# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_mol1 _database_code_depnum_ccdc_archive 'CCDC 926138' #TrackingRef 'JL159.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H10 I2 S6' _chemical_formula_sum 'C11 H10 I2 S6' _chemical_formula_weight 588.35 _chemical_absolute_configuration syn 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' 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 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.5711(2) _cell_length_b 7.2502(2) _cell_length_c 19.0229(5) _cell_angle_alpha 90.00 _cell_angle_beta 99.6650(10) _cell_angle_gamma 90.00 _cell_volume 893.42(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 30730 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.187 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 556 _exptl_absorpt_coefficient_mu 4.205 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.379 _exptl_absorpt_correction_T_max 0.630 #----------------------------- Remark ------------------------------------# # SADABS output: # # Estimated minimum and maximum transmission: 0.2453 0.4956# # The ratio of these values is more reliable than their absolute values! # #-------------------------------------------------------------------------# _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_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_method CCD _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19753 _diffrn_reflns_av_R_equivalents 0.0304 _diffrn_reflns_av_sigmaI/netI 0.0264 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.51 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4046 _reflns_number_gt 3388 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0148P)^2^+0.8193P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.014(19) _refine_ls_number_reflns 4046 _refine_ls_number_parameters 172 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0373 _refine_ls_R_factor_gt 0.0260 _refine_ls_wR_factor_ref 0.0530 _refine_ls_wR_factor_gt 0.0495 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.81125(4) 0.17064(5) 0.958785(14) 0.05301(8) Uani 1 1 d . . . I2 I 0.67147(4) -0.32617(6) 0.911534(16) 0.06163(9) Uani 1 1 d . . . S1 S 0.34494(18) 0.24466(17) 0.87118(7) 0.0560(3) Uani 1 1 d . . . S2 S 0.23425(17) -0.14666(17) 0.84201(7) 0.0537(3) Uani 1 1 d . . . S3 S -0.06950(18) 0.37149(18) 0.76186(6) 0.0530(3) Uani 1 1 d . . . S4 S -0.19009(19) -0.01648(17) 0.73849(7) 0.0535(3) Uani 1 1 d . . . S5 S -0.30011(18) 0.4980(2) 0.62022(7) 0.0589(3) Uani 1 1 d . . . S6 S -0.47139(18) 0.05414(19) 0.60112(7) 0.0559(3) Uani 1 1 d . . . C1 C 0.5311(6) 0.0791(6) 0.9001(2) 0.0448(10) Uani 1 1 d . . . C2 C 0.4840(6) -0.0968(6) 0.8866(2) 0.0439(10) Uani 1 1 d . . . C3 C 0.1681(6) 0.0860(6) 0.8241(2) 0.0455(10) Uani 1 1 d . . . C4 C -0.0033(6) 0.1402(7) 0.7805(2) 0.0444(12) Uani 1 1 d . . . C5 C -0.2371(7) 0.3178(7) 0.6813(2) 0.0452(10) Uani 1 1 d . . . C6 C -0.2935(6) 0.1419(7) 0.6722(2) 0.0449(11) Uani 1 1 d . . . C7 C -0.6308(8) 0.5767(8) 0.6878(3) 0.0685(14) Uani 1 1 d . . . H7A H -0.5392 0.6714 0.7096 0.103 Uiso 1 1 calc R . . H7B H -0.6161 0.4690 0.7176 0.103 Uiso 1 1 calc R . . H7C H -0.7706 