Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 188 _journal_volume ? _journal_year ? _journal_page_first ? #======================================================================= # 1. SUBMISSION DETAILS #---------------------- _publ_contact_author_name 'Craig A. Hutton' _publ_contact_author_address ; School of Chemistry, The University of Sydney, NSW 2006, Australia ; _publ_contact_author_email c.hutton@chem.usyd.edu.au _publ_contact_author_fax +61 2 9351 3329 _publ_contact_author_phone +61 2 9351 2752 _publ_requested_journal 'J. Chem. Soc., Perkin Transactions 2' _publ_section_title ; Stereochemical and conformational consequences of the oxidation of 1,4-thiazane-3,5-dicarboxylates ; loop_ _publ_author_name _publ_author_address 'Craig A. Hutton' ; School of Chemistry, The University of Sydney, NSW 2006, Australia ; 'Rania Jaber' ; School of Chemistry, The University of Sydney, NSW 2006, Australia ; 'Michelle Otaegui' ; School of Chemistry, The University of Melbourne, VIC 3052, Australia ; 'Jennifer J. Turner' ; School of Chemistry, The University of Sydney, NSW 2006, Australia ; 'Peter Turner' ; School of Chemistry, The University of Sydney, NSW 2006, Australia ; 'Jonathan M. White' ; School of Chemistry, The University of Melbourne, VIC 3052, Australia ; 'George B. Bacskay' ; School of Chemistry, The University of Sydney, NSW 2006, Australia ; #======================================================================= # Data block for single structure (one for each study in the paper) #======================================================================= data_cah4 _database_code_CSD 180846 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H13 N O5 S' _chemical_formula_weight 235.25 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' 'N' 'N' 0.0061 0.0033 '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 21 21 21 ' _symmetry_Int_Tables_number 19 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 9.2817(15) _cell_length_b 10.5236(17) _cell_length_c 10.5688(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1032.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 959 _cell_measurement_theta_min 2.731 _cell_measurement_theta_max 27.984 _exptl_crystal_description blade _exptl_crystal_colour colourless _exptl_crystal_size_max 0.630 _exptl_crystal_size_mid 0.328 _exptl_crystal_size_min 0.113 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.514 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.315 _exptl_absorpt_correction_type Gaussian _exptl_absorpt_correction_T_min 0.840 _exptl_absorpt_correction_T_max 0.965 _exptl_absorpt_process_details ; Gaussian (Coppens et al., 1965) XPREP (Bruker, 1995) ; _exptl_special_details ; ? ; _diffrn_crystal_treatment ; attached with Exxon Paratone N, to a short length of fibre supported on a thin piece of copper wire inserted in a copper mounting pin. The crystal was quenched in a cold nitrogen gas stream from an Oxford Cryosystems Cryostream. