# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Aggarwal, Varinder' 'Angelaud, Remy' 'Bihan, Dominique' 'Blackburn, Paul' 'Fieldhouse, Robin' 'Fonquerna, Silvia J.' 'Ford, Gair D.' 'Hynd, George' 'Jones, Elfyn' 'Jones, Ray V. H.' 'Jubault, Philippe' 'Palmer, Matthew J.' 'Ratcliffe, Paul D.' 'Spey, Sharon E.' _publ_contact_author_name 'Dr Varinder Aggarwal' _publ_contact_author_address ; School of Chemistry University of Bristol Cantock's Close Bristol BS8 1TS UK ; _publ_contact_author_email 'V.AGGARWAL@BRISTOL.AC.UK' _publ_section_title ; Synthesis and Evaluation of a Broad Range of Chiral Sulfides for Asymmetric Sulfur Ylide Epoxidation of Aldehydes ; data_ova3t _database_code_CSD 168552 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H26 O S' _chemical_formula_weight 254.42 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 'P2(1)2(1)2(1)' 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' _cell_length_a 7.5509(7) _cell_length_b 7.9475(8) _cell_length_c 23.423(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1405.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.202 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.214 _exptl_absorpt_correction_type semi-empirical _exptl_absorpt_correction_T_min 0.9706 _exptl_absorpt_correction_T_max 0.9789 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6196 _diffrn_reflns_av_R_equivalents 0.1054 _diffrn_reflns_av_sigmaI/netI 0.0725 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 23.33 _reflns_number_total 2032 _reflns_number_gt 1915 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0633P)^2^+0.2668P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(10) _refine_ls_number_reflns 2032 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0481 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1160 _refine_ls_wR_factor_gt 0.1138 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.61808(9) 0.67180(8) 0.22464(3) 0.0335(2) Uani 1 1 d . . . O1 O 0.4236(3) 0.6939(2) 0.23453(9) 0.0443(5) Uani 1 1 d . . . C1 C 0.6523(3) 0.5100(3) 0.17141(11) 0.0294(6) Uani 1 1 d . . . H1A H 0.7786 0.4884 0.1696 0.035 Uiso 1 1 calc R . . H1B H 0.5970 0.4081 0.1856 0.035 Uiso 1 1 calc R . . C2 C 0.5880(3) 0.5358(3) 0.11013(10) 0.0277(6) Uani 1 1 d . . . C3 C 0.6114(4) 0.7168(3) 0.08599(10) 0.0292(6) Uani 1 1 d . . . H3A H 0.7337 0.7275 0.0725 0.035 Uiso 1 1 calc R . . C4 C 0.5764(4) 0.8606(3) 0.12779(11) 0.0327(6) Uani 1 1 d . . . H4A H 0.4522 0.8591 0.1383 0.039 Uiso 1 1 calc R . . H4B H 0.5996 0.9665 0.1086 0.039 Uiso 1 1 calc R . . C5 C 0.6881(3) 0.8531(3) 0.18219(11) 0.0289(6) Uani 1 1 d . . . H5A H 0.6572 0.9532 0.2045 0.035 Uiso 1 1 calc R . . C6 C 0.6940(4) 0.4218(3) 0.06910(12) 0.0376(7) Uani 1 1 d . . . H6A H 0.7051 0.3089 