data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Richard Jackson' 'William Clegg' 'Sara F.C. Dunn' 'Andrew McCamley' _publ_contact_author_name 'Prof Richard Jackson' _publ_contact_author_address ; Chemistry University of Sheffield Dainton Building Brook Hill Sheffield S3 7HF UNITED KINGDOM ; _publ_contact_author_email R.F.W.JACKSON@SHEF.AC.UK _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Synthesis and Crystal Structures of 2-Substituted-2-Phenylsulfonyloxiranes: Evidence for a Generalised Anomeric Effect in 2-Phenylsulfonyloxiranes ; data_5 _database_code_CSD 203327 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H13 N O3 S' _chemical_formula_weight 251.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n a 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 12.419(1) _cell_length_b 10.721(1) _cell_length_c 9.853(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1311.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 32 _cell_measurement_theta_min 20.0 _cell_measurement_theta_max 35.0 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 2.178 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe-Siemens four-circle diffractometer' _diffrn_measurement_method '\w/\q scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3239 _diffrn_reflns_av_R_equivalents 0.0400 _diffrn_reflns_av_sigmaI/netI 0.0233 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 5.45 _diffrn_reflns_theta_max 62.53 _reflns_number_total 2079 _reflns_number_gt 2040 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Stoe DIF4' _computing_cell_refinement 'Stoe DIF4' _computing_data_reduction 'local programs' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.1220P)^2^+0.1639P] 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 0.0083(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(3) _refine_ls_number_reflns 2079 _refine_ls_number_parameters 155 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0610 _refine_ls_R_factor_gt 0.0605 _refine_ls_wR_factor_ref 0.1609 _refine_ls_wR_factor_gt 0.1600 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _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 O1 O 0.47264(16) 0.4512(2) 0.2045(3) 0.0698(6) Uani 1 1 d . . . C2 C 0.5746(2) 0.4299(3) 0.2620(3) 0.0535(7) Uani 1 1 d . . . C3 C 0.5073(2) 0.5320(3) 0.3149(4) 0.0608(7) Uani 1 1 d . . . H3 H 0.4731 0.5155 0.4027 0.073 Uiso 1 1 calc R . . C4 C 0.5280(3) 0.6665(3) 0.2850(4) 0.0652(8) Uani 1 1 d . . . H4 H 0.5547 0.6743 0.1918 0.078 Uiso 1 1 calc R . . C5 C 0.6134(4) 0.7147(4) 0.3823(6) 0.0857(12) Uani 1 1 d . . . H5A H 0.6279 0.8008 0.3630 0.129 Uiso 1 1 calc R . . H5B H 0.6782 0.6669 0.3714 0.129 Uiso 1 1 calc R . . H5C H 0.5880 0.7068 0.4739 0.129 Uiso 1 1 calc R . . C6 C 0.4219(3) 0.7395(5) 0.2981(6) 0.0901(12) Uani 1 1 d . . . H6A H 0.4347 0.8259 0.2783 0.135 Uiso 1 1 calc R . . H6B H 0.3948 0.7315 0.3889 0.135 Uiso 1 1 calc R . . H6C H 0.3701 0.7066 0.2352 0.135 Uiso 1 1 calc R . . S7 S 0.58704(7) 0.29231(6) 0.36623(8) 0.0661(3) Uani 1 1 d . . . O8 O 0.4866(3) 0.2825(3) 0.4359(3) 0.0962(11) Uani 1 1 d . . . O9 O 0.6857(3) 0.3076(3) 0.4374(4) 0.1014(11) Uani 1 1 d . . . C10 C 0.6001(2) 0.1687(3) 0.2518(4) 0.0568(8) Uani 1 1 d . . . C11 C 0.5077(2) 0.1191(3) 0.1933(4) 0.0632(8) Uani 1 1 d . . . H11 H 