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 203 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.07 _diffrn_reflns_number 10067 _diffrn_reflns_av_R_equivalents 0.0260 _diffrn_reflns_av_sigmaI/netI 0.0104 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.73 _diffrn_reflns_theta_max 28.26 _reflns_number_total 2450 _reflns_number_gt 2411 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker,1995)' _computing_cell_refinement 'SAINT (Bruker,1995)' _computing_data_reduction 'SAINT and XPREP (Bruker 1995)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; teXsan for Windows (MSC, 1997) xtal 3.6 (Hall,du Boulay, D.J. & Olthof-Hazekamp, R. 1999) ORTEPII (Johnson,C.K., 1976). WinGX (Farrugia, 1999) ; _computing_publication_material ? _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^)+(0.02P)^2^+0.2P] 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 0.00(5) _refine_ls_number_reflns 2450 _refine_ls_number_parameters 142 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0223 _refine_ls_R_factor_gt 0.0219 _refine_ls_wR_factor_ref 0.0546 _refine_ls_wR_factor_gt 0.0544 _refine_ls_goodness_of_fit_ref 1.293 _refine_ls_restrained_S_all 1.293 _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 0.39880(3) 0.65011(3) 0.59135(3) 0.01989(8) Uani 1 1 d . . . O1 O 0.24089(10) 0.64163(10) 0.62266(8) 0.0249(2) Uani 1 1 d . . . O2 O 0.17210(10) 0.38639(9) 0.45270(10) 0.0249(2) Uani 1 1 d . . . O3 O 0.08943(10) 0.54324(9) 0.32759(9) 0.02298(19) Uani 1 1 d . . . O4 O 0.27278(11) 0.97259(9) 0.35374(9) 0.0258(2) Uani 1 1 d . . . O5 O 0.31416(12) 0.87156(9) 0.16976(9) 0.0304(2) Uani 1 1 d . . . N1 N 0.36477(11) 0.64472(12) 0.29374(10) 0.0202(2) Uani 1 1 d . . . H1N H 0.3200(16) 0.6403(15) 0.2221(15) 0.021(4) Uiso 1 1 d . . . C1 C 0.43590(14) 0.52213(13) 0.48303(13) 0.0218(3) Uani 1 1 d . . . H1A H 0.5393 0.5249 0.4601 0.026 Uiso 1 1 calc R . . H1B H 0.4181 0.4405 0.5269 0.026 Uiso 1 1 calc R . . C2 C 0.34638(13) 0.52490(12) 0.36135(13) 0.0199(3) Uani 1 1 d . . . H2 H 0.3880 0.4578 0.3052 0.024 Uiso 1 1 calc R . . C3 C 0.31361(14) 0.75396(12) 0.36631(12) 0.0182(2) Uani 1 1 d . . . H3 H 0.2155 0.7339 0.4000 0.022 Uiso 1 1 calc R . . C4 C 0.41426(15) 0.77723(12) 0.47769(11) 0.0204(3) Uani 1 1 d . . . H4A H 0.3896 0.8590 0.5186 0.025 Uiso 1 1 calc R . . H4B H 0.5149 0.7827 0.4471 0.025 Uiso 1 1 calc R . . C5 C 0.18703(14) 0.48950(12) 0.37962(12) 0.0198(2) Uani 1 1 d . . . C6 C 0.02487(15) 0.34126(15) 0.46652(14) 0.0285(3) Uani 1 1 d . . . H6A H -0.0359 0.4103 0.4986 0.043 Uiso 1 1 calc R . . H6B H 0.0228 0.2700 0.5262 0.043 Uiso 1 1 calc R . . H6C H -0.0115 0.3131 0.3841 0.043 Uiso 1 1 calc R . . C7 C 0.30262(13) 0.87076(12) 0.28304(12) 0.0205(3) Uani 1 1 d . . . C8 C 0.25217(17) 1.09227(14) 0.28707(15) 0.0307(3) Uani 1 1 d . . . H8A H 0.3399 1.1135 0.2400 0.046 Uiso 1 1 calc R . . H8B H 0.2314 1.1598 0.3483 0.046 Uiso 1 1 calc R . . H8C H 0.1713 1.0841 0.2280 0.046 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 0.02173(14) 0.02141(14) 0.01654(13) 0.00073(12) -0.00157(11) -0.00039(12) O1 