# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2002 data_global _journal_coden_Cambridge 440 _publ_requested_journal 'New Journal of Chemistry' loop_ _publ_author_name 'Mark R.J. Elsegood' 'Kathryn E. Holmes' 'Paul F. Kelly' 'Jonathan Parr' 'Julia M. Stonehouse' _publ_contact_author_name 'Dr P F Kelly' _publ_contact_author_address ; Dr P F Kelly Department of Chemistry Loughborough University Loughborough LE11 3TU UNITED KINGDOM ; _publ_contact_author_email 'P.F.KELLY@LBORO.AC.UK' data_1a _database_code_CSD 157266 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H20 N2 O2 S2' _chemical_formula_weight 360.48 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 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 15.9838(16) _cell_length_b 5.2038(5) _cell_length_c 20.426(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1698.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1641 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 25.28 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.409 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.327 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.947 _exptl_absorpt_correction_T_max 0.997 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 13039 _diffrn_reflns_av_R_equivalents 0.1024 _diffrn_reflns_av_sigmaI/netI 0.0745 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 27.49 _reflns_number_total 1943 _reflns_number_gt 1152 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0399P)^2^+3.0515P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary 'all non-H atoms found by direct methods' _atom_sites_solution_hydrogens 'geom except NH & OH coords freely refined' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1943 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1068 _refine_ls_R_factor_gt 0.0527 _refine_ls_wR_factor_ref 0.1278 _refine_ls_wR_factor_gt 0.1021 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 N1 N 0.69738(16) 0.0305(6) 0.52324(13) 0.0210(6) Uani 1 1 d . . . H1 H 0.726(2) 0.181(7) 0.5304(17) 0.031 Uiso 1 1 d . . . S1 S 0.60849(5) 0.03649(15) 0.55681(4) 0.0191(2) Uani 1 1 d . . . C1 C 0.6150(2) 0.1241(6) 0.64157(15) 0.0183(7) Uani 1 1 d . . . C2 C 0.5752(2) -0.0364(7) 0.68532(16) 0.0267(8) Uani 1 1 d . . . H2 H 0.5439 -0.1794 0.6700 0.032 Uiso 1 1 calc R . . C3 C 0.5812(2) 0.0129(7) 0.75206(18) 0.0332(9) Uani 1 1 d . . . H3 H 0.5541 -0.0972 0.7825 0.040 Uiso 1 1 calc R . . C4 C 0.6264(2) 0.2212(8) 0.77407(18) 0.0299(9) Uani 1 1 d . . . H4 H 0.6298 0.2556 0.8197 0.036 Uiso 1 1 calc R . . C5 C 0.6667(2) 0.3801(8) 0.73011(18) 0.0300(9) Uani 1 1 d . . . H5 H 0.6984 0.5219 0.7456 0.036 Uiso 1 1 calc R . . C6 C 0.6610(2) 0.3335(7) 0.66325(17) 0.0266(8) Uani 1 1 d . . . H6 H 0.6882 0.4434 0.6329 0.032 Uiso 1 1 calc R . . C7 C 0.54899(19) 0.3101(6) 0.52730(16) 0.0186(7) Uani 1 1 d . . . C8 C 0.5761(2) 0.4355(7) 0.47140(15) 0.0206(7) Uani 1 1 d . . . H8 H 0.6279 0.3898 0.4519 0.025 Uiso 1 1 calc R . . C9 C 0.52739(19) 0.6278(6) 0.44392(16) 0.0199(7) Uani 1 1 d . . . H9 H 0.5459 0.7163 0.4059 0.024 Uiso 1 1 calc R . . O1 O 0.71044(18) 0.9011(5) 0.38830(14) 0.0307(7) Uani 1 1 d . . . H1A H 0.703(2) 0.902(8) 0.432(2) 0.046 Uiso 1 1 d . . . H1B H 0.728(3) 0.778(9) 0.385(2) 0.046 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 N1 0.0183(14) 0.0215(15) 0.0231(15) -0.0009(13) 0.0041(11) 0.0017(12) S1 0.0194(4) 0.0193(4) 0.0186(4) -0.0013(4) -0.0004(3) 0.0004(4) C1 0.0200(16) 0.0197(16) 0.0154(16) 0.0002(13) -0.0018(13) 0.0033(14) C2 0.0296(18) 0.0248(19) 0.0258(19) 0.0002(16) -0.0003(15) -0.0029(16) C3 0.041(2) 0.034(2) 0.0247(19) 0.0036(17) 0.0061(17) -0.0011(18) C4 0.030(2) 0.041(2) 0.0182(18) -0.0035(16) -0.0036(15) 0.0070(17) C5 0.0215(18) 0.035(2) 0.033(2) -0.0104(18) -0.0051(16) 0.0009(17) C6 0.0258(18) 0.028(2) 0.026(2) 0.0002(16) -0.0002(15) -0.0034(16) C7 0.0173(15) 0.0217(18) 0.0168(16) -0.0054(14) -0.0034(13) 0.0005(13) C8 0.0155(15) 0.0286(19) 0.0175(16) -0.0035(15) 0.0032(13) -0.0019(14) C9 0.0196(16) 0.0248(17) 0.0154(16) 0.0013(15) 0.0005(14) 0.0001(13) O1 0.0404(16) 0.0274(15) 0.0243(14) 0.0024(12) 0.0011(12) 0.0053(12) _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 N1 S1 1.578(3) . ? S1 C1 1.793(3) . ? S1 C7 1.815(3) . ? C1 C2 1.379(5) . ? C1 C6 1.387(5) . ? C2 C3 1.391(5) . ? C3 C4 1.378(5) . ? C4 C5 1.380(5) . ? C5 C6 1.390(5) . ? C7 C8 1.384(4) . ? C7 C9 1.393(4) 5_666 ? C8 C9 1.387(4) . ? C9 C7 1.393(4) 5_666 ? 