0.4399 0.1502 0.2150 0.076 Uiso 1 1 calc R . . C12 C 0.5192(3) 0.0223(3) 0.1020(4) 0.0695(9) Uani 1 1 d . . . H12 H 0.4587 -0.0116 0.0604 0.083 Uiso 1 1 calc R . . C13 C 0.6192(3) -0.0241(3) 0.0723(4) 0.0682(8) Uani 1 1 d . . . H13 H 0.6258 -0.0902 0.0117 0.082 Uiso 1 1 calc R . . C14 C 0.7098(3) 0.0256(3) 0.1307(5) 0.0758(10) Uani 1 1 d . . . H14 H 0.7773 -0.0060 0.1087 0.091 Uiso 1 1 calc R . . C15 C 0.7007(2) 0.1226(3) 0.2220(4) 0.0694(8) Uani 1 1 d . . . H15 H 0.7617 0.1562 0.2629 0.083 Uiso 1 1 calc R . . C16 C 0.6664(3) 0.4533(3) 0.1734(4) 0.0687(9) Uani 1 1 d . . . N17 N 0.7382(3) 0.4672(5) 0.1055(6) 0.1168(17) 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 O1 0.0536(11) 0.0682(13) 0.0876(15) -0.0165(12) -0.0088(11) 0.0004(9) C2 0.0501(13) 0.0507(16) 0.0598(15) -0.0053(13) 0.0035(11) -0.0054(11) C3 0.0606(14) 0.0544(16) 0.0675(16) -0.0060(14) 0.0077(14) -0.0003(12) C4 0.077(2) 0.0536(17) 0.0645(19) 0.0026(14) 0.0068(15) 0.0019(14) C5 0.102(3) 0.063(2) 0.093(3) -0.0041(19) -0.007(3) -0.0131(18) C6 0.098(3) 0.069(2) 0.103(3) -0.003(3) 0.004(2) 0.0203(19) S7 0.0935(6) 0.0476(4) 0.0571(5) -0.0053(3) -0.0013(4) -0.0054(3) O8 0.138(3) 0.0625(15) 0.088(2) -0.0108(13) 0.046(2) -0.0183(15) O9 0.137(3) 0.0634(15) 0.103(2) -0.0152(14) -0.051(2) 0.0015(15) C10 0.0606(15) 0.0439(15) 0.066(2) -0.0022(14) -0.0028(13) -0.0029(12) C11 0.0541(15) 0.0567(17) 0.079(2) -0.0072(16) 0.0006(14) -0.0016(12) C12 0.0669(19) 0.0604(19) 0.081(2) -0.0137(15) -0.0105(16) -0.0144(14) C13 0.075(2) 0.0544(17) 0.075(2) -0.0135(16) 0.0030(17) -0.0007(15) C14 0.0616(17) 0.0631(19) 0.103(3) -0.0134(18) 0.0066(19) 0.0056(15) C15 0.0565(16) 0.0619(18) 0.090(2) -0.0077(16) -0.0084(18) -0.0053(14) C16 0.0598(17) 0.0620(17) 0.084(2) 0.0001(15) 0.0136(17) 0.0001(14) N17 0.090(2) 0.110(3) 0.150(4) 0.010(3) 0.056(3) 0.001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.405(4) . ? O1 C3 1.455(4) . ? C2 C3 1.473(4) . ? C2 S7 1.804(3) . ? C2 C16 1.457(4) . ? C3 C4 1.494(5) . ? C4 C5 1.520(6) . ? C4 C6 1.537(5) . ? S7 O8 1.427(3) . ? S7 O9 1.421(3) . ? S7 C10 1.747(3) . ? C10 C11 1.391(4) . ? C10 C15 1.376(4) . ? C11 C12 1.381(5) . ? C12 C13 1.369(5) . ? C13 C14 1.372(5) . ? C14 C15 1.380(6) . ? C16 N17 1.125(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 O1 C3 61.9(2) . . ? O1 C2 C3 60.7(2) . . ? O1 C2 S7 116.1(2) . . ? O1 C2 C16 115.8(3) . . ? C3 C2 S7 117.1(2) . . ? C3 C2 C16 121.9(3) . . ? S7 C2 C16 114.5(2) . . ? O1 C3 C2 57.36(19) . . ? O1 C3 C4 118.5(3) . . ? C2 C3 C4 123.4(3) . . ? C3 C4 C5 108.9(3) . . ? C3 C4 C6 109.1(3) . . ? C5 C4 C6 111.8(4) . . ? C2 S7 O8 105.04(17) . . ? C2 S7 O9 105.11(16) . . ? C2 S7 C10 105.11(16) . . ? O8 S7 O9 121.6(3) . . ? O8 S7 C10 109.60(16) . . ? O9 S7 C10 109.03(17) . . ? S7 C10 C11 118.8(2) . . ? S7 C10 C15 119.7(2) . . ? C11 C10 C15 121.6(3) . . ? C10 C11 C12 118.2(3) . . ? C11 C12 C13 120.4(3) . . ? C12 C13 C14 120.8(3) . . ? C13 C14 C15 120.0(3) . . ? C10 C15 C14 119.0(3) . . ? C2 C16 N17 177.6(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 O1 C2 S7 107.8(3) . . . . ? C3 O1 C2 C16 -113.6(3) . . . . ? C2 O1 C3 C4 113.3(3) . . . . ? O1 C2 C3 C4 -104.9(4) . . . . ? S7 C2 C3 O1 -106.2(2) . . . . ? S7 C2 C3 C4 148.9(3) . . . . ? C16 C2 C3 O1 103.8(3) . . . . ? C16 C2 C3 C4 -1.1(5) . . . . ? O1 