data_b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H16 Cl2 N2 O2 S' _chemical_formula_weight 443.33 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)/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 14.923(3) _cell_length_b 14.369(3) _cell_length_c 9.6105(19) _cell_angle_alpha 90.00 _cell_angle_beta 93.77(3) _cell_angle_gamma 90.00 _cell_volume 2056.3(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 13907 _cell_measurement_theta_min 1.37 _cell_measurement_theta_max 27.48 _exptl_crystal_description 'Thin Platelet' _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.69 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.432 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.439 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.7523 _exptl_absorpt_correction_T_max 0.9861 _exptl_absorpt_process_details Abscor _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Raxis Rapid IP Area Detector' _diffrn_measurement_method '\w Oscillation' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13907 _diffrn_reflns_av_R_equivalents 0.0655 _diffrn_reflns_av_sigmaI/netI 0.0994 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.37 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4650 _reflns_number_gt 1613 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid Auto(Rigaku 2001)' _computing_cell_refinement 'Rapid Auto(Rigaku 2001)' _computing_data_reduction 'Rapid Auto(Rigaku 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0710P)^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 _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4650 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1850 _refine_ls_R_factor_gt 0.0677 _refine_ls_wR_factor_ref 0.1956 _refine_ls_wR_factor_gt 0.1550 _refine_ls_goodness_of_fit_ref 0.973 _refine_ls_restrained_S_all 0.973 _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 Cl1 Cl 0.48679(8) 0.64238(10) 0.52093(16) 0.1153(5) Uani 1 1 d . . . Cl2 Cl 0.58371(11) 0.51187(12) -0.19346(17) 0.1427(7) Uani 1 1 d . . . S1 S 0.79648(7) 0.54278(9) 0.28080(14) 0.0914(4) Uani 1 1 d . . . O1 O 0.8766(2) 0.6496(2) 0.4985(4) 0.1106(12) Uani 1 1 d . . . H1A H 0.9008 0.6818 0.5606 0.166 Uiso 1 1 calc R . . O2 O 0.7093(2) 0.3547(2) 0.3451(4) 0.1046(11) Uani 1 1 d . . . H2A H 0.7450 0.3885 0.3896 0.157 Uiso 1 1 calc R . . N1 N 0.8155(3) 0.4017(3) 0.5730(5) 0.1076(14) Uani 1 1 d . . . N2 N 1.0399(3) 0.3431(3) 1.2413(5) 0.0958(12) Uani 1 1 d . . . C1 C 0.6024(3) 0.6484(3) 0.5099(6) 0.0893(14) Uani 1 1 d . . . C2 C 0.6512(4) 0.7029(4) 0.6068(6) 0.1079(17) Uani 1 1 d . . . H2B H 0.6224 0.7373 0.6726 0.129 Uiso 1 1 calc R . . C3 C 0.7435(4) 0.7049(4) 0.6034(6) 0.1060(17) Uani 1 1 d . . . H3A H 0.7776 0.7407 0.6678 0.127 Uiso 1 1 calc R . . C4 C 0.7851(3) 0.6539(3) 0.5049(6) 0.0947(15) Uani 1 1 d . . . C5 C 0.7343(3) 