# Electronic Supplementary Material (ESI) for RSC Advances # 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_130311xjb2_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H10 Br2 O4 S2' _chemical_formula_weight 454.15 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.665(3) _cell_length_b 8.8588(19) _cell_length_c 14.424(3) _cell_angle_alpha 90.00 _cell_angle_beta 110.803(3) _cell_angle_gamma 90.00 _cell_volume 1512.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 26.5 _exptl_crystal_description block _exptl_crystal_colour ? _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.994 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 5.645 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2653 _exptl_absorpt_correction_T_max 0.3981 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9083 _diffrn_reflns_av_R_equivalents 0.0416 _diffrn_reflns_av_sigmaI/netI 0.0489 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 26.50 _reflns_number_total 3134 _reflns_number_gt 2056 _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^)+(0.1085P)^2^+2.6536P] 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 SHELXL _refine_ls_extinction_coef 0.0100(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3134 _refine_ls_number_parameters 191 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1002 _refine_ls_R_factor_gt 0.0643 _refine_ls_wR_factor_ref 0.2005 _refine_ls_wR_factor_gt 0.1745 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.070 _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 Br1 Br -0.42277(8) 0.27244(13) 0.13954(8) 0.0840(4) Uani 1 1 d . . . Br2 Br 0.23911(7) 0.55616(11) 0.03750(6) 0.0731(4) Uani 1 1 d . . . C1 C -0.2764(6) 0.2169(9) 0.1514(6) 0.0558(18) Uani 1 1 d . . . C2 C -0.2472(5) 0.1229(7) 0.0948(4) 0.0393(14) Uani 1 1 d . . . C3 C -0.1273(6) 0.1040(8) 0.1277(5) 0.0450(15) Uani 1 1 d . . . C4 C -0.0698(6) 0.1824(8) 0.2086(5) 0.0466(16) Uani 1 1 d . . . C5 C -0.2740(7) -0.0700(8) -0.0400(8) 0.068(2) Uani 1 1 d . . . H5A H -0.2793 -0.1701 -0.0147 0.082 Uiso 1 1 calc R . . H5B H -0.3150 -0.0685 -0.1110 0.082 Uiso 1 1 calc R . . C6 C -0.1526(9) -0.0240(12) -0.0157(7) 0.083(3) Uani 1 1 d . . . H6A H -0.1171 -0.1056 -0.0387 0.100 Uiso 1 1 calc R . . H6B H -0.1540 0.0622 -0.0576 0.100 Uiso 1 1 calc R . . C7 C 0.0526(6) 0.1866(9) 0.2688(5) 0.0529(17) Uani 1 1 d . . . H7A H 0.0795 0.0835 0.2816 0.063 Uiso 1 1 calc R . . H7B H 0.0616 0.2323 0.3323 0.063 Uiso 1 1 calc R . . C8 C 0.1268(5) 0.2696(7) 0.2252(5) 0.0424(15) Uani 1 1 d . . . C9 C 0.2414(5) 0.2700(7) 0.2617(5) 0.0419(14) Uani 1 1 d . . . C10 C 0.2910(5) 0.3647(8) 0.2081(5) 0.0434(15) Uani 1 1 d . . . C11 C 0.2115(6) 0.4289(8) 0.1296(5) 0.0463(16) Uani 1 1 d . . . C12 C 0.4640(7) 0.3292(13) 0.3291(7) 0.087(3) Uani 1 1 d D . . H12A H 0.5429 0.3176 0.3370 0.104 Uiso 1 1 calc R . . H12B H 0.4595 0.4050 0.3761 0.104 Uiso 1 1 calc R . . C13 C 0.4237(7) 0.1917(12) 0.3515(9) 0.101(4) Uani 1 1 d D . . H13A H 0.4699 0.1632 0.4186 0.122 Uiso 1 1 calc R . . H13B H 0.4336 0.1149 0.3073 0.122 Uiso 1 1 calc R . . O1 O -0.3194(4) 0.0507(6) 0.0130(4) 0.0638(14) Uani 1 1 d . . . O2 O -0.0748(4) 0.0152(5) 0.0832(3) 0.0466(11) Uani 1 1 d . . . O3 O 0.4037(4) 0.3799(7) 0.2326(4) 0.0603(14) Uani 1 1 d . . . O4 O 0.3037(4) 0.1913(6) 0.3435(4) 0.0600(13) Uani 1 1 d . . . S1 S -0.16388(17) 0.2858(2) 0.24786(15) 0.0570(5) Uani 1 1 d . . . S2 S 0.07656(14) 0.3828(2) 0.12180(13) 0.0472(5) 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 Br1 0.0561(6) 0.0979(8) 0.1090(9) -0.0023(6) 0.0430(6) 0.0122(4) Br2 0.0663(6) 0.0881(7) 0.0673(6) 0.0231(4) 0.0267(4) -0.0059(4) C1 0.049(4) 0.063(5) 0.061(4) 0.001(4) 0.027(4) -0.004(3) C2 0.037(3) 0.046(4) 0.037(3) 0.002(3) 0.016(3) -0.002(3) C3 0.048(4) 0.045(4) 0.047(4) 0.005(3) 0.022(3) 0.000(3) C4 0.040(4) 0.055(4) 0.045(4) 0.005(3) 0.015(3) -0.005(3) C5 0.053(4) 0.038(4) 0.129(8) -0.010(4) 0.051(5) -0.001(3) C6 0.091(7) 0.097(7) 0.071(6) -0.022(5) 0.041(5) 0.010(5) C7 0.041(4) 0.065(5) 0.050(4) -0.001(3) 0.014(3) -0.012(3) C8 0.040(3) 0.048(4) 0.040(3) -0.005(3) 0.016(3) -0.005(3) C9 0.033(3) 0.051(4) 0.037(3) -0.001(3) 0.006(3) 0.002(3) C10 0.034(3) 0.052(4) 0.045(4) -0.008(3) 0.016(3) -0.001(3) C11 0.045(4) 0.049(4) 0.047(4) 0.006(3) 0.019(3) -0.001(3) C12 0.047(5) 0.132(9) 0.071(6) 0.022(6) 0.008(4) -0.011(5) C13 0.046(5) 0.114(9) 0.110(8) 0.027(7) -0.015(5) 0.008(5) O1 0.051(3) 0.076(4) 0.056(3) -0.008(3) 0.009(3) -0.004(3) O2 0.041(2) 0.059(3) 0.046(3) -0.004(2) 0.024(2) 0.011(2) O3 0.032(2) 0.093(4) 0.055(3) -0.003(3) 0.014(2) -0.006(2) O4 0.045(3) 0.075(4) 0.051(3) 0.010(3) 0.007(2) -0.001(2) S1 0.0628(12) 0.0593(12) 0.0567(11) -0.0108(9) 0.0309(10) -0.0053(9) S2 0.0365(9) 0.0520(10) 0.0504(10) 0.0021(8) 0.0121(7) 0.0058(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 