data_stri_0ma _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H20 N2 O2 S4' _chemical_formula_weight 448.62 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.2084(5) _cell_length_b 30.7322(18) _cell_length_c 7.3395(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.7730(10) _cell_angle_gamma 90.00 _cell_volume 2062.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5072 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 27.43 _exptl_crystal_description Plate-like _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.445 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 0.480 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9018 _exptl_absorpt_correction_T_max 0.9905 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1999)' _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 'Bruker APEX-I CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 19914 _diffrn_reflns_av_R_equivalents 0.0433 _diffrn_reflns_av_sigmaI/netI 0.0322 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.33 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3633 _reflns_number_gt 2928 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0400P)^2^+1.0000P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3633 _refine_ls_number_parameters 255 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0528 _refine_ls_R_factor_gt 0.0392 _refine_ls_wR_factor_ref 0.1071 _refine_ls_wR_factor_gt 0.0914 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _refine_ls_shift/su_max 0.024 _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 0.82033(9) 0.93854(3) 0.96369(11) 0.0606(2) Uani 1 1 d . . . S2 S 0.95768(9) 0.88716(3) 0.96497(12) 0.0662(3) Uani 1 1 d . . . S3 S 0.87086(10) 0.84357(3) 1.13960(11) 0.0658(3) Uani 1 1 d . . . S4 S 0.77145(8) 0.79741(3) 0.97536(11) 0.0554(2) Uani 1 1 d . . . O1 O 0.6769(2) 0.82292(6) 0.5579(2) 0.0506(5) Uani 1 1 d . . . O2 O 0.5113(2) 0.92192(7) 1.0852(3) 0.0615(6) Uani 1 1 d . . . N1 N 0.6744(2) 0.88927(7) 0.6848(3) 0.0376(5) Uani 1 1 d . . . N2 N 0.5361(2) 0.85445(7) 0.9742(3) 0.0382(5) Uani 1 1 d . . . C1 C 0.2923(4) 0.96346(10) 0.7473(5) 0.0620(8) Uani 1 1 d . . . H1 H 0.3038 0.9706 0.8714 0.074 Uiso 1 1 calc R . . C2 C 0.1537(4) 0.96162(12) 0.6528(5) 0.0739(10) Uani 1 1 d . . . H2 H 0.0729 0.9677 0.7136 0.089 Uiso 1 1 calc R . . C3 C 0.1339(4) 0.95086(10) 0.4697(5) 0.0651(9) Uani 1 1 d . . . H3 H 0.0404 0.9499 0.4063 0.078 Uiso 1 1 calc R . . C4 C 0.2532(4) 0.94154(10) 0.3816(4) 0.0573(8) Uani 1 1 d . . . H4 H 0.2408 0.9338 0.2583 0.069 Uiso 1 1 calc R . . C5 C 0.3920(3) 0.94363(9) 0.4757(4) 0.0489(7) Uani 1 1 d . . . H5 H 0.4722 0.9374 0.4142 0.059 Uiso 1 1 calc R . . C6 C 0.4144(3) 0.95483(8) 0.6600(4) 0.0431(6) Uani 1 1 d . . . C7 C 0.5671(3) 0.96055(8) 0.7583(4) 0.0472(7) Uani 1 1 d . . . H7A H 0.5619 0.9800 0.8616 0.057 Uiso 1 1 calc R . . H7B H 0.6268 0.9746 0.6753 0.057 Uiso 1 1 calc R . . C8 C 0.6442(3) 0.91823(8) 0.8297(3) 0.0409(6) Uani 1 1 d . . . C9 C 0.6526(3) 0.84599(8) 0.6868(3) 0.0365(6) Uani 1 1 d . . . C10 C 0.5999(3) 0.82464(8) 0.8557(3) 0.0381(6) Uani 1 1 d . . . C11 C 0.5589(3) 0.89783(9) 0.9737(3) 0.0415(6) Uani 1 1 d . . . C12 C 0.5037(3) 0.78498(8) 0.7991(4) 0.0450(6) Uani 1 1 d . . . H12A H 0.5483 0.7691 0.7058 0.054 Uiso 1 1 calc R . . H12B H 0.5044 0.7660 0.9047 0.054 Uiso 1 1 calc R . . C13 C 0.3465(3) 0.79424(8) 0.7261(3) 0.0395(6) Uani 1 1 d . . . C14 C 0.3036(3) 0.82789(9) 0.6053(4) 0.0492(7) Uani 1 1 d . . . H14 H 0.3735 0.8467 0.5682 0.059 Uiso 1 1 calc R . . C15 C 0.1583(3) 0.83355(10) 0.5399(4) 0.0572(8) Uani 1 1 d . . . H15 H 0.1310 0.8563 0.4597 0.069 Uiso 1 1 calc R . . C16 C 0.0533(3) 0.80599(10) 0.5917(4) 0.0564(8) Uani 1 1 d . . . H16 H -0.0445 0.8099 0.5466 0.068 Uiso 1 1 calc R . . C17 C 0.0942(3) 0.77258(11) 0.7109(4) 0.0592(8) Uani 1 1 d . . . H17 H 0.0239 0.7537 0.7468 0.071 Uiso 1 1 calc R . . C18 C 0.2389(3) 0.76691(10) 0.7775(4) 0.0523(7) Uani 1 1 d . . . H18 H 0.2650 0.7442 0.8587 0.063 Uiso 1 1 calc R . . C19 C 0.7539(3) 0.90604(10) 0.5366(4) 0.0525(7) Uani 1 1 d . . . H19A H 0.6955 0.9020 0.4206 0.063 Uiso 1 1 calc R . . H19B H 0.8446 0.8906 0.5369 0.063 Uiso 1 1 calc R . . H19C H 0.7735 0.9365 0.5558 0.063 Uiso 1 1 calc R . . C20 C 0.4636(4) 0.83660(10) 1.1262(4) 0.0590(8) Uani 1 1 d . . . H20A H 0.4259 0.8600 1.1933 0.071 Uiso 1 1 calc R . . H20B H 0.5330 0.8202 1.2066 0.071 Uiso 1 1 calc R . . H20C H 0.3847 0.8179 1.0779 0.071 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 0.0555(5) 0.0575(5) 0.0652(5) -0.0154(4) -0.0079(4) -0.0093(4) S2 0.0432(4) 0.0778(6) 0.0740(6) -0.0088(5) -0.0072(4) -0.0014(4) S3 0.0647(5) 0.0761(6) 0.0497(4) -0.0026(4) -0.0222(4) 0.0042(4) S4 0.0507(4) 0.0532(4) 0.0577(5) 0.0013(4) -0.0133(3) 0.0122(3) O1 0.0580(12) 0.0529(12) 0.0411(10) -0.0129(9) 0.0070(9) 0.0051(9) O2 0.0837(16) 0.0564(13) 0.0479(11) -0.0111(10) 0.0230(11) 0.0087(11) N1 0.0397(12) 0.0408(12) 0.0330(11) -0.0029(9) 0.0071(9) -0.0006(9) N2 0.0413(12) 0.0408(12) 0.0327(11) -0.0002(9) 0.0049(9) 0.0010(9) C1 0.063(2) 0.062(2) 0.063(2) -0.0087(16) 0.0171(16) 0.0096(16) C2 0.052(2) 0.079(3) 0.094(3) 0.000(2) 0.0221(19) 0.0094(18) C3 0.0486(19) 0.0546(19) 0.090(3) 0.0129(18) 0.0000(17) -0.0007(15) C4 0.063(2) 0.0506(18) 0.0572(18) 0.0079(14) 0.0011(15) -0.0038(15) C5 0.0509(17) 0.0452(16) 0.0514(16) 0.0048(13) 0.0092(13) 