0.6021(3) 0.4053(5) 0.0826(13) Uani 1 1 d . . . C6 C 0.6422(3) 0.6013(3) 0.4089(5) 0.0836(13) Uani 1 1 d . . . H6A H 0.6073 0.5683 0.3419 0.100 Uiso 1 1 calc R . . C7 C 0.7123(3) 0.4818(3) 0.1804(5) 0.0794(13) Uani 1 1 d . . . C8 C 0.6805(3) 0.5181(3) 0.0513(5) 0.0911(14) Uani 1 1 d . . . H8A H 0.6997 0.5763 0.0231 0.109 Uiso 1 1 calc R . . C9 C 0.6215(3) 0.4681(4) -0.0329(6) 0.0976(15) Uani 1 1 d . . . C10 C 0.5918(3) 0.3831(4) 0.0093(6) 0.1086(18) Uani 1 1 d . . . H10A H 0.5511 0.3496 -0.0486 0.130 Uiso 1 1 calc R . . C11 C 0.6211(3) 0.3472(3) 0.1347(6) 0.1017(16) Uani 1 1 d . . . H11A H 0.6002 0.2895 0.1623 0.122 Uiso 1 1 calc R . . C12 C 0.6826(3) 0.3964(3) 0.2231(5) 0.0837(13) Uani 1 1 d . . . C13 C 0.9011(3) 0.4199(4) 0.5958(6) 0.1081(17) Uani 1 1 d . . . H13A H 0.9326 0.4407 0.5215 0.130 Uiso 1 1 calc R . . C14 C 0.9468(3) 0.4099(3) 0.7237(6) 0.0986(16) Uani 1 1 d . . . H14A H 1.0078 0.4233 0.7332 0.118 Uiso 1 1 calc R . . C15 C 0.9034(3) 0.3802(3) 0.8384(6) 0.0811(13) Uani 1 1 d . . . C16 C 0.8126(3) 0.3616(4) 0.8150(6) 0.1083(18) Uani 1 1 d . . . H16A H 0.7790 0.3416 0.8874 0.130 Uiso 1 1 calc R . . C17 C 0.7729(3) 0.3733(5) 0.6821(7) 0.120(2) Uani 1 1 d . . . H17A H 0.7119 0.3604 0.6683 0.144 Uiso 1 1 calc R . . C18 C 0.9500(3) 0.3674(3) 0.9778(5) 0.0768(12) Uani 1 1 d . . . C19 C 1.0424(3) 0.3730(4) 0.9973(6) 0.1038(16) Uani 1 1 d . . . H19A H 1.0766 0.3849 0.9217 0.125 Uiso 1 1 calc R . . C20 C 1.0841(4) 0.3610(4) 1.1275(7) 0.1142(18) Uani 1 1 d . . . H20A H 1.1463 0.3657 1.1373 0.137 Uiso 1 1 calc R . . C21 C 0.9510(3) 0.3360(3) 1.2207(6) 0.0994(16) Uani 1 1 d . . . H21A H 0.9182 0.3219 1.2970 0.119 Uiso 1 1 calc R . . C22 C 0.9051(3) 0.3483(3) 1.0940(6) 0.0971(15) Uani 1 1 d . . . H22A H 0.8428 0.3436 1.0869 0.116 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 Cl1 0.0862(9) 0.1309(11) 0.1259(12) -0.0074(9) -0.0149(7) 0.0310(7) Cl2 0.1484(13) 0.1706(15) 0.1027(12) 0.0033(11) -0.0394(10) 0.0216(11) S1 0.0727(7) 0.0999(9) 0.0994(9) -0.0078(8) -0.0116(6) -0.0130(6) O1 0.094(2) 0.117(3) 0.117(3) -0.014(2) -0.020(2) -0.0246(19) O2 0.091(2) 0.101(2) 0.117(3) 0.009(2) -0.029(2) -0.0106(17) N1 0.082(3) 0.118(3) 0.119(4) 0.019(3) -0.025(3) -0.010(2) N2 0.091(3) 0.095(3) 0.099(4) -0.004(3) -0.012(3) -0.007(2) C1 0.083(3) 0.088(3) 0.094(4) -0.004(3) -0.014(3) 0.016(3) C2 0.106(4) 0.099(4) 0.115(5) -0.014(3) -0.019(3) 0.032(3) C3 0.121(5) 0.089(4) 0.105(4) -0.018(3) -0.019(3) 0.011(3) C4 0.086(3) 0.083(3) 0.111(4) 0.007(3) -0.029(3) -0.006(3) C5 0.088(3) 0.073(3) 0.084(3) 0.002(3) -0.017(3) -0.010(2) C6 0.082(3) 0.086(3) 0.080(3) -0.004(3) -0.017(3) 0.004(2) C7 0.062(3) 0.086(3) 0.089(4) -0.011(3) -0.007(2) 0.001(2) C8 0.083(3) 0.098(3) 0.090(4) -0.002(3) -0.008(3) 0.010(3) C9 0.086(3) 0.113(4) 0.091(4) -0.015(3) -0.016(3) 0.015(3) C10 0.092(4) 0.116(4) 