0.0233(4) 0.0274(5) 0.0242(4) 0.0037(4) 0.0049(4) 0.0024(4) O2 0.0248(5) 0.0207(5) 0.0291(5) 0.0023(4) -0.0017(4) -0.0028(4) O3 0.0209(4) 0.0220(4) 0.0260(5) -0.0011(4) -0.0019(4) 0.0006(4) O4 0.0318(5) 0.0208(5) 0.0247(5) 0.0020(4) -0.0005(4) 0.0031(4) O5 0.0413(6) 0.0301(5) 0.0199(5) 0.0047(4) 0.0020(4) -0.0020(5) N1 0.0216(5) 0.0232(5) 0.0158(5) -0.0018(4) 0.0012(4) 0.0000(4) C1 0.0194(6) 0.0217(6) 0.0243(6) -0.0023(5) -0.0016(5) 0.0040(5) C2 0.0184(6) 0.0199(6) 0.0213(6) -0.0027(5) 0.0009(5) 0.0017(5) C3 0.0178(5) 0.0202(6) 0.0167(6) -0.0004(5) 0.0008(5) -0.0017(5) C4 0.0244(6) 0.0193(6) 0.0176(6) 0.0005(4) -0.0016(5) -0.0039(5) C5 0.0216(6) 0.0176(5) 0.0202(6) -0.0051(5) 0.0007(5) -0.0001(5) C6 0.0264(7) 0.0254(7) 0.0338(7) 0.0039(6) 0.0007(6) -0.0049(6) C7 0.0155(5) 0.0234(6) 0.0226(6) 0.0023(5) -0.0004(4) -0.0029(5) C8 0.0316(7) 0.0227(7) 0.0377(8) 0.0072(6) -0.0043(6) 0.0030(6) _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 1.5052(10) . ? S1 C1 1.8008(14) . ? S1 C4 1.8036(13) . ? O2 C5 1.3390(16) . ? O2 C6 1.4541(16) . ? O3 C5 1.2012(16) . ? O4 C7 1.3354(16) . ? O4 C8 1.4558(16) . ? O5 C7 1.2020(16) . ? N1 C2 1.4593(17) . ? N1 C3 1.4613(16) . ? N1 H1N 0.865(16) . ? C1 C2 1.5314(19) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C5 1.5375(18) . ? C2 H2 1.0000 . ? C3 C7 1.5152(17) . ? C3 C4 1.5226(17) . ? C3 H3 1.0000 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? 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 106.36(6) . . ? O1 S1 C4 105.54(6) . . ? C1 S1 C4 96.67(6) . . ? C5 O2 C6 114.83(10) . . ? C7 O4 C8 116.79(11) . . ? C2 N1 C3 112.63(10) . . ? C2 N1 H1N 109.0(11) . . ? C3 N1 H1N 110.2(11) . . ? C2 C1 S1 114.58(9) . . ? C2 C1 H1A 108.6 . . ? S1 C1 H1A 108.6 . . ? C2 C1 H1B 108.6 . . ? S1 C1 H1B 108.6 . . ? H1A C1 H1B 107.6 . . ? N1 C2 C1 111.36(10) . . ? N1 C2 C5 112.54(10) . . ? C1 C2 C5 114.32(11) . . ? N1 C2 H2 106.0 . . ? C1 C2 H2 106.0 . . ? C5 C2 H2 106.0 . . ? N1 C3 C7 110.81(10) . . ? N1 C3 C4 109.45(11) . . ? C7 C3 C4 111.09(10) . . ? N1 C3 H3 108.5 . . ? C7 C3 H3 108.5 . . ? C4 C3 H3 108.5 . . ? C3 C4 S1 110.29(9) . . ? C3 C4 H4A 109.6 . . ? S1 C4 H4A 109.6 . . ? C3 C4 H4B 109.6 . . ? S1 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? O3 C5 O2 124.58(12) . . ? O3 C5 C2 123.64(12) . . ? O2 C5 C2 111.61(11) . . ? O2 C6 H6A 109.5 . . ? O2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? O2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O5 C7 O4 124.76(12) . . ? O5 C7 C3 125.32(12) . . ? O4 C7 C3 109.87(10) . . ? O4 C8 H8A 109.5 . . ? O4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? 