# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_compound_1a _database_code_depnum_ccdc_archive 'CCDC 913178' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H14 N2 O2 S' _chemical_formula_sum 'C19 H14 N2 O2 S' _chemical_formula_weight 334.38 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 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 12.2213(5) _cell_length_b 12.5273(5) _cell_length_c 11.9600(4) _cell_angle_alpha 90.00 _cell_angle_beta 119.087(1) _cell_angle_gamma 90.00 _cell_volume 1600.1(1) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 4419 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description 'rectangular prism' _exptl_crystal_colour 'light orange' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.388 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.216 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.9083 _exptl_absorpt_correction_T_max 0.9887 _exptl_absorpt_process_details 'HKL Scalepack (Otwinowski & Minor 1997)' _exptl_special_details ; There was disorder of the complete structure which was modeled as a 92:8 mixture. The main component was refined with anisotropic thermal displacement parameters while the minor component was refined with isotropic parameters and mild geometric restraints. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 15888 _diffrn_reflns_av_R_equivalents 0.0395 _diffrn_reflns_av_sigmaI/netI 0.0399 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.70 _diffrn_reflns_theta_max 27.51 _reflns_number_total 3661 _reflns_number_gt 2769 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0514P)^2^+0.5589P] 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 3661 _refine_ls_number_parameters 308 _refine_ls_number_restraints 44 _refine_ls_R_factor_all 0.0688 _refine_ls_R_factor_gt 0.0465 _refine_ls_wR_factor_ref 0.1201 _refine_ls_wR_factor_gt 0.1085 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.020 _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 S1 S 0.74599(5) 0.10586(4) 0.87274(5) 0.04339(16) Uani 0.92 1 d P A 1 N1 N 0.77487(15) 0.23770(13) 0.90462(15) 0.0418(4) Uani 0.92 1 d P A 1 C1 C 0.70706(17) 0.28806(16) 0.94332(18) 0.0389(4) Uani 0.92 1 d P A 1 C2 C 0.7259(2) 0.4048(2) 0.9632(3) 0.0408(5) Uani 0.92 1 d P A 1 C3 C 0.6515(3) 0.4660(2) 0.9954(3) 0.0645(7) Uani 0.92 1 d P A 1 H3A H 0.5916 0.4321 1.0124 0.077 Uiso 0.92 1 calc PR A 1 C4 C 0.6627(3) 0.5758(2) 1.0033(3) 0.0625(7) Uani 0.92 1 d P A 1 H4A H 0.6093 0.6167 1.0237 0.075 Uiso 0.92 1 calc PR A 1 C5 C 0.7497(3) 0.6261(2) 0.9819(4) 0.0540(7) Uani 0.92 1 d P A 1 H5A H 0.7558 0.7017 0.9856 0.065 Uiso 0.92 1 calc PR A 1 C6 C 0.8286(3) 0.5664(2) 0.9550(3) 0.0623(7) Uani 0.92 1 d P A 1 H6A H 0.8909 0.6008 0.9422 0.075 Uiso 0.92 1 calc PR A 1 C7 C 0.8174(2) 0.4564(2) 0.9466(3) 0.0512(6) Uani 0.92 1 d P A 1 H7A H 0.8730 0.4158 0.9293 0.061 Uiso 0.92 1 calc PR A 1 C8 C 0.6093(2) 0.23308(17) 0.9642(3) 0.0386(5) Uani 0.92 1 d P A 1 C9 C 0.4913(3) 0.2122(2) 0.8619(3) 0.0480(7) Uani 0.92 1 d P A 1 H9A H 0.4705 0.2354 0.7783 0.058 Uiso 0.92 1 calc PR A 1 C10 C 0.4038(3) 0.1573(3) 0.8821(3) 0.0523(6) Uani 0.92 1 d P A 1 H10A H 0.3230 0.1438 0.8119 0.063 Uiso 0.92 1 calc PR A 1 C11 C 0.4324(2) 0.1223(3) 1.0017(3) 0.0494(6) Uani 0.92 1 d P A 1 H11A H 0.3722 0.0840 1.0143 0.059 Uiso 0.92 1 calc PR A 1 C12 C 0.5491(3) 0.1429(2) 1.1037(2) 0.0515(7) Uani 0.92 1 d P A 1 H12A H 0.5692 0.1191 1.1870 0.062 Uiso 0.92 1 calc PR A 1 C13 C 0.6373(2) 0.1983(2) 1.0852(3) 0.0465(5) Uani 0.92 1 d P A 1 H13A H 0.7175 0.2124 1.1560 0.056 Uiso 0.92 1 calc PR A 1 C14 C 0.87329(18) 0.07604(16) 0.84730(17) 0.0379(4) Uani 0.92 1 d P A 1 C15 C 0.90096(18) -0.02850(16) 0.82842(18) 0.0402(4) Uani 0.92 1 d P A 1 C16 C 1.0019(2) -0.05413(18) 0.8103(2) 0.0470(5) Uani 0.92 1 d P A 1 H16A H 1.0179 -0.1264 0.7987 0.056 Uiso 0.92 1 calc PR A 1 C17 C 1.0782(2) 0.0253(2) 0.8091(2) 0.0515(5) Uani 0.92 1 d P A 1 H17A H 1.1467 0.0091 0.7956 0.062 Uiso 0.92 1 calc PR A 1 C18 C 1.0540(3) 0.1301(2) 0.8281(2) 0.0488(6) Uani 0.92 1 d P A 1 H18A H 1.1068 0.1855 0.8277 0.059 Uiso 0.92 1 calc PR A 1 C19 C 0.95401(19) 0.15531(19) 0.8476(2) 0.0429(5) Uani 0.92 1 d P A 1 H19A H 0.9401 0.2276 0.8613 0.051 Uiso 0.92 1 calc PR A 1 N2 N 0.8249(2) -0.11714(15) 0.82999(18) 0.0481(4) Uani 0.92 1 d P A 1 O1 O 0.72704(16) -0.09575(14) 0.83075(18) 0.0608(4) Uani 0.92 1 d P A 1 O2 O 0.86182(18) -0.20853(13) 0.83281(18) 0.0670(5) Uani 0.92 1 d P A 1 S1A S 0.8657(6) 0.0872(5) 1.1201(6) 0.0478(13) Uiso 0.08 1 d P B 2 N1A N 0.8495(14) 0.2172(14) 1.0728(16) 0.040(4) Uiso 0.08 1 d PD B 2 C1A C 0.7425(15) 0.2679(13) 1.020(2) 0.051(6) Uiso 0.08 1 d PD B 2 C2A C 0.731(2) 0.3857(13) 0.9934(14) 0.031(9) Uiso 0.08 1 d PD B 2 C3A C 0.8321(19) 0.4392(18) 0.995(2) 0.037(7) Uiso 0.08 1 d PD B 2 H3B H 0.9046 0.3988 1.0124 0.044 Uiso 0.08 1 calc PR B 2 C4A C 0.833(2) 0.5478(19) 0.972(3) 0.0623(7) Uani 0.08 1 d PD B 2 H4B H 0.9043 0.5802 0.9740 0.075 Uiso 0.08 1 calc PR B 2 C5A C 0.728(2) 0.6085(19) 0.946(2) 0.072(18) Uiso 0.08 1 d PD B 2 H5B H 0.7276 0.6828 0.9298 0.086 Uiso 0.08 1 calc PR B 2 C6A C 0.6240(18) 0.5611(15) 0.943(2) 0.032(5) Uiso 0.08 1 d PD B 2 H6B H 0.5518 0.6019 0.9250 0.039 Uiso 0.08 1 calc PR B 2 C7A C 0.629(2) 0.4517(16) 0.966(2) 0.0645(7) Uani 0.08 1 d PD B 2 H7B H 0.5570 0.4196 0.9636 0.077 Uiso 0.08 1 calc PR B 2 C8A C 0.6328(17) 0.2132(15) 1.017(3) 0.024(5) Uiso 0.08 1 d PD B 2 C9A C 0.525(3) 0.215(3) 0.899(2) 0.040(10) Uiso 0.08 1 d PD B 2 H9B H 0.5269 0.2463 0.8275 0.048 Uiso 0.08 1 calc PR B 2 C10A C 0.414(3) 0.172(4) 0.884(3) 0.0523(6) Uani 0.08 1 d PD B 2 H10B H 0.3408 0.1735 0.8024 0.063 Uiso 0.08 1 calc PR B 2 C11A C 0.409(3) 0.125(4) 0.987(4) 0.0494(6) Uani 0.08 1 d PD B 2 H11B H 0.3331 0.0956 0.9768 0.059 Uiso 0.08 1 calc PR B 2 C12A C 0.517(3) 0.124(3) 1.105(3) 0.059(14) Uiso 0.08 1 d PD B 2 H12B H 0.5154 0.0924 1.1764 0.071 Uiso 0.08 1 calc PR B 2 C13A C 0.627(2) 0.1670(18) 1.119(2) 0.034(6) Uiso 0.08 1 d PD B 2 H13B H 0.7006 0.1651 1.2006 0.041 Uiso 0.08 1 calc PR B 2 C14A C 1.0262(17) 0.0620(15) 1.1472(17) 0.036(5) Uiso 0.08 1 d PD B 2 C15A C 1.0822(17) -0.0376(14) 1.1805(17) 0.048(6) Uiso 0.08 1 d PD B 2 C16A C 1.2030(18) -0.0562(15) 1.2034(18) 0.058(7) Uiso 0.08 1 d PD B 2 H16B H 1.2384 -0.1256 1.2259 0.070 Uiso 0.08 1 calc PR B 2 C17A C 1.2721(17) 0.0275(18) 1.1931(19) 0.048(6) Uiso 0.08 1 d PD B 2 H17B H 1.3553 0.0161 1.2088 0.058 Uiso 0.08 1 calc PR B 2 C18A C 1.218(2) 0.1280(16) 1.160(2) 0.0481(4) Uani 0.08 1 d PD B 2 H18B H 1.2645 0.1856 1.1521 0.058 Uiso 0.08 1 calc PR B 2 C19A C 1.096(2) 0.1457(14) 1.1369(19) 0.056(7) Uiso 0.08 1 d PD B 2 H19B H 1.0604 0.2151 1.1142 0.067 Uiso 0.08 1 calc PR B 2 N2A N 1.014(3) -0.1296(18) 1.189(2) 0.046(6) Uiso 0.08 1 d PD B 2 O1A O 1.062(2) -0.217(2) 1.202(2) 0.082(6) Uiso 0.08 1 d PD B 2 O2A O 0.917(3) -0.102(3) 1.185(3) 0.067(9) Uiso 0.08 1 d PD B 2 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 0.0473(3) 0.0348(3) 0.0593(3) -0.0009(2) 0.0348(2) -0.0020(2) N1 