C3 C4 C5 -150.8(3) . . . . ? O1 C3 C4 C6 86.9(4) . . . . ? C2 C3 C4 C5 -82.9(4) . . . . ? C2 C3 C4 C6 154.8(4) . . . . ? O1 C2 S7 O8 -36.7(3) . . . . ? O1 C2 S7 O9 -166.1(3) . . . . ? O1 C2 S7 C10 78.9(3) . . . . ? C3 C2 S7 O8 32.1(3) . . . . ? C3 C2 S7 O9 -97.3(3) . . . . ? C3 C2 S7 C10 147.7(2) . . . . ? C16 C2 S7 O8 -175.8(3) . . . . ? C16 C2 S7 O9 54.8(3) . . . . ? C16 C2 S7 C10 -60.2(3) . . . . ? C2 S7 C10 C11 -81.9(3) . . . . ? C2 S7 C10 C15 98.3(3) . . . . ? O8 S7 C10 C11 30.5(3) . . . . ? O8 S7 C10 C15 -149.2(3) . . . . ? O9 S7 C10 C11 165.8(3) . . . . ? O9 S7 C10 C15 -13.9(4) . . . . ? S7 C10 C11 C12 179.4(3) . . . . ? C15 C10 C11 C12 -0.9(5) . . . . ? C10 C11 C12 C13 1.0(6) . . . . ? C11 C12 C13 C14 -1.0(6) . . . . ? C12 C13 C14 C15 0.9(6) . . . . ? S7 C10 C15 C14 -179.5(3) . . . . ? C11 C10 C15 C14 0.8(6) . . . . ? C13 C14 C15 C10 -0.7(6) . . . . ? O1 C2 C16 N17 -120(11) . . . . ? C3 C2 C16 N17 169(11) . . . . ? S7 C2 C16 N17 19(11) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 62.53 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.367 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.052 #===END data_6b _database_code_CSD 203328 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H18 O4 S2' _chemical_formula_weight 350.43 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 9.117(1) _cell_length_b 14.592(2) _cell_length_c 25.690(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3417.7(8) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 32 _cell_measurement_theta_min 10.5 _cell_measurement_theta_max 12.1 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.362 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_absorpt_coefficient_mu 0.328 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 'Stoe-Siemens four-circle diffractometer' _diffrn_measurement_method '\w/\q scans with on-line profile fitting' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 5 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 1 _diffrn_reflns_number 3195 _diffrn_reflns_av_R_equivalents 0.0153 _diffrn_reflns_av_sigmaI/netI 0.0373 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 24.98 _reflns_number_total 3004 _reflns_number_gt 2229 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Stoe DIF4' _computing_cell_refinement 'Stoe DIF4' _computing_data_reduction 'local programs' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0394P)^2^+2.3769P] 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 0.00040(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3004 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0614 _refine_ls_R_factor_gt 0.0353 _refine_ls_wR_factor_ref 0.1018 _refine_ls_wR_factor_gt 0.0878 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 O1 O 0.21596(19) 0.54200(11) 0.06291(6) 0.0348(4) Uani 1 1 d . . . C2 C 0.3176(3) 0.50950(15) 0.10003(9) 0.0268(5) Uani 1 1 d . . . C3 C 0.2846(3) 0.45274(16) 0.05392(9) 0.0297(5) Uani 1 1 d . . . H3 H 0.3629 0.4525 0.0267 0.036 Uiso 1 1 calc R . . C4 C 0.1890(3) 0.36926(17) 0.05436(10) 0.0372(6) Uani 1 1 d . . . H4 H 0.1140 0.3757 0.0825 0.045 Uiso 1 1 calc R . . C5 C 0.2848(4) 0.28610(18) 0.06574(14) 0.0568(8) Uani 1 1 d . . . H5A H 0.2238 0.2308 0.0663 0.085 Uiso 1 1 calc R . . H5B H 0.3326 0.2939 0.0996 0.085 Uiso 1 1 calc R . . H5C H 0.3596 0.2801 0.0386 0.085 Uiso 1 1 calc R . . C6 C 0.1107(4) 0.3607(2) 0.00179(13) 0.0607(9) Uani 1 1 d . . . H6A H 0.0477 0.3063 0.0020 0.091 Uiso 1 1 calc R . . H6B H 0.1837 0.3549 -0.0260 0.091 Uiso 1 1 calc R . . H6C H 0.0507 0.4153 -0.0043 0.091 Uiso 1 1 calc R . . S7 S 0.49203(7) 0.57110(4) 0.09947(2) 0.02866(17) Uani 1 1 d . . . O8 O 0.4907(2) 0.64060(11) 0.13899(7) 0.0376(4) Uani 1 1 d . . . O9 O 0.5120(2) 0.59788(12) 0.04601(6) 0.0363(4) Uani 1 1 d . . . C10 C 0.6247(3) 0.48739(16) 0.11518(9) 0.0296(5) Uani 1 1 d . . . C11 C 0.6855(3) 0.48717(18) 0.16487(10) 0.0342(6) Uani 1 1 d . . . H11 H 0.6537 0.5299 0.1904 0.041 Uiso 1 1 calc R . . C12 C 0.7935(3) 0.42326(18) 0.17641(11) 0.0388(6) Uani 1 1 d . . . H12 H 0.8374 0.4229 0.2099 0.047 Uiso 1 1 calc R . . C13 C 0.8373(3) 0.36046(18) 0.13957(10) 0.0391(6) Uani 1 1 d . . . H13 H 0.9103 0.3165 0.1480 0.047 Uiso 1 1 calc R . . C14 C 0.7757(3) 0.36093(18) 0.09033(11) 0.0392(6) Uani 1 1 d . . . H14 H 0.8065 0.3171 0.0653 0.047 Uiso 1 1 calc R . . C15 C 0.6701(3) 0.42465(17) 0.07740(9) 0.0333(6) Uani 1 1 d . . . H15 H 0.6289 0.4258 0.0434 0.040 Uiso 1 1 calc R . . S16 S 0.23828(7) 0.48035(4) 0.16340(2) 0.03134(18) Uani 1 1 d . . . O17 O 0.3630(2) 0.46738(13) 0.19960(7) 0.0421(5) Uani 1 1 d . . . C18 C 0.1560(3) 0.58916(16) 0.17711(9) 0.0317(6) Uani 1 1 d . . . C19 C 0.0219(3) 0.60905(18) 0.15477(11) 0.0386(6) Uani 1 1 d . . . H19 H -0.0229 0.5673 0.1312 0.046 Uiso 1 1 calc R . . C20 C -0.0457(3) 0.69095(19) 0.16733(13) 0.0472(7) Uani 1 1 d . . . H20 H -0.1378 0.7059 0.1522 0.057 Uiso 1 1 calc R . . C21 C 0.0195(3) 0.7511(2) 0.20168(13) 0.0532(8) Uani 1 1 d . . . H21 H -0.0273 0.8073 0.2100 0.064 Uiso 1 1 calc R . . C22 C 0.1530(4) 0.7294(2) 0.22394(12) 0.0534(8) Uani 1 1 d . . . H22 H 0.1977 0.7712 0.2474 0.064 Uiso 1 1 calc R . . C23 C 0.2225(3) 0.64735(18) 0.21238(10) 0.0400(6) Uani 1 1 d . . . H23 H 0.3131 0.6316 0.2282 0.048 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 O1 0.0384(10) 0.0318(9) 0.0342(9) -0.0013(7) -0.0050(8) 0.0085(8) C2 0.0302(12) 0.0229(12) 0.0273(12) 0.0000(9) 0.0021(10) 0.0019(10) C3 0.0278(13) 0.0312(13) 0.0302(12) -0.0030(10) -0.0002(10) 0.0038(11) C4 0.0316(13) 0.0375(14) 0.0427(15) -0.0090(12) 0.0040(12) -0.0079(12) C5 0.062(2) 0.0301(15) 0.078(2) -0.0003(15) 0.0034(18) -0.0080(14) C6 0.0499(18) 0.073(2) 0.060(2) -0.0211(18) -0.0107(16) -0.0142(17) S7 0.0339(3) 0.0230(3) 0.0291(3) -0.0007(2) 0.0029(3) -0.0030(3) O8 0.0464(11) 0.0272(9) 0.0392(10) -0.0074(8) 0.0028(9) -0.0035(8) O9 0.0427(10) 0.0318(9) 0.0345(9) 0.0043(7) 0.0064(8) -0.0010(8) C10 0.0264(12) 0.0299(12) 0.0325(13) 0.0009(10) 0.0010(10) -0.0050(10) C11 0.0369(14) 0.0349(14) 0.0310(13) -0.0024(11) 0.0016(12) -0.0072(12) C12 0.0341(14) 0.0426(15) 0.0396(14) 0.0080(12) -0.0041(11) -0.0085(12) C13 0.0332(14) 0.0359(14) 0.0483(16) 0.0110(12) 0.0010(13) 0.0003(12) C14 0.0390(15) 0.0341(14) 0.0445(15) -0.0019(12) 0.0084(13) 0.0027(12) C15 0.0373(14) 0.0339(14) 0.0287(12) -0.0014(10) 0.0022(11) -0.0028(12) S16 0.0374(3) 0.0245(3) 0.0322(3) 0.0012(3) 0.0079(3) 0.0011(3) O17 0.0509(12) 0.0417(11) 0.0337(10) 0.0061(8) 0.0021(9) 0.0100(9) C18 0.0325(13) 0.0276(12) 0.0349(13) 0.0003(10) 0.0102(11) 0.0023(11) C19 0.0336(14) 0.0349(14) 0.0474(16) 0.0008(12) 