0.6201 0.6821 0.103 Uiso 1 1 calc R . . C8 C -0.5776(7) 0.5282(7) 0.6151(3) 0.0564(12) Uani 1 1 d . . . H8 H -0.6115 0.6389 0.5859 0.068 Uiso 1 1 calc R . . C9 C -0.7127(7) 0.3758(8) 0.5760(3) 0.0624(14) Uani 1 1 d . . . H9A H -0.8547 0.4179 0.5697 0.075 Uiso 1 1 calc R . . H9B H -0.6768 0.3643 0.5288 0.075 Uiso 1 1 calc R . . C10 C -0.7061(5) 0.1852(10) 0.6080(2) 0.0498(10) Uani 1 1 d . . . H10 H -0.7190 0.1958 0.6584 0.060 Uiso 1 1 calc R . . C11 C -0.8853(7) 0.0643(9) 0.5696(3) 0.0736(16) Uani 1 1 d . . . H11A H -0.8775 -0.0561 0.5909 0.110 Uiso 1 1 calc R . . H11B H -0.8746 0.0537 0.5201 0.110 Uiso 1 1 calc R . . H11C H -1.0148 0.1204 0.5741 0.110 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 0.03649(13) 0.05403(15) 0.06194(16) -0.0035(2) -0.01078(11) -0.00060(17) I2 0.04570(15) 0.04996(15) 0.0818(2) -0.0049(2) -0.01090(13) 0.01023(19) S1 0.0439(6) 0.0464(6) 0.0686(8) -0.0045(5) -0.0166(6) 0.0056(5) S2 0.0400(6) 0.0491(6) 0.0648(7) -0.0015(6) -0.0124(5) -0.0011(5) S3 0.0424(6) 0.0510(6) 0.0589(7) -0.0025(6) -0.0104(5) 0.0009(5) S4 0.0433(6) 0.0518(7) 0.0589(7) 0.0059(6) -0.0107(5) -0.0039(5) S5 0.0426(6) 0.0697(8) 0.0636(8) 0.0237(7) 0.0063(5) 0.0000(6) S6 0.0436(6) 0.0686(8) 0.0496(6) -0.0096(6) -0.0096(5) 0.0035(5) C1 0.027(2) 0.057(3) 0.046(2) -0.007(2) -0.0058(17) 0.0049(19) C2 0.031(2) 0.052(3) 0.044(2) 0.000(2) -0.0065(17) 0.0028(18) C3 0.031(2) 0.052(2) 0.050(2) -0.0036(19) -0.0024(18) -0.0012(18) C4 0.0344(19) 0.056(3) 0.039(2) 0.005(2) -0.0039(15) 0.002(2) C5 0.037(2) 0.055(3) 0.041(2) 0.007(2) -0.0006(18) 0.009(2) C6 0.0335(19) 0.055(4) 0.042(2) 0.002(2) -0.0071(15) 0.000(2) C7 0.057(3) 0.073(3) 0.079(4) -0.008(3) 0.021(3) 0.001(3) C8 0.043(3) 0.060(3) 0.064(3) 0.016(2) 0.005(2) 0.009(2) C9 0.041(3) 0.090(4) 0.052(3) 0.012(3) -0.003(2) 0.010(3) C10 0.0355(18) 0.070(3) 0.0407(19) -0.011(3) -0.0014(15) 0.004(3) C11 0.039(3) 0.107(4) 0.071(3) -0.021(3) -0.004(2) -0.009(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 2.094(4) . ? I2 C2 2.076(4) . ? S1 C1 1.736(4) . ? S1 C3 1.768(4) . ? S2 C2 1.754(4) . ? S2 C3 1.761(5) . ? S3 C4 1.754(5) . ? S3 C5 1.773(4) . ? S4 C6 1.755(4) . ? S4 C4 1.762(4) . ? S5 C5 1.751(4) . ? S5 C8 1.823(5) . ? S6 C6 1.752(4) . ? S6 C10 1.835(5) . ? C1 C2 1.327(6) . ? C3 C4 1.341(5) . ? C5 C6 1.331(7) . ? C7 C8 1.525(7) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C9 1.529(7) . ? C8 H8 0.9800 . ? C9 C10 1.507(8) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.549(7) . ? C10 H10 0.9800 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S1 C3 94.5(2) . . ? C2 S2 C3 94.4(2) . . ? C4 S3 C5 93.5(2) . . ? C6 S4 C4 93.4(2) . . ? C5 S5 C8 104.4(2) . . ? C6 S6 C10 102.5(2) . . ? C2 C1 S1 118.3(3) . . ? C2 C1 I1 124.3(3) . . ? S1 C1 I1 117.3(2) . . ? C1 C2 S2 117.4(3) . . ? C1 C2 I2 128.0(3) . . ? S2 C2 I2 114.6(2) . . ? C4 C3 S2 123.7(3) . . ? C4 C3 S1 122.3(4) . . ? S2 C3 S1 113.9(2) . . ? C3 C4 S3 124.0(4) . . ? C3 C4 S4 122.7(4) . . ? S3 C4 S4 113.2(2) . . ? C6 C5 S5 126.8(3) . . ? C6 C5 S3 116.2(3) . . ? S5 C5 S3 116.9(3) . . ? C5 C6 S6 125.7(3) . . ? C5 C6 S4 117.9(3) . . ? S6 C6 S4 116.4(3) . . ? C8 C7 H7A 109.5 . . ? C8 