Br1 C1 1.866(8) . ? Br2 C11 1.868(6) . ? C1 C2 1.309(10) . ? C1 S1 1.712(8) . ? C2 O1 1.368(8) . ? C2 C3 1.431(9) . ? C3 C4 1.331(10) . ? C3 O2 1.333(8) . ? C4 C7 1.484(9) . ? C4 S1 1.749(7) . ? C5 C6 1.507(13) . ? C5 O1 1.540(9) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 O2 1.459(10) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.496(9) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.357(9) . ? C8 S2 1.721(7) . ? C9 O4 1.356(8) . ? C9 C10 1.429(9) . ? C10 C11 1.345(9) . ? C10 O3 1.349(8) . ? C11 S2 1.721(7) . ? C12 C13 1.402(9) . ? C12 O3 1.403(10) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 O4 1.483(11) . ? C13 H13A 0.9700 . ? C13 H13B 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 C2 C1 S1 113.3(6) . . ? C2 C1 Br1 127.0(6) . . ? S1 C1 Br1 119.6(4) . . ? C1 C2 O1 125.8(6) . . ? C1 C2 C3 111.7(6) . . ? O1 C2 C3 122.5(6) . . ? C4 C3 O2 121.3(6) . . ? C4 C3 C2 114.6(6) . . ? O2 C3 C2 124.2(6) . . ? C3 C4 C7 131.2(7) . . ? C3 C4 S1 109.5(5) . . ? C7 C4 S1 119.2(5) . . ? C6 C5 O1 103.1(6) . . ? C6 C5 H5A 111.1 . . ? O1 C5 H5A 111.1 . . ? C6 C5 H5B 111.1 . . ? O1 C5 H5B 111.1 . . ? H5A C5 H5B 109.1 . . ? O2 C6 C5 124.8(8) . . ? O2 C6 H6A 106.1 . . ? C5 C6 H6A 106.1 . . ? O2 C6 H6B 106.1 . . ? C5 C6 H6B 106.1 . . ? H6A C6 H6B 106.3 . . ? C4 C7 C8 116.6(6) . . ? C4 C7 H7A 108.1 . . ? C8 C7 H7A 108.1 . . ? C4 C7 H7B 108.1 . . ? C8 C7 H7B 108.1 . . ? H7A C7 H7B 107.3 . . ? C9 C8 C7 125.7(6) . . ? C9 C8 S2 110.5(5) . . ? C7 C8 S2 123.8(5) . . ? O4 C9 C8 123.2(6) . . ? O4 C9 C10 122.8(6) . . ? C8 C9 C10 114.0(6) . . ? C11 C10 O3 125.8(6) . . ? C11 C10 C9 111.2(6) . . ? O3 C10 C9 122.9(6) . . ? C10 C11 S2 112.6(5) . . ? C10 C11 Br2 125.4(5) . . ? S2 C11 Br2 122.0(4) . . ? C13 C12 O3 113.1(8) . . ? C13 C12 H12A 109.0 . . ? O3 C12 H12A 109.0 . . ? C13 C12 H12B 109.0 . . ? O3 C12 H12B 109.0 . . ? H12A C12 H12B 107.8 . . ? C12 C13 O4 115.5(8) . . ? C12 C13 H13A 108.4 . . ? O4 C13 H13A 108.4 . . ? C12 C13 H13B 108.4 . . ? O4 C13 H13B 108.4 . . ? H13A C13 H13B 107.5 . . ? C2 O1 C5 120.0(6) . . ? C3 O2 C6 109.4(5) . . ? C10 O3 C12 112.4(6) . . ? C9 O4 C13 109.2(6) . . ? C1 S1 C4 90.9(3) . . ? C8 S2 C11 91.6(3) . . ? 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 C1 C2 O1 179.7(5) . . . . ? Br1 C1 C2 O1 2.4(11) . . . . ? S1 C1 C2 C3 -0.9(8) . . . . ? Br1 C1 C2 C3 -178.2(5) . . . . ? C1 C2 C3 C4 0.8(9) . . . . ? O1 C2 C3 C4 -179.9(6) . . . . ? C1 C2 C3 O2 -179.6(6) . . . . ? O1 C2 C3 O2 -0.3(10) . . . . ? O2 C3 C4 C7 -3.9(12) . . . . ? C2 C3 C4 C7 175.7(7) . . . . ? O2 C3 C4 S1 -179.8(5) . . . . ? C2 C3 C4 S1 -0.2(7) . . . . ? O1 C5 C6 O2 47.7(11) . . . . ? C3 C4 C7 C8 74.7(10) . . . . ? S1 C4 C7 C8 -109.7(7) . . . . ? C4 C7 C8 C9 -170.9(7) . . . . ? C4 C7 C8 S2 10.9(10) . . . . ? C7 C8 C9 O4 1.0(11) . . . . ? S2 C8 C9 O4 179.5(5) . . . . ? C7 C8 C9 C10 -177.1(6) . . . . ? S2 C8 C9 C10 1.3(7) . . . . ? O4 C9 C10 C11 179.4(6) . . . . ? C8 C9 C10 C11 -2.4(8) . . . . ? O4 C9 C10 O3 2.1(10) . . . . ? C8 C9 C10 O3 -179.7(6) . . . . ? O3 C10 C11 S2 179.6(5) . . . . ? C9 C10 C11 S2 2.4(8) . . . . ? O3 C10 C11 Br2 -0.9(10) . . . . ? C9 C10 C11 Br2 -178.1(5) . . . . ? O3 C12 C13 O4 -59.0(14) . . . . ? C1 C2 O1 C5 -173.4(7) . . . . ? C3 C2 O1 C5 7.4(10) . . . . ? C6 C5 O1 C2 -26.5(10) . . . . ? C4 C3 O2 C6 -165.0(7) . . . . ? C2 C3 O2 C6 15.5(9) . . . . ? C5 C6 O2 C3 -43.6(11) . . . . ? C11 C10 O3 C12 166.3(8) . . . . ? C9 C10 O3 C12 -16.8(10) . . . . ? C13 C12 O3 C10 43.9(12) . . . . ? C8 C9 O4 C13 168.9(8) . . . . ? C10 C9 O4 C13 -13.1(10) . . . . ? C12 C13 O4 C9 41.1(12) . . . . ? C2 C1 S1 C4 0.7(6) . . . . ? Br1 C1 S1 C4 178.2(5) . . . . ? C3 C4 S1 C1 -0.3(6) . . . . ? C7 C4 S1 C1 -176.8(6) . . . . ? C9 C8 S2 C11 0.0(5) . . . . ? C7 C8 S2 C11 178.5(6) . . . . ? C10 C11 S2 C8 -1.4(6) . . . . ? Br2 C11 S2 C8 179.0(4) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.259 _refine_diff_density_min -0.486 _refine_diff_density_rms 0.203 _database_code_depnum_ccdc_archive 'CCDC 943874' ####################################################################### # # 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_9130327hll_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H14 Br2 O4 S2 Si' _chemical_formula_weight 498.28 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' Br Br -0.2901 2.4595 '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' Si Si 0.0817 0.0704 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 13.2636(18) _cell_length_b 10.1957(13) _cell_length_c 27.784(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3757.3(9) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3054 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 26.5 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.762 