# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_sc0930 _database_code_depnum_ccdc_archive 'CCDC 875779' #TrackingRef '1_Ge-BT.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C32 H22 Ge S2' _chemical_formula_moiety 'C32 H22 Ge S2' _chemical_formula_weight 543.24 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,+Y,1/2-Z 3 -X,-Y,-Z 4 +X,-Y,1/2+Z 5 1/2+X,1/2+Y,+Z 6 1/2-X,1/2+Y,1/2-Z 7 1/2-X,1/2-Y,-Z 8 1/2+X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 19.822(7) _cell_length_b 20.141(7) _cell_length_c 6.596(3) _cell_angle_alpha 90.0000 _cell_angle_beta 102.289(5) _cell_angle_gamma 90.0000 _cell_volume 2573.0(18) _cell_formula_units_Z 4 _cell_measurement_reflns_used 3960 _cell_measurement_theta_min 3.20 _cell_measurement_theta_max 27.60 _cell_measurement_temperature 153 #------------------------------------------------------------------------------ _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.210 _exptl_crystal_size_mid 0.020 _exptl_crystal_size_min 0.020 _exptl_crystal_density_diffrn 1.402 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1112.00 _exptl_absorpt_coefficient_mu 1.371 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_correction_T_min 0.767 _exptl_absorpt_correction_T_max 0.973 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 153 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku Saturn724' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.111 _diffrn_reflns_number 15108 _diffrn_reflns_av_R_equivalents 0.0630 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2948 _reflns_number_gt 2209 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1065 _refine_ls_number_restraints 142 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 2948 _refine_ls_number_parameters 159 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0548P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.430 _refine_diff_density_min -0.910 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; Ge Ge 0.1547 1.8001 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; S S 0.1246 0.1234 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 Ge1 Ge 0.0000 0.186818(19) 0.2500 0.03072(14) Uani 1.0 4 d . . . S1 S 0.05240(3) 0.38087(3) 0.51764(11) 0.03336(18) Uani 1.0 8 d . . . C1 C 0.02101(13) 0.31611(12) 0.3552(4) 0.0285(6) Uani 1.0 8 d . . . C2 C 0.03902(13) 0.25526(13) 0.4479(4) 0.0316(6) Uani 1.0 8 d . . . C3 C 0.07890(14) 0.26201(14) 0.6513(5) 0.0335(6) Uani 1.0 8 d . . . C4 C 0.09087(14) 0.32651(14) 0.7135(4) 0.0323(6) Uani 1.0 8 d . . . C5 C 0.13089(14) 0.35162(15) 0.9122(5) 0.0364(7) Uani 1.0 8 d . . . C6 C 0.17364(19) 0.30889(18) 1.0478(5) 0.0542(9) Uani 1.0 8 d . . . C7 C 0.2126(2) 0.3321(2) 1.2344(6) 0.0670(11) Uani 1.0 8 d . . . C8 C 0.2104(2) 0.3982(3) 1.2862(6) 0.0662(11) Uani 1.0 8 d . . . C9 C 0.16875(17) 0.4410(2) 1.1547(6) 0.0564(9) Uani 1.0 8 d . . . C10 C 0.12838(16) 0.41788(16) 0.9695(5) 0.0439(8) Uani 1.0 8 d . . . C11 C 0.06933(14) 0.13235(13) 0.1613(5) 0.0325(6) Uani 1.0 8 d . . . C12 C 0.13917(15) 0.14393(16) 0.2312(5) 0.0440(8) Uani 1.0 8 d . . . C13 C 0.18778(18) 0.1055(2) 0.1577(6) 0.0576(9) Uani 1.0 8 d . . . C14 C 0.16682(19) 0.05626(19) 0.0174(6) 0.0579(9) Uani 1.0 8 d . . . C15 C 0.0979(2) 0.04416(19) -0.0548(6) 0.0646(10) Uani 1.0 8 d . . . C16 C 0.04919(18) 0.08234(16) 0.0182(6) 0.0523(9) Uani 1.0 8 d . . . H3 H 0.0959 0.2252 0.7370 0.0402 Uiso 1.0 8 d . . . H6 H 0.1762 0.2634 1.0122 0.0650 Uiso 1.0 8 d . . . H7 H 0.2409 0.3022 1.3268 0.0804 Uiso 1.0 8 d . . . H8 H 0.2377 0.4141 1.4131 0.0794 Uiso 1.0 8 d . . . H9 H 0.1674 0.4867 1.1900 0.0677 Uiso 1.0 8 d . . . H10 H 0.0987 0.4477 0.8809 0.0527 Uiso 1.0 8 d . . . H12 H 0.1543 0.1781 0.3296 0.0527 Uiso 1.0 8 d . . . H13 H 0.2357 0.1139 0.2062 0.0692 Uiso 1.0 8 d . . . H14 H 0.2001 0.0302 -0.0308 0.0695 Uiso 1.0 8 d . . . H15 H 0.0833 0.0100 -0.1538 0.0775 Uiso 1.0 8 d . . . H16 H 0.0014 0.0737 -0.0316 0.0628 Uiso 1.0 8 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Ge1 0.0294(3) 0.0279(3) 0.0329(3) 0.0000 0.00230(17) 0.0000 S1 0.0339(4) 0.0315(4) 0.0344(4) -0.0035(3) 0.0067(3) -0.0028(3) C1 0.0265(14) 0.0309(13) 0.0286(14) -0.0026(11) 0.0067(11) -0.0022(11) C2 0.0299(14) 0.0313(13) 0.0346(14) -0.0032(11) 0.0091(12) -0.0020(12) C3 0.0310(14) 0.0376(14) 0.0309(14) -0.0030(12) 0.0043(12) 0.0022(12) C4 0.0268(14) 0.0411(15) 0.0294(14) -0.0047(11) 0.0070(12) 0.0003(11) C5 0.0327(15) 0.0477(17) 0.0301(14) -0.0118(12) 0.0096(12) -0.0035(12) C6 0.061(3) 0.057(2) 0.0384(17) -0.0139(17) -0.0040(15) 0.0021(15) C7 0.074(3) 0.078(3) 0.0379(18) -0.021(2) -0.0131(18) 0.0069(18) C8 0.068(3) 0.091(3) 0.0356(19) -0.032(2) 0.0025(17) -0.0108(18) C9 0.051(2) 0.071(3) 0.049(2) -0.0222(17) 0.0168(16) -0.0260(17) C10 0.0362(17) 0.0551(19) 0.0429(17) -0.0106(13) 0.0139(14) -0.0108(14) C11 0.0334(14) 0.0313(13) 0.0332(14) 0.0007(11) 0.0080(12) 0.0050(11) C12 0.0349(16) 0.0529(19) 0.0436(17) -0.0018(13) 0.0071(14) 0.0018(14) C13 0.0350(18) 0.080(3) 0.061(3) 0.0100(17) 0.0158(16) 0.0161(19) C14 0.059(2) 0.061(3) 0.061(3) 0.0215(18) 0.0310(18) 0.0109(18) C15 0.072(3) 0.058(3) 0.070(3) 0.0083(19) 0.028(2) -0.0174(19) C16 0.0459(19) 0.0490(19) 0.063(3) 0.0003(15) 0.0136(17) -0.0158(16) #============================================================================== _computing_data_collection 'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r4' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r4' _computing_structure_solution 'Il Milione (Burla, et al., 2007)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 Ge1 C2 1.942(3) yes . . Ge1 C2 1.942(3) yes . 2_555 Ge1 C11 1.943(3) yes . . Ge1 C11 1.943(3) yes . 2_555 S1 C1 1.718(3) yes . . S1 C4 1.741(3) yes . . C1 C1 1.458(4) yes . 2_555 C1 C2 1.382(4) yes . . C2 C3 1.411(4) yes . . C3 C4 1.368(4) yes . . C4 C5 1.470(4) yes . . C5 C6 1.391(5) yes . . C5 C10 1.391(5) yes . . C6 C7 1.387(5) yes . . C7 C8 1.379(6) yes . . C8 C9 1.368(6) yes . . C9 C10 1.391(5) yes . . C11 C12 1.383(4) yes . . C11 C16 1.380(5) yes . . C12 C13 1.401(6) yes . . C13 C14 1.360(6) yes . . C14 C15 1.370(6) yes . . C15 C16 1.397(6) yes . . C3 H3 0.950(3) no . . C6 H6 0.950(4) no . . C7 H7 0.950(4) no . . C8 H8 0.950(4) no . . C9 H9 0.950(4) no . . C10 H10 0.950(3) no . . C12 H12 0.950(3) no . . C13 H13 0.950(4) no . . C14 H14 0.950(4) no . . C15 H15 0.950(4) no . . C16 H16 0.950(4) no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C2 Ge1 C2 89.57(11) yes . . 