' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H12 Cl I4 O2 S12' _chemical_formula_weight 1164.03 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' 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' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 7.6827(11) _cell_length_b 30.305(4) _cell_length_c 13.1946(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3072.0(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6460 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 28.17 _exptl_crystal_description plate _exptl_crystal_colour black _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.015 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 2.517 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2180 _exptl_absorpt_coefficient_mu 4.979 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.1776 _exptl_absorpt_correction_T_max 0.9073 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 21935 _diffrn_reflns_av_R_equivalents 0.0793 _diffrn_reflns_av_sigmaI/netI 0.0424 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -40 _diffrn_reflns_limit_k_max 39 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.34 _diffrn_reflns_theta_max 28.44 _reflns_number_total 3919 _reflns_number_gt 3107 _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^)+(0.0524P)^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_number_reflns 3919 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0485 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.0958 _refine_ls_wR_factor_gt 0.0914 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.001 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 I1 I 1.00038(3) 0.680777(9) 0.819193(19) 0.03882(10) Uani 1 1 d . . . I2 I 1.02275(4) 0.679494(9) 0.52849(2) 0.04065(10) Uani 1 1 d . . . S1 S 0.87580(14) 0.58049(3) 0.78284(7) 0.0387(2) Uani 1 1 d . . . S2 S 0.89290(14) 0.57984(3) 0.56319(7) 0.0416(2) Uani 1 1 d . . . C2 C 0.9521(5) 0.62827(12) 0.6234(3) 0.0347(8) Uani 1 1 d . . . C1 C 0.9456(5) 0.62867(12) 0.7243(3) 0.0334(8) Uani 1 1 d . . . S5 S 0.54416(14) 0.39543(3) 0.79495(7) 0.0396(2) Uani 1 1 d . . . S3 S 0.70714(13) 0.48293(3) 0.78031(7) 0.0376(2) Uani 1 1 d . . . S4 S 0.72333(15) 0.48315(3) 0.55977(7) 0.0440(3) Uani 1 1 d . . . S6 S 0.56349(18) 0.39774(4) 0.53196(8) 0.0535(3) Uani 1 1 d . . . C5 C 0.6195(4) 0.43763(11) 0.7184(3) 0.0319(8) Uani 1 1 d . . . C4 C 0.7615(5) 0.51151(13) 0.6711(2) 0.0350(9) Uani 1 1 d . . . C3 C 0.8343(5) 0.55213(12) 0.6718(2) 0.0339(8) Uani 1 1 d . . . C6 C 0.6279(5) 0.43779(12) 0.6171(3) 0.0342(8) Uani 1 1 d . . . C8 C 0.4827(6) 0.35502(16) 0.6116(3) 0.0515(11) Uani 1 1 d . . . H8A H 0.3608 0.3608 0.6256 0.062 Uiso 1 1 calc R . . H8B H 0.4893 0.3273 0.5750 0.062 Uiso 1 1 calc R . . C7 C 0.5761(6) 0.34991(13) 0.7099(3) 0.0433(9) Uani 1 1 d . . . H7A H 0.6996 