0.0095(12) -0.0016(12) C20 0.0358(15) 0.0410(16) 0.0647(19) 0.0075(14) 0.0100(14) 0.0093(13) C21 0.0519(18) 0.0309(14) 0.077(2) -0.0012(15) 0.0240(17) 0.0101(14) C22 0.060(2) 0.0388(16) 0.062(2) -0.0192(14) 0.0115(16) 0.0001(15) C23 0.0413(16) 0.0402(15) 0.0384(14) -0.0091(12) 0.0040(12) 0.0042(12) _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 O1 C2 1.412(3) . ? O1 C3 1.464(3) . ? C2 C3 1.476(3) . ? C2 S7 1.827(2) . ? C2 S16 1.832(2) . ? C3 C4 1.498(3) . ? C4 C5 1.523(4) . ? C4 C6 1.533(4) . ? S7 O8 1.4350(17) . ? S7 O9 1.4395(18) . ? S7 C10 1.766(2) . ? C10 C11 1.392(3) . ? C10 C15 1.397(3) . ? C11 C12 1.388(4) . ? C12 C13 1.377(4) . ? C13 C14 1.384(4) . ? C14 C15 1.379(4) . ? S16 O17 1.481(2) . ? S16 C18 1.791(2) . ? C18 C19 1.381(4) . ? C18 C23 1.382(4) . ? C19 C20 1.383(4) . ? C20 C21 1.379(4) . ? C21 C22 1.381(4) . ? C22 C23 1.387(4) . ? 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 O1 C3 61.76(14) . . ? O1 C2 C3 60.85(15) . . ? O1 C2 S7 113.63(16) . . ? O1 C2 S16 114.79(17) . . ? C3 C2 S7 116.55(17) . . ? C3 C2 S16 120.17(17) . . ? S7 C2 S16 117.70(13) . . ? O1 C3 C2 57.40(14) . . ? O1 C3 C4 118.3(2) . . ? C2 C3 C4 124.7(2) . . ? C3 C4 C5 108.4(2) . . ? C3 C4 C6 109.3(2) . . ? C5 C4 C6 111.8(2) . . ? C2 S7 O8 109.56(11) . . ? C2 S7 O9 104.55(11) . . ? C2 S7 C10 104.73(11) . . ? O8 S7 O9 118.96(11) . . ? O8 S7 C10 109.46(11) . . ? O9 S7 C10 108.61(11) . . ? S7 C10 C11 118.95(19) . . ? S7 C10 C15 119.83(19) . . ? C11 C10 C15 121.2(2) . . ? C10 C11 C12 118.7(2) . . ? C11 C12 C13 120.4(3) . . ? C12 C13 C14 120.5(3) . . ? C13 C14 C15 120.4(3) . . ? C10 C15 C14 118.8(2) . . ? C2 S16 O17 106.54(11) . . ? C2 S16 C18 97.72(11) . . ? O17 S16 C18 108.15(11) . . ? S16 C18 C19 118.4(2) . . ? S16 C18 C23 119.3(2) . . ? C19 C18 C23 122.1(2) . . ? C18 C19 C20 118.6(3) . . ? C19 C20 C21 120.4(3) . . ? C20 C21 C22 120.0(3) . . ? C21 C22 C23 120.8(3) . . ? C18 C23 C22 118.1(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 C3 O1 C2 S7 108.34(18) . . . . ? C3 O1 C2 S16 -112.10(19) . . . . ? C2 O1 C3 C4 115.0(3) . . . . ? O1 C2 C3 C4 -104.0(2) . . . . ? S7 C2 C3 O1 -103.56(18) . . . . ? S7 C2 C3 C4 152.5(2) . . . . ? S16 C2 C3 O1 103.4(2) . . . . ? S16 C2 C3 C4 -0.6(3) . . . . ? O1 C3 C4 C5 -157.9(2) . . . . ? O1 C3 C4 C6 80.0(3) . . . . ? C2 C3 C4 C5 -89.8(3) . . . . ? C2 C3 C4 C6 148.2(2) . . . . ? O1 C2 S7 O8 96.69(17) . . . . ? O1 C2 S7 O9 -31.84(18) . . . . ? O1 C2 S7 C10 -145.99(16) . . . . ? C3 C2 S7 O8 164.62(17) . . . . ? C3 C2 S7 O9 36.1(2) . . . . ? C3 C2 S7 C10 -78.06(19) . . . . ? S16 C2 S7 O8 -41.61(16) . . . . ? S16 C2 S7 O9 -170.15(13) . . . . ? S16 C2 S7 C10 75.70(15) . . . . ? C2 S7 C10 C11 -104.7(2) . . . . ? C2 S7 C10 C15 77.2(2) . . . . ? O8 S7 C10 C11 12.6(2) . . . . ? O8 S7 C10 C15 -165.41(19) . . . . ? O9 S7 C10 C11 144.00(19) . . . . ? O9 S7 C10 C15 -34.0(2) . . . . ? S7 C10 C11 C12 -177.74(19) . . . . ? C15 C10 C11 C12 0.3(4) . . . . ? C10 C11 C12 C13 -1.1(4) . . . . ? C11 C12 C13 C14 0.9(4) . . . . ? C12 C13 C14 C15 0.3(4) . . . . ? C13 C14 C15 C10 -1.1(4) . . . . ? S7 C10 C15 C14 178.87(19) . . . . ? C11 C10 C15 C14 0.9(4) . . . . ? O1 C2 S16 O17 -168.12(16) . . . . ? O1 C2 S16 C18 -56.51(18) . . . . ? C3 C2 S16 O17 122.50(19) . . . . ? C3 C2 S16 C18 -125.9(2) . . . . ? S7 C2 S16 O17 -30.28(16) . . . . ? S7 C2 S16 C18 81.33(15) . . . . ? C2 S16 C18 C19 81.2(2) . . . . ? C2 S16 C18 C23 -103.5(2) . . . . ? O17 S16 C18 C19 -168.47(19) . . . . ? O17 S16 C18 C23 6.8(2) . . . . ? S16 C18 C19 C20 176.7(2) . . . . ? C23 C18 C19 C20 1.5(4) . . . . ? C18 C19 C20 C21 -0.3(4) . . . . ? C19 C20 C21 C22 -0.3(5) . . . . ? C20 C21 C22 C23 -0.3(5) . . . . ? S16 C18 C23 C22 -177.2(2) . . . . ? C19 C18 C23 C22 -2.1(4) . . . . ? C21 C22 C23 C18 1.