2_555 C2 Ge1 C11 113.39(11) yes . . . C2 Ge1 C11 113.86(12) yes . . 2_555 C2 Ge1 C11 113.86(12) yes 2_555 . . C2 Ge1 C11 113.39(11) yes 2_555 . 2_555 C11 Ge1 C11 111.26(12) yes . . 2_555 C1 S1 C4 91.64(13) yes . . . S1 C1 C1 130.61(19) yes . . 2_555 S1 C1 C2 111.84(19) yes . . . C1 C1 C2 117.5(3) yes 2_555 . . Ge1 C2 C1 107.68(18) yes . . . Ge1 C2 C3 140.3(2) yes . . . C1 C2 C3 112.0(3) yes . . . C2 C3 C4 113.8(3) yes . . . S1 C4 C3 110.74(19) yes . . . S1 C4 C5 120.9(3) yes . . . C3 C4 C5 128.4(3) yes . . . C4 C5 C6 120.0(3) yes . . . C4 C5 C10 121.9(3) yes . . . C6 C5 C10 118.1(3) yes . . . C5 C6 C7 120.7(4) yes . . . C6 C7 C8 120.3(4) yes . . . C7 C8 C9 119.9(4) yes . . . C8 C9 C10 120.2(4) yes . . . C5 C10 C9 120.9(3) yes . . . Ge1 C11 C12 121.8(3) yes . . . Ge1 C11 C16 119.9(3) yes . . . C12 C11 C16 118.3(3) yes . . . C11 C12 C13 120.3(3) yes . . . C12 C13 C14 120.4(4) yes . . . C13 C14 C15 120.3(4) yes . . . C14 C15 C16 119.6(4) yes . . . C11 C16 C15 121.1(3) yes . . . C2 C3 H3 123.1(3) no . . . C4 C3 H3 123.1(3) no . . . C5 C6 H6 119.7(3) no . . . C7 C6 H6 119.7(4) no . . . C6 C7 H7 119.9(4) no . . . C8 C7 H7 119.9(4) no . . . C7 C8 H8 120.1(4) no . . . C9 C8 H8 120.1(5) no . . . C8 C9 H9 119.9(4) no . . . C10 C9 H9 119.9(4) no . . . C5 C10 H10 119.6(3) no . . . C9 C10 H10 119.6(4) no . . . C11 C12 H12 119.8(3) no . . . C13 C12 H12 119.8(3) no . . . C12 C13 H13 119.8(4) no . . . C14 C13 H13 119.8(4) no . . . C13 C14 H14 119.9(4) no . . . C15 C14 H14 119.9(4) no . . . C14 C15 H15 120.2(4) no . . . C16 C15 H15 120.2(4) no . . . C11 C16 H16 119.4(4) no . . . C15 C16 H16 119.4(4) no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C2 Ge1 C2 C1 -0.22(17) no . . 2_555 2_555 C2 Ge1 C2 C3 179.7(3) no . . 2_555 2_555 C2 Ge1 C2 C1 -0.22(17) no 2_555 . . . C2 Ge1 C2 C3 179.7(3) no 2_555 . . . C2 Ge1 C11 C12 -1.7(3) no . . . . C2 Ge1 C11 C16 -178.94(17) no . . . . C11 Ge1 C2 C1 115.72(17) no . . . . C11 Ge1 C2 C3 -64.3(4) no . . . . C2 Ge1 C11 C12 98.8(2) no . . 2_555 2_555 C2 Ge1 C11 C16 -78.4(2) no . . 2_555 2_555 C11 Ge1 C2 C1 -115.73(17) no 2_555 . . . C11 Ge1 C2 C3 64.2(3) no 2_555 . . . C2 Ge1 C11 C12 98.8(2) no 2_555 . . . C2 Ge1 C11 C16 -78.4(2) no 2_555 . . . C11 Ge1 C2 C1 -115.73(17) no . . 2_555 2_555 C11 Ge1 C2 C3 64.2(3) no . . 2_555 2_555 C2 Ge1 C11 C12 -1.7(3) no 2_555 . 2_555 2_555 C2 Ge1 C11 C16 -178.94(17) no 2_555 . 2_555 2_555 C11 Ge1 C2 C1 115.72(17) no 2_555 . 2_555 2_555 C11 Ge1 C2 C3 -64.3(4) no 2_555 . 2_555 2_555 C11 Ge1 C11 C12 -131.60(19) no . . 2_555 2_555 C11 Ge1 C11 C16 51.2(3) no . . 2_555 2_555 C11 Ge1 C11 C12 -131.60(19) no 2_555 . . . C11 Ge1 C11 C16 51.2(3) no 2_555 . . . C1 S1 C4 C3 -0.1(2) no . . . . C1 S1 C4 C5 178.8(3) no . . . . C4 S1 C1 C1 179.1(3) no . . . 2_555 C4 S1 C1 C2 0.3(2) no . . . . S1 C1 C1 S1 1.7(5) no . . 2_555 2_555 S1 C1 C1 C2 -179.57(19) no . . 2_555 2_555 S1 C1 C2 Ge1 179.55(14) no . . . . S1 C1 C2 C3 -0.4(3) no . . . . C1 C1 C2 Ge1 0.6(4) no 2_555 . . . C1 C1 C2 C3 -179.3(3) no 2_555 . . . C2 C1 C1 S1 -179.6(3) no . . 2_555 2_555 C2 C1 C1 C2 -0.9(4) no . . 2_555 2_555 Ge1 C2 C3 C4 -179.6(3) no . . . . C1 C2 C3 C4 0.3(4) no . . . . C2 C3 C4 S1 -0.1(4) no . . . . C2 C3 C4 C5 -179.0(3) no . . . . S1 C4 C5 C6 -165.69(19) no . . . . S1 C4 C5 C10 13.3(4) no . . . . C3 C4 C5 C6 13.1(5) no . . . . C3 C4 C5 C10 -167.9(3) no . . . . C4 C5 C6 C7 178.9(3) no . . . . C4 C5 C10 C9 -177.5(3) no . . . . C6 C5 C10 C9 1.5(5) no . . . . C10 C5 C6 C7 -0.1(5) no . . . . C5 C6 C7 C8 -1.2(6) no . . . . C6 C7 C8 C9 1.1(6) no . . . . C7 C8 C9 C10 0.4(6) no . . . . C8 C9 C10 C5 -1.7(6) no . . . . Ge1 C11 C12 C13 -177.36(18) no . . . . Ge1 C11 C16 C15 177.4(2) no . . . . C12 C11 C16 C15 0.1(5) no . . . . C16 C11 C12 C13 -0.1(5) no . . . . C11 C12 C13 C14 -0.2(5) no . . . . C12 C13 C14 C15 0.5(6) no . . . . C13 C14 C15 C16 -0.6(6) no . . . . C14 C15 C16 C11 0.3(6) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 Ge1 C1 2.704(3) no . 2_555 Ge1 C3 3.159(3) no . 2_555 Ge1 C12 2.918(4) no . 2_555 Ge1 C16 2.890(4) no . 2_555 S1 C10 3.130(4) no . . C2 C12 3.496(5) no . . C3 C6 3.028(5) no . . C5 C8 2.792(5) no . . C6 C9 2.760(6) no . . C7 C10 2.754(5) no . . C11 C14 2.787(5) no . . C12 C15 2.759(5) no . . C13 C16 2.745(5) no . . C8 C14 3.585(6) no . 7_556 C14 C8 3.585(6) no . 7_556 Ge1 H3 3.4536(13) no . . Ge1 H3 3.4536(13) no . 2_555 Ge1 H12 2.9956(11) no . . Ge1 H12 2.9956(11) no . 2_555 Ge1 H16 2.9429(9) no . . Ge1 H16 2.9429(9) no . 2_555 S1 H3 3.4841(12) no . . S1 H10 2.7315(12) no . . C1 H3 3.211(3) no . . C2 H12 3.000(3) no . . C3 H6 2.726(3) no . . C3 H12 3.307(3) no . . C4 H6 2.634(3) no . . C4 H10 2.671(3) no . . C5 H3 2.822(3) no . . C5 H7 3.269(3) no . . C5 H9 3.273(3) no . . C6 H3 2.842(4) no . . C6 H8 3.257(4) no . . C6 H10 3.247(4) no . . C7 H9 3.236(5) no . . C8 H6 3.253(5) no . . C8 H10 3.244(4) no . . C9 H7 3.234(4) no . . C10 H6 3.247(4) no . . C10 H8 3.250(3) no . . C11 H13 3.268(3) no . . C11 H15 3.273(3) no . . C11 H16 3.283(4) no . 2_555 C12 H14 3.254(4) no . . C12 H16 3.232(3) no . . C13 H15 3.225(4) no . . C14 H12 3.248(4) no . . C14 H16 3.245(4) no . . C15 H13 3.224(4) no . . C16 H12 3.234(4) no . . C16 H14 3.251(4) no . . H3 H6 2.2787(7) no . . H3 H12 3.2838(12) no . . H6 H7 2.3303(8) no . . H7 H8 2.3284(8) no . . H8 H9 2.3174(6) no . . H9 H10 2.3332(8) no . . H12 H13 2.3455(6) no . . H13 H14 2.3049(7) no . . H14 H15 2.3211(8) no . . H15 H16 2.3424(6) no . . S1 H9 3.5364(11) no . 4_564 S1 H10 3.4763(12) no . 2_556 C4 H13 3.574(3) no . 7_556 C5 H13 2.995(4) no . 7_556 C6 H6 3.412(4) no . 7_557 C6 H12 3.293(4) no . 1_556 C6 H13 3.121(4) no . 7_556 C7 H6 3.568(5) no . 7_557 C7 H12 3.413(5) no . 1_556 C7 H12 3.471(4) no . 7_557 C7 H13 3.457(5) no . 7_556 C8 H13 3.300(4) no . 7_557 C8 H14 3.405(5) no . 6_556 C8 H14 3.056(5) no . 7_556 C9 H9 3.389(4) no . 4_564 C9 H10 3.171(4) no . 4_565 C9 H13 3.521(4) no . 7_556 C9 H14 2.944(4) no . 7_556 C10 H9 2.881(4) no . 4_564 C10 H13 3.216(4) no . 