data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name B.Patel _publ_contact_author_email patel@iitg.ernet.in loop_ _publ_author_name B.Patel N.Khatun S.Rout R.Yella data_15c _database_code_depnum_ccdc_archive 'CCDC 787035' #TrackingRef '15d To be Refined once.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H10 Cl2 N4 S' _chemical_formula_weight 337.23 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' Cl Cl 0.1484 0.1585 '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 Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_hall_group '-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 29.6523(10) _cell_length_b 17.5907(10) _cell_length_c 17.3440(7) _cell_angle_alpha 90.00 _cell_angle_beta 108.649(3) _cell_angle_gamma 90.00 _cell_volume 8571.7(7) _cell_formula_units_Z 24 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4785 _cell_measurement_theta_min 3.25 _cell_measurement_theta_max 27.18 _exptl_crystal_description rod _exptl_crystal_colour blue _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 1.568 _exptl_crystal_density_diffrn 1.568 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4128 _exptl_absorpt_coefficient_mu 0.597 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.836 _exptl_absorpt_correction_T_max 0.887 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32738 _diffrn_reflns_av_R_equivalents 0.0276 _diffrn_reflns_av_sigmaI/netI 0.0317 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.37 _diffrn_reflns_theta_max 27.53 _reflns_number_total 9883 _reflns_number_gt 2429 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^ > 2\s(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^)+(0.0604P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8512 _refine_ls_number_parameters 568 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1132 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.1412 _refine_ls_wR_factor_gt 0.1011 _refine_ls_goodness_of_fit_ref 0.947 _refine_ls_restrained_S_all 0.947 _refine_ls_shift/su_max 1.045 _refine_ls_shift/su_mean 0.218 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 S1 S 0.04370(5) 0.34821(7) 0.43818(9) 0.0371(4) Uani 1 1 d . . . Cl8 Cl 0.22250(6) 0.36338(10) 0.60235(11) 0.0657(6) Uani 1 1 d . . . Cl9 Cl -0.19163(5) 0.30540(9) 0.12964(11) 0.0597(5) Uani 1 1 d . . . C15 C -0.0743(2) 0.4778(3) 0.2020(4) 0.0371(16) Uani 1 1 d . . . H15 H -0.0505 0.5145 0.2171 0.045 Uiso 1 1 calc R . . C14 C -0.0702(2) 0.4114(3) 0.2477(4) 0.0345(16) Uani 1 1 d . . . C13 C -0.10552(19) 0.3561(3) 0.2244(3) 0.0369(16) Uani 1 1 d . . . H13 H -0.1028 0.3108 0.2532 0.044 Uiso 1 1 calc R . . C17 C -0.1450(2) 0.3705(3) 0.1567(4) 0.0402(16) Uani 1 1 d . . . C16 C -0.1494(2) 0.4354(3) 0.1110(4) 0.0472(18) Uani 1 1 d . . . H16 H -0.1759 0.4430 0.0654 0.057 Uiso 1 1 calc R . . C18 C -0.1138(2) 0.4888(3) 0.1342(4) 0.0439(17) Uani 1 1 d . . . H18 H -0.1163 0.5331 0.1038 0.053 Uiso 1 1 calc R . . C19 C 0.11096(19) 0.2254(3) 0.5721(3) 0.0333(15) Uani 1 1 d . . . C23 C 0.1406(2) 0.2828(3) 0.5601(3) 0.0404(16) Uani 1 1 d . . . H23 H 0.1305 0.3145 0.5149 0.048 Uiso 1 1 calc R . . C22 C 0.1857(2) 0.2914(3) 0.6178(4) 0.0430(17) Uani 1 1 d . . . C20 C 0.1284(2) 0.1764(3) 0.6394(3) 0.0391(16) Uani 1 1 d . . . H20 H 0.1096 0.1364 0.6466 0.047 Uiso 1 1 calc R . . C21 C 0.2020(2) 0.2446(3) 0.6842(3) 0.0477(18) Uani 1 1 d . . . H21 H 0.2321 0.2517 0.7216 0.057 Uiso 1 1 calc R . . C24 C 0.1733(2) 0.1874(3) 0.6947(4) 0.0481(17) Uani 1 1 d . . . H24 H 0.1841 0.1554 0.7396 0.058 Uiso 1 1 calc R . . C39 C -0.01211(19) 0.3413(3) 0.3622(3) 0.0306(15) Uani 1 1 d . . . C40 C 0.0360(2) 0.2530(3) 0.4576(3) 0.0325(15) Uani 1 1 d . . . N8 N 0.06509(15) 0.2116(2) 0.5197(3) 0.0400(13) Uani 1 1 d . . . H8A H 0.0531 0.1692 0.5283 0.048 Uiso 1 1 calc R . . N5 N -0.03001(16) 0.4046(2) 0.3174(3) 0.0390(14) Uani 1 1 d . . . H5A H -0.0146 0.4461 0.3340 0.047 Uiso 1 1 calc R . . N6 N -0.03182(15) 0.2752(2) 0.3555(3) 0.0401(14) Uani 1 1 d . . . N7 N -0.00325(15) 0.2230(2) 0.4102(3) 0.0403(14) Uani 1 1 d . . . S2 S 0.04372(5) 0.31843(8) 0.93809(9) 0.0377(4) Uani 1 1 d . . . Cl5 Cl 0.22250(6) 0.30336(10) 1.10239(10) 0.0637(5) Uani 1 1 d . . . Cl7 Cl -0.19166(5) 0.36104(9) 0.62975(11) 0.0585(5) Uani 1 1 d . . . C27 C -0.0741(2) 0.1893(3) 0.7023(3) 0.0406(16) Uani 1 1 d . . . H27 H -0.0499 0.1532 0.7175 0.049 Uiso 1 1 calc R . . C28 C -0.0705(2) 0.2560(3) 0.7478(3) 0.0335(15) Uani 1 1 d . . . C29 C -0.10633(19) 0.3101(3) 0.7238(3) 0.0380(16) Uani 1 1 d . . . H29 H -0.1044 0.3551 0.7529 0.046 Uiso 1 1 calc R . . C26 C -0.1490(2) 0.2306(3) 0.6100(3) 0.0449(17) Uani 1 1 d . . . H26 H -0.1750 0.2228 0.5636 0.054 Uiso 1 1 calc R . . C25 C -0.1452(2) 0.2955(3) 0.6551(3) 0.0404(16) Uani 1 1 d . . . C30 C -0.1133(2) 0.1772(3) 0.6350(4) 0.0444(17) Uani 1 1 d . . . H30 H -0.1158 0.1321 0.6059 0.053 Uiso 1 1 calc R . . C31 C 0.1118(2) 0.4412(3) 1.0725(3) 0.0348(16) Uani 1 1 d . . . C32 C 0.1409(2) 0.3837(3) 1.0607(3) 0.0369(15) Uani 1 1 d . . . H32 H 0.1306 0.3518 1.0158 0.044 