0.0012(13) C6 0.0506(16) 0.0268(13) 0.0525(16) 0.0032(11) 0.0089(13) 0.0025(11) C7 0.0555(17) 0.0340(14) 0.0522(16) -0.0030(12) 0.0064(13) -0.0003(12) C8 0.0442(15) 0.0384(14) 0.0402(14) -0.0057(11) 0.0048(11) -0.0005(11) C9 0.0316(13) 0.0421(14) 0.0342(13) -0.0046(11) -0.0029(10) 0.0033(11) C10 0.0381(14) 0.0394(14) 0.0352(13) -0.0016(11) -0.0026(11) 0.0028(11) C11 0.0452(15) 0.0476(16) 0.0309(13) -0.0031(11) 0.0016(11) 0.0031(12) C12 0.0505(16) 0.0364(14) 0.0456(15) 0.0021(12) -0.0042(12) 0.0009(12) C13 0.0442(15) 0.0340(13) 0.0389(13) -0.0020(11) -0.0006(11) -0.0007(11) C14 0.0467(16) 0.0390(15) 0.0589(17) 0.0063(13) -0.0067(13) -0.0080(12) C15 0.0532(18) 0.0443(16) 0.070(2) 0.0071(14) -0.0110(15) 0.0012(14) C16 0.0437(17) 0.0572(19) 0.0663(19) -0.0089(15) -0.0015(14) 0.0030(14) C17 0.0490(18) 0.071(2) 0.0592(19) 0.0030(16) 0.0108(15) -0.0137(15) C18 0.0556(18) 0.0535(17) 0.0465(15) 0.0100(13) 0.0000(13) -0.0068(14) C19 0.0502(17) 0.0602(18) 0.0501(16) 0.0031(14) 0.0185(13) -0.0047(14) C20 0.076(2) 0.063(2) 0.0412(16) 0.0052(14) 0.0174(15) -0.0061(16) _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 C8 1.900(3) . ? S1 S2 2.0224(13) . ? S2 S3 2.0781(14) . ? S3 S4 2.0108(12) . ? S4 C10 1.908(3) . ? O1 C9 1.224(3) . ? O2 C11 1.222(3) . ? N1 C9 1.346(3) . ? N1 C8 1.438(3) . ? N1 C19 1.474(3) . ? N2 C11 1.350(3) . ? N2 C10 1.436(3) . ? N2 C20 1.472(3) . ? C1 C2 1.380(5) . ? C1 C6 1.384(4) . ? C2 C3 1.375(5) . ? C3 C4 1.369(4) . ? C4 C5 1.380(4) . ? C5 C6 1.387(4) . ? C6 C7 1.513(4) . ? C7 C8 1.544(4) . ? C8 C11 1.525(4) . ? C9 C10 1.532(3) . ? C10 C12 1.535(3) . ? C12 C13 1.511(4) . ? C13 C18 1.385(4) . ? C13 C14 1.389(3) . ? C14 C15 1.378(4) . ? C15 C16 1.372(4) . ? C16 C17 1.373(4) . ? C17 C18 1.375(4) . ? 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 C8 S1 S2 103.94(9) . . ? S1 S2 S3 102.72(5) . . ? S4 S3 S2 105.43(5) . . ? C10 S4 S3 105.07(9) . . ? C9 N1 C8 124.2(2) . . ? C9 N1 C19 116.1(2) . . ? C8 N1 C19 119.0(2) . . ? C11 N2 C10 123.6(2) . . ? C11 N2 C20 117.1(2) . . ? C10 N2 C20 118.4(2) . . ? C2 C1 C6 120.9(3) . . ? C3 C2 C1 120.6(3) . . ? C4 C3 C2 119.4(3) . . ? C3 C4 C5 120.1(3) . . ? C4 C5 C6 121.5(3) . . ? C1 C6 C5 117.6(3) . . ? C1 C6 C7 121.1(3) . . ? C5 C6 C7 121.1(3) . . ? C6 C7 C8 115.4(2) . . ? N1 C8 C11 114.7(2) . . ? N1 C8 C7 113.1(2) . . ? C11 C8 C7 109.1(2) . . ? N1 C8 S1 111.01(17) . . ? C11 C8 S1 104.73(17) . . ? C7 C8 S1 103.26(17) . . ? O1 C9 N1 121.6(2) . . ? O1 C9 C10 118.8(2) . . ? N1 C9 C10 119.6(2) . . ? N2 C10 C9 114.1(2) . . ? N2 C10 C12 114.0(2) . . ? C9 C10 C12 110.4(2) . . ? N2 C10 S4 112.14(16) . . ? C9 C10 S4 103.66(16) . . ? C12 C10 S4 