7_556 C10 H14 3.497(4) no . 7_556 C11 H3 3.498(3) no . 1_554 C11 H15 3.105(3) no . 4_555 C12 H3 3.585(4) no . 1_554 C12 H6 2.977(4) no . 1_554 C12 H7 3.518(3) no . 7_557 C12 H8 3.223(3) no . 7_557 C12 H15 3.432(4) no . 4_555 C13 H6 3.316(5) no . 1_554 C13 H8 2.928(4) no . 7_557 C13 H14 3.396(4) no . 4_555 C13 H15 3.514(4) no . 4_555 C14 H8 3.409(4) no . 6_546 C14 H14 3.393(4) no . 4_555 C14 H15 3.280(5) no . 4_555 C15 H15 2.932(5) no . 4_555 C15 H16 3.063(4) no . 2_554 C15 H16 3.211(4) no . 3_555 C16 H15 3.479(4) no . 2_554 C16 H15 3.487(4) no . 3_555 C16 H15 2.824(4) no . 4_555 C16 H16 3.157(4) no . 2_554 C16 H16 3.306(4) no . 3_555 H3 C11 3.498(3) no . 1_556 H3 C12 3.585(4) no . 1_556 H3 H7 3.3955(12) no . 7_557 H6 C6 3.412(4) no . 7_557 H6 C7 3.568(5) no . 7_557 H6 C12 2.977(4) no . 1_556 H6 C13 3.316(5) no . 1_556 H6 H6 3.0141(11) no . 7_557 H6 H7 3.3186(9) no . 7_557 H6 H12 2.8118(9) no . 1_556 H6 H13 3.3848(10) no . 1_556 H6 H13 3.5091(8) no . 7_556 H7 C12 3.518(3) no . 7_557 H7 H3 3.3955(12) no . 7_557 H7 H6 3.3186(9) no . 7_557 H7 H7 3.0691(9) no . 7_558 H7 H12 3.0344(8) no . 1_556 H7 H12 2.7578(9) no . 7_557 H7 H13 3.4575(13) no . 7_557 H8 C12 3.223(3) no . 7_557 H8 C13 2.928(4) no . 7_557 H8 C14 3.409(4) no . 6_556 H8 H9 3.2186(8) no . 4_565 H8 H12 3.0607(7) no . 7_557 H8 H13 2.5176(11) no . 7_557 H8 H14 2.6794(8) no . 6_556 H8 H14 3.2340(11) no . 7_556 H9 S1 3.5364(11) no . 4_565 H9 C9 3.389(4) no . 4_565 H9 C10 2.881(4) no . 4_565 H9 H8 3.2186(8) no . 4_564 H9 H9 3.3416(15) no . 4_564 H9 H9 3.3416(15) no . 4_565 H9 H10 2.4326(6) no . 4_565 H9 H13 3.1880(8) no . 6_556 H9 H14 3.1943(9) no . 6_556 H9 H14 3.0472(9) no . 7_556 H10 S1 3.4763(12) no . 2_556 H10 C9 3.171(4) no . 4_564 H10 H9 2.4326(6) no . 4_564 H12 C6 3.293(4) no . 1_554 H12 C7 3.413(5) no . 1_554 H12 C7 3.471(4) no . 7_557 H12 H6 2.8118(9) no . 1_554 H12 H7 3.0344(8) no . 1_554 H12 H7 2.7578(9) no . 7_557 H12 H8 3.0607(7) no . 7_557 H13 C4 3.574(3) no . 7_556 H13 C5 2.995(4) no . 7_556 H13 C6 3.121(4) no . 7_556 H13 C7 3.457(5) no . 7_556 H13 C8 3.300(4) no . 7_557 H13 C9 3.521(4) no . 7_556 H13 C10 3.216(4) no . 7_556 H13 H6 3.3848(10) no . 1_554 H13 H6 3.5091(8) no . 7_556 H13 H7 3.4575(13) no . 7_557 H13 H8 2.5176(11) no . 7_557 H13 H9 3.1880(8) no . 6_546 H13 H14 3.5269(10) no . 4_555 H14 C8 3.405(5) no . 6_546 H14 C8 3.056(5) no . 7_556 H14 C9 2.944(4) no . 7_556 H14 C10 3.497(4) no . 7_556 H14 C13 3.396(4) no . 4_554 H14 C14 3.393(4) no . 4_554 H14 H8 2.6794(8) no . 6_546 H14 H8 3.2340(11) no . 7_556 H14 H9 3.1943(9) no . 6_546 H14 H9 3.0472(9) no . 7_556 H14 H13 3.5269(10) no . 4_554 H14 H14 3.5147(15) no . 4_554 H14 H14 3.5147(15) no . 4_555 H15 C11 3.105(3) no . 4_554 H15 C12 3.432(4) no . 4_554 H15 C13 3.514(4) no . 4_554 H15 C14 3.280(5) no . 4_554 H15 C15 2.932(5) no . 4_554 H15 C16 3.479(4) no . 2_554 H15 C16 3.487(4) no . 3_555 H15 C16 2.824(4) no . 4_554 H15 H15 3.2748(11) no . 2_554 H15 H15 3.3227(15) no . 4_554 H15 H15 3.3227(15) no . 4_555 H15 H16 2.6992(7) no . 2_554 H15 H16 2.8342(7) no . 3_555 H15 H16 3.1569(9) no . 4_554 H16 C15 3.063(4) no . 2_554 H16 C15 3.211(4) no . 3_555 H16 C16 3.157(4) no . 2_554 H16 C16 3.306(4) no . 3_555 H16 H15 2.6992(7) no . 2_554 H16 H15 2.8342(7) no . 3_555 H16 H15 3.1569(9) no . 4_555 H16 H16 2.8700(13) no . 2_554 H16 H16 3.0012(11) no . 3_555 data_sc0972 _database_code_depnum_ccdc_archive 'CCDC 875780' #TrackingRef '2_Si-BT.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C32 H22 S2 Si' _chemical_formula_moiety 'C32 H22 S2 Si' _chemical_formula_weight 498.73 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,+Y,1/2-Z 3 -X,-Y,-Z 4 +X,-Y,1/2+Z 5 1/2+X,1/2+Y,+Z 6 1/2-X,1/2+Y,1/2-Z 7 1/2-X,1/2-Y,-Z 8 1/2+X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 19.549(7) _cell_length_b 19.718(6) _cell_length_c 6.618(2) _cell_angle_alpha 90.0000 _cell_angle_beta 101.413(5) _cell_angle_gamma 90.0000 _cell_volume 2500.6(14) _cell_formula_units_Z 4 _cell_measurement_reflns_used 4171 _cell_measurement_theta_min 3.10 _cell_measurement_theta_max 27.50 _cell_measurement_temperature 93 #------------------------------------------------------------------------------ _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.310 _exptl_crystal_size_mid 0.152 _exptl_crystal_size_min 0.147 _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040.00 _exptl_absorpt_coefficient_mu 0.281 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_correction_T_min 0.877 _exptl_absorpt_correction_T_max 0.960 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 93 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku Saturn724' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.111 _diffrn_reflns_number 19742 _diffrn_reflns_av_R_equivalents 0.0270 _diffrn_reflns_theta_max 27.52 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measured_fraction_theta_full 0.994 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2869 _reflns_number_gt 2509 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0312 _refine_ls_wR_factor_ref 0.0879 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 2869 _refine_ls_number_parameters 159 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0516P)^2^+1.0859P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.380 _refine_diff_density_min -0.240 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; S S 0.1246 0.1234 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Si Si 0.0817 0.0704 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 S1 S 0.447130(16) 0.881713(15) 0.48238(5) 0.01854(11) Uani 1.0 8 d . . . Si1 Si 0.5000 0.68777(2) 0.7500 0.01636(12) Uani 1.0 4 d . . . C1 C 0.40911(6) 0.82501(6) 0.29050(18) 0.0181(3) Uani 1.0 8 d . . . C2 C 0.42191(6) 0.75915(6) 0.35566(18) 0.0189(3) Uani 1.0 8 d . . . C3 C 0.46162(6) 0.75339(6) 0.55807(19) 0.0177(3) Uani 1.0 8 d . . . C4 C 0.47916(6) 0.81657(6) 0.64562(18) 0.0168(3) Uani 1.0 8 d . . . C5 C 0.43242(6) 0.63379(6) 0.83468(18) 0.0177(3) Uani 1.0 8 d . . . C6 C 0.36093(7) 0.64269(7) 0.7593(2) 0.0223(3) Uani 1.0 8 d . . . C7 C 0.31194(7) 0.60302(7) 0.8330(3) 0.0274(3) Uani 1.0 8 d . . . C8 C 0.33377(8) 0.55382(7) 0.9805(3) 0.0276(3) Uani 1.0 8 d . . . C9 C 0.40432(8) 0.54407(7) 