0.0844 0.045 Uiso 1 1 calc R . . H6B H 0.8114 0.4672 0.0623 0.045 Uiso 1 1 calc R . . C7 C 0.5821(4) 0.4221(4) 0.01324(12) 0.0424(7) Uani 1 1 d . . . H7A H 0.6476 0.4708 -0.0183 0.051 Uiso 1 1 calc R . . H7B H 0.5450 0.3092 0.0030 0.051 Uiso 1 1 calc R . . C8 C 0.4230(4) 0.5322(3) 0.02972(11) 0.0339(6) Uani 1 1 d . . . H8A H 0.3185 0.5161 0.0055 0.041 Uiso 1 1 calc R . . C9 C 0.3930(3) 0.4881(3) 0.09346(10) 0.0300(6) Uani 1 1 d . . . C10 C 0.4885(4) 0.7139(3) 0.03266(12) 0.0349(6) Uani 1 1 d . . . H10A H 0.3902 0.7914 0.0373 0.042 Uiso 1 1 calc R . . H10B H 0.5536 0.7437 -0.0016 0.042 Uiso 1 1 calc R . . C11 C 0.8899(3) 0.8563(3) 0.17518(11) 0.0305(6) Uani 1 1 d . . . H11A H 0.9263 0.7536 0.1552 0.037 Uiso 1 1 calc R . . C12 C 0.9459(4) 1.0078(4) 0.13925(14) 0.0457(7) Uani 1 1 d . . . H12A H 1.0724 1.0083 0.1352 0.069 Uiso 1 1 calc R . . H12B H 0.9085 1.1095 0.1578 0.069 Uiso 1 1 calc R . . H12C H 0.8919 1.0006 0.1022 0.069 Uiso 1 1 calc R . . C13 C 0.9843(4) 0.8619(4) 0.23264(13) 0.0406(7) Uani 1 1 d . . . H13A H 1.1101 0.8639 0.2266 0.061 Uiso 1 1 calc R . . H13B H 0.9532 0.7641 0.2545 0.061 Uiso 1 1 calc R . . H13C H 0.9491 0.9613 0.2530 0.061 Uiso 1 1 calc R . . C14 C 0.2407(4) 0.5878(4) 0.12003(12) 0.0394(7) Uani 1 1 d . . . H14A H 0.1299 0.5449 0.1061 0.059 Uiso 1 1 calc R . . H14B H 0.2517 0.7043 0.1098 0.059 Uiso 1 1 calc R . . H14C H 0.2448 0.5768 0.1608 0.059 Uiso 1 1 calc R . . C15 C 0.3498(4) 0.3027(4) 0.10428(13) 0.0446(7) Uani 1 1 d . . . H15A H 0.2293 0.2808 0.0935 0.067 Uiso 1 1 calc R . . H15B H 0.3653 0.2778 0.1441 0.067 Uiso 1 1 calc R . . H15C H 0.4276 0.2332 0.0821 0.067 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 S1 0.0380(4) 0.0377(4) 0.0248(4) -0.0025(3) 0.0041(3) -0.0057(3) O1 0.0394(11) 0.0522(11) 0.0411(11) -0.0073(9) 0.0138(9) -0.0067(9) C1 0.0273(14) 0.0309(12) 0.0299(13) -0.0014(11) -0.0017(12) 0.0004(11) C2 0.0250(13) 0.0312(12) 0.0268(13) -0.0010(11) 0.0000(11) 0.0036(11) C3 0.0255(13) 0.0381(14) 0.0241(12) 0.0029(10) -0.0016(11) 0.0011(11) C4 0.0319(14) 0.0285(13) 0.0378(15) 0.0034(11) -0.0011(12) 0.0011(11) C5 0.0295(14) 0.0269(12) 0.0301(14) -0.0044(11) 0.0022(11) -0.0029(11) C6 0.0345(16) 0.0418(15) 0.0365(16) -0.0082(13) -0.0048(13) 0.0050(13) C7 0.0399(17) 0.0569(17) 0.0305(14) -0.0100(13) -0.0009(13) 0.0006(15) C8 0.0295(14) 0.0452(14) 0.0270(13) -0.0013(12) -0.0065(11) 0.0017(12) C9 0.0265(13) 0.0359(13) 0.0275(12) -0.0012(10) -0.0015(12) 0.0020(11) C10 0.0303(13) 0.0450(15) 0.0294(14) 0.0062(12) -0.0033(12) 0.0013(12) C11 0.0260(13) 0.0343(13) 0.0312(13) -0.0051(11) 0.0049(12) -0.0043(12) C12 0.0415(16) 0.0594(18) 0.0363(15) 0.0033(15) -0.0011(14) -0.0160(14) C13 0.0350(15) 0.0428(15) 0.0440(17) 0.0025(14) -0.0088(14) -0.0055(12) C14 0.0240(14) 