data_yj674 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H19 N O4 S' _chemical_formula_weight 357.41 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 Pbca _symmetry_space_group_name_Hall '-P 2ac 2ab ' 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 16.4246(5) _cell_length_b 11.9941(4) _cell_length_c 17.9328(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3532.73(19) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9574 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 27.71 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max .210 _exptl_crystal_size_mid .103 _exptl_crystal_size_min .047 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.344 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1504 _exptl_absorpt_coefficient_mu 0.207 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min .956 _exptl_absorpt_correction_T_max .973 _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 112643 _diffrn_reflns_av_R_equivalents 0.0736 _diffrn_reflns_av_sigmaI/netI 0.0215 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 27.71 _reflns_number_total 4137 _reflns_number_gt 3359 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'Siemens SMART & SAINT' _computing_data_reduction 'Siemens XPREP' _computing_structure_solution 'Siemens SHELXTL' _computing_structure_refinement 'Siemens SHELXTL' _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^)+(0.0730P)^2^+2.3671P] 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_number_reflns 4137 _refine_ls_number_parameters 242 _refine_ls_number_restraints 0 _refine_ls_R_factor_ref 0.0597 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1402 _refine_ls_wR_factor_gt 0.1201 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _refine_ls_shift/su_max 0.086 _refine_ls_shift/su_mean 0.004 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 0.08496(3) 0.01893(4) 0.32058(2) 0.03737(15) Uani 1 1 d . . . O1 O -0.19245(8) 0.11435(14) 0.13477(9) 0.0488(4) Uani 1 1 d . . . O2 O 0.14629(8) 0.12046(14) 0.01418(8) 0.0466(4) Uani 1 1 d . . . O3 O 0.05968(14) 0.13158(13) 0.31189(9) 0.0645(5) Uani 1 1 d . . . O4 O 0.16927(11) -0.00639(18) 0.32861(11) 0.0720(6) Uani 1 1 d . . . C1 C -0.10138(12) 0.19213(16) 0.01870(10) 0.0378(4) Uani 1 1 d . . . H1B H -0.1571 0.2059 0.0192 0.045 Uiso 1 1 calc R . . C2 C -0.05437(13) 0.23250(17) -0.03767(10) 0.0425(4) Uani 1 1 d . . . H2A H -0.0784 0.2757 -0.0747 0.051 Uiso 1 1 calc R . . C3 C 0.02936(12) 0.21056(17) -0.04127(10) 0.0403(4) Uani 1 1 d . . . H3B H 0.0602 0.2386 -0.0805 0.048 Uiso 1 1 calc R . . C4 C 0.06568(11) 0.14787(16) 0.01305(10) 0.0340(4) Uani 1 1 d . . . C5 C 0.01949(10) 0.10586(14) 0.07473(9) 0.0286(3) Uani 1 1 d . . . C6 C 0.05544(10) 0.04463(14) 0.13329(9) 0.0293(3) Uani 1 1 d . . . H6A H 0.1110 0.0295 0.1324 0.035 Uiso 1 1 calc R . . C7 C 0.00860(10) 0.00746(13) 0.19135(9) 0.0267(3) Uani 1 1 d . . . C8 C -0.07682(10) 