1.0566(2) 0.0278(3) Uani 1.0 8 d . . . C10 C 0.45299(7) 0.58388(7) 0.9843(2) 0.0230(3) Uani 1.0 8 d . . . C11 C 0.36897(6) 0.84932(7) 0.09267(19) 0.0201(3) Uani 1.0 8 d . . . C12 C 0.32616(8) 0.80454(7) -0.0390(2) 0.0286(3) Uani 1.0 8 d . . . C13 C 0.28653(9) 0.82709(8) -0.2245(3) 0.0355(4) Uani 1.0 8 d . . . C14 C 0.28805(8) 0.89460(8) -0.2800(3) 0.0344(4) Uani 1.0 8 d . . . C15 C 0.33030(7) 0.93968(8) -0.1518(3) 0.0293(4) Uani 1.0 8 d . . . C16 C 0.37116(7) 0.91721(7) 0.0322(2) 0.0232(3) Uani 1.0 8 d . . . H2 H 0.4056 0.7210 0.2722 0.0227 Uiso 1.0 8 calc R . . H6 H 0.3455 0.6761 0.6569 0.0268 Uiso 1.0 8 calc R . . H7 H 0.2635 0.6099 0.7816 0.0329 Uiso 1.0 8 calc R . . H8 H 0.3004 0.5267 1.0297 0.0331 Uiso 1.0 8 calc R . . H9 H 0.4194 0.5103 1.1579 0.0334 Uiso 1.0 8 calc R . . H10 H 0.5013 0.5770 1.0378 0.0276 Uiso 1.0 8 calc R . . H12 H 0.3241 0.7582 -0.0014 0.0343 Uiso 1.0 8 calc R . . H13 H 0.2582 0.7960 -0.3138 0.0425 Uiso 1.0 8 calc R . . H14 H 0.2602 0.9100 -0.4058 0.0412 Uiso 1.0 8 calc R . . H15 H 0.3314 0.9861 -0.1896 0.0352 Uiso 1.0 8 calc R . . H16 H 0.4009 0.9482 0.1178 0.0279 Uiso 1.0 8 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S1 0.01984(17) 0.01631(17) 0.01901(17) 0.00162(11) 0.00272(12) 0.00142(11) Si1 0.0172(3) 0.0148(3) 0.0162(3) 0.0000 0.00109(17) 0.0000 C1 0.0166(6) 0.0209(6) 0.0170(6) 0.0011(5) 0.0038(5) -0.0002(5) C2 0.0191(6) 0.0191(6) 0.0182(6) 0.0012(5) 0.0031(5) -0.0007(5) C3 0.0172(6) 0.0175(6) 0.0186(6) 0.0013(5) 0.0040(5) 0.0008(5) C4 0.0156(6) 0.0171(6) 0.0180(6) 0.0015(5) 0.0042(5) 0.0017(5) C5 0.0194(6) 0.0169(6) 0.0165(6) -0.0005(5) 0.0028(5) -0.0027(5) C6 0.0212(7) 0.0234(7) 0.0217(7) 0.0020(5) 0.0026(5) -0.0003(5) C7 0.0192(7) 0.0332(8) 0.0303(8) -0.0024(6) 0.0065(6) -0.0054(6) C8 0.0318(8) 0.0280(7) 0.0262(7) -0.0088(6) 0.0139(6) -0.0051(6) C9 0.0366(8) 0.0253(7) 0.0225(7) -0.0021(6) 0.0081(6) 0.0039(6) C10 0.0231(7) 0.0231(7) 0.0218(7) 0.0010(5) 0.0019(5) 0.0025(5) C11 0.0189(6) 0.0236(7) 0.0187(6) 0.0069(5) 0.0059(5) 0.0015(5) C12 0.0341(8) 0.0262(7) 0.0227(7) 0.0078(6) -0.0014(6) -0.0002(6) C13 0.0414(9) 0.0379(9) 0.0222(7) 0.0096(7) -0.0057(6) -0.0040(6) C14 0.0373(8) 0.0441(9) 0.0199(7) 0.0164(7) 0.0014(6) 0.0062(6) C15 0.0287(7) 0.0324(8) 0.0286(7) 0.0097(6) 0.0097(6) 0.0125(6) C16 0.0200(7) 0.0263(7) 0.0245(7) 0.0049(5) 0.0070(5) 0.0044(6) #============================================================================== _computing_data_collection 'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r4' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r4' _computing_structure_solution 'Il Milione (Burla, et al., 2007)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 S1 C1 1.7440(13) yes . . S1 C4 1.7150(13) yes . . Si1 C3 1.8637(13) yes . . Si1 C3 1.8637(13) yes . 2_656 Si1 C5 1.8669(14) yes . . Si1 C5 1.8669(14) yes . 2_656 C1 C2 1.3756(17) yes . . C1 C11 1.4673(17) yes . . C2 C3 1.4136(17) yes . . C3 C4 1.3880(17) yes . . C4 C4 1.4585(16) yes . 2_656 C5 C6 1.3989(18) yes . . C5 C10 1.3977(18) yes . . C6 C7 1.397(2) yes . . C7 C8 1.383(2) yes . . C8 C9 1.385(3) yes . . C9 C10 1.389(3) yes . . C11 C12 1.3968(19) yes . . C11 C16 1.400(2) yes . . C12 C13 1.389(2) yes . . C13 C14 1.383(3) yes . . C14 C15 1.384(2) yes . . C15 C16 1.3899(19) yes . . C2 H2 0.950 no . . C6 H6 0.950 no . . C7 H7 0.950 no . . C8 H8 0.950 no . . C9 H9 0.950 no . . C10 H10 0.950 no . . C12 H12 0.950 no . . C13 H13 0.950 no . . C14 H14 0.950 no . . C15 H15 0.950 no . . C16 H16 0.950 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C1 S1 C4 91.63(6) yes . . . C3 Si1 C3 92.06(6) yes . . 2_656 C3 Si1 C5 112.77(6) yes . . . C3 Si1 C5 113.87(6) yes . . 2_656 C3 Si1 C5 113.87(6) yes 2_656 . . C3 Si1 C5 112.77(6) yes 2_656 . 2_656 C5 Si1 C5 110.48(6) yes . . 2_656 S1 C1 C2 110.61(9) yes . . . S1 C1 C11 121.06(10) yes . . . C2 C1 C11 128.32(11) yes . . . C1 C2 C3 113.87(11) yes . . . Si1 C3 C2 140.64(10) yes . . . Si1 C3 C4 107.80(9) yes . . . C2 C3 C4 111.56(11) yes . . . S1 C4 C3 112.33(9) yes . . . S1 C4 C4 131.50(10) yes . . 2_656 C3 C4 C4 116.17(11) yes . . 2_656 Si1 C5 C6 122.53(10) yes . . . Si1 C5 C10 119.52(10) yes . . . C6 C5 C10 117.91(12) yes . . . C5 C6 C7 120.72(12) yes . . . C6 C7 C8 120.15(13) yes . . . C7 C8 C9 120.01(14) yes . . . C8 C9 C10 119.81(13) yes . . . C5 C10 C9 121.41(12) yes . . . C1 C11 C12 119.93(12) yes . . . C1 C11 C16 121.74(11) yes . . . C12 C11 C16 118.32(12) yes . . . C11 C12 C13 120.65(13) yes . . . C12 C13 C14 120.36(14) yes . . . C13 C14 C15 119.80(13) yes . . . C14 C15 C16 120.15(14) yes . . . C11 C16 C15 120.69(13) yes . . . C1 C2 H2 123.064 no . . . C3 C2 H2 123.069 no . . . C5 C6 H6 119.653 no . . . C7 C6 H6 119.632 no . . . C6 C7 H7 119.926 no . . . C8 C7 H7 119.926 no . . . C7 C8 H8 119.991 no . . . C9 C8 H8 119.999 no . . . C8 C9 H9 120.095 no . . . C10 C9 H9 120.099 no . . . C5 C10 H10 119.292 no . . . C9 C10 H10 119.301 no . . . C11 C12 H12 119.672 no . . . C13 C12 H12 119.679 no . . . C12 C13 H13 119.813 no . . . C14 C13 H13 119.824 no . . . C13 C14 H14 120.101 no . . . C15 C14 H14 120.099 no . . . C14 C15 H15 119.923 no . . . C16 C15 H15 119.925 no . . . C11 C16 H16 119.664 no . . . C15 C16 H16 119.651 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C1 S1 C4 C3 -0.07(9) no . . . . C1 S1 C4 C4 179.54(11) no . . . 2_656 C4 S1 C1 C2 -0.10(9) no . . . . C4 S1 C1 C11 179.03(10) no . . . . C3 Si1 C3 C2 179.11(14) no . . 2_656 2_656 C3 Si1 C3 C4 0.03(8) no . . 2_656 2_656 C3 Si1 C3 C2 179.11(14) no 2_656 . . . C3 Si1 C3 C4 0.03(8) no 2_656 . . . C3 Si1 C5 C6 0.10(11) no . . . . C3 Si1 C5 C10 -177.60(8) no . . . . C5 Si1 C3 C2 -63.87(15) no . . . . C5 Si1 C3 C4 117.04(8) no . . . . C3 Si1 C5 C6 103.31(9) no . . 2_656 2_656 C3 Si1 C5 C10 -74.40(10) no . . 2_656 2_656 C5 Si1 C3 C2 63.04(15) no 2_656 . . . C5 Si1 C3 C4 -116.04(8) no 2_656 . . . C3 Si1 C5 C6 103.31(9) no 2_656 . . . C3 Si1 C5 C10 -74.40(10) no 2_656 . . . C5 Si1 C3 C2 63.04(15) no . . 2_656 2_656 C5 Si1 C3 C4 -116.04(8) no . . 2_656 2_656 C3 Si1 C5 C6 0.10(11) no 2_656 . 2_656 2_656 C3 Si1 C5 C10 -177.60(8) no 2_656 . 2_656 2_656 C5 Si1 C3 C2 -63.87(15) no 2_656 . 2_656 2_656 C5 Si1 C3 C4 117.04(8) no 2_656 . 