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 58.21(11) . . . . ? C4 S1 C1 C2 -50.17(11) . . . . ? C3 N1 C2 C1 -63.05(13) . . . . ? C3 N1 C2 C5 66.83(13) . . . . ? S1 C1 C2 N1 56.78(13) . . . . ? S1 C1 C2 C5 -72.16(13) . . . . ? C2 N1 C3 C7 -167.03(10) . . . . ? C2 N1 C3 C4 70.12(13) . . . . ? N1 C3 C4 S1 -68.54(12) . . . . ? C7 C3 C4 S1 168.78(9) . . . . ? O1 S1 C4 C3 -54.10(10) . . . . ? C1 S1 C4 C3 54.97(10) . . . . ? C6 O2 C5 O3 -0.16(18) . . . . ? C6 O2 C5 C2 -175.55(11) . . . . ? N1 C2 C5 O3 10.87(18) . . . . ? C1 C2 C5 O3 139.22(13) . . . . ? N1 C2 C5 O2 -173.69(10) . . . . ? C1 C2 C5 O2 -45.35(15) . . . . ? C8 O4 C7 O5 0.42(19) . . . . ? C8 O4 C7 C3 -177.31(11) . . . . ? N1 C3 C7 O5 9.78(18) . . . . ? C4 C3 C7 O5 131.67(14) . . . . ? N1 C3 C7 O4 -172.51(10) . . . . ? C4 C3 C7 O4 -50.61(14) . . . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 28.26 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.229 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.041 #===END data_jmwch2 _database_code_CSD 180847 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point '96 C' _chemical_formula_moiety ? _chemical_formula_sum 'C8 H13 N O5 S' _chemical_formula_weight 235.25 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' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Cmc21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x, -y, z+1/2' '-x, y, z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z' _cell_length_a 19.486(3) _cell_length_b 8.3500(14) _cell_length_c 6.557(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1066.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10 _cell_measurement_theta_max 15 _exptl_crystal_description plate _exptl_crystal_colour white _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.465 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.305 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD-4 diffractometer' _diffrn_measurement_method \q2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 9600 _diffrn_standards_decay_% 2 _diffrn_reflns_number 922 _diffrn_reflns_av_R_equivalents 0.0184 _diffrn_reflns_av_sigmaI/netI 0.0315 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 2 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 24.97 _reflns_number_total 640 _reflns_number_gt 545 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD-4 Software 5.0 (Enraf-Nonius, 1989)' _computing_cell_refinement 'CAD-4 Software 5.0 (Enraf-Nonius, 1989)' _computing_data_reduction 'PROCESS_DATA (Gable et al., 1994)' _computing_structure_solution 'SHELXS-86 (Sheldrick)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3' _computing_publication_material 'WINGX' _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^)+(0.0370P)^2^+0.3559P] 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 SHELXL _refine_ls_extinction_coef 0.0004(7) _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 0.16(19) _refine_ls_number_reflns 640 _refine_ls_number_parameters 77 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0448 _refine_ls_R_factor_gt 0.0336 _refine_ls_wR_factor_ref 0.0772 _refine_ls_wR_factor_gt 0.0726 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.061 _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 0.5000 0.30273(13) 1.1950(2) 0.0324(4) Uani 1 2 d S . . O1 O 0.5000 0.1299(4) 1.2537(6) 0.0445(10) Uani 1 2 d S . . O2 O 0.37289(14) 0.2828(4) 0.5344(5) 0.0605(10) Uani 