Uiso 1 1 calc R . . C33 C 0.1857(2) 0.3748(3) 1.1171(4) 0.0415(16) Uani 1 1 d . . . C36 C 0.1286(2) 0.4901(3) 1.1393(4) 0.0429(18) Uani 1 1 d . . . H36 H 0.1098 0.5300 1.1466 0.051 Uiso 1 1 calc R . . C35 C 0.1731(2) 0.4784(4) 1.1939(4) 0.053(2) Uani 1 1 d . . . H35 H 0.1837 0.5099 1.2392 0.063 Uiso 1 1 calc R . . C34 C 0.2023(2) 0.4221(3) 1.1840(4) 0.0508(19) Uani 1 1 d . . . H34 H 0.2326 0.4157 1.2212 0.061 Uiso 1 1 calc R . . C41 C -0.01214(19) 0.3248(3) 0.8629(3) 0.0314(14) Uani 1 1 d . . . C42 C 0.0365(2) 0.4140(3) 0.9583(3) 0.0315(15) Uani 1 1 d . . . N10 N 0.06543(16) 0.4556(2) 1.0205(3) 0.0401(14) Uani 1 1 d . . . H10A H 0.0534 0.4977 1.0296 0.048 Uiso 1 1 calc R . . N9 N -0.02997(15) 0.2618(2) 0.8170(3) 0.0376(13) Uani 1 1 d . . . H9 H -0.0143 0.2204 0.8325 0.045 Uiso 1 1 calc R . . N11 N -0.00328(16) 0.4435(2) 0.9099(3) 0.0400(14) Uani 1 1 d . . . N12 N -0.03173(16) 0.3910(2) 0.8551(3) 0.0375(13) Uani 1 1 d . . . S3 S 0.04366(5) 1.01505(8) 0.43808(9) 0.0377(4) Uani 1 1 d . . . Cl4 Cl 0.22238(6) 1.03011(10) 0.60229(11) 0.0654(6) Uani 1 1 d . . . Cl6 Cl -0.19160(5) 0.97210(9) 0.12969(11) 0.0584(6) Uani 1 1 d . . . C1 C -0.1492(2) 1.1031(3) 0.1097(4) 0.0435(18) Uani 1 1 d . . . H1 H -0.1754 1.1110 0.0637 0.052 Uiso 1 1 calc R . . C3 C -0.0744(2) 1.1449(3) 0.2017(3) 0.0365(15) Uani 1 1 d . . . H3 H -0.0508 1.1819 0.2173 0.044 Uiso 1 1 calc R . . C4 C -0.07023(19) 1.0786(3) 0.2468(3) 0.0334(15) Uani 1 1 d . . . C5 C -0.10612(19) 1.0237(3) 0.2235(4) 0.0371(16) Uani 1 1 d . . . H5 H -0.1039 0.9787 0.2527 0.045 Uiso 1 1 calc R . . C2 C -0.1135(2) 1.1559(3) 0.1337(4) 0.0430(17) Uani 1 1 d . . . H2 H -0.1157 1.2003 0.1035 0.052 Uiso 1 1 calc R . . C6 C -0.1451(2) 1.0382(3) 0.1554(4) 0.0433(17) Uani 1 1 d . . . C7 C 0.1118(2) 0.8923(3) 0.5715(3) 0.0362(16) Uani 1 1 d . . . C8 C 0.14068(19) 0.9495(3) 0.5603(3) 0.0395(17) Uani 1 1 d . . . H8 H 0.1302 0.9818 0.5156 0.047 Uiso 1 1 calc R . . C9 C 0.1856(2) 0.9581(3) 0.6166(4) 0.0424(17) Uani 1 1 d . . . C12 C 0.1285(2) 0.8443(3) 0.6380(4) 0.0434(17) Uani 1 1 d . . . H12 H 0.1094 0.8048 0.6453 0.052 Uiso 1 1 calc R . . C11 C 0.1735(2) 0.8547(3) 0.6939(4) 0.0504(19) Uani 1 1 d . . . H11 H 0.1842 0.8224 0.7386 0.060 Uiso 1 1 calc R . . C10 C 0.2023(2) 0.9123(3) 0.6837(4) 0.0515(19) Uani 1 1 d . . . H10 H 0.2323 0.9201 0.7213 0.062 Uiso 1 1 calc R . . C37 C -0.0121(2) 1.0093(3) 0.3625(3) 0.0335(15) Uani 1 1 d . . . C38 C 0.03593(19) 0.9203(3) 0.4579(3) 0.0318(15) Uani 1 1 d . . . N4 N 0.06536(16) 0.8780(2) 0.5199(3) 0.0384(13) Uani 1 1 d . . . H4 H 0.0534 0.8356 0.5288 0.046 Uiso 1 1 calc R . . N1 N -0.03007(16) 1.0722(2) 0.3172(3) 0.0406(14) Uani 1 1 d . . . H1A H -0.0148 1.1137 0.3338 0.049 Uiso 1 1 calc R . . N2 N -0.03156(16) 0.9426(2) 0.3551(3) 0.0408(14) Uani 1 1 d . . . N3 N -0.00310(16) 0.8900(2) 0.4095(3) 0.0412(14) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0333(10) 0.0310(8) 0.0403(9) 0.0023(7) 0.0025(7) -0.0097(7) Cl8 0.0441(11) 0.0768(12) 0.0637(12) 0.0061(9) -0.0004(9) -0.0254(10) Cl9 0.0384(11) 0.0530(10) 0.0724(12) 0.0011(9) -0.0037(9) -0.0073(8) C15 0.040(4) 0.022(3) 0.054(4) -0.002(3) 0.021(3) 0.002(3) C14 0.038(4) 0.023(3) 0.042(3) -0.005(2) 0.013(3) 0.001(3) C13 0.036(4) 0.032(3) 0.036(3) 0.000(3) 0.002(3) 0.006(3) C17 0.038(4) 0.034(3) 0.049(4) -0.001(3) 0.015(3) 0.001(3) C16 0.032(4) 0.058(4) 0.046(4) 0.003(3) 0.004(3) 0.005(3) C18 0.039(4) 0.047(4) 0.050(4) 0.010(3) 0.019(3) 0.016(3) C19 0.030(4) 0.032(3) 0.038(3) -0.001(3) 0.011(3) -0.006(3) C23 0.041(4) 0.044(4) 0.031(3) 0.003(3) 0.004(3) -0.001(3) C22 0.030(4) 0.047(3) 0.046(4) -0.006(3) 0.002(3) -0.009(3) C20 0.034(4) 0.039(3) 0.044(4) 0.009(3) 0.011(3) 0.001(3) C21 0.032(4) 0.073(4) 0.031(3) 0.009(3) 0.000(3) 0.006(4) C24 0.035(4) 0.064(4) 0.045(4) 0.020(3) 0.012(3) 0.001(3) C39 0.028(4) 0.037(3) 0.024(3) -0.003(2) 0.004(2) -0.002(3) C40 0.027(4) 0.036(3) 0.033(3) -0.001(3) 0.008(3) -0.010(3) N8 0.030(3) 0.040(3) 0.042(3) 0.004(2) 0.001(2) -0.012(2) N5 0.040(3) 0.027(2) 0.040(3) 0.000(2) -0.001(2) -0.006(2) N6 0.033(3) 0.027(3) 0.047(3) 0.002(2) -0.005(2) -0.011(2) N7 0.037(3) 0.031(3) 0.041(3) 0.003(2) -0.004(2) -0.002(2) S2 0.0318(10) 0.0314(8) 0.0428(9) -0.0016(7) 0.0018(7) 0.0085(7) Cl5 0.0405(11) 0.0783(12) 0.0617(11) -0.0040(9) 0.0012(9) 0.0235(9) Cl7 0.0374(11) 0.0537(10) 0.0714(12) -0.0017(9) -0.0009(9) 0.0056(8) C27 0.029(4) 0.045(4) 0.047(4) 0.001(3) 0.010(3) -0.003(3) C28 0.035(4) 0.029(3) 0.034(3) -0.004(3) 0.008(3) -0.007(3) C29 0.040(4) 0.031(3) 0.044(3) -0.003(3) 0.015(3) 0.003(3) C26 0.042(4) 0.045(4) 0.041(4) -0.008(3) 0.005(3) -0.017(3) C25 0.029(4) 0.041(3) 0.041(3) 0.001(3) -0.002(3) -0.007(3) C30 0.047(4) 0.035(3) 0.049(4) -0.010(3) 0.014(3) -0.009(3) C31 0.025(4) 0.041(3) 0.037(3) 0.006(3) 0.007(3) -0.005(3) C32 0.031(4) 0.043(4) 0.035(3) -0.005(3) 0.008(3) 0.001(3) C33 0.029(4) 0.050(4) 0.044(4) 0.000(3) 0.010(3) 0.000(3) C36 0.038(4) 0.042(4) 0.046(4) -0.014(3) 0.010(3) -0.006(3) C35 0.039(5) 0.065(5) 0.047(4) -0.013(3) 0.004(3) -0.013(4) C34 