# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 207/284 data_woyd3 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C6 H11 N O2 S' _chemical_formula_weight 161.22 _chemical_melting_point ? _chemical_compound_source ? 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 5.452(12) _cell_length_b 7.353(6) _cell_length_c 19.264(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 772.3(19) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.387 _exptl_crystal_density_method ? _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.359 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 790 _diffrn_reflns_av_R_equivalents 0.0366 _diffrn_reflns_av_sigmaI/netI 0.0233 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 20.01 _reflns_number_total 723 _reflns_number_observed 673 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0844P)^2^+0.3426P] 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 ? _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 0.24(22) _refine_ls_number_reflns 722 _refine_ls_number_parameters 124 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0474 _refine_ls_R_factor_obs 0.0434 _refine_ls_wR_factor_all 0.1317 _refine_ls_wR_factor_obs 0.1103 _refine_ls_goodness_of_fit_all 1.079 _refine_ls_goodness_of_fit_obs 1.077 _refine_ls_restrained_S_all 1.234 _refine_ls_restrained_S_obs 1.077 _refine_ls_shift/esd_max -0.058 _refine_ls_shift/esd_mean 0.006 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group C1 C 0.1316(10) 0.4042(6) 0.3929(3) 0.0415(13) Uani 1 d . . H1 H -0.0497(103) 0.4001(70) 0.4001(24) 0.046 Uiso 1 d . . C2 C 0.2442(9) 0.5451(6) 0.4409(3) 0.0395(14) Uani 1 d . . C3 C 0.5340(14) 0.6724(9) 0.3512(3) 0.061(2) Uani 1 d . . H3A H 0.7038(134) 0.6878(89) 0.3551(28) 0.067 Uiso 1 d . . H3B H 0.4035(107) 0.7811(85) 0.3334(27) 0.067 Uiso 1 d . . C4 C 0.4907(14) 0.5249(10) 0.3045(4) 0.077(2) Uani 1 d . . H4B H 0.5619(111) 0.5553(85) 0.2533(36) 0.085 Uiso 1 d . . H4A H 0.5953(111) 0.3933(101) 0.3131(32) 0.085 Uiso 1 d . . C5 C 0.2068(10) 0.2107(7) 0.4156(3) 0.0423(14) Uani 1 d . . H5 H 0.1551(89) 0.2049(65) 0.4663(27) 0.047 Uiso 1 d . . C6 C 0.0738(13) 0.0676(9) 0.3743(4) 0.061(2) Uani 1 d . . H6A H -0.1103(121) 0.0824(79) 0.3879(26) 0.067 Uiso 1 d . . H6B H 0.1191(106) 0.0864(81) 0.3230(32) 0.067 Uiso 1 d . . H6C H 0.1140(110) -0.0341(91) 0.3924(30) 0.067 Uiso 1 d . . N1 N 0.4301(9) 0.6479(7) 0.4200(3) 0.0515(14) Uani 1 d . . H1N H 0.4758(110) 0.7183(85) 0.4497(30) 0.057 Uiso 1 d . . O1 O 0.4645(7) 0.1971(5) 0.4077(2) 0.0556(13) Uani 1 d . . H1O H 0.5291(124) 0.1537(99) 0.4364(32) 0.061 Uiso 1 d . . O2 O 0.1636(7) 0.5580(4) 0.5006(2) 0.0568(11) Uani 1 d . . S1 S 0.1729(3) 0.4510(2) 0.30136(7) 0.0621(6) Uani 