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C8 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C7 C8 C9 113.9(4) . . ? C7 C8 S5 111.0(3) . . ? C9 C8 S5 115.7(4) . . ? C7 C8 H8 105.0 . . ? C9 C8 H8 105.0 . . ? S5 C8 H8 105.0 . . ? C10 C9 C8 119.4(4) . . ? C10 C9 H9A 107.5 . . ? C8 C9 H9A 107.5 . . ? C10 C9 H9B 107.5 . . ? C8 C9 H9B 107.5 . . ? H9A C9 H9B 107.0 . . ? C9 C10 C11 111.1(4) . . ? C9 C10 S6 114.4(3) . . ? C11 C10 S6 104.8(4) . . ? C9 C10 H10 108.8 . . ? C11 C10 H10 108.8 . . ? S6 C10 H10 108.8 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 S1 C1 C2 -6.2(4) . . . . ? C3 S1 C1 I1 176.8(3) . . . . ? S1 C1 C2 S2 -1.2(6) . . . . ? I1 C1 C2 S2 175.5(2) . . . . ? S1 C1 C2 I2 178.4(2) . . . . ? I1 C1 C2 I2 -4.8(7) . . . . ? C3 S2 C2 C1 8.0(4) . . . . ? C3 S2 C2 I2 -171.8(2) . . . . ? C2 S2 C3 C4 170.0(4) . . . . ? C2 S2 C3 S1 -11.8(3) . . . . ? C1 S1 C3 C4 -170.5(4) . . . . ? C1 S1 C3 S2 11.3(3) . . . . ? S2 C3 C4 S3 -179.5(3) . . . . ? S1 C3 C4 S3 2.4(6) . . . . ? S2 C3 C4 S4 2.9(6) . . . . ? S1 C3 C4 S4 -175.2(3) . . . . ? C5 S3 C4 C3 158.8(4) . . . . ? C5 S3 C4 S4 -23.4(3) . . . . ? C6 S4 C4 C3 -159.6(4) . . . . ? C6 S4 C4 S3 22.5(3) . . . . ? C8 S5 C5 C6 67.7(5) . . . . ? C8 S5 C5 S3 -116.0(3) . . . . ? C4 S3 C5 C6 15.5(4) . . . . ? C4 S3 C5 S5 -161.2(3) . . . . ? S5 C5 C6 S6 -8.5(7) . . . . ? S3 C5 C6 S6 175.1(3) . . . . ? S5 C5 C6 S4 174.2(3) . . . . ? S3 C5 C6 S4 -2.2(5) . . . . ? C10 S6 C6 C5 -58.6(5) . . . . ? C10 S6 C6 S4 118.7(3) . . . . ? C4 S4 C6 C5 -12.3(4) . . . . ? C4 S4 C6 S6 170.1(3) . . . . ? C5 S5 C8 C7 59.8(4) . . . . ? C5 S5 C8 C9 -71.9(4) . . . . ? C7 C8 C9 C10 -63.3(6) . . . . ? S5 C8 C9 C10 67.1(5) . . . . ? C8 C9 C10 C11 167.8(4) . . . . ? C8 C9 C10 S6 -73.9(5) . . . . ? C6 S6 C10 C9 80.9(3) . . . . ? C6 S6 C10 C11 -157.2(4) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.639 _refine_diff_density_min -0.532 _refine_diff_density_rms 0.080 data_(1)2Cl _database_code_depnum_ccdc_archive 'CCDC 926139' #TrackingRef 'JLE175.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C11 H10 I2 S6), Cl ' _chemical_formula_sum 'C22 H20 Cl I4 S12' _chemical_formula_weight 1212.27 _chemical_absolute_configuration syn 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' 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 'C 2 2 2' _symmetry_space_group_name_Hall 'C 2 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x, -y, -z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z' _cell_length_a 9.6986(4) _cell_length_b 26.2429(8) _cell_length_c 14.5803(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3711.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4297 _cell_measurement_theta_min 27.5 _cell_measurement_theta_max 3.58 _exptl_crystal_description prism _exptl_crystal_colour black _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.170 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2292 _exptl_absorpt_coefficient_mu 4.123 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.198 _exptl_absorpt_correction_T_max 0.573 #----------------------------- Remark ------------------------------------# # SADABS output: # # Estimated