data_ixk3s _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H18 N2 O3 S, C H Cl3' _chemical_formula_sum 'C15 H19 Cl3 N2 O3 S' _chemical_formula_weight 413.73 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' 'Cl' 'Cl' 0.1484 0.1585 '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 11.0349(17) _cell_length_b 10.4165(16) _cell_length_c 16.485(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.065(2) _cell_angle_gamma 90.00 _cell_volume 1838.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 108(2) _cell_measurement_reflns_used 7250 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 28.29 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.495 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 0.628 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.880 _exptl_absorpt_correction_T_max 0.949 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 108(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_reflns_number 13650 _diffrn_reflns_av_R_equivalents 0.0194 _diffrn_reflns_av_sigmaI/netI 0.0211 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 28.29 _reflns_number_total 4545 _reflns_number_gt 4188 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0608P)^2^+2.4155P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4545 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0568 _refine_ls_R_factor_gt 0.0529 _refine_ls_wR_factor_ref 0.1354 _refine_ls_wR_factor_gt 0.1328 _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_restrained_S_all 1.114 _refine_ls_shift/su_max 0.082 _refine_ls_shift/su_mean 0.008 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 Cl1 Cl 0.68703(6) 0.25476(7) 0.21071(5) 0.04040(18) Uani 1 1 d . . . C1 C 0.26556(19) 0.3999(2) 0.43395(13) 0.0191(4) Uani 1 1 d . . . C2 C 0.2007(2) 0.2942(2) 0.46903(14) 0.0248(5) Uani 1 1 d . . . H2A H 0.2379 0.2864 0.5298 0.030 Uiso 1 1 calc R . . H2B H 0.2138 0.2118 0.4425 0.030 Uiso 1 1 calc R . . C3 C 0.0597(2) 0.3193(3) 0.45429(18) 0.0381(6) Uani 1 1 d . . . H3A H 0.0165 0.2373 0.4589 0.046 Uiso 1 1 calc R . . H3B H 0.0450 0.3779 0.4982 0.046 Uiso 1 1 calc R . . C4 C 0.0046(2) 0.3784(3) 0.36874(18) 0.0397(7) Uani 1 1 d . . . H4 H -0.0877 0.3905 0.3592 0.048 Uiso 1 1 calc R . . C5 C 0.0698(2) 0.5059(3) 0.35975(16) 0.0312(5) Uani 1 1 d . . . H5A H 0.0256 0.5539 0.3094 0.037 Uiso 1 1 calc R . . H5B H 0.0782 0.5609 0.4098 0.037 Uiso 1 1 calc R . . C6 C 0.19608(19) 0.45574(19) 0.35132(13) 0.0183(4) Uani 1 1 d . . . H6 H 0.2457 0.5225 0.3300 0.022 Uiso 1 1 calc R . . C7 C 0.0364(2) 0.2961(3) 0.29842(16) 0.0352(6) Uani 1 1 