0.024(4) 0.069(5) 0.051(4) -0.006(3) 0.001(3) -0.008(4) C41 0.033(4) 0.024(3) 0.036(3) -0.003(2) 0.011(3) 0.003(3) C42 0.031(4) 0.030(3) 0.033(3) 0.003(2) 0.009(3) 0.006(3) N10 0.034(3) 0.037(3) 0.040(3) -0.010(2) -0.001(2) 0.007(2) N9 0.032(3) 0.029(2) 0.046(3) -0.004(2) 0.005(2) 0.010(2) N11 0.036(3) 0.032(3) 0.042(3) -0.002(2) -0.001(3) 0.005(2) N12 0.038(3) 0.028(2) 0.040(3) -0.004(2) 0.003(2) 0.003(2) S3 0.0331(10) 0.0339(8) 0.0396(9) 0.0015(7) 0.0027(7) -0.0109(7) Cl4 0.0419(12) 0.0776(12) 0.0645(12) 0.0047(10) -0.0003(9) -0.0261(10) Cl6 0.0373(12) 0.0549(10) 0.0697(12) 0.0003(9) -0.0018(9) -0.0058(8) C1 0.048(4) 0.040(3) 0.037(3) 0.004(3) 0.007(3) 0.012(3) C3 0.046(4) 0.030(3) 0.037(3) 0.006(3) 0.018(3) -0.004(3) C4 0.026(4) 0.045(3) 0.030(3) -0.003(3) 0.010(3) 0.003(3) C5 0.033(4) 0.033(3) 0.042(4) 0.003(3) 0.008(3) -0.002(3) C2 0.054(4) 0.037(3) 0.041(4) 0.009(3) 0.020(3) 0.007(3) C6 0.036(4) 0.045(4) 0.047(4) -0.010(3) 0.012(3) 0.001(3) C7 0.035(4) 0.042(3) 0.024(3) -0.001(3) -0.001(3) 0.001(3) C8 0.028(4) 0.045(4) 0.039(4) 0.000(3) 0.001(3) -0.012(3) C9 0.036(4) 0.056(4) 0.033(3) -0.002(3) 0.007(3) -0.007(3) C12 0.032(4) 0.052(4) 0.046(4) 0.001(3) 0.011(3) -0.002(3) C11 0.037(4) 0.064(4) 0.042(4) 0.012(3) 0.002(3) 0.013(4) C10 0.030(4) 0.073(5) 0.043(4) -0.006(3) 0.001(3) -0.004(4) C37 0.030(4) 0.034(3) 0.036(3) -0.006(3) 0.010(3) -0.012(3) C38 0.034(4) 0.028(3) 0.030(3) -0.001(2) 0.006(3) -0.006(3) N4 0.037(3) 0.029(3) 0.044(3) 0.005(2) 0.005(2) -0.012(2) N1 0.042(3) 0.029(3) 0.044(3) 0.002(2) 0.003(3) -0.006(2) N2 0.040(3) 0.035(3) 0.037(3) 0.000(2) -0.003(2) -0.004(3) N3 0.040(3) 0.031(3) 0.041(3) 0.004(2) -0.003(2) -0.012(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 S1 C40 1.738(5) . ? S1 C39 1.759(5) . ? Cl8 C22 1.747(6) . ? Cl9 C17 1.741(6) . ? C15 C18 1.383(7) . ? C15 C14 1.394(7) . ? C14 C13 1.392(7) . ? C14 N5 1.405(6) . ? C13 C17 1.391(7) . ? C17 C16 1.371(7) . ? C16 C18 1.374(7) . ? C19 C23 1.396(7) . ? C19 N8 1.395(6) . ? C19 C20 1.409(7) . ? C23 C22 1.401(7) . ? C22 C21 1.371(7) . ? C20 C24 1.384(7) . ? C21 C24 1.367(7) . ? C39 N6 1.290(6) . ? C39 N5 1.365(6) . ? C40 N7 1.301(6) . ? C40 N8 1.357(6) . ? N6 N7 1.396(5) . ? S2 C42 1.745(5) . ? S2 C41 1.753(5) . ? Cl5 C33 1.735(6) . ? Cl7 C25 1.741(6) . ? C27 C30 1.376(7) . ? C27 C28 1.398(7) . ? C28 C29 1.388(7) . ? C28 N9 1.405(6) . ? C29 C25 1.391(7) . ? C26 C25 1.368(7) . ? C26 C30 1.378(7) . ? C31 C32 1.387(7) . ? C31 C36 1.401(7) . ? C31 N10 1.405(6) . ? C32 C33 1.383(7) . ? C33 C34 1.385(7) . ? C36 C35 1.372(7) . ? C35 C34 1.361(8) . ? C41 N12 1.288(6) . ? C41 N9 1.369(6) . ? C42 N11 1.316(6) . ? C42 N10 1.357(6) . ? N11 N12 1.398(5) . ? S3 C38 1.731(5) . ? S3 C37 1.753(5) . ? Cl4 C9 1.740(6) . ? Cl6 C6 1.749(6) . ? C1 C2 1.369(7) . ? C1 C6 1.375(7) . ? C3 C2 1.377(7) . ? C3 C4 1.388(7) . ? C4 C5 1.398(7) . ? C4 N1 1.411(6) . ? C5 C6 1.386(7) . ? C7 C8 1.375(7) . ? C7 C12 1.387(7) . ? C7 N4 1.405(6) . ? C8 C9 1.385(7) . ? C9 C10 1.371(8) . ? C12 C11 1.388(7) . ? C11 C10 1.373(7) . ? C37 N2 1.295(6) . ? C37 N1 1.363(6) . ? C38 N3 1.306(6) . ? C38 N4 1.368(6) . ? N2 N3 1.395(5) . ? 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 C40 S1 C39 85.9(3) . . ? C18 C15 C14 119.8(5) . . ? C15 C14 C13 120.0(5) . . ? C15 C14 N5 117.1(5) . . ? C13 C14 N5 122.9(5) . . ? C17 C13 C14 118.0(5) . . ? C16 C17 C13 122.6(5) . . ? C16 C17 Cl9 118.1(5) . . ? C13 C17 Cl9 119.2(4) . . ? C18 C16 C17 118.6(5) . . ? C16 C18 C15 121.0(6) . . ? C23 C19 N8 123.9(5) . . ? C23 C19 C20 119.0(5) . . ? N8 C19 C20 117.1(5) . . ? C19 C23 C22 118.3(5) . . ? C21 C22 C23 122.3(6) . . ? C21 C22 Cl8 119.7(5) . . ? C23 C22 Cl8 118.0(5) . . ? C24 C20 C19 120.4(5) . . ? C22 C21 C24 119.2(5) . . ? C21 C24 C20 120.8(5) . . ? N6 C39 N5 127.0(4) . . ? N6 C39 S1 114.8(4) . . ? N5 C39 S1 118.2(4) . . ? N7 C40 N8 119.8(5) . . ? N7 C40 S1 114.5(4) . . ? N8 C40 S1 125.5(4) . . ? C40 N8 C19 131.6(5) . . ? C39 N5 C14 128.9(4) . . ? C39 N6 N7 111.9(4) . . ? C40 N7 N6 112.9(4) . . ? C42 S2 C41 86.6(2) . . ? C30 C27 C28 120.0(6) . . ? C29 C28 C27 119.6(5) . . ? C29 C28 N9 124.7(5) . . ? C27 C28 N9 115.7(5) . . ? C25 C29 C28 118.3(5) . . ? C25 C26 C30 118.4(5) . . ? C26 C25 C29 122.6(5) . . ? C26 C25 Cl7 119.6(4) . . ? C29 C25 Cl7 117.8(4) . . ? C26 C30 C27 121.1(6) . . ? C32 C31 C36 119.7(5) . . ? C32 C31 N10 124.4(5) . . ? C36 C31 N10 115.9(5) . . ? C33 C32 C31 118.8(5) . . ? C32 C33 C34 121.8(6) . . ? C32 C33 Cl5 119.0(5) . . ? C34 C33 Cl5 119.2(5) . . ? C35 C36 C31 119.2(6) . . ? C34 C35 C36 122.1(6) . . ? C35 C34 C33 118.3(6) . . ? N12 C41 N9 126.3(5) . . ? N12 C41 S2 115.1(4) . . ? N9 C41 S2 118.5(4) . . ? N11 C42 N10 120.3(5) . . ? N11 C42 S2 113.2(4) . . ? N10 C42 S2 126.3(4) . . ? C42 N10 C31 130.8(5) . . ? C41 N9 C28 128.5(4) . . ? C42 N11 N12 113.4(4) . . ? C41 N12 N11 111.8(4) . . ? C38 S3 C37 86.5(3) . . ? C2 C1 C6 118.2(6) . . ? C2 C3 C4 120.0(5) . . ? C3 C4 C5 119.6(5) . . ? C3 C4 N1 117.0(5) . . ? C5 C4 N1 123.3(5) . . ? C6 C5 C4 