# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Patrick McArdle' _publ_contact_author_email P.MCARDLE@NUIGALWAY.IE _publ_section_title ; Predicting and understanding crystal morphology: The morphology of benzoic acid and the polymorphs of sulfathiazole ; loop_ _publ_author_name 'Patrick McArdle' 'Rex Dark' 'Yun Hu.' 'Aoife Lyons' data_suthaz_f1 _database_code_depnum_ccdc_archive 'CCDC 761678' #TrackingRef 'suthaz_f1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H9 N3 O2 S2' _chemical_formula_weight 255.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, -z-1/2' _cell_length_a 10.5301(5) _cell_length_b 13.1928(9) _cell_length_c 17.040 _cell_angle_alpha 90.00 _cell_angle_beta 107.961(5) _cell_angle_gamma 90.00 _cell_volume 2251.83(19) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _exptl_crystal_description Parallelepiped _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.506 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 0.461 _cell_measurement_theta_max 28.7050 _cell_measurement_theta_min 2.5419 _cell_measurement_reflns_used 2213 _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _exptl_absorpt_correction_T_min 0.95178 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 16.1048 _diffrn_reflns_number 9821 _diffrn_reflns_av_R_equivalents 0.0387 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.5419 _diffrn_reflns_theta_max 25.350 _diffrn_orient_matrix_UB_11 -0.0105466328 _diffrn_orient_matrix_UB_12 0.0331406941 _diffrn_orient_matrix_UB_13 0.0301249656 _diffrn_orient_matrix_UB_21 -0.0105023185 _diffrn_orient_matrix_UB_22 -0.0422004352 _diffrn_orient_matrix_UB_23 0.0228663244 _diffrn_orient_matrix_UB_31 0.0691596094 _diffrn_orient_matrix_UB_32 -0.0013089460 _diffrn_orient_matrix_UB_33 0.0219320850 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 7.00 56.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -20.0250 19.0000 232.0000 0.0000 0.0000 49 #__ type_ start__ end____ width___ exp.time_ 2 omega -5.00 45.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 22.2125 45.0000 0.0000 0.0000 0.0000 50 #__ type_ start__ end____ width___ exp.time_ 3 omega -8.00 44.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 22.2125 -19.0000 307.0000 0.0000 0.0000 52 #__ type_ start__ end____ width___ exp.time_ 4 omega -41.00 -4.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 22.2125 130.0000 267.0000 0.0000 0.0000 37 #__ type_ start__ end____ width___ exp.time_ 5 omega 43.00 92.