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 C1 111.86(15) . . ? N1 S1 C7 110.06(15) . . ? C1 S1 C7 98.72(14) . . ? C2 C1 C6 120.9(3) . . ? C2 C1 S1 116.4(3) . . ? C6 C1 S1 122.6(3) . . ? C1 C2 C3 119.5(3) . . ? C4 C3 C2 120.1(3) . . ? C3 C4 C5 120.2(3) . . ? C4 C5 C6 120.3(3) . . ? C1 C6 C5 119.0(3) . . ? C8 C7 C9 120.9(3) . 5_666 ? C8 C7 S1 118.7(2) . . ? C9 C7 S1 120.1(3) 5_666 . ? C7 C8 C9 119.9(3) . . ? C8 C9 C7 119.2(3) . 5_666 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 N1 0.92(4) 2.20(4) 3.098(3) 167(3) 8_765 O1 H1A N1 0.89(4) 1.99(4) 2.845(4) 160(4) 1_565 O1 H1B O1 0.70(5) 2.19(5) 2.893(2) 173(5) 8_755 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.718 _refine_diff_density_min -0.472 _refine_diff_density_rms 0.090 #===END data_1b _database_code_CSD 162725 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H16 N2 S2' _chemical_formula_weight 324.45 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' '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 5.5099(2) _cell_length_b 8.5604(4) _cell_length_c 16.5197(7) _cell_angle_alpha 90.00 _cell_angle_beta 92.699(2) _cell_angle_gamma 90.00 _cell_volume 778.32(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5354 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 28.74 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.384 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 340 _exptl_absorpt_coefficient_mu 0.339 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.885 _exptl_absorpt_correction_T_max 0.932 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 6503 _diffrn_reflns_av_R_equivalents 0.0112 _diffrn_reflns_av_sigmaI/netI 0.0097 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 28.76 _reflns_number_total 1844 _reflns_number_gt 1790 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0295P)^2^+0.7340P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary 'all non-H atoms found by direct methods' _atom_sites_solution_hydrogens 'geom except NH freely refined' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1844 _refine_ls_number_parameters 109 _refine_ls_number_restraints 14 _refine_ls_R_factor_all 0.0407 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.0982 _refine_ls_wR_factor_gt 0.0979 _refine_ls_goodness_of_fit_ref 1.230 _refine_ls_restrained_S_all 1.225 _refine_ls_shift/su_max 0.000 _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 N1 N 0.2525(5) 0.5652(2) 0.02460(11) 0.0364(5) Uani 1 1 d DU . . H1 H 0.141(7) 0.534(6) 0.005(3) 0.041(14) Uiso 0.59(5) 1 d PDU A 1 H1X H 0.378(8) 0.542(9) 0.019(4) 0.05(2) Uiso 0.41(5) 1 d PDU A 2 S1 S 0.20261(8) 0.71890(5) 0.07314(3) 0.02270(14) Uani 1 1 d . . . C1 C 0.3709(3) 0.7169(2) 0.16972(10) 0.0206(3) Uani 1 1 d . . . C2 C 0.2843(4) 0.8085(2) 0.23143(11) 0.0266(4) Uani 1 1 d . . . H2 H 0.1390 0.8672 0.2229 0.032 Uiso 1 1 calc R . . C3 C 0.4129(4) 0.8133(2) 0.30585(12) 0.0318(4) Uani 1 1 d . . . H3 H 0.3563 0.8760 0.3485 0.038 Uiso 1 1 calc R . . C4 C 0.6232(4) 0.7265(2) 0.31766(12) 0.0325(4) Uani 1 1 d . . . H4 H 0.7122 0.7311 0.3683 0.039 Uiso 1 1 calc R . . C5 C 0.7054(4) 0.6329(2) 0.25625(12) 0.0317(4) Uani 1 1 d . . . H5 H 0.8487 0.5725 0.2652 0.038 Uiso 1 1 calc R . . C6 C 0.5785(3) 0.6272(2) 0.18147(11) 0.0263(4) Uani 1 1 d . . . H6 H 0.6335 0.5628 0.1392 0.032 Uiso 1 1 calc R . . C7 C 0.3744(3) 0.8773(2) 0.03165(10) 0.0206(3) Uani 1 1 d . . . C8 C 0.3009(3) 1.0291(2) 0.04644(11) 0.0246(4) Uani 1 1 d . . . H8 H 0.1642 1.0480 0.0780 0.030 Uiso 1 1 calc R . . C9 C 0.4283(3) 1.1538(2) 0.01473(11) 0.0241(4) Uani 1 1 d . . . H9 H 0.3806 1.2584 0.0247 0.029 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 N1 0.0581(14) 0.0227(9) 0.0280(9) -0.0041(7) -0.0030(9) -0.0087(9) S1 0.0236(2) 0.0215(2) 0.0226(2) 0.00173(16) -0.00214(16) -0.00540(16) C1 0.0229(8) 0.0199(8) 0.0190(8) 0.0018(6) 0.0002(6) -0.0049(6) C2 0.0302(9) 0.0244(9) 0.0256(9) 0.0017(7) 0.0052(7) 0.0016(7) C3 0.0474(12) 0.0274(9) 0.0211(9) -0.0019(7) 0.0064(8) -0.0042(8) C4 0.0398(11) 0.0351(11) 0.0220(9) 0.0045(8) -0.0063(8) -0.0086(9) C5 0.0265(9) 0.0349(11) 0.0333(10) 0.0060(8) -0.0034(8) 0.0013(8) C6 0.0272(9) 0.0269(9) 0.0248(9) 0.0005(7) 0.0029(7) 0.0010(7) C7 0.0248(8) 0.0191(8) 0.0175(7) 0.0024(6) -0.0033(6) -0.0044(6) C8 0.0261(9) 0.0244(9) 0.0236(8) 0.0002(7) 0.0045(7) -0.0004(7) C9 0.0292(9) 0.0179(8) 0.0253(9) 0.0001(6) 0.0013(7) -0.0004(7) _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 N1 S1 1.571(2) . ? N1 H1 0.73(3) . ? N1 H1X 0.73(4) . ? S1 C7 1.8071(17) . ? S1 C1 1.8073(18) . ? C1 C6 1.384(3) . ? C1 C2 1.389(2) . ? C2 C3 1.390(3) . ? C2 H2 0.9500 . ? C3 C4 1.383(3) . ? C3 H3 0.9500 . ? C4 C5 1.385(3) . ? C4 H4 0.9500 . ? C5 C6 1.391(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C9 1.385(3) 3_675 ? C7 C8 1.387(2) . ? C8 C9 1.393(2) . ? C8 H8 0.9500 . ? C9 C7 1.385(3) 3_675 ? C9 H9 0.9500 . ? 