data_q04d _audit_creation_method SHELXTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H31 Cl N2 O3 S' _chemical_formula_weight 439.00 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.3639 0.7018 '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 13.4420(3) _cell_length_b 8.1038(2) _cell_length_c 20.1572(5) _cell_angle_alpha 90.00 _cell_angle_beta 104.2610(10) _cell_angle_gamma 90.00 _cell_volume 2128.08(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9579 _cell_measurement_theta_min 4.52 _cell_measurement_theta_max 69.72 _exptl_crystal_description Thin _exptl_crystal_colour colourless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.370 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 2.719 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.834 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Bruker MicroStar microfocus rotating anode' _diffrn_radiation_monochromator 'Helios multilayer optics' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20456 _diffrn_reflns_av_R_equivalents 0.0260 _diffrn_reflns_av_sigmaI/netI 0.0187 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.58 _diffrn_reflns_theta_max 69.68 _reflns_number_total 3886 _reflns_number_gt 3510 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _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' _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^)+(0.0402P)^2^+1.0379P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3886 _refine_ls_number_parameters 386 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0315 _refine_ls_R_factor_gt 0.0276 _refine_ls_wR_factor_ref 0.0735 _refine_ls_wR_factor_gt 0.0715 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 Cl Cl 0.64826(3) 0.03443(5) -0.065332(17) 0.02190(10) Uani 1 1 d . . . S S 0.58418(2) 0.37753(4) 0.199230(17) 0.01354(10) Uani 1 1 d . . . O1 O 0.19440(7) -0.27075(12) 0.32947(5) 0.0168(2) Uani 1 1 d . . . O2 O 0.68410(7) 0.40957(13) 0.24297(5) 0.0186(2) Uani 1 1 d . . . O3 O 0.51294(8) 0.51095(12) 0.17854(5) 0.0189(2) Uani 1 1 d . . . N1 N 0.36280(8) -0.22346(14) 0.34204(6) 0.0136(2) Uani 1 1 d . . . N2 N 0.52764(9) 0.24231(14) 0.23647(6) 0.0138(2) Uani 1 1 d . . . H2N H 0.4651(15) 0.232(2) 0.2148(10) 0.023(5) Uiso 1 1 d . . . C1 C 0.26413(10) -0.17337(17) 0.32515(7) 0.0139(3) Uani 1 1 d . . . C2 C 0.24071(11) 0.00569(18) 0.30806(8) 0.0178(3) Uani 1 1 d . . . H2A H 0.2519(13) 0.032(2) 0.2639(9) 0.018(4) Uiso 1 1 d . . . H2B H 0.1691(14) 0.018(2) 0.3057(9) 0.017(4) Uiso 1 1 d . . . C3 