0.0548(17) 0.0394(16) -0.0052(14) 0.0038(13) -0.0054(13) C15 0.0474(18) 0.0447(16) 0.0417(16) -0.0020(13) -0.0061(14) -0.0099(14) _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 S1 O1 1.497(2) . ? S1 C1 1.810(2) . ? S1 C5 1.829(2) . ? C1 C2 1.529(3) . ? C2 C6 1.544(4) . ? C2 C3 1.556(3) . ? C2 C9 1.569(4) . ? C3 C4 1.528(4) . ? C3 C10 1.557(4) . ? C4 C5 1.529(4) . ? C5 C11 1.533(4) . ? C6 C7 1.558(4) . ? C7 C8 1.536(4) . ? C8 C10 1.528(4) . ? C8 C9 1.550(4) . ? C9 C14 1.529(4) . ? C9 C15 1.530(4) . ? C11 C13 1.524(4) . ? C11 C12 1.528(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 O1 S1 C1 109.27(12) . . ? O1 S1 C5 106.00(12) . . ? C1 S1 C5 98.27(11) . . ? C2 C1 S1 120.41(17) . . ? C1 C2 C6 109.9(2) . . ? C1 C2 C3 115.4(2) . . ? C6 C2 C3 104.9(2) . . ? C1 C2 C9 120.0(2) . . ? C6 C2 C9 101.0(2) . . ? C3 C2 C9 103.9(2) . . ? C4 C3 C2 116.06(19) . . ? C4 C3 C10 115.0(2) . . ? C2 C3 C10 102.1(2) . . ? C3 C4 C5 114.2(2) . . ? C4 C5 C11 117.3(2) . . ? C4 C5 S1 108.92(17) . . ? C11 C5 S1 111.03(18) . . ? C2 C6 C7 103.9(2) . . ? C8 C7 C6 102.4(2) . . ? C10 C8 C7 107.3(2) . . ? C10 C8 C9 102.5(2) . . ? C7 C8 C9 103.1(2) . . ? C14 C9 C15 105.7(2) . . ? C14 C9 C8 112.6(2) . . ? C15 C9 C8 114.1(2) . . ? C14 C9 C2 118.6(2) . . ? C15 C9 C2 113.0(2) . . ? C8 C9 C2 92.78(19) . . ? C8 C10 C3 104.1(2) . . ? C13 C11 C12 109.5(2) . . ? C13 C11 C5 111.8(2) . . ? C12 C11 C5 110.3(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 S1 C1 C2 64.6(2) . . . . ? C5 S1 C1 C2 -45.6(2) . . . . ? S1 C1 C2 C6 157.12(19) . . . . ? S1 C1 C2 C3 38.8(3) . . . . ? S1 C1 C2 C9 -86.6(3) . . . . ? C1 C2 C3 C4 -38.6(3) . . . . ? C6 C2 C3 C4 -159.7(2) . . . . ? C9 C2 C3 C4 94.8(3) . . . . ? C1 C2 C3 C10 -164.4(2) . . . . ? C6 C2 C3 C10 74.5(2) . . . . ? C9 C2 C3 C10 -31.1(2) . . . . ? C2 C3 C4 C5 56.2(3) . . . . ? C10 C3 C4 C5 175.3(2) . . . . ? C3 C4 C5 C11 59.2(3) . . . . ? C3 C4 C5 S1 -68.0(2) . . . . ? O1 S1 C5 C4 -56.2(2) . . . . ? C1 S1 C5 C4 56.67(19) . . . . ? O1 S1 C5 C11 173.21(17) . . . . ? C1 S1 C5 C11 -73.92(19) . . . . ? C1 C2 C6 C7 164.4(2) . . . . ? C3 C2 C6 C7 -70.9(3) . . . . ? C9 C2 C6 C7 36.8(3) . . . . ? C2 C6 C7 C8 -1.5(3) . . . . ? C6 C7 C8 C10 72.8(3) . . . . ? C6 C7 C8 C9 -35.0(3) . . . . ? C10 C8 C9 C14 67.3(3) . . . . ? C7 C8 C9 C14 178.6(2) . . . . ? C10 C8 C9 C15 -172.2(2) . . . . ? C7 C8 C9 C15 -60.9(3) . . . . ? C10 C8 C9 C2 -55.4(2) . . . . ? C7 C8 C9 C2 55.9(2) . . . . ? C1 C2 C9 C14 65.7(3) . . . . ? C6 C2 C9 C14 -173.5(2) . . . . ? C3 C2 C9 C14 -65.0(3) . . . . ? C1 C2 C9 C15 -58.9(3) . . . . ? C6 C2 C9 C15 61.9(3) . . . . ? C3 C2 C9 C15 170.4(2) . . . . ? C1 C2 C9 C8 -176.6(2) . . . . ? C6 C2 C9 C8 -55.8(2) . . . . ? C3 C2 C9 C8 52.7(2) . . . . ? C7 C8 C10 C3 -69.2(3) . . . . ? C9 