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 S1 N1 H1 112(4) . . ? S1 N1 H1X 119(6) . . ? H1 N1 H1X 129(7) . . ? N1 S1 C7 109.11(10) . . ? N1 S1 C1 110.35(10) . . ? C7 S1 C1 94.93(8) . . ? C6 C1 C2 121.39(17) . . ? C6 C1 S1 121.03(14) . . ? C2 C1 S1 117.58(14) . . ? C1 C2 C3 119.17(18) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? C4 C3 C2 119.87(18) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 120.52(18) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C4 C5 C6 120.19(19) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C1 C6 C5 118.84(18) . . ? C1 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? C9 C7 C8 121.42(16) 3_675 . ? C9 C7 S1 120.28(14) 3_675 . ? C8 C7 S1 118.29(14) . . ? C7 C8 C9 119.69(16) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C7 C9 C8 118.89(16) 3_675 . ? C7 C9 H9 120.6 3_675 . ? C8 C9 H9 120.6 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 N1 0.73(3) 2.36(4) 3.072(5) 166(5) 3_565 N1 H1X N1 0.73(4) 2.38(4) 3.092(5) 167(8) 3_665 _diffrn_measured_fraction_theta_max 0.911 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.560 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.054 #===END data_2a _database_code_CSD 162726 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H17 N O S2' _chemical_formula_weight 327.45 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 20.698(6) _cell_length_b 28.122(8) _cell_length_c 5.5475(15) _cell_angle_alpha 90.00 _cell_angle_beta 94.837(5) _cell_angle_gamma 90.00 _cell_volume 3217.5(15) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1781 _cell_measurement_theta_min 2.93 _cell_measurement_theta_max 28.27 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.85 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.352 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1376 _exptl_absorpt_coefficient_mu 0.332 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.766 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 18565 _diffrn_reflns_av_R_equivalents 0.2399 _diffrn_reflns_av_sigmaI/netI 0.1905 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 0.99 _diffrn_reflns_theta_max 22.50 _reflns_number_total 4187 _reflns_number_gt 2259 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.1294P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geom except NH and OH coords freely refined' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.058(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4187 _refine_ls_number_parameters 410 _refine_ls_number_restraints 341 _refine_ls_R_factor_all 0.1898 _refine_ls_R_factor_gt 0.0995 _refine_ls_wR_factor_ref 0.2570 _refine_ls_wR_factor_gt 0.2108 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.000 _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 0.08803(10) 0.67116(8) 0.4670(4) 0.0200(7) Uani 1 1 d U . . N1 N 0.0530(3) 0.7215(3) 0.4457(15) 0.0214(19) Uani 1 1 d U . . H1A H 0.059(4) 0.733(3) 0.598(17) 0.032 Uiso 1 1 d . . . C1 C 0.1703(4) 0.6784(3) 0.5970(16) 0.0203(15) Uani 1 1 d U . . C2 C 0.1858(4) 0.6983(3) 0.8163(17) 0.0215(17) Uani 1 1 d U . . H2 H 0.1527 0.7084 0.9135 0.026 Uiso 1 1 calc R . . C3 C 0.2503(4) 0.7038(3) 0.8972(18) 0.026(2) Uani 1 1 d U . . H3 H 0.2615 0.7185 1.0492 0.031 Uiso 1 1 calc R . . C4 C 0.2989(5) 0.6882(3) 0.760(2) 0.031(2) Uani 1 1 d U . . H4 H 0.3431 0.6906 0.8209 0.037 Uiso 1 1 calc R . . C5 C 0.2828(4) 0.6692(3) 0.5346(19) 0.030(2) Uani 1 1 d U . . H5 H 0.3157 0.6598 0.4349 0.036 Uiso 1 1 calc R . . C6 C 0.2184(4) 0.6639(3) 0.4551(17) 0.0222(19) Uani 1 1 d U . . H6 H 0.2068 0.6501 0.3011 0.027 Uiso 1 1 calc R . . C7 C 0.0570(4) 0.6365(3) 0.7054(16) 0.021(2) Uani 1 1 d U . . C8 C 0.0115(4) 0.6563(3) 0.8392(17) 0.025(2) Uani 1 1 d U . . H8 H -0.0005 0.6886 0.8125 0.030 Uiso 1 1 calc R . . C9 C -0.0178(4) 0.6304(3) 1.0135(17) 0.024(2) Uani 1 1 d U . . H9 H -0.0489 0.6448 1.1069 0.029 Uiso 1 1 calc R . . C10 C -0.0005(4) 0.5828(3) 1.0483(18) 0.028(2) Uani 1 1 d U . . H10 H -0.0197 0.5645 1.1671 0.034 Uiso 1 1 calc R . . C11 C 0.0448(4) 0.5621(3) 0.9096(18) 0.029(2) Uani 1 1 d U . . H11 H 0.0553 0.5294 0.9308 0.035 Uiso 1 1 calc R . . C12 C 0.0744(4) 0.5885(3) 0.7422(17) 0.025(2) Uani 1 1 d U . . S2 S 0.13468(14) 0.56471(9) 0.5652(6) 0.0455(10) Uani 1 1 d U . . C13 C 0.1376(4) 0.5028(3) 0.6296(17) 0.022(2) Uani 1 1 d U . . C14 C 0.1097(5) 0.4707(3) 0.4699(18) 0.031(2) Uani 1 1 d U . . H14 H 