C 0.30554(11) 0.12049(18) 0.36228(8) 0.0183(3) Uani 1 1 d . . . H3A H 0.2698(13) 0.226(2) 0.3591(9) 0.021(4) Uiso 1 1 d . . . H3B H 0.3107(13) 0.075(2) 0.4064(10) 0.021(4) Uiso 1 1 d . . . C4 C 0.41215(11) 0.15695(17) 0.35204(7) 0.0149(3) Uani 1 1 d . . . H4A H 0.4395(13) 0.240(2) 0.3833(9) 0.018(4) Uiso 1 1 d . . . H4B H 0.4028(12) 0.204(2) 0.3062(9) 0.015(4) Uiso 1 1 d . . . C5 C 0.49172(10) 0.01629(16) 0.36346(7) 0.0129(3) Uani 1 1 d . . . H5 H 0.5094(12) -0.011(2) 0.4121(9) 0.012(4) Uiso 1 1 d . . . C6 C 0.59233(10) 0.07592(17) 0.34521(7) 0.0132(3) Uani 1 1 d . . . H6 H 0.6453(12) -0.013(2) 0.3589(8) 0.011(4) Uiso 1 1 d . . . C7 C 0.58418(10) 0.09156(17) 0.26762(7) 0.0135(3) Uani 1 1 d . . . H7 H 0.6547(13) 0.1045(19) 0.2637(8) 0.012(4) Uiso 1 1 d . . . C8 C 0.54016(10) -0.06661(17) 0.23010(7) 0.0145(3) Uani 1 1 d . . . H8A H 0.5915(13) -0.153(2) 0.2436(8) 0.014(4) Uiso 1 1 d . . . H8B H 0.5282(13) -0.050(2) 0.1806(9) 0.016(4) Uiso 1 1 d . . . C9 C 0.44055(10) -0.12360(17) 0.24753(7) 0.0138(3) Uani 1 1 d . . . H9A H 0.3881(13) -0.042(2) 0.2312(8) 0.013(4) Uiso 1 1 d . . . H9B H 0.4172(12) -0.227(2) 0.2254(9) 0.015(4) Uiso 1 1 d . . . C10 C 0.45642(10) -0.14774(16) 0.32504(7) 0.0128(3) Uani 1 1 d . . . C11 C 0.53636(11) -0.28673(17) 0.35219(8) 0.0155(3) Uani 1 1 d . . . H11A H 0.5348(13) -0.368(2) 0.3154(10) 0.022(4) Uiso 1 1 d . . . H11B H 0.6060(14) -0.244(2) 0.3685(9) 0.016(4) Uiso 1 1 d . . . C12 C 0.49921(11) -0.37045(17) 0.40928(8) 0.0163(3) Uani 1 1 d . . . H12A H 0.5313(12) -0.474(2) 0.4225(8) 0.014(4) Uiso 1 1 d . . . H12B H 0.5110(12) -0.303(2) 0.4516(9) 0.016(4) Uiso 1 1 d . . . C13 C 0.38528(11) -0.38394(17) 0.37685(8) 0.0159(3) Uani 1 1 d . . . H13A H 0.3693(12) -0.474(2) 0.3439(9) 0.013(4) Uiso 1 1 d . . . H13B H 0.3434(13) -0.397(2) 0.4090(9) 0.019(4) Uiso 1 1 d . . . C14 C 0.63955(11) 0.23065(18) 0.38383(7) 0.0162(3) Uani 1 1 d . . . H14A H 0.6995(14) 0.258(2) 0.3689(9) 0.019(4) Uiso 1 1 d . . . H14B H 0.5938(13) 0.323(2) 0.3705(9) 0.018(4) Uiso 1 1 d . . . C15 C 0.67060(12) 0.21068(19) 0.46175(8) 0.0202(3) Uani 1 1 d . . . H15A H 0.6890(14) 0.316(3) 0.4816(10) 0.026(5) Uiso 1 1 d . . . H15B H 0.6099(14) 0.175(2) 0.4802(9) 0.024(4) Uiso 1 1 d . . . C16 C 0.75997(13) 0.0930(3) 0.48578(9) 0.0317(4) Uani 1 1 d . . . H16A H 0.7873(16) 0.095(3) 0.5367(12) 0.037(5) Uiso 1 1 d . . . H16B H 0.7385(18) -0.020(3) 0.4722(12) 0.047(6) Uiso 1 1 d . . . H16C H 0.8160(17) 0.121(3) 0.4646(12) 0.043(6) Uiso 1 1 d . . . C17 C 0.60378(10) 0.28547(17) 