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.430 _refine_diff_density_min -0.286 _refine_diff_density_rms 0.052 #===END data_7 _database_code_CSD 203329 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H18 O5 S2' _chemical_formula_weight 366.43 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 9.399(1) _cell_length_b 14.683(1) _cell_length_c 25.747(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3553.2(6) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 32 _cell_measurement_theta_min 10.0 _cell_measurement_theta_max 12.5 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.370 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1536 _exptl_absorpt_coefficient_mu 0.323 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Stoe-Siemens four-circle diffractometer' _diffrn_measurement_method '\w/\q scans with on-line profile fitting' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 5 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 5 _diffrn_reflns_number 3725 _diffrn_reflns_av_R_equivalents 0.0513 _diffrn_reflns_av_sigmaI/netI 0.1045 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 24.98 _reflns_number_total 3126 _reflns_number_gt 1411 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Stoe DIF4' _computing_cell_refinement 'Stoe DIF4' _computing_data_reduction 'local programs' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0539P)^2^+6.0765P] 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 3126 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1736 _refine_ls_R_factor_gt 0.0620 _refine_ls_wR_factor_ref 0.1974 _refine_ls_wR_factor_gt 0.1461 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 O1 O 0.7820(5) 0.5435(3) 0.43375(17) 0.0700(13) Uani 1 1 d . . . C2 C 0.6805(7) 0.5119(4) 0.3977(2) 0.0523(15) Uani 1 1 d . . . C3 C 0.7171(7) 0.4543(4) 0.4436(3) 0.0641(18) Uani 1 1 d . . . H3 H 0.6441 0.4563 0.4708 0.077 Uiso 1 1 calc R . . C4 C 0.8081(8) 0.3730(5) 0.4471(3) 0.078(2) Uani 1 1 d . . . H4 H 0.8813 0.3765 0.4201 0.094 Uiso 1 1 calc R . . C5 C 0.7181(9) 0.2882(5) 0.4380(3) 0.092(3) Uani 1 1 d . . . H5A H 0.6734 0.2920 0.4046 0.138 Uiso 1 1 calc R . . H5B H 0.6465 0.2839 0.4645 0.138 Uiso 1 1 calc R . . H5C H 0.7778 0.2352 0.4393 0.138 Uiso 1 1 calc R . . C6 C 0.8801(9) 0.3701(6) 0.4997(3) 0.107(3) Uani 1 1 d . . . H6A H 0.9374 0.4237 0.5041 0.160 Uiso 1 1 calc R . . H6B H 0.9393 0.3170 0.5019 0.160 Uiso 1 1 calc R . . H6C H 0.8091 0.3679 0.5265 0.160 Uiso 1 1 calc R . . S7 S 0.51121(18) 0.57052(10) 0.40182(6) 0.0548(4) Uani 1 1 d . . . O8 O 0.5080(5) 0.6421(2) 0.36455(16) 0.0645(12) Uani 1 1 d . . . O9 O 0.4963(5) 0.5942(3) 0.45618(15) 0.0698(13) Uani 1 1 d . . . C10 C 0.3816(6) 0.4883(4) 0.3868(2) 0.0504(15) Uani 1 1 d . . . C11 C 0.3162(7) 0.4896(4) 0.3381(2) 0.0575(16) Uani 1 1 d . . . H11 H 0.3431 0.5318 0.3130 0.069 