minimum and maximum transmission: 0.5109 0.7456 # # The ratio of these values is more reliable than their absolute values! # #-------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_method CCD _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27241 _diffrn_reflns_av_R_equivalents 0.0840 _diffrn_reflns_av_sigmaI/netI 0.0509 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.58 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4269 _reflns_number_gt 2866 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; EADP restraints were applied to the C6,C7 and C8 atoms. 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^)+(0.0162P)^2^+16.9183P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.05(9) _refine_ls_number_reflns 4269 _refine_ls_number_parameters 168 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0831 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.0823 _refine_ls_wR_factor_gt 0.0717 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.038 _refine_ls_shift/su_mean 0.007 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 C1 C 0.3930(6) 0.2124(3) 0.7515(16) 0.0458(17) Uani 1 1 d . . . C2 C 0.2447(15) 0.1326(6) 0.7042(11) 0.046(4) Uani 1 1 d . . . C3 C 0.2455(17) 0.1361(5) 0.7955(9) 0.037(4) Uani 1 1 d . . . C4 C 0.4832(6) 0.2527(2) 0.7474(15) 0.0420(15) Uani 1 1 d . . . C5 C 0.6719(17) 0.3174(5) 0.7894(11) 0.045(4) Uani 1 1 d . . . C6 C 0.8389(10) 0.4070(3) 0.8125(7) 0.0508(12) Uani 1 1 d . . . H6 H 0.9261 0.4009 0.7803 0.061 Uiso 1 1 calc R . . C7 C 0.7354(7) 0.4284(2) 0.7434(12) 0.0508(12) Uani 1 1 d . . . H7A H 0.6439 0.4170 0.7607 0.061 Uiso 1 1 calc R . . H7B H 0.7365 0.4653 0.7477 0.061 Uiso 1 1 calc R . . C8 C 0.7597(10) 0.4140(3) 0.6466(7) 0.0508(12) Uani 1 1 d . . . H8 H 0.6793 0.4243 0.6104 0.061 Uiso 1 1 calc R . . C9 C 0.6723(18) 0.3165(6) 0.6984(10) 0.040(4) Uani 1 1 d . . . C10 C 0.868(2) 0.4419(6) 0.8934(13) 0.086(6) Uani 1 1 d . . . H10A H 0.9394 0.4273 0.9307 0.129 Uiso 1 1 calc R . . H10B H 0.7858 0.4459 0.9292 0.129 Uiso 1 1 calc R . . H10C H 0.8977 0.4746 0.8712 0.129 Uiso 1 1 calc R . . C11 C 0.8872(18) 0.4409(6) 0.6080(13) 0.075(5) Uani 1 1 d . . . H11A H 0.8786 0.4770 0.6170 0.113 Uiso 1 1 calc R . . H11B H 0.8950 0.4337 0.5436 0.113 Uiso 1 1 calc R . . H11C H 0.9681 0.4287 0.6391 0.113 Uiso 1 1 calc R . . S1 S 0.3317(5) 0.18453(17) 0.6474(3) 0.0467(12) Uani 1 1 d . . . S2 S 0.3308(5) 0.18483(17) 0.8489(3) 0.0478(12) Uani 1 1 d . . . S3 S 0.5425(5) 0.28161(18) 0.8470(3) 0.0459(11) Uani 1 1 d . . . S4 S 0.7859(5) 0.34657(18) 0.8681(4) 0.0573(13) Uani 1 1 d . . . S5 S 0.7908(4) 0.34606(17) 0.6271(4) 0.0508(11) Uani 1 1 d . . . S6 S 0.5438(5) 0.28023(18) 0.6461(3) 0.0478(12) Uani 1 1 d . . . Cl1 Cl 0.0000 0.0000 0.5000 0.040(2) Uani 1 4 d S . . Cl2 Cl 0.0000 0.0000 0.0000 0.040(2) Uani 1 4 d S . . I1 I 0.14841(11) 0.08087(4) 0.61893(8) 0.0442(3) Uani 1 1 d . . . I2 I 0.14754(12) 0.08190(4) 0.87980(8) 0.0470(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.045(4) 0.043(4) 0.049(4) -0.016(10) 0.009(11) -0.003(3) C2 0.021(6) 0.037(8) 0.080(11) 0.012(7) 0.014(7) -0.003(6) C3 0.056(9) 0.034(7) 0.020(7) 0.010(5) 