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 22.2125 45.0000 90.0000 0.0000 0.0000 49 ; _diffrn_ambient_temperature 293(2) _reflns_number_total 3868 _reflns_number_gt 1820 _reflns_threshold_expression >2sigma(I) _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (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^)+(0.0531P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3868 _refine_ls_number_parameters 305 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1036 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.1067 _refine_ls_wR_factor_gt 0.0959 _refine_ls_goodness_of_fit_ref 0.827 _refine_ls_restrained_S_all 0.827 _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 0.78254(9) 0.07378(10) 0.08871(6) 0.0518(3) Uani 1 1 d . . . S2 S 0.82065(11) 0.25400(9) -0.03450(7) 0.0686(4) Uani 1 1 d . . . N1 N 0.9441(4) 0.3383(4) 0.3809(3) 0.0732(12) Uani 1 1 d D . . H1N1 H 1.005(3) 0.317(3) 0.4272(15) 0.088(17) Uiso 1 1 d D . . H2N1 H 0.894(3) 0.386(2) 0.393(2) 0.063(14) Uiso 1 1 d D . . N2 N 0.8986(3) 0.0708(3) 0.04608(16) 0.0434(8) Uani 1 1 d . . . N3 N 0.9925(3) 0.1314(3) -0.05022(17) 0.0530(9) Uani 1 1 d . . . H1N3 H 1.0469 0.0812 -0.0438 0.069 Uiso 1 1 calc R . . O1 O 0.7809(3) -0.0281(2) 0.11931(16) 0.0694(9) Uani 1 1 d . . . O2 O 0.6601(2) 0.1126(3) 0.03418(14) 0.0701(10) Uani 1 1 d . . . C1 C 0.9069(4) 0.2761(3) 0.3137(2) 0.0476(11) Uani 1 1 d . . . C2 C 0.9756(3) 0.1879(3) 0.3102(2) 0.0457(10) Uani 1 1 d . . . H2 H 1.0475 0.1691 0.3553 0.059 Uiso 1 1 calc R . . C3 C 0.9397(3) 0.1279(3) 0.2419(2) 0.0438(10) Uani 1 1 d . . . H3A H 0.9866 0.0684 0.2407 0.057 Uiso 1 1 calc R . . C4 C 0.8324(3) 0.1556(3) 0.17336(19) 0.0398(10) Uani 1 1 d . . . C5 C 0.7622(4) 0.2426(3) 0.1760(2) 0.0560(11) Uani 1 1 d . . . H5 H 0.6910 0.2616 0.1306 0.073 Uiso 1 1 calc R . . C6 C 0.7976(4) 0.3016(3) 0.2459(2) 0.0594(12) Uani 1 1 d . . . H6A H 0.7481 0.3593 0.2481 0.077 Uiso 1 1 calc R . . C7 C 0.9067(3) 0.1408(3) -0.0071(2) 0.0435(10) Uani 1 1 d . . . C8 C 0.8980(5) 0.2799(4) -0.1062(3) 0.0786(15) Uani 1 1 d . . . H8 H 0.8806 0.3362 -0.1408 0.102 Uiso 1 1 calc R . . C9 C 0.9869(5) 0.2085(4) -0.1061(3) 0.0703(13) Uani 1 1 d . . . H9 H 1.0404 0.2102 -0.1404 0.091 Uiso 1 1 calc R . . S3 S 0.69998(10) -0.42840(9) -0.12144(6) 0.0521(3) Uani 1 1 d . . . S4 S 0.70128(11) -0.43066(12) 0.07010(7) 0.0837(5) Uani 1 1 d . . . N4 N 0.6884(4) 0.0156(3) -0.1481(2) 0.0601(10) Uani 1 1 d D . . H1N4 H 0.633(2) 0.055(2) -0.1316(18) 0.039(11) Uiso 1 1 d D . . H2N4 H 0.729(3) 0.045(3) -0.1807(19) 0.068(14) Uiso 1 1 d D . . N5 N 0.8278(3) -0.4653(2) -0.04805(18) 0.0492(9) Uani 1 1 d . . . N6 N 0.9332(3) -0.4921(3) 0.09053(18) 0.0520(9) Uani 1 1 d . . . H1N6 H 1.0041 -0.5139 0.0811 0.068 Uiso 1 1 calc R . . O3 O 0.7263(3) -0.4654(2) -0.19442(15) 0.0727(9) Uani 1 1 d . . . O4 O 