data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H16 N6 O2 S' _chemical_formula_sum 'C18 H16 N6 O2 S' _chemical_formula_weight 380.43 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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7322(17) _cell_length_b 7.9076(17) _cell_length_c 15.664(3) _cell_angle_alpha 79.857(3) _cell_angle_beta 81.807(2) _cell_angle_gamma 74.309(3) _cell_volume 903.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 1875 _cell_measurement_theta_min 0.976 _cell_measurement_theta_max 0.984 _exptl_crystal_description sheet _exptl_crystal_colour red _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.399 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 396 _exptl_absorpt_coefficient_mu 0.206 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9757 _exptl_absorpt_correction_T_max 0.9837 _exptl_absorpt_process_details 'SADABS, Bruker(2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(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 'Bruker CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4539 _diffrn_reflns_av_R_equivalents 0.0590 _diffrn_reflns_av_sigmaI/netI 0.0486 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3141 _reflns_number_gt 2328 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (BRUKER 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (BRUKER 2000)' _computing_structure_solution 'SHELXTL (BRUKER 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0995P)^2^+0.1121P] 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 SHELXL _refine_ls_extinction_coef ? _refine_ls_number_reflns 3141 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0784 _refine_ls_R_factor_gt 0.0600 _refine_ls_wR_factor_ref 0.1805 _refine_ls_wR_factor_gt 0.1674 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _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 C1 C 0.2908(3) 0.6359(4) 1.15218(17) 0.0517(6) Uani 1 1 d . . . C2 C 0.2097(4) 0.7849(4) 1.09468(18) 0.0544(7) Uani 1 1 d . . . C3 C 0.1714(4) 0.9548(4) 1.1184(2) 0.0671(8) Uani 1 1 d . . . H3 H 0.1162 1.0540 1.0812 0.081 Uiso 1 1 calc R . . C4 C 0.2165(4) 0.9726(5) 1.1969(2) 0.0724(9) Uani 1 1 d . . . H4 H 0.1947 1.0846 1.2132 0.087 Uiso 1 1 calc R . . C5 C 0.2950(4) 0.8227(5) 1.25223(19) 0.0652(8) Uani 1 1 d . . . C6 C 0.3341(4) 0.6524(4) 1.23256(18) 0.0610(8) Uani 1 1 d . . . H6 H 0.3865 0.5542 1.2711 0.073 Uiso 1 1 calc R . . C7 C 0.2257(3) 0.5798(4) 1.01521(17) 0.0532(7) Uani 1 1 d . . . C8 C 0.2501(3) 0.2708(4) 0.87792(16) 0.0500(6) Uani 1 1 d . . . C9 C 0.1685(4) 0.3680(4) 0.80396(17) 0.0541(7) Uani 1 1 d . . . H9 H 0.1239 0.4904 0.8006 0.065 Uiso 1 1 calc R . . C10 C 0.1536(4) 0.2863(4) 0.73714(18) 0.0557(7) Uani 1 1 d . . . H10 H 0.1015 0.3541 0.6882 0.067 Uiso 1 1 calc R . . C11 C 0.2156(4) 0.1002(4) 0.74043(18) 0.0581(7) Uani 1 1 d . . . C12 C 0.2992(4) 0.0052(4) 0.81425(19) 0.0655(8) Uani 1 1 d . . . H12 H 0.3440 -0.1173 0.8181 0.079 Uiso 1 1 calc R . . C13 C 0.3162(4) 0.0886(4) 0.88045(18) 0.0591(7) Uani 1 1 d . . . H13 H 0.3733 0.0220 0.9284 0.071 Uiso 1 1 calc R . . C14 C 0.1115(4) 0.1249(4) 0.5963(2) 0.0716(9) Uani 1 1 d . . . H14A H 0.0108 0.2208 0.6129 0.086 Uiso 1 1 calc R . . H14B H 0.0654 0.0503 0.5670 0.086 Uiso 1 1 calc R . . C15 C 0.2479(4) 0.2015(5) 0.5342(2) 0.0800(10) Uani 1 1 d . . . H15A H 0.2991 0.2706 0.5645 0.096 Uiso 1 1 calc R . . H15B H 0.3452 0.1054 0.5149 0.096 Uiso 1 1 calc R . . C16 C 0.1675(5) 0.3140(5) 0.4586(2) 0.0788(10) Uani 1 1 d . . . C17 C 0.2070(9) -0.1770(6) 0.6843(3) 0.1266(17) Uani 1 1 d . . . H17A H 0.2250 -0.2287 0.7443 0.152 Uiso 1 1 calc R . . H17B H 0.0954 -0.1966 0.6714 0.152 Uiso 1 1 calc R . . C18 C 0.3451(9) -0.2606(8) 0.6314(4) 0.172(3) Uani 1 1 d . . . H18A H 0.3187 -0.2241 0.5719 0.258 Uiso 1 1 calc R . . H18B H 0.3612 -0.3866 0.6459 0.258 Uiso 1 1 calc R . . H18C H 0.4537 -0.2304 0.6388 0.258 Uiso 1 1 calc R . . N1 N 0.1742(3) 0.7472(3) 1.01773(14) 0.0577(6) Uani 1 1 d . . . N2 N 0.3404(4) 0.8443(5) 1.3369(2) 0.0838(9) Uani 1 1 d . . . N3 N 0.2058(3) 0.5111(3) 0.94240(14) 0.0584(6) Uani 1 1 d . . . N4 N 0.2685(3) 0.3436(3) 0.94943(14) 0.0551(6) Uani 1 1 d . . . N5 N 0.1887(4) 0.0201(4) 0.67474(17) 0.0809(8) Uani 1 1 d . . . N6 N 0.1027(5) 0.3986(5) 0.4013(2) 0.1170(13) Uani 1 1 d . . . O1 O 0.3101(4) 0.9923(5) 1.3551(2) 0.1218(11) Uani 1 1 d . . . O2 O 0.4043(4) 0.7125(5) 1.38632(18) 0.1084(10) Uani 1 1 d . . . S1 S 0.32163(10) 0.44447(10) 1.10693(5) 0.0590(3) 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 C1 0.0466(14) 0.0582(17) 0.0506(15) -0.0139(13) -0.0009(11) -0.0118(12) C2 0.0552(15) 0.0556(17) 0.0519(15) -0.0108(13) 0.0025(12) -0.0149(13) C3 0.078(2) 0.0552(18) 0.0655(19) -0.0138(15) -0.0024(15) -0.0113(15) C4 0.077(2) 0.069(2) 0.077(2) -0.0283(18) 0.0058(17) -0.0226(17) C5 0.0595(17) 0.085(2) 0.0591(18) -0.0271(17) 0.0007(14) -0.0252(16) C6 0.0584(17) 