0.3467 0.6966 0.052 Uiso 1 1 calc R . . H7B H 0.5365 0.3231 0.7427 0.052 Uiso 1 1 calc R . . Cl1 Cl 0.1553(2) 0.7500 0.37319(10) 0.0489(4) Uani 1 2 d S . . O1 O 0.0092(6) 0.7500 0.9807(3) 0.0526(11) Uani 1 2 d S . . O2 O 0.2345(6) 0.7500 0.1419(3) 0.0788(16) Uani 1 2 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 I1 0.04450(18) 0.03355(17) 0.03842(17) -0.00291(10) 0.00061(10) -0.00297(10) I2 0.04865(17) 0.03565(17) 0.03766(16) 0.00554(11) -0.00296(11) -0.00297(11) S1 0.0533(6) 0.0330(5) 0.0297(4) -0.0010(4) 0.0007(4) -0.0036(4) S2 0.0606(6) 0.0344(5) 0.0299(4) 0.0003(4) 0.0003(4) -0.0029(5) C2 0.0368(19) 0.031(2) 0.0365(19) 0.0047(16) -0.0007(16) 0.0021(15) C1 0.037(2) 0.0269(18) 0.0365(19) -0.0022(16) 0.0003(16) 0.0026(15) S5 0.0499(6) 0.0364(5) 0.0323(4) 0.0024(4) 0.0026(4) -0.0030(5) S3 0.0517(6) 0.0339(5) 0.0273(4) -0.0033(4) 0.0013(4) -0.0030(4) S4 0.0671(7) 0.0369(6) 0.0281(4) -0.0011(4) 0.0024(5) -0.0086(5) S6 0.0838(9) 0.0438(6) 0.0328(5) -0.0051(5) -0.0072(5) -0.0143(6) C5 0.0360(19) 0.0286(19) 0.0312(17) 0.0000(15) 0.0001(15) 0.0039(15) C4 0.042(2) 0.036(2) 0.0273(18) -0.0028(15) 0.0012(15) 0.0006(17) C3 0.045(2) 0.030(2) 0.0273(17) -0.0014(15) -0.0021(15) 0.0024(16) C6 0.045(2) 0.0258(18) 0.0320(18) -0.0016(15) -0.0047(15) 0.0009(16) C8 0.062(3) 0.044(3) 0.049(2) -0.007(2) 0.006(2) -0.015(2) C7 0.055(3) 0.026(2) 0.049(2) 0.0032(18) 0.003(2) 0.0004(18) Cl1 0.0603(9) 0.0496(9) 0.0369(7) 0.000 0.0125(6) 0.000 O1 0.071(3) 0.045(3) 0.041(2) 0.000 -0.0061(19) 0.000 O2 0.061(3) 0.133(5) 0.042(2) 0.000 -0.003(2) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C1 2.059(4) . ? I2 C2 2.067(4) . ? S1 C3 1.728(3) . ? S1 C1 1.737(4) . ? S2 C3 1.722(3) . ? S2 C2 1.730(4) . ? C2 C1 1.332(5) . ? S5 C5 1.730(4) . ? S5 C7 1.795(4) . ? S3 C4 1.732(4) . ? S3 C5 1.734(4) . ? S4 C4 1.727(3) . ? S4 C6 1.732(4) . ? S6 C6 1.726(4) . ? S6 C8 1.779(4) . ? C5 C6 1.337(5) . ? C4 C3 1.352(5) . ? C8 C7 1.491(6) . ? 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 C3 S1 C1 95.63(17) . . ? C3 S2 C2 95.76(17) . . ? C1 C2 S2 117.2(3) . . ? C1 C2 I2 127.5(3) . . ? S2 C2 I2 115.35(18) . . ? C2 C1 S1 116.6(3) . . ? C2 C1 I1 127.4(3) . . ? S1 C1 I1 115.93(18) . . ? C5 S5 C7 99.06(18) . . ? C4 S3 C5 95.59(17) . . ? C4 S4 C6 95.47(17) . . ? C6 S6 C8 103.12(18) . . ? C6 C5 S5 127.0(3) . . ? C6 C5 S3 116.7(3) . . ? S5 C5 S3 116.11(19) . . ? C3 C4 S4 122.0(3) . . ? C3 C4 S3 123.3(3) . . ? S4 C4 S3 114.7(2) . . ? C4 C3 S2 123.1(3) . . ? C4 C3 S1 122.4(3) . . ? S2 C3 S1 114.5(2) . . ? C5 C6 S6 129.3(3) . . ? C5 C6 S4 117.4(3) . . ? S6 C6 S4 113.3(2) . . ? C7 C8 S6 114.9(3) . . ? C8 C7 S5 113.5(3) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 28.44 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.397 _refine_diff_density_min -0.670 _refine_diff_density_rms 0.152