# Electronic Supplementary Material (ESI) for Organic & Biomolecular 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_20120313Sakai _database_code_depnum_ccdc_archive 'CCDC 874880' #TrackingRef '6dCIF.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C25 H24 O2 S' _chemical_formula_moiety 'C25 H24 O2 S' _chemical_formula_weight 388.52 _chemical_melting_point ? _chemical_absolute_configuration ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2+X,1/2-Y,-Z 3 -X,1/2+Y,1/2-Z 4 1/2-X,-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 5.9235(3) _cell_length_b 8.7289(5) _cell_length_c 41.0305(19) _cell_angle_alpha 90.0000 _cell_angle_beta 90.0000 _cell_angle_gamma 90.0000 _cell_volume 2121.52(19) _cell_formula_units_Z 4 _cell_measurement_reflns_used 14120 _cell_measurement_theta_min 3.06 _cell_measurement_theta_max 27.41 _cell_measurement_temperature 296 #------------------------------------------------------------------------------ _exptl_crystal_description unknown _exptl_crystal_colour unknown _exptl_crystal_size_max 0.100 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.100 _exptl_crystal_density_diffrn 1.216 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824.00 _exptl_absorpt_coefficient_mu 0.169 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR (Rigaku, 1995)' _exptl_absorpt_correction_T_min 0.740 _exptl_absorpt_correction_T_max 0.983 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 296 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_reflns_number 21030 _diffrn_reflns_av_R_equivalents 0.0483 _diffrn_reflns_theta_max 27.44 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -53 _diffrn_reflns_limit_l_max 52 _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 4837 _reflns_number_gt 3135 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.1070 _refine_ls_wR_factor_ref 0.3185 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 4837 _refine_ls_number_parameters 113 _refine_ls_goodness_of_fit_ref 2.022 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.1000P)^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 0.655 _refine_diff_density_max 0.950 _refine_diff_density_min -1.170 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 2008 Friedel Pairs' _refine_ls_abs_structure_Flack -0.1(3) 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 0.0745(3) 0.18230(18) 0.59757(3) 0.0640(5) Uiso 1.0 4 d . . . O2 O -0.4628(7) 0.2709(5) 0.80575(9) 0.0646(10) Uiso 1.0 4 d . . . O3 O 0.2185(8) 0.4173(5) 0.69184(9) 0.0699(11) Uiso 1.0 4 d . . . C4 C -0.2888(9) 0.2284(6) 0.71944(11) 0.0494(11) Uiso 1.0 4 d . . . C5 C -0.0951(8) 0.3203(6) 0.71991(11) 0.0487(11) Uiso 1.0 4 d . . . C6 C -0.3571(9) 0.1453(7) 0.68865(12) 0.0559(13) Uiso 1.0 4 d . . . C7 C 0.0469(8) 0.3405(6) 0.69113(11) 0.0498(11) Uiso 1.0 4 d . . . C8 C 0.0905(9) 0.3276(6) 0.62962(11) 0.0529(12) Uiso 1.0 4 d . . . C9 C -0.4208(9) 0.2100(6) 0.74784(11) 