118.0(5) . . ? C1 C2 C3 121.5(5) . . ? C1 C6 C5 122.7(6) . . ? C1 C6 Cl6 119.3(5) . . ? C5 C6 Cl6 118.0(5) . . ? C8 C7 C12 119.4(5) . . ? C8 C7 N4 124.7(5) . . ? C12 C7 N4 116.0(5) . . ? C7 C8 C9 118.9(5) . . ? C10 C9 C8 122.6(6) . . ? C10 C9 Cl4 118.4(5) . . ? C8 C9 Cl4 119.0(5) . . ? C11 C12 C7 120.6(6) . . ? C10 C11 C12 120.4(6) . . ? C9 C10 C11 118.2(6) . . ? N2 C37 N1 126.7(5) . . ? N2 C37 S3 114.2(4) . . ? N1 C37 S3 119.0(4) . . ? N3 C38 N4 119.7(5) . . ? N3 C38 S3 114.3(4) . . ? N4 C38 S3 126.0(4) . . ? C38 N4 C7 130.8(5) . . ? C37 N1 C4 129.1(5) . . ? C37 N2 N3 112.2(4) . . ? C38 N3 N2 112.6(4) . . ? _diffrn_measured_fraction_theta_max 0.861 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.861 _refine_diff_density_max 0.208 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.039 data_3b _database_code_depnum_ccdc_archive 'CCDC 787036' #TrackingRef '3b-7b-9b-17b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H6 Cl N5' _chemical_formula_sum 'C7 H6 Cl N5' _chemical_formula_weight 195.62 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' 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 P21/c _symmetry_space_group_name_Hall '-P 2ybc' 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 10.7905(4) _cell_length_b 7.4830(3) _cell_length_c 11.7242(4) _cell_angle_alpha 90.00 _cell_angle_beta 108.708(2) _cell_angle_gamma 90.00 _cell_volume 896.66(6) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4771 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 28.290 _exptl_crystal_description Plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas 1.449 _exptl_crystal_density_diffrn 1.449 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.384 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.851 _exptl_absorpt_correction_T_max 0.908 _exptl_absorpt_process_details multi-scan _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9085 _diffrn_reflns_av_R_equivalents 0.0554 _diffrn_reflns_av_sigmaI/netI 0.0280 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 28.35 _reflns_number_total 2232 _reflns_number_gt 1490 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.1500P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2123 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0726 _refine_ls_R_factor_gt 0.0547 _refine_ls_wR_factor_ref 0.2112 _refine_ls_wR_factor_gt 0.1932 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 0.08052(9) 0.17463(11) 0.05983(9) 0.1119(5) Uani 1 1 d . . . N1 N 0.29927(17) 0.3603(2) 0.00226(13) 0.0447(4) Uani 1 1 d . . . C1 C 0.24822(18) 0.4486(2) 0.08529(16) 0.0434(5) Uani 1 1 d . . . C7 C 0.37668(19) 0.2154(3) 0.01635(14) 0.0434(5) Uani 1 1 d . . . N2 N 0.2890(2) 0.4364(3) -0.10681(15) 0.0621(6) Uani 1 1 d . . . N4 N 0.41343(18) 0.1982(2) -0.08126(14) 0.0541(5) Uani 1 1 d . . . N3 N 0.3566(2) 0.3370(3) -0.15340(16) 0.0641(6) Uani 1 1 d . . . C2 C 0.1489(2) 0.3734(3) 0.1201(2) 0.0621(6) Uani 1 1 d . . . C6 C 0.2999(2) 0.6101(3) 0.1323(2) 0.0633(6) Uani 1 1 d . . . H5 H 0.3649 0.6626 0.1072 0.076 Uiso 1 1 calc R . . C3 C 0.1065(3) 0.4601(4) 0.2051(3) 0.0860(9) Uani 1 1 d . . . H8 H 0.0397 0.4106 0.2290 0.103 Uiso 1 1 calc R . . C4 C 0.1624(3) 0.6185(4) 0.2544(3) 0.0876(9) Uani 1 1 d . . . H7 H 0.1360 0.6736 0.3138 0.105 Uiso 1 1 calc R . . C5 C 0.2566(3) 0.6950(3) 0.2162(3) 0.0823(9) Uani 1 1 d . . . H6 H 0.2916 0.8051 0.2471 0.099 Uiso 1 1 calc R . . N5 N 0.4106(2) 0.1082(3) 0.11108(15) 0.0670(6) Uani 1 1 d . . . H3A H 0.4607 0.0180 0.1130 0.080 Uiso 1 1 calc R . . H3B H 0.3826 0.1286 0.1707 0.080 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 0.1143(8) 0.0995(8) 0.1485(8) -0.0557(5) 0.0790(6) -0.0660(5) N1 0.0608(10) 0.0386(9) 0.0444(8) 0.0036(6) 0.0302(7) 0.0048(7) C1 0.0507(10) 0.0365(11) 0.0504(9) -0.0037(8) 0.0266(8) 0.0003(8) C7 0.0573(11) 0.0409(11) 0.0391(9) 0.0000(7) 0.0253(7) 0.0067(8) N2 0.0915(14) 0.0561(12) 0.0520(9) 0.0165(8) 0.0415(9) 0.0150(10) N4 0.0742(13) 0.0579(12) 0.0415(8) 0.0051(7) 0.0344(8) 0.0115(9) N3 0.0930(15) 0.0636(13) 0.0496(9) 0.0150(8) 0.0425(10) 0.0157(10) C2 0.0617(13) 0.0575(14) 0.0825(15) -0.0157(11) 0.0444(12) -0.0139(11) C6 0.0728(15) 0.0458(14) 0.0828(15) -0.0147(11) 0.0410(12) -0.0099(11) C3 0.0823(18) 0.091(2) 0.114(2) -0.0223(16) 0.0725(17) -0.0083(15) C4 0.099(2) 0.081(2) 0.103(2) -0.0317(15) 0.0613(18) 0.0067(17) C5 0.100(2) 0.0568(17) 0.103(2) -0.0345(14) 0.0505(17) -0.0072(14) N5 0.1042(16) 0.0651(13) 0.0480(9) 0.0161(8) 0.0471(10) 0.0368(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 Cl1 C2 1.709(2) . ? N1 C7 1.346(2) . ? N1 N2 1.3714(19) . ? N1 C1 1.425(2) . ? C1 C6 1.371(3) . ? C1 C2 1.384(3) . ? C7 N5 1.323(2) . ? C7 N4 1.3322(19) . ? N2 N3 1.280(2) . ? N4 N3 1.356(2) . ? C2 C3 1.384(3) . ? C6 C5 1.373(3) . ? C3 C4 1.370(4) . ? C4 C5 1.361(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 N1 N2 108.07(14) . . ? C7 N1 C1 130.54(15) . . ? N2 N1 C1 120.74(16) . . ? C6 C1 C2 119.57(18) . . ? C6 C1 N1 119.15(17) . . ? C2 C1 N1 121.27(18) . . ? N5 C7 N4 125.71(17) . . ? N5 C7 