data_ncovdvm _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C3 H3 N O3 S' _chemical_formula_weight 133.12 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, -y, -z' _cell_length_a 8.2923(6) _cell_length_b 9.8389(7) _cell_length_c 11.8651(8) _cell_angle_alpha 67.290(2) _cell_angle_beta 71.5570(10) _cell_angle_gamma 83.4850(10) _cell_volume 847.08(10) _cell_formula_units_Z 6 _cell_measurement_temperature 203(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 1.566 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.486 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3475 _diffrn_reflns_av_R_equivalents 0.0067 _diffrn_reflns_av_sigmaI/netI 0.0120 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 28.31 _reflns_number_total 2841 _reflns_number_gt 2597 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0458P)^2^+0.2330P] 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 0.019(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2841 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0311 _refine_ls_R_factor_gt 0.0285 _refine_ls_wR_factor_ref 0.0801 _refine_ls_wR_factor_gt 0.0778 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.001 _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 0.41456(5) 0.06571(5) 0.73476(5) 0.04208(18) Uani 1 1 d . . . O1 O 0.55493(15) -0.17447(16) 0.82907(17) 0.0473(4) Uani 1 1 d . . . N1 N 0.45610(17) 0.18469(17) 0.58447(18) 0.0431(5) Uani 1 1 d . . . C1 C 0.6762(3) -0.2948(2) 0.8330(2) 0.0544(6) Uani 1 1 d . . . H1A H 0.6691 -0.3391 0.7745 0.082 Uiso 1 1 d R . . H1B H 0.6492 -0.3684 0.9193 0.082 Uiso 1 1 d R . . H1C H 0.7905 -0.2571 0.8081 0.082 Uiso 1 1 d R . . O2 O 0.67495(14) -0.05905(14) 0.61677(14) 0.0447(4) Uani 1 1 d . . . C2 C 0.57230(18) -0.0693(2) 0.7169(2) 0.0351(6) Uani 1 1 d . . . C3 C 0.5627(2) 0.18905(18) 0.4874(2) 0.0424(5) Uani 1 1 d . . . O3 O 0.65617(18) 0.20978(16) 0.38597(16) 0.0618(5) Uani 1 1 d . . . S11 S 0.31843(5) -0.15493(5) 1.10142(5) 0.04117(17) Uani 1 1 d . . . O11 O 0.08345(14) -0.05671(14) 1.24526(14) 0.0438(4) Uani 1 1 d . . . N11 N 0.43855(18) -0.3037(2) 1.1380(2) 0.0468(6) Uani 1 1 d . . . C11 C -0.0369(2) -0.0561(2) 1.3654(2) 0.0496(6) Uani 1 1 d . . . H11A H -0.1120 -0.1412 1.4037 0.074 Uiso 1 1 d R . . H11B H -0.1034 0.0332 1.3484 0.074 Uiso 1 1 d R . . H11C H 0.0247 -0.0596 1.4237 0.074 Uiso 1 1 d R . . O12 O 0.19101(14) -0.27142(17) 1.35236(17) 0.0465(4) Uani 1 1 d . . . C12 C 0.18569(17) -0.1720(2) 1.2563(2) 0.0335(6) Uani 1 1 d . . . C13 C 0.4444(2) -0.3953(3) 1.2372(3) 0.0469(8) Uani 1 1 d . . . O13 O 0.4656(2) -0.4948(2) 1.3253(2) 0.0766(6) Uani 1 1 d . . . S21 S 0.07359(5) 0.20769(5) 0.97218(5) 0.04185(18) Uani 1 1 d . . . O21 O 0.15976(16) 0.34746(15) 0.73393(16) 0.0495(4) Uani 1 1 d . . . N21 N -0.07548(19) 0.24345(17) 1.08967(18) 0.0479(5) Uani 1 1 d . . . C21 C 0.1642(3) 0.4680(2) 0.6145(2) 0.0544(6) Uani 1 1 d . . . H21A H 0.0613 0.4667 0.5926 0.082 Uiso 1 1 d R . . H21B H 0.2622 0.4577 0.5472 0.082 Uiso 1 1 d R . . H21C H 0.1726 0.5606 0.6235 0.082 Uiso 1 1 d R . . O22 O -0.04838(15) 0.45847(14) 0.84305(15) 0.0480(4) Uani 1 1 d . . . C22 C 0.05076(18) 0.36052(18) 0.8383(2) 0.0373(5) Uani 1 1 d . . . C23 C -0.1731(2) 0.3433(2) 1.0898(2) 0.0427(5) Uani 1 1 d . . . O23 O -0.27485(17) 0.43072(16) 1.10733(16) 0.0615(5) 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 S1 0.0440(2) 0.0445(3) 0.0358(5) -0.0173(3) -0.01096(19) 0.01402(16) O1 0.0579(7) 0.0419(8) 0.0334(13) -0.0094(9) -0.0138(6) 