0.0518(12) Uiso 1.0 4 d . . . C10 C 0.0006(9) 0.4837(6) 0.61993(12) 0.0502(12) Uiso 1.0 4 d . . . C11 C -0.2767(9) 0.2328(7) 0.65840(12) 0.0531(12) Uiso 1.0 4 d . . . C12 C -0.3530(9) 0.2834(7) 0.77657(11) 0.0511(12) Uiso 1.0 4 d . . . C13 C -0.0181(9) 0.2559(7) 0.65976(11) 0.0497(12) Uiso 1.0 4 d . . . C14 C -0.1646(10) 0.3787(7) 0.77670(13) 0.0626(15) Uiso 1.0 4 d . . . C15 C 0.1289(11) 0.6121(7) 0.62833(13) 0.0643(15) Uiso 1.0 4 d . . . C16 C 0.3046(9) 0.1498(7) 0.54125(12) 0.0551(13) Uiso 1.0 4 d . . . C17 C -0.0321(10) 0.3947(7) 0.74926(13) 0.0579(13) Uiso 1.0 4 d . . . C18 C -0.2016(10) 0.5014(7) 0.60312(13) 0.0621(14) Uiso 1.0 4 d . . . C19 C -0.2776(11) 0.6449(8) 0.59480(14) 0.0707(16) Uiso 1.0 4 d . . . C20 C 0.1546(12) 0.1206(9) 0.51563(15) 0.0770(18) Uiso 1.0 4 d . . . C21 C 0.0519(14) 0.7576(9) 0.61953(17) 0.088(2) Uiso 1.0 4 d . . . C22 C -0.1551(14) 0.7761(10) 0.60247(17) 0.091(2) Uiso 1.0 4 d . . . C23 C -0.6485(11) 0.1622(8) 0.80761(14) 0.0681(15) Uiso 1.0 4 d . . . C24 C 0.2446(12) 0.2719(8) 0.56598(15) 0.0741(17) Uiso 1.0 4 d . . . C25 C 0.5054(13) 0.0698(9) 0.54321(16) 0.0790(18) Uiso 1.0 4 d . . . C26 C 0.2053(15) 0.0081(11) 0.4919(2) 0.101(3) Uiso 1.0 4 d . . . C27 C 0.4144(16) -0.0732(11) 0.4950(2) 0.100(3) Uiso 1.0 4 d . . . C28 C 0.5588(15) -0.0415(10) 0.52082(19) 0.097(3) Uiso 1.0 4 d . . . H8 H 0.2509 0.3412 0.6347 0.0634 Uiso 1.0 4 calc R . . H13 H 0.0471 0.1531 0.6617 0.0597 Uiso 1.0 4 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 #Not supplied ? ? ? ? ? ? ? #============================================================================== _computing_data_collection 'RAPID AUTO (Rigaku, ????)' _computing_cell_refinement 'RAPID AUTO' _computing_data_reduction 'RAPID AUTO' _computing_structure_solution 'SIR2002 (Burla, et al., 2003)' _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 C8 1.829(5) yes . . S1 C24 1.818(7) yes . . O2 C12 1.367(6) yes . . O2 C23 1.455(8) yes . . O3 C7 1.218(7) yes . . C4 C5 1.400(7) yes . . C4 C6 1.512(7) yes . . C4 C9 1.412(7) yes . . C5 C7 1.460(7) yes . . C5 C17 1.418(8) yes . . C6 C11 1.534(8) yes . . C7 C13 1.533(7) yes . . C8 C10 1.516(8) yes . . C8 C13 1.528(7) yes . . C9 C12 1.400(7) yes . . C10 C15 1.397(8) yes . . C10 C18 1.391(8) yes . . C11 C13 1.546(8) yes . . C12 C14 1.392(8) yes . . C14 C17 1.379(8) yes . . C15 C21 1.397(10) yes . . C16 C20 1.400(9) yes . . C16 C24 1.514(9) yes . . C16 C25 1.382(9) yes . . C18 C19 1.374(10) yes . . C19 C22 1.392(11) yes . . C20 C26 1.414(11) yes . . C21 C22 1.421(11) yes . . C25 C28 1.374(11) yes . . C26 C27 1.433(13) yes . . C27 C28 1.389(12) yes . . C8 H8 0.980 no . . C13 H13 0.980 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 C8 S1 C24 100.7(3) yes . . . C12 O2 C23 117.2(5) yes . . . C5 C4 C6 120.4(5) yes . . . C5 C4 C9 120.5(5) yes . . . C6 C4 C9 119.1(5) yes . . . C4 C5 C7 122.0(5) yes . . . C4 C5 C17 119.3(5) yes . . . C7 C5 