0.072(2) 0.0553(17) -0.0148(15) -0.0095(13) -0.0145(14) C7 0.0493(15) 0.0623(18) 0.0470(15) -0.0100(13) -0.0006(11) -0.0135(13) C8 0.0484(14) 0.0577(17) 0.0433(14) -0.0078(12) 0.0009(11) -0.0145(12) C9 0.0602(16) 0.0488(16) 0.0510(15) -0.0089(13) -0.0039(12) -0.0096(13) C10 0.0634(17) 0.0535(17) 0.0473(15) -0.0061(12) -0.0075(12) -0.0097(13) C11 0.0704(17) 0.0546(17) 0.0478(15) -0.0109(13) -0.0035(13) -0.0126(14) C12 0.086(2) 0.0490(17) 0.0557(17) -0.0072(14) -0.0088(15) -0.0060(15) C13 0.0658(17) 0.0592(18) 0.0477(15) -0.0037(13) -0.0078(13) -0.0093(14) C14 0.084(2) 0.075(2) 0.0617(18) -0.0224(16) -0.0156(16) -0.0169(17) C15 0.070(2) 0.103(3) 0.0618(19) -0.0208(19) -0.0163(16) -0.0014(18) C16 0.092(2) 0.072(2) 0.063(2) -0.0195(18) -0.0112(18) 0.0042(19) C17 0.203(5) 0.096(3) 0.083(3) -0.027(3) -0.028(3) -0.024(3) C18 0.171(5) 0.123(4) 0.157(5) 0.007(4) 0.027(4) 0.035(4) N1 0.0682(15) 0.0598(16) 0.0444(12) -0.0072(11) -0.0046(10) -0.0160(12) N2 0.0740(19) 0.113(3) 0.078(2) -0.045(2) -0.0068(15) -0.0254(18) N3 0.0620(14) 0.0651(16) 0.0487(13) -0.0141(12) -0.0039(11) -0.0144(12) N4 0.0553(13) 0.0620(16) 0.0488(13) -0.0126(11) 0.0027(10) -0.0173(11) N5 0.130(2) 0.0555(16) 0.0591(15) -0.0146(13) -0.0253(15) -0.0151(16) N6 0.138(3) 0.099(3) 0.089(2) 0.004(2) -0.030(2) 0.011(2) O1 0.145(3) 0.128(3) 0.114(2) -0.073(2) -0.0201(19) -0.032(2) O2 0.122(2) 0.139(3) 0.0770(17) -0.0313(18) -0.0376(16) -0.029(2) S1 0.0676(5) 0.0540(5) 0.0543(5) -0.0106(3) -0.0109(3) -0.0092(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 C1 C6 1.384(4) . ? C1 C2 1.407(4) . ? C1 S1 1.728(3) . ? C2 N1 1.372(4) . ? C2 C3 1.400(4) . ? C3 C4 1.365(5) . ? C3 H3 0.9300 . ? C4 C5 1.387(5) . ? C4 H4 0.9300 . ? C5 C6 1.378(4) . ? C5 N2 1.469(4) . ? C6 H6 0.9300 . ? C7 N1 1.281(4) . ? C7 N3 1.390(4) . ? C7 S1 1.758(3) . ? C8 N4 1.387(3) . ? C8 C13 1.388(4) . ? C8 C9 1.401(4) . ? C9 C10 1.356(4) . ? C9 H9 0.9300 . ? C10 C11 1.413(4) . ? C10 H10 0.9300 . ? C11 N5 1.366(4) . ? C11 C12 1.401(4) . ? C12 C13 1.362(4) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 N5 1.461(4) . ? C14 C15 1.507(5) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.456(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 N6 1.114(4) . ? C17 C18 1.350(7) . ? C17 N5 1.509(5) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? N2 O1 1.206(4) . ? N2 O2 1.215(4) . ? N3 N4 1.272(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 C6 C1 C2 121.6(3) . . ? C6 C1 S1 128.3(2) . . ? C2 C1 S1 110.1(2) . . ? N1 C2 C3 125.3(3) . . ? N1 C2 C1 114.8(2) . . ? C3 C2 C1 119.9(3) . . ? C4 C3 C2 118.9(3) . . ? C4 C3 H3 120.6 . . ? C2 C3 H3 120.6 . . ? C3 C4 C5 119.7(3) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C6 C5 C4 123.8(3) . . ? C6 C5 N2 117.3(3) . . ? C4 C5 N2 118.8(3) . . ? C5 C6 C1 116.1(3) . . ? C5 C6 H6 121.9 . . ? C1 C6 H6 121.9 . . ? N1 C7 N3 120.5(3) . . ? N1 C7 S1 117.0(2) . . ? N3 C7 S1 122.4(2) . . ? N4 C8 C13 117.4(2) . . ? N4 C8 C9 124.6(3) . . ? C13 C8 C9 118.0(3) . . ? C10 C9 C8 121.0(3) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C9 C10 C11 121.3(3) . . ? C9 C10 H10 119.3 . . ? C11 C10 H10 119.3 . . ? N5 C11 C12 122.9(3) . . ? N5 C11 C10 120.1(3) . . ? C12 C11 C10 117.0(3) . . ? C13 C12 C11 121.3(3) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C12 C13 C8 121.4(3) . . ? C12 C13 H13 119.3 . . ? C8 C13 H13 119.3 . . ? N5 C14 C15 112.2(3) . . ? N5 C14 H14A 109.2 . . ? C15 C14 H14A 109.2 . . ? N5 C14 H14B 109.2 . . ? C15 C14 H14B 109.2 . . ? H14A C14 H14B 107.9 . . ? C16 C15 C14 111.9(3) . . ? C16 C15 H15A 109.2 . . ? C14 C15 H15A 109.2 . . ? C16 C15 H15B 109.2 . . ? C14 C15 H15B 109.2 . . ? H15A C15 H15B 107.9 . . ? N6 C16 C15 178.4(5) . . ? C18 C17 N5 113.1(5) . . ? C18 C17 H17A 109.0 . . ? N5 C17 H17A 109.0 . . ? C18 C17 H17B 109.0 . . ? N5 C17 H17B 109.0 . . ? H17A C17 H17B 107.8 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C7 N1 C2 110.5(2) . . ? O1 N2 O2 122.7(3) . . ? O1 N2 C5 118.6(4) . . ? O2 N2 C5 118.7(3) . . ? N4 N3 C7 112.5(2) . . ? N3 N4 C8 113.9(2) . . ? C11 N5 C14 121.1(3) . . ? C11 N5 C17 122.5(3) . . ? C14 N5 C17 115.7(3) . . ? C1 S1 C7 87.54(13) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.662 _refine_diff_density_min -0.391 _refine_diff_density_rms 0.050 #===END data_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H17 Cl2 N5 S' _chemical_formula_sum 'C19 H17 Cl2 N5 S' _chemical_formula_weight 418.34 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' '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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 28.332(6) _cell_length_b 5.7844(14) _cell_length_c 24.118(6) _cell_angle_alpha 90.00 _cell_angle_beta 95.131(3) _cell_angle_gamma 90.00 _cell_volume 3936.7(16) _cell_formula_units_Z 8 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 642 _cell_measurement_theta_min 2.888 _cell_measurement_theta_max 18.130 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.412 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1728 _exptl_absorpt_coefficient_mu 0.450 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9315 _exptl_absorpt_correction_T_max 0.9564 _exptl_absorpt_process_details 'SADABS, Bruker(2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(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 'Bruker CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9307 _diffrn_reflns_av_R_equivalents 0.1071 _diffrn_reflns_av_sigmaI/netI 0.1802 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3447 _reflns_number_gt 1135 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (BRUKER 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (BRUKER 2000)' _computing_structure_solution 'SHELXTL (BRUKER 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0511P)^2^+1.9800P] 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 3447 _refine_ls_number_parameters 246 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.2178 _refine_ls_R_factor_gt 0.0890 _refine_ls_wR_factor_ref 0.1949 _refine_ls_wR_factor_gt 0.1758 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 1.012 _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 C1 C 0.3462(3) -0.1519(13) 0.8734(3) 0.058(2) Uani 1 1 d . . . C2 C 0.3949(3) -0.1826(15) 0.8822(3) 0.061(2) Uani 1 1 d . . . C3 C 0.4119(3) -0.3672(16) 0.9178(3) 0.087(3) Uani 1 1 d DU . . H3 H 0.4446 -0.3840 0.9241 0.104 Uiso 1 1 calc R . . C4 C 0.3835(3) -0.5274(18) 0.9443(4) 0.108(3) Uani 1 1 d DU . . H4 H 0.3954 -0.6480 0.9669 0.130 Uiso 1 1 calc R . . C5 C 0.3367(3) -0.4819(15) 0.9323(3) 0.074(2) Uani 1 1 d U . . C6 C 0.3157(3) -0.3104(16) 0.8992(3) 0.068(2) Uani 1 1 d . . . C7 C 0.3932(3) 0.1182(15) 0.8277(3) 0.054(2) Uani 1 1 d . . . C8 C 0.3876(3) 0.6018(14) 0.7412(3) 0.053(2) Uani 1 1 d . . . C9 C 0.3498(2) 0.7279(14) 0.7134(3) 0.052(2) Uani 1 1 d . . . C10 C 0.3601(2) 0.9102(14) 0.6805(3) 0.056(2) Uani 1 1 d . . . H10 H 0.3349 0.9906 0.6619 0.067 Uiso 1 1 calc R . . C11 C 0.4074(3) 0.9850(14) 0.6728(3) 0.051(2) Uani 1 1 d . . . C12 C 0.4447(3) 0.8492(14) 0.7007(3) 0.059(2) Uani 1 1 d . . . H12 H 0.4761 0.8868 0.6965 0.071 Uiso 1 1 calc R . . C13 C 0.4348(3) 0.6654(14) 0.7335(3) 0.056(2) Uani 1 1 d . . . H13 H 0.4597 0.5804 0.7511 0.067 Uiso 1 1 calc R . . C14 C 0.2996(2) 0.6669(13) 0.7188(3) 0.069(2) Uani 1 1 d . . . H14A H 0.2808 0.8054 0.7183 0.103 Uiso 1 1 calc R . . H14B H 0.2972 0.5865 0.7533 0.103 Uiso 1 1 calc R . . H14C H 0.2881 0.5693 0.6883 0.103 Uiso 1 1 calc R . . C15 C 0.4627(3) 1.2481(13) 0.6329(3) 0.063(2) Uani 1 1 d . . . H15A H 0.4847 1.1801 0.6615 0.076 Uiso 1 1 calc R . . H15B H 0.4635 1.4144 0.6381 0.076 Uiso 1 1 calc R . . C16 C 0.4797(3) 1.1904(13) 0.5745(3) 0.064(2) Uani 1 1 d . . . H16A H 0.4625 1.2852 0.5464 0.076 Uiso 1 1 calc R . . H16B H 0.5132 1.2268 0.5746 0.076 Uiso 1 1 calc R . . C17 C 0.4722(3) 0.9437(17) 0.5604(3) 0.063(2) Uani 1 1 d . . . C18 C 0.3769(3) 1.2874(14) 0.6085(3) 0.074(3) Uani 1 1 d . . . H18A H 0.3884 1.4359 0.5967 0.089 Uiso 1 1 calc R . . H18B H 0.3523 1.3172 0.6331 0.089 Uiso 1 1 calc R . . C19 C 0.3553(3) 1.1627(16) 0.5585(3) 0.087(3) Uani 1 1 d . . . H19A H 0.3751 1.1808 0.5285 0.130 Uiso 1 1 calc R . . H19B H 0.3245 1.2255 0.5477 0.130 Uiso 1 1 calc R . . H19C H 0.3525 1.0015 0.5670 0.130 Uiso 1 1 calc R . . N1 N 0.4217(2) -0.0227(12) 0.8560(3) 0.0606(18) Uani 1 1 d . . . N2 N 0.4109(2) 0.2987(11) 0.7970(2) 0.0521(16) Uani 1 1 d . . . N3 N 0.3757(2) 0.4181(12) 0.7728(2) 0.0543(16) Uani 1 1 d . . . N4 N 0.4160(2) 1.1671(11) 0.6403(2) 0.0561(17) Uani 1 1 d . . . N5 N 0.4657(3) 0.7563(14) 0.5503(3) 0.085(2) Uani 1 1 d . . . S1 S 0.33235(7) 0.0772(4) 0.83018(8) 0.0670(7) Uani 1 1 d . . . Cl1 Cl 0.29780(10) -0.6693(5) 0.96328(11) 0.1230(11) Uani 1 1 d . . . Cl2 Cl 0.25713(8) -0.2704(5) 0.88708(11) 0.1177(11) 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 C1 0.078(6) 0.043(5) 0.056(5) 0.004(4) 0.018(5) -0.015(4) C2 0.063(6) 0.056(6) 0.063(6) -0.006(5) 0.003(5) -0.007(5) C3 0.083(6) 0.089(7) 0.090(6) -0.033(6) 0.020(5) -0.012(5) C4 0.082(5) 0.131(8) 0.116(7) -0.076(6) 0.034(5) -0.023(5) C5 0.103(5) 0.049(6) 0.071(6) 0.003(5) 0.019(6) -0.003(5) C6 0.045(5) 0.083(7) 0.077(6) -0.030(6) 0.005(4) -0.021(5) C7 0.055(5) 0.055(6) 0.056(5) -0.021(5) 0.022(4) -0.022(5) C8 0.058(6) 0.052(6) 0.049(5) -0.011(4) 0.009(4) -0.008(5) C9 0.038(5) 0.064(6) 0.054(5) -0.001(5) 0.006(4) -0.004(4) C10 0.043(5) 0.070(6) 0.054(5) -0.003(5) 0.001(4) 0.008(4) C11 0.059(6) 0.060(6) 0.036(5) -0.009(4) 0.011(4) 0.007(5) C12 0.047(5) 0.062(6) 0.068(5) -0.017(5) 0.002(4) 0.000(4) C13 0.049(5) 0.063(6) 0.056(5) -0.007(5) 0.007(4) -0.002(4) C14 0.043(5) 0.087(7) 0.077(5) 0.000(5) 0.010(4) 0.002(4) C15 0.067(6) 0.057(6) 0.066(6) 0.004(4) 0.013(4) -0.011(4) C16 0.074(6) 