0.0453(9) 0.0350(9) 0.0519(10) 0.0006(7) 0.0289(8) 0.0016(7) C1 0.0399(10) 0.0377(11) 0.0390(10) 0.0028(8) 0.0189(8) 0.0018(8) C2 0.0441(13) 0.0392(12) 0.0418(11) -0.0010(11) 0.0229(10) -0.0004(9) C3 0.0640(15) 0.0446(14) 0.107(2) -0.0162(13) 0.0592(16) -0.0101(11) C4 0.0631(15) 0.0455(14) 0.090(2) -0.0130(14) 0.0462(16) -0.0028(12) C5 0.0531(14) 0.0404(13) 0.0654(16) -0.0038(14) 0.0263(13) -0.0039(11) C6 0.0567(13) 0.0518(15) 0.0832(18) 0.0015(13) 0.0378(12) -0.0093(12) C7 0.0451(12) 0.0543(15) 0.0588(17) -0.0030(12) 0.0288(11) -0.0006(10) C8 0.0419(12) 0.0343(11) 0.0429(13) -0.0010(10) 0.0232(11) 0.0029(9) C9 0.0441(15) 0.0530(16) 0.0473(14) 0.0049(12) 0.0225(14) -0.0009(12) C10 0.0428(11) 0.0525(18) 0.0616(12) -0.0012(11) 0.0254(10) -0.0067(10) C11 0.0545(15) 0.0417(12) 0.0661(18) -0.0044(11) 0.0404(15) -0.0037(13) C12 0.069(2) 0.0462(14) 0.0511(14) -0.0025(10) 0.0386(14) -0.0018(14) C13 0.0526(12) 0.0454(13) 0.0432(13) -0.0051(10) 0.0246(10) -0.0067(10) C14 0.0408(10) 0.0354(10) 0.0404(10) -0.0004(8) 0.0220(9) -0.0005(8) C15 0.0449(11) 0.0350(11) 0.0434(10) -0.0021(8) 0.0236(9) -0.0030(9) C16 0.0486(12) 0.0424(12) 0.0545(12) -0.0085(9) 0.0286(10) -0.0003(9) C17 0.0467(12) 0.0521(15) 0.0646(14) -0.0060(11) 0.0340(10) -0.0006(10) C18 0.0487(17) 0.0434(15) 0.0594(15) -0.0014(11) 0.0304(13) -0.0064(12) C19 0.0449(11) 0.0369(11) 0.0507(12) 0.0024(10) 0.0262(10) -0.0004(9) N2 0.0615(13) 0.0382(10) 0.0568(10) -0.0055(8) 0.0383(9) -0.0053(9) O1 0.0682(11) 0.0444(10) 0.0942(12) -0.0095(8) 0.0586(10) -0.0113(8) O2 0.0903(12) 0.0333(9) 0.0985(13) -0.0077(8) 0.0624(11) -0.0042(8) C4A 0.0567(13) 0.0518(15) 0.0832(18) 0.0015(13) 0.0378(12) -0.0093(12) C7A 0.0640(15) 0.0446(14) 0.107(2) -0.0162(13) 0.0592(16) -0.0101(11) C10A 0.0428(11) 0.0525(18) 0.0616(12) -0.0012(11) 0.0254(10) -0.0067(10) C11A 0.0545(15) 0.0417(12) 0.0661(18) -0.0044(11) 0.0404(15) -0.0037(13) C18A 0.0615(13) 0.0382(10) 0.0568(10) -0.0055(8) 0.0383(9) -0.0053(9) _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 S1 N1 1.6932(18) . ? S1 C14 1.764(2) . ? N1 C1 1.293(2) . ? C1 C2 1.482(3) . ? C1 C8 1.501(3) . ? C2 C3 1.380(3) . ? C2 C7 1.387(3) . ? C3 C4 1.381(4) . ? C4 C5 1.362(3) . ? C5 C6 1.376(4) . ? C6 C7 1.383(4) . ? C8 C13 1.385(3) . ? C8 C9 1.390(4) . ? C9 C10 1.386(3) . ? C10 C11 1.370(3) . ? C11 C12 1.377(4) . ? C12 C13 1.387(4) . ? C14 C15 1.398(3) . ? C14 C19 1.399(3) . ? C15 C16 1.390(3) . ? C15 N2 1.454(3) . ? C16 C17 1.368(3) . ? C17 C18 1.388(4) . ? C18 C19 1.387(4) . ? N2 O2 1.225(2) . ? N2 O1 1.230(2) . ? S1A N1A 1.704(19) . ? S1A C14A 1.85(2) . ? N1A C1A 1.308(10) . ? C1A C8A 1.489(10) . ? C1A C2A 1.502(10) . ? C2A C3A 1.396(8) . ? C2A C7A 1.402(8) . ? C3A C4A 1.390(8) . ? C4A C5A 1.388(8) . ? C5A C6A 1.388(8) . ? C6A C7A 1.395(8) . ? C8A C9A 1.384(8) . ? C8A C13A 1.385(8) . ? C9A C10A 1.391(8) . ? C10A C11A 1.389(8) . ? C11A C12A 1.387(8) . ? C12A C13A 1.386(8) . ? C14A C15A 1.385(8) . ? C14A C19A 1.395(8) . ? C15A C16A 1.385(8) . ? C15A N2A 1.46(3) . ? C16A C17A 1.388(8) . ? C17A C18A 1.388(8) . ? C18A C19A 1.396(8) . ? N2A O2A 1.22(2) . ? N2A O1A 1.22(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 N1 S1 C14 98.08(9) . . ? C1 N1 S1 117.19(14) . . ? N1 C1 C2 117.56(18) . . ? N1 C1 C8 122.41(18) . . ? C2 C1 C8 120.00(18) . . ? C3 C2 C7 117.9(2) . . ? C3 C2 C1 121.4(2) . . ? C7 C2 C1 120.7(2) . . ? C2 C3 C4 121.0(2) . . ? C5 C4 C3 120.6(3) . . ? C4 C5 C6 119.5(3) . . ? C5 C6 C7 120.1(2) . . ? C6 C7 C2 120.8(2) . . ? C13 C8 C9 118.9(2) . . ? C13 C8 C1 120.4(2) . . ? C9 C8 C1 120.6(2) . . ? C10 C9 C8 119.9(3) . . ? C11 C10 C9 120.9(3) . . ? C10 C11 C12 119.6(3) . . ? C11 C12 C13 120.2(2) . . ? C8 C13 C12 120.5(2) . . ? C15 C14 C19 116.08(19) . . ? C15 C14 S1 121.94(15) . . ? C19 C14 S1 121.97(16) . . ? C16 C15 C14 122.97(19) . . ? C16 C15 N2 116.56(19) . . ? C14 C15 N2 120.46(18) . . ? C17 C16 C15 119.6(2) . . ? C16 C17 C18 119.1(2) . . ? C19 C18 C17 121.2(3) . . ? C18 C19 C14 121.1(2) . . ? O2 N2 O1 123.3(2) . . ? O2 N2 C15 119.01(19) . . ? O1 N2 C15 117.63(18) . . ? N1A S1A C14A 99.4(8) . . ? C1A N1A S1A 123.5(14) . . ? N1A C1A C8A 117.7(16) . . ? N1A C1A C2A 123.1(16) . . ? C8A C1A C2A 117.3(16) . . ? C3A C2A C7A 113.9(13) . . ? C3A C2A C1A 118.7(17) . . ? C7A C2A C1A 127.5(17) . . ? C4A C3A C2A 124.0(13) . . ? C5A C4A C3A 119.0(15) . . ? C4A C5A C6A 120.4(16) . . ? C5A C6A C7A 117.9(14) . . ? C6A C7A C2A 124.8(13) . . ? C9A C8A C13A 118.4(14) . . ? C9A C8A C1A 115(2) . . ? C13A C8A C1A 127(2) . . ? C8A C9A C10A 120.7(13) . . ? C11A C10A C9A 120.7(15) . . ? C12A C11A C10A 118.5(17) . . ? C13A C12A C11A 120.6(14) . . ? C8A C13A C12A 121.1(13) . . ? C15A C14A C19A 117.7(14) . . ? C15A C14A S1A 122.5(13) . . ? C19A C14A S1A 119.8(14) . . ? C14A C15A C16A 122.6(13) . . ? C14A C15A N2A 120.8(17) . . ? C16A C15A N2A 116.5(16) . . ? C15A C16A C17A 119.5(13) . . ? C18A C17A C16A 119.0(14) . . ? C17A C18A C19A 121.0(13) . . ? C14A C19A C18A 120.2(13) . . ? O2A N2A O1A 132(3) . . ? O2A N2A C15A 111(2) . . ? O1A N2A C15A 118(3) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.246 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.040 data_compound_1b _database_code_depnum_ccdc_archive 'CCDC 913179' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H13 N3 O4 S' _chemical_formula_sum 'C19 H13 N3 O4 S' _chemical_formula_weight 379.38 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 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 14.9965(4) _cell_length_b 7.2996(2) _cell_length_c 16.0914(4) _cell_angle_alpha 90.00 _cell_angle_beta 106.510(2) _cell_angle_gamma 90.00 _cell_volume 1688.88(8) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 6979 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour 'pale orange' _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.492 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.224 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.901 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 12806 _diffrn_reflns_av_R_equivalents 0.0558 _diffrn_reflns_av_sigmaI/netI 0.0658 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3868 _reflns_number_gt 2569 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0443P)^2^+0.4715P] 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 3868 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0841 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1096 _refine_ls_wR_factor_gt 0.0956 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 S1 S 0.37694(3) 0.20190(9) 0.35340(3) 0.03745(17) Uani 1 1 d . . . N1 N 0.33371(11) 0.1426(3) 0.43579(10) 0.0314(4) Uani 1 1 d . . . C1 C 0.24583(13) 0.1069(3) 0.41939(12) 0.0266(4) Uani 1 1 d . . . C2 C 0.21360(12) 0.0567(3) 0.49555(11) 0.0267(4) Uani 1 1 d . . . C3 C 0.26665(14) 0.1005(3) 0.57959(12) 0.0336(5) Uani 1 1 d . . . H3A H 0.3226 0.1682 0.5881 0.040 Uiso 1 1 calc R . . C4 C 0.23859(15) 0.0462(3) 0.65052(13) 0.0385(5) Uani 1 1 d . . . H4A H 0.2752 0.0773 0.7073 0.046 