C17 118.7(5) yes . . . C4 C6 C11 110.7(5) yes . . . O3 C7 C5 121.8(5) yes . . . O3 C7 C13 119.7(5) yes . . . C5 C7 C13 118.4(5) yes . . . S1 C8 C10 114.6(4) yes . . . S1 C8 C13 106.0(4) yes . . . C10 C8 C13 115.6(5) yes . . . C4 C9 C12 118.9(5) yes . . . C8 C10 C15 117.7(5) yes . . . C8 C10 C18 122.2(5) yes . . . C15 C10 C18 120.1(6) yes . . . C6 C11 C13 110.1(4) yes . . . O2 C12 C9 124.4(5) yes . . . O2 C12 C14 115.2(5) yes . . . C9 C12 C14 120.4(5) yes . . . C7 C13 C8 112.1(5) yes . . . C7 C13 C11 110.0(4) yes . . . C8 C13 C11 116.2(4) yes . . . C12 C14 C17 120.9(5) yes . . . C10 C15 C21 119.2(6) yes . . . C20 C16 C24 118.9(6) yes . . . C20 C16 C25 119.9(6) yes . . . C24 C16 C25 121.3(6) yes . . . C5 C17 C14 119.8(5) yes . . . C10 C18 C19 120.5(6) yes . . . C18 C19 C22 121.5(6) yes . . . C16 C20 C26 120.5(7) yes . . . C15 C21 C22 120.8(7) yes . . . C19 C22 C21 117.9(8) yes . . . S1 C24 C16 107.8(5) yes . . . C16 C25 C28 121.1(7) yes . . . C20 C26 C27 117.8(8) yes . . . C26 C27 C28 120.1(8) yes . . . C25 C28 C27 120.6(8) yes . . . S1 C8 H8 106.655 no . . . C10 C8 H8 106.661 no . . . C13 C8 H8 106.656 no . . . C7 C13 H13 105.928 no . . . C8 C13 H13 105.890 no . . . C11 C13 H13 105.913 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 C8 S1 C24 C16 164.4(4) no . . . . C24 S1 C8 C10 59.3(4) no . . . . C24 S1 C8 C13 -171.9(4) no . . . . C23 O2 C12 C9 6.4(7) no . . . . C23 O2 C12 C14 -174.7(4) no . . . . C5 C4 C6 C11 -28.7(7) no . . . . C6 C4 C5 C7 0.4(8) no . . . . C6 C4 C5 C17 -178.8(4) no . . . . C5 C4 C9 C12 -0.9(7) no . . . . C9 C4 C5 C7 179.3(4) no . . . . C9 C4 C5 C17 0.1(8) no . . . . C6 C4 C9 C12 178.0(4) no . . . . C9 C4 C6 C11 152.4(5) no . . . . C4 C5 C7 O3 -178.1(5) no . . . . C4 C5 C7 C13 -1.0(7) no . . . . C4 C5 C17 C14 -1.5(8) no . . . . C7 C5 C17 C14 179.3(5) no . . . . C17 C5 C7 O3 1.1(8) no . . . . C17 C5 C7 C13 178.2(4) no . . . . C4 C6 C11 C13 56.9(6) no . . . . O3 C7 C13 C8 -22.5(7) no . . . . O3 C7 C13 C11 -153.4(5) no . . . . C5 C7 C13 C8 160.3(4) no . . . . C5 C7 C13 C11 29.4(6) no . . . . S1 C8 C10 C15 -134.9(4) no . . . . S1 C8 C10 C18 44.8(6) no . . . . S1 C8 C13 C7 161.9(3) no . . . . S1 C8 C13 C11 -70.4(5) no . . . . C10 C8 C13 C7 -69.9(5) no . . . . C10 C8 C13 C11 57.8(6) no . . . . C13 C8 C10 C15 101.3(5) no . . . . C13 C8 C10 C18 -79.0(6) no . . . . C4 C9 C12 O2 -178.1(5) no . . . . C4 C9 C12 C14 3.0(8) no . . . . C8 C10 C15 C21 179.5(4) no . . . . C8 C10 C18 C19 179.9(4) no . . . . C15 C10 C18 C19 -0.4(8) no . . . . C18 C10 C15 C21 -0.2(8) no . . . . C6 C11 C13 C7 -57.1(6) no . . . . C6 C11 C13 C8 174.1(4) no . . . . O2 C12 C14 C17 176.5(5) no . . . . C9 C12 C14 C17 -4.5(9) no . . . . C12 C14 C17 C5 3.7(9) no . . . . C10 C15 C21 C22 0.5(9) no . . . . C20 C16 C24 S1 87.1(6) no . . . . C24 C16 C20 C26 179.7(5) no . . . . C20 C16 C25 C28 -1.7(10) no . . . . C25 C16 C20 C26 1.0(9) no . . . . C24 C16 C25 C28 179.6(5) no . . . . C25 C16 C24 S1 -94.2(7) no . . . . C10 C18 C19 C22 0.8(9) no . . . . C18 C19 C22 C21 -0.5(10) no . . . . C16 C20 C26 C27 -0.4(11) no . . . . C15 C21 C22 C19 -0.2(10) no . . . . C16 C25 C28 C27 1.9(11) no . . . . C20 C26 C27 C28 0.6(12) no . . . . C26 C27 C28 C25 -1.3(13) 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 C11 3.279(6) no . . S1 C18 3.238(7) no . . S1 C20 3.438(7) no . . S1 C25 3.529(8) no . . O3 C8 2.776(6) no . . O3 C10 3.272(7) no . . O3 C15 3.157(7) no . . O3 C17 2.792(7) no . . C4 C13 2.937(7) no . . C4 C14 2.790(8) no . . C5 C11 2.848(7) no . . C5 C12 2.800(7) no . . C6 C7 2.939(8) no . . C7 C10 3.189(7) no . . C7 C15 3.535(8) no . . C9 C17 2.811(8) no . . C9 C23 2.830(8) no . . C10 C11 3.160(8) no . . C10 C22 2.807(10) no . . C10 C24 3.226(9) no . . C11 C18 3.292(8) no . . C13 C15 3.477(8) no . . C13 C18 3.343(8) no . . C15 C19 2.788(9) no . . C16 C27 2.795(11) no . . C18 C21 2.777(10) no . . C20 C28 2.790(12) no . . C25 C26 2.806(11) no . . O2 O3 3.411(6) no . 3_546 O2 C6 3.445(7) no . 3_456 O3 O2 3.411(6) no . 3_556 O3 C4 3.538(7) no . 1_655 O3 C6 3.460(7) no . 1_655 O3 C12 3.539(7) no . 3_556 O3 C23 3.326(8) no . 3_556 C4 O3 3.538(7) no . 1_455 C5 C23 3.534(9) no . 3_456 C6 O2 3.445(7) no . 3_446 C6 O3 3.460(7) no . 1_455 C12 O3 3.539(7) no . 3_546 C23 O3 3.326(8) no . 3_546 C23 C5 3.534(9) no . 3_446 S1 H13 2.6478 no . . O3 H8 2.4450 no . . O3 H13 2.8069 no . . C4 H13 3.1635 no . . C5 H13 2.9235 no . . C6 H13 2.6384 no . . C7 H8 2.6126 no . . C10 H13 3.3672 no . . C11 H8 3.4071 no . . C15 H8 2.4864 no . . C18 H8 3.2887 no . . C24 H8 2.8833 no . . H8 H13 2.3195 no . . C11 H8 3.1101 no . 1_455 C14 H13 3.5515 no . 3_556 H8 C11 3.1101 no . 1_655 H13 C14 3.5515 no . 3_546 data_20110506Sakai _database_code_depnum_ccdc_archive 'CCDC 874881' #TrackingRef '8aCIF.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C17 H18 O S' _chemical_formula_moiety 'C17 H18 O S' _chemical_formula_weight 270.39 _chemical_melting_point ? _chemical_absolute_configuration ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2+X,1/2-Y,-Z 3 -X,1/2+Y,1/2-Z 4 1/2-X,-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 5.7153(8) _cell_length_b 7.9637(12) _cell_length_c 32.145(5) _cell_angle_alpha 90.0000 _cell_angle_beta 90.0000 _cell_angle_gamma 90.0000 _cell_volume 1463.1(4) _cell_formula_units_Z 4 _cell_measurement_reflns_used 7128 _cell_measurement_theta_min 3.19 _cell_measurement_theta_max 27.50 _cell_measurement_temperature 296 #------------------------------------------------------------------------------ _exptl_crystal_description unknown _exptl_crystal_colour unknown _exptl_crystal_size_max 0.100 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.100 _exptl_crystal_density_diffrn 1.227 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576.00 _exptl_absorpt_coefficient_mu 0.211 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR (Rigaku, 1995)' _exptl_absorpt_correction_T_min 0.644 _exptl_absorpt_correction_T_max 0.979 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 296 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_reflns_number 14558 _diffrn_reflns_av_R_equivalents 0.0643 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 41 _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 3355 _reflns_number_gt 1953 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0953 _refine_ls_wR_factor_ref 0.2809 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment undef _refine_ls_number_reflns 3355 _refine_ls_number_parameters 77 _refine_ls_goodness_of_fit_ref 1.650 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.439 _refine_diff_density_max 0.620 _refine_diff_density_min -0.650 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 1372 Friedel Pairs' _refine_ls_abs_structure_Flack 0.1(3) 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 0.4274(3) 0.20331(19) 0.36815(5) 0.0586(5) Uiso 1.0 4 d . . . O2 O 0.5294(7) -0.2243(6) 0.40594(12) 0.0615(11) Uiso 1.0 4 d . . . C3 C 0.6585(9) -0.0490(7) 0.45978(15) 0.0472(12) Uiso 1.0 4 d . . . C4 C 0.6565(9) -0.1057(7) 0.41568(15) 0.0471(12) Uiso 1.0 4 d . . . C5 C 0.6561(9) 0.4598(7) 0.32639(15) 0.0480(13) Uiso 1.0 4 d . . . C6 C 0.8389(10) 0.0507(8) 0.47605(17) 0.0553(14) Uiso 1.0 4 d . . . C7 C 0.6285(10) 0.0472(8) 0.34931(17) 0.0564(14) Uiso 1.0 4 d . . . C8 C 0.7981(9) -0.0164(7) 0.38232(16) 0.0513(14) Uiso 1.0 4 d . . . C9 C 0.6160(10) 0.3884(8) 0.36913(18) 0.0630(15) Uiso 1.0 4 d . . . C10 C 0.4936(10) 0.5671(8) 0.30844(18) 0.0603(15) Uiso 1.0 4 d . . . C11 C 0.4689(11) -0.0485(9) 0.52735(19) 0.0644(16) Uiso 1.0 4 d . . . C12 C 0.6516(11) 0.0504(9) 0.54278(19) 0.0665(16) Uiso 1.0 4 d . . . C13 C 0.8350(10) 0.1014(8) 0.51869(18) 0.0625(16) Uiso 1.0 4 d . . . C14 C 0.5329(12) 0.6317(10) 0.2686(3) 0.0772(18) Uiso 1.0 4 d . . . C15 C 0.4722(9) -0.0997(7) 0.48564(17) 0.0550(14) Uiso 1.0 4 d . . . C16 C 0.8653(11) 0.4250(8) 0.30536(19) 0.0653(16) Uiso 1.0 4 d . . . C17 C 0.7423(14) 0.5905(10) 0.24702(19) 0.0787(19) Uiso 1.0 4 d . . . C18 C 0.9045(13) 0.4863(9) 0.2653(3) 0.0775(19) Uiso 1.0 4 d . . . C19 C 0.9695(12) -0.1443(9) 0.3633(2) 0.0754(18) Uiso 1.0 4 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 #Not supplied ? ? ? ? ? ? ? #============================================================================== _computing_data_collection 'RAPID AUTO (Rigaku, ????)' _computing_cell_refinement 'RAPID AUTO' _computing_data_reduction 'RAPID AUTO' _computing_structure_solution 'SIR2002 (Burla, et al., 2003)' _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 C7 1.798(6) yes . . S1 C9 1.826(7) yes . . O2 C4 1.232(7) yes . . C3 C4 1.488(7) yes . . C3 C6 1.402(8) yes . . C3 C15 1.410(8) yes . . C4 C8 1.520(8) yes . . C5 C9 1.504(8) yes . . C5 C10 1.388(8) yes . . C5 C16 1.401(8) yes . . C6 C13 1.429(8) yes . . C7 C8 1.524(8) yes . . C8 C19 1.540(9) yes . . C10 C14 1.399(10) yes . . C11 C12 1.399(9) yes . . C11 C15 1.402(9) yes . . C12 C13 1.365(9) yes . . C14 C17 1.421(10) yes . . C16 C18 1.396(10) yes . . C17 C18 1.376(11) yes . . 