0.0837 0.4817 0.3317 0.037 Uiso 1 1 calc R . . C15 C 0.1183(5) 0.4235(4) 0.504(2) 0.041(3) Uani 1 1 d U . . H15 H 0.0995 0.4018 0.3872 0.049 Uiso 1 1 calc R . . C16 C 0.1535(5) 0.4067(4) 0.703(2) 0.038(3) Uani 1 1 d U . . H16 H 0.1582 0.3734 0.7272 0.045 Uiso 1 1 calc R . . C17 C 0.1821(5) 0.4377(4) 0.869(2) 0.035(2) Uani 1 1 d U . . H17 H 0.2071 0.4260 1.0083 0.043 Uiso 1 1 calc R . . C18 C 0.1747(4) 0.4864(3) 0.8348(18) 0.031(2) Uani 1 1 d U . . H18 H 0.1946 0.5082 0.9490 0.037 Uiso 1 1 calc R . . S3 S 0.41997(10) 0.32767(8) 0.9183(4) 0.0201(7) Uani 1 1 d U . . N2 N 0.4515(4) 0.2761(3) 0.9189(15) 0.027(2) Uani 1 1 d U . . H2A H 0.450(4) 0.263(3) 1.080(18) 0.041 Uiso 1 1 d . . . C19 C 0.3436(4) 0.3234(3) 1.0435(16) 0.019(2) Uani 1 1 d U . . C20 C 0.2947(4) 0.2992(3) 0.9023(18) 0.025(2) Uani 1 1 d U . . H20 H 0.3042 0.2843 0.7557 0.030 Uiso 1 1 calc R . . C21 C 0.2322(4) 0.2970(3) 0.9767(19) 0.030(2) Uani 1 1 d U . . H21 H 0.1988 0.2812 0.8796 0.036 Uiso 1 1 calc R . . C22 C 0.2188(5) 0.3182(3) 1.195(2) 0.035(2) Uani 1 1 d U . . H22 H 0.1763 0.3166 1.2472 0.042 Uiso 1 1 calc R . . C23 C 0.2664(5) 0.3409(3) 1.3315(19) 0.031(2) Uani 1 1 d U . . H23 H 0.2567 0.3552 1.4794 0.038 Uiso 1 1 calc R . . C24 C 0.3283(4) 0.3440(3) 1.2622(17) 0.025(2) Uani 1 1 d U . . H24 H 0.3608 0.3600 1.3622 0.029 Uiso 1 1 calc R . . C25 C 0.4623(4) 0.3655(3) 1.1392(16) 0.0168(19) Uani 1 1 d U . . C26 C 0.5040(4) 0.3449(3) 1.3236(17) 0.022(2) Uani 1 1 d U . . H26 H 0.5091 0.3114 1.3307 0.026 Uiso 1 1 calc R . . C27 C 0.5375(4) 0.3733(3) 1.4943(18) 0.026(2) Uani 1 1 d U . . H27 H 0.5645 0.3591 1.6214 0.031 Uiso 1 1 calc R . . C28 C 0.5319(4) 0.4223(3) 1.4813(19) 0.028(2) Uani 1 1 d U . . H28 H 0.5551 0.4416 1.5993 0.034 Uiso 1 1 calc R . . C29 C 0.4920(4) 0.4433(3) 1.2939(17) 0.025(2) Uani 1 1 d U . . H29 H 0.4894 0.4769 1.2818 0.030 Uiso 1 1 calc R . . C30 C 0.4565(4) 0.4152(3) 1.1269(16) 0.0187(19) Uani 1 1 d U . . S4 S 0.40574(12) 0.44214(8) 0.8906(4) 0.0263(7) Uani 1 1 d U . . C31 C 0.3627(4) 0.4840(3) 1.0586(16) 0.020(2) Uani 1 1 d U . . C32 C 0.3328(4) 0.4715(3) 1.2619(17) 0.027(2) Uani 1 1 d U . . H32 H 0.3369 0.4400 1.3224 0.032 Uiso 1 1 calc R . . C33 C 0.2973(4) 0.5040(3) 1.3778(18) 0.031(2) Uani 1 1 d U . . H33 H 0.2777 0.4951 1.5198 0.037 Uiso 1 1 calc R . . C34 C 0.2898(5) 0.5493(4) 1.291(2) 0.035(3) Uani 1 1 d U . . H34 H 0.2651 0.5717 1.3728 0.042 Uiso 1 1 calc R . . C35 C 0.3178(5) 0.5624(3) 1.086(2) 0.037(3) Uani 1 1 d U . . H35 H 0.3119 0.5939 1.0255 0.045 Uiso 1 1 calc R . . C36 C 0.3546(4) 0.5303(3) 0.9652(18) 0.027(2) Uani 1 1 d U . . H36 H 0.3739 0.5395 0.8228 0.033 Uiso 1 1 calc R . . O1 O -0.0847(3) 0.7308(3) 0.3498(13) 0.038(2) Uani 1 1 d D . . H1B H -0.043(3) 0.725(4) 0.36(2) 0.057 Uiso 1 1 d D . . H1C H -0.107(5) 0.744(4) 0.461(16) 0.057 Uiso 1 1 d D . . O2 O 0.5842(3) 0.2722(2) 0.8337(12) 0.0317(18) 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 0.0244(13) 0.0131(13) 0.0219(15) 0.0008(11) -0.0011(10) -0.0002(10) N1 0.021(4) 0.019(4) 0.022(5) 0.007(4) -0.006(4) 0.005(3) C1 0.0212(16) 0.0191(18) 0.0204(17) 0.0005(10) 0.0015(9) 0.0000(10) C2 0.034(3) 0.007(4) 0.022(3) 0.003(3) -0.001(3) -0.005(4) C3 0.038(4) 0.013(5) 0.026(5) 0.002(4) -0.004(3) -0.009(4) C4 0.027(5) 0.015(6) 0.048(6) 0.003(5) -0.011(4) -0.002(4) C5 0.022(4) 0.030(6) 0.039(6) 0.001(5) 0.000(4) 0.002(4) C6 0.024(2) 0.017(5) 0.026(4) 0.003(4) 0.002(3) 0.001(4) C7 0.023(5) 0.019(4) 0.022(6) 0.002(4) -0.002(4) -0.006(4) C8 0.021(5) 0.021(5) 0.031(6) 0.001(4) -0.001(4) -0.002(4) C9 0.023(5) 0.027(5) 0.023(6) -0.007(5) 0.000(4) -0.006(4) C10 0.031(6) 0.023(5) 0.030(6) 0.002(5) 0.001(4) -0.008(4) C11 0.036(6) 0.011(5) 0.041(6) 0.008(4) 0.004(4) -0.005(4) C12 0.033(6) 0.014(4) 0.027(6) 0.000(4) 0.006(4) -0.003(4) S2 0.062(2) 0.0098(15) 0.070(2) 0.0116(14) 0.0367(17) 0.0089(13) C13 0.028(5) 0.011(4) 0.029(6) 0.006(4) 0.005(4) 0.002(4) C14 0.035(6) 0.030(5) 0.024(6) 0.003(4) -0.008(4) -0.014(5) C15 0.061(7) 0.030(5) 0.034(6) -0.007(5) 0.008(5) -0.012(5) C16 0.047(7) 0.020(5) 0.049(7) 0.008(5) 0.020(5) 0.006(5) C17 0.035(6) 0.035(6) 0.036(6) 0.017(5) -0.004(5) 0.004(5) C18 0.032(6) 0.026(5) 0.033(6) 0.004(4) -0.008(4) -0.014(4) S3 0.0254(14) 0.0124(13) 0.0222(15) -0.0014(11) 0.0007(11) 0.0012(10) N2 0.040(5) 0.013(4) 0.030(5) -0.003(4) 0.007(4) -0.002(3) C19 0.022(4) 0.015(5) 0.019(5) 0.008(4) -0.007(4) -0.005(4) C20 0.032(5) 0.012(5) 0.029(6) -0.008(4) -0.008(4) 0.005(4) C21 0.022(5) 0.015(5) 0.050(7) -0.003(5) -0.014(5) -0.003(4) C22 0.022(5) 0.031(6) 0.053(7) 0.012(5) 0.003(5) 0.005(4) C23 0.040(5) 