0.5785(2) -0.4589(2) -0.10737(16) 0.0669(9) Uani 1 1 d . . . C10 C 0.6943(4) -0.0859(3) -0.1386(2) 0.0429(10) Uani 1 1 d . . . C11 C 0.6175(4) -0.1359(4) -0.0980(2) 0.0542(11) Uani 1 1 d . . . H11 H 0.5636 -0.0987 -0.0745 0.071 Uiso 1 1 calc R . . C12 C 0.6199(4) -0.2390(4) -0.0919(2) 0.0514(11) Uani 1 1 d . . . H12 H 0.5659 -0.2712 -0.0654 0.067 Uiso 1 1 calc R . . C13 C 0.7019(3) -0.2968(3) -0.12463(19) 0.0427(10) Uani 1 1 d . . . C14 C 0.7820(4) -0.2465(4) -0.1634(2) 0.0540(11) Uani 1 1 d . . . H14 H 0.8387 -0.2832 -0.1851 0.070 Uiso 1 1 calc R . . C15 C 0.7776(4) -0.1434(4) -0.1698(2) 0.0551(11) Uani 1 1 d . . . H15 H 0.8320 -0.1109 -0.1958 0.072 Uiso 1 1 calc R . . C16 C 0.8257(4) -0.4644(3) 0.0295(2) 0.0467(10) Uani 1 1 d . . . C17 C 0.8073(5) -0.4496(4) 0.1687(3) 0.0930(18) Uani 1 1 d . . . H17 H 0.7838 -0.4370 0.2161 0.121 Uiso 1 1 calc R . . C18 C 0.9257(4) -0.4842(4) 0.1695(3) 0.0700(13) Uani 1 1 d . . . H18 H 0.9945 -0.5008 0.2170 0.091 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 0.0463(6) 0.0698(9) 0.0417(5) -0.0093(6) 0.0173(4) -0.0077(7) S2 0.0720(7) 0.0490(8) 0.0868(8) 0.0044(7) 0.0271(6) 0.0083(7) N1 0.072(3) 0.078(3) 0.065(3) -0.031(3) 0.013(2) 0.011(3) N2 0.0489(17) 0.050(2) 0.0367(16) -0.0002(17) 0.0206(13) 0.0031(19) N3 0.0568(19) 0.056(2) 0.054(2) 0.0063(19) 0.0273(16) 0.001(2) O1 0.093(2) 0.056(2) 0.0709(19) -0.0074(17) 0.0422(16) -0.0265(19) O2 0.0363(13) 0.120(3) 0.0485(15) -0.0157(17) 0.0053(12) 0.0019(17) C1 0.042(2) 0.057(3) 0.045(2) -0.005(2) 0.0153(19) -0.004(2) C2 0.037(2) 0.057(3) 0.039(2) -0.005(2) 0.0071(16) 0.004(2) C3 0.0332(19) 0.052(3) 0.050(2) 0.005(2) 0.0181(17) 0.003(2) C4 0.041(2) 0.046(3) 0.037(2) -0.0023(19) 0.0184(17) 0.002(2) C5 0.054(2) 0.065(3) 0.045(2) 0.001(2) 0.0081(18) 0.012(3) C6 0.063(2) 0.054(3) 0.062(3) -0.003(2) 0.020(2) 0.024(3) C7 0.040(2) 0.048(3) 0.043(2) -0.011(2) 0.0133(17) -0.005(2) C8 0.100(4) 0.048(3) 0.087(4) 0.018(3) 0.027(3) 0.001(3) C9 0.092(3) 0.065(4) 0.063(3) 0.009(3) 0.036(3) -0.021(3) S3 0.0562(6) 0.0545(8) 0.0490(6) -0.0097(6) 0.0210(5) -0.0029(7) S4 0.0767(8) 0.1225(13) 0.0693(7) 0.0234(8) 0.0479(6) 0.0410(9) N4 0.080(3) 0.053(3) 0.052(2) -0.005(2) 0.028(2) 0.003(3) N5 0.0507(18) 0.053(2) 0.0519(19) -0.0007(17) 0.0281(15) 0.0084(19) N6 0.057(2) 0.054(3) 0.055(2) 0.0050(18) 0.0323(17) 0.011(2) O3 0.096(2) 0.072(2) 0.0554(17) -0.0191(16) 0.0311(16) -0.0009(19) O4 0.0510(15) 0.072(2) 0.0802(19) -0.0102(17) 0.0246(14) -0.0196(17) C10 0.045(2) 0.048(3) 0.032(2) -0.002(2) 0.0054(16) 0.007(2) C11 0.058(2) 0.059(3) 0.057(3) 0.001(2) 0.034(2) 0.012(3) C12 0.050(2) 0.061(3) 0.055(2) 0.004(2) 0.0318(19) 0.003(3) C13 