d . . . H7A H 0.0410 0.2039 0.3134 0.042 Uiso 1 1 calc R . . H7B H -0.0268 0.3080 0.2450 0.042 Uiso 1 1 calc R . . C8 C 0.07560(19) 0.4688(2) 0.14395(13) 0.0180(4) Uani 1 1 d . . . C9 C -0.0376(2) 0.4248(2) 0.09482(13) 0.0221(4) Uani 1 1 d . . . H9 H -0.0524 0.3355 0.0860 0.026 Uiso 1 1 calc R . . C10 C -0.1285(2) 0.5135(2) 0.05891(14) 0.0242(4) Uani 1 1 d . . . H10 H -0.2057 0.4840 0.0247 0.029 Uiso 1 1 calc R . . C11 C -0.1094(2) 0.6450(2) 0.07182(14) 0.0223(4) Uani 1 1 d . . . C12 C 0.0061(2) 0.6866(2) 0.12026(14) 0.0223(4) Uani 1 1 d . . . H12 H 0.0213 0.7760 0.1286 0.027 Uiso 1 1 calc R . . C13 C 0.0987(2) 0.5999(2) 0.15627(13) 0.0208(4) Uani 1 1 d . . . H13 H 0.1769 0.6293 0.1889 0.025 Uiso 1 1 calc R . . C14 C -0.2107(2) 0.7392(2) 0.03442(17) 0.0317(5) Uani 1 1 d . . . H14A H -0.2498 0.7705 0.0780 0.048 Uiso 1 1 calc R . . H14B H -0.2737 0.6968 -0.0096 0.048 Uiso 1 1 calc R . . H14C H -0.1746 0.8116 0.0105 0.048 Uiso 1 1 calc R . . C15 C 0.5781(2) 0.3805(2) 0.20329(15) 0.0276(5) Uani 1 1 d . . . H15 H 0.4957 0.3415 0.2044 0.033 Uiso 1 1 calc R . . Cl2 Cl 0.62062(7) 0.48531(6) 0.28867(4) 0.03871(18) Uani 1 1 d . . . N1 N 0.37310(17) 0.44638(18) 0.46648(11) 0.0215(4) Uani 1 1 d . . . N2 N 0.16096(16) 0.34551(17) 0.29239(11) 0.0185(3) Uani 1 1 d . . . O1 O 0.42938(16) 0.38908(17) 0.54364(10) 0.0279(4) Uani 1 1 d . . . H1 H 0.5000 0.4221 0.5629 0.042 Uiso 1 1 calc R . . O2 O 0.15576(18) 0.23378(17) 0.16118(11) 0.0355(4) Uani 1 1 d . . . O3 O 0.30802(15) 0.4101(2) 0.20921(11) 0.0321(4) Uani 1 1 d . . . Cl3 Cl 0.55923(10) 0.46361(9) 0.10807(5) 0.0584(3) Uani 1 1 d . . . S1 S 0.18492(5) 0.35755(5) 0.19893(3) 0.02146(14) 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 Cl1 0.0261(3) 0.0354(4) 0.0600(4) -0.0089(3) 0.0111(3) 0.0052(2) C1 0.0229(9) 0.0153(9) 0.0193(9) -0.0016(7) 0.0056(8) 0.0018(8) C2 0.0262(10) 0.0248(11) 0.0245(11) 0.0057(9) 0.0079(8) -0.0004(9) C3 0.0296(12) 0.0518(17) 0.0369(14) 0.0135(13) 0.0158(11) 0.0040(12) C4 0.0181(10) 0.0613(19) 0.0407(15) 0.0216(13) 0.0094(10) 0.0045(11) C5 0.0314(12) 0.0335(13) 0.0314(12) 0.0054(10) 0.0128(10) 0.0177(10) C6 0.0221(9) 0.0134(9) 0.0193(9) -0.0020(7) 0.0049(7) 0.0006(7) C7 0.0291(12) 0.0428(15) 0.0301(12) 0.0077(11) 0.0003(9) -0.0190(11) C8 0.0190(9) 0.0183(10) 0.0167(9) -0.0001(7) 0.0041(7) 0.0048(8) C9 0.0252(10) 0.0178(10) 0.0214(10) -0.0040(8) 0.0020(8) -0.0008(8) C10 0.0214(10) 0.0244(11) 0.0238(10) -0.0004(8) 0.0000(8) -0.0004(8) C11 0.0258(10) 0.0213(11) 0.0212(10) 0.0037(8) 0.0084(8) 0.0033(8) C12 0.0296(11) 0.0155(10) 0.0240(10) 0.0001(8) 