Uiso 1 1 calc R . . C12 C 0.2112(6) 0.4271(5) 0.3282(3) 0.0628(17) Uani 1 1 d . . . H12 H 0.1651 0.4287 0.2962 0.075 Uiso 1 1 calc R . . C13 C 0.1723(7) 0.3631(5) 0.3634(3) 0.0664(19) Uani 1 1 d . . . H13 H 0.1015 0.3211 0.3555 0.080 Uiso 1 1 calc R . . C14 C 0.2398(8) 0.3611(4) 0.4117(3) 0.0675(18) Uani 1 1 d . . . H14 H 0.2137 0.3177 0.4362 0.081 Uiso 1 1 calc R . . C15 C 0.3445(7) 0.4231(4) 0.4231(2) 0.0625(17) Uani 1 1 d . . . H15 H 0.3903 0.4212 0.4551 0.075 Uiso 1 1 calc R . . S16 S 0.74953(19) 0.49608(10) 0.33184(6) 0.0541(4) Uani 1 1 d . . . O17 O 0.8551(5) 0.4262(3) 0.33329(19) 0.0729(13) Uani 1 1 d . . . O18 O 0.6275(4) 0.4861(3) 0.29909(16) 0.0611(11) Uani 1 1 d . . . C19 C 0.8346(7) 0.6002(4) 0.3194(2) 0.0538(16) Uani 1 1 d . . . C20 C 0.9711(7) 0.6148(4) 0.3378(3) 0.0650(18) Uani 1 1 d . . . H20 H 1.0170 0.5703 0.3573 0.078 Uiso 1 1 calc R . . C21 C 1.0381(8) 0.6956(5) 0.3269(3) 0.081(2) Uani 1 1 d . . . H21 H 1.1298 0.7063 0.3391 0.098 Uiso 1 1 calc R . . C22 C 0.9694(10) 0.7602(5) 0.2982(3) 0.088(3) Uani 1 1 d . . . H22 H 1.0148 0.8152 0.2915 0.105 Uiso 1 1 calc R . . C23 C 0.8360(10) 0.7462(5) 0.2792(3) 0.086(2) Uani 1 1 d . . . H23 H 0.7923 0.7911 0.2593 0.103 Uiso 1 1 calc R . . C24 C 0.7654(8) 0.6656(4) 0.2892(2) 0.0643(18) Uani 1 1 d . . . H24 H 0.6746 0.6551 0.2762 0.077 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 O1 0.075(3) 0.070(3) 0.065(3) 0.011(2) -0.021(3) -0.022(2) C2 0.069(4) 0.047(3) 0.041(3) 0.007(3) -0.011(3) -0.011(3) C3 0.065(4) 0.067(4) 0.060(4) 0.016(3) -0.007(4) -0.006(4) C4 0.088(5) 0.073(5) 0.073(5) 0.019(4) -0.001(4) 0.021(4) C5 0.125(7) 0.058(4) 0.093(6) 0.002(4) 0.003(6) 0.018(5) C6 0.102(7) 0.116(7) 0.101(7) 0.042(5) -0.029(6) 0.009(6) S7 0.0688(10) 0.0507(8) 0.0450(8) 0.0011(7) 0.0043(8) -0.0016(8) O8 0.084(3) 0.046(2) 0.064(3) 0.009(2) 0.006(3) 0.007(2) O9 0.088(3) 0.074(3) 0.047(3) -0.012(2) 0.012(3) -0.005(3) C10 0.052(4) 0.053(3) 0.046(4) 0.004(3) 0.012(3) 0.007(3) C11 0.062(4) 0.072(4) 0.038(4) 0.009(3) 0.004(3) 0.011(4) C12 0.051(4) 0.077(5) 0.060(4) -0.011(4) -0.006(3) 0.011(4) C13 0.054(4) 0.069(4) 0.076(5) -0.011(4) 0.007(4) 0.003(4) C14 0.069(4) 0.062(4) 0.071(5) 0.008(3) 0.009(4) -0.003(4) C15 0.066(4) 0.066(4) 0.055(4) 0.011(3) -0.001(3) -0.001(4) S16 0.0545(8) 0.0450(7) 0.0628(9) -0.0035(8) 0.0034(10) 0.0006(8) O17 0.074(3) 0.055(2) 0.090(3) -0.005(2) 0.011(3) 0.009(2) O18 0.060(3) 0.069(3) 0.055(3) -0.010(2) -0.004(2) -0.008(2) C19 0.058(4) 0.053(4) 0.051(4) -0.006(3) 0.011(3) 0.000(3) C20 0.056(4) 0.054(4) 0.086(5) -0.004(3) 0.011(4) -0.002(3) C21 0.061(5) 0.077(5) 0.106(7) -0.017(5) 0.014(5) -0.015(4) C22 0.098(6) 0.059(4) 0.106(7) -0.010(5) 0.044(6) -0.018(5) C23 0.109(6) 0.065(5) 0.085(6) 0.021(4) 0.026(5) -0.001(5) C24 0.067(4) 0.066(4) 0.060(4) 0.010(3) 0.010(4) -0.004(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 O1 C2 1.410(7) . ? O1 C3 1.468(7) . ? C2 C3 1.494(8) . ? C2 S7 1.812(6) . ? C2 S16 1.829(6) . ? C3 C4 1.471(9) . ? C4 C5 1.523(10) . ? C4 C6 1.516(10) . ? S7 O8 1.424(4) . ? S7 O9 1.449(4) . ? S7 C10 1.758(6) . ? C10 C11 1.397(8) . ? C10 C15 1.382(8) . ? C11 C12 1.371(8) . ? C12 C13 1.356(9) . ? C13 C14 1.395(9) . ? C14 C15 1.372(9) . ? S16 O17 1.428(4) . ? S16 O18 1.431(4) . ? S16 C19 1.755(6) . ? C19 C20 1.385(8) . ? C19 C24 1.396(8) . ? C20 C21 1.372(9) . ? C21 C22 1.365(11) . ? C22 C23 1.362(10) . ? C23 C24 1.382(9) . ? 