data_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H18 Cl2 N2 O2 S' _chemical_formula_weight 469.36 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 9.7293(19) _cell_length_b 17.198(3) _cell_length_c 13.894(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.98(3) _cell_angle_gamma 90.00 _cell_volume 2245.8(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 20668 _cell_measurement_theta_min 1.92 _cell_measurement_theta_max 27.48 _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.78 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.388 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 0.406 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7414 _exptl_absorpt_correction_T_max 0.9207 _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 20668 _diffrn_reflns_av_R_equivalents 0.0410 _diffrn_reflns_av_sigmaI/netI 0.0390 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5132 _reflns_number_gt 3270 _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^)+(0.0689P)^2^+0.2100P] 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 5132 _refine_ls_number_parameters 267 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0792 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_ref 0.1413 _refine_ls_wR_factor_gt 0.1271 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 1.15599(11) 0.10284(5) 0.41608(5) 0.1074(3) Uani 1 1 d . . . Cl2 Cl 0.56952(7) 0.12962(5) 0.64497(7) 0.0959(3) Uani 1 1 d . . . S1 S 1.11947(6) 0.05093(3) 0.79852(4) 0.06531(18) Uani 1 1 d . . . O1 O 1.32160(17) -0.06566(9) 0.79509(13) 0.0769(5) Uani 1 1 d . . . H1A H 1.3811 -0.0993 0.7947 0.115 Uiso 1 1 calc R . . O2 O 1.16178(18) 0.23087(10) 0.79572(13) 0.0819(5) Uani 1 1 d . . . H2C H 1.2176 0.1944 0.8103 0.123 Uiso 1 1 calc R . . N1 N 0.4250(2) 0.32948(14) 0.36910(16) 0.0793(6) Uani 1 1 d . A . N2 N 1.4095(2) 0.37510(12) 0.66011(16) 0.0732(5) Uani 1 1 d . A . C1 C 1.2863(2) -0.02856(12) 0.70505(17) 0.0608(5) Uani 1 1 d . . . C2 C 1.3450(3) -0.04646(14) 0.6273(2) 0.0745(7) Uani 1 1 d . . . H2B H 1.4124 -0.0859 0.6352 0.089 Uiso 1 1 calc R . . C3 C 1.3050(3) -0.00678(15) 0.53824(19) 0.0767(7) Uani 1 1 d . . . H3A H 1.3452 -0.0190 0.4862 0.092 Uiso 1 1 calc R . . C4 C 1.2054(3) 0.05076(13) 0.52773(16) 0.0676(6) Uani 1 1 d . . . C5 C 1.1444(2) 0.07007(12) 0.60349(15) 0.0610(5) Uani 1 1 d . . . H5A H 1.0762 0.1092 0.5944 0.073 Uiso 1 1 calc R . . C6 C 1.1855(2) 0.03077(11) 0.69334(15) 0.0540(5) Uani 1 1 d . . . C7 C 0.9922(2) 0.12457(12) 0.75462(15) 0.0573(5) Uani 1 1 d . . . C8 C 0.8499(2) 0.10292(13) 0.71683(17) 0.0625(5) Uani 1 1 d . . . H8A H 0.8254 0.0506 0.7100 0.075 Uiso 1 1 calc R . . C9 C 0.7465(2) 0.15862(14) 0.68987(17) 0.0658(6) Uani 1 1 d . . . C10 C 0.7810(3) 0.23669(14) 0.69913(17) 0.0690(6) Uani 1 1 d . . . H10A H 0.7100 0.2741 0.6811 0.083 Uiso 1 1 calc R . . C11 C 0.9202(3) 0.25872(13) 0.73494(17) 0.0690(6) Uani 1 1 d . . . H11A H 0.9429 0.3113 0.7410 0.083 Uiso 1 1 calc R . . C12 C 1.0287(2) 0.20338(13) 0.76264(15) 0.0609(5) Uani 