0.026(6) 0.030(6) -0.003(5) 0.008(4) -0.003(5) C24 0.029(5) 0.020(5) 0.024(5) -0.005(4) -0.004(4) -0.005(4) C25 0.016(4) 0.016(4) 0.018(5) -0.001(4) 0.000(4) -0.002(4) C26 0.020(5) 0.012(5) 0.033(6) -0.005(4) 0.000(4) 0.000(4) C27 0.027(5) 0.027(5) 0.024(6) -0.009(4) -0.004(4) -0.001(4) C28 0.027(5) 0.020(5) 0.036(6) -0.010(5) -0.002(4) -0.006(4) C29 0.029(5) 0.009(5) 0.036(6) -0.005(4) 0.005(4) -0.004(4) C30 0.019(5) 0.013(4) 0.025(5) 0.004(4) 0.007(4) -0.004(3) S4 0.0380(16) 0.0178(14) 0.0224(15) -0.0013(12) -0.0006(12) 0.0083(11) C31 0.018(5) 0.019(5) 0.020(5) -0.006(4) -0.009(4) -0.002(4) C32 0.029(5) 0.022(5) 0.027(6) -0.004(4) -0.004(4) 0.005(4) C33 0.031(6) 0.030(6) 0.031(6) -0.006(5) 0.003(5) 0.007(5) C34 0.036(6) 0.029(5) 0.042(6) -0.014(5) 0.002(5) 0.009(5) C35 0.037(6) 0.020(5) 0.053(7) 0.000(5) -0.006(5) 0.007(5) C36 0.035(6) 0.015(5) 0.031(6) 0.002(4) -0.002(4) 0.000(4) O1 0.027(4) 0.045(5) 0.040(5) -0.002(4) -0.004(4) 0.003(4) O2 0.030(4) 0.029(4) 0.035(5) 0.001(3) -0.008(3) 0.001(3) _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 1.590(8) . ? S1 C1 1.803(9) . ? S1 C7 1.803(9) . ? C1 C2 1.354(12) . ? C1 C6 1.381(12) . ? C2 C3 1.381(12) . ? C3 C4 1.383(13) . ? C4 C5 1.374(14) . ? C5 C6 1.378(12) . ? C7 C8 1.366(12) . ? C7 C12 1.409(12) . ? C8 C9 1.390(12) . ? C9 C10 1.395(13) . ? C10 C11 1.389(13) . ? C11 C12 1.373(12) . ? C12 S2 1.782(9) . ? S2 C13 1.776(9) . ? C13 C14 1.359(12) . ? C13 C18 1.396(13) . ? C14 C15 1.351(13) . ? C15 C16 1.355(15) . ? C16 C17 1.368(14) . ? C17 C18 1.390(13) . ? S3 N2 1.589(8) . ? S3 C19 1.783(9) . ? S3 C25 1.794(9) . ? C19 C20 1.403(12) . ? C19 C24 1.404(12) . ? C20 C21 1.392(12) . ? C21 C22 1.398(14) . ? C22 C23 1.353(13) . ? C23 C24 1.370(12) . ? C25 C30 1.405(12) . ? C25 C26 1.406(12) . ? C26 C27 1.379(12) . ? C27 C28 1.384(12) . ? C28 C29 1.403(13) . ? C29 C30 1.381(12) . ? C30 S4 1.779(9) . ? S4 C31 1.785(9) . ? C31 C32 1.377(12) . ? C31 C36 1.407(12) . ? C32 C33 1.367(12) . ? C33 C34 1.365(13) . ? C34 C35 1.370(14) . ? C35 C36 1.389(13) . ? 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 C1 109.8(4) . . ? N1 S1 C7 110.3(4) . . ? C1 S1 C7 98.6(4) . . ? C2 C1 C6 120.4(8) . . ? C2 C1 S1 123.4(7) . . ? C6 C1 S1 116.1(7) . . ? C1 C2 C3 119.2(9) . . ? C2 C3 C4 121.0(9) . . ? C5 C4 C3 119.5(9) . . ? C4 C5 C6 119.2(9) . . ? C5 C6 C1 120.7(9) . . ? C8 C7 C12 119.4(8) . . ? C8 C7 S1 118.9(7) . . ? C12 C7 S1 121.4(7) . . ? C7 C8 C9 121.7(9) . . ? C8 C9 C10 118.5(9) . . ? C11 C10 C9 120.2(9) . . ? C12 C11 C10 120.6(9) . . ? C11 C12 C7 119.5(8) . . ? C11 C12 S2 122.9(7) . . ? C7 C12 S2 117.5(6) . . ? C13 S2 C12 105.7(4) . . ? C14 C13 C18 119.1(9) . . ? C14 C13 S2 121.0(7) . . ? C18 C13 S2 119.6(7) . . ? C15 C14 C13 121.2(10) . . ? C14 C15 C16 120.9(10) . . ? C15 C16 C17 120.0(10) . . ? C16 C17 C18 119.9(10) . . ? C17 C18 C13 119.0(9) . . ? N2 S3 C19 108.4(4) . . ? N2 S3 C25 111.2(4) . . ? C19 S3 C25 99.9(4) . . ? C20 C19 C24 118.5(8) . . ? C20 C19 S3 115.9(7) . . ? C24 C19 S3 125.5(7) . . ? C21 C20 C19 120.1(9) . . ? C20 C21 C22 119.7(9) . . ? C23 C22 C21 119.9(9) . . ? C22 C23 C24 121.8(10) . . ? C23 C24 C19 120.1(9) . . ? C30 C25 C26 119.3(8) . . ? C30 C25 S3 121.4(7) . . ? C26 C25 S3 119.2(7) . . ? C27 C26 C25 120.3(9) . . ? C26 C27 C28 120.3(9) . . ? C27 C28 C29 120.0(9) . . ? C30 C29 C28 120.2(8) . . ? C29 C30 C25 119.9(9) . . ? C29 C30 S4 119.9(7) . . ? C25 C30 S4 120.2(7) . . ? C30 S4 C31 100.7(4) . . ? C32 C31 C36 119.3(8) . . ? C32 C31 S4 122.5(7) . . ? C36 C31 S4 117.9(7) . . ? C33 C32 C31 120.7(9) . . ? C34 C33 C32 120.5(10) . . ? C33 C34 C35 120.0(9) . . ? C34 C35 C36 120.8(10) . . ? C35 C36 C31 118.5(9) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A N1 0.91(9) 2.32(9) 3.205(7) 164(8) 4_576 N2 H2A N2 0.97(10) 2.17(10) 3.139(7) 172(8) 4_566 O1 H1B N1 0.88(7) 2.00(7) 2.866(10) 168(10) . O1 H1C O1 0.88(7) 2.28(9) 2.977(5) 136(9) 4_576 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 22.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.835 _refine_diff_density_min -0.667 _refine_diff_density_rms 0.173 #===END data_3a _database_code_CSD 157265 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H13 N O S' _chemical_formula_weight 219.29 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' 'S' 'S' 0.1246 0.1234 '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca 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 5.1467(4) _cell_length_b 20.1417(14) _cell_length_c 21.4008(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2218.5(3) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7134 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 28.65 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 1.