0.12369(7) 0.0142(3) Uani 1 1 d . . . C18 C 0.53486(11) 0.31593(19) 0.06122(8) 0.0195(3) Uani 1 1 d . . . H18 H 0.4802(14) 0.386(2) 0.0597(9) 0.022(4) Uiso 1 1 d . . . C19 C 0.54817(12) 0.2398(2) 0.00230(8) 0.0212(3) Uani 1 1 d . . . H19 H 0.5017(15) 0.260(2) -0.0409(10) 0.027(5) Uiso 1 1 d . . . C20 C 0.63024(11) 0.13308(17) 0.00750(7) 0.0167(3) Uani 1 1 d . . . C21 C 0.69920(11) 0.10191(18) 0.06976(8) 0.0179(3) Uani 1 1 d . . . H21 H 0.7535(14) 0.032(2) 0.0715(9) 0.020(4) Uiso 1 1 d . . . C22 C 0.68626(11) 0.17889(18) 0.12835(8) 0.0167(3) Uani 1 1 d . . . H22 H 0.7324(14) 0.159(2) 0.1707(10) 0.023(4) 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 Cl 0.02317(19) 0.0265(2) 0.01634(18) -0.00379(13) 0.00545(14) 0.00452(13) S 0.01396(17) 0.01071(17) 0.01736(18) -0.00120(12) 0.00657(13) -0.00119(11) O1 0.0139(5) 0.0148(5) 0.0222(5) 0.0005(4) 0.0050(4) -0.0024(4) O2 0.0167(5) 0.0182(5) 0.0213(5) -0.0036(4) 0.0059(4) -0.0055(4) O3 0.0220(5) 0.0122(5) 0.0253(5) 0.0006(4) 0.0111(4) 0.0023(4) N1 0.0134(6) 0.0085(6) 0.0196(6) 0.0017(4) 0.0056(5) -0.0005(4) N2 0.0104(6) 0.0140(6) 0.0176(6) 0.0009(4) 0.0047(5) -0.0005(4) C1 0.0154(7) 0.0135(7) 0.0137(6) -0.0007(5) 0.0053(5) -0.0005(5) C2 0.0132(7) 0.0139(7) 0.0272(8) 0.0045(6) 0.0066(6) 0.0022(5) C3 0.0189(7) 0.0111(7) 0.0282(8) 0.0006(6) 0.0121(6) 0.0031(5) C4 0.0166(7) 0.0089(7) 0.0204(7) -0.0018(5) 0.0072(6) -0.0006(5) C5 0.0144(6) 0.0099(7) 0.0154(7) -0.0010(5) 0.0052(5) -0.0004(5) C6 0.0126(6) 0.0110(7) 0.0163(7) -0.0008(5) 0.0041(5) -0.0003(5) C7 0.0116(6) 0.0118(7) 0.0177(7) -0.0003(5) 0.0050(5) 0.0004(5) C8 0.0153(7) 0.0125(7) 0.0167(7) -0.0025(5) 0.0057(5) -0.0003(5) C9 0.0134(7) 0.0105(7) 0.0174(7) -0.0022(5) 0.0035(5) -0.0009(5) C10 0.0111(6) 0.0094(6) 0.0188(7) -0.0009(5) 0.0055(5) -0.0001(5) C11 0.0141(7) 0.0107(7) 0.0222(7) 0.0001(5) 0.0054(6) 0.0020(5) C12 0.0182(7) 0.0106(7) 0.0198(7) 0.0006(5) 0.0041(6) 0.0029(5) C13 0.0185(7) 0.0098(7) 0.0194(7) 0.0021(5) 0.0052(6) 0.0005(5) C14 0.0169(7) 0.0138(7) 0.0181(7) -0.0020(5) 0.0048(6) -0.0035(5) C15 0.0243(8) 0.0202(8) 0.0170(7) -0.0049(6) 0.0069(6) -0.0093(6) C16 0.0254(9) 0.0498(12) 0.0189(8) 0.0051(8) 0.0035(7) -0.0004(8) C17 0.0145(6) 0.0123(7) 0.0172(7) 0.0001(5) 0.0066(5) -0.0017(5) C18 0.0153(7) 0.0200(8) 0.0232(8) 0.0011(6) 0.0046(6) 0.0053(6) C19 0.0187(7) 0.0254(8) 0.0176(8) 0.0014(6) 0.0006(6) 0.0038(6) C20 0.0184(7) 0.0157(7) 0.0175(7) -0.0017(5) 0.0075(6) -0.0012(5) C21 0.0160(7) 0.0173(7) 0.0211(7) 0.0000(6) 0.0060(6) 