0.047(6) 0.074(6) 0.006(5) 0.026(4) -0.005(4) C17 0.067(6) 0.052(7) 0.074(6) 0.004(6) 0.025(4) 0.006(5) C18 0.064(6) 0.061(6) 0.098(7) 0.026(6) 0.016(5) 0.017(5) C19 0.077(6) 0.123(9) 0.056(5) 0.021(6) -0.015(5) 0.011(6) N1 0.060(5) 0.049(5) 0.075(5) 0.003(4) 0.012(4) -0.005(4) N2 0.060(4) 0.047(4) 0.051(4) -0.005(3) 0.013(3) -0.013(4) N3 0.054(4) 0.055(5) 0.054(4) 0.000(4) 0.008(3) -0.007(4) N4 0.051(4) 0.056(5) 0.063(4) 0.000(4) 0.015(4) 0.000(4) N5 0.091(5) 0.063(6) 0.103(6) -0.003(5) 0.029(4) 0.009(4) S1 0.0529(13) 0.0721(17) 0.0769(14) -0.0055(13) 0.0111(11) -0.0121(11) Cl1 0.159(3) 0.092(2) 0.128(2) 0.0058(18) 0.0657(19) -0.0485(18) Cl2 0.0749(19) 0.127(3) 0.152(2) 0.0365(19) 0.0154(16) -0.0116(15) _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 C1 C2 1.388(10) . ? C1 C6 1.438(10) . ? C1 S1 1.710(8) . ? C2 N1 1.385(9) . ? C2 C3 1.426(11) . ? C3 C4 1.416(8) . ? C3 H3 0.9300 . ? C4 C5 1.356(11) . ? C4 H4 0.9300 . ? C5 C6 1.375(10) . ? C5 Cl1 1.760(8) . ? C6 Cl2 1.675(8) . ? C7 N1 1.296(9) . ? C7 N2 1.398(9) . ? C7 S1 1.747(7) . ? C8 N3 1.367(8) . ? C8 C13 1.414(9) . ? C8 C9 1.416(9) . ? C9 C10 1.367(9) . ? C9 C14 1.482(8) . ? C10 C11 1.436(9) . ? C10 H10 0.9300 . ? C11 N4 1.349(8) . ? C11 C12 1.436(9) . ? C12 C13 1.368(9) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 N4 1.429(8) . ? C15 C16 1.566(9) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.478(10) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 N5 1.123(9) . ? C18 N4 1.466(8) . ? C18 C19 1.489(10) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? N2 N3 1.307(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 C2 C1 C6 118.6(8) . . ? C2 C1 S1 111.3(6) . . ? C6 C1 S1 130.1(7) . . ? N1 C2 C1 115.0(7) . . ? N1 C2 C3 127.3(8) . . ? C1 C2 C3 117.7(8) . . ? C4 C3 C2 125.9(9) . . ? C4 C3 H3 117.0 . . ? C2 C3 H3 117.0 . . ? C5 C4 C3 111.1(10) . . ? C5 C4 H4 124.4 . . ? C3 C4 H4 124.4 . . ? C4 C5 C6 128.9(9) . . ? C4 C5 Cl1 115.3(8) . . ? C6 C5 Cl1 115.8(7) . . ? C5 C6 C1 117.7(8) . . ? C5 C6 Cl2 124.9(8) . . ? C1 C6 Cl2 117.4(8) . . ? N1 C7 N2 120.9(7) . . ? N1 C7 S1 117.8(6) . . ? N2 C7 S1 121.3(7) . . ? N3 C8 C13 124.0(7) . . ? N3 C8 C9 116.7(7) . . ? C13 C8 C9 119.3(8) . . ? C10 C9 C8 118.7(7) . . ? C10 C9 C14 119.4(7) . . ? C8 C9 C14 121.9(7) . . ? C9 C10 C11 123.9(7) . . ? C9 C10 H10 118.1 . . ? C11 C10 H10 118.1 . . ? N4 C11 C10 122.1(7) . . ? N4 C11 C12 122.4(7) . . ? C10 C11 C12 115.5(8) . . ? C13 C12 C11 121.1(7) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C12 C13 C8 121.5(7) . . ? C12 C13 H13 119.3 . . ? C8 C13 H13 119.3 . . ? C9 C14 H14A 109.5 . . ? C9 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C9 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N4 C15 C16 113.9(6) . . ? N4 C15 H15A 108.8 . . ? C16 C15 H15A 108.8 . . ? N4 C15 H15B 108.8 . . ? C16 C15 H15B 108.8 . . ? H15A C15 H15B 107.7 . . ? C17 C16 C15 111.3(6) . . ? C17 C16 H16A 109.4 . . ? C15 C16 H16A 109.4 . . ? C17 C16 H16B 109.4 . . ? C15 C16 H16B 109.4 . . ? H16A C16 H16B 108.0 . . ? N5 C17 C16 178.7(9) . . ? N4 C18 C19 115.5(7) . . ? N4 C18 H18A 108.4 . . ? C19 C18 H18A 108.4 . . ? N4 C18 H18B 108.4 . . ? C19 C18 H18B 108.4 . . ? H18A C18 H18B 107.5 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C7 N1 C2 108.6(7) . . ? N3 N2 C7 109.8(6) . . ? N2 N3 C8 116.4(6) . . ? C11 N4 C15 123.2(6) . . ? C11 N4 C18 120.4(6) . . ? C15 N4 C18 116.4(7) . . ? C1 S1 C7 87.3(4) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.223 _refine_diff_density_min -0.429 _refine_diff_density_rms 0.075 #===END data_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H15 Cl2 N5 S' _chemical_formula_sum 'C18 H15 Cl2 N5 S' _chemical_formula_weight 404.31 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n m a' _symmetry_space_group_name_Hall '-P 2ac 2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 7.421(4) _cell_length_b 12.245(6) _cell_length_c 20.593(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1871.1(16) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 1313 _cell_measurement_theta_min 3.328 _cell_measurement_theta_max 19.577 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.435 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.471 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9457 _exptl_absorpt_correction_T_max 0.9544 _exptl_absorpt_process_details 'SADABS, Bruker(2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(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 'Bruker CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8800 _diffrn_reflns_av_R_equivalents 0.0610 _diffrn_reflns_av_sigmaI/netI 0.0459 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1715 _reflns_number_gt 929 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (BRUKER 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (BRUKER 2000)' _computing_structure_solution 'SHELXTL (BRUKER 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0701P)^2^] 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 1715 _refine_ls_number_parameters 199 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.0876 _refine_ls_R_factor_gt 0.0488 _refine_ls_wR_factor_ref 0.1359 _refine_ls_wR_factor_gt 0.1234 _refine_ls_goodness_of_fit_ref 0.946 _refine_ls_restrained_S_all 0.959 _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 C1 C 1.2454(6) 0.2500 0.57660(17) 0.0675(10) Uani 1 2 d S . . C2 C 1.1571(4) 0.1522(2) 0.55936(13) 0.0753(8) Uani 1 1 d . . . H2 H 1.2116 0.0857 0.5689 0.090 Uiso 1 1 calc RD . . C3 C 0.9937(4) 0.1527(2) 0.52904(13) 0.0735(8) Uani 1 1 d . . . H3 H 0.9380 0.0867 0.5193 0.088 Uiso 1 1 calc R . . C4 C 0.9085(5) 0.2500 0.51239(16) 0.0628(9) Uani 1 2 d S . . C5 C 1.504(2) 0.1427(16) 0.6167(12) 0.082(5) Uani 0.50 1 d P . . H5A H 1.6318 0.1561 0.6210 0.098 Uiso 0.50 1 calc PR . . H5B H 1.4854 0.0967 0.5789 0.098 Uiso 0.50 1 calc PRD . . C6 C 1.434(2) 0.0815(16) 0.6785(10) 0.090(4) Uani 0.50 1 d PU . . H6A H 1.5138 0.0204 0.6874 0.108 Uiso 0.50 1 calc PR . . H6B H 1.3153 0.0524 0.6698 0.108 Uiso 0.50 1 calc PR . . C7 C 1.4250(9) 0.1607(6) 0.7434(4) 0.094(2) Uani 0.50 1 d PU . . C8 C 0.5109(11) 0.1815(9) 0.4329(5) 0.071(3) Uani 0.50 1 d P . . C9 C 0.2410(5) 0.2500 0.38312(15) 0.0635(9) Uani 1 2 d SU . . C10 C 0.2518(9) 0.1461(5) 0.3834(2) 0.0686(13) Uani 0.50 1 d PDU . . C11 C 0.102(2) 0.0922(9) 0.3534(8) 0.138(7) Uani 0.50 1 d PD . . H11 H 0.1052 0.0163 0.3531 0.166 Uiso 0.50 1 calc PR . . C12 C -0.0389(11) 0.1389(7) 0.3261(4) 0.100(2) Uani 0.50 1 d PD . . H12 H -0.1310 0.0985 0.3072 0.120 Uiso 0.50 1 calc PR . . C13 C -0.0408(5) 0.2500 0.32753(18) 0.0744(11) Uani 1 2 d SU . . C14 C 0.0936(9) 0.1893(5) 0.3556(3) 0.0707(13) Uani 0.50 1 d PU . . C15 C 1.498(3) 0.1525(18) 0.6274(12) 0.099(7) Uani 0.50 1 d PD . . H15A H 1.6266 0.1652 0.6319 0.118 Uiso 0.50 1 d PR . . H15B H 1.4835 0.0986 0.5933 0.118 Uiso 0.50 1 d PR . . C16 C 1.421(3) 0.0985(15) 0.6872(10) 0.122(7) Uani 0.50 1 d PD . . H16A H 1.4877 0.0328 0.6950 0.183 Uiso 0.50 1 d PR . . H16B H 1.4388 0.1484 0.7226 0.183 Uiso 0.50 1 d PR . . H16C H 1.2948 0.0813 0.6837 0.183 Uiso 0.50 1 d PR . . Cl1 Cl -0.2253(2) 0.18934(14) 0.29158(7) 0.1085(7) Uani 0.50 1 d P . . Cl2 Cl 0.0864(4) 0.0507(2) 0.35532(17) 0.0904(8) Uani 0.50 1 d P . . N1 N 0.7443(5) 0.2500 0.48059(14) 0.0664(8) Uani 1 2 d S . . N2 N 0.6696(7) 0.1632(3) 0.4643(2) 0.0682(12) Uani 0.50 1 d P . . N3 N 1.4073(5) 0.2500 0.60661(15) 0.0770(9) Uani 1 2 d SD . . N4 N 1.4276(11) 0.2046(5) 0.7917(3) 0.135(3) Uani 0.50 1 d PU . . N5 N 0.4075(7) 0.1017(4) 0.4128(2) 0.0744(13) Uani 0.50 1 d P . . S1 S 0.4278(3) 0.1839(3) 0.41986(13) 0.0651(6) Uani 0.50 1 d P . . 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 C1 0.071(3) 0.077(3) 0.054(2) 0.000 0.009(2) 0.000 C2 0.083(2) 0.0733(19) 0.0696(17) -0.0082(14) -0.0020(17) 0.0156(15) C3 0.085(2) 0.0698(19) 0.0655(17) -0.0096(14) 0.0028(17) 0.0023(16) C4 0.070(3) 0.067(3) 0.052(2) 0.000 0.008(2) 0.000 C5 0.071(9) 0.104(9) 0.071(7) 0.035(8) -0.003(6) -0.010(7) C6 0.088(6) 0.121(9) 0.061(6) -0.001(6) 0.000(5) -0.015(5) C7 0.098(5) 0.111(5) 0.073(4) 0.029(4) -0.006(4) -0.006(4) C8 0.060(6) 0.082(5) 0.071(6) -0.003(4) 0.005(5) -0.004(6) C9 0.065(2) 0.073(2) 0.0518(19) 0.000 0.0075(18) 0.000 C10 0.072(3) 0.073(3) 0.060(3) 0.000(3) 0.014(3) -0.004(3) C11 0.217(16) 0.054(9) 0.145(10) -0.004(7) 0.057(10) -0.029(8) C12 0.103(6) 0.102(6) 0.096(5) 0.019(4) 0.031(5) 0.028(5) C13 0.065(3) 0.104(3) 0.054(2) 0.000 0.0057(19) 0.000 C14 0.070(3) 0.092(4) 0.051(3) 0.001(2) 0.009(3) -0.009(3) C15 0.080(10) 0.135(12) 0.081(10) -0.017(8) 0.000(6) 0.027(8) C16 0.203(15) 0.070(7) 0.093(13) 0.011(7) 0.017(9) -0.013(8) Cl1 0.0790(11) 0.1687(16) 0.0777(10) 0.0031(9) -0.0144(8) -0.0139(9) Cl2 0.1004(15) 0.0712(19) 0.0995(14) 0.0025(12) -0.0219(11) -0.0107(11) N1 0.072(2) 0.071(2) 0.0557(18) 0.000 0.0085(17) 0.000 N2 0.065(3) 0.072(3) 0.068(3) 0.002(2) 0.003(3) 0.005(2) N3 0.066(2) 0.097(3) 0.068(2) 0.000 0.0002(19) 0.000 N4 0.169(6) 0.163(8) 0.074(3) 0.018(4) -0.003(4) -0.014(4) N5 0.084(4) 0.054(3) 0.085(3) 0.001(2) 0.011(3) 0.004(3) S1 0.0724(17) 0.0591(11) 0.0638(12) -0.0008(8) 0.0007(12) -0.0047(14) _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 C1 N3 1.351(5) . ? C1 C2 1.411(3) . ? C1 C2 1.411(3) 7_565 ? C2 C3 1.364(4) . ? C2 H2 0.9300 . ? C3 C4 1.391(3) . ? C3 H3 0.9300 . ? C4 N1 1.383(5) . ? C4 C3 1.391(3) 7_565 ? C5 N3 1.510(17) . ? C5 C6 1.562(19) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C5 H15A 1.0038 . ? C5 H15B 0.7388 . ? C6 C7 1.65(2) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C6 H16A 0.7921 . ? C6 H16B 1.2234 . ? C6 H16C 1.0424 . ? C7 N4 1.133(9) . ? C7 N4 1.927(9) 7_565 ? C7 H16B 0.4652 . ? C8 N5 1.310(10) . ? C8 N2 1.363(9) . ? C8 C8 1.68(2) 7_565 ? C8 S1 