data_jr04 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H19 N O3 S2' _chemical_formula_weight 373.47 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.6274(13) _cell_length_b 8.4935(17) _cell_length_c 30.477(6) _cell_angle_alpha 90.00 _cell_angle_beta 92.37(3) _cell_angle_gamma 90.00 _cell_volume 1714.1(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description blade _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.447 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.329 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9222 _exptl_absorpt_correction_T_max 0.9678 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Nonius KappaCCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6248 _diffrn_reflns_av_R_equivalents 0.0565 _diffrn_reflns_av_sigmaI/netI 0.0899 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3723 _reflns_number_gt 2416 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement Denzo _computing_data_reduction Denzo _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material XCIF _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^)+(0.0708P)^2^+6.6750P] 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 3723 _refine_ls_number_parameters 230 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1320 _refine_ls_R_factor_gt 0.0870 _refine_ls_wR_factor_ref 0.2233 _refine_ls_wR_factor_gt 0.2031 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.096 _refine_ls_shift/su_max 0.009 _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 0.76214(19) 0.4504(2) 0.79230(4) 0.0399(4) Uani 1 1 d . . . S2 S 0.3540(2) 0.53157(19) 0.76015(5) 0.0396(4) Uani 1 1 d . . . O1 O 0.4695(6) 0.1976(4) 0.81753(11) 0.0341(9) Uani 1 1 d . . . O2 O 0.4154(5) 0.2293(4) 0.91162(10) 0.0259(8) Uani 1 1 d . . . O3 O 0.6074(5) 0.1612(4) 0.96997(11) 0.0308(9) Uani 1 1 d . . . N1 N 0.2950(6) 0.0551(6) 0.96176(14) 0.0304(10) Uani 1 1 d . . . H1 H 0.322(9) -0.003(7) 0.984(2) 0.042(18) Uiso 1 1 d . . . C1 C 0.4076(7) 0.3274(6) 0.82603(14) 0.0245(11) Uani 1 1 d . . . C2 C 0.5057(8) 0.4780(7) 0.80966(16) 0.0310(12) Uani 1 1 d . . . C3 C 0.4992(10) 0.6095(7) 0.8426(2) 0.0466(16) Uani 1 1 d . . . H3A H 0.6025 0.6870 0.8428 0.056 Uiso 1 1 calc R . . C4 C 0.3564(10) 0.6223(7) 0.8715(2) 0.0456(16) Uani 1 1 d . . . H4A H 0.3659 0.7056 0.8923 0.055 Uiso 1 1 calc R . . C5 C 0.1828(7) 0.5132(6) 0.87313(15) 0.0259(11) Uani 1 1 d . . . H5A H 0.0568 0.5635 0.8606 0.031 Uiso 1 1 calc R . . C6 C 0.2195(7) 0.3507(6) 0.85125(15) 0.0229(10) Uani 1 1 d . . . H6A H 0.0985 0.3213 0.8323 0.027 Uiso 1 1 calc R . . C7 C 0.2092(7) 