N1 125.82(15) . . ? N4 C7 N1 108.47(15) . . ? N3 N2 N1 105.67(16) . . ? C7 N4 N3 105.18(15) . . ? N2 N3 N4 112.60(15) . . ? C1 C2 C3 119.2(2) . . ? C1 C2 Cl1 120.27(16) . . ? C3 C2 Cl1 120.51(18) . . ? C1 C6 C5 120.6(2) . . ? C4 C3 C2 120.4(2) . . ? C5 C4 C3 120.0(2) . . ? C4 C5 C6 120.1(2) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 28.35 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.419 _refine_diff_density_min -0.490 _refine_diff_density_rms 0.051 data_7b _database_code_depnum_ccdc_archive 'CCDC 787037' #TrackingRef '3b-7b-9b-17b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H9 Cl2 N5' _chemical_formula_sum 'C13 H9 Cl2 N5' _chemical_formula_weight 306.15 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' Cl Cl 0.1484 0.1585 '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 7.3229(2) _cell_length_b 9.8303(3) _cell_length_c 10.1610(3) _cell_angle_alpha 81.772(2) _cell_angle_beta 70.996(2) _cell_angle_gamma 76.860(2) _cell_volume 671.58(4) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5469 _cell_measurement_theta_min 2.90 _cell_measurement_theta_max 28.26 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 1.514 _exptl_crystal_density_diffrn 1.514 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.479 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9197 _diffrn_reflns_av_R_equivalents 0.0704 _diffrn_reflns_av_sigmaI/netI 0.0474 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 28.31 _reflns_number_total 3341 _reflns_number_gt 2756 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0573P)^2^+0.1167P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.050(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3280 _refine_ls_number_parameters 186 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0472 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.1242 _refine_ls_wR_factor_gt 0.1172 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _refine_ls_shift/su_max 0.004 _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 1.12069(8) 0.54198(5) 0.27397(6) 0.06821(19) Uani 1 1 d . . . Cl2 Cl 0.33696(7) 1.13966(6) 0.29135(6) 0.06812(19) Uani 1 1 d . . . N1 N 0.98776(17) 0.81415(12) 0.12742(14) 0.0417(3) Uani 1 1 d . . . N5 N 0.7384(2) 0.97929(14) 0.26915(15) 0.0470(3) Uani 1 1 d . . . N2 N 1.18322(19) 0.80500(15) 0.05335(16) 0.0534(4) Uani 1 1 d . . . N4 N 1.0765(2) 0.99979(14) 0.16024(16) 0.0511(3) Uani 1 1 d . . . N3 N 1.2319(2) 0.91522(16) 0.07557(18) 0.0570(4) Uani 1 1 d . . . C6 C 0.8853(2) 0.70545(14) 0.13092(15) 0.0382(3) Uani 1 1 d . . . C1 C 0.9393(2) 0.57330(15) 0.19316(16) 0.0425(3) Uani 1 1 d . . . C8 C 0.6782(2) 1.09175(14) 0.35509(15) 0.0415(3) Uani 1 1 d . . . C5 C 0.7340(2) 0.73168(16) 0.07234(17) 0.0466(4) Uani 1 1 d . . . H5 H 0.6975 0.8202 0.0314 0.056 Uiso 1 1 calc R . . C7 C 0.9269(2) 0.93532(14) 0.19026(16) 0.0401(3) Uani 1 1 d . . . C9 C 0.4901(2) 1.17284(16) 0.37719(16) 0.0462(4) Uani 1 1 d . . . C3 C 0.6948(3) 0.49314(18) 0.13297(19) 0.0546(4) Uani 1 1 d . . . H3 H 0.6311 0.4215 0.1324 0.066 Uiso 1 1 calc R . . C4 C 0.6368(2) 0.62500(19) 0.07503(19) 0.0533(4) Uani 1 1 d . . . H4 H 0.5327 0.6424 0.0378 0.064 Uiso 1 1 calc R . . C2 C 0.8456(3) 0.46602(16) 0.19157(18) 0.0514(4) Uani 1 1 d . . . H2 H 0.8843 0.3766 0.2298 0.062 Uiso 1 1 calc R . . C10 C 0.4225(3) 1.27904(19) 0.4678(2) 0.0619(5) Uani 1 1 d . . . H10 H 0.2961 1.3322 0.4822 0.074 Uiso 1 1 calc R . . C13 C 0.7987(3) 1.11988(19) 0.4244(2) 0.0570(4) Uani 1 1 d . . . H13 H 0.9252 1.0670 0.4106 0.068 Uiso 1 1 calc R . . C12 C 0.7313(4) 1.2264(2) 0.5142(2) 0.0688(5) Uani 1 1 d . . . H12 H 0.8130 1.2449 0.5601 0.083 Uiso 1 1 calc R . . C11 C 0.5437(4) 1.3052(2) 0.5360(2) 0.0710(6) Uani 1 1 d . . . H11 H 0.4991 1.3761 0.5969 0.085 Uiso 1 1 calc R . . H1N H 0.651(3) 0.946(2) 0.263(2) 0.058(6) 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 Cl1 0.0776(3) 0.0592(3) 0.0784(4) -0.0017(2) -0.0468(3) -0.0021(2) Cl2 0.0509(3) 0.0774(3) 0.0768(3) -0.0163(3) -0.0231(2) -0.0019(2) N1 0.0382(6) 0.0349(6) 0.0521(7) -0.0109(5) -0.0124(5) -0.0046(5) N5 0.0439(7) 0.0389(6) 0.0602(8) -0.0188(6) -0.0126(6) -0.0075(5) N2 0.0398(7) 0.0504(7) 0.0683(9) -0.0147(7) -0.0113(6) -0.0065(5) N4 0.0497(7) 0.0439(7) 0.0633(9) -0.0097(6) -0.0166(6) -0.0133(6) N3 0.0459(7) 0.0539(8) 0.0717(10) -0.0132(7) -0.0122(7) -0.0140(6) C6 0.0391(7) 0.0326(6) 0.0422(7) -0.0120(5) -0.0093(5) -0.0042(5) C1 0.0454(8) 0.0366(7) 0.0436(8) -0.0105(6) -0.0121(6) -0.0017(6) C8 0.0505(8) 0.0313(6) 0.0415(7) -0.0055(5) -0.0115(6) -0.0078(6) C5 0.0461(8) 0.0396(7) 0.0551(9) -0.0103(6) -0.0178(7) -0.0027(6) C7 0.0446(7) 0.0314(6) 0.0473(8) -0.0058(6) -0.0183(6) -0.0052(5) C9 0.0510(8) 0.0398(7) 0.0432(8) -0.0040(6) -0.0089(6) -0.0069(6) C3 0.0573(9) 0.0493(9) 0.0589(10) -0.0219(8) -0.0061(8) -0.0195(7) C4 0.0471(9) 0.0581(10) 0.0611(10) -0.0208(8) -0.0188(7) -0.0095(7) C2 0.0641(10) 0.0337(7) 0.0512(9) -0.0104(6) -0.0084(7) -0.0078(6) C10 0.0700(11) 0.0454(9) 0.0536(10) -0.0115(8) -0.0022(8) 0.0023(8) C13 