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1968 _exptl_absorpt_coefficient_mu 4.615 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3479 _exptl_absorpt_correction_T_max 0.3800 _exptl_absorpt_process_details SADABS _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 23315 _diffrn_reflns_av_R_equivalents 0.0521 _diffrn_reflns_av_sigmaI/netI 0.0399 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 26.50 _reflns_number_total 3895 _reflns_number_gt 2338 _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^)+(0.0336P)^2^+10.4889P] 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_number_reflns 3895 _refine_ls_number_parameters 210 _refine_ls_number_restraints 32 _refine_ls_R_factor_all 0.0982 _refine_ls_R_factor_gt 0.0517 _refine_ls_wR_factor_ref 0.1223 _refine_ls_wR_factor_gt 0.1038 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.052 _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 Br1 Br 0.49609(6) 1.20007(6) 0.22920(3) 0.0850(3) Uani 1 1 d . . . Br2 Br 0.51429(6) 0.82922(7) -0.08357(2) 0.0839(3) Uani 1 1 d . . . C1 C 0.4885(5) 1.0381(5) 0.19833(18) 0.0538(14) Uani 1 1 d . . . C2 C 0.4046(4) 0.9682(5) 0.18943(18) 0.0488(13) Uani 1 1 d . . . C3 C 0.2389(7) 0.9109(10) 0.1938(4) 0.140(4) Uani 1 1 d DU . . H3A H 0.2171 0.8759 0.2245 0.167 Uiso 1 1 calc R . . H3B H 0.1816 0.9569 0.1802 0.167 Uiso 1 1 calc R . . C4 C 0.2585(6) 0.8015(8) 0.1634(3) 0.108(3) Uani 1 1 d DU . . H4A H 0.2272 0.7260 0.1784 0.130 Uiso 1 1 calc R . . H4B H 0.2221 0.8172 0.1336 0.130 Uiso 1 1 calc R . . C5 C 0.4265(4) 0.8511(5) 0.16378(18) 0.0463(13) Uani 1 1 d . . . C6 C 0.5256(4) 0.8319(5) 0.15368(18) 0.0499(13) Uani 1 1 d . . . C7 C 0.7311(6) 0.7160(8) 0.1410(3) 0.093(2) Uani 1 1 d U . . H7A H 0.7520 0.8009 0.1298 0.140 Uiso 1 1 calc R . . H7B H 0.7703 0.6496 0.1252 0.140 Uiso 1 1 calc R . . H7C H 0.7412 0.7103 0.1751 0.140 Uiso 1 1 calc R . . C8 C 0.5462(7) 0.5323(6) 0.1487(2) 0.098(3) Uani 1 1 d . . . H8A H 0.5635 0.5213 0.1820 0.148 Uiso 1 1 calc R . . H8B H 0.5754 0.4625 0.1302 0.148 Uiso 1 1 calc R . . H8C H 0.4742 0.5307 0.1452 0.148 Uiso 1 1 calc R . . C9 C 0.5823(4) 0.6985(5) 0.06041(19) 0.0509(13) Uani 1 1 d . . . C10 C 0.6246(4) 0.6130(5) 0.0288(2) 0.0510(13) Uani 1 1 d . . . C11 C 0.7081(7) 0.4266(8) 0.0064(3) 0.107(3) Uani 1 1 d DU . . H11A H 0.6662 0.3488 0.0082 0.128 Uiso 1 1 calc R . . H11B H 0.7765 0.3987 0.0133 0.128 Uiso 1 1 calc R . . C12 C 0.7067(8) 0.4681(8) -0.0420(3) 0.122(3) Uani 1 1 d DU . . H12A H 0.6893 0.3922 -0.0613 0.147 Uiso 1 1 calc R . . H12B H 0.7753 0.4917 -0.0504 0.147 Uiso 1 1 calc R . . C13 C 0.6087(4) 0.6434(5) -0.02046(18) 0.0486(13) Uani 1 1 d . . . C14 C 0.5532(4) 0.7530(5) -0.02544(19) 0.0525(13) Uani 1 1 d . . . O1 O 0.3111(3) 1.0039(4) 0.20349(16) 0.0732(12) Uani 1 1 d . . . O2 O 0.3534(3) 0.7646(4) 0.15082(15) 0.0676(11) Uani 1 1 d . . . O3 O 0.6795(3) 0.5064(4) 0.04301(14) 0.0683(11) Uani 1 1 d . . . O4 O 0.6453(3) 0.5703(4) -0.05709(14) 0.0671(11) Uani 1 1 d . . . S1 S 0.59381(11) 0.96268(14) 0.17664(5) 0.0557(4) Uani 1 1 d . . . S2 S 0.52145(11) 0.82080(13) 0.02886(5) 0.0557(4) Uani 1 1 d . . . Si1 Si 0.59553(14) 0.69147(15) 0.12699(6) 0.0579(4) 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 Br1 0.1178(6) 0.0583(4) 0.0788(5) -0.0291(3) -0.0065(4) -0.0017(4) Br2 0.1209(7) 0.0691(4) 0.0616(4) 0.0038(3) -0.0204(4) 0.0173(4) C1 0.076(4) 0.043(3) 0.042(3) -0.007(2) -0.001(3) 0.000(3) C2 0.056(3) 0.050(3) 0.041(3) 0.004(3) 0.004(3) 0.006(3) C3 0.090(6) 0.158(7) 0.171(7) -0.044(7) 0.023(6) -0.014(6) C4 0.074(5) 0.099(5) 0.152(7) -0.013(5) -0.010(5) -0.011(4) C5 0.057(4) 0.038(3) 0.044(3) 0.005(2) -0.005(3) -0.003(2) C6 0.065(4) 0.044(3) 0.041(3) 0.004(2) -0.002(3) 0.001(3) C7 0.093(2) 0.094(2) 0.093(2) -0.0008(10) -0.0011(10) 0.0023(10) C8 0.172(8) 0.047(4) 0.077(5) 0.004(3) 0.026(5) 0.004(4) C9 0.053(3) 0.043(3) 0.056(3) 0.002(3) 0.005(3) 0.007(2) C10 0.049(3) 0.043(3) 0.061(3) -0.001(3) 0.005(3) 0.006(2) C11 0.133(6) 0.094(5) 0.092(5) -0.012(4) 0.000(5) 0.057(5) C12 0.166(7) 0.102(5) 0.100(5) -0.009(5) 0.028(5) 0.062(5) C13 0.053(3) 0.045(3) 0.048(3) -0.008(3) 0.004(3) 0.002(2) C14 0.059(3) 0.047(3) 0.052(3) -0.002(3) -0.003(3) 0.003(3) O1 0.067(3) 0.064(3) 0.089(3) -0.006(2) 0.011(2) 0.006(2) O2 0.060(3) 0.058(2) 0.085(3) -0.013(2) -0.004(2) -0.010(2) O3 0.089(3) 0.054(2) 0.062(2) -0.006(2) 0.006(2) 0.029(2) O4 0.080(3) 0.061(2) 0.060(2) -0.012(2) 0.008(2) 0.017(2) S1 0.0616(9) 0.0485(8) 0.0570(8) 0.0001(7) 0.0000(7) -0.0067(7) S2 0.0638(9) 0.0445(7) 0.0588(9) -0.0026(6) 0.0003(7) 0.0115(7) Si1 0.0776(12) 0.0440(8) 0.0521(9) 0.0002(7) 0.0025(9) 0.0129(8) _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 Br1 C1 1.864(5) . ? Br2 C14 1.865(5) . ? C1 C2 1.344(7) . ? C1 S1 1.705(6) . ? C2 O1 1.350(6) . ? C2 C5 1.421(7) . ? C3 C4 1.424(8) . ? C3 O1 1.374(9) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 O2 1.360(9) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 O2 1.359(6) . ? C5 C6 1.358(7) . ? C6 S1 1.733(5) . ? C6 Si1 1.860(6) . ? C7 Si1 1.857(8) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 Si1 1.851(7) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.358(7) . ? C9 S2 1.725(5) . ? C9 Si1 1.860(6) . ? C10 O3 1.367(6) . ? C10 C13 1.420(7) . ? C11 O3 1.357(7) . ? C11 C12 1.408(7) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 O4 1.387(8) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.345(7) . ? C13 O4 1.352(6) . ? C14 S2 1.712(5) . ? 