Uiso 1 1 calc R . . C5 C 0.15774(15) -0.0530(3) 0.63951(13) 0.0370(5) Uani 1 1 d . . . H5A H 0.1388 -0.0903 0.6885 0.044 Uiso 1 1 calc R . . C6 C 0.10437(14) -0.0978(3) 0.55671(13) 0.0344(5) Uani 1 1 d . . . H6A H 0.0487 -0.1663 0.5488 0.041 Uiso 1 1 calc R . . C7 C 0.13197(13) -0.0427(3) 0.48536(12) 0.0303(5) Uani 1 1 d . . . H7A H 0.0947 -0.0733 0.4288 0.036 Uiso 1 1 calc R . . C8 C 0.17668(12) 0.1125(3) 0.33173(11) 0.0259(4) Uani 1 1 d . . . C9 C 0.09586(13) 0.2162(3) 0.31803(12) 0.0282(4) Uani 1 1 d . . . H9A H 0.0843 0.2818 0.3649 0.034 Uiso 1 1 calc R . . C10 C 0.03215(13) 0.2244(3) 0.23651(12) 0.0319(5) Uani 1 1 d . . . H10A H -0.0229 0.2951 0.2278 0.038 Uiso 1 1 calc R . . C11 C 0.04873(14) 0.1296(3) 0.16779(13) 0.0342(5) Uani 1 1 d . . . H11A H 0.0051 0.1356 0.1120 0.041 Uiso 1 1 calc R . . C12 C 0.12852(14) 0.0265(3) 0.18043(12) 0.0316(5) Uani 1 1 d . . . H12A H 0.1401 -0.0377 0.1332 0.038 Uiso 1 1 calc R . . C13 C 0.19205(13) 0.0163(3) 0.26213(12) 0.0308(5) Uani 1 1 d . . . H13A H 0.2464 -0.0568 0.2707 0.037 Uiso 1 1 calc R . . C14 C 0.49040(13) 0.2587(3) 0.41437(12) 0.0293(5) Uani 1 1 d . . . C15 C 0.55990(13) 0.3040(3) 0.37450(12) 0.0286(5) Uani 1 1 d . . . C16 C 0.64872(13) 0.3564(3) 0.42076(12) 0.0291(5) Uani 1 1 d . . . H16A H 0.6938 0.3881 0.3920 0.035 Uiso 1 1 calc R . . C17 C 0.66970(13) 0.3614(3) 0.50936(12) 0.0279(5) Uani 1 1 d . . . C18 C 0.60555(13) 0.3116(3) 0.55238(12) 0.0309(5) Uani 1 1 d . . . H18A H 0.6226 0.3115 0.6139 0.037 Uiso 1 1 calc R . . C19 C 0.51697(13) 0.2622(3) 0.50551(12) 0.0302(5) Uani 1 1 d . . . H19A H 0.4729 0.2299 0.5353 0.036 Uiso 1 1 calc R . . N2 N 0.54165(12) 0.2910(3) 0.28113(10) 0.0388(5) Uani 1 1 d . . . O1 O 0.46136(11) 0.2712(3) 0.23681(10) 0.0707(7) Uani 1 1 d . . . O2 O 0.60678(11) 0.2963(3) 0.25015(9) 0.0566(5) Uani 1 1 d . . . N3 N 0.76380(11) 0.4159(3) 0.55938(11) 0.0327(4) Uani 1 1 d . . . O3 O 0.81569(9) 0.4791(2) 0.51985(9) 0.0400(4) Uani 1 1 d . . . O4 O 0.78587(10) 0.3925(3) 0.63789(9) 0.0487(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 S1 0.0240(3) 0.0615(4) 0.0251(3) 0.0054(3) 0.00428(19) -0.0045(3) N1 0.0253(8) 0.0405(12) 0.0281(8) 0.0024(8) 0.0071(7) 0.0004(8) C1 0.0247(10) 0.0271(12) 0.0273(9) -0.0006(9) 0.0061(8) 0.0025(9) C2 0.0269(10) 0.0267(12) 0.0261(9) 0.0006(9) 0.0069(8) 0.0044(9) C3 0.0312(11) 0.0380(14) 0.0299(10) -0.0023(10) 0.0062(9) -0.0038(10) C4 0.0442(12) 0.0434(15) 0.0255(10) -0.0045(10) 0.0062(9) 0.0005(11) C5 0.0441(12) 0.0398(14) 0.0305(10) 0.0038(10) 0.0160(9) 0.0055(11) C6 0.0309(10) 0.0364(14) 0.0371(11) 0.0044(10) 0.0119(9) -0.0015(10) C7 0.0287(10) 0.0339(13) 0.0270(9) 0.0000(9) 0.0061(8) -0.0001(9) C8 0.0247(9) 0.0285(12) 0.0244(9) 0.0025(9) 0.0072(8) -0.0022(9) C9 0.0266(10) 0.0308(12) 0.0270(9) -0.0014(9) 0.0075(8) 0.0003(9) C10 0.0269(10) 0.0331(13) 0.0339(11) 0.0040(9) 0.0057(9) 0.0048(9) C11 0.0330(11) 0.0380(14) 0.0276(10) 0.0027(9) 0.0024(9) -0.0044(10) C12 0.0350(11) 0.0335(13) 0.0276(9) -0.0042(9) 0.0112(8) -0.0050(10) C13 0.0274(10) 0.0333(13) 0.0328(10) -0.0007(9) 0.0105(8) 0.0016(9) C14 0.0236(9) 0.0377(13) 0.0257(9) 0.0025(9) 0.0058(8) 0.0031(9) C15 0.0278(10) 0.0364(13) 0.0217(9) 0.0015(9) 0.0070(8) 0.0003(9) C16 0.0268(10) 0.0335(13) 0.0280(9) -0.0023(9) 0.0094(8) -0.0019(9) C17 0.0241(10) 0.0313(13) 0.0263(9) -0.0006(9) 0.0041(8) 0.0019(8) C18 0.0321(10) 0.0383(13) 0.0214(9) 0.0011(9) 0.0064(8) 0.0026(10) C19 0.0270(10) 0.0398(14) 0.0242(9) 0.0043(9) 0.0078(8) 0.0022(9) N2 0.0323(10) 0.0607(14) 0.0242(8) 0.0010(9) 0.0093(8) -0.0092(9) O1 0.0334(9) 0.149(2) 0.0244(8) 0.0037(10) -0.0003(7) -0.0190(11) O2 0.0430(9) 0.1009(16) 0.0306(8) -0.0107(9) 0.0178(7) -0.0182(10) N3 0.0303(9) 0.0344(11) 0.0312(9) -0.0025(8) 0.0051(7) -0.0012(8) O3 0.0321(8) 0.0499(11) 0.0391(8) -0.0032(7) 0.0116(7) -0.0094(7) O4 0.0412(9) 0.0709(13) 0.0262(7) 0.0048(8) -0.0028(7) -0.0101(9) _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 S1 N1 1.6894(16) . ? S1 C14 1.755(2) . ? N1 C1 1.295(2) . ? C1 C2 1.485(3) . ? C1 C8 1.495(3) . ? C2 C7 1.392(3) . ? C2 C3 1.397(3) . ? C3 C4 1.382(3) . ? C4 C5 1.379(3) . ? C5 C6 1.384(3) . ? C6 C7 1.386(3) . ? C8 C9 1.393(3) . ? C8 C13 1.395(3) . ? C9 C10 1.387(3) . ? C10 C11 1.386(3) . ? C11 C12 1.379(3) . ? C12 C13 1.389(3) . ? C14 C19 1.407(3) . ? C14 C15 1.410(3) . ? C15 C16 1.382(3) . ? C15 N2 1.452(2) . ? C16 C17 1.370(3) . ? C17 C18 1.384(3) . ? C17 N3 1.467(2) . ? C18 C19 1.376(3) . ? N2 O2 1.217(2) . ? N2 O1 1.221(2) . ? N3 O4 1.224(2) . ? N3 O3 1.227(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 N1 S1 C14 98.58(9) . . ? C1 N1 S1 119.14(14) . . ? N1 C1 C2 115.62(17) . . ? N1 C1 C8 125.43(17) . . ? C2 C1 C8 118.95(16) . . ? C7 C2 C3 118.21(17) . . ? C7 C2 C1 120.85(17) . . ? C3 C2 C1 120.86(18) . . ? C4 C3 C2 120.71(19) . . ? C5 C4 C3 120.47(19) . . ? C4 C5 C6 119.62(19) . . ? C5 C6 C7 120.1(2) . . ? C6 C7 C2 120.88(18) . . ? C9 C8 C13 118.78(17) . . ? C9 C8 C1 120.21(17) . . ? C13 C8 C1 121.01(17) . . ? C10 C9 C8 120.51(18) . . ? C11 C10 C9 120.09(19) . . ? C12 C11 C10 120.00(19) . . ? C11 C12 C13 120.12(19) . . ? C12 C13 C8 120.48(19) . . ? C19 C14 C15 116.30(17) . . ? C19 C14 S1 121.98(14) . . ? C15 C14 S1 121.72(14) . . ? C16 C15 C14 122.94(17) . . ? C16 C15 N2 116.42(16) . . ? C14 C15 N2 120.61(17) . . ? C17 C16 C15 117.95(17) . . ? C16 C17 C18 121.78(18) . . ? C16 C17 N3 118.60(16) . . ? C18 C17 N3 119.59(16) . . ? C19 C18 C17 119.64(17) . . ? C18 C19 C14 121.31(17) . . ? O2 N2 O1 122.51(16) . . ? O2 N2 C15 118.99(16) . . ? O1 N2 C15 118.48(15) . . ? O4 N3 O3 124.24(17) . . ? O4 N3 C17 117.68(16) . . ? O3 N3 C17 118.08(16) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.296 _refine_diff_density_min -0.439 _refine_diff_density_rms 0.075 data_compound_2a _database_code_depnum_ccdc_archive 'CCDC 913180' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H12 N4 O2 S' _chemical_formula_sum 'C17 H12 N4 O2 S' _chemical_formula_weight 336.37 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 8.8032(2) _cell_length_b 11.8517(2) _cell_length_c 16.3949(4) _cell_angle_alpha 74.4123(9) _cell_angle_beta 76.190(1) _cell_angle_gamma 71.295(1) _cell_volume 1538.63(6) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 9428 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description brick _exptl_crystal_colour orange _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.228 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.916 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 'Nonius Kappa CCD' _diffrn_measurement_method 'phi\omega scans' _diffrn_reflns_number 16668 _diffrn_reflns_av_R_equivalents 0.0409 _diffrn_reflns_av_sigmaI/netI 0.0541 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 26.37 _reflns_number_total 6018 _reflns_number_gt 4459 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0517P)^2^+1.7183P] 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 6018 _refine_ls_number_parameters 433 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0789 _refine_ls_R_factor_gt 0.0501 _refine_ls_wR_factor_ref 0.1291 _refine_ls_wR_factor_gt 0.1098 _refine_ls_goodness_of_fit_ref 0.930 _refine_ls_restrained_S_all 0.930 _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 S1 S 0.22951(9) 0.14480(6) -0.03542(4) 0.03765(18) Uani 1 1 d . . . N1 N 0.3089(3) 0.07636(19) 0.05527(13) 0.0334(5) Uani 1 1 d . . . C1 C 0.3132(3) 0.1411(2) 0.10593(15) 0.0306(6) Uani 1 1 d . . . C2 C 0.3870(3) 0.0732(2) 0.18452(15) 0.0303(5) Uani 1 1 d . . . C3 C 0.4153(3) -0.0523(2) 0.21118(17) 0.0366(6) Uani 1 1 d . . . H3A H 0.3822 -0.0970 0.1817 0.044 Uiso 1 1 calc R . . C4 C 0.4924(3) -0.1106(3) 0.28139(17) 0.0409(6) Uani 1 1 d . . . H4A H 0.5136 -0.1964 0.3010 0.049 Uiso 1 1 calc R . . C5 C 0.5381(3) -0.0424(3) 0.32265(18) 0.0410(7) Uani 1 1 d . . . H5A H 0.5929 -0.0803 0.3705 0.049 Uiso 1 1 calc R . . C6 C 0.5024(4) 0.0815(3) 0.29286(18) 0.0443(7) Uani 1 1 d . . . H6A H 0.5323 0.1281 0.3222 0.053 Uiso 1 1 calc R . . N2 N 0.4280(3) 0.1407(2) 0.22493(14) 0.0387(5) Uani 1 1 d . . . C7 C 0.2525(3) 0.2767(2) 0.09110(15) 0.0310(6) Uani 1 1 d . . . C8 C 0.1416(3) 0.3338(2) 0.15334(16) 0.0350(6) Uani 1 1 d . . . H8A H 0.1072 0.2876 0.2078 0.042 Uiso 1 1 calc R . . C9 C 0.0823(3) 0.4588(2) 0.13474(18) 0.0383(6) Uani 1 1 d . . . H9A H 0.0050 0.5001 0.1759 0.046 Uiso 1 1 calc R . . C10 C 0.1366(3) 0.5231(2) 0.05566(17) 0.0386(6) Uani 1 1 d . . . H10A H 0.0985 0.6094 0.0414 0.046 Uiso 1 1 calc R . . C11 C 0.2472(4) 0.4593(3) -0.00217(18) 0.0454(7) Uani 1 1 d . . . H11A H 0.2848 0.5041 -0.0565 0.054 Uiso 1 1 calc R . . N3 N 0.3049(3) 0.3380(2) 0.01361(14) 0.0398(5) Uani 1 1 d . . . C12 C 0.2136(3) 0.0126(2) -0.05956(15) 0.0348(6) Uani 1 1 d . . . C13 C 0.2990(3) -0.1044(3) -0.02306(17) 0.0387(6) Uani 1 1 d . . . H13A H 0.3652 -0.1144 0.0178 0.046 Uiso 1 1 calc R . . C14 C 0.2890(4) -0.2065(3) -0.04536(19) 0.0460(7) Uani 1 1 d . . . H14A H 0.3498 -0.2851 -0.0203 0.055 Uiso 1 1 calc R . . C15 C 0.1914(4) -0.1950(3) -0.1037(2) 0.0542(9) Uani 1 1 d . . . H15A H 0.1868 -0.2653 -0.1194 0.065 Uiso 1 1 calc R . . C16 C 0.1017(4) -0.0820(3) -0.13873(18) 0.0513(8) Uani 1 1 d . . . H16A H 0.0319 -0.0735 -0.1775 0.062 Uiso 1 1 calc R . . C17 C 0.1135(3) 0.0204(3) -0.11715(16) 0.0417(7) Uani 1 1 d . . . N4 N 0.0144(3) 0.1379(3) -0.15539(15) 0.0539(7) Uani 1 1 d . . . O1 O -0.1079(3) 0.1420(3) -0.18115(15) 0.0773(8) Uani 1 1 d . . . O2 O 0.0576(3) 0.2289(2) -0.16020(15) 0.0660(7) Uani 1 1 d . . . S2 S 0.06859(8) 0.33366(6) 0.39390(4) 0.03201(17) Uani 1 1 d . . . N5 N -0.0940(2) 0.40801(19) 0.34437(13) 0.0313(5) Uani 1 1 d . . . C18 C -0.1873(3) 0.3478(2) 0.33720(15) 0.0291(5) Uani 1 1 d . . . C19 C -0.3267(3) 0.4178(2) 0.29098(16) 0.0309(5) Uani 1 1 d . . . C20 C -0.3547(4) 0.5420(2) 0.25673(19) 0.0433(7) Uani 1 1 d . . . H20A H -0.2876 0.5858 0.2644 0.052 Uiso 1 1 calc R . . C21 C -0.4817(4) 0.6005(3) 0.2114(2) 0.0495(8) Uani 1 1 d . . . H21A H -0.5028 0.6851 0.1867 0.059 Uiso 1 1 calc R . . C22 C -0.5774(3) 0.5338(3) 0.20255(18) 0.0422(7) Uani 1 1 d . . . H22A H -0.6668 0.5721 0.1726 0.051 Uiso 1 1 calc R . . C23 C -0.5413(3) 0.4112(3) 0.23787(18) 0.0423(7) Uani 1 1 d . . . H23A H -0.6068 0.3657 0.2308 0.051 Uiso 1 1 calc R . . N6 N -0.4181(3) 0.3525(2) 0.28186(15) 0.0388(5) Uani 1 1 d . . . C24 C -0.1608(3) 0.2134(2) 0.37016(15) 0.0293(5) Uani 1 1 d . . . C25 C -0.2698(3) 0.1660(3) 0.43607(17) 0.0398(6) Uani 1 1 d . . . H25A H -0.3664 0.2183 0.4606 0.048 Uiso 1 1 calc R . . C26 C -0.2351(3) 0.0414(3) 0.46516(18) 0.0430(7) Uani 1 1 d . . . H26A H -0.3074 0.0066 0.5102 0.052 Uiso 1 1 calc R . . C27 C -0.0948(3) -0.0315(2) 0.42821(17) 0.0394(6) Uani 1 1 d . . . H27A H -0.0684 -0.1176 0.4470 0.047 Uiso 1 1 calc R . . C28 C 0.0070(4) 0.0227(2) 0.36321(18) 0.0413(7) Uani 1 1 d . . . H28A H 0.1039 -0.0283 0.3377 0.050 Uiso 1 1 calc R . . N7 N -0.0230(3) 0.14365(19) 0.33397(14) 0.0361(5) Uani 1 1 d . . . C29 C 0.1198(3) 0.4634(2) 0.39998(15) 0.0285(5) Uani 1 1 d . . . C30 C 0.0444(3) 0.5804(2) 0.35766(16) 0.0356(6) Uani 1 1 d . . . H30A H -0.0388 0.5909 0.3263 0.043 Uiso 1 1 calc R . . C31 C 0.0884(4) 0.6808(3) 0.36050(18) 0.0438(7) Uani 1 1 d . . . H31A H 0.0346 0.7592 0.3315 0.053 Uiso 1 1 calc R . . C32 C 0.2105(4) 0.6687(3) 0.40527(18) 0.0435(7) Uani 1 1 d . . . H32A H 0.2426 0.7381 0.4052 0.052 Uiso 1 1 calc R . . C33 C 0.2839(3) 0.5565(3) 0.44925(17) 0.0378(6) Uani 1 1 d . . . H33A H 0.3651 0.5474 0.4815 0.045 Uiso 1 1 calc R . . C34 C 0.2388(3) 0.4554(2) 0.44657(15) 0.0302(5) Uani 1 1 d . . . N8 N 0.3177(3) 0.3396(2) 0.49572(14) 0.0360(5) Uani 1 1 d . . . O3 O 0.3002(2) 0.24620(17) 0.48400(13) 0.0459(5) Uani 1 1 d . . . O4 O 0.4010(3) 0.3373(2) 0.54715(14) 0.0538(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 S1 0.0478(4) 0.0373(4) 0.0306(3) -0.0069(3) -0.0117(3) -0.0118(3) N1 0.0364(12) 0.0361(12) 0.0287(11) -0.0070(9) -0.0062(9) -0.0106(10) C1 0.0293(13) 0.0359(14) 0.0284(13) -0.0067(11) -0.0036(10) -0.0123(11) C2 0.0293(13) 0.0336(14) 0.0292(13) -0.0077(10) -0.0036(10) -0.0101(11) C3 0.0456(16) 0.0310(14) 0.0369(14) -0.0056(11) -0.0124(12) -0.0127(12) C4 0.0503(17) 0.0319(15) 0.0384(15) -0.0003(12) -0.0118(13) -0.0112(13) C5 0.0466(17) 0.0419(16) 0.0360(15) -0.0010(12) -0.0167(12) -0.0128(13) C6 0.0586(19) 0.0397(16) 0.0432(16) -0.0062(13) -0.0223(14) -0.0169(14) N2 0.0506(14) 0.0340(12) 0.0372(12) -0.0036(10) -0.0166(11) -0.0160(11) C7 0.0324(14) 0.0340(14) 0.0302(13) -0.0038(11) -0.0090(10) -0.0138(11) C8 0.0354(14) 0.0350(15) 0.0326(14) -0.0034(11) -0.0047(11) -0.0108(12) C9 0.0390(15) 0.0348(15) 0.0408(15) -0.0104(12) -0.0059(12) -0.0081(12) C10 0.0398(15) 0.0294(14) 0.0445(16) -0.0036(12) -0.0123(12) -0.0065(12) C11 0.0567(19) 0.0361(16) 0.0376(15) 0.0028(12) -0.0050(13) -0.0156(14) N3 0.0478(14) 0.0349(13) 0.0327(12) -0.0024(10) -0.0043(10) -0.0115(11) C12 0.0376(15) 0.0456(16) 0.0249(13) -0.0115(11) 0.0033(11) -0.0191(13) C13 0.0361(15) 0.0429(16) 0.0389(15) -0.0119(13) -0.0015(12) -0.0138(13) C14 0.0458(17) 0.0479(18) 0.0494(17) -0.0166(14) 0.0034(14) -0.0224(14) C15 0.070(2) 0.062(2) 0.0453(18) -0.0211(16) 0.0046(16) -0.0404(19) C16 0.063(2) 0.077(2) 0.0304(15) -0.0130(15) -0.0025(14) -0.0436(19) C17 0.0458(16) 0.0579(19) 0.0252(13) -0.0032(12) -0.0034(12) -0.0257(15) N4 0.0637(18) 0.074(2) 0.0297(13) -0.0001(12) -0.0162(12) -0.0286(16) O1 0.0715(17) 0.108(2) 0.0586(15) 0.0155(14) -0.0347(13) -0.0426(16) O2 0.0950(19) 0.0581(15) 0.0533(14) 0.0013(11) -0.0408(13) -0.0222(14) S2 0.0313(3) 0.0285(3) 0.0392(4) -0.0029(3) -0.0129(3) -0.0106(3) N5 0.0287(11) 0.0324(12) 0.0346(12) -0.0077(9) -0.0085(9) -0.0079(9) C18 0.0275(13) 0.0315(13) 0.0296(13) -0.0111(10) -0.0037(10) -0.0067(11) C19 0.0294(13) 0.0310(14) 0.0354(14) -0.0132(11) -0.0085(10) -0.0051(11) C20 0.0450(17) 0.0300(15) 0.0619(19) -0.0131(13) -0.0250(14) -0.0049(12) C21 0.0556(19) 0.0308(15) 0.066(2) -0.0120(14) -0.0302(16) -0.0010(14) C22 0.0380(15) 0.0439(17) 0.0475(17) -0.0155(13) -0.0194(13) -0.0011(13) C23 