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 C1 0.041(3) 0.037(3) 0.046(3) 0.003(3) -0.003(3) 0.009(3) C2 0.052(4) 0.017(3) 0.050(4) 0.007(3) 0.001(3) 0.014(3) C3 0.058(4) 0.061(4) 0.063(4) 0.003(4) 0.013(4) -0.007(4) C4 0.093(5) 0.071(5) 0.067(4) -0.008(4) 0.027(4) -0.003(4) C5 0.049(4) 0.030(3) 0.048(3) 0.000(3) 0.008(3) 0.001(3) C6 0.066(5) 0.041(3) 0.076(5) -0.010(4) 0.012(3) -0.009(3) N1 0.073(4) 0.034(3) 0.047(3) -0.003(2) 0.003(3) -0.006(3) O1 0.045(3) 0.042(3) 0.080(3) 0.013(2) -0.011(2) 0.007(2) O2 0.090(3) 0.035(2) 0.045(2) -0.002(2) 0.013(2) 0.000(2) S1 0.0680(11) 0.0754(11) 0.0430(9) 0.0087(8) -0.0087(8) 0.0010(10) _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 C1 C2 1.519(7) . ? C1 C5 1.544(7) . ? C1 S1 1.810(5) . ? C1 H1 1.00(5) . ? C2 O2 1.235(6) . ? C2 N1 1.327(7) . ? C3 C4 1.429(10) . ? C3 N1 1.451(8) . ? C3 H3A 0.94(7) . ? C3 H3B 1.12(6) . ? C4 S1 1.817(8) . ? C4 H4B 1.08(7) . ? C4 H4A 1.14(7) . ? C5 O1 1.417(7) . ? C5 C6 1.505(8) . ? C5 H5 1.02(5) . ? C6 H6A 1.04(6) . ? C6 H6B 1.03(6) . ? C6 H6C 0.85(6) . ? N1 H1N 0.81(6) . ? O1 H1O 0.73(7) . ? 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 C1 C5 110.4(4) . . ? C2 C1 S1 114.4(4) . . ? C5 C1 S1 114.7(4) . . ? C2 C1 H1 109.6(30) . . ? C5 C1 H1 101.3(30) . . ? S1 C1 H1 105.4(27) . . ? O2 C2 N1 120.8(5) . . ? O2 C2 C1 118.4(5) . . ? N1 C2 C1 120.8(5) . . ? C4 C3 N1 114.6(6) . . ? C4 C3 H3A 107.8(38) . . ? N1 C3 H3A 109.1(35) . . ? C4 C3 H3B 104.0(28) . . ? N1 C3 H3B 96.9(27) . . ? H3A C3 H3B 124.4(50) . . ? C3 C4 S1 113.9(5) . . ? C3 C4 H4B 111.0(34) . . ? S1 C4 H4B 111.9(33) . . ? C3 C4 H4A 118.1(34) . . ? S1 C4 H4A 103.2(31) . . ? H4B C4 H4A 97.4(47) . . ? O1 C5 C6 111.8(5) . . ? O1 C5 C1 107.3(5) . . ? C6 C5 C1 111.5(5) . . ? O1 C5 H5 112.0(27) . . ? C6 C5 H5 110.2(28) . . ? C1 C5 H5 103.7(27) . . ? C5 C6 H6A 105.0(32) . . ? C5 C6 H6B 107.3(33) . . ? H6A C6 H6B 117.2(44) . . ? C5 C6 H6C 105.9(43) . . ? H6A C6 H6C 103.7(54) . . ? H6B C6 H6C 116.6(55) . . ? C2 N1 C3 130.3(5) . . ? C2 N1 H1N 112.5(43) . . ? C3 N1 H1N 116.5(43) . . ? C5 O1 H1O 115.3(52) . . ? C1 S1 C4 98.2(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 C5 C1 C2 O2 -71.3(6) . . . . ? S1 C1 C2 O2 157.5(4) . . . . ? C5 C1 C2 N1 106.6(5) . . . . ? S1 C1 C2 N1 -24.7(6) . . . . ? N1 C3 C4 S1 48.8(8) . . . . ? C2 C1 C5 O1 -64.1(6) . . . . ? S1 C1 C5 O1 67.0(5) . . . . ? C2 C1 C5 C6 173.1(5) . . . . ? S1 C1 C5 C6 -55.8(6) . . . . ? O2 C2 N1 C3 -171.5(6) . . . . ? C1 C2 N1 C3 10.8(8) . . . . ? C4 C3 N1 C2 -23.7(10) . . . . ? C2 C1 S1 C4 42.1(4) . . . . ? C5 C1 S1 C4 -87.0(5) . . . . ? C3 C4 S1 C1 -55.9(6) . . . . ? _refine_diff_density_max 0.430 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.053