0.0045(6) C22 0.0149(7) 0.0180(7) 0.0169(7) 0.0018(6) 0.0035(6) 0.0013(5) _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 Cl C20 1.7403(14) . ? S O3 1.4364(10) . ? S O2 1.4371(10) . ? S N2 1.6195(12) . ? S C17 1.7726(14) . ? O1 C1 1.2446(17) . ? N1 C1 1.3481(18) . ? N1 C13 1.4733(17) . ? N1 C10 1.5133(16) . ? N2 C7 1.4931(17) . ? N2 H2N 0.85(2) . ? C1 C2 1.507(2) . ? C2 C3 1.533(2) . ? C2 H2A 0.962(19) . ? C2 H2B 0.957(17) . ? C3 C4 1.5263(19) . ? C3 H3A 0.977(19) . ? C3 H3B 0.948(19) . ? C4 C5 1.5412(18) . ? C4 H4A 0.935(19) . ? C4 H4B 0.980(18) . ? C5 C10 1.5526(18) . ? C5 C6 1.5629(18) . ? C5 H5 0.976(17) . ? C6 C14 1.5290(19) . ? C6 C7 1.5460(19) . ? C6 H6 1.002(16) . ? C7 C8 1.5312(19) . ? C7 H7 0.977(16) . ? C8 C9 1.5366(18) . ? C8 H8A 0.972(17) . ? C8 H8B 0.980(18) . ? C9 C10 1.5365(19) . ? C9 H9A 0.963(17) . ? C9 H9B 0.962(18) . ? C10 C11 1.5598(18) . ? C11 C12 1.522(2) . ? C11 H11A 0.989(19) . ? C11 H11B 0.976(18) . ? C12 C13 1.514(2) . ? C12 H12A 0.950(18) . ? C12 H12B 0.991(18) . ? C13 H13A 0.976(18) . ? C13 H13B 0.963(18) . ? C14 C15 1.531(2) . ? C14 H14A 0.952(18) . ? C14 H14B 0.964(18) . ? C15 C16 1.517(2) . ? C15 H15A 0.95(2) . ? C15 H15B 1.019(19) . ? C16 H16A 1.00(2) . ? C16 H16B 0.98(3) . ? C16 H16C 0.98(2) . ? C17 C18 1.389(2) . ? C17 C22 1.390(2) . ? C18 C19 1.389(2) . ? C18 H18 0.920(19) . ? C19 C20 1.385(2) . ? C19 H19 0.95(2) . ? C20 C21 1.387(2) . ? C21 C22 1.384(2) . ? C21 H21 0.917(18) . ? C22 H22 0.937(19) . ? 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 O3 S O2 119.84(6) . . ? O3 S N2 106.76(6) . . ? O2 S N2 108.20(6) . . ? O3 S C17 107.27(6) . . ? O2 S C17 106.79(6) . . ? N2 S C17 107.42(6) . . ? C1 N1 C13 117.37(11) . . ? C1 N1 C10 129.94(12) . . ? C13 N1 C10 112.42(10) . . ? C7 N2 S 120.01(9) . . ? C7 N2 H2N 118.2(13) . . ? S N2 H2N 110.2(12) . . ? O1 C1 N1 120.16(13) . . ? O1 C1 C2 120.54(12) . . ? N1 C1 C2 119.01(12) . . ? C1 C2 C3 111.80(12) . . ? C1 C2 H2A 110.6(10) . . ? C3 C2 H2A 109.6(10) . . ? C1 C2 H2B 105.3(10) . . ? C3 C2 H2B 111.1(10) . . ? H2A C2 H2B 108.3(14) . . ? C4 C3 C2 114.13(12) . . ? C4 C3 H3A 106.5(10) . . ? C2 C3 H3A 107.6(10) . . ? C4 C3 H3B 110.3(11) . . ? C2 C3 H3B 109.4(11) . . ? H3A C3 H3B 108.7(15) . . ? C3 C4 C5 118.48(12) . . ? C3 C4 H4A 105.9(10) . . ? C5 C4 H4A 106.9(11) . . ? C3 C4 H4B 107.2(10) . . ? C5 C4 H4B 110.8(10) . . ? H4A C4 H4B 106.8(15) . . ? C4 C5 C10 116.30(11) . . ? C4 C5 C6 110.18(11) . . ? C10 C5 C6 108.85(11) . . ? C4 C5 H5 108.0(9) . . ? C10 C5 H5 