1 1 d . . . O3 O 0.32266(11) 0.1491(3) 0.7870(5) 0.0546(9) Uani 1 1 d . . . N4 N 0.5000 0.2526(5) 0.7187(8) 0.0311(11) Uani 1 2 d S . . C2 C 0.43099(16) 0.3257(4) 1.0142(6) 0.0350(10) Uani 1 1 d . . . H2A H 0.3876 0.3052 1.0820 0.042 Uiso 1 1 calc R . . H2B H 0.4303 0.4352 0.9648 0.042 Uiso 1 1 calc R . . C3 C 0.43861(16) 0.2113(4) 0.8331(6) 0.0291(9) Uani 1 1 d . . . H3 H 0.4431 0.1016 0.8844 0.035 Uiso 1 1 calc R . . C5 C 0.37571(15) 0.2215(4) 0.6971(10) 0.0365(8) Uani 1 1 d . . . C6 C 0.25935(17) 0.1471(5) 0.6725(9) 0.0619(15) Uani 1 1 d . . . H6A H 0.2246 0.0925 0.7497 0.093 Uiso 1 1 calc R . . H6B H 0.2665 0.0923 0.5455 0.093 Uiso 1 1 calc R . . H6C H 0.2449 0.2550 0.6461 0.093 Uiso 1 1 calc R . . H4 H 0.5000 0.196(6) 0.602(9) 0.040(17) Uiso 1 2 d S . . 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 0.0416(6) 0.0335(6) 0.0221(7) -0.0002(8) 0.000 0.000 O1 0.0573(19) 0.0403(18) 0.036(3) 0.013(2) 0.000 0.000 O2 0.0475(17) 0.091(2) 0.043(2) 0.024(2) -0.0122(15) -0.0169(16) O3 0.0320(12) 0.0856(19) 0.046(2) 0.011(2) -0.0043(15) -0.0116(13) N4 0.0306(19) 0.046(2) 0.017(3) 0.004(3) 0.000 0.000 C2 0.0350(19) 0.040(2) 0.030(2) -0.001(2) 0.005(2) 0.0059(15) C3 0.0269(16) 0.0321(16) 0.028(2) -0.0009(19) 0.0007(17) -0.0003(14) C5 0.0343(17) 0.0447(19) 0.031(2) 0.000(3) 0.000(3) 0.0005(14) C6 0.0312(18) 0.100(3) 0.054(4) 0.005(4) -0.007(2) -0.0086(18) _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 1.494(3) . ? S1 C2 1.803(4) 4_655 ? S1 C2 1.803(4) . ? O2 C5 1.184(6) . ? O3 C5 1.335(5) . ? O3 C6 1.444(4) . ? N4 C3 1.453(4) 4_655 ? N4 C3 1.453(4) . ? N4 H4 0.90(6) . ? C2 C3 1.531(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C5 1.518(6) . ? C3 H3 0.9800 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? 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 C2 105.81(16) . 4_655 ? O1 S1 C2 105.81(16) . . ? C2 S1 C2 96.5(2) 4_655 . ? C5 O3 C6 115.9(3) . . ? C3 N4 C3 110.8(4) 4_655 . ? C3 N4 H4 108.2(17) 4_655 . ? C3 N4 H4 108.2(17) . . ? C3 C2 S1 111.8(2) . . ? C3 C2 H2A 109.3 . . ? S1 C2 H2A 109.3 . . ? C3 C2 H2B 109.3 . . ? S1 C2 H2B 109.3 . . ? H2A C2 H2B 107.9 . . ? N4 C3 C5 110.4(3) . . ? N4 C3 C2 109.4(3) . . ? C5 C3 C2 110.0(3) . . ? N4 C3 H3 109.0 . . ? C5 C3 H3 109.0 . . ? C2 C3 H3 109.0 . . ? O2 C5 O3 123.9(4) . . ? O2 C5 C3 126.2(4) . . ? O3 C5 C3 109.9(4) . . ? O3 C6 H6A 109.5 . . ? O3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? O3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? 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 C2 C3 -55.7(3) . . . . ? C2 S1 C2 C3 52.8(3) 4_655 . . . ? C3 N4 C3 C5 -168.0(3) 4_655 . . . ? C3 N4 C3 C2 70.8(4) 4_655 . . . ? S1 C2 C3 N4 -64.8(4) . . . . ? S1 C2 C3 C5 173.8(3) . . . . ? C6 O3 C5 O2 0.7(6) . . . . ? C6 O3 C5 C3 -178.9(3) . . . . ? N4 C3 C5 O2 -13.8(6) . . . . ? C2 C3 C5 O2 107.0(5) . . . . ? N4 C3 C5 O3 165.8(3) . . . . ? C2 C3 C5 O3 -73.4(4) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.230 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.046