0.0388(16) 0.0409(16) 0.0521(17) -0.0083(13) -0.0192(13) -0.0104(13) N6 0.0355(12) 0.0376(13) 0.0486(14) -0.0080(10) -0.0165(10) -0.0114(10) C24 0.0274(13) 0.0311(13) 0.0321(13) -0.0074(10) -0.0099(10) -0.0076(11) C25 0.0286(14) 0.0463(17) 0.0420(15) -0.0090(13) -0.0045(11) -0.0081(12) C26 0.0428(16) 0.0473(17) 0.0392(15) 0.0005(13) -0.0057(12) -0.0215(14) C27 0.0497(17) 0.0305(14) 0.0407(15) -0.0009(12) -0.0138(13) -0.0152(13) C28 0.0456(16) 0.0302(15) 0.0456(16) -0.0103(12) -0.0039(13) -0.0079(12) N7 0.0366(12) 0.0295(12) 0.0394(12) -0.0060(10) -0.0020(10) -0.0092(10) C29 0.0288(13) 0.0328(14) 0.0257(12) -0.0057(10) -0.0028(10) -0.0125(11) C30 0.0463(16) 0.0316(14) 0.0303(13) -0.0032(11) -0.0120(11) -0.0113(12) C31 0.065(2) 0.0328(15) 0.0378(15) -0.0031(12) -0.0143(14) -0.0182(14) C32 0.0550(18) 0.0399(16) 0.0450(16) -0.0118(13) -0.0062(14) -0.0249(14) C33 0.0326(14) 0.0436(16) 0.0440(15) -0.0137(13) -0.0076(12) -0.0150(12) C34 0.0270(13) 0.0347(14) 0.0290(13) -0.0081(11) -0.0030(10) -0.0089(11) N8 0.0276(12) 0.0406(13) 0.0421(13) -0.0094(10) -0.0101(10) -0.0086(10) O3 0.0441(12) 0.0349(11) 0.0637(13) -0.0015(9) -0.0252(10) -0.0131(9) O4 0.0502(13) 0.0553(13) 0.0634(14) -0.0149(11) -0.0345(11) -0.0045(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 S1 N1 1.686(2) . ? S1 C12 1.769(3) . ? N1 C1 1.287(3) . ? C1 C7 1.493(4) . ? C1 C2 1.496(3) . ? C2 N2 1.339(3) . ? C2 C3 1.389(4) . ? C3 C4 1.382(4) . ? C4 C5 1.381(4) . ? C5 C6 1.374(4) . ? C6 N2 1.340(3) . ? C7 N3 1.339(3) . ? C7 C8 1.387(4) . ? C8 C9 1.377(4) . ? C9 C10 1.377(4) . ? C10 C11 1.375(4) . ? C11 N3 1.336(4) . ? C12 C13 1.395(4) . ? C12 C17 1.405(4) . ? C13 C14 1.388(4) . ? C14 C15 1.386(4) . ? C15 C16 1.368(5) . ? C16 C17 1.392(4) . ? C17 N4 1.451(4) . ? N4 O1 1.230(3) . ? N4 O2 1.233(3) . ? S2 N5 1.687(2) . ? S2 C29 1.768(2) . ? N5 C18 1.290(3) . ? C18 C19 1.491(3) . ? C18 C24 1.498(3) . ? C19 N6 1.336(3) . ? C19 C20 1.390(4) . ? C20 C21 1.381(4) . ? C21 C22 1.379(4) . ? C22 C23 1.374(4) . ? C23 N6 1.341(3) . ? C24 N7 1.335(3) . ? C24 C25 1.389(4) . ? C25 C26 1.380(4) . ? C26 C27 1.370(4) . ? C27 C28 1.378(4) . ? C28 N7 1.342(3) . ? C29 C30 1.399(4) . ? C29 C34 1.403(3) . ? C30 C31 1.378(4) . ? C31 C32 1.392(4) . ? C32 C33 1.365(4) . ? C33 C34 1.392(3) . ? C34 N8 1.441(3) . ? N8 O4 1.233(3) . ? N8 O3 1.234(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 N1 S1 C12 97.43(12) . . ? C1 N1 S1 119.83(19) . . ? N1 C1 C7 124.9(2) . . ? N1 C1 C2 116.4(2) . . ? C7 C1 C2 118.7(2) . . ? N2 C2 C3 123.0(2) . . ? N2 C2 C1 115.6(2) . . ? C3 C2 C1 121.4(2) . . ? C4 C3 C2 118.6(2) . . ? C5 C4 C3 119.0(3) . . ? C6 C5 C4 118.4(3) . . ? N2 C6 C5 124.0(3) . . ? C2 N2 C6 117.0(2) . . ? N3 C7 C8 122.8(2) . . ? N3 C7 C1 116.2(2) . . ? C8 C7 C1 121.0(2) . . ? C9 C8 C7 118.7(2) . . ? C8 C9 C10 119.1(3) . . ? C11 C10 C9 118.4(3) . . ? N3 C11 C10 123.8(3) . . ? C11 N3 C7 117.2(2) . . ? C13 C12 C17 116.3(2) . . ? C13 C12 S1 122.3(2) . . ? C17 C12 S1 121.4(2) . . ? C14 C13 C12 121.2(3) . . ? C15 C14 C13 120.8(3) . . ? C16 C15 C14 119.7(3) . . ? C15 C16 C17 119.5(3) . . ? C16 C17 C12 122.5(3) . . ? C16 C17 N4 117.2(3) . . ? C12 C17 N4 120.3(3) . . ? O1 N4 O2 123.3(3) . . ? O1 N4 C17 118.8(3) . . ? O2 N4 C17 117.9(3) . . ? N5 S2 C29 97.39(11) . . ? C18 N5 S2 119.28(18) . . ? N5 C18 C19 116.9(2) . . ? N5 C18 C24 124.1(2) . . ? C19 C18 C24 119.0(2) . . ? N6 C19 C20 122.6(2) . . ? N6 C19 C18 115.7(2) . . ? C20 C19 C18 121.7(2) . . ? C21 C20 C19 118.8(3) . . ? C22 C21 C20 118.8(3) . . ? C23 C22 C21 118.9(3) . . ? N6 C23 C22 123.3(3) . . ? C19 N6 C23 117.6(2) . . ? N7 C24 C25 122.9(2) . . ? N7 C24 C18 115.3(2) . . ? C25 C24 C18 121.8(2) . . ? C26 C25 C24 118.7(3) . . ? C27 C26 C25 119.2(3) . . ? C26 C27 C28 118.5(3) . . ? N7 C28 C27 123.6(3) . . ? C24 N7 C28 117.1(2) . . ? C30 C29 C34 116.1(2) . . ? C30 C29 S2 121.64(19) . . ? C34 C29 S2 122.30(19) . . ? C31 C30 C29 121.4(3) . . ? C30 C31 C32 120.9(3) . . ? C33 C32 C31 119.4(2) . . ? C32 C33 C34 119.5(2) . . ? C33 C34 C29 122.7(2) . . ? C33 C34 N8 117.1(2) . . ? C29 C34 N8 120.2(2) . . ? O4 N8 O3 122.5(2) . . ? O4 N8 C34 119.0(2) . . ? O3 N8 C34 118.5(2) . . ? _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.956 _refine_diff_density_max 0.224 _refine_diff_density_min -0.341 _refine_diff_density_rms 0.055 data_compound_3a _database_code_depnum_ccdc_archive 'CCDC 913181' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H12 N2 O2 S' _chemical_formula_sum 'C19 H12 N2 O2 S' _chemical_formula_weight 332.37 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 7.3115(2) _cell_length_b 9.4716(3) _cell_length_c 12.3682(4) _cell_angle_alpha 101.868(1) _cell_angle_beta 98.333(2) _cell_angle_gamma 112.163(2) _cell_volume 752.52(4) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 2058 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.467 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.229 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.906 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 7512 _diffrn_reflns_av_R_equivalents 0.0483 _diffrn_reflns_av_sigmaI/netI 0.0676 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 26.37 _reflns_number_total 3072 _reflns_number_gt 2266 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0379P)^2^+0.3418P] 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 3072 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0773 _refine_ls_R_factor_gt 0.0452 _refine_ls_wR_factor_ref 0.1096 _refine_ls_wR_factor_gt 0.0967 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.14934(8) 0.40554(7) -0.08738(5) 0.02787(17) Uani 1 1 d . . . N1 N 0.2941(3) 0.5484(2) 0.03295(15) 0.0271(4) Uani 1 1 d . . . C1 C 0.3675(3) 0.5141(3) 0.12034(18) 0.0251(5) Uani 1 1 d . . . C2 C 0.3561(3) 0.3637(3) 0.14378(18) 0.0251(5) Uani 1 1 d . . . C3 C 0.2642(3) 0.2075(3) 0.0762(2) 0.0319(5) Uani 1 1 d . . . H3A H 0.1988 0.1823 -0.0018 0.038 Uiso 1 1 calc R . . C4 C 0.2692(3) 0.0881(3) 0.1242(2) 0.0359(6) Uani 1 1 d . . . H4A H 0.2049 -0.0196 0.0788 0.043 Uiso 1 1 calc R . . C5 C 0.3672(4) 0.1248(3) 0.2376(2) 0.0353(6) Uani 1 1 d . . . H5A H 0.3669 0.0416 0.2695 0.042 Uiso 1 1 calc R . . C6 C 0.4658(3) 0.2811(3) 0.3053(2) 0.0300(5) Uani 1 1 d . . . H6A H 0.5369 0.3057 0.3822 0.036 Uiso 1 1 calc R . . C7 C 0.4587(3) 0.4011(3) 0.25878(18) 0.0260(5) Uani 1 1 d . . . C8 C 0.5407(3) 0.5728(3) 0.31062(18) 0.0249(5) Uani 1 1 d . . . C9 C 0.6496(3) 0.6688(3) 0.41993(19) 0.0325(5) Uani 1 1 d . . . H9A H 0.6875 0.6242 0.4767 0.039 Uiso 1 1 calc R . . C10 C 0.7021(4) 0.8306(3) 0.4451(2) 0.0370(6) Uani 1 1 d . . . H10A H 0.7769 0.8970 0.5197 0.044 Uiso 1 1 calc R . . C11 C 0.6473(4) 0.8976(3) 0.3628(2) 0.0365(6) Uani 1 1 d . . . H11A H 0.6836 1.0087 0.3819 0.044 Uiso 1 1 calc R . . C12 C 0.5398(3) 0.8026(3) 0.25306(19) 0.0310(5) Uani 1 1 d . . . H12A H 0.5035 0.8477 0.1962 0.037 Uiso 1 1 calc R . . C13 C 0.4866(3) 0.6413(3) 0.22802(18) 0.0249(5) Uani 1 1 d . . . C14 C 0.1057(3) 0.5286(3) -0.16819(18) 