0.0107(8) -0.0025(8) C13 0.0203(9) 0.0224(10) 0.0204(10) -0.0012(8) 0.0064(8) -0.0040(8) C14 0.0340(12) 0.0263(12) 0.0333(13) 0.0052(10) 0.0052(10) 0.0088(10) C15 0.0230(10) 0.0294(12) 0.0324(12) -0.0038(10) 0.0106(9) 0.0010(9) Cl2 0.0468(4) 0.0280(3) 0.0383(4) -0.0051(3) 0.0044(3) -0.0008(3) N1 0.0273(9) 0.0179(9) 0.0172(8) -0.0017(7) 0.0012(7) 0.0011(7) N2 0.0194(8) 0.0162(8) 0.0184(8) -0.0019(6) 0.0018(6) -0.0021(6) O1 0.0318(8) 0.0267(8) 0.0204(8) 0.0040(6) -0.0032(6) -0.0017(7) O2 0.0469(11) 0.0246(9) 0.0284(9) -0.0101(7) -0.0038(8) 0.0152(8) O3 0.0188(7) 0.0487(11) 0.0305(9) -0.0011(8) 0.0095(6) 0.0064(7) Cl3 0.0808(6) 0.0646(6) 0.0364(4) 0.0087(4) 0.0269(4) 0.0212(5) S1 0.0207(2) 0.0225(3) 0.0201(3) -0.00409(19) 0.00283(19) 0.00723(19) _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 Cl1 C15 1.762(2) . ? C1 N1 1.273(3) . ? C1 C2 1.504(3) . ? C1 C6 1.508(3) . ? C2 C3 1.537(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.523(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.535(4) . ? C4 C7 1.549(4) . ? C4 H4 1.0000 . ? C5 C6 1.526(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 N2 1.493(3) . ? C6 H6 1.0000 . ? C7 N2 1.494(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.391(3) . ? C8 C13 1.395(3) . ? C8 S1 1.757(2) . ? C9 C10 1.386(3) . ? C9 H9 0.9500 . ? C10 C11 1.395(3) . ? C10 H10 0.9500 . ? C11 C12 1.398(3) . ? C11 C14 1.503(3) . ? C12 C13 1.385(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 Cl2 1.753(3) . ? C15 Cl3 1.760(3) . ? C15 H15 1.0000 . ? N1 O1 1.406(2) . ? N2 S1 1.6302(18) . ? O1 H1 0.8400 . ? O2 S1 1.4337(18) . ? O3 S1 1.4360(18) . ? 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 C1 C2 126.8(2) . . ? N1 C1 C6 116.83(19) . . ? C2 C1 C6 116.40(18) . . ? C1 C2 C3 111.9(2) . . ? C1 C2 H2A 109.2 . . ? C3 C2 H2A 109.2 . . ? C1 C2 H2B 109.2 . . ? C3 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? C4 C3 C2 112.1(2) . . ? C4 C3 H3A 109.2 . . ? C2 C3 H3A 109.2 . . ? C4 C3 H3B 109.2 . . ? C2 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? C3 C4 C5 110.4(2) . . ? C3 C4 C7 110.9(2) . . ? C5 C4 C7 102.1(2) . . ? C3 C4 H4 111.0 . . ? C5 C4 H4 111.0 . . ? C7 C4 H4 111.0 . . ? C6 C5 C4 99.91(19) . . ? C6 C5 H5A 111.8 . . ? C4 C5 H5A 111.8 . . ? C6 C5 H5B 111.8 . . ? C4 C5 H5B 111.8 . . ? H5A C5 H5B 109.5 . . ? N2 C6 C1 106.61(16) . . ? N2 C6 C5 102.96(18) . . ? C1 C6 C5 108.96(18) . . ? N2 C6 H6 112.6 . . ? C1 C6 H6 112.6 . . ? C5 C6 H6 112.6 . . ? N2 C7 C4 103.8(2) . . ? N2 C7 H7A 111.0 . . ? C4 C7 H7A 111.0 . . ? N2 C7 H7B 111.0 . . ? C4 C7 H7B 111.0 . . ? H7A