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 C2 C1 S1 112.0(4) . . ? C2 C1 Br1 126.8(4) . . ? S1 C1 Br1 121.2(3) . . ? C1 C2 O1 124.3(5) . . ? C1 C2 C5 111.6(5) . . ? O1 C2 C5 124.1(5) . . ? C4 C3 O1 122.0(7) . . ? C4 C3 H3A 106.8 . . ? O1 C3 H3A 106.8 . . ? C4 C3 H3B 106.8 . . ? O1 C3 H3B 106.8 . . ? H3A C3 H3B 106.7 . . ? O2 C4 C3 122.6(7) . . ? O2 C4 H4A 106.7 . . ? C3 C4 H4A 106.7 . . ? O2 C4 H4B 106.7 . . ? C3 C4 H4B 106.7 . . ? H4A C4 H4B 106.6 . . ? O2 C5 C6 122.8(5) . . ? O2 C5 C2 122.1(5) . . ? C6 C5 C2 115.0(5) . . ? C5 C6 S1 108.6(4) . . ? C5 C6 Si1 132.5(4) . . ? S1 C6 Si1 118.6(3) . . ? Si1 C7 H7A 109.5 . . ? Si1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? Si1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? Si1 C8 H8A 109.5 . . ? Si1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? Si1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 S2 109.2(4) . . ? C10 C9 Si1 125.4(4) . . ? S2 C9 Si1 125.3(3) . . ? C9 C10 O3 123.0(5) . . ? C9 C10 C13 114.9(5) . . ? O3 C10 C13 122.1(5) . . ? O3 C11 C12 122.1(6) . . ? O3 C11 H11A 106.8 . . ? C12 C11 H11A 106.8 . . ? O3 C11 H11B 106.8 . . ? C12 C11 H11B 106.8 . . ? H11A C11 H11B 106.7 . . ? C11 C12 O4 121.5(6) . . ? C11 C12 H12A 107.0 . . ? O4 C12 H12A 107.0 . . ? C11 C12 H12B 107.0 . . ? O4 C12 H12B 107.0 . . ? H12A C12 H12B 106.7 . . ? C14 C13 O4 125.3(5) . . ? C14 C13 C10 111.2(5) . . ? O4 C13 C10 123.5(5) . . ? C13 C14 S2 112.3(4) . . ? C13 C14 Br2 125.9(4) . . ? S2 C14 Br2 121.8(3) . . ? C2 O1 C3 113.4(5) . . ? C5 O2 C4 114.4(5) . . ? C11 O3 C10 114.2(5) . . ? C13 O4 C12 113.4(5) . . ? C1 S1 C6 92.8(3) . . ? C14 S2 C9 92.4(3) . . ? C8 Si1 C7 113.1(4) . . ? C8 Si1 C9 109.0(3) . . ? C7 Si1 C9 107.1(3) . . ? C8 Si1 C6 111.6(3) . . ? C7 Si1 C6 107.2(3) . . ? C9 Si1 C6 108.6(2) . . ? 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 C1 C2 O1 178.6(4) . . . . ? Br1 C1 C2 O1 -2.6(8) . . . . ? S1 C1 C2 C5 -0.7(6) . . . . ? Br1 C1 C2 C5 178.1(4) . . . . ? O1 C3 C4 O2 15.4(16) . . . . ? C1 C2 C5 O2 179.9(5) . . . . ? O1 C2 C5 O2 0.5(8) . . . . ? C1 C2 C5 C6 0.4(7) . . . . ? O1 C2 C5 C6 -178.9(5) . . . . ? O2 C5 C6 S1 -179.4(4) . . . . ? C2 C5 C6 S1 0.1(6) . . . . ? O2 C5 C6 Si1 -6.3(8) . . . . ? C2 C5 C6 Si1 173.2(4) . . . . ? S2 C9 C10 O3 178.9(4) . . . . ? Si1 C9 C10 O3 2.9(8) . . . . ? S2 C9 C10 C13 -0.3(6) . . . . ? Si1 C9 C10 C13 -176.3(4) . . . . ? O3 C11 C12 O4 -23.0(15) . . . . ? C9 C10 C13 C14 -0.4(7) . . . . ? O3 C10 C13 C14 -179.6(5) . . . . ? C9 C10 C13 O4 179.6(5) . . . . ? O3 C10 C13 O4 0.4(8) . . . . ? O4 C13 C14 S2 -179.2(4) . . . . ? C10 C13 C14 S2 0.8(6) . . . . ? O4 C13 C14 Br2 -0.1(8) . . . . ? C10 C13 C14 Br2 179.9(4) . . . . ? C1 C2 O1 C3 -174.7(7) . . . . ? C5 C2 O1 C3 4.6(9) . . . . ? C4 C3 O1 C2 -12.1(13) . . . . ? C6 C5 O2 C4 -179.0(6) . . . . ? C2 C5 O2 C4 1.6(8) . . . . ? C3 C4 O2 C5 -9.1(11) . . . . ? C12 C11 O3 C10 17.0(12) . . . . ? C9 C10 O3 C11 174.6(6) . . . . ? C13 C10 O3 C11 -6.2(8) . . . . ? C14 C13 O4 C12 175.3(7) . . . . ? C10 C13 O4 C12 -4.7(8) . . . . ? C11 C12 O4 C13 15.3(12) . . . . ? C2 C1 S1 C6 0.7(4) . . . . ? Br1 C1 S1 C6 -178.2(3) . . . . ? C5 C6 S1 C1 -0.4(4) . . . . ? Si1 C6 S1 C1 -174.6(3) . . . . ? C13 C14 S2 C9 -0.8(5) . . . . ? Br2 C14 S2 C9 -179.9(4) . . . . ? C10 C9 S2 C14 0.6(4) . . . . ? Si1 C9 S2 C14 176.7(4) . . . . ? C10 C9 Si1 C8 -59.2(6) . . . . ? S2 C9 Si1 C8 125.3(4) . . . . ? C10 C9 Si1 C7 63.4(6) . . . . ? S2 C9 Si1 C7 -112.0(4) . . . . ? C10 C9 Si1 C6 179.0(5) . . . . ? S2 C9 Si1 C6 3.5(4) . . . . ? C5 C6 Si1 C8 -39.0(6) . . . . ? S1 C6 Si1 C8 133.6(4) . . . . ? C5 C6 Si1 C7 -163.4(5) . . . . ? S1 C6 Si1 C7 9.2(4) . . . . ? C5 C6 Si1 C9 81.2(6) . . . . ? S1 C6 Si1 C9 -106.2(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.511 _refine_diff_density_min -0.458 _refine_diff_density_rms 0.074 _database_code_depnum_ccdc_archive 'CCDC 943875' ####################################################################### # # 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_130311xjb_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H13 I2 O4 P S2' _chemical_formula_weight 642.17 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.6939(12) _cell_length_b 9.2288(7) _cell_length_c 15.8097(12) _cell_angle_alpha 90.00 _cell_angle_beta 104.9240(10) _cell_angle_gamma 90.00 _cell_volume 2071.