2_656 2_656 C5 Si1 C5 C6 -128.59(9) no . . 2_656 2_656 C5 Si1 C5 C10 53.70(10) no . . 2_656 2_656 C5 Si1 C5 C6 -128.59(9) no 2_656 . . . C5 Si1 C5 C10 53.70(10) no 2_656 . . . S1 C1 C2 C3 0.25(14) no . . . . S1 C1 C11 C12 -165.46(9) no . . . . S1 C1 C11 C16 13.32(17) no . . . . C2 C1 C11 C12 13.5(2) no . . . . C2 C1 C11 C16 -167.72(12) no . . . . C11 C1 C2 C3 -178.80(11) no . . . . C1 C2 C3 Si1 -179.37(12) no . . . . C1 C2 C3 C4 -0.31(16) no . . . . Si1 C3 C4 S1 179.60(7) no . . . . Si1 C3 C4 C4 -0.07(13) no . . . 2_656 C2 C3 C4 S1 0.22(15) no . . . . C2 C3 C4 C4 -179.45(10) no . . . 2_656 S1 C4 C4 S1 0.9(2) no . . 2_656 2_656 S1 C4 C4 C3 -179.49(9) no . . 2_656 2_656 C3 C4 C4 S1 -179.49(11) no . . 2_656 2_656 C3 C4 C4 C3 0.10(17) no . . 2_656 2_656 Si1 C5 C6 C7 -177.35(8) no . . . . Si1 C5 C10 C9 177.90(8) no . . . . C6 C5 C10 C9 0.09(19) no . . . . C10 C5 C6 C7 0.39(19) no . . . . C5 C6 C7 C8 -0.6(2) no . . . . C6 C7 C8 C9 0.4(2) no . . . . C7 C8 C9 C10 0.1(2) no . . . . C8 C9 C10 C5 -0.3(2) no . . . . C1 C11 C12 C13 178.43(12) no . . . . C1 C11 C16 C15 -177.13(11) no . . . . C12 C11 C16 C15 1.7(2) no . . . . C16 C11 C12 C13 -0.4(2) no . . . . C11 C12 C13 C14 -1.0(3) no . . . . C12 C13 C14 C15 1.2(3) no . . . . C13 C14 C15 C16 0.1(3) no . . . . C14 C15 C16 C11 -1.5(3) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 S1 C16 3.1338(16) no . . Si1 C2 3.0896(13) no . 2_656 Si1 C4 2.6423(15) no . 2_656 Si1 C6 2.8725(17) no . 2_656 Si1 C10 2.8302(16) no . 2_656 C2 C12 3.0320(19) no . . C3 C6 3.384(2) no . . C5 C8 2.806(2) no . . C5 C10 3.509(2) no . 2_656 C6 C9 2.777(2) no . . C7 C10 2.767(2) no . . C11 C14 2.7998(19) no . . C12 C15 2.773(3) no . . C13 C16 2.769(2) no . . C6 C12 3.576(3) no . 1_556 C8 C14 3.536(3) no . 7_566 C12 C6 3.576(3) no . 1_554 C14 C8 3.536(3) no . 7_566 S1 H2 3.4910 no . . S1 H16 2.7379 no . . Si1 H2 3.3949 no . . Si1 H2 3.3949 no . 2_656 Si1 H6 2.9692 no . . Si1 H6 2.9692 no . 2_656 Si1 H10 2.8942 no . . Si1 H10 2.8942 no . 2_656 C1 H12 2.6373 no . . C1 H16 2.6765 no . . C2 H6 3.1727 no . . C2 H12 2.7292 no . . C3 H6 2.9139 no . . C4 H2 3.2123 no . . C5 H7 3.2847 no . . C5 H9 3.2845 no . . C5 H10 3.2051 no . 2_656 C6 H8 3.2672 no . . C6 H10 3.2557 no . . C7 H9 3.2548 no . . C8 H6 3.2627 no . . C8 H10 3.2535 no . . C9 H7 3.2540 no . . C10 H6 3.2577 no . . C10 H8 3.2587 no . . C11 H2 2.8262 no . . C11 H13 3.2749 no . . C11 H15 3.2800 no . . C12 H2 2.8460 no . . C12 H14 3.2619 no . . C12 H16 3.2619 no . . C13 H15 3.2513 no . . C14 H12 3.2585 no . . C14 H16 3.2585 no . . C15 H13 3.2508 no . . C16 H12 3.2625 no . . C16 H14 3.2622 no . . H2 H6 3.1346 no . . H2 H10 3.4715 no . 2_656 H2 H12 2.2823 no . . H6 H7 2.3407 no . . H7 H8 2.3315 no . . H8 H9 2.3362 no . . H9 H10 2.3306 no . . H12 H13 2.3315 no . . H13 H14 2.3318 no . . H14 H15 2.3343 no . . H15 H16 2.3339 no . . S1 H15 3.4916 no . 4_575 S1 H16 3.4305 no . 2_655 C1 H7 3.5537 no . 7_566 C5 H2 3.4959 no . 1_556 C5 H9 3.0633 no . 4_564 C5 H12 3.5475 no . 1_556 C6 H9 3.3400 no . 4_564 C6 H12 2.9436 no . 1_556 C6 H13 3.5866 no . 7_565 C6 H14 3.1567 no . 7_565 C7 H8 3.2314 no . 4_564 C7 H9 3.4216 no . 4_564 C7 H12 3.2432 no . 1_556 C7 H14 2.9098 no . 7_565 C8 H8 3.3282 no . 4_564 C8 H9 3.2205 no . 4_564 C8 H14 3.3617 no . 6_545 C9 H9 2.9163 no . 4_564 C9 H10 3.0123 no . 2_657 C9 H10 3.1551 no . 3_667 C10 H2 3.5358 no . 1_556 C10 H9 3.4060 no . 2_657 C10 H9 3.3889 no . 3_667 C10 H9 2.8255 no . 4_564 C10 H10 3.1146 no . 2_657 C10 H10 3.3076 no . 3_667 C11 H7 2.9836 no . 7_566 C12 H6 3.3032 no . 1_554 C12 H7 3.1635 no . 7_566 C12 H12 3.2474 no . 7_565 C13 H6 3.3424 no . 1_554 C13 H6 3.4542 no . 7_565 C13 H7 3.4973 no . 7_566 C13 H12 3.3202 no . 7_565 C14 H6 3.5217 no . 7_565 C14 H7 3.2737 no . 7_565 C14 H8 3.3722 no . 6_555 C14 H8 3.0451 no . 7_566 C15 H7 3.4783 no . 7_566 C15 H8 2.9039 no . 7_566 C15 H15 3.3874 no . 4_575 C15 H16 3.1537 no . 4_574 C16 H7 3.1654 no . 7_566 C16 H8 3.4771 no . 7_566 C16 H15 2.8633 no . 4_575 H2 C5 3.4959 no . 1_554 H2 C10 3.5358 no . 1_554 H2 H13 3.2844 no . 7_565 H6 C12 3.3032 no . 1_556 H6 C13 3.3424 no . 1_556 H6 C13 3.4542 no . 7_565 H6 C14 3.5217 no . 7_565 H6 H12 2.8788 no . 1_556 H6 H13 2.9445 no . 1_556 H6 H13 2.7839 no . 7_565 H6 H14 2.9242 no . 7_565 H7 C1 3.5537 no . 7_566 H7 C11 2.9836 no . 7_566 H7 C12 3.1635 no . 7_566 H7 C13 3.4973 no . 7_566 H7 C14 3.2737 no . 7_565 H7 C15 3.4783 no . 7_566 H7 C16 3.1654 no . 7_566 H7 H8 3.3201 no . 4_564 H7 H12 3.3689 no . 1_556 H7 H12 3.5786 no . 7_566 H7 H13 3.5627 no . 7_565 H7 H14 2.4689 no . 7_565 H7 H15 3.0530 no . 6_545 H7 H16 3.5960 no . 7_566 H8 C7 3.2314 no . 4_565 H8 C8 3.3282 no . 4_565 H8 C14 3.3722 no . 6_545 H8 C14 3.0451 no . 7_566 H8 C15 2.9039 no . 7_566 H8 C16 3.4771 no . 7_566 H8 H7 3.3201 no . 4_565 H8 H8 3.4725 no . 4_564 H8 H8 3.4725 no . 4_565 H8 H14 2.6429 no . 6_545 H8 H14 3.2126 no . 7_566 H8 H15 3.1696 no . 6_545 H8 H15 2.9820 no . 7_566 H9 C5 3.0633 no . 4_565 H9 C6 3.3400 no . 4_565 H9 C7 3.4216 no . 4_565 H9 C8 3.2205 no . 4_565 H9 C9 2.9163 no . 4_565 H9 C10 3.4060 no . 2_657 H9 C10 3.3889 no . 3_667 H9 C10 2.8255 no . 4_565 H9 H9 3.1463 no . 2_657 H9 H9 3.3336 no . 4_564 H9 H9 3.3336 no . 4_565 H9 H10 2.6381 no . 2_657 H9 H10 2.7999 no . 3_667 H9 H10 3.2023 no . 4_565 H10 C9 3.0123 no . 2_657 H10 C9 3.1551 no . 3_667 H10 C10 3.1146 no . 2_657 H10 C10 3.3076 no . 3_667 H10 H9 2.6381 no . 2_657 H10 H9 2.7999 no . 3_667 H10 H9 3.2023 no . 4_564 H10 H10 2.8191 no . 2_657 H10 H10 3.0778 no . 3_667 H12 C5 3.5475 no . 1_554 H12 C6 2.9436 no . 1_554 H12 C7 3.2432 no . 1_554 H12 C12 3.2474 no . 7_565 H12 C13 3.3202 no . 7_565 H12 H6 2.8788 no . 1_554 H12 H7 3.3689 no . 1_554 H12 H7 3.5786 no . 7_566 H12 H12 2.9203 no . 7_565 H12 H13 3.0677 no . 7_565 H13 C6 3.5866 no . 7_565 H13 H2 3.2844 no . 7_565 H13 H6 2.9445 no . 1_554 H13 H6 2.7839 no . 7_565 H13 H7 3.5627 no . 7_565 H13 H12 3.0677 no . 7_565 H13 H13 3.0249 no . 7_564 H14 C6 3.1567 no . 7_565 H14 C7 2.9098 no . 7_565 H14 C8 3.3617 no . 6_555 H14 H6 2.9242 no . 7_565 H14 H7 2.4689 no . 7_565 H14 H8 2.6429 no . 6_555 H14 H8 3.2126 no . 7_566 H14 H15 3.2704 no . 4_574 H15 S1 3.4916 no . 4_574 H15 C15 3.3874 no . 4_574 H15 C16 2.8633 no . 4_574 H15 H7 3.0530 no . 