0.0253(5) Uani 1 1 d . . . C15 C -0.0017(3) 0.4676(3) -0.28342(18) 0.0285(5) Uani 1 1 d . . . N2 N -0.0834(3) 0.2993(3) -0.34083(17) 0.0361(5) Uani 1 1 d . . . O1 O -0.0664(3) 0.2104(2) -0.28395(14) 0.0426(4) Uani 1 1 d . . . O2 O -0.1648(3) 0.2510(2) -0.44361(15) 0.0564(5) Uani 1 1 d . . . C16 C -0.0341(3) 0.5644(3) -0.3472(2) 0.0343(6) Uani 1 1 d . . . H16A H -0.1067 0.5195 -0.4251 0.041 Uiso 1 1 calc R . . C17 C 0.0387(3) 0.7251(3) -0.2979(2) 0.0360(6) Uani 1 1 d . . . H17A H 0.0157 0.7919 -0.3408 0.043 Uiso 1 1 calc R . . C18 C 0.1464(3) 0.7886(3) -0.1846(2) 0.0346(6) Uani 1 1 d . . . H18A H 0.1983 0.8998 -0.1502 0.041 Uiso 1 1 calc R . . C19 C 0.1794(3) 0.6926(3) -0.12090(19) 0.0302(5) Uani 1 1 d . . . H19A H 0.2537 0.7392 -0.0434 0.036 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 S1 0.0296(3) 0.0293(3) 0.0247(3) 0.0083(2) 0.0048(2) 0.0127(2) N1 0.0272(10) 0.0318(12) 0.0233(10) 0.0086(9) 0.0058(8) 0.0130(9) C1 0.0243(11) 0.0281(13) 0.0256(12) 0.0087(10) 0.0085(9) 0.0126(10) C2 0.0238(11) 0.0262(13) 0.0274(12) 0.0083(10) 0.0072(9) 0.0121(10) C3 0.0285(12) 0.0311(14) 0.0318(13) 0.0038(11) 0.0021(10) 0.0123(11) C4 0.0348(13) 0.0249(13) 0.0437(15) 0.0044(11) 0.0060(11) 0.0119(11) C5 0.0370(13) 0.0324(15) 0.0455(15) 0.0188(12) 0.0147(12) 0.0184(12) C6 0.0318(12) 0.0338(14) 0.0295(12) 0.0122(11) 0.0082(10) 0.0172(11) C7 0.0243(11) 0.0285(13) 0.0282(12) 0.0093(10) 0.0087(9) 0.0128(10) C8 0.0248(11) 0.0275(13) 0.0248(12) 0.0089(10) 0.0078(9) 0.0119(10) C9 0.0349(13) 0.0354(15) 0.0266(13) 0.0080(11) 0.0050(10) 0.0156(11) C10 0.0384(13) 0.0359(15) 0.0249(13) -0.0010(11) -0.0001(11) 0.0107(12) C11 0.0424(14) 0.0273(14) 0.0349(14) 0.0052(11) 0.0074(11) 0.0120(11) C12 0.0361(13) 0.0301(14) 0.0289(13) 0.0101(11) 0.0076(10) 0.0155(11) C13 0.0241(11) 0.0265(13) 0.0249(12) 0.0073(9) 0.0065(9) 0.0112(10) C14 0.0222(11) 0.0325(13) 0.0230(12) 0.0095(10) 0.0066(9) 0.0123(10) C15 0.0248(11) 0.0339(14) 0.0260(12) 0.0098(10) 0.0062(9) 0.0106(10) N2 0.0316(11) 0.0386(13) 0.0296(11) 0.0061(10) 0.0031(9) 0.0092(10) O1 0.0476(10) 0.0341(11) 0.0364(10) 0.0083(8) 0.0026(8) 0.0106(9) O2 0.0685(13) 0.0524(13) 0.0274(10) 0.0002(9) -0.0068(9) 0.0157(11) C16 0.0263(12) 0.0481(17) 0.0261(13) 0.0129(12) 0.0029(10) 0.0133(11) C17 0.0335(13) 0.0456(17) 0.0354(14) 0.0223(13) 0.0081(11) 0.0179(12) C18 0.0348(13) 0.0342(15) 0.0402(15) 0.0145(12) 0.0124(11) 0.0172(11) C19 0.0301(12) 0.0348(15) 0.0265(12) 0.0094(11) 0.0076(10) 0.0140(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 S1 N1 1.673(2) . ? S1 C14 1.768(2) . ? N1 C1 1.292(3) . ? C1 C13 1.482(3) . ? C1 C2 1.485(3) . ? C2 C3 1.385(3) . ? C2 C7 1.412(3) . ? C3 C4 1.390(3) . ? C4 C5 1.387(3) . ? C5 C6 1.386(3) . ? C6 C7 1.389(3) . ? C7 C8 1.463(3) . ? C8 C9 1.387(3) . ? C8 C13 1.404(3) . ? C9 C10 1.385(3) . ? C10 C11 1.392(3) . ? C11 C12 1.388(3) . ? C12 C13 1.379(3) . ? C14 C19 1.396(3) . ? C14 C15 1.406(3) . ? C15 C16 1.388(3) . ? C15 N2 1.448(3) . ? N2 O2 1.231(3) . ? N2 O1 1.231(2) . ? C16 C17 1.373(4) . ? C17 C18 1.386(3) . ? C18 C19 1.382(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 N1 S1 C14 97.92(10) . . ? C1 N1 S1 120.90(16) . . ? N1 C1 C13 120.1(2) . . ? N1 C1 C2 134.1(2) . . ? C13 C1 C2 105.81(18) . . ? C3 C2 C7 120.2(2) . . ? C3 C2 C1 132.0(2) . . ? C7 C2 C1 107.79(19) . . ? C2 C3 C4 119.1(2) . . ? C5 C4 C3 120.6(2) . . ? C6 C5 C4 121.0(2) . . ? C5 C6 C7 118.9(2) . . ? C6 C7 C2 120.2(2) . . ? C6 C7 C8 130.5(2) . . ? C2 C7 C8 109.25(18) . . ? C9 C8 C13 119.5(2) . . ? C9 C8 C7 132.3(2) . . ? C13 C8 C7 108.19(19) . . ? C10 C9 C8 119.0(2) . . ? C9 C10 C11 121.1(2) . . ? C12 C11 C10 120.2(2) . . ? C13 C12 C11 118.8(2) . . ? C12 C13 C8 121.4(2) . . ? C12 C13 C1 129.64(19) . . ? C8 C13 C1 108.95(19) . . ? C19 C14 C15 116.4(2) . . ? C19 C14 S1 121.45(17) . . ? C15 C14 S1 122.10(18) . . ? C16 C15 C14 122.1(2) . . ? C16 C15 N2 117.0(2) . . ? C14 C15 N2 120.8(2) . . ? O2 N2 O1 122.8(2) . . ? O2 N2 C15 119.3(2) . . ? O1 N2 C15 117.92(19) . . ? C17 C16 C15 120.0(2) . . ? C16 C17 C18 119.1(2) . . ? C19 C18 C17 121.1(2) . . ? C18 C19 C14 121.3(2) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.359 _refine_diff_density_min -0.326 _refine_diff_density_rms 0.090 data_compound_3b _database_code_depnum_ccdc_archive 'CCDC 913182' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H11 N3 O4 S' _chemical_formula_sum 'C19 H11 N3 O4 S' _chemical_formula_weight 377.37 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 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 13.1797(4) _cell_length_b 7.9049(2) _cell_length_c 15.5730(5) _cell_angle_alpha 90.00 _cell_angle_beta 93.866(1) _cell_angle_gamma 90.00 _cell_volume 1618.77(8) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 5387 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.548 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.234 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.894 _exptl_absorpt_correction_T_max 0.976 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 'Nonius Kappa CCD' _diffrn_measurement_method 'thin slice \w and \f scans' _diffrn_reflns_number 9120 _diffrn_reflns_av_R_equivalents 0.0419 _diffrn_reflns_av_sigmaI/netI 0.0581 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3702 _reflns_number_gt 2772 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0506P)^2^+0.1462P] 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 0.016(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3702 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0645 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.1050 _refine_ls_wR_factor_gt 0.0971 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.42266(3) 0.13073(5) 0.57282(3) 0.02830(15) Uani 1 1 d . . . N1 N 0.37661(10) 0.15411(17) 0.47016(9) 0.0265(3) Uani 1 1 d . . . C1 C 0.28978(12) 0.0833(2) 0.44862(10) 0.0241(4) Uani 1 1 d . . . C2 C 0.21783(12) -0.01742(19) 0.49742(11) 0.0242(4) Uani 1 1 d . . . C3 C 0.21933(13) -0.0667(2) 0.58306(11) 0.0292(4) Uani 1 1 d . . . H3A H 0.2734 -0.0330 0.6228 0.035 Uiso 1 1 calc R . . C4 C 0.14027(14) -0.1664(2) 0.60957(12) 0.0344(4) Uani 1 1 d . . . H4A H 0.1405 -0.2005 0.6681 0.041 Uiso 1 1 calc R . . C5 C 0.06162(13) -0.2166(2) 0.55228(12) 0.0333(4) Uani 1 1 d . . . H5A H 0.0090 -0.2861 0.5716 0.040 Uiso 1 1 calc R . . C6 C 0.05849(13) -0.1668(2) 0.46697(12) 0.0302(4) Uani 1 1 d . . . H6A H 0.0039 -0.2008 0.4279 0.036 Uiso 1 1 calc R . . C7 C 0.13639(12) -0.0665(2) 0.43940(11) 0.0245(4) Uani 1 1 d . . . C8 C 0.15209(12) 0.0044(2) 0.35397(11) 0.0262(4) Uani 1 1 d . . . C9 C 0.09298(13) -0.0040(2) 0.27723(11) 0.0327(4) Uani 1 1 d . . . H9A H 0.0299 -0.0626 0.2738 0.039 Uiso 1 1 calc R . . C10 C 0.12820(15) 0.0754(2) 0.20528(12) 0.0372(4) Uani 1 1 d . . . H10A H 0.0889 0.0701 0.1519 0.045 Uiso 1 1 calc R . . C11 C 0.21983(14) 0.1621(2) 0.21040(12) 0.0367(4) Uani 1 1 d . . . H11A H 0.2424 0.2152 0.1604 0.044 Uiso 1 1 calc R . . C12 C 0.27916(13) 0.1729(2) 0.28736(11) 0.0321(4) Uani 1 1 