0.042(2) 0.052(3) 0.0360(19) -0.004(2) 0.0139(16) 0.004(2) C14 0.053(2) 0.066(3) 0.055(2) -0.001(2) 0.033(2) 0.008(3) C15 0.053(2) 0.062(4) 0.059(3) 0.004(2) 0.030(2) -0.003(3) C16 0.054(2) 0.039(3) 0.055(2) 0.000(2) 0.029(2) -0.001(2) C17 0.111(4) 0.124(5) 0.064(3) 0.021(3) 0.056(3) 0.041(4) C18 0.078(3) 0.085(4) 0.057(3) 0.008(3) 0.035(2) 0.020(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O2 1.432(2) . ? S1 O1 1.444(3) . ? S1 N2 1.603(3) . ? S1 C4 1.748(4) . ? S2 C8 1.700(5) . ? S2 C7 1.735(4) . ? N1 C1 1.365(5) . ? N1 H1N1 0.897(10) . ? N1 H2N1 0.884(10) . ? N2 C7 1.314(4) . ? N3 C7 1.334(4) . ? N3 C9 1.382(5) . ? N3 H1N3 0.8600 . ? C1 C2 1.381(5) . ? C1 C6 1.398(5) . ? C2 C3 1.362(5) . ? C2 H2 0.9300 . ? C3 C4 1.400(4) . ? C3 H3A 0.9300 . ? C4 C5 1.374(5) . ? C5 C6 1.375(5) . ? C5 H5 0.9300 . ? C6 H6A 0.9300 . ? C8 C9 1.327(5) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? S3 O4 1.430(2) . ? S3 O3 1.440(2) . ? S3 N5 1.605(3) . ? S3 C13 1.737(4) . ? S4 C16 1.718(4) . ? S4 C17 1.725(5) . ? N4 C10 1.349(5) . ? N4 H1N4 0.884(10) . ? N4 H2N4 0.889(10) . ? N5 C16 1.328(4) . ? N6 C16 1.331(4) . ? N6 C18 1.376(4) . ? N6 H1N6 0.8600 . ? C10 C11 1.383(5) . ? C10 C15 1.384(5) . ? C11 C12 1.364(5) . ? C11 H11 0.9300 . ? C12 C13 1.391(5) . ? C12 H12 0.9300 . ? C13 C14 1.390(5) . ? C14 C15 1.364(5) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C17 C18 1.324(5) . ? C17 H17 0.9300 . ? C18 H18 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 O2 S1 O1 117.30(19) . . ? O2 S1 N2 112.00(15) . . ? O1 S1 N2 103.69(17) . . ? O2 S1 C4 107.21(18) . . ? O1 S1 C4 108.12(17) . . ? N2 S1 C4 108.19(15) . . ? C8 S2 C7 92.3(2) . . ? C1 N1 H1N1 119(3) . . ? C1 N1 H2N1 126(3) . . ? H1N1 N1 H2N1 110(4) . . ? C7 N2 S1 121.1(3) . . ? C7 N3 C9 114.7(4) . . ? C7 N3 H1N3 122.6 . . ? C9 N3 H1N3 122.6 . . ? N1 C1 C2 121.7(4) . . ? N1 C1 C6 119.9(4) . . ? C2 C1 C6 118.4(4) . . ? C3 C2 C1 121.1(3) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C2 C3 C4 120.1(4) . . ? C2 C3 H3A 120.0 . . ? C4 C3 H3A 120.0 . . ? C5 C4 C3 119.7(4) . . ? C5 C4 S1 121.0(3) . . ? C3 C4 S1 119.1(3) . . ? C4 C5 C6 119.8(4) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C5 C6 C1 120.9(4) . . ? C5 C6 H6A 119.5 . . ? C1 C6 H6A 119.5 . . ? N2 C7 N3 120.9(4) . . ? N2 C7 S2 130.6(3) . . ? N3 C7 S2 108.5(3) . . ? C9 C8 S2 110.5(4) . . ? C9 C8 H8 124.8 . . ? S2 C8 H8 124.8 . . ? C8 C9 N3 113.9(4) . . ? C8 C9 H9 123.1 . . ? N3 C9 H9 123.1 . . ? O4 S3 O3 118.01(17) . . ? O4 S3 N5 111.28(16) . . ? O3 S3 N5 103.40(16) . . ? O4 S3 C13 107.84(18) . . ? O3 S3 C13 107.71(18) . . ? N5 S3 C13 108.19(17) . . ? C16 S4 C17 90.6(2) . . ? C10 