0.2671(6) 0.89626(14) 0.0219(10) Uani 1 1 d . . . C8 C 0.1424(8) 0.4279(6) 0.91790(15) 0.0278(11) Uani 1 1 d . . . C9 C -0.0792(9) 0.4307(7) 0.9276(2) 0.0448(16) Uani 1 1 d . . . H9A H -0.0995 0.3772 0.9556 0.067 Uiso 1 1 calc R . . H9B H -0.1567 0.3766 0.9040 0.067 Uiso 1 1 calc R . . H9C H -0.1251 0.5400 0.9295 0.067 Uiso 1 1 calc R . . C10 C 0.2725(11) 0.4819(7) 0.95709(19) 0.0484(16) Uani 1 1 d . . . H10A H 0.2368 0.4221 0.9831 0.073 Uiso 1 1 calc R . . H10B H 0.2498 0.5943 0.9622 0.073 Uiso 1 1 calc R . . H10C H 0.4151 0.4642 0.9513 0.073 Uiso 1 1 calc R . . C11 C 0.7099(9) 0.4211(8) 0.73453(18) 0.0444(15) Uani 1 1 d . . . H11A H 0.7552 0.5141 0.7180 0.053 Uiso 1 1 calc R . . H11B H 0.7848 0.3280 0.7244 0.053 Uiso 1 1 calc R . . C12 C 0.4850(10) 0.3966(8) 0.72592(17) 0.0467(16) Uani 1 1 d . . . H12A H 0.4477 0.2868 0.7329 0.056 Uiso 1 1 calc R . . H12B H 0.4482 0.4166 0.6946 0.056 Uiso 1 1 calc R . . C13 C 0.0761(7) 0.1256(6) 0.90052(15) 0.0234(10) Uani 1 1 d . . . C14 C 0.1200(7) 0.0238(6) 0.93551(16) 0.0248(10) Uani 1 1 d . . . C15 C -0.0061(8) -0.1011(6) 0.94493(17) 0.0307(12) Uani 1 1 d . . . H15A H 0.0245 -0.1684 0.9692 0.037 Uiso 1 1 calc R . . C16 C -0.1761(8) -0.1252(6) 0.91845(18) 0.0336(12) Uani 1 1 d . . . H16A H -0.2622 -0.2114 0.9244 0.040 Uiso 1 1 calc R . . C17 C -0.2246(7) -0.0278(6) 0.88351(16) 0.0289(11) Uani 1 1 d . . . H17A H -0.3432 -0.0463 0.8657 0.035 Uiso 1 1 calc R . . C18 C -0.0984(7) 0.0983(6) 0.87459(16) 0.0267(11) Uani 1 1 d . . . H18A H -0.1316 0.1663 0.8506 0.032 Uiso 1 1 calc R . . C19 C 0.4464(7) 0.1488(6) 0.94975(15) 0.0265(11) 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 0.0261(6) 0.0631(11) 0.0307(7) 0.0128(7) 0.0046(5) -0.0008(7) S2 0.0328(7) 0.0493(9) 0.0366(7) 0.0201(7) 0.0000(6) 0.0021(7) O1 0.042(2) 0.033(2) 0.0274(18) -0.0010(16) 0.0083(16) 0.0077(18) O2 0.0269(17) 0.031(2) 0.0193(16) 0.0071(14) 0.0012(13) -0.0003(15) O3 0.0282(18) 0.039(2) 0.0250(18) 0.0106(16) -0.0038(15) -0.0042(16) N1 0.027(2) 0.036(3) 0.028(2) 0.014(2) -0.0003(18) -0.006(2) C1 0.026(2) 0.031(3) 0.016(2) 0.001(2) 0.0011(19) 0.001(2) C2 0.034(3) 0.035(3) 0.025(2) 0.000(2) 0.007(2) -0.004(2) C3 0.057(4) 0.040(4) 0.044(3) -0.014(3) 0.019(3) -0.026(3) C4 0.059(4) 0.031(3) 0.049(4) -0.012(3) 0.029(3) -0.019(3) C5 0.030(2) 0.023(3) 0.025(2) 0.004(2) 0.003(2) 0.001(2) C6 0.026(2) 0.026(3) 0.017(2) 0.0019(19) 0.0005(18) -0.001(2) C7 0.023(2) 0.024(3) 0.018(2) 0.0032(19) -0.0005(18) 0.001(2) C8 0.040(3) 0.022(3) 0.022(2) 0.003(2) 0.006(2) -0.005(2) C9 0.051(4) 0.023(3) 0.063(4) -0.002(3) 0.032(3) 0.006(3) C10 