d . . . H12A H 0.3419 0.2326 0.2907 0.038 Uiso 1 1 calc R . . C13 C 0.24413(12) 0.0938(2) 0.35911(11) 0.0252(4) Uani 1 1 d . . . C14 C 0.53629(12) 0.2459(2) 0.57043(10) 0.0234(3) Uani 1 1 d . . . C15 C 0.60112(12) 0.2680(2) 0.64498(10) 0.0253(4) Uani 1 1 d . . . C16 C 0.69078(12) 0.3582(2) 0.64488(11) 0.0264(4) Uani 1 1 d . . . H16A H 0.7333 0.3716 0.6961 0.032 Uiso 1 1 calc R . . C17 C 0.71679(12) 0.4277(2) 0.56882(11) 0.0246(4) Uani 1 1 d . . . C18 C 0.65589(12) 0.4099(2) 0.49330(11) 0.0257(4) Uani 1 1 d . . . H18A H 0.6755 0.4594 0.4414 0.031 Uiso 1 1 calc R . . C19 C 0.56667(12) 0.3196(2) 0.49444(10) 0.0252(4) Uani 1 1 d . . . H19A H 0.5249 0.3069 0.4427 0.030 Uiso 1 1 calc R . . N2 N 0.57684(11) 0.19344(19) 0.72691(9) 0.0324(4) Uani 1 1 d . . . O1 O 0.50075(10) 0.10397(18) 0.72767(8) 0.0458(4) Uani 1 1 d . . . O2 O 0.63300(11) 0.2210(2) 0.79085(8) 0.0508(4) Uani 1 1 d . . . N3 N 0.81370(10) 0.52034(18) 0.56819(10) 0.0294(3) Uani 1 1 d . . . O3 O 0.87130(9) 0.51579(17) 0.63340(8) 0.0404(3) Uani 1 1 d . . . O4 O 0.83166(9) 0.59662(16) 0.50243(8) 0.0386(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 S1 0.0206(2) 0.0352(3) 0.0290(2) -0.00108(19) 0.00079(16) -0.00584(17) N1 0.0207(7) 0.0280(7) 0.0308(8) -0.0030(6) 0.0010(6) -0.0011(6) C1 0.0212(8) 0.0217(8) 0.0290(9) -0.0019(7) -0.0003(7) 0.0004(6) C2 0.0203(8) 0.0222(8) 0.0300(9) -0.0011(7) 0.0002(7) 0.0007(6) C3 0.0258(9) 0.0279(9) 0.0331(10) 0.0015(8) -0.0035(7) -0.0030(7) C4 0.0325(10) 0.0351(10) 0.0356(10) 0.0077(8) 0.0023(8) -0.0044(8) C5 0.0238(9) 0.0289(9) 0.0478(11) 0.0058(9) 0.0055(8) -0.0047(7) C6 0.0213(8) 0.0273(9) 0.0414(10) -0.0025(8) -0.0023(7) -0.0024(7) C7 0.0198(8) 0.0217(8) 0.0317(9) -0.0035(7) -0.0006(7) 0.0013(6) C8 0.0240(9) 0.0240(8) 0.0304(9) -0.0038(7) 0.0000(7) 0.0029(6) C9 0.0269(9) 0.0336(10) 0.0365(10) -0.0044(8) -0.0053(8) -0.0010(7) C10 0.0421(11) 0.0374(10) 0.0309(10) -0.0031(8) -0.0069(8) 0.0040(8) C11 0.0426(11) 0.0371(10) 0.0306(10) 0.0031(8) 0.0029(8) 0.0017(8) C12 0.0308(10) 0.0300(9) 0.0356(10) -0.0015(8) 0.0041(8) -0.0019(7) C13 0.0223(8) 0.0224(8) 0.0306(9) -0.0017(7) -0.0004(7) 0.0022(6) C14 0.0196(8) 0.0233(8) 0.0274(8) -0.0042(7) 0.0018(6) 0.0009(6) C15 0.0239(8) 0.0267(8) 0.0255(8) -0.0032(7) 0.0021(7) 0.0010(7) C16 0.0230(8) 0.0283(8) 0.0271(9) -0.0060(7) -0.0031(7) 0.0004(7) C17 0.0180(8) 0.0230(8) 0.0327(9) -0.0056(7) 0.0020(7) -0.0010(6) C18 0.0244(9) 0.0252(8) 0.0275(9) -0.0015(7) 0.0025(7) 0.0001(6) C19 0.0229(8) 0.0275(8) 0.0250(8) -0.0028(7) -0.0009(6) 0.0012(7) N2 0.0300(8) 0.0396(9) 0.0273(8) -0.0014(7) 0.0007(6) -0.0040(7) O1 0.0356(8) 0.0662(10) 0.0356(7) 0.0076(7) 0.0016(6) -0.0205(7) O2 0.0524(9) 0.0713(10) 0.0269(7) 0.0041(7) -0.0105(6) -0.0214(8) N3 0.0223(8) 0.0280(8) 0.0376(9) -0.0061(7) 0.0011(7) -0.0018(6) O3 0.0276(7) 0.0481(8) 0.0440(8) -0.0034(6) -0.0075(6) -0.0098(6) O4 0.0323(7) 0.0422(7) 0.0418(8) 0.0030(6) 0.0061(6) -0.0115(6) _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 S1 N1 1.6815(15) . ? S1 C14 1.7551(16) . ? N1 C1 1.298(2) . ? C1 C13 1.483(2) . ? C1 C2 1.486(2) . ? C2 C3 1.388(2) . ? C2 C7 1.410(2) . ? C3 C4 1.391(2) . ? C4 C5 1.379(2) . ? C5 C6 1.384(3) . ? C6 C7 1.388(2) . ? C7 C8 1.471(2) . ? C8 C9 1.383(2) . ? C8 C13 1.402(2) . ? C9 C10 1.391(3) . ? C10 C11 1.387(3) . ? C11 C12 1.389(2) . ? C12 C13 1.386(2) . ? C14 C19 1.401(2) . ? C14 C15 1.405(2) . ? C15 C16 1.380(2) . ? C15 N2 1.460(2) . ? C16 C17 1.370(2) . ? C17 C18 1.386(2) . ? C17 N3 1.473(2) . ? C18 C19 1.377(2) . ? N2 O2 1.2196(18) . ? N2 O1 1.2278(18) . ? N3 O4 1.2252(18) . ? N3 O3 1.2268(18) . ? 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 N1 S1 C14 100.17(8) . . ? C1 N1 S1 117.00(12) . . ? N1 C1 C13 120.91(15) . . ? N1 C1 C2 132.92(15) . . ? C13 C1 C2 106.16(14) . . ? C3 C2 C7 119.94(15) . . ? C3 C2 C1 132.34(15) . . ? C7 C2 C1 107.72(14) . . ? C2 C3 C4 118.80(16) . . ? C5 C4 C3 121.08(17) . . ? C4 C5 C6 120.78(16) . . ? C5 C6 C7 118.99(16) . . ? C6 C7 C2 120.40(16) . . ? C6 C7 C8 130.51(15) . . ? C2 C7 C8 109.09(14) . . ? C9 C8 C13 120.56(16) . . ? C9 C8 C7 131.10(16) . . ? C13 C8 C7 108.34(14) . . ? C8 C9 C10 118.35(17) . . ? C11 C10 C9 120.90(17) . . ? C10 C11 C12 121.16(17) . . ? C13 C12 C11 117.99(16) . . ? C12 C13 C8 121.02(15) . . ? C12 C13 C1 130.31(15) . . ? C8 C13 C1 108.67(14) . . ? C19 C14 C15 116.97(14) . . ? C19 C14 S1 121.76(12) . . ? C15 C14 S1 121.28(12) . . ? C16 C15 C14 122.44(15) . . ? C16 C15 N2 116.59(14) . . ? C14 C15 N2 120.97(14) . . ? C17 C16 C15 118.18(15) . . ? C16 C17 C18 121.92(15) . . ? C16 C17 N3 118.22(14) . . ? C18 C17 N3 119.85(15) . . ? C19 C18 C17 119.21(15) . . ? C18 C19 C14 121.29(15) . . ? O2 N2 O1 123.09(15) . . ? O2 N2 C15 118.99(14) . . ? O1 N2 C15 117.91(14) . . ? O4 N3 O3 124.24(14) . . ? O4 N3 C17 117.83(14) . . ? O3 N3 C17 117.93(14) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.248 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.069 data_compound_4 _database_code_depnum_ccdc_archive 'CCDC 913183' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H16 N2 S, 0.5(C H2 Cl2)' _chemical_formula_sum 'C26.50 H17 Cl N2 S' _chemical_formula_weight 430.93 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 b c n' _symmetry_space_group_name_Hall '-P 2n 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 26.921(5) _cell_length_b 7.7572(16) _cell_length_c 19.322(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4035.1(14) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 36212 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.419 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1784 _exptl_absorpt_coefficient_mu 0.310 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.902 _exptl_absorpt_correction_T_max 0.971 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 'Nonius Kappa CCD' _diffrn_measurement_method 'thin slice \w and \f scans' _diffrn_reflns_number 33865 _diffrn_reflns_av_R_equivalents 0.0601 _diffrn_reflns_av_sigmaI/netI 0.0341 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 25.03 _reflns_number_total 3557 _reflns_number_gt 2800 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0484P)^2^+3.0822P] 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 3557 _refine_ls_number_parameters 276 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0623 _refine_ls_R_factor_gt 0.0437 _refine_ls_wR_factor_ref 0.1110 _refine_ls_wR_factor_gt 0.1010 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.45531(2) 0.64815(8) 0.53874(3) 0.02971(17) Uani 1 1 d . . . N1 N 0.41249(7) 0.5533(2) 0.58695(10) 0.0283(5) Uani 1 1 d . . . N2 N 0.49604(7) 0.6830(2) 0.60147(10) 0.0299(5) Uani 1 1 d . . . C1 C 0.37085(8) 0.5002(3) 0.55985(11) 0.0256(5) Uani 1 1 d . . . C2 C 0.33398(8) 0.4089(3) 0.60256(11) 0.0249(5) Uani 1 1 d . . . C3 C 0.33479(9) 0.3668(3) 0.67219(11) 0.0293(5) Uani 1 1 d . . . H3A H 0.3620 0.3990 0.7007 0.035 Uiso 1 1 calc R . . C4 C 0.29478(10) 0.2763(3) 0.69938(12) 0.0337(6) Uani 1 1 d . . . H4A H 0.2946 