0.0680(11) 0.0514(9) 0.0578(10) -0.0132(8) -0.0259(8) -0.0080(8) C12 0.0951(15) 0.0660(12) 0.0552(10) -0.0186(9) -0.0259(10) -0.0221(11) C11 0.1049(16) 0.0512(10) 0.0493(10) -0.0211(8) -0.0052(10) -0.0160(10) _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 1.7281(16) . ? Cl2 C9 1.7347(18) . ? N1 C7 1.3476(17) . ? N1 N2 1.3720(17) . ? N1 C6 1.4290(17) . ? N5 C7 1.357(2) . ? N5 C8 1.4082(18) . ? N2 N3 1.2846(19) . ? N4 C7 1.3183(19) . ? N4 N3 1.365(2) . ? C6 C5 1.380(2) . ? C6 C1 1.392(2) . ? C1 C2 1.387(2) . ? C8 C13 1.387(2) . ? C8 C9 1.391(2) . ? C5 C4 1.388(2) . ? C9 C10 1.388(2) . ? C3 C2 1.376(3) . ? C3 C4 1.379(3) . ? C10 C11 1.374(3) . ? C13 C12 1.384(2) . ? C12 C11 1.380(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 C7 N1 N2 107.59(12) . . ? C7 N1 C6 130.99(12) . . ? N2 N1 C6 121.40(11) . . ? C7 N5 C8 124.01(13) . . ? N3 N2 N1 106.02(12) . . ? C7 N4 N3 105.39(12) . . ? N2 N3 N4 111.86(13) . . ? C5 C6 C1 120.31(13) . . ? C5 C6 N1 119.95(13) . . ? C1 C6 N1 119.74(13) . . ? C2 C1 C6 119.85(15) . . ? C2 C1 Cl1 119.61(12) . . ? C6 C1 Cl1 120.55(11) . . ? C13 C8 C9 118.69(14) . . ? C13 C8 N5 121.55(15) . . ? C9 C8 N5 119.68(14) . . ? C6 C5 C4 119.50(15) . . ? N4 C7 N1 109.12(13) . . ? N4 C7 N5 127.83(13) . . ? N1 C7 N5 123.04(13) . . ? C10 C9 C8 120.98(16) . . ? C10 C9 Cl2 119.55(14) . . ? C8 C9 Cl2 119.47(11) . . ? C2 C3 C4 120.91(14) . . ? C3 C4 C5 119.97(16) . . ? C3 C2 C1 119.41(15) . . ? C11 C10 C9 119.55(18) . . ? C12 C13 C8 120.20(18) . . ? C11 C12 C13 120.47(19) . . ? C10 C11 C12 120.11(16) . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.387 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.045 data_9b _database_code_depnum_ccdc_archive 'CCDC 787038' #TrackingRef '3b-7b-9b-17b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H13 N5 O' _chemical_formula_sum 'C14 H13 N5 O' _chemical_formula_weight 267.29 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 10.8360(4) _cell_length_b 16.3772(6) _cell_length_c 7.6105(3) _cell_angle_alpha 90.00 _cell_angle_beta 107.280(2) _cell_angle_gamma 90.00 _cell_volume 1289.63(9) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5051 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas 1.377 _exptl_crystal_density_diffrn 1.377 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15943 _diffrn_reflns_av_R_equivalents 0.0633 _diffrn_reflns_av_sigmaI/netI 0.0359 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 28.38 _reflns_number_total 3221 _reflns_number_gt 1965 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0828P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.021(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3113 _refine_ls_number_parameters 187 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0672 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.1327 _refine_ls_wR_factor_gt 0.1203 _refine_ls_goodness_of_fit_ref 0.953 _refine_ls_restrained_S_all 0.953 _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 N1 N 0.14403(10) 0.21400(6) 0.41774(16) 0.0509(3) Uani 1 1 d . . . N5 N 0.34812(10) 0.14928(7) 0.54249(16) 0.0540(3) Uani 1 1 d . . . N2 N 0.10122(13) 0.29273(7) 0.38491(19) 0.0695(4) Uani 1 1 d . . . N4 N 0.31189(12) 0.29338(7) 0.50218(18) 0.0655(4) Uani 1 1 d . . . N3 N 0.20196(13) 0.33790(7) 0.4351(2) 0.0778(4) Uani 1 1 d . . . O1 O 0.44775(8) 0.01767(5) 0.72129(13) 0.0605(3) Uani 1 1 d . . . C1 C 0.05379(12) 0.14774(7) 0.37641(17) 0.0472(3) Uani 1 1 d . . . C8 C 0.48251(12) 0.14871(7) 0.62733(17) 0.0474(3) Uani 1 1 d . . . C7 C 0.27330(12) 0.21652(7) 0.49040(17) 0.0480(3) Uani 1 1 d . . . C13 C 0.53501(11) 0.07797(8) 0.72312(17) 0.0493(3) Uani 1 1 d . . . C6 C 0.07191(13) 0.08333(8) 0.27057(18) 0.0557(3) Uani 1 1 d . . . H6 H 0.1438 0.0815 0.2277 0.067 Uiso 1 1 calc R . . C9 C 0.56437(14) 0.21213(8) 0.6142(2) 0.0601(4) Uani 1 1 d . . . H9 H 0.5308 0.2585 0.5464 0.072 Uiso 1 1 calc R . . C4 C -0.12580(14) 0.02448(9) 0.28959(19) 0.0619(4) Uani 1 1 d . . . H4 H -0.1874 -0.0168 0.2587 0.074 Uiso 1 1 calc R . . C12 C 0.66627(13) 0.07381(10) 0.8109(2) 0.0650(4) Uani 1 1 d . . . H12 H 0.7014 0.0272 0.8766 0.078 Uiso 1 1 calc R . . C5 C -0.01893(15) 0.02120(8) 0.22902(19) 0.0619(4) Uani 1 1 d . . . H5 H -0.0072 -0.0231 0.1593 0.074 Uiso 1 1 calc R . . C14 C 0.49804(15) -0.06004(8) 0.7972(2) 0.0668(4) Uani 1 1 d . . . H14A H 0.5543 -0.0811 0.7316 0.100 Uiso 1 1 calc R . . H14B H 0.4279 -0.0974 0.7861 0.100 Uiso 1 1 calc R . . H14C H 0.5455 -0.0535 0.9248 0.100 Uiso 1 1 calc R . . C2 C -0.05197(12) 0.15046(8) 0.44172(19) 0.0580(4) Uani 1 1 d . . . H2 H -0.0624 0.1935 0.5158 0.070 Uiso 1 1 calc R . . C3 C -0.14175(13) 0.08883(9) 0.3960(2) 0.0648(4) Uani 1 1 d . . . H3 H -0.2142 0.0908 0.4377 0.078 Uiso 1 1 calc R . . C10 C 0.69493(15) 0.20648(10) 0.7013(3) 0.0716(4) Uani 1 1 d . . . H10 H 0.7493 0.2492 0.6920 0.086 Uiso 1 1 calc R . . C11 C 0.74542(14) 0.13849(11) 0.8013(2) 0.0748(5) Uani 1 1 d . . . H11 H 0.8334 0.1359 0.8631 0.090 Uiso 1 1 calc R . . H5N H 0.3073(14) 0.1060(10) 0.549(2) 