1.780(9) 7_565 ? C9 C10 1.275(6) . ? C9 C10 1.275(7) 7_565 ? C9 C14 1.438(7) . ? C9 C14 1.438(7) 7_565 ? C9 S1 1.774(4) 7_565 ? C9 S1 1.774(4) . ? C10 N5 1.413(7) . ? C10 C11 1.430(12) . ? C11 C12 1.320(13) . ? C11 H11 0.9300 . ? C12 C13 1.360(9) . ? C12 H12 0.9300 . ? C13 C12 1.360(9) 7_565 ? C13 C14 1.372(7) 7_565 ? C13 C14 1.372(7) . ? C13 Cl1 1.724(4) . ? C13 Cl1 1.724(4) 7_565 ? C14 C14 1.486(13) 7_565 ? C14 Cl2 1.698(7) . ? C15 N3 1.436(17) . ? C15 C16 1.511(19) . ? C15 H15A 0.9700 . ? C15 H15B 0.9701 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? Cl1 Cl1 1.486(4) 7_565 ? N1 N2 1.245(4) . ? N1 N2 1.245(4) 7_565 ? N3 C15 1.436(17) 7_565 ? N3 C5 1.510(17) 7_565 ? N4 N4 1.111(12) 7_565 ? N4 C7 1.927(9) 7_565 ? S1 S1 1.619(6) 7_565 ? S1 C8 1.780(9) 7_565 ? 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 N3 C1 C2 121.87(19) . . ? N3 C1 C2 121.87(19) . 7_565 ? C2 C1 C2 116.2(4) . 7_565 ? C3 C2 C1 121.6(3) . . ? C3 C2 H2 119.2 . . ? C1 C2 H2 119.2 . . ? C2 C3 C4 121.4(3) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? N1 C4 C3 121.11(19) . 7_565 ? N1 C4 C3 121.11(19) . . ? C3 C4 C3 117.8(4) 7_565 . ? N3 C5 C6 112.0(16) . . ? N3 C5 H5A 109.2 . . ? C6 C5 H5A 109.2 . . ? N3 C5 H5B 109.2 . . ? C6 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? N3 C5 H15A 103.5 . . ? C6 C5 H15A 100.2 . . ? H5B C5 H15A 122.4 . . ? N3 C5 H15B 116.8 . . ? C6 C5 H15B 96.6 . . ? H5A C5 H15B 112.4 . . ? H15A C5 H15B 126.0 . . ? C5 C6 C7 113.0(15) . . ? C5 C6 H6A 109.0 . . ? C7 C6 H6A 109.0 . . ? C5 C6 H6B 109.0 . . ? C7 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? C5 C6 H16A 123.2 . . ? C7 C6 H16A 96.6 . . ? H6B C6 H16A 104.9 . . ? C5 C6 H16B 106.0 . . ? H6A C6 H16B 111.1 . . ? H6B C6 H16B 113.9 . . ? H16A C6 H16B 99.9 . . ? C5 C6 H16C 114.3 . . ? C7 C6 H16C 82.9 . . ? H6A C6 H16C 125.6 . . ? H16A C6 H16C 116.8 . . ? H16B C6 H16C 87.2 . . ? N4 C7 C6 171.7(9) . . ? C6 C7 N4 156.9(7) . 7_565 ? N4 C7 H16B 163.7 . . ? N4 C7 H16B 138.7 7_565 . ? N5 C8 N2 122.2(9) . . ? N5 C8 C8 138.3(5) . 7_565 ? N2 C8 C8 99.5(5) . 7_565 ? N5 C8 S1 116.1(6) . 7_565 ? N2 C8 S1 121.6(7) . 7_565 ? C10 C9 C10 172.8(7) . 7_565 ? C10 C9 C14 62.2(4) . . ? C10 C9 C14 124.4(5) 7_565 . ? C10 C9 C14 124.4(5) . 7_565 ? C10 C9 C14 62.2(4) 7_565 7_565 ? C14 C9 C14 62.2(6) . 7_565 ? C10 C9 S1 113.8(4) . 7_565 ? C10 C9 S1 59.6(3) 7_565 7_565 ? C14 C9 S1 175.9(3) . 7_565 ? C14 C9 S1 121.7(3) 7_565 7_565 ? C10 C9 S1 59.6(3) . . ? C10 C9 S1 113.8(4) 7_565 . ? C14 C9 S1 121.7(3) . . ? C14 C9 S1 175.9(3) 7_565 . ? S1 C9 S1 54.3(2) 7_565 . ? C9 C10 N5 115.9(6) . . ? C9 C10 C11 114.2(7) . . ? N5 C10 C11 129.9(8) . . ? C12 C11 C10 126.9(9) . . ? C12 C11 H11 116.6 . . ? C10 C11 H11 116.6 . . ? C11 C12 C13 115.6(9) . . ? C11 C12 H12 122.2 . . ? C13 C12 H12 122.2 . . ? C12 C13 C12 177.3(6) . 7_565 ? C12 C13 C14 122.9(6) . 7_565 ? C12 C13 C14 57.3(4) 7_565 7_565 ? C12 C13 C14 57.3(4) . . ? C12 C13 C14 122.9(6) 7_565 . ? C14 C13 C14 65.6(6) 7_565 . ? C12 C13 Cl1 64.5(4) . . ? C12 C13 Cl1 115.5(5) 7_565 . ? C14 C13 Cl1 172.6(3) 7_565 . ? C14 C13 Cl1 121.7(3) . . ? C12 C13 Cl1 115.5(5) . 7_565 ? C12 C13 Cl1 64.5(4) 7_565 7_565 ? C14 C13 Cl1 121.7(3) 7_565 7_565 ? C14 C13 Cl1 172.6(3) . 7_565 ? Cl1 C13 Cl1 51.03(17) . 7_565 ? C13 C14 C9 116.0(5) . . ? C13 C14 C14 57.2(3) . 7_565 ? C9 C14 C14 58.9(3) . 7_565 ? C13 C14 Cl2 121.1(4) . . ? C9 C14 Cl2 122.8(5) . . ? C14 C14 Cl2 178.2(3) 7_565 . ? N3 C15 C16 115.3(16) . . ? N3 C15 H15A 110.9 . . ? C16 C15 H15A 111.5 . . ? N3 C15 H15B 107.3 . . ? C16 C15 H15B 104.5 . . ? H15A C15 H15B 106.8 . . ? C15 C16 H16A 107.8 . . ? C15 C16 H16B 106.7 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 113.9 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? Cl1 Cl1 C13 64.48(9) 7_565 . ? N2 N1 N2 117.3(5) . 7_565 ? N2 N1 C4 121.3(3) . . ? N2 N1 C4 121.3(3) 7_565 . ? N1 N2 C8 111.9(6) . . ? C1 N3 C15 123.6(10) . 7_565 ? C1 N3 C15 123.6(10) . . ? C15 N3 C15 112(2) 7_565 . ? C1 N3 C5 118.9(8) . 7_565 ? C15 N3 C5 117.4(5) . 7_565 ? C1 N3 C5 118.9(9) . . ? C15 N3 C5 117.4(5) 7_565 . ? C5 N3 C5 121.0(15) 7_565 . ? N4 N4 C7 118.4(5) 7_565 . ? C7 N4 C7 87.2(6) . 7_565 ? C8 N5 C10 109.1(7) . . ? S1 S1 C9 62.86(11) 7_565 . ? C9 S1 C8 85.0(3) . 