N4 H1N4 124(2) . . ? C10 N4 H2N4 120(3) . . ? H1N4 N4 H2N4 115(4) . . ? C16 N5 S3 120.3(3) . . ? C16 N6 C18 116.9(3) . . ? C16 N6 H1N6 121.6 . . ? C18 N6 H1N6 121.6 . . ? N4 C10 C11 121.4(4) . . ? N4 C10 C15 120.7(4) . . ? C11 C10 C15 117.9(4) . . ? C12 C11 C10 120.9(4) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C11 C12 C13 121.0(4) . . ? C11 C12 H12 119.5 . . ? C13 C12 H12 119.5 . . ? C14 C13 C12 118.1(4) . . ? C14 C13 S3 120.4(3) . . ? C12 C13 S3 121.4(3) . . ? C15 C14 C13 120.2(4) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C10 121.8(4) . . ? C14 C15 H15 119.1 . . ? C10 C15 H15 119.1 . . ? N5 C16 N6 120.2(3) . . ? N5 C16 S4 130.7(3) . . ? N6 C16 S4 109.1(3) . . ? C18 C17 S4 112.6(3) . . ? C18 C17 H17 123.7 . . ? S4 C17 H17 123.7 . . ? C17 C18 N6 110.7(4) . . ? C17 C18 H18 124.6 . . ? N6 C18 H18 124.6 . . ? _diffrn_measured_fraction_theta_max 0.939 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.939 _refine_diff_density_max 0.312 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.049 data_suthaz_f2 _database_code_depnum_ccdc_archive 'CCDC 761679' #TrackingRef 'suthaz_f2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H9 N3 O2 S2' _chemical_formula_weight 255.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y+1/2, z+1/2' '-x, -y, -z' '-x, y-1/2, -z-1/2' _cell_length_a 8.2241(4) _cell_length_b 8.5725(4) _cell_length_c 15.5081(7) _cell_angle_alpha 90.00 _cell_angle_beta 93.794(4) _cell_angle_gamma 90.00 _cell_volume 1090.94(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4187 _cell_measurement_theta_min 2.7065 _cell_measurement_theta_max 28.6460 _exptl_crystal_description Parallelepiped _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.554 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.476 _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) ; _exptl_absorpt_correction_T_min 0.98389 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.9 (release 08-12-2009 CrysAlis171 .NET) (compiled Dec 8 2009,17:31:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_detector_area_resol_mean 16.1048 _diffrn_reflns_number 6730 _diffrn_reflns_av_R_equivalents 0.0159 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.7065 _diffrn_reflns_theta_max 25.350 _diffrn_orient_matrix_UB_11 -0.0853729000 _diffrn_orient_matrix_UB_12 0.0069735000 _diffrn_orient_matrix_UB_13 -0.0085684000 _diffrn_orient_matrix_UB_21 0.0006730000 _diffrn_orient_matrix_UB_22 -0.0661539000 _diffrn_orient_matrix_UB_23 -0.0272954000 _diffrn_orient_matrix_UB_31 -0.0129504000 _diffrn_orient_matrix_UB_32 -0.0489992000 _diffrn_orient_matrix_UB_33 0.0356478000 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -93.00 -41.