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.313 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 0.263 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.757 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1K CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 17699 _diffrn_reflns_av_R_equivalents 0.0252 _diffrn_reflns_av_sigmaI/netI 0.0198 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 28.92 _reflns_number_total 2712 _reflns_number_gt 2111 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0472P)^2^+0.6806P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary 'all non-H atoms found by direct methods' _atom_sites_solution_hydrogens 'geom except NH & OH coords freely refined' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2712 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0455 _refine_ls_R_factor_gt 0.0321 _refine_ls_wR_factor_ref 0.0898 _refine_ls_wR_factor_gt 0.0822 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 N1 N 0.5037(2) 0.12427(6) 0.70998(6) 0.0249(3) Uani 1 1 d . . . H1 H 0.366(4) 0.1203(9) 0.7265(8) 0.037 Uiso 1 1 d . . . S1 S 0.50213(6) 0.089892(15) 0.643786(15) 0.02124(11) Uani 1 1 d . . . C1 C 0.4075(3) 0.00420(6) 0.64852(6) 0.0208(3) Uani 1 1 d . . . C2 C 0.5642(3) -0.04102(7) 0.61761(7) 0.0269(3) Uani 1 1 d . . . H2 H 0.7096 -0.0262 0.5941 0.032 Uiso 1 1 calc R . . C3 C 0.5067(3) -0.10861(7) 0.62122(8) 0.0329(3) Uani 1 1 d . . . H3 H 0.6128 -0.1400 0.6001 0.040 Uiso 1 1 calc R . . C4 C 0.2960(3) -0.12979(7) 0.65547(7) 0.0301(3) Uani 1 1 d . . . H4 H 0.2567 -0.1758 0.6578 0.036 Uiso 1 1 calc R . . C5 C 0.1410(3) -0.08429(7) 0.68666(7) 0.0299(3) Uani 1 1 d . . . H5 H -0.0037 -0.0993 0.7103 0.036 Uiso 1 1 calc R . . C6 C 0.1958(3) -0.01678(7) 0.68359(6) 0.0272(3) Uani 1 1 d . . . H6 H 0.0903 0.0144 0.7051 0.033 Uiso 1 1 calc R . . C7 C 0.2321(3) 0.11995(6) 0.59760(6) 0.0230(3) Uani 1 1 d . . . C8 C 0.1734(3) 0.08985(8) 0.54076(7) 0.0331(3) Uani 1 1 d . . . H8 H 0.2640 0.0511 0.5279 0.040 Uiso 1 1 calc R . . C9 C -0.0185(3) 0.11697(9) 0.50319(7) 0.0384(4) Uani 1 1 d . . . H9 H -0.0599 0.0968 0.4643 0.046 Uiso 1 1 calc R . . C10 C -0.1506(3) 0.17357(8) 0.52219(7) 0.0344(4) Uani 1 1 d . . . H10 H -0.2808 0.1923 0.4961 0.041 Uiso 1 1 calc R . . C11 C -0.0927(3) 0.20257(7) 0.57894(7) 0.0320(3) Uani 1 1 d . . . H11 H -0.1852 0.2409 0.5921 0.038 Uiso 1 1 calc R . . C12 C 0.1000(3) 0.17606(6) 0.61707(7) 0.0269(3) Uani 1 1 d . . . H12 H 0.1404 0.1962 0.6560 0.032 Uiso 1 1 calc R . . O1 O 0.6274(2) 0.26185(5) 0.71925(5) 0.0316(2) Uani 1 1 d . . . H1B H 0.612(4) 0.2221(11) 0.7140(9) 0.047 Uiso 1 1 d . . . H1A H 0.776(4) 0.2659(9) 0.7376(9) 0.047 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 N1 0.0249(6) 0.0243(6) 0.0255(6) -0.0040(4) -0.0019(5) -0.0029(5) S1 0.02040(18) 0.01987(17) 0.02344(18) -0.00033(11) -0.00009(12) -0.00166(12) C1 0.0222(6) 0.0192(6) 0.0211(6) 0.0003(5) -0.0033(5) -0.0016(5) C2 0.0252(7) 0.0259(7) 0.0296(7) -0.0004(5) 0.0034(6) 0.0001(6) C3 0.0369(9) 0.0241(7) 0.0379(8) -0.0038(6) 0.0007(7) 0.0042(6) C4 0.0389(9) 0.0209(6) 0.0306(7) 0.0035(5) -0.0082(6) -0.0037(6) C5 0.0307(8) 0.0316(7) 0.0275(7) 0.0056(6) 0.0004(6) -0.0072(6) C6 0.0282(7) 0.0260(7) 0.0274(7) -0.0005(5) 0.0037(6) 0.0004(6) C7 0.0231(7) 0.0231(6) 0.0228(6) 0.0043(5) 0.0009(5) -0.0016(5) C8 0.0341(8) 0.0399(8) 0.0253(7) -0.0034(6) -0.0006(6) 0.0093(7) C9 0.0397(9) 0.0525(10) 0.0230(7) 0.0002(7) -0.0039(6) 0.0084(8) C10 0.0308(8) 0.0390(8) 0.0335(8) 0.0139(6) -0.0024(6) 0.0027(6) C11 0.0304(7) 0.0204(6) 0.0451(9) 0.0066(6) 0.0003(7) 0.0003(6) C12 0.0296(8) 0.0196(6) 0.0314(7) 0.0009(5) -0.0011(6) -0.0037(6) O1 0.0295(6) 0.0218(5) 0.0435(6) -0.0026(4) -0.0034(5) 0.0013(4) _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 N1 S1 1.5767(12) . ? S1 C1 1.7961(13) . ? S1 C7 1.8096(14) . ? C1 C2 1.3847(19) . ? C1 C6 1.389(2) . ? C2 C3 1.395(2) . ? C3 C4 1.376(2) . ? C4 C5 1.386(2) . ? C5 C6 1.390(2) . ? C7 C12 1.3832(19) . ? C7 C8 1.392(2) . ? C8 C9 1.386(2) . ? C9 C10 1.388(2) . ? C10 C11 1.380(2) . ? C11 C12 1.391(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 C1 111.88(6) . . ? N1 S1 C7 110.34(6) . . ? C1 S1 C7 98.29(6) . . ? C2 C1 C6 120.97(12) . . ? C2 C1 S1 116.58(11) . . ? C6 C1 S1 122.38(10) . . ? C1 C2 C3 119.47(14) . . ? C4 C3 C2 119.93(14) . . ? C3 C4 C5 120.31(13) . . ? C4 C5 C6 120.48(14) . . ? C1 C6 C5 118.83(13) . . ? C12 C7 C8 120.81(13) . . ? C12 C7 S1 