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 26.50 _exptl_crystal_description block _exptl_crystal_colour ? _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.059 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1224 _exptl_absorpt_coefficient_mu 3.336 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4149 _exptl_absorpt_correction_T_max 0.4552 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13288 _diffrn_reflns_av_R_equivalents 0.0232 _diffrn_reflns_av_sigmaI/netI 0.0243 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.43 _diffrn_reflns_theta_max 26.50 _reflns_number_total 4288 _reflns_number_gt 3664 _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^)+(0.0182P)^2^+2.8612P] 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 SHELXL _refine_ls_extinction_coef 0.00017(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4288 _refine_ls_number_parameters 245 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.0321 _refine_ls_R_factor_gt 0.0253 _refine_ls_wR_factor_ref 0.0564 _refine_ls_wR_factor_gt 0.0532 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.047 _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 C1 C 0.1784(2) 0.6761(4) 0.6656(2) 0.0387(8) Uani 1 1 d . . . H1 H 0.1279 0.7335 0.6369 0.046 Uiso 1 1 calc R . . C2 C 0.1996(3) 0.6632(4) 0.7556(2) 0.0484(9) Uani 1 1 d . . . H2 H 0.1646 0.7140 0.7871 0.058 Uiso 1 1 calc R . . C3 C 0.2724(3) 0.5753(5) 0.7987(2) 0.0546(10) Uani 1 1 d . . . H3 H 0.2864 0.5658 0.8592 0.066 Uiso 1 1 calc R . . C4 C 0.3244(3) 0.5015(5) 0.7517(3) 0.0568(11) Uani 1 1 d . . . H4 H 0.3735 0.4418 0.7807 0.068 Uiso 1 1 calc R . . C5 C 0.3042(3) 0.5153(4) 0.6613(2) 0.0459(9) Uani 1 1 d . . . H5 H 0.3396 0.4647 0.6301 0.055 Uiso 1 1 calc R . . C6 C 0.2312(2) 0.6047(3) 0.61746(19) 0.0299(6) Uani 1 1 d . . . C7 C 0.1478(2) 0.7881(3) 0.47387(19) 0.0287(6) Uani 1 1 d . . . C8 C 0.0690(2) 0.8203(3) 0.40904(19) 0.0279(6) Uani 1 1 d . . . C9 C 0.0485(2) 0.9712(3) 0.39917(19) 0.0307(7) Uani 1 1 d . . . C10 C 0.1111(2) 1.0532(3) 0.4573(2) 0.0305(7) Uani 1 1 d . . . C11 C -0.0695(3) 0.7756(4) 0.3002(2) 0.0477(9) Uani 1 1 d . . . H11A H -0.1165 0.7803 0.3335 0.057 Uiso 1 1 calc R . . H11B H -0.0926 0.7101 0.2514 0.057 Uiso 1 1 calc R . . C12 C -0.0570(3) 0.9226(4) 0.2660(2) 0.0488(9) Uani 1 1 d . . . H12A H -0.0112 0.9178 0.2314 0.059 Uiso 1 1 calc R . . H12B H -0.1163 0.9552 0.2280 0.059 Uiso 1 1 calc R . . C13 C 0.3134(2) 0.6328(3) 0.4750(2) 0.0295(6) Uani 1 1 d . . . C14 C 0.3396(2) 0.5840(3) 0.4037(2) 0.0315(7) Uani 1 1 d . . . C15 C 0.4297(2) 0.6343(4) 0.3980(2) 0.0367(7) Uani 1 1 d . . . C16 C 0.4709(2) 0.7201(4) 0.4656(2) 0.0371(7) Uani 1 1 d . . . C17 C 0.3314(4) 0.4482(6) 0.2782(3) 0.0842(16) Uani 1 1 d DU . . H17A H 0.3591 0.3547 0.2976 0.101 Uiso 1 1 calc R . . H17B H 0.2842 0.4327 0.2235 0.101 Uiso 1 1 calc R . . C18 C 0.4029(4) 0.5374(8) 0.2606(4) 0.113(2) Uani 1 1 d DU . . H18A H 0.4376 0.4798 0.2280 0.135 Uiso 1 1 calc R . . H18B H 0.3724 0.6149 0.2223 0.135 Uiso 1 1 calc R . . I1 I 0.119684(15) 1.27749(2) 0.463687(14) 0.03635(7) Uani 1 1 d . . . I2 I 0.599817(18) 0.82095(3) 0.48471(2) 0.06186(10) Uani 1 1 d . . . O1 O 0.01720(16) 0.7187(2) 0.35555(14) 0.0382(5) Uani 1 1 d . . . O2 O -0.02546(17) 1.0253(3) 0.33628(15) 0.0443(6) Uani 1 1 d . . . O3 O 0.28467(16) 0.4977(3) 0.34061(15) 0.0462(6) Uani 1 1 d . . . O4 O 0.46791(17) 0.5999(3) 0.33065(16) 0.0545(7) Uani 1 1 d . . . P1 P 0.19944(5) 0.61112(8) 0.49757(5) 0.02781(17) Uani 1 1 d . . . S3 S 0.19616(6) 0.94843(8) 0.52432(5) 0.03287(18) Uani 1 1 d . . . S5 S 0.40217(6) 0.74123(10) 0.53734(6) 0.0398(2) 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 0.0381(18) 0.0425(19) 0.0393(19) 0.0045(15) 0.0169(15) 0.0009(15) C2 0.058(2) 0.054(2) 0.042(2) 0.0014(18) 0.0281(18) -0.0025(19) C3 0.070(3) 0.064(3) 0.0291(19) 0.0099(18) 0.0130(18) -0.006(2) C4 0.060(3) 0.063(3) 0.043(2) 0.0184(19) 0.0040(19) 0.016(2) C5 0.052(2) 0.047(2) 0.042(2) 0.0086(17) 0.0178(17) 0.0170(17) C6 0.0335(16) 0.0274(16) 0.0296(16) 0.0036(13) 0.0096(13) -0.0010(13) C7 0.0322(16) 0.0256(15) 0.0289(16) -0.0017(12) 0.0093(13) -0.0023(12) C8 0.0274(15) 0.0327(16) 0.0247(15) -0.0032(12) 0.0086(12) -0.0024(12) C9 0.0318(16) 0.0337(16) 0.0268(15) 0.0032(13) 0.0082(13) 0.0062(13) C10 0.0346(17) 0.0265(16) 0.0306(16) 0.0027(13) 0.0090(13) 0.0033(13) C11 0.0378(19) 0.054(2) 0.042(2) -0.0014(17) -0.0068(16) -0.0020(17) C12 0.044(2) 0.057(2) 0.0364(19) -0.0006(17) -0.0056(16) 0.0048(17) C13 0.0317(16) 0.0277(15) 0.0291(15) -0.0034(13) 0.0080(13) -0.0001(12) C14 