0.02704(13) 0.19489(9) 0.0276(3) Uani 1 1 d . . . C9 C -0.11176(10) 0.08776(14) 0.13789(10) 0.0310(4) Uani 1 1 d . . . C10 C -0.06505(10) 0.12893(14) 0.07675(9) 0.0296(3) Uani 1 1 d . . . C11 C -0.12604(10) -0.01552(15) 0.25877(10) 0.0326(4) Uani 1 1 d . . . C12 C -0.13173(13) -0.12928(18) 0.27307(14) 0.0501(5) Uani 1 1 d . . . H12A H -0.1068 -0.1802 0.2413 0.060 Uiso 1 1 calc R . . C13 C -0.17484(16) -0.1665(3) 0.33497(18) 0.0736(9) Uani 1 1 d . . . H13A H -0.1783 -0.2425 0.3447 0.088 Uiso 1 1 calc R . . C14 C -0.21250(16) -0.0914(3) 0.38205(16) 0.0763(9) Uani 1 1 d . . . H14A H -0.2407 -0.1169 0.4236 0.092 Uiso 1 1 calc R . . C15 C -0.20834(14) 0.0205(3) 0.36764(14) 0.0618(7) Uani 1 1 d . . . H15A H -0.2343 0.0709 0.3991 0.074 Uiso 1 1 calc R . . C16 C -0.16548(12) 0.05891(19) 0.30632(12) 0.0439(5) Uani 1 1 d . . . H16A H -0.1630 0.1350 0.2968 0.053 Uiso 1 1 calc R . . C21 C 0.19460(13) 0.1554(2) -0.04772(13) 0.0542(6) Uani 1 1 d . . . H21A H 0.2497 0.1308 -0.0408 0.081 Uiso 1 1 calc R . . H21B H 0.1934 0.2352 -0.0513 0.081 Uiso 1 1 calc R . . H21C H 0.1732 0.1235 -0.0927 0.081 Uiso 1 1 calc R . . C22 C 0.08206(17) -0.16246(18) 0.23733(14) 0.0487(5) Uani 1 1 d . . . C23 C 0.03673(19) -0.0351(3) 0.40031(13) 0.0678(7) Uani 1 1 d . . . H23A H 0.0562 0.0032 0.4438 0.102 Uiso 1 1 calc R . . H23B H 0.0487 -0.1132 0.4046 0.102 Uiso 1 1 calc R . . H23C H -0.0210 -0.0249 0.3960 0.102 Uiso 1 1 calc R . . N1 N 0.04699(9) -0.05195(11) 0.25195(8) 0.0303(3) Uani 1 1 d . . . H22A H 0.0985(18) -0.194(3) 0.2806(19) 0.076(9) Uiso 1 1 d . . . H22B H 0.0411(18) -0.205(3) 0.2117(18) 0.076(9) Uiso 1 1 d . . . H22C H 0.132(2) -0.154(3) 0.207(2) 0.114(13) Uiso 1 1 d . . . H1A H -0.2198(19) 0.076(2) 0.1632(17) 0.074(9) Uiso 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 0.0460(3) 0.0363(3) 0.0298(2) -0.00106(17) -0.00711(18) -0.00271(19) O1 0.0253(6) 0.0631(10) 0.0581(9) 0.0222(8) 0.0029(6) 0.0044(6) O2 0.0317(7) 0.0706(10) 0.0376(7) 0.0129(7) 0.0070(6) -0.0034(6) O3 0.1176(16) 0.0335(8) 0.0422(8) -0.0067(6) -0.0153(9) 0.0045(9) O4 0.0414(9) 0.0966(15) 0.0780(13) -0.0154(10) -0.0198(9) -0.0092(9) C1 0.0370(9) 0.0415(10) 0.0349(9) 0.0027(8) -0.0070(7) 0.0046(8) C2 0.0538(11) 0.0444(11) 0.0294(9) 0.0062(8) -0.0079(8) 0.0039(9) C3 0.0489(11) 0.0450(10) 0.0270(8) 0.0062(7) 0.0026(8) -0.0059(8) C4 0.0344(9) 0.0402(9) 0.0272(8) -0.0002(7) 0.0003(7) -0.0066(7) C5 0.0294(8) 0.0310(8) 0.0252(8) -0.0005(6) -0.0013(6) -0.0029(6) C6 0.0235(7) 0.0360(9) 0.0286(8) 0.0001(7) 0.0007(6) -0.0006(6) C7 0.0287(8) 0.0259(7) 0.0254(7) 0.0001(6) -0.0023(6) 0.0006(6) C8 0.0274(8) 0.0267(8) 0.0289(8) -0.0004(6) 0.0023(6) -0.0021(6) C9 0.0243(8) 0.0340(8) 0.0347(9) 0.0011(7) -0.0002(6) 0.0000(6) C10 0.0306(8) 0.0298(8) 0.0284(8) 0.0006(6) -0.0039(6) -0.0019(6) C11 0.0276(8) 0.0368(9) 0.0333(9) 0.0053(7) 0.0017(7) -0.0028(7) C12 0.0454(11) 0.0416(11) 0.0632(14) 0.0121(10) 