6_555 H15 H8 3.1696 no . 6_555 H15 H8 2.9820 no . 7_566 H15 H14 3.2704 no . 4_575 H15 H15 3.3542 no . 4_574 H15 H15 3.3542 no . 4_575 H15 H16 2.4154 no . 4_574 H16 S1 3.4305 no . 2_655 H16 C15 3.1537 no . 4_575 H16 H7 3.5960 no . 7_566 H16 H15 2.4154 no . 4_575 data_sc0971 _database_code_depnum_ccdc_archive 'CCDC 875781' #TrackingRef '3_SO2-BT.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C20 H12 O2 S3' _chemical_formula_moiety 'C20 H12 O2 S3' _chemical_formula_weight 380.49 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,+Y,1/2-Z 3 -X,-Y,-Z 4 +X,-Y,1/2+Z 5 1/2+X,1/2+Y,+Z 6 1/2-X,1/2+Y,1/2-Z 7 1/2-X,1/2-Y,-Z 8 1/2+X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 16.192(3) _cell_length_b 15.167(3) _cell_length_c 13.658(3) _cell_angle_alpha 90.0000 _cell_angle_beta 96.209(3) _cell_angle_gamma 90.0000 _cell_volume 3334.5(12) _cell_formula_units_Z 8 _cell_measurement_reflns_used 5874 _cell_measurement_theta_min 3.10 _cell_measurement_theta_max 27.50 _cell_measurement_temperature 93 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.220 _exptl_crystal_size_mid 0.140 _exptl_crystal_size_min 0.050 _exptl_crystal_density_diffrn 1.516 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1568.00 _exptl_absorpt_coefficient_mu 0.455 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_correction_T_min 0.855 _exptl_absorpt_correction_T_max 0.977 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 93 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku Saturn724' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.111 _diffrn_reflns_number 26184 _diffrn_reflns_av_R_equivalents 0.0506 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 3817 _reflns_number_gt 3252 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0506 _refine_ls_wR_factor_ref 0.1299 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 3817 _refine_ls_number_parameters 226 _refine_ls_goodness_of_fit_ref 1.171 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0852P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_diff_density_max 0.480 _refine_diff_density_min -1.080 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; O O 0.0106 0.0060 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; S S 0.1246 0.1234 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 S1 S 0.37817(3) 0.40739(3) 0.53941(3) 0.01253(14) Uani 1.0 8 d . . . S2 S 0.59443(3) 0.45747(3) 0.68106(3) 0.01265(14) Uani 1.0 8 d . . . S3 S 0.58490(3) 0.28835(3) 0.43983(3) 0.01256(14) Uani 1.0 8 d . . . O1 O 0.61638(9) 0.31926(9) 0.35173(10) 0.0212(4) Uani 1.0 8 d . . . O2 O 0.59347(9) 0.19528(9) 0.46058(11) 0.0206(4) Uani 1.0 8 d . . . C1 C 0.34058(11) 0.34266(11) 0.43849(13) 0.0121(4) Uani 1.0 8 d . . . C2 C 0.40430(11) 0.30209(12) 0.39654(13) 0.0129(4) Uani 1.0 8 d . . . C3 C 0.48190(11) 0.32336(12) 0.44747(13) 0.0119(4) Uani 1.0 8 d . . . C4 C 0.47821(11) 0.37893(12) 0.52662(13) 0.0113(4) Uani 1.0 8 d . . . C5 C 0.55908(11) 0.39515(11) 0.58160(13) 0.0115(4) Uani 1.0 8 d . . . C6 C 0.62313(11) 0.35212(12) 0.54358(13) 0.0124(4) Uani 1.0 8 d . . . C7 C 0.70252(11) 0.36860(12) 0.59418(13) 0.0132(4) Uani 1.0 8 d . . . C8 C 0.69711(11) 0.42539(12) 0.67203(13) 0.0124(4) Uani 1.0 8 d . . . C9 C 0.25064(11) 0.33520(12) 0.40961(13) 0.0123(4) Uani 1.0 8 d . . . C10 C 0.19377(13) 0.37583(16) 0.46405(16) 0.0263(5) Uani 1.0 8 d . . . C11 C 0.10889(13) 0.36578(18) 0.43751(17) 0.0327(6) Uani 1.0 8 d . . . C12 C 0.07967(12) 0.31779(14) 0.35624(15) 0.0211(5) Uani 1.0 8 d . . . C13 C 0.13581(12) 0.27650(13) 0.30190(16) 0.0199(5) Uani 1.0 8 d . . . C14 C 0.22067(12) 0.28479(13) 0.32855(16) 0.0195(5) Uani 1.0 8 d . . . C15 C 0.76448(11) 0.45960(12) 0.74286(13) 0.0133(4) Uani 1.0 8 d . . . C16 C 0.84313(12) 0.42088(14) 0.75141(14) 0.0193(5) Uani 1.0 8 d . . . C17 C 0.90658(12) 0.45460(15) 0.81748(14) 0.0232(5) Uani 1.0 8 d . . . C18 C 0.89191(13) 0.52673(14) 0.87562(15) 0.0230(5) Uani 1.0 8 d . . . C19 C 0.81421(13) 0.56477(13) 0.86826(15) 0.0229(5) Uani 1.0 8 d . . . C20 C 0.75061(12) 0.53166(12) 0.80255(14) 0.0174(4) Uani 1.0 8 d . . . H2 H 0.3968 0.2646 0.3405 0.0155 Uiso 1.0 8 calc R . . H7 H 0.7528 0.3438 0.5768 0.0158 Uiso 1.0 8 calc R . . H10 H 0.2129 0.4107 0.5197 0.0316 Uiso 1.0 8 calc R . . H11 H 0.0707 0.3926 0.4764 0.0392 Uiso 1.0 8 calc R . . H12 H 0.0216 0.3129 0.3374 0.0253 Uiso 1.0 8 calc R . . H13 H 0.1162 0.2422 0.2460 0.0239 Uiso 1.0 8 calc R . . H14 H 0.2586 0.2557 0.2910 0.0234 Uiso 1.0 8 calc R . . H16 H 0.8533 0.3713 0.7119 0.0231 Uiso 1.0 8 calc R . . H17 H 0.9601 0.4282 0.8228 0.0279 Uiso 1.0 8 calc R . . H18 H 0.9354 0.5499 0.9205 0.0275 Uiso 1.0 8 calc R . . H19 H 0.8042 0.6139 0.9084 0.0275 Uiso 1.0 8 calc R . . H20 H 0.6972 0.5582 0.7981 0.0209 Uiso 1.0 8 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S1 0.0087(3) 0.0156(3) 0.0133(3) 0.00172(16) 0.00104(17) -0.00184(16) S2 0.0096(3) 0.0159(3) 0.0125(3) 0.00089(16) 0.00123(17) -0.00278(16) S3 0.0095(3) 0.0148(3) 0.0136(3) 0.00104(16) 0.00187(17) -0.00321(16) O1 0.0186(8) 0.0310(8) 0.0149(7) -0.0050(6) 0.0065(6) -0.0035(6) O2 0.0201(8) 0.0137(7) 0.0276(8) 0.0057(6) 0.0009(6) -0.0037(6) C1 0.0114(9) 0.0122(9) 0.0123(9) -0.0003(7) 0.0000(7) 0.0019(7) C2 0.0120(9) 0.0138(9) 0.0127(9) -0.0001(7) 0.0001(7) -0.0014(7) C3 0.0107(9) 0.0119(9) 0.0131(9) 0.0005(7) 0.0020(7) -0.0002(7) C4 0.0092(8) 0.0121(9) 0.0125(9) 0.0008(7) 0.0006(7) 0.0006(7) C5 0.0096(9) 0.0125(9) 0.0123(9) 0.0011(7) 0.0007(7) 0.0009(7) C6 0.0106(9) 0.0142(9) 0.0123(9) 0.0015(7) 0.0012(7) -0.0004(7) C7 0.0098(9) 0.0154(9) 0.0145(9) 0.0013(7) 0.0019(7) -0.0003(7) C8 0.0091(9) 0.0146(9) 0.0134(9) 0.0000(7) 0.0016(7) 0.0023(7) C9 0.0099(9) 0.0137(9) 0.0131(9) 0.0007(7) -0.0001(7) 0.0042(7) C10 0.0139(10) 0.0443(14) 0.0195(11) 0.0055(10) -0.0040(8) -0.0135(10) C11 0.0141(10) 0.0593(17) 0.0241(12) 0.0101(11) -0.0011(9) -0.0136(11) C12 0.0104(9) 0.0302(11) 0.0213(11) 0.0003(8) -0.0039(8) 0.0017(9) C13 0.0151(10) 0.0191(10) 0.0243(11) -0.0013(8) -0.0037(8) -0.0028(8) C14 0.0129(10) 0.0194(10) 0.0256(11) 0.0012(8) -0.0003(8) -0.0065(8) C15 0.0113(9) 0.0172(9) 0.0113(9) -0.0031(7) 0.0012(7) 0.0025(7) C16 0.0134(9) 0.0287(11) 0.0159(10) 0.0002(8) 0.0019(8) -0.0031(8) C17 0.0104(10) 