C8 C10 C3 39.0(3) . . . . ? C4 C3 C10 C8 -131.0(2) . . . . ? C2 C3 C10 C8 -4.5(3) . . . . ? C4 C5 C11 C13 175.6(2) . . . . ? S1 C5 C11 C13 -58.3(2) . . . . ? C4 C5 C11 C12 53.5(3) . . . . ? S1 C5 C11 C12 179.57(18) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 23.33 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.339 _refine_diff_density_min -0.350 _refine_diff_density_rms 0.054 data_ova28m _database_code_CSD 168553 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H14 O3 S' _chemical_formula_weight 190.25 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 'P2(1)2(1)2(1)' 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' _cell_length_a 5.2525(19) _cell_length_b 10.029(4) _cell_length_c 17.826(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 939.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.346 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.311 _exptl_absorpt_correction_type semi-empirical _exptl_absorpt_correction_T_min 0.8805 _exptl_absorpt_correction_T_max 0.9577 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5702 _diffrn_reflns_av_R_equivalents 0.0930 _diffrn_reflns_av_sigmaI/netI 0.0720 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 28.26 _reflns_number_total 2148 _reflns_number_gt 1888 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1064P)^2^+0.0000P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.15(14) _refine_ls_number_reflns 2148 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0709 _refine_ls_R_factor_gt 0.0638 _refine_ls_wR_factor_ref 0.1577 _refine_ls_wR_factor_gt 0.1515 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 S1 S 0.91602(16) 0.48153(7) 0.19276(4) 0.0322(2) Uani 1 1 d . . . O1 O 0.4566(5) 0.4305(2) 0.08008(13) 0.0360(6) Uani 1 1 d . . . O2 O 0.7333(5) 0.7410(2) 0.02686(11) 0.0281(5) Uani 1 1 d . . . H2A H 0.8713 0.7512 0.0037 0.042 Uiso 1 1 calc R . . O3 O 0.7507(4) 0.4315(2) -0.01219(12) 0.0305(5) Uani 1 1 d . . . C1 C 0.8595(6) 0.5464(3) 0.09904(17) 0.0261(6) Uani 1 1 d . . . H1A H 1.0233 0.5396 0.0707 0.031 Uiso 1 1 calc R . . C2 C 0.6310(6) 0.5388(3) 0.24106(17) 0.0295(7) Uani 1 1 d . . . H2B H 0.4815 0.4900 0.2213 0.035 Uiso 1 1 calc R . . H2C H 0.6464 0.5182 0.2952 0.035 Uiso 1 1 calc R . . C3 C 0.5880(8) 0.6886(3) 0.23132(17) 0.0331(7) Uani 1 1 d . . . H3A H 0.7366 0.7377 0.2514 0.040 Uiso 1 1 calc R . . H3B H 0.4361 0.7159 0.2604 0.040 Uiso 1 1 calc R . . C4 C 0.5497(6) 0.7251(3) 0.14877(16) 0.0265(6) Uani 1 1 d . . . H4A H 0.4027 0.6747 0.1287 0.032 Uiso 1 1 calc R . . H4B H 0.5095 0.8213 0.1450 0.032 Uiso 1 1 calc R . . C5 C 0.7842(5) 0.6949(3) 0.10128(16) 0.0230(6) Uani 1 1 d . . . H5A H 0.9309 0.7469 0.1218 0.028 Uiso 1 1 calc R . . C6 C 0.6631(6) 0.4638(3) 0.05707(16) 0.0258(6) Uani 