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - -20.0250 -45.0000 0.0000 52 #__ type_ start__ end____ width___ exp.time_ 2 omega -47.00 5.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - -20.0250 45.0000 270.0000 52 #__ type_ start__ end____ width___ exp.time_ 3 omega -3.00 48.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 22.2125 -51.0000 34.0000 51 #__ type_ start__ end____ width___ exp.time_ 4 omega -3.00 45.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 22.2125 51.0000 0.0000 48 #__ type_ start__ end____ width___ exp.time_ 5 omega -50.00 2.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 22.2125 -45.0000 240.0000 52 #__ type_ start__ end____ width___ exp.time_ 6 omega -40.00 2.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 22.2125 -45.0000 270.0000 42 #__ type_ start__ end____ width___ exp.time_ 7 omega 3.00 42.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 22.2125 -45.0000 90.0000 39 ; _diffrn_measurement_method '\w scans' _diffrn_ambient_temperature 293(2) _reflns_number_total 2225 _reflns_number_gt 1969 _reflns_threshold_expression >2sigma(I) _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (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^)+(0.0532P)^2^+0.9258P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2225 _refine_ls_number_parameters 153 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0377 _refine_ls_R_factor_gt 0.0325 _refine_ls_wR_factor_ref 0.0920 _refine_ls_wR_factor_gt 0.0874 _refine_ls_goodness_of_fit_ref 0.887 _refine_ls_restrained_S_all 0.886 _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 0.23097(5) 0.89107(5) 0.11773(3) 0.02922(14) Uani 1 1 d . . . S2 S 0.28633(9) 0.66655(7) -0.04782(4) 0.0558(2) Uani 1 1 d . . . N1 N 0.8932(2) 0.8159(2) 0.28896(11) 0.0350(4) Uani 1 1 d D . . H1N1 H 0.912(3) 0.7184(14) 0.3071(13) 0.042(6) Uiso 1 1 d D . . H2N1 H 0.972(2) 0.849(3) 0.2566(14) 0.055(7) Uiso 1 1 d D . . N2 N 0.15918(19) 0.71892(19) 0.11135(10) 0.0330(4) Uani 1 1 d . . . N3 N 0.1741(2) 0.47198(19) 0.05376(10) 0.0346(4) Uani 1 1 d . . . H1N3 H 0.1306 0.4300 0.0970 0.045 Uiso 1 1 calc R . . O1 O 0.13517(16) 0.97132(16) 0.17849(9) 0.0391(3) Uani 1 1 d . . . O2 O 0.24442(17) 0.96549(17) 0.03546(9) 0.0416(4) Uani 1 1 d . . . C1 C 0.7388(2) 0.8335(2) 0.24581(11) 0.0284(4) Uani 1 1 d . . . C2 C 0.6030(2) 0.7708(2) 0.28307(12) 0.0334(4) Uani 1 1 d . . . H2 H 0.6165 0.7174 0.3352 0.043 Uiso 1 1 calc R . . C3 C 0.4499(2) 0.7875(2) 0.24326(12) 0.0323(4) Uani 1 1 d . . . H3A H 0.3603 0.7442 0.2680 0.042 Uiso 1 1 calc R . . C4 C 0.4290(2) 0.8692(2) 0.16608(11) 0.0267(4) Uani 