119.10(10) . . ? C8 C7 S1 119.89(11) . . ? C9 C8 C7 119.34(14) . . ? C8 C9 C10 120.19(15) . . ? C11 C10 C9 119.97(14) . . ? C10 C11 C12 120.52(14) . . ? C7 C12 C11 119.17(13) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 N1 0.80(2) 2.309(19) 3.0914(13) 167.6(17) 6_557 O1 H1B N1 0.81(2) 2.05(2) 2.8502(16) 168.4(19) . O1 H1A O1 0.87(2) 2.03(2) 2.8904(10) 172.3(18) 6_657 _diffrn_measured_fraction_theta_max 0.930 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.376 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.046 #===END data_3b _database_code_CSD 162727 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H11 N S' _chemical_formula_weight 201.28 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' '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 5.6702(4) _cell_length_b 8.9745(6) _cell_length_c 40.530(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.970(2) _cell_angle_gamma 90.00 _cell_volume 2062.2(2) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8920 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 28.71 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.76 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.297 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.270 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.821 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 16687 _diffrn_reflns_av_R_equivalents 0.0257 _diffrn_reflns_av_sigmaI/netI 0.0262 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -52 _diffrn_reflns_limit_l_max 51 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 28.71 _reflns_number_total 4872 _reflns_number_gt 4159 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0192P)^2^+1.8910P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geom except NH coords freely refined' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4872 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0581 _refine_ls_R_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.0973 _refine_ls_wR_factor_gt 0.0940 _refine_ls_goodness_of_fit_ref 1.167 _refine_ls_restrained_S_all 1.167 _refine_ls_shift/su_max 0.000 _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 N1 N 0.4157(4) 0.4947(2) 0.16010(5) 0.0321(4) Uani 1 1 d . . . H1A H 0.272(5) 0.502(3) 0.1580(7) 0.048 Uiso 1 1 d . . . S1 S 0.49362(9) 0.35550(6) 0.181224(12) 0.02646(12) Uani 1 1 d . . . C1 C 0.3444(3) 0.3457(2) 0.22028(5) 0.0263(4) Uani 1 1 d . . . C2 C 0.1452(4) 0.4296(3) 0.22591(6) 0.0342(5) Uani 1 1 d . . . H2 H 0.0868 0.4965 0.2096 0.041 Uiso 1 1 calc R . . C3 C 0.0309(4) 0.4148(3) 0.25589(6) 0.0411(6) Uani 1 1 d . . . H3 H -0.1061 0.4723 0.2601 0.049 Uiso 1 1 calc R . . C4 C 0.1159(5) 0.3169(3) 0.27955(6) 0.0411(6) Uani 1 1 d . . . H4 H 0.0354 0.3061 0.2998 0.049 Uiso 1 1 calc R . . C5 C 0.3172(5) 0.2345(3) 0.27395(5) 0.0395(6) Uani 1 1 d . . . H5 H 0.3757 0.1678 0.2904 0.047 Uiso 1 1 calc R . . C6 C 0.4336(4) 0.2493(2) 0.24433(5) 0.0326(5) Uani 1 1 d . . . H6 H 0.5733 0.1940 0.2405 0.039 Uiso 1 1 calc R . . C7 C 0.3693(3) 0.1832(2) 0.16557(4) 0.0238(4) Uani 1 1 d . . . C8 C 0.4912(4) 0.0519(2) 0.17111(5) 0.0314(5) Uani 1 1 d . . . H8 H 0.6398 0.0533 0.1823 0.038 Uiso 1 1 calc R . . C9 C 0.3949(5) -0.0823(3) 0.16024(5) 0.0374(5) Uani 1 1 d . . . H9 H 0.4772 -0.1730 0.1641 0.045 Uiso 1 1 calc R . . C10 C 0.1795(4) -0.0834(3) 0.14379(5) 0.0343(5) Uani 1 1 d . . . H10 H 0.1126 -0.1751 0.1366 0.041 Uiso 1 1 calc R . . C11 C 0.0612(4) 0.0487(3) 0.13785(5) 0.0342(5) Uani 1 1 d . . . H11 H -0.0858 0.0472 0.1263 0.041 Uiso 1 1 calc R . . C12 C 0.1543(4) 0.1840(2) 0.14860(5) 0.0296(4) Uani 1 1 d . . . H12 H 0.0728 0.2748 0.1444 0.035 Uiso 1 1 calc R . . N2 N 0.8929(3) 0.5709(2) 0.12903(4) 0.0311(4) Uani 1 1 d . . . H2A H 0.747(5) 0.557(3) 0.1341(6) 0.047 Uiso 1 1 d . . . S2 S 0.92893(9) 0.54884(6) 0.091096(13) 0.02644(12) Uani 1 1 d . . . C13 C 0.6967(3) 0.6389(2) 0.06693(5) 0.0245(4) Uani 1 1 d . . . C14 C 0.6987(4) 0.6321(2) 0.03266(5) 0.0340(5) Uani 1 1 d . . . H14 H 0.8202 0.5794 0.0218 0.041 Uiso 1 1 calc R . . C15 C 0.5220(4) 0.7028(3) 0.01449(5) 0.0364(5) Uani 1 1 d . . . H15 H 0.5210 0.6978 -0.0089 0.044 Uiso 1 1 calc R . . C16 C 0.3463(4) 0.7811(2) 0.03057(5) 0.0312(5) Uani 1 1 d . . . H16 H 0.2252 0.8294 0.0181 0.037 Uiso 1 1 calc R . . C17 C 0.3476(4) 0.7890(2) 0.06461(5) 0.0285(4) Uani 1 1 d . . . H17 H 0.2279 0.8432 0.0755 0.034 Uiso 1 1 calc R . . C18 C 0.5240(4) 0.7177(2) 0.08303(5) 0.0259(4) Uani 1 1 d . . . H18 H 0.5253 0.7232 0.1064 0.031 Uiso 1 1 calc R . . C19 C 0.8597(3) 0.3622(2) 0.07704(5) 0.0237(4) Uani 1 1 d . . . C20 C 