105.8(10) . . ? C6 C5 H5 107.3(9) . . ? C14 C6 C7 111.40(11) . . ? C14 C6 C5 114.11(11) . . ? C7 C6 C5 114.44(11) . . ? C14 C6 H6 105.7(9) . . ? C7 C6 H6 101.9(9) . . ? C5 C6 H6 108.1(9) . . ? N2 C7 C8 112.49(11) . . ? N2 C7 C6 113.23(11) . . ? C8 C7 C6 110.70(11) . . ? N2 C7 H7 106.4(9) . . ? C8 C7 H7 108.3(9) . . ? C6 C7 H7 105.2(10) . . ? C7 C8 C9 113.03(11) . . ? C7 C8 H8A 107.6(10) . . ? C9 C8 H8A 108.5(10) . . ? C7 C8 H8B 109.7(10) . . ? C9 C8 H8B 109.8(10) . . ? H8A C8 H8B 108.0(13) . . ? C10 C9 C8 111.11(11) . . ? C10 C9 H9A 110.0(10) . . ? C8 C9 H9A 108.7(10) . . ? C10 C9 H9B 108.0(10) . . ? C8 C9 H9B 110.9(10) . . ? H9A C9 H9B 108.0(14) . . ? N1 C10 C9 111.53(11) . . ? N1 C10 C5 113.78(11) . . ? C9 C10 C5 110.31(11) . . ? N1 C10 C11 99.62(10) . . ? C9 C10 C11 111.09(11) . . ? C5 C10 C11 110.10(11) . . ? C12 C11 C10 105.14(11) . . ? C12 C11 H11A 108.5(10) . . ? C10 C11 H11A 109.5(10) . . ? C12 C11 H11B 111.7(10) . . ? C10 C11 H11B 112.4(10) . . ? H11A C11 H11B 109.5(14) . . ? C13 C12 C11 101.02(11) . . ? C13 C12 H12A 113.5(10) . . ? C11 C12 H12A 113.3(10) . . ? C13 C12 H12B 109.9(10) . . ? C11 C12 H12B 113.1(10) . . ? H12A C12 H12B 106.2(14) . . ? N1 C13 C12 102.06(11) . . ? N1 C13 H13A 110.6(10) . . ? C12 C13 H13A 112.2(9) . . ? N1 C13 H13B 109.5(10) . . ? C12 C13 H13B 114.5(10) . . ? H13A C13 H13B 107.9(14) . . ? C6 C14 C15 114.18(12) . . ? C6 C14 H14A 107.7(10) . . ? C15 C14 H14A 108.1(11) . . ? C6 C14 H14B 109.8(10) . . ? C15 C14 H14B 111.2(10) . . ? H14A C14 H14B 105.5(14) . . ? C16 C15 C14 112.85(13) . . ? C16 C15 H15A 109.0(11) . . ? C14 C15 H15A 108.4(11) . . ? C16 C15 H15B 110.3(10) . . ? C14 C15 H15B 111.3(10) . . ? H15A C15 H15B 104.7(15) . . ? C15 C16 H16A 112.3(12) . . ? C15 C16 H16B 110.0(14) . . ? H16A C16 H16B 108.0(18) . . ? C15 C16 H16C 110.5(13) . . ? H16A C16 H16C 108.4(18) . . ? H16B C16 H16C 107.4(18) . . ? C18 C17 C22 120.95(13) . . ? C18 C17 S 119.79(11) . . ? C22 C17 S 119.22(11) . . ? C19 C18 C17 119.91(13) . . ? C19 C18 H18 120.9(11) . . ? C17 C18 H18 119.2(11) . . ? C20 C19 C18 118.73(14) . . ? C20 C19 H19 120.7(11) . . ? C18 C19 H19 120.6(11) . . ? C19 C20 C21 121.62(13) . . ? C19 C20 Cl 119.78(12) . . ? C21 C20 Cl 118.60(11) . . ? C22 C21 C20 119.56(13) . . ? C22 C21 H21 120.8(11) . . ? C20 C21 H21 119.6(11) . . ? C21 C22 C17 119.22(13) . . ? C21 C22 H22 120.5(11) . . ? C17 C22 H22 120.3(11) . . ? 