0.2468 0.7471 0.040 Uiso 1 1 calc R . . C5 C 0.25513(9) 0.2285(3) 0.65795(12) 0.0332(6) Uani 1 1 d . . . H5A H 0.2282 0.1665 0.6776 0.040 Uiso 1 1 calc R . . C6 C 0.25427(9) 0.2699(3) 0.58813(12) 0.0287(5) Uani 1 1 d . . . H6A H 0.2270 0.2367 0.5599 0.034 Uiso 1 1 calc R . . C7 C 0.29379(8) 0.3605(3) 0.56021(11) 0.0243(5) Uani 1 1 d . . . C8 C 0.30401(8) 0.4204(3) 0.48949(11) 0.0255(5) Uani 1 1 d . . . C9 C 0.27678(9) 0.4015(3) 0.42909(12) 0.0309(5) Uani 1 1 d . . . H9A H 0.2460 0.3414 0.4291 0.037 Uiso 1 1 calc R . . C10 C 0.29566(9) 0.4729(3) 0.36825(12) 0.0372(6) Uani 1 1 d . . . H10A H 0.2774 0.4618 0.3264 0.045 Uiso 1 1 calc R . . C11 C 0.34064(10) 0.5598(3) 0.36804(13) 0.0372(6) Uani 1 1 d . . . H11A H 0.3525 0.6085 0.3261 0.045 Uiso 1 1 calc R . . C12 C 0.36853(9) 0.5770(3) 0.42783(11) 0.0317(5) Uani 1 1 d . . . H12A H 0.3995 0.6358 0.4272 0.038 Uiso 1 1 calc R . . C13 C 0.35031(8) 0.5066(3) 0.48880(11) 0.0254(5) Uani 1 1 d . . . C14 C 0.53724(8) 0.7648(3) 0.58906(12) 0.0265(5) Uani 1 1 d . . . C15 C 0.55952(8) 0.8418(3) 0.52572(11) 0.0264(5) Uani 1 1 d . . . C16 C 0.54327(9) 0.8485(3) 0.45756(12) 0.0312(5) Uani 1 1 d . . . H16A H 0.5118 0.8026 0.4449 0.037 Uiso 1 1 calc R . . C17 C 0.57388(10) 0.9236(3) 0.40831(12) 0.0343(6) Uani 1 1 d . . . H17A H 0.5632 0.9296 0.3615 0.041 Uiso 1 1 calc R . . C18 C 0.61994(9) 0.9902(3) 0.42639(13) 0.0348(6) Uani 1 1 d . . . H18A H 0.6406 1.0391 0.3917 0.042 Uiso 1 1 calc R . . C19 C 0.63630(9) 0.9864(3) 0.49461(12) 0.0296(5) Uani 1 1 d . . . H19A H 0.6676 1.0333 0.5070 0.036 Uiso 1 1 calc R . . C20 C 0.60576(8) 0.9124(3) 0.54399(11) 0.0256(5) Uani 1 1 d . . . C21 C 0.61391(8) 0.8862(3) 0.61879(11) 0.0254(5) Uani 1 1 d . . . C22 C 0.65278(9) 0.9321(3) 0.66148(12) 0.0327(6) Uani 1 1 d . . . H22A H 0.6803 0.9950 0.6438 0.039 Uiso 1 1 calc R . . C23 C 0.65105(9) 0.8846(3) 0.73111(12) 0.0356(6) Uani 1 1 d . . . H23A H 0.6777 0.9149 0.7610 0.043 Uiso 1 1 calc R . . C24 C 0.61100(9) 0.7939(3) 0.75706(12) 0.0355(6) Uani 1 1 d . . . H24A H 0.6106 0.7614 0.8045 0.043 Uiso 1 1 calc R . . C25 C 0.57148(9) 0.7499(3) 0.71475(12) 0.0318(6) Uani 1 1 d . . . H25A H 0.5437 0.6892 0.7328 0.038 Uiso 1 1 calc R . . C26 C 0.57322(8) 0.7959(3) 0.64554(12) 0.0260(5) Uani 1 1 d . . . C27 C 0.5000 0.3478(5) 0.7500 0.0543(11) Uani 1 2 d S . . H27A H 0.5167 0.4228 0.7843 0.065 Uiso 0.50 1 calc PR . . H27B H 0.4833 0.4228 0.7157 0.065 Uiso 0.50 1 calc PR . . Cl1 Cl 0.54467(3) 0.22027(11) 0.70780(4) 0.0605(2) 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 0.0236(3) 0.0363(3) 0.0291(3) -0.0034(2) 0.0001(2) -0.0028(2) N1 0.0245(11) 0.0294(10) 0.0310(11) -0.0042(8) 0.0016(8) 0.0014(8) N2 0.0248(11) 0.0325(11) 0.0323(11) -0.0046(8) -0.0007(8) -0.0005(9) C1 0.0231(12) 0.0256(11) 0.0282(12) -0.0057(9) -0.0005(10) 0.0013(9) C2 0.0231(12) 0.0225(11) 0.0289(12) -0.0035(9) -0.0021(10) 0.0027(9) C3 0.0283(13) 0.0316(12) 0.0282(12) -0.0033(10) -0.0028(10) 0.0014(10) C4 0.0422(15) 0.0291(12) 0.0298(13) 0.0023(10) 0.0030(11) -0.0011(11) C5 0.0335(14) 0.0274(12) 0.0389(14) 0.0001(10) 0.0047(12) -0.0046(10) C6 0.0243(12) 0.0252(11) 0.0367(13) -0.0030(10) -0.0039(10) -0.0022(9) C7 0.0242(12) 0.0203(10) 0.0283(12) -0.0032(9) -0.0005(10) 0.0016(9) C8 0.0248(12) 0.0228(11) 0.0289(12) -0.0041(9) 0.0004(10) 0.0059(9) C9 0.0269(12) 0.0340(13) 0.0319(13) -0.0070(10) -0.0045(10) 0.0038(10) C10 0.0387(15) 0.0469(15) 0.0260(13) -0.0029(11) -0.0058(11) 0.0087(12) C11 0.0377(15) 0.0459(15) 0.0278(13) 0.0013(11) 0.0026(11) 0.0045(12) C12 0.0307(13) 0.0355(13) 0.0288(13) -0.0019(10) 0.0020(11) 0.0022(11) C13 0.0229(12) 0.0258(11) 0.0275(12) -0.0027(9) 0.0020(10) 0.0046(9) C14 0.0212(12) 0.0260(11) 0.0323(13) -0.0035(10) 0.0010(10) 0.0010(9) C15 0.0245(12) 0.0244(11) 0.0304(13) -0.0025(9) -0.0011(10) 0.0042(9) C16 0.0303(13) 0.0310(12) 0.0322(13) -0.0042(10) -0.0037(11) 0.0037(10) C17 0.0438(16) 0.0351(13) 0.0241(12) 0.0006(10) -0.0029(11) 0.0074(12) C18 0.0383(14) 0.0322(13) 0.0338(14) 0.0046(11) 0.0096(11) 0.0054(11) C19 0.0267(12) 0.0294(12) 0.0327(13) 0.0019(10) 0.0026(10) 0.0008(10) C20 0.0253(12) 0.0221(11) 0.0294(12) -0.0011(9) 0.0016(10) 0.0050(9) C21 0.0244(12) 0.0252(11) 0.0267(12) -0.0010(9) -0.0003(10) 0.0007(9) C22 0.0270(13) 0.0343(13) 0.0367(14) 0.0023(11) -0.0007(11) -0.0049(10) C23 0.0374(15) 0.0368(14) 0.0326(14) -0.0011(11) -0.0103(11) -0.0039(11) C24 0.0446(16) 0.0355(13) 0.0263(12) 0.0013(10) -0.0034(11) -0.0013(12) C25 0.0322(14) 0.0312(13) 0.0322(14) 0.0007(10) 0.0054(11) -0.0059(11) C26 0.0228(12) 0.0249(11) 0.0302(12) -0.0014(9) 0.0009(10) -0.0010(9) C27 0.059(3) 0.035(2) 0.069(3) 0.000 0.017(2) 0.000 Cl1 0.0539(5) 0.0628(5) 0.0648(5) 0.0009(4) 0.0160(4) 0.0101(4) _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 S1 N1 1.655(2) . ? S1 N2 1.657(2) . ? N1 C1 1.304(3) . ? N2 C14 1.300(3) . ? C1 C2 1.472(3) . ? C1 C13 1.481(3) . ? C2 C3 1.385(3) . ? C2 C7 1.408(3) . ? C3 C4 1.389(3) . ? C4 C5 1.385(3) . ? C5 C6 1.387(3) . ? C6 C7 1.384(3) . ? C7 C8 1.469(3) . ? C8 C9 1.386(3) . ? C8 C13 1.415(3) . ? C9 C10 1.395(3) . ? C10 C11 1.386(4) . ? C11 C12 1.384(3) . ? C12 C13 1.388(3) . ? C14 C26 1.479(3) . ? C14 C15 1.488(3) . ? C15 C16 1.389(3) . ? C15 C20 1.405(3) . ? C16 C17 1.387(3) . ? C17 C18 1.388(3) . ? C18 C19 1.390(3) . ? C19 C20 1.384(3) . ? C20 C21 1.476(3) . ? C21 C22 1.379(3) . ? C21 C26 1.399(3) . ? C22 C23 1.396(3) . ? C23 C24 1.381(3) . ? C24 C25 1.385(3) . ? C25 C26 1.385(3) . ? C27 Cl1 1.758(2) 3_656 ? C27 Cl1 1.758(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 N1 S1 N2 96.99(10) . . ? C1 N1 S1 120.88(17) . . ? C14 N2 S1 120.62(17) . . ? N1 C1 C2 120.4(2) . . ? N1 C1 C13 133.1(2) . . ? C2 C1 C13 106.49(18) . . ? C3 C2 C7 120.9(2) . . ? C3 C2 C1 130.3(2) . . ? C7 C2 C1 108.72(19) . . ? C2 C3 C4 118.3(2) . . ? C5 C4 C3 121.0(2) . . ? C4 C5 C6 120.9(2) . . ? C7 C6 C5 118.9(2) . . ? C6 C7 C2 120.0(2) . . ? C6 C7 C8 131.8(2) . . ? C2 C7 C8 108.19(19) . . ? C9 C8 C13 120.5(2) . . ? C9 C8 C7 130.6(2) . . ? C13 C8 C7 108.87(19) . . ? C8 C9 C10 118.3(2) . . ? C11 C10 C9 120.9(2) . . ? C12 C11 C10 121.2(2) . . ? C11 C12 C13 118.6(2) . . ? C12 C13 C8 120.4(2) . . ? C12 C13 C1 131.9(2) . . ? C8 C13 C1 107.73(19) . . ? N2 C14 C26 120.2(2) . . ? N2 C14 C15 133.7(2) . . ? C26 C14 C15 106.11(18) . . ? C16 C15 C20 120.2(2) . . ? C16 C15 C14 131.9(2) . . ? C20 C15 C14 107.87(18) . . ? C17 C16 C15 118.6(2) . . ? C16 C17 C18 121.0(2) . . ? C17 C18 C19 120.9(2) . . ? C20 C19 C18 118.3(2) . . ? C19 C20 C15 121.0(2) . . ? C19 C20 C21 130.1(2) . . ? C15 C20 C21 108.92(19) . . ? C22 C21 C26 120.1(2) . . ? C22 C21 C20 131.5(2) . . ? C26 C21 C20 108.31(19) . . ? C21 C22 C23 118.9(2) . . ? C24 C23 C22 120.7(2) . . ? C23 C24 C25 120.7(2) . . ? C24 C25 C26 118.7(2) . . ? C25 C26 C21 120.8(2) . . ? C25 C26 C14 130.4(2) . . ? C21 C26 C14 108.77(19) . . ? Cl1 C27 Cl1 111.5(2) 3_656 . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.555 _refine_diff_density_min -0.359 _refine_diff_density_rms 0.055