7_565 ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.452 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.040 #===END data_4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H20 Cl2 N4 S' _chemical_formula_sum 'C23 H20 Cl2 N4 S' _chemical_formula_weight 455.39 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' 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' _cell_length_a 8.011(5) _cell_length_b 12.238(7) _cell_length_c 22.350(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2191(2) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 1292 _cell_measurement_theta_min 2.568 _cell_measurement_theta_max 20.255 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.380 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 0.410 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9374 _exptl_absorpt_correction_T_max 0.9602 _exptl_absorpt_process_details 'SADABS, Bruker(2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(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 'Bruker CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9130 _diffrn_reflns_av_R_equivalents 0.1154 _diffrn_reflns_av_sigmaI/netI 0.1569 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3838 _reflns_number_gt 1642 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (BRUKER 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (BRUKER 2000)' _computing_structure_solution 'SHELXTL (BRUKER 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0312P)^2^+1.9600P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(15) _refine_ls_number_reflns 3838 _refine_ls_number_parameters 283 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1845 _refine_ls_R_factor_gt 0.0694 _refine_ls_wR_factor_ref 0.1461 _refine_ls_wR_factor_gt 0.1287 _refine_ls_goodness_of_fit_ref 0.909 _refine_ls_restrained_S_all 0.917 _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 C1 C 0.1642(9) 0.3090(6) 0.1581(3) 0.0548(19) Uani 1 1 d . . . C2 C 0.1555(9) 0.2810(6) 0.0979(4) 0.057(2) Uani 1 1 d . . . C3 C 0.0153(10) 0.2264(6) 0.0754(4) 0.067(2) Uani 1 1 d . . . H3 H 0.0100 0.2048 0.0355 0.081 Uiso 1 1 calc R . . C4 C -0.1134(9) 0.2058(6) 0.1139(4) 0.064(2) Uani 1 1 d . . . H4A H -0.2109 0.1696 0.0988 0.077 Uiso 0.619(4) 1 d PR . . C5 C -0.1066(9) 0.2344(6) 0.1738(4) 0.059(2) Uani 1 1 d . . . C6 C 0.0327(10) 0.2882(6) 0.1965(3) 0.0574(19) Uani 1 1 d . . . H6A H 0.0380 0.3094 0.2379 0.069 Uiso 0.381(4) 1 d PR . . C7 C 0.3981(10) 0.3566(6) 0.0999(3) 0.055(2) Uani 1 1 d . . . C8 C 0.7927(9) 0.4896(6) 0.1023(3) 0.0509(19) Uani 1 1 d . . . C9 C 0.8799(9) 0.5456(5) 0.1467(3) 0.0511(19) Uani 1 1 d . . . C10 C 1.0330(9) 0.5889(5) 0.1321(3) 0.057(2) Uani 1 1 d . . . H10 H 1.0925 0.6254 0.1616 0.069 Uiso 1 1 calc R . . C11 C 1.1027(9) 0.5810(6) 0.0760(4) 0.059(2) Uani 1 1 d . . . C12 C 1.0116(9) 0.5293(6) 0.0310(3) 0.066(2) Uani 1 1 d . . . H12 H 1.0542 0.5259 -0.0076 0.079 Uiso 1 1 calc R . . C13 C 0.8579(10) 0.4831(6) 0.0438(3) 0.062(2) Uani 1 1 d . . . H13 H 0.7979 0.4479 0.0138 0.074 Uiso 1 1 calc R . . C14 C 0.8137(10) 0.5545(6) 0.2081(3) 0.085(3) Uani 1 1 d . . . H14A H 0.9042 0.5670 0.2354 0.128 Uiso 1 1 calc R . . H14B H 0.7575 0.4880 0.2186 0.128 Uiso 1 1 calc R . . H14C H 0.7366 0.6144 0.2102 0.128 Uiso 1 1 calc R . . C15 C 1.3481(13) 0.6026(9) 0.0025(5) 0.135(4) Uani 1 1 d U . . H15A H 1.4686 0.6087 0.0053 0.162 Uiso 1 1 calc R . . H15B H 1.3193 0.5317 -0.0138 0.162 Uiso 1 1 calc R . . C16 C 1.2826(13) 0.6847(8) -0.0307(5) 0.136(4) Uani 1 1 d . . . H16A H 1.1642 0.6880 -0.0245 0.204 Uiso 1 1 calc R . . H16B H 1.3051 0.6715 -0.0723 0.204 Uiso 1 1 calc R . . H16C H 1.3322 0.7529 -0.0190 0.204 Uiso 1 1 calc R . . C17 C 1.3687(9) 0.6630(5) 0.1119(4) 0.075(2) Uani 1 1 d . . . H17A H 1.4830 0.6451 0.1015 0.090 Uiso 1 1 calc R . . H17B H 1.3426 0.6251 0.1489 0.090 Uiso 1 1 calc R . . C18 C 1.3586(10) 0.7846(6) 0.1234(3) 0.063(2) Uani 1 1 d . . . C19 C 1.2275(11) 0.8471(7) 0.1042(4) 0.085(3) Uani 1 1 d . . . H19 H 1.1385 0.8166 0.0834 0.102 Uiso 1 1 calc R . . C20 C 1.2330(16) 0.9595(10) 0.1173(5) 0.113(4) Uani 1 1 d . . . H20 H 1.1443 1.0035 0.1054 0.135 Uiso 1 1 calc R . . C21 C 1.360(2) 1.0050(9) 0.1461(5) 0.129(5) Uani 1 1 d . . . H21 H 1.3593 1.0796 0.1539 0.155 Uiso 1 1 calc R . . C22 C 1.4937(17) 0.9430(9) 0.1646(5) 0.125(5) Uani 1 1 d . . . H22 H 1.5841 0.9749 0.1839 0.150 Uiso 1 1 calc R . . C23 C 1.4897(12) 0.8319(7) 0.1536(3) 0.088(3) Uani 1 1 d . . . H23 H 1.5773 0.7883 0.1668 0.105 Uiso 1 1 calc R . . Cl1 Cl -0.2903(7) 0.1408(5) 0.0901(3) 0.086(2) Uani 0.381(4) 1 d P . . Cl2 Cl -0.2735(3) 0.2055(2) 0.21937(10) 0.0932(8) Uani 1 1 d . . . Cl1' Cl 0.0424(4) 0.3312(3) 0.26713(14) 0.0782(14) Uani 0.619(4) 1 d P . . N1 N 0.2995(8) 0.3084(5) 0.0647(3) 0.0658(18) Uani 1 1 d . . . N2 N 0.5532(8) 0.3966(5) 0.0761(3) 0.0683(18) Uani 1 1 d . . . N3 N 0.6378(7) 0.4456(4) 0.1177(3) 0.0572(16) Uani 1 1 d . . . N4 N 1.2617(8) 0.6218(5) 0.0659(3) 0.080(2) Uani 1 1 d U . . S1 S 0.3503(2) 0.37476(16) 0.17434(8) 0.0615(6) 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 C1 0.055(5) 0.040(4) 0.069(5) 0.004(4) -0.016(4) -0.010(4) C2 0.044(5) 0.045(5) 0.081(6) 0.001(4) -0.005(5) 0.005(4) C3 0.060(6) 0.052(5) 0.089(6) -0.003(5) -0.006(5) -0.002(4) C4 0.054(5) 0.035(4) 0.104(7) -0.002(5) -0.003(5) 0.007(4) C5 0.063(5) 0.046(5) 0.069(5) 0.011(4) 0.012(5) -0.006(4) C6 0.057(5) 0.052(5) 0.064(5) 0.004(4) 0.000(4) 0.006(4) C7 0.065(6) 0.044(5) 0.055(5) 0.006(4) -0.010(4) -0.001(4) C8 0.039(5) 0.041(5) 