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 O1 C3 62.5(4) . . ? O1 C2 C3 60.6(4) . . ? O1 C2 S7 113.5(4) . . ? O1 C2 S16 114.4(4) . . ? C3 C2 S7 115.1(5) . . ? C3 C2 S16 125.4(5) . . ? S7 C2 S16 115.2(3) . . ? O1 C3 C2 56.8(3) . . ? O1 C3 C4 119.5(5) . . ? C2 C3 C4 129.9(7) . . ? C3 C4 C5 109.3(6) . . ? C3 C4 C6 109.7(7) . . ? C5 C4 C6 111.2(6) . . ? C2 S7 O8 109.2(3) . . ? C2 S7 O9 104.8(3) . . ? C2 S7 C10 105.6(3) . . ? O8 S7 O9 118.2(3) . . ? O8 S7 C10 110.1(3) . . ? O9 S7 C10 108.1(3) . . ? S7 C10 C11 119.5(5) . . ? S7 C10 C15 120.1(5) . . ? C11 C10 C15 120.3(6) . . ? C10 C11 C12 118.3(6) . . ? C11 C12 C13 122.2(7) . . ? C12 C13 C14 119.2(7) . . ? C13 C14 C15 120.2(6) . . ? C10 C15 C14 119.7(6) . . ? C2 S16 O17 108.3(3) . . ? C2 S16 O18 105.9(3) . . ? C2 S16 C19 102.7(3) . . ? O17 S16 O18 119.9(3) . . ? O17 S16 C19 108.3(3) . . ? O18 S16 C19 110.3(3) . . ? S16 C19 C20 119.7(5) . . ? S16 C19 C24 119.2(5) . . ? C20 C19 C24 121.0(6) . . ? C19 C20 C21 119.3(7) . . ? C20 C21 C22 119.7(7) . . ? C21 C22 C23 121.7(7) . . ? C22 C23 C24 120.3(8) . . ? C19 C24 C23 118.0(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 O1 C2 S7 106.6(5) . . . . ? C3 O1 C2 S16 -118.4(5) . . . . ? C2 O1 C3 C4 120.7(8) . . . . ? O1 C2 C3 C4 -102.8(7) . . . . ? S7 C2 C3 O1 -104.0(4) . . . . ? S7 C2 C3 C4 153.2(6) . . . . ? S16 C2 C3 O1 100.4(6) . . . . ? S16 C2 C3 C4 -2.4(10) . . . . ? O1 C3 C4 C5 -159.9(6) . . . . ? O1 C3 C4 C6 77.8(8) . . . . ? C2 C3 C4 C5 -90.1(8) . . . . ? C2 C3 C4 C6 147.6(7) . . . . ? O1 C2 S7 O8 95.6(4) . . . . ? O1 C2 S7 O9 -32.0(4) . . . . ? O1 C2 S7 C10 -146.0(4) . . . . ? C3 C2 S7 O8 162.8(4) . . . . ? C3 C2 S7 O9 35.3(5) . . . . ? C3 C2 S7 C10 -78.7(5) . . . . ? S16 C2 S7 O8 -39.0(4) . . . . ? S16 C2 S7 O9 -166.6(3) . . . . ? S16 C2 S7 C10 79.4(3) . . . . ? C2 S7 C10 C11 -104.3(5) . . . . ? C2 S7 C10 C15 75.9(5) . . . . ? O8 S7 C10 C11 13.5(5) . . . . ? O8 S7 C10 C15 -166.2(5) . . . . ? O9 S7 C10 C11 143.9(5) . . . . ? O9 S7 C10 C15 -35.8(6) . . . . ? S7 C10 C11 C12 -177.3(4) . . . . ? C15 C10 C11 C12 2.5(9) . . . . ? C10 C11 C12 C13 -1.9(9) . . . . ? C11 C12 C13 C14 0.8(10) . . . . ? C12 C13 C14 C15 -0.2(10) . . . . ? C13 C14 C15 C10 0.8(10) . . . . ? S7 C10 C15 C14 177.8(5) . . . . ? C11 C10 C15 C14 -2.0(9) . . . . ? O1 C2 S16 O17 63.9(4) . . . . ? O1 C2 S16 O18 -166.2(4) . . . . ? O1 C2 S16 C19 -50.5(5) . . . . ? C3 C2 S16 O17 -6.3(6) . . . . ? C3 C2 S16 O18 123.6(5) . . . . ? C3 C2 S16 C19 -120.7(5) . . . . ? S7 C2 S16 O17 -161.8(3) . . . . ? S7 C2 S16 O18 -32.0(4) . . . . ? S7 C2 S16 C19 83.7(4) . . . . ? C2 S16 C19 C20 82.1(5) . . . . ? C2 S16 C19 C24 -100.6(5) . . . . ? O17 S16 C19 C20 -32.3(6) . . . . ? O17 S16 C19 C24 145.0(5) . . . . ? O18 S16 C19 C20 -165.3(5) . . . . ? O18 S16 C19 C24 11.9(6) . . . . ? S16 C19 C20 C21 178.5(5) . . . . ? C24 C19 C20 C21 1.3(10) . . . . ? C19 C20 C21 C22 0.0(11) . . . . ? C20 C21 C22 C23 -1.1(12) . . . . ? C21 C22 C23 C24 1.0(12) . . . . ? C22 C23 C24 C19 0.3(11) . . . . ? S16 C19 C24 C23 -178.7(5) . . . . ? C20 C19 C24 C23 -1.5(9) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.552 _refine_diff_density_min -0.358 _refine_diff_density_rms 0.070 #===END