0.0320(16) 0.0335(16) 0.0270(15) -0.0016(13) 0.0038(13) 0.0019(13) C15 0.0345(17) 0.0454(19) 0.0325(17) 0.0010(15) 0.0125(14) 0.0047(15) C16 0.0292(16) 0.0412(18) 0.0426(19) -0.0008(15) 0.0124(14) -0.0028(14) C17 0.079(3) 0.109(4) 0.075(3) -0.055(3) 0.040(3) -0.022(3) C18 0.094(4) 0.183(6) 0.076(3) -0.068(4) 0.049(3) -0.051(4) I1 0.04357(13) 0.02738(11) 0.03664(13) 0.00112(9) 0.00769(9) 0.00385(9) I2 0.03934(15) 0.0759(2) 0.0734(2) -0.01664(15) 0.02001(13) -0.01934(13) O1 0.0377(13) 0.0343(12) 0.0367(13) -0.0075(10) -0.0012(10) -0.0015(10) O2 0.0431(14) 0.0430(13) 0.0385(13) -0.0015(11) -0.0045(11) 0.0119(11) O3 0.0412(14) 0.0602(16) 0.0370(13) -0.0199(12) 0.0098(11) -0.0070(12) O4 0.0411(14) 0.083(2) 0.0446(15) -0.0157(14) 0.0202(12) -0.0021(14) P1 0.0313(4) 0.0234(4) 0.0290(4) -0.0007(3) 0.0081(3) -0.0014(3) S3 0.0352(4) 0.0264(4) 0.0328(4) -0.0001(3) 0.0012(3) -0.0015(3) S5 0.0365(4) 0.0439(5) 0.0405(5) -0.0140(4) 0.0124(4) -0.0075(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 C2 1.380(5) . ? C1 C6 1.386(4) . ? C2 C3 1.375(6) . ? C3 C4 1.375(6) . ? C4 C5 1.389(5) . ? C5 C6 1.388(4) . ? C6 P1 1.833(3) . ? C7 C8 1.367(4) . ? C7 S3 1.743(3) . ? C7 P1 1.799(3) . ? C8 O1 1.357(4) . ? C8 C9 1.425(4) . ? C9 C10 1.352(4) . ? C9 O2 1.365(4) . ? C10 S3 1.714(3) . ? C10 I1 2.075(3) . ? C11 O1 1.446(4) . ? C11 C12 1.490(5) . ? C12 O2 1.443(4) . ? C13 C14 1.359(4) . ? C13 S5 1.736(3) . ? C13 P1 1.811(3) . ? C14 O3 1.366(4) . ? C14 C15 1.427(4) . ? C15 C16 1.343(5) . ? C15 O4 1.363(4) . ? C16 S5 1.712(3) . ? C16 I2 2.062(3) . ? C17 C18 1.418(6) . ? C17 O3 1.414(5) . ? C18 O4 1.388(5) . ? 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 C2 C1 C6 121.0(3) . . ? C3 C2 C1 120.1(3) . . ? C2 C3 C4 119.6(3) . . ? C3 C4 C5 120.6(4) . . ? C4 C5 C6 120.0(3) . . ? C1 C6 C5 118.6(3) . . ? C1 C6 P1 121.5(2) . . ? C5 C6 P1 119.6(2) . . ? C8 C7 S3 109.0(2) . . ? C8 C7 P1 125.7(2) . . ? S3 C7 P1 125.09(18) . . ? O1 C8 C7 123.2(3) . . ? O1 C8 C9 122.5(3) . . ? C7 C8 C9 114.1(3) . . ? C10 C9 O2 124.4(3) . . ? C10 C9 C8 112.6(3) . . ? O2 C9 C8 122.9(3) . . ? C9 C10 S3 111.4(2) . . ? C9 C10 I1 127.9(2) . . ? S3 C10 I1 120.46(17) . . ? O1 C11 C12 112.2(3) . . ? O2 C12 C11 111.3(3) . . ? C14 C13 S5 109.3(2) . . ? C14 C13 P1 127.0(2) . . ? S5 C13 P1 123.33(17) . . ? C13 C14 O3 123.9(3) . . ? C13 C14 C15 114.2(3) . . ? O3 C14 C15 121.9(3) . . ? C16 C15 O4 124.6(3) . . ? C16 C15 C14 112.2(3) . . ? O4 C15 C14 123.3(3) . . ? C15 C16 S5 111.9(2) . . ? C15 C16 I2 126.2(2) . . ? S5 C16 I2 121.88(19) . . ? C18 C17 O3 117.9(4) . . ? O4 C18 C17 118.5(4) . . ? C8 O1 C11 113.1(2) . . ? C9 O2 C12 111.0(2) . . ? C14 O3 C17 113.3(3) . . ? C15 O4 C18 112.5(3) . . ? C7 P1 C13 102.73(14) . . ? C7 P1 C6 103.08(14) . . ? C13 P1 C6 101.85(14) . . ? C10 S3 C7 92.83(15) . . ? C16 S5 C13 92.49(15) . . ? 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 C6 C1 C2 C3 -1.9(6) . . . . ? C1 C2 C3 C4 0.6(6) . . . . ? C2 C3 C4 C5 0.2(6) . . . . ? C3 C4 C5 C6 0.3(6) . . . . ? C2 C1 C6 C5 2.3(5) . . . . ? C2 C1 C6 P1 176.0(3) . . . . ? C4 C5 C6 C1 -1.4(5) . . . . ? C4 C5 C6 P1 -175.3(3) . . . . ? S3 C7 C8 O1 177.6(2) . . . . ? P1 C7 C8 O1 2.5(4) . . . . ? S3 C7 C8 C9 0.8(3) . . . . ? P1 C7 C8 C9 -174.3(2) . . . . ? O1 C8 C9 C10 -177.6(3) . . . . ? C7 C8 C9 C10 -0.8(4) . . . . ? O1 C8 C9 O2 1.1(5) . . . . ? C7 C8 C9 O2 177.9(3) . . . . ? O2 C9 C10 S3 -178.3(2) . . . . ? C8 C9 C10 S3 0.3(3) . . . . ? O2 C9 C10 I1 -4.4(5) . . . . ? C8 C9 C10 I1 174.3(2) . . . . ? O1 C11 C12 O2 -60.6(4) . . . . ? S5 C13 C14 O3 -178.9(3) . . . . ? P1 C13 C14 O3 -6.3(5) . . . . ? S5 C13 C14 C15 -0.8(4) . . . . ? P1 C13 C14 C15 171.9(2) . . . . ? C13 C14 C15 C16 0.4(4) . . . . ? O3 C14 C15 C16 178.6(3) . . . . ? C13 C14 C15 O4 -178.7(3) . . . . ? O3 C14 C15 O4 -0.5(5) . . . . ? O4 C15 C16 S5 179.3(3) . . . . ? C14 C15 C16 S5 0.2(4) . . . . ? O4 C15 C16 I2 0.2(5) . . . . ? C14 C15 C16 I2 -178.8(2) . . . . ? O3 C17 C18 O4 44.3(9) . . . . ? C7 C8 O1 C11 172.1(3) . . . . ? C9 C8 O1 C11 -11.4(4) . . . . ? C12 C11 O1 C8 40.0(4) . . . . ? C10 C9 O2 C12 158.3(3) . . . . ? C8 C9 O2 C12 -20.2(4) . . . . ? C11 C12 O2 C9 48.3(4) . . . . ? C13 C14 O3 C17 -173.4(4) . . . . ? C15 C14 O3 C17 8.5(5) . . . . ? C18 C17 O3 C14 -29.2(7) . . . . ? C16 C15 O4 C18 -166.5(5) . . . . ? C14 C15 O4 C18 12.5(6) . . . . ? C17 C18 O4 C15 -33.5(8) . . . . ? C8 C7 P1 C13 116.0(3) . . . . ? S3 C7 P1 C13 -58.3(2) . . . . ? C8 C7 P1 C6 -138.4(3) . . . . ? S3 C7 P1 C6 47.2(2) . . . . ? C14 C13 P1 C7 -104.1(3) . . . . ? S5 C13 P1 C7 67.6(2) . . . . ? C14 C13 P1 C6 149.3(3) . . . . ? S5 C13 P1 C6 -39.0(2) . . . . ? C1 C6 P1 C7 32.3(3) . . . . ? C5 C6 P1 C7 -154.0(3) . . . . ? C1 C6 P1 C13 138.6(3) . . . . ? C5 C6 P1 C13 -47.8(3) . . . . ? C9 C10 S3 C7 0.1(3) . . . . ? I1 C10 