101.32(16) . . ? O2 C11 N2 121.9(2) . . ? O2 C11 C8 118.0(2) . . ? N2 C11 C8 120.1(2) . . ? C13 C12 C10 116.4(2) . . ? C18 C13 C14 117.8(3) . . ? C18 C13 C12 118.4(2) . . ? C14 C13 C12 123.7(2) . . ? C15 C14 C13 120.5(3) . . ? C16 C15 C14 120.8(3) . . ? C15 C16 C17 119.3(3) . . ? C16 C17 C18 120.2(3) . . ? C17 C18 C13 121.4(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 C8 S1 S2 S3 -70.73(10) . . . . ? S1 S2 S3 S4 105.37(5) . . . . ? S2 S3 S4 C10 -72.62(10) . . . . ? C6 C1 C2 C3 0.4(5) . . . . ? C1 C2 C3 C4 0.6(5) . . . . ? C2 C3 C4 C5 -1.0(5) . . . . ? C3 C4 C5 C6 0.4(4) . . . . ? C2 C1 C6 C5 -1.0(4) . . . . ? C2 C1 C6 C7 174.7(3) . . . . ? C4 C5 C6 C1 0.6(4) . . . . ? C4 C5 C6 C7 -175.1(2) . . . . ? C1 C6 C7 C8 101.1(3) . . . . ? C5 C6 C7 C8 -83.3(3) . . . . ? C9 N1 C8 C11 -10.6(3) . . . . ? C19 N1 C8 C11 178.9(2) . . . . ? C9 N1 C8 C7 -136.6(2) . . . . ? C19 N1 C8 C7 52.8(3) . . . . ? C9 N1 C8 S1 107.8(2) . . . . ? C19 N1 C8 S1 -62.7(3) . . . . ? C6 C7 C8 N1 65.6(3) . . . . ? C6 C7 C8 C11 -63.3(3) . . . . ? C6 C7 C8 S1 -174.32(19) . . . . ? S2 S1 C8 N1 -35.11(19) . . . . ? S2 S1 C8 C11 89.25(17) . . . . ? S2 S1 C8 C7 -156.56(15) . . . . ? C8 N1 C9 O1 178.3(2) . . . . ? C19 N1 C9 O1 -11.0(3) . . . . ? C8 N1 C9 C10 -3.3(4) . . . . ? C19 N1 C9 C10 167.5(2) . . . . ? C11 N2 C10 C9 -19.6(3) . . . . ? C20 N2 C10 C9 171.6(2) . . . . ? C11 N2 C10 C12 -147.7(2) . . . . ? C20 N2 C10 C12 43.5(3) . . . . ? C11 N2 C10 S4 97.9(2) . . . . ? C20 N2 C10 S4 -70.9(3) . . . . ? O1 C9 C10 N2 -163.3(2) . . . . ? N1 C9 C10 N2 18.2(3) . . . . ? O1 C9 C10 C12 -33.4(3) . . . . ? N1 C9 C10 C12 148.1(2) . . . . ? O1 C9 C10 S4 74.4(2) . . . . ? N1 C9 C10 S4 -104.1(2) . . . . ? S3 S4 C10 N2 -36.23(19) . . . . ? S3 S4 C10 C9 87.34(15) . . . . ? S3 S4 C10 C12 -158.18(15) . . . . ? C10 N2 C11 O2 -174.7(2) . . . . ? C20 N2 C11 O2 -5.8(4) . . . . ? C10 N2 C11 C8 6.2(4) . . . . ? C20 N2 C11 C8 175.0(2) . . . . ? N1 C8 C11 O2 -169.6(2) . . . . ? C7 C8 C11 O2 -41.6(3) . . . . ? S1 C8 C11 O2 68.4(3) . . . . ? N1 C8 C11 N2 9.6(3) . . . . ? C7 C8 C11 N2 137.6(2) . . . . ? S1 C8 C11 N2 -112.4(2) . . . . ? N2 C10 C12 C13 49.6(3) . . . . ? C9 C10 C12 C13 -80.4(3) . . . . ? S4 C10 C12 C13 170.29(19) . . . . ? C10 C12 C13 C18 -140.2(3) . . . . ? C10 C12 C13 C14 42.0(4) . . . . ? C18 C13 C14 C15 0.1(4) . . . . ? C12 C13 C14 C15 178.0(3) . . . . ? C13 C14 C15 C16 -0.4(5) . . . . ? C14 C15 C16 C17 0.3(5) . . . . ? C15 C16 C17 C18 0.0(5) . . . . ? C16 C17 C18 C13 -0.4(5) . . . . ? C14 C13 C18 C17 0.3(4) . . . . ? C12 C13 C18 C17 -177.7(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.182 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.043