0.002(6) -0.008(6) C4 0.044(3) 0.032(3) 0.050(4) 0.006(10) -0.002(11) -0.007(3) C5 0.038(8) 0.027(7) 0.070(10) -0.003(5) -0.001(6) -0.014(6) C6 0.042(3) 0.043(3) 0.067(4) 0.009(3) 0.002(3) -0.003(2) C7 0.042(3) 0.043(3) 0.067(4) 0.009(3) 0.002(3) -0.003(2) C8 0.042(3) 0.043(3) 0.067(4) 0.009(3) 0.002(3) -0.003(2) C9 0.051(9) 0.044(8) 0.027(6) -0.005(5) -0.002(5) 0.005(6) C10 0.110(12) 0.075(11) 0.073(11) -0.023(10) 0.036(10) -0.064(10) C11 0.091(11) 0.060(9) 0.075(11) -0.001(9) 0.043(10) -0.026(8) S1 0.045(3) 0.048(3) 0.047(2) 0.000(2) 0.001(2) -0.016(2) S2 0.056(3) 0.044(2) 0.043(2) 0.0016(19) -0.003(3) -0.009(2) S3 0.052(2) 0.044(2) 0.042(2) -0.0017(18) 0.0025(18) -0.014(2) S4 0.069(3) 0.045(2) 0.059(3) 0.004(2) -0.021(2) -0.007(2) S5 0.046(2) 0.052(2) 0.054(3) 0.001(2) 0.007(2) -0.014(2) S6 0.049(2) 0.042(2) 0.052(3) -0.0011(19) 0.0011(19) -0.007(2) Cl1 0.057(6) 0.019(4) 0.042(5) 0.000 0.000 0.000 Cl2 0.047(5) 0.037(5) 0.035(4) 0.000 0.000 0.000 I1 0.0435(5) 0.0420(6) 0.0472(6) -0.0055(6) 0.0000(7) -0.0055(6) I2 0.0520(6) 0.0408(6) 0.0482(6) 0.0076(6) -0.0045(7) -0.0075(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 C1 C4 1.373(9) . ? C1 S2 1.70(2) . ? C1 S1 1.787(19) . ? C2 C3 1.335(10) . ? C2 S1 1.804(15) . ? C2 I1 2.065(16) . ? C3 S2 1.710(16) . ? C3 I2 2.106(13) . ? C4 S3 1.737(19) . ? C4 S6 1.745(19) . ? C5 C9 1.327(10) . ? C5 S4 1.768(16) . ? C5 S3 1.778(15) . ? C6 C10 1.520(18) . ? C6 C7 1.530(14) . ? C6 S4 1.853(10) . ? C6 H6 0.9800 . ? C7 C8 1.479(18) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C11 1.531(17) . ? C8 S5 1.831(10) . ? C8 H8 0.9800 . ? C9 S5 1.733(17) . ? C9 S6 1.744(17) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 C1 S2 126.1(17) . . ? C4 C1 S1 119.4(17) . . ? S2 C1 S1 114.6(4) . . ? C3 C2 S1 113.8(15) . . ? C3 C2 I1 130.4(15) . . ? S1 C2 I1 115.6(8) . . ? C2 C3 S2 120.5(14) . . ? C2 C3 I2 122.2(15) . . ? S2 C3 I2 117.3(7) . . ? C1 C4 S3 120.7(17) . . ? C1 C4 S6 124.8(17) . . ? S3 C4 S6 114.5(3) . . ? C9 C5 S4 130.9(17) . . ? C9 C5 S3 117.8(16) . . ? S4 C5 S3 111.3(9) . . ? C10 C6 C7 114.3(11) . . ? C10 C6 S4 103.2(8) . . ? C7 C6 S4 114.8(6) . . ? C10 C6 H6 108.0 . . ? C7 C6 H6 108.0 . . ? S4 C6 H6 108.0 . . ? C8 C7 C6 115.5(8) . . ? C8 C7 H7A 108.4 . . ? C6 C7 H7A 108.4 . . ? C8 C7 H7B 108.4 . . ? C6 C7 H7B 108.4 . . ? H7A C7 H7B 107.5 . . ? C7 C8 C11 111.2(10) . . ? C7 C8 S5 115.0(6) . . ? C11 C8 S5 104.9(8) . . ? C7 C8 H8 108.5 . . ? C11 C8 H8 108.5 . . ? S5 C8 H8 108.5 . . ? C5 C9 S5 126.5(17) . . ? C5 C9 S6 116.4(16) . . ? S5 C9 S6 117.1(8) . . ? C6 C10 H10A 109.5 . . ? C6 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C6 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C1 S1 C2 94.3(7) . . ? C1 S2 C3 96.3(6) . . ? C4 S3 C5 94.0(7) . . ? C5 S4 C6 105.1(6) . . ? C9 S5 C8 103.5(6) . . ? C9 S6 C4 95.6(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag S1 C2 C3 S2 -3(3) . . . . ? I1 C2 C3 S2 -177.8(5) . . . . ? S1 C2 C3 I2 178.5(4) . . . . ? I1 C2 C3 I2 4(3) . . . . ? S2 C1 C4 S3 -1.4(9) . . . . ? S1 C1 C4 S3 178.8(4) . . . . ? S2 C1 C4 S6 -179.6(5) . . . . ? S1 C1 C4 S6 0.6(9) . . . . ? C10 C6 C7 C8 146.6(9) . . . . ? S4 