S3 C7 -174.37(18) . . . . ? C8 C7 S3 C10 -0.5(2) . . . . ? P1 C7 S3 C10 174.6(2) . . . . ? C15 C16 S5 C13 -0.6(3) . . . . ? I2 C16 S5 C13 178.5(2) . . . . ? C14 C13 S5 C16 0.8(3) . . . . ? P1 C13 S5 C16 -172.2(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.920 _refine_diff_density_min -0.897 _refine_diff_density_rms 0.081 _database_code_depnum_ccdc_archive 'CCDC 943876' ####################################################################### # # 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_xjb1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H14 I2 O4 S2 Si' _chemical_formula_weight 592.26 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' Si Si 0.0817 0.0704 '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 Orthorhombic _symmetry_space_group_name_H-M Iba2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'x+1, -y+1, z+1/2' '-x+1, y+1, z+1/2' _cell_length_a 16.903(8) _cell_length_b 28.697(13) _cell_length_c 8.005(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3883(3) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3850 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 26.00 _exptl_crystal_description BLOCK _exptl_crystal_colour ? _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 2.026 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2256 _exptl_absorpt_coefficient_mu 3.530 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4275 _exptl_absorpt_correction_T_max 0.5387 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 11749 _diffrn_reflns_av_R_equivalents 0.0355 _diffrn_reflns_av_sigmaI/netI 0.0377 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.40 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3775 _reflns_number_gt 3177 _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^)+(0.1095P)^2^+54.3190P] 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 0.00 _refine_ls_number_reflns 3775 _refine_ls_number_parameters 210 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0854 _refine_ls_R_factor_gt 0.0741 _refine_ls_wR_factor_ref 0.2056 _refine_ls_wR_factor_gt 0.1931 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.052 _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 0.84027(6) 0.68428(3) 0.8444(2) 0.0817(5) Uani 1 1 d . . . I2 I 0.63172(7) 0.97065(4) 1.39876(17) 0.0766(4) Uani 1 1 d . . . Si1 Si 0.86420(15) 0.90207(10) 0.8451(5) 0.0439(7) Uani 1 1 d . . . S1 S 0.81454(14) 0.79768(9) 0.8516(4) 0.0443(6) Uani 1 1 d . . . S2 S 0.7839(2) 0.94091(11) 1.1660(5) 0.0540(8) Uani 1 1 d . . . C4 C 0.8880(6) 0.8391(4) 0.8503(16) 0.042(2) Uani 1 1 d . . . C1 C 0.8802(6) 0.7523(4) 0.8470(16) 0.044(3) Uani 1 1 d . . . C3 C 0.9612(6) 0.8171(4) 0.8472(14) 0.037(2) Uani 1 1 d . . . C2 C 0.9549(6) 0.7674(4) 0.8439(15) 0.042(2) Uani 1 1 d . . . O2 O 1.0198(4) 0.7392(3) 0.8420(14) 0.059(2) Uani 1 1 d . . . O1 O 1.0308(4) 0.8398(3) 0.8451(14) 0.056(2) Uani 1 1 d . . . C6 C 1.0961(9) 0.8121(5) 0.859(5) 0.142(14) Uani 1 1 d D . . H6A H 1.1161 0.8154 0.9722 0.171 Uiso 1 1 calc R . . H6B H 1.1363 0.8244 0.7849 0.171 Uiso 1 1 calc R . . C5 C 1.0885(8) 0.7621(5) 0.825(4) 0.111(9) Uani 1 1 d D . . H5A H 1.1056 0.7574 0.7103 0.134 Uiso 1 1 calc R . . H5B H 1.1267 0.7464 0.8952 0.134 Uiso 1 1 calc R . . C9 C 0.7758(7) 0.9119(4) 0.9795(17) 0.046(3) Uani 1 1 d . . . C7 C 0.8361(11) 0.9172(7) 0.624(2) 0.074(4) Uani 1 1 d . . . H7A H 0.8826 0.9174 0.5554 0.111 Uiso 1 1 calc R . . H7B H 0.8119 0.9475 0.6220 0.111 Uiso 1 1 calc R . . H7C H 0.7994 0.8945 0.5823 0.111 Uiso 1 1 calc R . . C8 C 0.9480(9) 0.9368(6) 0.917(4) 0.095(7) Uani 1 1 d . . . H8A H 0.9938 0.9295 0.8510 0.143 Uiso 1 1 calc R . . H8B H 0.9586 0.9297 1.0322 0.143 Uiso 1 1 calc R . . H8C H 0.9357 0.9693 0.9061 0.143 Uiso 1 1 calc R . . C10 C 0.6982(7) 0.8990(5) 0.9452(12) 0.045(3) Uani 1 1 d . . . C11 C 0.6467(7) 0.9147(4) 1.074(2) 0.053(3) Uani 1 1 d . . . C12 C 0.6832(8) 0.9380(4) 1.2035(17) 0.049(3) Uani 1 1 d . . . O3 O 0.6760(5) 0.8758(4) 0.8168(14) 0.069(3) Uani 1 1 d . . . O4 O 0.5675(5) 0.9085(3) 1.0725(13) 0.056(2) Uani 1 1 d . . . C14 C 0.5478(11) 0.8754(8) 0.941(2) 0.095(7) Uani 1 1 d . . . H14A H 0.5511 0.8443 0.9881 0.114 Uiso 1 1 calc R . . H14B H 0.4930 0.8805 0.9098 0.114 Uiso 1 1 calc R . . C13 C 0.5921(9) 0.8759(9) 0.797(2) 0.094(7) Uani 1 1 d . . . H13A H 0.5776 0.9034 0.7337 0.112 Uiso 1 1 calc R . . H13B H 0.5775 0.8490 0.7310 0.112 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 0.0526(5) 0.0420(4) 0.1506(12) -0.0034(6) -0.0079(7) 0.0056(3) I2 0.0844(7) 0.0653(6) 0.0801(7) -0.0258(5) 0.0123(6) 0.0014(5) Si1 0.0296(13) 0.0402(15) 0.062(2) 0.0005(14) 0.0012(16) 0.0023(10) S1 0.0290(11) 0.0416(12) 0.0623(18) -0.0028(13) -0.0014(13) 0.0066(9) S2 0.0456(17) 0.0515(18) 0.065(2) -0.0104(15) -0.0120(15) -0.0033(13) C4 0.027(4) 0.043(5) 