0.6561(3) 0.2897(2) 0.08662(5) 0.0264(4) Uani 1 1 d . . . H20 H 0.5457 0.3384 0.1003 0.032 Uiso 1 1 calc R . . C21 C 0.6158(4) 0.1444(2) 0.07586(5) 0.0299(4) Uani 1 1 d . . . H21 H 0.4773 0.0932 0.0823 0.036 Uiso 1 1 calc R . . C22 C 0.7777(4) 0.0742(2) 0.05572(5) 0.0321(5) Uani 1 1 d . . . H22 H 0.7486 -0.0246 0.0483 0.039 Uiso 1 1 calc R . . C23 C 0.9809(4) 0.1474(2) 0.04648(5) 0.0325(5) Uani 1 1 d . . . H23 H 1.0914 0.0988 0.0328 0.039 Uiso 1 1 calc R . . C24 C 1.0232(4) 0.2926(2) 0.05726(5) 0.0287(4) Uani 1 1 d . . . H24 H 1.1628 0.3433 0.0511 0.034 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 N1 0.0339(10) 0.0261(9) 0.0363(10) 0.0049(8) -0.0009(8) -0.0026(8) S1 0.0248(2) 0.0260(2) 0.0285(2) 0.0011(2) -0.00070(19) -0.0019(2) C1 0.0276(10) 0.0261(10) 0.0252(9) -0.0034(8) -0.0038(8) -0.0051(8) C2 0.0332(12) 0.0330(12) 0.0363(12) -0.0026(9) -0.0042(9) 0.0036(9) C3 0.0363(13) 0.0460(14) 0.0411(13) -0.0110(11) 0.0062(10) 0.0010(11) C4 0.0534(15) 0.0411(13) 0.0292(11) -0.0102(10) 0.0091(10) -0.0120(11) C5 0.0604(16) 0.0306(12) 0.0273(11) -0.0019(9) -0.0052(10) -0.0017(11) C6 0.0383(12) 0.0301(11) 0.0292(11) -0.0038(9) -0.0064(9) 0.0026(9) C7 0.0267(10) 0.0259(10) 0.0188(9) -0.0002(7) 0.0033(7) -0.0017(8) C8 0.0350(11) 0.0328(11) 0.0262(10) -0.0026(9) -0.0035(8) 0.0071(9) C9 0.0570(15) 0.0282(11) 0.0269(11) -0.0016(9) -0.0009(10) 0.0073(10) C10 0.0495(14) 0.0319(12) 0.0217(10) -0.0032(8) 0.0051(9) -0.0098(10) C11 0.0319(11) 0.0435(13) 0.0273(10) -0.0035(10) -0.0013(8) -0.0055(10) C12 0.0321(11) 0.0301(11) 0.0264(10) 0.0005(8) -0.0023(8) 0.0029(9) N2 0.0324(10) 0.0284(9) 0.0322(9) -0.0004(7) -0.0091(8) -0.0053(8) S2 0.0231(2) 0.0221(2) 0.0341(3) 0.0018(2) -0.00159(19) -0.00507(19) C13 0.0275(10) 0.0175(9) 0.0284(10) 0.0034(8) 0.0006(8) -0.0032(8) C14 0.0428(13) 0.0283(11) 0.0310(11) -0.0008(9) 0.0067(9) 0.0063(10) C15 0.0512(14) 0.0342(12) 0.0235(10) -0.0006(9) -0.0018(9) 0.0053(10) C16 0.0343(12) 0.0253(10) 0.0337(11) 0.0027(9) -0.0066(9) -0.0001(9) C17 0.0292(11) 0.0229(10) 0.0336(11) 0.0019(8) 0.0045(8) -0.0011(8) C18 0.0329(11) 0.0200(9) 0.0248(9) 0.0012(8) 0.0018(8) -0.0031(8) C19 0.0240(10) 0.0204(9) 0.0265(9) 0.0027(8) -0.0028(7) 0.0005(8) C20 0.0246(10) 0.0244(10) 0.0301(10) 0.0005(8) 0.0006(8) 0.0003(8) C21 0.0288(11) 0.0258(10) 0.0350(11) 0.0030(9) -0.0034(8) -0.0027(9) C22 0.0405(12) 0.0230(10) 0.0325(11) -0.0012(8) -0.0072(9) 0.0032(9) C23 0.0357(12) 0.0313(11) 0.0305(11) -0.0009(9) 0.0005(9) 0.0093(9) C24 0.0230(10) 0.0305(11) 0.0326(11) 0.0043(9) 0.0015(8) 0.0019(8) _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 N1 S1 1.5735(19) . ? S1 C1 1.810(2) . ? S1 C7 1.810(2) . ? C1 C2 1.379(3) . ? C1 C6 1.392(3) . ? C2 C3 1.393(3) . ? C3 C4 1.382(4) . ? C4 C5 1.382(4) . ? C5 C6 1.386(3) . ? C7 C8 1.383(3) . ? C7 C12 1.390(3) . ? C8 C9 1.391(3) . ? C9 C10 1.382(3) . ? C10 C11 1.382(3) . ? C11 C12 1.391(3) . ? N2 S2 1.5670(19) . ? S2 C19 1.810(2) . ? S2 C13 1.817(2) . ? C13 C18 1.381(3) . ? C13 C14 1.391(3) . ? C14 C15 1.387(3) . ? C15 C16 1.390(3) . ? C16 C17 1.381(3) . ? C17 C18 1.393(3) . ? C19 C24 1.385(3) . ? C19 C20 1.387(3) . ? C20 C21 1.392(3) . ? C21 C22 1.390(3) . ? C22 C23 1.384(3) . ? C23 C24 1.394(3) . ? 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 C1 112.54(10) . . ? N1 S1 C7 112.56(10) . . ? C1 S1 C7 94.60(9) . . ? C2 C1 C6 120.8(2) . . ? C2 C1 S1 120.97(16) . . ? C6 C1 S1 118.22(16) . . ? C1 C2 C3 119.1(2) . . ? C4 C3 C2 120.3(2) . . ? C3 C4 C5 120.4(2) . . ? C4 C5 C6 119.8(2) . . ? C5 C6 C1 119.6(2) . . ? C8 C7 C12 121.10(19) . . ? C8 C7 S1 118.74(15) . . ? C12 C7 S1 120.16(16) . . ? C7 C8 C9 119.6(2) . . ? C10 C9 C8 119.9(2) . . ? C11 C10 C9 120.0(2) . . ? C10 C11 C12 120.9(2) . . ? C7 C12 C11 118.4(2) . . ? N2 S2 C19 113.25(9) . . ? N2 S2 C13 111.54(10) . . ? C19 S2 C13 95.21(9) . . ? C18 C13 C14 120.82(19) . . ? C18 C13 S2 119.11(15) . . ? C14 C13 S2 120.04(16) . . ? C15 C14 C13 119.5(2) . . ? C14 C15 C16 119.9(2) . . ? C17 C16 C15 120.2(2) . . ? C16 C17 C18 120.2(2) . . ? C13 C18 C17 119.38(18) . . ? C24 C19 C20 121.28(19) . . ? C24 C19 S2 117.13(15) . . ? C20 C19 S2 121.55(15) . . ? C19 C20 C21 118.98(19) . . ? C22 C21 C20 120.2(2) . . ? C23 C22 C21 120.3(2) . . ? C22 C23 C24 119.9(2) . . ? C19 C24 C23 119.31(19) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A N2 0.82(3) 2.51(3) 3.274(3) 156(3) 1_455 N2 H2A N1 0.86(3) 2.24(3) 3.080(3) 164(2) . _diffrn_measured_fraction_theta_max 0.912 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.415 _refine_diff_density_min -0.340 _refine_diff_density_rms 0.052 #===END