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 O3 S N2 C7 -176.55(10) . . . . ? O2 S N2 C7 -46.30(12) . . . . ? C17 S N2 C7 68.65(12) . . . . ? C13 N1 C1 O1 -10.76(19) . . . . ? C10 N1 C1 O1 162.72(13) . . . . ? C13 N1 C1 C2 163.05(12) . . . . ? C10 N1 C1 C2 -23.5(2) . . . . ? O1 C1 C2 C3 124.40(14) . . . . ? N1 C1 C2 C3 -49.39(17) . . . . ? C1 C2 C3 C4 84.26(15) . . . . ? C2 C3 C4 C5 -69.15(17) . . . . ? C3 C4 C5 C10 51.43(17) . . . . ? C3 C4 C5 C6 175.89(12) . . . . ? C4 C5 C6 C14 55.47(15) . . . . ? C10 C5 C6 C14 -175.90(11) . . . . ? C4 C5 C6 C7 -74.51(14) . . . . ? C10 C5 C6 C7 54.12(15) . . . . ? S N2 C7 C8 -113.16(12) . . . . ? S N2 C7 C6 120.41(11) . . . . ? C14 C6 C7 N2 -54.54(15) . . . . ? C5 C6 C7 N2 76.77(14) . . . . ? C14 C6 C7 C8 178.08(11) . . . . ? C5 C6 C7 C8 -50.61(15) . . . . ? N2 C7 C8 C9 -77.12(15) . . . . ? C6 C7 C8 C9 50.66(15) . . . . ? C7 C8 C9 C10 -56.28(15) . . . . ? C1 N1 C10 C9 -54.69(18) . . . . ? C13 N1 C10 C9 119.05(12) . . . . ? C1 N1 C10 C5 70.87(18) . . . . ? C13 N1 C10 C5 -115.39(12) . . . . ? C1 N1 C10 C11 -172.02(13) . . . . ? C13 N1 C10 C11 1.71(14) . . . . ? C8 C9 C10 N1 -173.09(11) . . . . ? C8 C9 C10 C5 59.45(14) . . . . ? C8 C9 C10 C11 -62.93(14) . . . . ? C4 C5 C10 N1 -58.38(16) . . . . ? C6 C5 C10 N1 176.49(11) . . . . ? C4 C5 C10 C9 67.83(14) . . . . ? C6 C5 C10 C9 -57.31(14) . . . . ? C4 C5 C10 C11 -169.22(11) . . . . ? C6 C5 C10 C11 65.65(14) . . . . ? N1 C10 C11 C12 -27.84(13) . . . . ? C9 C10 C11 C12 -145.50(11) . . . . ? C5 C10 C11 C12 92.00(13) . . . . ? C10 C11 C12 C13 43.66(13) . . . . ? C1 N1 C13 C12 -160.57(12) . . . . ? C10 N1 C13 C12 24.84(14) . . . . ? C11 C12 C13 N1 -40.82(13) . . . . ? C7 C6 C14 C15 -167.90(12) . . . . ? C5 C6 C14 C15 60.62(16) . . . . ? C6 C14 C15 C16 67.98(17) . . . . ? O3 S C17 C18 -17.02(13) . . . . ? O2 S C17 C18 -146.68(12) . . . . ? N2 S C17 C18 97.44(12) . . . . ? O3 S C17 C22 165.24(11) . . . . ? O2 S C17 C22 35.59(13) . . . . ? N2 S C17 C22 -80.29(12) . . . . ? C22 C17 C18 C19 -0.2(2) . . . . ? S C17 C18 C19 -177.91(12) . . . . ? C17 C18 C19 C20 0.6(2) . . . . ? C18 C19 C20 C21 -0.4(2) . . . . ? C18 C19 C20 Cl 179.45(12) . . . . ? C19 C20 C21 C22 0.0(2) . . . . ? Cl C20 C21 C22 -179.92(11) . . . . ? C20 C21 C22 C17 0.4(2) . . . . ? C18 C17 C22 C21 -0.3(2) . . . . ? S C17 C22 C21 177.45(11) . . . . ? 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 N2 H2N O1 0.85(2) 2.11(2) 2.9549(15) 172.3(17) 2 _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 66.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.382 _refine_diff_density_min -0.380 _refine_diff_density_rms 0.043