C7 H7B 109.0 . . ? C9 C8 C13 120.89(19) . . ? C9 C8 S1 119.37(16) . . ? C13 C8 S1 119.47(16) . . ? C10 C9 C8 119.0(2) . . ? C10 C9 H9 120.5 . . ? C8 C9 H9 120.5 . . ? C9 C10 C11 121.5(2) . . ? C9 C10 H10 119.3 . . ? C11 C10 H10 119.3 . . ? C10 C11 C12 118.4(2) . . ? C10 C11 C14 120.6(2) . . ? C12 C11 C14 121.1(2) . . ? C13 C12 C11 121.2(2) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C12 C13 C8 119.10(19) . . ? C12 C13 H13 120.5 . . ? C8 C13 H13 120.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? Cl2 C15 Cl3 111.13(14) . . ? Cl2 C15 Cl1 111.25(13) . . ? Cl3 C15 Cl1 111.01(13) . . ? Cl2 C15 H15 107.8 . . ? Cl3 C15 H15 107.8 . . ? Cl1 C15 H15 107.8 . . ? C1 N1 O1 112.43(18) . . ? C6 N2 C7 108.62(18) . . ? C6 N2 S1 118.67(14) . . ? C7 N2 S1 116.91(15) . . ? N1 O1 H1 109.5 . . ? O2 S1 O3 120.02(12) . . ? O2 S1 N2 105.68(11) . . ? O3 S1 N2 106.49(10) . . ? O2 S1 C8 108.39(10) . . ? O3 S1 C8 108.70(11) . . ? N2 S1 C8 106.83(9) . . ? 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 N1 C1 C2 C3 141.6(2) . . . . ? C6 C1 C2 C3 -38.9(3) . . . . ? C1 C2 C3 C4 38.6(3) . . . . ? C2 C3 C4 C5 -58.9(3) . . . . ? C2 C3 C4 C7 53.5(3) . . . . ? C3 C4 C5 C6 72.2(3) . . . . ? C7 C4 C5 C6 -45.8(2) . . . . ? N1 C1 C6 N2 126.2(2) . . . . ? C2 C1 C6 N2 -53.3(2) . . . . ? N1 C1 C6 C5 -123.3(2) . . . . ? C2 C1 C6 C5 57.2(2) . . . . ? C4 C5 C6 N2 43.6(2) . . . . ? C4 C5 C6 C1 -69.3(2) . . . . ? C3 C4 C7 N2 -86.8(2) . . . . ? C5 C4 C7 N2 30.8(2) . . . . ? C13 C8 C9 C10 -0.9(3) . . . . ? S1 C8 C9 C10 173.15(17) . . . . ? C8 C9 C10 C11 -0.8(3) . . . . ? C9 C10 C11 C12 1.9(3) . . . . ? C9 C10 C11 C14 -178.1(2) . . . . ? C10 C11 C12 C13 -1.4(3) . . . . ? C14 C11 C12 C13 178.6(2) . . . . ? C11 C12 C13 C8 -0.2(3) . . . . ? C9 C8 C13 C12 1.4(3) . . . . ? S1 C8 C13 C12 -172.67(16) . . . . ? C2 C1 N1 O1 -1.2(3) . . . . ? C6 C1 N1 O1 179.33(17) . . . . ? C1 C6 N2 C7 89.4(2) . . . . ? C5 C6 N2 C7 -25.3(2) . . . . ? C1 C6 N2 S1 -133.87(15) . . . . ? C5 C6 N2 S1 111.51(17) . . . . ? C4 C7 N2 C6 -3.6(2) . . . . ? C4 C7 N2 S1 -141.21(17) . . . . ? C6 N2 S1 O2 173.69(15) . . . . ? C7 N2 S1 O2 -53.0(2) . . . . ? C6 N2 S1 O3 45.02(18) . . . . ? C7 N2 S1 O3 178.30(18) . . . . ? C6 N2 S1 C8 -71.02(17) . . . . ? C7 N2 S1 C8 62.27(19) . . . . ? C9 C8 S1 O2 19.8(2) . . . . ? C13 C8 S1 O2 -166.13(18) . . . . ? C9 C8 S1 O3 151.74(17) . . . . ? C13 C8 S1 O3 -34.1(2) . . . . ? C9 C8 S1 N2 -93.71(18) . . . . ? C13 C8 S1 N2 80.41(18) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.992 _refine_diff_density_min -0.553 _refine_diff_density_rms 0.079