0.0425(14) 0.0167(11) -0.0016(9) 0.0010(8) 0.0013(9) C18 0.0198(11) 0.0304(12) 0.0174(10) -0.0131(9) -0.0039(8) 0.0024(9) C19 0.0271(11) 0.0180(10) 0.0226(11) -0.0061(9) -0.0024(9) -0.0026(8) C20 0.0170(10) 0.0164(9) 0.0183(10) -0.0007(8) -0.0006(8) 0.0005(8) #============================================================================== _computing_data_collection 'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r4' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r4' _computing_structure_solution 'Il Milione (Burla, et al., 2007)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 S1 C1 1.7472(18) yes . . S1 C4 1.7035(19) yes . . S2 C5 1.7024(18) yes . . S2 C8 1.7494(19) yes . . S3 O1 1.4353(16) yes . . S3 O2 1.4435(15) yes . . S3 C3 1.7641(19) yes . . S3 C6 1.7711(19) yes . . C1 C2 1.378(3) yes . . C1 C9 1.471(3) yes . . C2 C3 1.406(3) yes . . C3 C4 1.377(3) yes . . C4 C5 1.458(3) yes . . C5 C6 1.374(3) yes . . C6 C7 1.414(3) yes . . C7 C8 1.379(3) yes . . C8 C15 1.472(3) yes . . C9 C10 1.389(3) yes . . C9 C14 1.389(3) yes . . C10 C11 1.391(3) yes . . C11 C12 1.368(4) yes . . C12 C13 1.384(3) yes . . C13 C14 1.389(3) yes . . C15 C16 1.396(3) yes . . C15 C20 1.396(3) yes . . C16 C17 1.390(3) yes . . C17 C18 1.387(3) yes . . C18 C19 1.378(3) yes . . C19 C20 1.385(3) yes . . C2 H2 0.950 no . . C7 H7 0.950 no . . C10 H10 0.950 no . . C11 H11 0.950 no . . C12 H12 0.950 no . . C13 H13 0.950 no . . C14 H14 0.950 no . . C16 H16 0.950 no . . C17 H17 0.950 no . . C18 H18 0.950 no . . C19 H19 0.950 no . . C20 H20 0.950 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C1 S1 C4 91.76(9) yes . . . C5 S2 C8 91.69(9) yes . . . O1 S3 O2 116.66(9) yes . . . O1 S3 C3 112.02(9) yes . . . O1 S3 C6 111.55(9) yes . . . O2 S3 C3 110.74(9) yes . . . O2 S3 C6 111.04(9) yes . . . C3 S3 C6 92.24(9) yes . . . S1 C1 C2 111.49(13) yes . . . S1 C1 C9 120.33(14) yes . . . C2 C1 C9 128.17(16) yes . . . C1 C2 C3 111.16(16) yes . . . S3 C3 C2 134.55(15) yes . . . S3 C3 C4 110.62(13) yes . . . C2 C3 C4 114.61(17) yes . . . S1 C4 C3 110.98(13) yes . . . S1 C4 C5 135.67(15) yes . . . C3 C4 C5 113.25(16) yes . . . S2 C5 C4 135.26(15) yes . . . S2 C5 C6 111.28(13) yes . . . C4 C5 C6 113.44(16) yes . . . S3 C6 C5 110.43(13) yes . . . S3 C6 C7 135.07(15) yes . . . C5 C6 C7 114.50(16) yes . . . C6 C7 C8 110.92(17) yes . . . S2 C8 C7 111.61(13) yes . . . S2 C8 C15 119.87(14) yes . . . C7 C8 C15 128.52(17) yes . . . C1 C9 C10 121.11(17) yes . . . C1 C9 C14 120.42(17) yes . . . C10 C9 C14 118.44(18) yes . . . C9 C10 C11 120.4(2) yes . . . C10 C11 C12 121.0(3) yes . . . C11 C12 C13 119.09(19) yes . . . C12 C13 C14 120.48(19) yes . . . C9 C14 C13 120.61(19) yes . . . C8 C15 C16 120.75(17) yes . . . C8 C15 C20 120.34(17) yes . . . C16 C15 C20 118.91(17) yes . . . C15 C16 C17 120.22(19) yes . . . C16 C17 C18 120.11(19) yes . . . C17 C18 C19 120.00(19) yes . . . C18 C19 C20 120.30(19) yes . . . C15 C20 C19 120.46(18) yes . . . C1 C2 H2 124.426 no . . . C3 C2 H2 124.414 no . . . C6 C7 H7 124.534 no . . . C8 C7 H7 124.544 no . . . C9 C10 H10 119.830 no . . . C11 C10 H10 119.811 no . . . C10 C11 H11 119.511 no . . . C12 C11 H11 119.505 no . . . C11 C12 H12 120.447 no . . . C13 C12 H12 120.460 no . . . C12 C13 H13 119.763 no . . . C14 C13 H13 119.760 no . . . C9 C14 H14 119.696 no . . . C13 C14 H14 119.690 no . . . C15 C16 H16 119.886 no . . . C17 C16 H16 119.896 no . . . C16 C17 H17 119.944 no . . . C18 C17 H17 119.949 no . . . C17 C18 H18 119.996 no . . . C19 C18 H18 120.006 no . . . C18 C19 H19 119.854 no . . . C20 C19 H19 119.847 no . . . C15 C20 H20 119.766 no . . . C19 C20 H20 119.775 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C1 S1 C4 C3 0.85(13) no . . . . C1 S1 C4 C5 -175.08(18) no . . . . C4 S1 C1 C2 -0.89(12) no . . . . C4 S1 C1 C9 177.73(13) no . . . . C5 S2 C8 C7 0.13(13) no . . . . C5 S2 C8 C15 179.81(13) no . . . . C8 S2 C5 C4 -178.07(17) no . . . . C8 S2 C5 C6 -0.08(12) no . . . . O1 S3 C3 C2 70.23(19) no . . . . O1 S3 C3 C4 -115.65(12) no . . . . O1 S3 C6 C5 116.18(12) no . . . . O1 S3 C6 C7 -63.36(19) no . . . . O2 S3 C3 C2 -61.90(19) no . . . . O2 S3 C3 C4 112.22(12) no . . . . O2 S3 C6 C5 -111.85(12) no . . . . O2 S3 C6 C7 68.61(19) no . . . . C3 S3 C6 C5 1.41(13) no . . . . C3 S3 C6 C7 -178.13(18) no . . . . C6 S3 C3 C2 -175.42(17) no . . . . C6 S3 C3 C4 -1.30(13) no . . . . S1 C1 C2 C3 0.68(19) no . . . . S1 C1 C9 C10 -2.9(3) no . . . . S1 C1 C9 C14 179.07(11) no . . . . C2 C1 C9 C10 175.43(16) no . . . . C2 C1 C9 C14 -2.6(3) no . . . . C9 C1 C2 C3 -177.80(16) no . . . . C1 C2 C3 S3 173.91(16) no . . . . C1 C2 C3 C4 -0.0(3) no . . . . S3 C3 C4 S1 -176.03(10) no . . . . S3 C3 C4 C5 0.87(19) no . . . . C2 C3 C4 S1 -0.6(2) no . . . . C2 C3 C4 C5 176.27(14) no . . . . S1 C4 C5 S2 -6.0(4) no . . . . S1 C4 C5 C6 176.06(14) no . . . . C3 C4 C5 S2 178.16(16) no . . . . C3 C4 C5 C6 0.2(3) no . . . . S2 C5 C6 S3 -179.63(9) no . . . . S2 C5 C6 C7 0.0(2) no . . . . C4 C5 C6 S3 -1.2(2) no . . . . C4 C5 C6 C7 178.47(14) no . . . . S3 C6 C7 C8 179.61(14) no . . . . C5 C6 C7 C8 0.1(3) no . . . . C6 C7 C8 S2 -0.1(2) no . . . . C6 C7 C8 C15 -179.79(16) no . . . . S2 C8 C15 C16 165.64(12) no . . . . S2 C8 C15 C20 -14.5(3) no . . . . C7 C8 C15 C16 -14.7(3) no . . . . C7 C8 C15 C20 165.12(17) no . . . . C1 C9 C10 C11 -177.94(16) no . . . . C1 C9 C14 C13 179.04(15) no . . . . C10 C9 C14 C13 1.0(3) no . . . . C14 C9 C10 C11 0.1(3) no . . . . C9 C10 C11 C12 -1.7(4) no . . . . C10 C11 C12 C13 2.1(4) no . . . . C11 C12 C13 C14 -1.0(3) no . . . . C12 C13 C14 C9 -0.5(3) no . . . . C8 C15 C16 C17 179.02(16) no . . . . C8 C15 C20 C19 -179.08(15) no . . . . C16 C15 C20 C19 0.8(3) no . . . . C20 C15 C16 C17 -0.8(3) no . . . . C15 C16 C17 C18 0.3(3) no . . . . C16 C17 C18 C19 0.3(3) no . . . . C17 C18 C19 C20 -0.4(3) no . . . . C18 C19 C20 C15 -0.2(3) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 S1 C10 3.088(3) no . . S2 C20 3.083(2) no . . O1 C2 3.562(3) no . . O1 C4 3.562(3) no . . O1 C5 3.560(3) no . . O1 C7 3.532(3) no . . O2 C2 3.492(3) no . . O2 C4 3.524(3) no . . O2 C5 3.526(3) no . . O2 C7 3.558(3) no . . C2 C14 3.029(3) no . . C7 C16 3.060(3) no . . C9 C12 2.798(3) no . . C10 C13 2.758(3) no . . C11 C14 2.754(4) no . . C15 C18 2.788(3) no . . C16 C19 2.773(3) no . . C17 C20 2.770(3) no . . S1 C13 3.554(3) no . 