0.078(4) 0.036(3) 0.031(3) -0.009(3) -0.006(3) 0.006(3) C11 0.053(4) 0.052(4) 0.029(3) -0.001(3) 0.014(3) -0.003(3) C12 0.067(4) 0.053(4) 0.020(3) 0.000(3) 0.005(3) -0.023(3) C13 0.028(2) 0.022(3) 0.021(2) 0.0016(19) 0.0060(19) 0.001(2) C14 0.023(2) 0.024(3) 0.028(2) 0.001(2) 0.0020(19) 0.002(2) C15 0.034(3) 0.026(3) 0.033(3) 0.006(2) 0.003(2) -0.002(2) C16 0.035(3) 0.024(3) 0.042(3) 0.000(2) 0.003(2) -0.008(2) C17 0.027(2) 0.028(3) 0.031(3) -0.008(2) -0.002(2) -0.003(2) C18 0.031(3) 0.027(3) 0.022(2) 0.000(2) 0.001(2) -0.003(2) C19 0.031(3) 0.029(3) 0.020(2) 0.004(2) 0.001(2) 0.002(2) _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 C11 1.798(6) . ? S1 C2 1.816(5) . ? S2 C12 1.798(7) . ? S2 C2 1.835(5) . ? O1 C1 1.208(6) . ? O2 C19 1.357(6) . ? O2 C7 1.461(6) . ? O3 C19 1.214(6) . ? N1 C19 1.343(6) . ? N1 C14 1.407(6) . ? C1 C6 1.504(6) . ? C1 C2 1.529(7) . ? C2 C3 1.504(8) . ? C3 C4 1.323(8) . ? C4 C5 1.479(7) . ? C5 C6 1.556(7) . ? C5 C8 1.577(6) . ? C6 C7 1.549(6) . ? C7 C13 1.500(7) . ? C7 C8 1.588(7) . ? C8 C9 1.510(7) . ? C8 C10 1.515(8) . ? C11 C12 1.517(8) . ? C13 C18 1.393(7) . ? C13 C14 1.394(7) . ? C14 C15 1.388(7) . ? C15 C16 1.374(8) . ? C16 C17 1.376(7) . ? C17 C18 1.392(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 C11 S1 C2 99.1(3) . . ? C12 S2 C2 93.3(3) . . ? C19 O2 C7 119.4(4) . . ? C19 N1 C14 124.4(4) . . ? O1 C1 C6 121.7(4) . . ? O1 C1 C2 122.7(4) . . ? C6 C1 C2 115.4(4) . . ? C3 C2 C1 112.2(4) . . ? C3 C2 S1 110.1(4) . . ? C1 C2 S1 113.8(4) . . ? C3 C2 S2 109.6(4) . . ? C1 C2 S2 104.5(3) . . ? S1 C2 S2 106.3(2) . . ? C4 C3 C2 123.1(5) . . ? C3 C4 C5 123.3(5) . . ? C4 C5 C6 114.0(4) . . ? C4 C5 C8 118.4(5) . . ? C6 C5 C8 89.9(4) . . ? C1 C6 C7 117.4(4) . . ? C1 C6 C5 118.9(4) . . ? C7 C6 C5 90.8(3) . . ? O2 C7 C13 110.0(4) . . ? O2 C7 C6 108.0(4) . . ? C13 C7 C6 119.4(4) . . ? O2 C7 C8 109.2(4) . . ? C13 C7 C8 118.6(4) . . ? C6 C7 C8 89.8(4) . . ? C9 C8 C10 111.5(5) . . ? C9 C8 C5 111.3(5) . . ? C10 C8 C5 115.6(5) . . ? C9 C8 C7 112.6(4) . . ? C10 C8 C7 115.4(5) . . ? C5 C8 C7 88.6(3) . . ? C12 C11 S1 109.6(4) . . ? C11 C12 S2 107.9(4) . . ? C18 C13 C14 118.2(4) . . ? C18 C13 C7 124.2(4) . . ? C14 C13 C7 117.3(4) . . ? C15 C14 C13 121.6(5) . . ? C15 C14 N1 121.1(5) . . ? C13 C14 N1 117.3(4) . . ? C16 C15 C14 118.6(5) . . ? C15 C16 C17 121.6(5) . . ? C16 C17 C18 119.4(5) . . ? C17 C18 C13 120.6(5) . . ? O3 C19 N1 124.3(5) . . ? O3 C19 O2 119.3(4) . . ? N1 C19 O2 116.3(4) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.871 _refine_diff_density_min -0.364 _refine_diff_density_rms 0.094