0.112(5) -0.026(4) -0.032(3) -0.002(3) C11 0.083(3) 0.100(4) 0.118(5) -0.012(3) -0.026(3) -0.009(3) C12 0.061(3) 0.090(3) 0.098(4) -0.004(3) -0.011(2) 0.002(2) C13 0.082(3) 0.140(5) 0.099(4) 0.016(3) -0.015(3) -0.025(3) C14 0.074(3) 0.108(4) 0.110(4) 0.013(3) -0.015(3) -0.018(3) C15 0.067(3) 0.081(3) 0.094(4) -0.004(3) -0.006(3) 0.004(2) C16 0.070(3) 0.140(5) 0.111(5) 0.012(4) -0.015(3) 0.002(3) C17 0.065(3) 0.166(6) 0.126(5) 0.005(5) -0.021(3) -0.003(3) C18 0.072(3) 0.068(3) 0.089(4) -0.001(3) -0.006(3) -0.002(2) C19 0.074(3) 0.138(5) 0.096(4) 0.006(3) -0.013(3) -0.001(3) C20 0.084(4) 0.146(5) 0.111(5) -0.002(4) -0.012(4) -0.010(3) C21 0.093(4) 0.097(4) 0.108(5) 0.012(3) 0.005(3) -0.014(3) C22 0.071(3) 0.112(4) 0.106(4) 0.013(3) -0.006(3) -0.003(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 Cl1 C1 1.737(5) . ? Cl2 C9 1.727(6) . ? S1 C7 1.765(4) . ? S1 C5 1.779(5) . ? O1 C4 1.373(6) . ? O2 C12 1.354(6) . ? N1 C13 1.307(5) . ? N1 C17 1.326(7) . ? N2 C21 1.332(5) . ? N2 C20 1.339(6) . ? C1 C6 1.353(6) . ? C1 C2 1.386(7) . ? C2 C3 1.380(7) . ? C3 C4 1.377(7) . ? C4 C5 1.396(6) . ? C5 C6 1.378(6) . ? C7 C12 1.377(6) . ? C7 C8 1.399(6) . ? C8 C9 1.362(7) . ? C9 C10 1.370(7) . ? C10 C11 1.357(7) . ? C11 C12 1.400(6) . ? C13 C14 1.373(7) . ? C14 C15 1.382(6) . ? C15 C16 1.384(6) . ? C15 C18 1.480(6) . ? C16 C17 1.382(8) . ? C18 C22 1.368(6) . ? C18 C19 1.381(6) . ? C19 C20 1.371(7) . ? C21 C22 1.369(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 C7 S1 C5 102.8(2) . . ? C13 N1 C17 116.3(5) . . ? C21 N2 C20 115.6(5) . . ? C6 C1 C2 121.9(5) . . ? C6 C1 Cl1 120.2(4) . . ? C2 C1 Cl1 117.9(4) . . ? C3 C2 C1 118.5(5) . . ? C4 C3 C2 120.1(5) . . ? O1 C4 C3 123.4(5) . . ? O1 C4 C5 116.3(5) . . ? C3 C4 C5 120.4(5) . . ? C6 C5 C4 119.1(5) . . ? C6 C5 S1 125.3(4) . . ? C4 C5 S1 115.6(4) . . ? C1 C6 C5 120.0(4) . . ? C12 C7 C8 119.9(4) . . ? C12 C7 S1 120.7(4) . . ? C8 C7 S1 119.2(4) . . ? C9 C8 C7 119.9(5) . . ? C8 C9 C10 120.3(5) . . ? C8 C9 Cl2 120.0(5) . . ? C10 C9 Cl2 119.7(4) . . ? C11 C10 C9 120.6(5) . . ? C10 C11 C12 120.5(5) . . ? O2 C12 C7 124.8(4) . . ? O2 C12 C11 116.4(5) . . ? C7 C12 C11 118.7(5) . . ? N1 C13 C14 123.4(5) . . ? C13 C14 C15 121.0(5) . . ? C16 C15 C14 115.8(5) . . ? C16 C15 C18 121.3(5) . . ? C14 C15 C18 122.9(4) . . ? C17 C16 C15 118.8(5) . . ? N1 C17 C16 124.6(5) . . ? C22 C18 C19 116.0(5) . . ? C22 C18 C15 122.5(4) . . ? C19 C18 C15 121.4(5) . . ? C20 C19 C18 120.3(5) . . ? N2 C20 C19 123.5(5) . . ? N2 C21 C22 123.9(5) . . ? C21 C22 C18 120.6(5) . . ? 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 O1 H1A N2 0.82 2.08 2.721(5) 135.2 3_767 O2 H2A N1 0.82 2.00 2.704(5) 143.2 . O2 H2A S1 0.82 2.59 3.080(3) 119.8 . _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.257 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.047