0.073(6) -0.001(4) 0.003(4) -0.005(3) C9 0.062(5) 0.037(4) 0.054(5) 0.005(4) -0.002(4) 0.011(4) C10 0.058(5) 0.043(5) 0.070(6) 0.004(4) -0.011(5) -0.005(4) C11 0.052(5) 0.043(5) 0.082(6) 0.011(4) 0.011(5) 0.000(4) C12 0.058(6) 0.075(6) 0.066(5) -0.013(4) 0.012(4) -0.029(5) C13 0.072(6) 0.050(5) 0.064(6) -0.004(4) 0.002(5) -0.008(4) C14 0.086(7) 0.075(6) 0.094(7) 0.007(5) 0.013(6) -0.016(5) C15 0.091(7) 0.121(9) 0.194(10) 0.065(8) -0.012(7) -0.055(7) C16 0.111(9) 0.079(8) 0.218(13) -0.005(8) -0.012(9) -0.012(7) C17 0.045(5) 0.047(5) 0.132(7) -0.008(5) 0.008(5) -0.014(4) C18 0.066(5) 0.044(5) 0.080(5) 0.000(4) 0.008(5) -0.001(5) C19 0.070(6) 0.060(7) 0.126(8) 0.012(5) 0.003(5) 0.017(5) C20 0.124(10) 0.080(9) 0.134(10) 0.010(8) 0.028(8) 0.034(7) C21 0.215(17) 0.053(7) 0.119(10) 0.005(7) 0.027(11) -0.030(10) C22 0.205(14) 0.054(7) 0.116(8) 0.002(7) -0.047(9) -0.032(8) C23 0.115(8) 0.052(6) 0.096(7) -0.002(5) -0.028(6) -0.010(5) Cl1 0.065(4) 0.085(5) 0.109(5) -0.009(3) 0.004(3) -0.024(3) Cl2 0.0667(15) 0.0968(18) 0.1161(18) 0.0096(15) 0.0142(14) -0.0153(13) Cl1' 0.093(3) 0.077(3) 0.065(2) -0.0028(18) 0.010(2) -0.0058(19) N1 0.062(5) 0.063(4) 0.073(4) -0.005(4) -0.001(4) 0.002(4) N2 0.067(5) 0.057(4) 0.081(5) 0.001(4) -0.001(4) -0.008(4) N3 0.054(4) 0.039(3) 0.078(4) 0.004(3) -0.015(4) 0.000(3) N4 0.064(5) 0.068(4) 0.109(5) -0.002(4) 0.017(4) -0.031(4) S1 0.0606(12) 0.0559(12) 0.0681(13) -0.0018(11) -0.0077(11) -0.0046(11) _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 C1 C6 1.383(9) . ? C1 C2 1.392(9) . ? C1 S1 1.732(7) . ? C2 C3 1.399(10) . ? C2 N1 1.412(9) . ? C3 C4 1.367(9) . ? C3 H3 0.9300 . ? C4 C5 1.384(10) . ? C4 Cl1 1.710(9) . ? C4 H4A 0.9599 . ? C5 C6 1.392(9) . ? C5 Cl2 1.718(7) . ? C6 Cl1' 1.665(8) . ? C6 H6A 0.9600 . ? C7 N1 1.261(8) . ? C7 N2 1.437(9) . ? C7 S1 1.722(7) . ? C8 C9 1.394(9) . ? C8 N3 1.396(8) . ? C8 C13 1.410(9) . ? C9 C10 1.376(9) . ? C9 C14 1.475(9) . ? C10 C11 1.375(9) . ? C10 H10 0.9300 . ? C11 N4 1.386(9) . ? C11 C12 1.393(9) . ? C12 C13 1.384(9) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.356(11) . ? C15 N4 1.594(12) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 N4 1.431(9) . ? C17 C18 1.512(9) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.368(10) . ? C18 C23 1.376(10) . ? C19 C20 1.406(12) . ? C19 H19 0.9300 . ? C20 C21 1.329(14) . ? C20 H20 0.9300 . ? C21 C22 1.373(15) . ? C21 H21 0.9300 . ? C22 C23 1.382(12) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? Cl1 H4A 0.7525 . ? Cl1' H6A 0.7073 . ? N2 N3 1.297(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 C6 C1 C2 121.2(7) . . ? C6 C1 S1 127.7(6) . . ? C2 C1 S1 111.1(6) . . ? C1 C2 C3 120.3(8) . . ? C1 C2 N1 114.1(7) . . ? C3 C2 N1 125.5(8) . . ? C4 C3 C2 117.9(7) . . ? C4 C3 H3 121.1 . . ? C2 C3 H3 121.1 . . ? C3 C4 C5 122.2(7) . . ? C3 C4 Cl1 121.0(7) . . ? C5 C4 Cl1 116.8(7) . . ? C3 C4 H4A 118.5 . . ? C5 C4 H4A 119.3 . . ? C4 C5 C6 120.3(7) . . ? C4 C5 Cl2 119.4(6) . . ? C6 C5 Cl2 120.3(7) . . ? C1 C6 C5 118.1(7) . . ? C1 C6 Cl1' 119.6(6) . . ? C5 C6 Cl1' 122.2(7) . . ? C1 C6 H6A 120.9 . . ? C5 C6 H6A 121.0 . . ? N1 C7 N2 118.0(6) . . ? N1 C7 S1 121.6(6) . . ? N2 C7 S1 120.4(6) . . ? C9 C8 N3 117.3(7) . . ? C9 C8 C13 120.1(6) . . ? N3 C8 C13 122.5(7) . . ? C10 C9 C8 117.8(7) . . ? C10 C9 C14 120.9(7) . . ? C8 C9 C14 121.3(7) . . ? C11 C10 C9 123.5(7) . . ? C11 C10 H10 118.3 . . ? C9 C10 H10 118.3 . . ? C10 C11 N4 119.7(7) . . ? C10 C11 C12 118.4(7) . . ? N4 C11 C12 121.8(7) . . ? C13 C12 C11 120.2(7) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C13 C8 119.8(7) . . ? C12 C13 H13 120.1 . . ? C8 C13 H13 120.1 . . ? C9 C14 H14A 109.5 . . ? C9 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C9 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 N4 102.1(11) . . ? C16 C15 H15A 111.3 . . ? N4 C15 H15A 111.3 . . ? C16 C15 H15B 111.3 . . ? N4 C15 H15B 111.3 . . ? H15A C15 H15B 109.2 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N4 C17 C18 115.9(7) . . ? N4 C17 H17A 108.3 . . ? C18 C17 H17A 108.3 . . ? N4 C17 H17B 108.3 . . ? C18 C17 H17B 108.3 . . ? H17A C17 H17B 107.4 . . ? C19 C18 C23 120.3(8) . . ? C19 C18 C17 122.6(8) . . ? C23 C18 C17 117.1(8) . . ? C18 C19 C20 117.3(9) . . ? C18 C19 H19 121.4 . . ? C20 C19 H19 121.4 . . ? C21 C20 C19 122.3(12) . . ? C21 C20 H20 118.9 . . ? C19 C20 H20 118.9 . . ? C20 C21 C22 120.8(11) . . ? C20 C21 H21 119.6 . . ? C22 C21 H21 119.6 . . ? C21 C22 C23 118.2(11) . . ? C21 C22 H22 120.9 . . ? C23 C22 H22 120.9 . . ? C18 C23 C22 121.2(10) . . ? C18 C23 H23 119.4 . . ? C22 C23 H23 119.4 . . ? C7 N1 C2 107.2(6) . . ? N3 N2 C7 110.1(6) . . ? N2 N3 C8 117.8(6) . . ? C11 N4 C17 124.1(7) . . ? C11 N4 C15 119.4(7) . . ? C17 N4 C15 115.5(6) . . ? C7 S1 C1 86.0(4) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.291 _refine_diff_density_min -0.359 _refine_diff_density_rms 0.063 #===END