7_556 O1 C2 3.381(3) no . 2_655 O1 C20 3.256(3) no . 4_564 O2 C7 3.598(3) no . 7_656 O2 C18 3.388(3) no . 6_646 O2 C19 3.296(3) no . 6_646 C2 O1 3.381(3) no . 2_655 C2 C11 3.431(4) no . 7_556 C4 C12 3.559(3) no . 7_556 C7 O2 3.598(3) no . 7_656 C9 C9 3.576(3) no . 7_556 C9 C20 3.530(3) no . 3_666 C10 C18 3.552(4) no . 2_656 C11 C2 3.431(4) no . 7_556 C11 C18 3.533(4) no . 2_656 C12 C4 3.559(3) no . 7_556 C13 S1 3.554(3) no . 7_556 C13 C19 3.501(3) no . 3_666 C14 C19 3.525(3) no . 3_666 C14 C20 3.369(3) no . 3_666 C18 O2 3.388(3) no . 6_656 C18 C10 3.552(4) no . 2_656 C18 C11 3.533(4) no . 2_656 C19 O2 3.296(3) no . 6_656 C19 C13 3.501(3) no . 3_666 C19 C14 3.525(3) no . 3_666 C20 O1 3.256(3) no . 4_565 C20 C9 3.530(3) no . 3_666 C20 C14 3.369(3) no . 3_666 S1 H2 3.5120 no . . S1 H10 2.6606 no . . S2 H7 3.5163 no . . S2 H20 2.6606 no . . S3 H2 3.2175 no . . S3 H7 3.2408 no . . O2 H2 3.5788 no . . C1 H10 2.6578 no . . C1 H14 2.6422 no . . C2 H14 2.7211 no . . C4 H2 3.2370 no . . C5 H7 3.2398 no . . C7 H16 2.7749 no . . C8 H16 2.6587 no . . C8 H20 2.6491 no . . C9 H2 2.8493 no . . C9 H11 3.2649 no . . C9 H13 3.2670 no . . C10 H12 3.2605 no . . C10 H14 3.2470 no . . C11 H13 3.2304 no . . C12 H10 3.2532 no . . C12 H14 3.2605 no . . C13 H11 3.2310 no . . C14 H2 2.8551 no . . C14 H10 3.2480 no . . C14 H12 3.2660 no . . C15 H7 2.8578 no . . C15 H17 3.2716 no . . C15 H19 3.2700 no . . C16 H7 2.9041 no . . C16 H18 3.2635 no . . C16 H20 3.2638 no . . C17 H19 3.2522 no . . C18 H16 3.2624 no . . C18 H20 3.2510 no . . C19 H17 3.2512 no . . C20 H16 3.2645 no . . C20 H18 3.2536 no . . H2 H14 2.2708 no . . H7 H16 2.3613 no . . H10 H11 2.3317 no . . H11 H12 2.3178 no . . H12 H13 2.3372 no . . H13 H14 2.3307 no . . H16 H17 2.3372 no . . H17 H18 2.3365 no . . H18 H19 2.3259 no . . H19 H20 2.3296 no . . S1 H20 3.4975 no . 2_656 S2 H13 3.1649 no . 8_555 S3 H7 3.3324 no . 7_656 S3 H16 3.4073 no . 7_656 O1 H2 2.7397 no . 2_655 O1 H7 3.3330 no . 7_656 O1 H14 3.1116 no . 2_655 O1 H16 3.0730 no . 7_656 O1 H19 3.2198 no . 4_564 O1 H20 2.4316 no . 4_564 O2 H7 2.6612 no . 7_656 O2 H11 3.1743 no . 7_556 O2 H12 3.4951 no . 7_556 O2 H16 2.7845 no . 7_656 O2 H17 3.2914 no . 8_454 O2 H18 2.8078 no . 6_646 O2 H19 2.6126 no . 6_646 C1 H20 3.5561 no . 3_666 C2 H11 3.4274 no . 7_556 C3 H11 3.5678 no . 7_556 C3 H12 3.5978 no . 7_556 C4 H12 3.4515 no . 7_556 C5 H13 3.1284 no . 8_555 C6 H13 3.1255 no . 8_555 C7 H13 3.1155 no . 8_555 C7 H14 3.3282 no . 8_555 C7 H19 3.1812 no . 4_564 C8 H13 3.0803 no . 8_555 C8 H14 3.2902 no . 8_555 C9 H20 3.4485 no . 3_666 C11 H18 3.5177 no . 2_656 C11 H18 3.0719 no . 4_464 C12 H12 2.9582 no . 2_555 C12 H13 3.5153 no . 2_555 C12 H18 3.2704 no . 4_464 C13 H12 3.0615 no . 2_555 C13 H19 3.5444 no . 3_666 C14 H19 3.5662 no . 3_666 C14 H20 3.3060 no . 3_666 C15 H10 3.3080 no . 2_656 C15 H14 3.3345 no . 8_555 C16 H2 3.1504 no . 8_555 C16 H10 3.3515 no . 2_656 C16 H14 3.0823 no . 8_555 C16 H17 3.4485 no . 2_756 C17 H2 3.3455 no . 8_555 C17 H10 3.1721 no . 2_656 C17 H11 2.9531 no . 2_656 C17 H17 3.0641 no . 2_756 C18 H10 2.9236 no . 2_656 C18 H11 2.8851 no . 2_656 C18 H11 3.3022 no . 4_665 C18 H12 3.2924 no . 4_665 C19 H7 3.4113 no . 4_565 C19 H10 2.8533 no . 2_656 C19 H13 3.5572 no . 3_666 C20 H10 3.0493 no . 2_656 C20 H14 3.4661 no . 3_666 H2 O1 2.7397 no . 2_655 H2 C16 3.1504 no . 8_454 H2 C17 3.3455 no . 8_454 H2 H11 3.4548 no . 7_556 H2 H16 2.7504 no . 8_454 H2 H17 3.1175 no . 8_454 H2 H20 3.5351 no . 3_666 H7 S3 3.3324 no . 7_656 H7 O1 3.3330 no . 7_656 H7 O2 2.6612 no . 7_656 H7 C19 3.4113 no . 4_564 H7 H7 3.5320 no . 7_656 H7 H14 3.2841 no . 8_555 H7 H19 2.6088 no . 4_564 H10 C15 3.3080 no . 2_656 H10 C16 3.3515 no . 2_656 H10 C17 3.1721 no . 2_656 H10 C18 2.9236 no . 2_656 H10 C19 2.8533 no . 2_656 H10 C20 3.0493 no . 2_656 H10 H18 3.3644 no . 2_656 H10 H19 3.2560 no . 2_656 H10 H20 3.5403 no . 2_656 H11 O2 3.1743 no . 7_556 H11 C2 3.4274 no . 7_556 H11 C3 3.5678 no . 7_556 H11 C17 2.9531 no . 2_656 H11 C18 2.8851 no . 2_656 H11 C18 3.3022 no . 4_464 H11 H2 3.4548 no . 7_556 H11 H17 2.8902 no . 2_656 H11 H18 2.7769 no . 2_656 H11 H18 2.4029 no . 4_464 H12 O2 3.4951 no . 7_556 H12 C3 3.5978 no . 7_556 H12 C4 3.4515 no . 7_556 H12 C12 2.9582 no . 2_555 H12 C13 3.0615 no . 2_555 H12 C18 3.2924 no . 4_464 H12 H12 2.4137 no . 2_555 H12 H13 2.6213 no . 2_555 H12 H18 2.8128 no . 4_464 H13 S2 3.1649 no . 8_454 H13 C5 3.1284 no . 8_454 H13 C6 3.1255 no . 8_454 H13 C7 3.1155 no . 8_454 H13 C8 3.0803 no . 8_454 H13 C12 3.5153 no . 2_555 H13 C19 3.5572 no . 3_666 H13 H12 2.6213 no . 2_555 H13 H19 3.3849 no . 3_666 H14 O1 3.1116 no . 2_655 H14 C7 3.3282 no . 8_454 H14 C8 3.2902 no . 8_454 H14 C15 3.3345 no . 8_454 H14 C16 3.0823 no . 8_454 H14 C20 3.4661 no . 3_666 H14 H7 3.2841 no . 8_454 H14 H16 2.7548 no . 8_454 H14 H19 3.4299 no . 3_666 H14 H20 3.1858 no . 3_666 H16 S3 3.4073 no . 7_656 H16 O1 3.0730 no . 7_656 H16 O2 2.7845 no . 7_656 H16 H2 2.7504 no . 8_555 H16 H14 2.7548 no . 8_555 H16 H17 3.2264 no . 2_756 H17 O2 3.2914 no . 8_555 H17 C16 3.4485 no . 2_756 H17 C17 3.0641 no . 2_756 H17 H2 3.1175 no . 8_555 H17 H11 2.8902 no . 2_656 H17 H16 3.2264 no . 2_756 H17 H17 2.4871 no . 2_756 H18 O2 2.8078 no . 6_656 H18 C11 3.5177 no . 2_656 H18 C11 3.0719 no . 4_665 H18 C12 3.2704 no . 4_665 H18 H10 3.3644 no . 2_656 H18 H11 2.7769 no . 2_656 H18 H11 2.4029 no . 4_665 H18 H12 2.8128 no . 4_665 H18 H18 3.2240 no . 3_767 H19 O1 3.2198 no . 4_565 H19 O2 2.6126 no . 6_656 H19 C7 3.1812 no . 4_565 H19 C13 3.5444 no . 3_666 H19 C14 3.5662 no . 3_666 H19 H7 2.6088 no . 4_565 H19 H10 3.2560 no . 2_656 H19 H13 3.3849 no . 3_666 H19 H14 3.4299 no . 3_666 H20 S1 3.4975 no . 2_656 H20 O1 2.4316 no . 4_565 H20 C1 3.5561 no . 3_666 H20 C9 3.4485 no . 3_666 H20 C14 3.3060 no . 3_666 H20 H2 3.5351 no . 3_666 H20 H10 3.5403 no . 2_656 H20 H14 3.1858 no . 3_666 #============================================================================== #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #==============================================================================