1 1 d . . . C13 C 0.4847(4) 0.39601(19) 0.4077(2) 0.0997(9) Uani 1 1 d . . . H13A H 0.4268 0.4394 0.4049 0.120 Uiso 1 1 calc R . . C14 C 0.6275(4) 0.4035(2) 0.4514(2) 0.1177(13) Uani 1 1 d . A . H14A H 0.6632 0.4512 0.4783 0.141 Uiso 1 1 calc R . . C15 C 0.7181(3) 0.3423(3) 0.4563(2) 0.1113(13) Uani 1 1 d . . . C16 C 0.6565(3) 0.2735(2) 0.4170(2) 0.1039(10) Uani 1 1 d . A . H16A H 0.7124 0.2293 0.4190 0.125 Uiso 1 1 calc R . . C17 C 0.5113(3) 0.2697(2) 0.3747(2) 0.0908(8) Uani 1 1 d . . . H17A H 0.4726 0.2224 0.3487 0.109 Uiso 1 1 calc R A . C18 C 0.8685(5) 0.3688(3) 0.5133(3) 0.0889(14) Uiso 0.690(6) 1 d P A 1 H18A H 0.8812 0.4154 0.5485 0.107 Uiso 0.690(6) 1 calc PR A 1 C19 C 0.9693(4) 0.3287(2) 0.5119(3) 0.0820(13) Uiso 0.690(6) 1 d P A 1 H19A H 0.9564 0.2819 0.4774 0.098 Uiso 0.690(6) 1 calc PR A 1 C18' C 0.8794 0.3157 0.4805 0.0459(18) Uiso 0.310(6) 1 d P A 2 H18' H 0.9116 0.2681 0.4633 0.055 Uiso 0.310(6) 1 calc PR A 2 C19' C 0.9718 0.3798 0.5357 0.0520(19) Uiso 0.310(6) 1 d P A 2 H19' H 0.9386 0.4286 0.5477 0.062 Uiso 0.310(6) 1 calc PR A 2 C20 C 1.1199 0.3557 0.5679 0.0896(9) Uani 1 1 d R . . C21 C 1.1691 0.4170 0.6298 0.1125(11) Uani 1 1 d R A . H21A H 1.1055 0.4536 0.6424 0.135 Uiso 1 1 calc R . . C22 C 1.3122(3) 0.4247(2) 0.6732(2) 0.0995(9) Uani 1 1 d . . . H22A H 1.3425 0.4674 0.7144 0.119 Uiso 1 1 calc R A . C23 C 1.3595(3) 0.31596(17) 0.6007(2) 0.0854(8) Uani 1 1 d . . . H23A H 1.4244 0.2795 0.5898 0.102 Uiso 1 1 calc R A . C24 C 1.2187(3) 0.30464(18) 0.5542(2) 0.0900(8) Uani 1 1 d . A . H24A H 1.1910 0.2617 0.5130 0.108 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 0.1628(8) 0.0982(5) 0.0599(4) 0.0099(3) 0.0264(4) 0.0300(5) Cl2 0.0561(4) 0.0925(5) 0.1336(6) -0.0248(4) 0.0145(4) 0.0069(3) S1 0.0648(3) 0.0662(3) 0.0630(3) 0.0176(3) 0.0130(3) 0.0113(3) O1 0.0695(10) 0.0613(9) 0.0924(12) 0.0212(8) 0.0072(8) 0.0154(8) O2 0.0685(11) 0.0677(10) 0.0960(12) 0.0048(9) -0.0034(9) -0.0032(8) N1 0.0656(13) 0.0867(14) 0.0758(13) -0.0074(11) 0.0001(10) -0.0036(11) N2 0.0602(11) 0.0713(12) 0.0797(13) -0.0113(10) 0.0033(10) -0.0070(10) C1 0.0547(12) 0.0456(10) 0.0738(14) 0.0066(10) 0.0017(10) 0.0012(9) C2 0.0664(14) 0.0624(13) 0.0869(17) -0.0110(12) 0.0056(13) 0.0159(11) C3 0.0797(16) 0.0777(16) 0.0702(15) -0.0151(13) 0.0148(12) 0.0071(13) C4 0.0820(16) 0.0611(12) 0.0551(12) -0.0019(10) 0.0091(11) 0.0037(11) C5 0.0657(13) 0.0509(10) 0.0615(13) 0.0007(9) 0.0074(10) 0.0098(10) C6 0.0517(11) 0.0445(10) 0.0612(12) 0.0015(8) 0.0063(9) -0.0007(8) C7 0.0594(12) 0.0584(11) 0.0533(11) 0.0043(9) 0.0134(9) 0.0093(10) C8 0.0605(13) 0.0576(12) 0.0695(13) -0.0038(10) 0.0168(10) 0.0042(10) C9 0.0576(13) 0.0693(14) 0.0699(14) -0.0114(11) 0.0152(10) 0.0062(10) C10 0.0683(15) 0.0639(13) 0.0700(14) -0.0054(11) 0.0095(11) 0.0155(11) C11 0.0800(16) 0.0543(12) 0.0671(14) -0.0008(10) 0.0091(12) 0.0057(11) C12 0.0639(14) 0.0633(12) 0.0503(11) 0.0019(9) 0.0051(10) 0.0021(10) C13 0.090(2) 0.092(2) 0.098(2) -0.0071(16) -0.0102(16) -0.0041(16) C14 0.105(3) 0.127(3) 