0.0070(10) -0.0046(9) C13 0.0583(15) 0.0683(17) 0.094(2) 0.0452(16) 0.0095(15) -0.0127(13) C14 0.0496(14) 0.116(2) 0.0630(16) 0.0397(17) 0.0192(12) -0.0058(15) C15 0.0422(12) 0.098(2) 0.0453(12) 0.0052(12) 0.0161(10) 0.0030(12) C16 0.0372(10) 0.0516(11) 0.0430(10) 0.0008(9) 0.0087(8) -0.0003(9) C21 0.0420(11) 0.0800(16) 0.0405(11) 0.0030(11) 0.0112(9) -0.0162(11) C22 0.0625(15) 0.0330(10) 0.0505(12) -0.0028(9) -0.0132(11) 0.0132(10) C23 0.094(2) 0.0799(18) 0.0296(11) 0.0108(11) 0.0021(11) 0.0025(15) N1 0.0359(8) 0.0269(6) 0.0280(7) 0.0009(5) -0.0032(6) 0.0025(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 O3 1.4220(17) . ? S1 O4 1.4249(19) . ? S1 N1 1.6207(14) . ? S1 C23 1.758(2) . ? O1 C9 1.364(2) . ? O2 C4 1.364(2) . ? O2 C21 1.427(2) . ? C1 C2 1.361(3) . ? C1 C10 1.419(2) . ? C2 C3 1.402(3) . ? C3 C4 1.368(3) . ? C4 C5 1.433(2) . ? C5 C6 1.411(2) . ? C5 C10 1.416(2) . ? C6 C7 1.369(2) . ? C7 C8 1.424(2) . ? C7 N1 1.444(2) . ? C8 C9 1.380(2) . ? C8 C11 1.492(2) . ? C9 C10 1.426(2) . ? C11 C12 1.391(3) . ? C11 C16 1.394(3) . ? C12 C13 1.390(3) . ? C13 C14 1.381(5) . ? C14 C15 1.369(4) . ? C15 C16 1.384(3) . ? C22 N1 1.469(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 O3 S1 O4 119.83(13) . . ? O3 S1 N1 107.63(9) . . ? O4 S1 N1 109.81(10) . . ? O3 S1 C23 107.93(13) . . ? O4 S1 C23 106.08(14) . . ? N1 S1 C23 104.52(11) . . ? C4 O2 C21 117.21(16) . . ? C2 C1 C10 119.75(18) . . ? C1 C2 C3 121.60(17) . . ? C4 C3 C2 119.89(17) . . ? O2 C4 C3 124.50(16) . . ? O2 C4 C5 114.68(15) . . ? C3 C4 C5 120.82(17) . . ? C6 C5 C10 119.53(15) . . ? C6 C5 C4 122.41(15) . . ? C10 C5 C4 118.05(15) . . ? C7 C6 C5 120.02(15) . . ? C6 C7 C8 122.26(15) . . ? C6 C7 N1 119.18(15) . . ? C8 C7 N1 118.55(14) . . ? C9 C8 C7 117.62(15) . . ? C9 C8 C11 121.60(15) . . ? C7 C8 C11 120.77(15) . . ? O1 C9 C8 123.89(16) . . ? O1 C9 C10 114.20(15) . . ? C8 C9 C10 121.90(15) . . ? C5 C10 C1 119.85(16) . . ? C5 C10 C9 118.65(15) . . ? C1 C10 C9 121.51(16) . . ? C12 C11 C16 118.94(18) . . ? C12 C11 C8 120.89(17) . . ? C16 C11 C8 120.15(16) . . ? C13 C12 C11 119.7(2) . . ? C14 C13 C12 120.5(2) . . ? C15 C14 C13 120.1(2) . . ? C14 C15 C16 120.1(2) . . ? C15 C16 C11 120.6(2) . . ? C7 N1 C22 118.82(15) . . ? C7 N1 S1 118.72(11) . . ? C22 N1 S1 117.26(13) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.71 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.299 _refine_diff_density_min -0.507 _refine_diff_density_rms 0.067 _publ_section_references ; Sheldrick G.M.(1996), SADABS, Absorption Correction Program, University of Goeltingen, German Siemens(1994), SAINT Software Reference Manual, Siemens Energy & Automation Inc., Madison, Wisconsin, USA Siemens(1996), SMART Software Reference Manual, Siemens Energy & Automation Inc., Madison, Wisconsin, USA Siemens(1994), SHELXTL^TM^ Version 5 Reference Manual, Siemens Energy & Automation Inc., Madison, Wisconsin, USA ;