0.055(7) -0.009(5) -0.004(5) 0.008(4) C1 0.041(5) 0.043(6) 0.050(7) 0.006(5) -0.001(6) 0.014(4) C3 0.030(4) 0.052(5) 0.027(5) 0.002(5) 0.002(5) 0.010(4) C2 0.033(5) 0.052(6) 0.041(6) 0.005(5) 0.002(5) 0.013(4) O2 0.035(4) 0.057(5) 0.086(7) 0.002(5) 0.003(5) 0.019(3) O1 0.027(3) 0.065(5) 0.076(6) 0.008(5) -0.009(4) 0.002(3) C6 0.034(7) 0.074(11) 0.32(4) 0.03(2) 0.03(2) 0.015(7) C5 0.040(7) 0.088(11) 0.21(3) 0.026(16) 0.010(13) 0.030(8) C9 0.030(5) 0.047(6) 0.061(7) 0.004(5) -0.008(5) 0.003(5) C7 0.070(10) 0.084(12) 0.069(9) -0.002(8) -0.002(8) 0.016(8) C8 0.042(7) 0.077(10) 0.17(2) -0.034(13) 0.008(11) -0.004(7) C10 0.043(6) 0.070(8) 0.021(5) -0.001(5) -0.007(4) 0.021(6) C11 0.028(5) 0.031(6) 0.099(11) 0.010(6) -0.006(6) 0.000(4) C12 0.052(7) 0.039(6) 0.054(7) -0.008(5) 0.002(6) -0.002(5) O3 0.040(4) 0.083(6) 0.083(7) -0.042(6) -0.010(5) 0.006(4) O4 0.030(4) 0.062(5) 0.075(6) -0.014(5) -0.002(4) 0.004(4) C14 0.073(11) 0.122(15) 0.089(14) -0.057(12) -0.017(10) -0.009(11) C13 0.050(8) 0.162(18) 0.068(11) -0.053(12) 0.017(8) -0.039(10) _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 2.066(11) . ? I2 C12 2.019(13) . ? Si1 C8 1.825(16) . ? Si1 C4 1.851(11) . ? Si1 C9 1.862(13) . ? Si1 C7 1.882(19) . ? S1 C1 1.712(10) . ? S1 C4 1.719(11) . ? S2 C9 1.716(14) . ? S2 C12 1.731(14) . ? C4 C3 1.389(13) . ? C1 C2 1.335(16) . ? C3 O1 1.346(13) . ? C3 C2 1.430(15) . ? C2 O2 1.365(12) . ? O2 C5 1.341(18) . ? O1 C6 1.365(17) . ? C6 C5 1.466(10) . ? C9 C10 1.390(17) . ? C10 O3 1.282(15) . ? C10 C11 1.423(19) . ? C11 O4 1.350(14) . ? C11 C12 1.38(2) . ? O3 C13 1.427(19) . ? O4 C14 1.458(18) . ? C14 C13 1.37(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 Si1 C4 110.9(7) . . ? C8 Si1 C9 110.9(8) . . ? C4 Si1 C9 108.0(5) . . ? C8 Si1 C7 111.5(11) . . ? C4 Si1 C7 107.6(7) . . ? C9 Si1 C7 107.8(7) . . ? C1 S1 C4 93.3(5) . . ? C9 S2 C12 92.8(6) . . ? C3 C4 S1 109.2(8) . . ? C3 C4 Si1 129.5(8) . . ? S1 C4 Si1 121.2(5) . . ? C2 C1 S1 111.5(8) . . ? C2 C1 I1 128.0(8) . . ? S1 C1 I1 120.5(6) . . ? O1 C3 C4 124.0(10) . . ? O1 C3 C2 123.2(9) . . ? C4 C3 C2 112.8(9) . . ? C1 C2 O2 124.6(10) . . ? C1 C2 C3 113.2(9) . . ? O2 C2 C3 122.2(10) . . ? C5 O2 C2 113.9(9) . . ? C3 O1 C6 115.1(10) . . ? O1 C6 C5 118.9(15) . . ? O2 C5 C6 122.4(13) . . ? C10 C9 S2 112.1(9) . . ? C10 C9 Si1 127.1(10) . . ? S2 C9 Si1 120.8(7) . . ? O3 C10 C9 124.9(11) . . ? O3 C10 C11 124.5(12) . . ? C9 C10 C11 110.6(11) . . ? O4 C11 C12 120.9(13) . . ? O4 C11 C10 124.0(13) . . ? C12 C11 C10 115.1(11) . . ? C11 C12 S2 109.5(10) . . ? C11 C12 I2 127.9(10) . . ? S2 C12 I2 122.4(7) . . ? C10 O3 C13 112.2(11) . . ? C11 O4 C14 108.5(12) . . ? C13 C14 O4 118.3(17) . . ? C14 C13 O3 116.8(16) . . ? 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 C1 S1 C4 C3 -0.3(10) . . . . ? C1 S1 C4 Si1 177.4(8) . . . . ? C8 Si1 C4 C3 -22.7(16) . . . . ? C9 Si1 C4 C3 -144.5(12) . . . . ? C7 Si1 C4 C3 99.5(13) . . . . ? C8 Si1 C4 S1 160.1(11) . . . . ? C9 Si1 C4 S1 38.3(10) . . . . ? C7 Si1 C4 S1 -77.7(10) . . . . ? C4 S1 C1 C2 -0.2(11) . . . . ? C4 S1 C1 I1 -179.6(8) . . . . ? S1 C4 C3 O1 179.8(10) . . . . ? Si1 C4 C3 O1 2(2) . . . . ? S1 C4 C3 C2 0.7(14) . . . . ? Si1 C4 C3 C2 -176.7(9) . . . . ? S1 C1 C2 O2 179.1(11) . . . . ? I1 C1 C2 O2 -2(2) . . . . ? S1 C1 C2 C3 0.7(14) . . . . ? I1 C1 C2 C3 -179.9(9) . . . . ? O1 C3 C2 C1 180.0(12) . . . . ? C4 C3 C2 C1 -0.9(16) . . . . ? O1 C3 C2 O2 1.5(19) . . . . ? C4 C3 C2 O2 -179.4(12) . . . . ? C1 C2 O2 C5 174.6(19) . . . . ? C3 C2 O2 C5 -7(2) . . . . ? C4 C3 O1 C6 174(2) . . . . ? C2 C3 O1 C6 -7(3) . . . . ? C3 O1 C6 C5 18(4) . . . . ? C2 O2 C5 C6 19(4) . . . . ? O1 C6 C5 O2 -26(5) . . . . ? C12 S2 C9 C10 -1.2(10) . . . . ? C12 S2 C9 Si1 177.2(8) . . . . ? C8 Si1 C9 C10 166.4(13) . . . . ? C4 Si1 C9 C10 -71.9(13) . . . . ? C7 Si1 C9 C10 44.0(14) . . . . ? C8 Si1 C9 S2 -11.8(12) . . . . ? C4 Si1 C9 S2 109.9(8) . . . . ? C7 Si1 C9 S2 -134.1(9) . . . . ? S2 C9 C10 O3 -177.8(11) . . . . ? Si1 C9 C10 O3 4(2) . . . . ? S2 C9 C10 C11 1.4(14) . . . . ? Si1 C9 C10 C11 -176.9(10) . . . . ? O3 C10 C11 O4 -3(2) . . . . ? C9 C10 C11 O4 178.0(12) . . . . ? O3 C10 C11 C12 178.2(12) . . . . ? C9 C10 C11 C12 -1.0(16) . . . . ? O4 C11 C12 S2 -178.9(10) . . . . ? C10 C11 C12 S2 0.1(14) . . . . ? O4 C11 C12 I2 -4.8(18) . . . . ? C10 C11 C12 I2 174.1(10) . . . . ? C9 S2 C12 C11 0.6(10) . . . . ? C9 S2 C12 I2 -173.8(8) . . . . ? C9 C10 O3 C13 -168.1(16) . . . . ? C11 C10 O3 C13 13(2) . . . . ? C12 C11 O4 C14 -168.9(15) . . . . ? C10 C11 O4 C14 12(2) . . . . ? C11 O4 C14 C13 -35(3) . . . . ? O4 C14 C13 O3 49(3) . . . . ? C10 O3 C13 C14 -35(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 4.556 _refine_diff_density_min -0.914 _refine_diff_density_rms 0.196 _database_code_depnum_ccdc_archive 'CCDC 943877'