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 C7 S1 C9 100.8(3) yes . . . C4 C3 C6 122.2(5) yes . . . C4 C3 C15 118.0(5) yes . . . C6 C3 C15 119.8(5) yes . . . O2 C4 C3 118.6(5) yes . . . O2 C4 C8 119.6(5) yes . . . C3 C4 C8 121.7(5) yes . . . C9 C5 C10 120.7(5) yes . . . C9 C5 C16 119.7(5) yes . . . C10 C5 C16 119.5(5) yes . . . C3 C6 C13 120.4(5) yes . . . S1 C7 C8 113.7(4) yes . . . C4 C8 C7 107.9(5) yes . . . C4 C8 C19 108.0(5) yes . . . C7 C8 C19 110.3(5) yes . . . S1 C9 C5 112.3(4) yes . . . C5 C10 C14 120.0(6) yes . . . C12 C11 C15 119.6(6) yes . . . C11 C12 C13 122.7(6) yes . . . C6 C13 C12 118.1(6) yes . . . C10 C14 C17 119.8(6) yes . . . C3 C15 C11 119.4(5) yes . . . C5 C16 C18 120.9(6) yes . . . C14 C17 C18 119.9(7) yes . . . C16 C18 C17 119.8(7) yes . . . 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 C7 S1 C9 C5 76.4(4) no . . . . C9 S1 C7 C8 77.5(4) no . . . . C4 C3 C6 C13 -179.5(5) no . . . . C6 C3 C4 O2 162.1(5) no . . . . C6 C3 C4 C8 -20.7(8) no . . . . C4 C3 C15 C11 180.0(5) no . . . . C15 C3 C4 O2 -17.3(7) no . . . . C15 C3 C4 C8 159.9(5) no . . . . C6 C3 C15 C11 0.5(8) no . . . . C15 C3 C6 C13 -0.1(8) no . . . . O2 C4 C8 C7 57.1(6) no . . . . O2 C4 C8 C19 -62.2(6) no . . . . C3 C4 C8 C7 -120.1(5) no . . . . C3 C4 C8 C19 120.6(5) no . . . . C9 C5 C10 C14 -179.7(5) no . . . . C10 C5 C9 S1 82.9(6) no . . . . C9 C5 C16 C18 178.5(5) no . . . . C16 C5 C9 S1 -100.6(6) no . . . . C10 C5 C16 C18 -5.0(9) no . . . . C16 C5 C10 C14 3.9(8) no . . . . C3 C6 C13 C12 -0.1(9) no . . . . S1 C7 C8 C4 64.3(5) no . . . . S1 C7 C8 C19 -177.9(3) no . . . . C5 C10 C14 C17 -1.6(9) no . . . . C12 C11 C15 C3 -0.7(9) no . . . . C15 C11 C12 C13 0.6(10) no . . . . C11 C12 C13 C6 -0.2(10) no . . . . C10 C14 C17 C18 0.5(11) no . . . . C5 C16 C18 C17 3.9(10) no . . . . C14 C17 C18 C16 -1.6(11) 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 C4 3.179(6) no . . S1 C10 3.496(7) no . . O2 C7 2.883(7) no . . O2 C15 2.767(7) no . . O2 C19 2.935(8) no . . C3 C12 2.783(8) no . . C5 C7 3.371(8) no . . C5 C17 2.799(8) no . . C6 C8 3.069(8) no . . C6 C11 2.795(8) no . . C7 C16 3.589(9) no . . C8 C9 3.414(9) no . . C10 C18 2.802(9) no . . C13 C15 2.828(8) no . . C14 C16 2.778(10) no . . O2 C9 3.340(8) no . 1_545 O2 C10 3.553(7) no . 1_545 O2 C19 3.539(8) no . 1_455 C9 O2 3.340(8) no . 1_565 C10 O2 3.553(7) no . 1_565 C19 O2 3.539(8) no . 1_655 #============================================================================== #============================================================================== # 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 #==============================================================================