1 1 d . . . C7 C 0.5866(7) 0.3467(3) -0.05785(17) 0.0323(7) Uani 1 1 d . . . H7A H 0.5077 0.2779 -0.0256 0.039 Uiso 1 1 calc R . . H7B H 0.6909 0.3007 -0.0962 0.039 Uiso 1 1 calc R . . C8 C 0.3785(8) 0.4263(4) -0.09658(19) 0.0407(8) Uani 1 1 d . . . H8A H 0.2716 0.3660 -0.1262 0.061 Uiso 1 1 calc R . . H8B H 0.4560 0.4928 -0.1297 0.061 Uiso 1 1 calc R . . H8C H 0.2739 0.4713 -0.0588 0.061 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 S1 0.0297(4) 0.0308(4) 0.0361(4) 0.0078(3) -0.0059(3) 0.0016(3) O1 0.0322(14) 0.0360(11) 0.0397(12) -0.0095(9) 0.0035(10) -0.0062(10) O2 0.0248(11) 0.0318(10) 0.0276(10) 0.0081(8) 0.0006(9) 0.0005(8) O3 0.0304(12) 0.0282(10) 0.0330(11) -0.0061(8) 0.0012(9) 0.0005(9) C1 0.0255(16) 0.0228(12) 0.0299(13) 0.0024(10) -0.0003(11) -0.0013(10) C2 0.0319(18) 0.0297(13) 0.0268(13) 0.0045(11) -0.0033(12) -0.0024(11) C3 0.0444(19) 0.0271(13) 0.0278(14) -0.0010(11) 0.0043(14) -0.0024(14) C4 0.0265(16) 0.0214(11) 0.0316(14) 0.0016(10) 0.0033(13) 0.0016(11) C5 0.0205(15) 0.0210(12) 0.0274(13) 0.0021(10) -0.0005(11) -0.0010(10) C6 0.0281(16) 0.0205(12) 0.0287(14) -0.0010(10) 0.0007(11) 0.0029(10) C7 0.0388(18) 0.0260(13) 0.0322(14) -0.0066(11) -0.0018(14) 0.0020(13) C8 0.045(2) 0.0447(17) 0.0323(15) -0.0070(14) -0.0031(15) 0.0020(16) _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 S1 C1 1.817(3) . ? S1 C2 1.820(3) . ? O1 C6 1.206(4) . ? O2 C5 1.430(3) . ? O3 C6 1.357(4) . ? O3 C7 1.459(4) . ? C1 C6 1.520(4) . ? C1 C5 1.542(4) . ? C2 C3 1.528(4) . ? C3 C4 1.530(4) . ? C4 C5 1.525(4) . ? C7 C8 1.519(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 C1 S1 C2 100.81(14) . . ? C6 O3 C7 116.5(3) . . ? C6 C1 C5 111.4(2) . . ? C6 C1 S1 111.62(19) . . ? C5 C1 S1 111.3(2) . . ? C3 C2 S1 112.2(2) . . ? C2 C3 C4 111.4(2) . . ? C5 C4 C3 112.3(3) . . ? O2 C5 C4 107.5(2) . . ? O2 C5 C1 109.7(2) . . ? C4 C5 C1 114.4(2) . . ? O1 C6 O3 123.3(3) . . ? O1 C6 C1 126.4(3) . . ? O3 C6 C1 110.3(3) . . ? O3 C7 C8 111.9(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 S1 C1 C6 -75.9(2) . . . . ? C2 S1 C1 C5 49.3(2) . . . . ? C1 S1 C2 C3 -52.7(2) . . . . ? S1 C2 C3 C4 61.7(3) . . . . ? C2 C3 C4 C5 -63.1(4) . . . . ? C3 C4 C5 O2 -176.2(2) . . . . ? C3 C4 C5 C1 61.8(3) . . . . ? C6 C1 C5 O2 -52.8(3) . . . . ? S1 C1 C5 O2 -178.1(2) . . . . ? C6 C1 C5 C4 68.0(3) . . . . ? S1 C1 C5 C4 -57.3(3) . . . . ? C7 O3 C6 O1 -3.2(4) . . . . ? C7 O3 C6 C1 177.3(2) . . . . ? C5 C1 C6 O1 -75.4(4) . . . . ? S1 C1 C6 O1 49.8(4) . . . . ? C5 C1 C6 O3 104.2(3) . . . . ? S1 C1 C6 O3 -130.7(2) . . . . ? C6 O3 C7 C8 81.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 28.26 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 0.805 _refine_diff_density_min -0.421 _refine_diff_density_rms 0.114