0.092(2) 0.011(2) -0.0266(19) -0.041(2) C15 0.0654(17) 0.179(4) 0.0735(18) 0.048(2) -0.0110(14) -0.032(2) C16 0.0638(17) 0.143(3) 0.101(2) 0.016(2) 0.0139(15) 0.0191(19) C17 0.0694(17) 0.102(2) 0.0941(19) -0.0101(16) 0.0082(14) 0.0023(16) C20 0.0588(15) 0.146(3) 0.0602(14) 0.0086(16) 0.0090(12) -0.0192(17) C21 0.0713(18) 0.154(3) 0.104(2) -0.030(2) 0.0082(16) 0.027(2) C22 0.086(2) 0.098(2) 0.105(2) -0.0391(18) 0.0063(16) 0.0025(17) C23 0.0730(16) 0.0779(16) 0.0946(19) -0.0183(14) 0.0023(14) 0.0015(13) C24 0.0848(19) 0.0928(19) 0.0802(17) -0.0138(15) -0.0005(14) -0.0278(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 Cl1 C4 1.748(2) . ? Cl2 C9 1.746(2) . ? S1 C7 1.766(2) . ? S1 C6 1.776(2) . ? O1 C1 1.367(3) . ? O2 C12 1.343(3) . ? N1 C17 1.317(4) . ? N1 C13 1.331(4) . ? N2 C23 1.321(3) . ? N2 C22 1.321(4) . ? C1 C2 1.380(3) . ? C1 C6 1.396(3) . ? C2 C3 1.378(4) . ? C3 C4 1.366(3) . ? C4 C5 1.376(3) . ? C5 C6 1.384(3) . ? C7 C8 1.398(3) . ? C7 C12 1.398(3) . ? C8 C9 1.370(3) . ? C9 C10 1.382(3) . ? C10 C11 1.370(3) . ? C11 C12 1.399(3) . ? C13 C14 1.371(4) . ? C14 C15 1.363(5) . ? C15 C16 1.375(5) . ? C15 C18 1.541(5) . ? C15 C18' 1.585(4) . ? C16 C17 1.384(4) . ? C18 C19 1.203(6) . ? C19 C20 1.542(4) . ? C18' C19' 1.5018(3) . ? C19' C20 1.4540 . ? C20 C24 1.352(3) . ? C20 C21 1.3668 . ? C21 C22 1.374(3) . ? C23 C24 1.369(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 C7 S1 C6 103.07(10) . . ? C17 N1 C13 116.2(3) . . ? C23 N2 C22 115.0(2) . . ? O1 C1 C2 123.7(2) . . ? O1 C1 C6 116.8(2) . . ? C2 C1 C6 119.5(2) . . ? C3 C2 C1 121.0(2) . . ? C4 C3 C2 118.8(2) . . ? C3 C4 C5 121.8(2) . . ? C3 C4 Cl1 119.4(2) . . ? C5 C4 Cl1 118.75(18) . . ? C4 C5 C6 119.4(2) . . ? C5 C6 C1 119.5(2) . . ? C5 C6 S1 124.42(16) . . ? C1 C6 S1 116.08(16) . . ? C8 C7 C12 119.62(19) . . ? C8 C7 S1 118.46(16) . . ? C12 C7 S1 121.79(17) . . ? C9 C8 C7 120.2(2) . . ? C8 C9 C10 120.7(2) . . ? C8 C9 Cl2 119.02(18) . . ? C10 C9 Cl2 120.30(18) . . ? C11 C10 C9 119.8(2) . . ? C10 C11 C12 121.1(2) . . ? O2 C12 C7 124.8(2) . . ? O2 C12 C11 116.5(2) . . ? C7 C12 C11 118.7(2) . . ? N1 C13 C14 123.1(3) . . ? C15 C14 C13 121.2(3) . . ? C14 C15 C16 115.8(3) . . ? C14 C15 C18 108.3(4) . . ? C16 C15 C18 135.8(4) . . ? C14 C15 C18' 145.7(3) . . ? C16 C15 C18' 98.1(3) . . ? C18 C15 C18' 38.78(19) . . ? C15 C16 C17 120.1(3) . . ? N1 C17 C16 123.7(3) . . ? C19 C18 C15 119.4(4) . . ? C18 C19 C20 119.5(4) . . ? C19' C18' C15 108.98(17) . . ? C20 C19' C18' 111.3 . . ? C24 C20 C21 116.36(11) . . ? C24 C20 C19' 145.71(11) . . ? C21 C20 C19' 97.6 . . ? C24 C20 C19 110.59(19) . . ? C21 C20 C19 132.98(16) . . ? C19' C20 C19 36.27(16) . . ? C20 C21 C22 120.08(13) . . ? N2 C22 C21 123.9(2) . . ? N2 C23 C24 124.5(3) . . ? C20 C24 C23 120.2(2) . . ? 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 2.02 2.726(3) 144.0 2_846 O2 H2C N1 0.82 2.01 2.707(3) 141.8 4_666 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.207 _refine_diff_density_min -0.402 _refine_diff_density_rms 0.068