C6 C7 C8 -94.3(9) . . . . ? C6 C7 C8 C11 -71.0(11) . . . . ? C6 C7 C8 S5 48.2(9) . . . . ? S4 C5 C9 S5 -1(3) . . . . ? S3 C5 C9 S5 -177.4(6) . . . . ? S4 C5 C9 S6 177.0(7) . . . . ? S3 C5 C9 S6 0(2) . . . . ? C4 C1 S1 C2 172.9(7) . . . . ? S2 C1 S1 C2 -6.9(6) . . . . ? C3 C2 S1 C1 5.8(17) . . . . ? I1 C2 S1 C1 -178.6(7) . . . . ? C4 C1 S2 C3 -174.1(8) . . . . ? S1 C1 S2 C3 5.7(7) . . . . ? C2 C3 S2 C1 -2(2) . . . . ? I2 C3 S2 C1 176.9(8) . . . . ? C1 C4 S3 C5 168.7(7) . . . . ? S6 C4 S3 C5 -13.0(6) . . . . ? C9 C5 S3 C4 7.8(18) . . . . ? S4 C5 S3 C4 -169.6(8) . . . . ? C9 C5 S4 C6 35(2) . . . . ? S3 C5 S4 C6 -147.6(7) . . . . ? C10 C6 S4 C5 151.0(11) . . . . ? C7 C6 S4 C5 25.9(11) . . . . ? C5 C9 S5 C8 -67(2) . . . . ? S6 C9 S5 C8 115.8(9) . . . . ? C7 C8 S5 C9 41.3(9) . . . . ? C11 C8 S5 C9 163.9(11) . . . . ? C5 C9 S6 C4 -8.1(18) . . . . ? S5 C9 S6 C4 169.8(9) . . . . ? C1 C4 S6 C9 -168.4(8) . . . . ? S3 C4 S6 C9 13.3(7) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.650 _refine_diff_density_min -0.556 _refine_diff_density_rms 0.106 data_(1)2Br _database_code_depnum_ccdc_archive 'CCDC 926140' #TrackingRef 'JLE186.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C11 H10 I2 S6), Br' _chemical_formula_sum 'C22 H20 Br I4 S12' _chemical_formula_weight 1256.72 _chemical_absolute_configuration syn 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' 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 'C 2 2 2' _symmetry_space_group_name_Hall 'C 2 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x, -y, -z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z' _cell_length_a 9.6691(4) _cell_length_b 26.5929(6) _cell_length_c 14.6760(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3773.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3864 _cell_measurement_theta_min 27.5 _cell_measurement_theta_max 3.58 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.212 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2364 _exptl_absorpt_coefficient_mu 5.042 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.626 _exptl_absorpt_correction_T_max 0.727 #----------------------------- Remark ------------------------------------# # SADABS output: # # Estimated minimum and maximum transmission: 0.5526 0.7234 # # The ratio of these values is more reliable than their absolute values! # #-------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_method CCD _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19459 _diffrn_reflns_av_R_equivalents 0.0398 _diffrn_reflns_av_sigmaI/netI 0.0307 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.57 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4356 _reflns_number_gt 3127 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0178P)^2^+7.3323P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.08(4) _refine_ls_number_reflns 4356 _refine_ls_number_parameters 180 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0558 _refine_ls_R_factor_gt 0.0294 _refine_ls_wR_factor_ref 0.0614 _refine_ls_wR_factor_gt 0.0535 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 C1 C 0.1042(5) 0.71436(16) 0.7474(11) 0.0452(11) Uani 