0.0172(5) N1 0.0473(7) 0.0412(8) 0.0347(15) -0.0104(10) -0.0137(7) 0.0148(6) C1 0.0662(11) 0.0425(10) 0.052(2) -0.0142(13) -0.0253(10) 0.0220(8) O2 0.0421(6) 0.0462(7) 0.0387(11) -0.0146(8) -0.0078(5) 0.0114(5) C2 0.0373(7) 0.0352(9) 0.0349(18) -0.0136(12) -0.0144(7) 0.0051(6) C3 0.0474(8) 0.0328(9) 0.0449(18) -0.0125(11) -0.0167(9) 0.0103(6) O3 0.0693(8) 0.0501(8) 0.0422(13) -0.0082(9) -0.0007(8) 0.0142(6) S11 0.0417(2) 0.0459(3) 0.0301(5) -0.0120(3) -0.00825(18) 0.00790(16) O11 0.0459(6) 0.0463(7) 0.0355(11) -0.0155(8) -0.0120(5) 0.0158(5) N11 0.0500(8) 0.0487(10) 0.0316(19) -0.0127(12) -0.0067(8) 0.0148(7) C11 0.0407(8) 0.0639(12) 0.0454(18) -0.0284(13) -0.0097(8) 0.0157(7) O12 0.0470(6) 0.0466(8) 0.0304(13) -0.0065(9) -0.0045(6) 0.0105(5) C12 0.0326(6) 0.0347(9) 0.0304(19) -0.0101(12) -0.0091(7) 0.0032(5) C13 0.0459(9) 0.0484(12) 0.041(3) -0.0206(17) -0.0061(9) 0.0141(8) O13 0.0891(11) 0.0671(11) 0.0477(18) -0.0123(12) -0.0117(9) 0.0423(9) S21 0.0446(2) 0.0360(2) 0.0369(5) -0.0092(3) -0.01115(19) 0.01251(15) O21 0.0590(7) 0.0426(7) 0.0298(12) -0.0062(9) -0.0042(6) 0.0131(5) N21 0.0574(8) 0.0414(8) 0.0312(14) -0.0058(10) -0.0093(7) 0.0133(6) C21 0.0664(11) 0.0493(12) 0.029(2) -0.0018(14) -0.0081(10) 0.0056(9) O22 0.0528(6) 0.0377(6) 0.0412(12) -0.0081(8) -0.0109(6) 0.0151(5) C22 0.0388(7) 0.0331(8) 0.0355(15) -0.0101(10) -0.0095(7) 0.0032(6) C23 0.0483(8) 0.0414(10) 0.0262(16) -0.0049(11) -0.0056(8) 0.0030(7) O23 0.0625(8) 0.0556(8) 0.0465(13) -0.0143(9) -0.0028(7) 0.0215(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 N1 1.661(2) . ? S1 C2 1.7802(15) . ? O1 C2 1.309(2) . ? O1 C1 1.460(2) . ? N1 C3 1.198(3) . ? O2 C2 1.197(2) . ? C3 O3 1.161(2) . ? S11 N11 1.6657(19) . ? S11 C12 1.773(2) . ? O11 C12 1.326(2) . ? O11 C11 1.460(2) . ? N11 C13 1.187(3) . ? O12 C12 1.191(2) . ? C13 O13 1.170(3) . ? S21 N21 1.6688(16) . ? S21 C22 1.761(2) . ? O21 C22 1.325(2) . ? O21 C21 1.448(3) . ? N21 C23 1.200(2) . ? O22 C22 1.2003(18) . ? C23 O23 1.165(2) . ? 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 N1 S1 C2 100.65(9) . . ? C2 O1 C1 116.01(15) . . ? C3 N1 S1 132.83(14) . . ? O2 C2 O1 128.32(15) . . ? O2 C2 S1 123.31(18) . . ? O1 C2 S1 108.37(12) . . ? O3 C3 N1 171.3(2) . . ? N11 S11 C12 100.31(10) . . ? C12 O11 C11 115.02(17) . . ? C13 N11 S11 132.31(14) . . ? O12 C12 O11 127.24(17) . . ? O12 C12 S11 124.36(12) . . ? O11 C12 S11 108.40(16) . . ? O13 C13 N11 171.00(18) . . ? N21 S21 C22 100.56(8) . . ? C22 O21 C21 116.01(14) . . ? C23 N21 S21 132.37(18) . . ? O22 C22 O21 126.7(2) . . ? O22 C22 S21 124.78(15) . . ? O21 C22 S21 108.48(11) . . ? O23 C23 N21 171.0(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 N1 C3 -2.4(2) . . . . ? C1 O1 C2 O2 0.1(2) . . . . ? C1 O1 C2 S1 -179.19(12) . . . . ? N1 S1 C2 O2 1.63(16) . . . . ? N1 S1 C2 O1 -179.08(11) . . . . ? S1 N1 C3 O3 180(100) . . . . ? C12 S11 N11 C13 -2.7(2) . . . . ? C11 O11 C12 O12 -1.3(2) . . . . ? C11 O11 C12 S11 178.88(11) . . . . ? N11 S11 C12 O12 -2.08(16) . . . . ? N11 S11 C12 O11 177.74(10) . . . . ? S11 N11 C13 O13 174.9(13) . . . . ? C22 S21 N21 C23 -0.8(2) . . . . ? C21 O21 C22 O22 3.2(3) . . . . ? C21 O21 C22 S21 -177.13(12) . . . . ? N21 S21 C22 O22 1.15(16) . . . . ? N21 S21 C22 O21 -178.55(12) . . . . ? S21 N21 C23 O23 -178.9(12) . . . . ? _diffrn_measured_fraction_theta_max 0.676 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.676 _refine_diff_density_max 0.235 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.060