0.072(5) 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 N1 0.0476(6) 0.0346(6) 0.0605(7) 0.0041(4) 0.0009(5) 0.0081(4) N5 0.0420(6) 0.0358(6) 0.0736(8) 0.0070(5) 0.0011(5) 0.0002(5) N2 0.0661(8) 0.0390(6) 0.0915(10) 0.0075(6) 0.0051(7) 0.0137(6) N4 0.0628(8) 0.0358(6) 0.0881(9) 0.0006(5) 0.0076(7) -0.0001(5) N3 0.0724(9) 0.0384(7) 0.1107(11) 0.0057(6) 0.0091(8) 0.0057(6) O1 0.0493(5) 0.0471(5) 0.0771(7) 0.0153(4) 0.0064(5) 0.0087(4) C1 0.0421(7) 0.0395(6) 0.0494(7) 0.0039(5) -0.0025(5) 0.0055(5) C8 0.0409(7) 0.0465(7) 0.0499(7) -0.0046(5) 0.0059(5) 0.0009(5) C7 0.0490(7) 0.0359(7) 0.0527(8) 0.0014(5) 0.0055(6) 0.0005(5) C13 0.0437(7) 0.0503(7) 0.0501(7) -0.0018(5) 0.0081(5) 0.0040(6) C6 0.0558(8) 0.0497(8) 0.0592(8) -0.0002(6) 0.0137(6) 0.0040(6) C9 0.0533(8) 0.0516(8) 0.0727(10) -0.0044(6) 0.0145(7) -0.0036(6) C4 0.0551(9) 0.0593(8) 0.0582(8) 0.0042(6) -0.0034(7) -0.0090(6) C12 0.0481(8) 0.0733(9) 0.0649(9) -0.0001(7) 0.0037(7) 0.0133(7) C5 0.0696(10) 0.0471(8) 0.0601(9) -0.0074(6) 0.0056(7) 0.0002(7) C14 0.0700(9) 0.0468(8) 0.0763(10) 0.0095(7) 0.0107(8) 0.0176(7) C2 0.0475(8) 0.0590(8) 0.0590(8) -0.0067(6) 0.0027(6) 0.0089(6) C3 0.0482(8) 0.0756(10) 0.0638(9) 0.0004(7) 0.0064(7) -0.0022(7) C10 0.0513(9) 0.0711(10) 0.0916(12) -0.0179(8) 0.0200(8) -0.0139(7) C11 0.0428(8) 0.0885(12) 0.0853(11) -0.0154(9) 0.0071(7) 0.0002(8) _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 N1 C7 1.3451(17) . ? N1 N2 1.3680(14) . ? N1 C1 1.4318(15) . ? N5 C7 1.3551(15) . ? N5 C8 1.4068(17) . ? N2 N3 1.2794(17) . ? N4 C7 1.3210(15) . ? N4 N3 1.3603(17) . ? O1 C13 1.3645(15) . ? O1 C14 1.4365(15) . ? C1 C6 1.3763(17) . ? C1 C2 1.3787(18) . ? C8 C9 1.3886(18) . ? C8 C13 1.3969(17) . ? C13 C12 1.3819(18) . ? C6 C5 1.3853(18) . ? C9 C10 1.376(2) . ? C4 C5 1.369(2) . ? C4 C3 1.371(2) . ? C12 C11 1.378(2) . ? C2 C3 1.3730(18) . ? C10 C11 1.368(2) . ? 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 N1 N2 107.54(10) . . ? C7 N1 C1 132.33(9) . . ? N2 N1 C1 120.12(10) . . ? C7 N5 C8 125.98(11) . . ? N3 N2 N1 106.11(11) . . ? C7 N4 N3 105.13(11) . . ? N2 N3 N4 112.12(11) . . ? C13 O1 C14 117.27(10) . . ? C6 C1 C2 120.95(12) . . ? C6 C1 N1 120.17(12) . . ? C2 C1 N1 118.87(11) . . ? C9 C8 C13 119.21(12) . . ? C9 C8 N5 123.94(12) . . ? C13 C8 N5 116.78(11) . . ? N4 C7 N1 109.10(10) . . ? N4 C7 N5 127.20(12) . . ? N1 C7 N5 123.70(11) . . ? O1 C13 C12 125.45(12) . . ? O1 C13 C8 114.93(10) . . ? C12 C13 C8 119.62(12) . . ? C1 C6 C5 118.76(12) . . ? C10 C9 C8 120.17(14) . . ? C5 C4 C3 119.78(13) . . ? C11 C12 C13 120.26(14) . . ? C4 C5 C6 120.61(13) . . ? C3 C2 C1 119.15(12) . . ? C4 C3 C2 120.71(13) . . ? C11 C10 C9 120.46(14) . . ? C10 C11 C12 120.17(14) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.38 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.177 _refine_diff_density_min -0.179 _refine_diff_density_rms 0.038 data_17b _database_code_depnum_ccdc_archive 'CCDC 812122' #TrackingRef '3b-7b-9b-17b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl2 N4 S' _chemical_formula_sum 'C14 H10 Cl2 N4 S' _chemical_formula_weight 337.22 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' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' 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 29.6523(10) _cell_length_b 5.8630(3) _cell_length_c 17.3440(7) _cell_angle_alpha 90.00 _cell_angle_beta 108.649(3) _cell_angle_gamma 90.00 _cell_volume 2857.0(2) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.45 _cell_measurement_theta_max 27.530 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 1.568 _exptl_crystal_density_diffrn 1.568 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1376 _exptl_absorpt_coefficient_mu 0.597 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.836 _exptl_absorpt_correction_T_max 0.887 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10385 _diffrn_reflns_av_R_equivalents 0.0211 _diffrn_reflns_av_sigmaI/netI 0.0211 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 27.53 _reflns_number_total 3294 _reflns_number_gt 2380 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0297P)^2^+3.3294P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef ? _refine_ls_number_reflns 2820 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0400 _refine_ls_R_factor_gt 0.0319 _refine_ls_wR_factor_ref 0.0778 _refine_ls_wR_factor_gt 0.0735 _refine_ls_goodness_of_fit_ref 0.988 _refine_ls_restrained_S_all 0.988 _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 Cl2 Cl 0.22242(2) 1.09027(11) 0.60235(3) 0.0650(2) Uani 1 1 d . . . Cl1 Cl -0.191606(19) 0.91634(10) 0.12967(4) 0.05907(18) Uani 1 1 d . . . S3 S 0.043710(16) 1.04480(8) 0.43813(3) 0.03739(14) Uani 1 1 d . . . N1 N -0.03000(5) 1.2153(2) 0.31715(9) 0.0387(4) Uani 1 1 d . . . H1N H -0.0145 1.3397 0.3335 0.046 Uiso 1 1 d R . . N2 N -0.03172(5) 0.8269(2) 0.35515(9) 0.0390(4) Uani 1 1 d . . . N3 N -0.00321(6) 0.6698(2) 0.41004(9) 0.0400(4) Uani 1 1 d . . . N4 N 0.06528(5) 0.6343(3) 0.52009(9) 0.0400(4) Uani 1 1 d . . . H4N H 0.0533 0.5075 0.5290 0.048 Uiso 1 1 d R . . C4 C -0.14930(7) 1.3083(3) 0.11016(11) 0.0451(5) Uani 1 1 d . . . H4 H -0.1756 1.3318 0.0642 0.054 Uiso 1 1 calc R . . C5 C -0.11346(7) 1.4682(3) 0.13417(11) 0.0436(5) Uani 1 1 d . . . H5 H -0.1158 1.6017 0.1042 0.052 Uiso 1 1 calc R . . C6 C -0.07421(7) 1.4333(3) 0.20202(11) 0.0378(4) Uani 1 1 d . . . H6 H -0.0504 1.5431 0.2175 0.045 Uiso 1 1 calc R . . C1 C -0.07023(6) 1.2337(3) 0.24732(10) 0.0335(4) Uani 1 1 d . . . C2 C -0.10592(7) 1.0693(3) 0.22398(10) 0.0370(4) Uani 1 1 d . . . H2 H -0.1036 0.9342 0.2531 0.044 Uiso 1 1 calc R . . C3 C -0.14513(7) 1.1129(3) 0.15588(11) 0.0403(4) Uani 1 1 d . . . C9 C 0.11162(6) 0.6766(3) 0.57209(9) 0.0343(4) Uani 1 1 d . . . C10 C 0.14071(7) 0.8487(3) 0.56034(10) 0.0388(4) Uani 1 1 d . . . H10 H 0.1304 0.9450 0.5155 0.047 Uiso 1 1 calc R . . C11 C 0.18580(7) 0.8745(3) 0.61709(11) 0.0419(5) Uani 1 1 d . . . C12 C 0.20213(7) 0.7351(4) 0.68384(11) 0.0493(5) Uani 1 1 d . . . H12 H 0.2322 0.7570 0.7215 0.059 Uiso 1 1 calc R . . C13 C 0.17321(7) 0.5627(4) 0.69391(12) 0.0504(5) Uani 1 1 d . . . H13 H 0.1840 0.4662 0.7386 0.060 Uiso 1 1 calc R . . C14 C 0.12848(7) 0.5305(3) 0.63883(11) 0.0419(4) Uani 1 1 d . . . H14 H 0.1095 0.4115 0.6461 0.050 Uiso 1 1 calc R . . C7 C -0.01213(6) 1.0260(3) 0.36250(9) 0.0318(4) Uani 1 1 d . . . C8 C 0.03609(6) 0.7591(3) 0.45798(9) 0.0320(4) 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 Cl2 0.0423(4) 0.0778(4) 0.0632(3) 0.0052(3) 0.0005(2) -0.0251(3) Cl1 0.0381(3) 0.0542(3) 0.0712(3) 0.0010(2) -0.0018(2) -0.0065(2) S3 0.0325(3) 0.0323(2) 0.0408(2) 0.00173(17) 0.00250(17) -0.0098(2) N1 0.0382(10) 0.0281(7) 0.0428(8) 0.0019(6) 0.0030(6) -0.0075(7) N2 0.0364(9) 0.0307(7) 0.0403(8) 0.0022(6) -0.0015(6) -0.0066(7) N3 0.0371(9) 0.0313(7) 0.0411(8) 0.0029(6) -0.0023(6) -0.0065(7) N4 0.0350(9) 0.0358(8) 0.0411(8) 0.0070(6) 0.0009(6) -0.0100(7) C4 0.0405(12) 0.0486(11) 0.0410(9) 0.0046(8) 0.0055(8) 0.0107(10) C5 0.0470(13) 0.0396(10) 0.0457(10) 0.0095(8) 0.0169(8) 0.0099(9) C6 0.0386(12) 0.0319(9) 0.0449(9) 0.0015(7) 0.0163(8) 0.0004(8) C1 0.0326(11) 0.0317(8) 0.0360(8) -0.0015(7) 0.0107(7) 0.0030(8) C2 0.0358(11) 0.0325(9) 0.0402(9) 0.0009(7) 0.0084(7) 0.0011(8) C3 0.0326(11) 0.0400(10) 0.0452(10) -0.0036(8) 0.0081(8) 0.0023(8) C9 0.0291(10) 0.0384(9) 0.0327(8) -0.0030(7) 0.0059(6) -0.0003(8) C10 0.0334(11) 0.0442(10) 0.0347(8) 0.0029(7) 0.0049(7) -0.0042(9) C11 0.0297(11) 0.0500(11) 0.0425(9) -0.0040(8) 0.0067(7) -0.0056(9) C12 0.0301(11) 0.0699(14) 0.0407(10) 0.0025(9) 0.0012(8) 0.0012(11) C13 0.0371(12) 0.0652(14) 0.0439(10) 0.0144(9) 0.0062(8) 0.0097(11) C14 0.0357(11) 0.0433(10) 0.0453(10) 0.0080(8) 0.0113(8) 0.0019(9) C7 0.0300(10) 0.0321(8) 0.0318(8) -0.0017(6) 0.0076(6) -0.0055(8) C8 0.0309(10) 0.0313(8) 0.0324(8) -0.0014(6) 0.0082(6) -0.0061(8) _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 Cl2 C11 1.739(2) . ? Cl1 C3 1.742(2) . ? S3 C8 1.7393(17) . ? S3 C7 1.7565(17) . ? N1 C7 1.365(2) . ? N1 C1 1.406(2) . ? N1 H1N 0.8599 . ? N2 C7 1.292(2) . ? N2 N3 1.3981(19) . ? N3 C8 1.305(2) . ? N4 C8 1.359(2) . ? N4 C9 1.404(2) . ? N4 H4N 0.8599 . ? C4 C3 1.376(3) . ? C4 C5 1.378(3) . ? C4 H4 0.9300 . ? C5 C6 1.380(3) . ? C5 H5 0.9300 . ? C6 C1 1.393(2) . ? C6 H6 0.9300 . ? C1 C2 1.393(2) . ? C2 C3 1.391(2) . ? C2 H2 0.9300 . ? C9 C10 1.385(3) . ? C9 C14 1.397(2) . ? C10 C11 1.392(2) . ? C10 H10 0.9300 . ? C11 C12 1.373(3) . ? C12 C13 1.372(3) . ? C12 H12 0.9300 . ? C13 C14 1.377(3) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? 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 C8 S3 C7 86.35(8) . . ? C7 N1 C1 128.63(14) . . ? C7 N1 H1N 115.6 . . ? C1 N1 H1N 115.8 . . ? C7 N2 N3 111.91(13) . . ? C8 N3 N2 113.07(14) . . ? C8 N4 C9 131.20(15) . . ? C8 N4 H4N 114.3 . . ? C9 N4 H4N 114.5 . . ? C3 C4 C5 118.27(17) . . ? C3 C4 H4 120.9 . . ? C5 C4 H4 120.9 . . ? C6 C5 C4 121.03(17) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C1 120.10(18) . . ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 . . ? C6 C1 C2 119.86(16) . . ? C6 C1 N1 116.45(16) . . ? C2 C1 N1 123.65(15) . . ? C3 C2 C1 118.08(16) . . ? C3 C2 H2 121.0 . . ? C1 C2 H2 121.0 . . ? C4 C3 C2 122.64(18) . . ? C4 C3 Cl1 118.86(14) . . ? C2 C3 Cl1 118.46(15) . . ? C10 C9 C14 119.59(16) . . ? C10 C9 N4 124.19(15) . . ? C14 C9 N4 116.22(17) . . ? C9 C10 C11 118.54(16) . . ? C9 C10 H10 120.7 . . ? C11 C10 H10 120.7 . . ? C12 C11 C10 122.12(19) . . ? C12 C11 Cl2 119.27(15) . . ? C10 C11 Cl2 118.61(15) . . ? C11 C12 C13 118.66(18) . . ? C11 C12 H12 120.7 . . ? C13 C12 H12 120.7 . . ? C12 C13 C14 120.99(18) . . ? C12 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? C13 C14 C9 120.05(19) . . ? C13 C14 H14 120.0 . . ? C9 C14 H14 120.0 . . ? N2 C7 N1 126.73(15) . . ? N2 C7 S3 114.65(12) . . ? N1 C7 S3 118.61(12) . . ? N3 C8 N4 120.10(15) . . ? N3 C8 S3 113.96(13) . . ? N4 C8 S3 125.80(13) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.226 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.039