1 1 d . . . C2 C 0.2489(14) 0.6374(4) 0.7024(7) 0.042(3) Uani 1 1 d . . . C3 C 0.2526(13) 0.6377(3) 0.7932(8) 0.043(3) Uani 1 1 d . . . C4 C 0.0138(4) 0.75372(14) 0.7512(10) 0.0440(10) Uani 1 1 d . . . C5 C -0.1789(12) 0.8173(4) 0.7999(8) 0.042(3) Uani 1 1 d . . . C6 C -0.2599(7) 0.9137(2) 0.8526(4) 0.0485(14) Uani 1 1 d . . . H6 H -0.1774 0.9229 0.8876 0.058 Uiso 1 1 calc R . . C7 C -0.2345(5) 0.92673(18) 0.7575(10) 0.0540(17) Uani 1 1 d . . . H7A H -0.1439 0.9141 0.7407 0.065 Uiso 1 1 calc R . . H7B H -0.2315 0.9631 0.7525 0.065 Uiso 1 1 calc R . . C8 C -0.3419(7) 0.9065(2) 0.6876(5) 0.0567(16) Uani 1 1 d . . . H8 H -0.4283 0.8999 0.7204 0.068 Uiso 1 1 calc R . . C9 C -0.1719(13) 0.8172(4) 0.7082(8) 0.043(3) Uani 1 1 d . . . C10 C -0.3817(12) 0.9400(4) 0.8949(8) 0.070(4) Uani 1 1 d . . . H10A H -0.4654 0.9284 0.8667 0.105 Uiso 1 1 calc R . . H10B H -0.3729 0.9756 0.8860 0.105 Uiso 1 1 calc R . . H10C H -0.3845 0.9327 0.9589 0.105 Uiso 1 1 calc R . . C11 C -0.3741(16) 0.9428(5) 0.6098(10) 0.094(5) Uani 1 1 d . . . H11A H -0.2891 0.9545 0.5832 0.141 Uiso 1 1 calc R . . H11B H -0.4253 0.9710 0.6330 0.141 Uiso 1 1 calc R . . H11C H -0.4280 0.9259 0.5642 0.141 Uiso 1 1 calc R . . S1 S 0.1657(4) 0.68709(12) 0.6511(2) 0.0494(8) Uani 1 1 d . . . S2 S 0.1663(3) 0.68672(12) 0.8513(2) 0.0469(8) Uani 1 1 d . . . S3 S -0.0470(4) 0.78097(11) 0.8523(2) 0.0493(9) Uani 1 1 d . . . S4 S -0.2938(3) 0.84668(12) 0.8722(3) 0.0540(8) Uani 1 1 d . . . S5 S -0.2873(3) 0.84709(12) 0.6326(2) 0.0551(9) Uani 1 1 d . . . S6 S -0.0462(4) 0.78211(10) 0.6529(2) 0.0470(8) Uani 1 1 d . . . Br1 Br 0.0000 1.0000 0.5000 0.0534(7) Uani 1 4 d S . . Br2 Br 0.0000 1.0000 1.0000 0.0449(6) Uani 1 4 d S . . I1 I 0.34720(9) 0.58454(3) 0.62108(6) 0.0504(2) Uani 1 1 d . . . I2 I 0.34631(8) 0.58393(3) 0.87939(6) 0.04692(19) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.047(2) 0.039(2) 0.049(3) 0.011(7) -0.005(8) 0.0054(19) C2 0.041(6) 0.051(7) 0.034(6) 0.006(5) -0.001(5) 0.002(6) C3 0.035(5) 0.024(5) 0.071(8) 0.006(5) 0.004(5) 0.010(5) C4 0.044(2) 0.037(2) 0.051(3) 0.005(8) -0.005(8) 0.0052(18) C5 0.041(6) 0.034(6) 0.049(6) 0.001(4) -0.005(5) 0.000(5) C6 0.038(3) 0.046(3) 0.061(4) -0.015(3) 0.005(3) 0.008(3) C7 0.045(3) 0.038(2) 0.079(5) -0.007(6) -0.008(6) 0.0021(19) C8 0.049(4) 0.051(3) 0.071(4) 0.008(3) 0.005(4) 0.018(3) C9 0.037(6) 0.031(5) 0.060(6) 0.003(4) -0.011(4) 0.010(5) C10 0.084(8) 0.062(6) 0.064(7) -0.016(6) -0.002(6) 0.051(6) C11 0.111(11) 0.080(9) 0.091(11) 0.008(8) -0.018(10) 0.013(8) S1 0.0539(19) 0.0444(18) 0.0500(19) -0.0001(15) -0.0036(19) 0.0145(18) S2 0.0459(17) 0.0465(19) 0.0484(18) 0.0019(15) 0.0019(18) 0.0127(17) S3 0.0488(18) 0.0445(16) 0.055(2) 0.0012(15) -0.0014(14) 0.0125(15) S4 0.0518(18) 0.0514(16) 0.0588(18) -0.0074(16) 0.0126(15) 0.0073(14) S5 0.060(2) 0.0476(16) 0.0573(18) -0.0061(15) -0.0140(16) 0.0132(15) S6 0.0525(18) 0.0408(15) 0.0476(19) 0.0020(14) 0.0019(14) 0.0101(15) Br1 0.0706(19) 0.0366(13) 0.0531(17) 0.000 0.000 0.000 Br2 0.0553(16) 0.0323(12) 0.0473(15) 0.000 0.000 0.000 I1 0.0540(5) 0.0433(5) 0.0541(5) -0.0081(5) -0.0059(5) 0.0085(5) I2 0.0451(4) 0.0418(5) 0.0538(5) 0.0086(4) 0.0001(4) 0.0064(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C4 1.365(6) . ? C1 S1 1.696(14) . ? C1 S2 1.796(13) . ? C2 C3 1.333(6) . ? C2 S1 1.721(11) . ? C2 I1 2.074(11) . ? C3 S2 1.767(11) . ? C3 I2 2.113(10) . ? C4 S6 1.729(12) . ? C4 S3 1.752(12) . ? C5 C9 1.348(7) . ? C5 S4 1.723(12) . ? C5 S3 1.776(12) . ? C6 C7 1.458(15) . ? C6 C10 1.503(11) . ? C6 S4 1.836(7) . ? C6 H6 0.9800 . ? C7 C8 1.557(12) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C11 1.528(14) . ? C8 S5 1.850(7) . ? C8 H8 0.9800 . ? C9 S6 1.734(12) . ? C9 S5 1.763(12) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 C1 S1 125.9(12) . . ? C4 C1 S2 119.5(12) . . ? S1 C1 S2 114.5(2) . . ? C3 C2 S1 116.4(11) . . ? C3 C2 I1 124.5(11) . . ? S1 C2 I1 118.9(6) . . ? C2 C3 S2 118.3(11) . . ? C2 C3 I2 127.3(11) . . ? S2 C3 I2 114.4(6) . . ? C1 C4 S6 121.0(12) . . ? C1 C4 S3 124.5(12) . . ? S6 C4 S3 114.4(2) . . ? C9 C5 S4 130.4(12) . . ? C9 C5 S3 113.2(12) . . ? S4 C5 S3 116.3(7) . . ? C7 C6 C10 114.6(6) . . ? C7 C6 S4 114.2(4) . . ? C10 C6 S4 104.3(6) . . ? C7 C6 H6 107.8 . . ? C10 C6 H6 107.8 . . ? S4 C6 H6 107.8 . . ? C6 C7 C8 115.9(6) . . ? C6 C7 H7A 108.3 . . ? C8 C7 H7A 108.3 . . ? C6 C7 H7B 108.3 . . ? C8 C7 H7B 108.3 . . ? H7A C7 H7B 107.4 . . ? C11 C8 C7 114.2(8) . . ? C11 C8 S5 105.8(7) . . ? C7 C8 S5 113.1(4) . . ? C11 C8 H8 107.8 . . ? C7 C8 H8 107.8 . . ? S5 C8 H8 107.8 . . ? C5 C9 S6 120.3(12) . . ? C5 C9 S5 126.5(13) . . ? S6 C9 S5 113.1(7) . . ? C6 C10 H10A 109.5 . . ? C6 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C6 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C1 S1 C2 97.4(5) . . ? C3 S2 C1 92.9(5) . . ? C4 S3 C5 95.7(5) . . ? C5 S4 C6 103.2(4) . . ? C9 S5 C8 107.0(5) . . ? C4 S6 C9 94.5(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag S1 C2 C3 S2 3(2) . . . . ? I1 C2 C3 S2 178.3(3) . . . . ? S1 C2 C3 I2 -179.4(3) . . . . ? I1 C2 C3 I2 -4(2) . . . . ? S1 C1 C4 S6 -1.8(6) . . . . ? S2 C1 C4 S6 178.9(3) . . . . ? S1 C1 C4 S3 -179.8(3) . . . . ? S2 C1 C4 S3 0.9(6) . . . . ? C10 C6 C7 C8 -70.6(8) . . . . ? S4 C6 C7 C8 49.7(6) . . . . ? C6 C7 C8 C11 142.6(8) . . . . ? C6 C7 C8 S5 -96.4(6) . . . . ? S4 C5 C9 S6 -178.0(4) . . . . ? S3 C5 C9 S6 2.0(18) . . . . ? S4 C5 C9 S5 -2(2) . . . . ? S3 C5 C9 S5 177.9(5) . . . . ? C4 C1 S1 C2 -172.1(6) . . . . ? S2 C1 S1 C2 7.2(5) . . . . ? C3 C2 S1 C1 -6.2(15) . . . . ? I1 C2 S1 C1 178.1(6) . . . . ? C2 C3 S2 C1 1.8(14) . . . . ? I2 C3 S2 C1 -176.2(5) . . . . ? C4 C1 S2 C3 173.5(5) . . . . ? S1 C1 S2 C3 -5.9(5) . . . . ? C1 C4 S3 C5 -168.5(5) . . . . ? S6 C4 S3 C5 13.4(4) . . . . ? C9 C5 S3 C4 -9.1(12) . . . . ? S4 C5 S3 C4 170.9(6) . . . . ? C9 C5 S4 C6 -65.1(16) . . . . ? S3 C5 S4 C6 114.9(6) . . . . ? C7 C6 S4 C5 39.6(6) . . . . ? C10 C6 S4 C5 165.5(7) . . . . ? C5 C9 S5 C8 35.5(16) . . . . ? S6 C9 S5 C8 -148.3(6) . . . . ? C11 C8 S5 C9 151.0(8) . . . . ? C7 C8 S5 C9 25.3(8) . . . . ? C1 C4 S6 C9 169.5(5) . . . . ? S3 C4 S6 C9 -12.4(5) . . . . ? C5 C9 S6 C4 6.3(14) . . . . ? S5 C9 S6 C4 -170.1(6) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.330 _refine_diff_density_min -0.444 _refine_diff_density_rms 0.089