1 1 d . . . C5 C 0.5625(2) 0.9333(2) 0.12909(11) 0.0292(4) Uani 1 1 d . . . H5 H 0.5483 0.9882 0.0774 0.038 Uiso 1 1 calc R . . C6 C 0.7165(2) 0.9157(2) 0.16889(11) 0.0303(4) Uani 1 1 d . . . H6 H 0.8059 0.9591 0.1440 0.039 Uiso 1 1 calc R . . C7 C 0.2007(2) 0.6247(2) 0.04929(11) 0.0312(4) Uani 1 1 d . . . C8 C 0.2833(4) 0.4711(3) -0.07500(17) 0.0633(7) Uani 1 1 d . . . H8 H 0.3214 0.4313 -0.1257 0.082 Uiso 1 1 calc R . . C9 C 0.2203(3) 0.3855(3) -0.01511(14) 0.0479(5) Uani 1 1 d . . . H9 H 0.2084 0.2778 -0.0190 0.062 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 0.0265(2) 0.0284(2) 0.0336(2) 0.00030(17) 0.00812(17) -0.00357(17) S2 0.0823(5) 0.0493(4) 0.0386(3) -0.0061(2) 0.0255(3) -0.0135(3) N1 0.0297(8) 0.0337(9) 0.0419(9) 0.0060(7) 0.0056(7) 0.0003(7) N2 0.0344(8) 0.0326(8) 0.0329(8) -0.0035(6) 0.0084(6) -0.0092(7) N3 0.0372(9) 0.0327(8) 0.0336(8) -0.0022(7) 0.0006(7) -0.0045(7) O1 0.0322(7) 0.0329(7) 0.0539(8) -0.0082(6) 0.0158(6) -0.0020(6) O2 0.0387(8) 0.0454(8) 0.0408(8) 0.0133(6) 0.0035(6) -0.0052(6) C1 0.0291(9) 0.0237(8) 0.0331(9) -0.0033(7) 0.0074(7) -0.0010(7) C2 0.0367(10) 0.0328(10) 0.0313(9) 0.0071(8) 0.0078(7) -0.0029(8) C3 0.0299(9) 0.0342(10) 0.0343(9) 0.0045(8) 0.0131(7) -0.0053(8) C4 0.0278(9) 0.0243(8) 0.0288(8) -0.0030(7) 0.0083(7) -0.0031(7) C5 0.0333(9) 0.0291(9) 0.0263(8) 0.0017(7) 0.0096(7) -0.0040(7) C6 0.0286(9) 0.0310(9) 0.0325(9) -0.0003(7) 0.0118(7) -0.0051(7) C7 0.0297(9) 0.0349(10) 0.0289(9) -0.0004(7) 0.0003(7) -0.0046(7) C8 0.0861(19) 0.0560(15) 0.0504(14) -0.0220(12) 0.0246(13) -0.0084(14) C9 0.0545(13) 0.0412(12) 0.0481(12) -0.0153(10) 0.0032(10) -0.0009(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 O2 1.4374(14) . ? S1 O1 1.4423(13) . ? S1 N2 1.5901(16) . ? S1 C4 1.7572(18) . ? S2 C8 1.727(3) . ? S2 C7 1.7415(19) . ? N1 C1 1.403(2) . ? N1 H1N1 0.892(10) . ? N1 H2N1 0.890(10) . ? N2 C7 1.318(2) . ? N3 C7 1.330(2) . ? N3 C9 1.374(3) . ? N3 H1N3 0.8600 . ? C1 C6 1.387(3) . ? C1 C2 1.399(2) . ? C2 C3 1.372(3) . ? C2 H2 0.9300 . ? C3 C4 1.387(2) . ? C3 H3A 0.9300 . ? C4 C5 1.386(2) . ? C5 C6 1.380(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C8 C9 1.317(3) . ? C8 H8 0.9300 . ? C9 H9 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 O2 S1 O1 116.47(9) . . ? O2 S1 N2 114.00(9) . . ? O1 S1 N2 105.47(8) . . ? O2 S1 C4 107.61(8) . . ? O1 S1 C4 107.65(8) . . ? N2 S1 C4 104.90(8) . . ? C8 S2 C7 90.64(11) . . ? C1 N1 H1N1 112.5(15) . . ? C1 N1 H2N1 111.2(17) . . ? H1N1 N1 H2N1 111(2) . . ? C7 N2 S1 120.05(13) . . ? C7 N3 C9 115.83(18) . . ? C7 N3 H1N3 122.1 . . ? C9 N3 H1N3 122.1 . . ? C6 C1 C2 119.11(17) . . ? C6 C1 N1 121.90(16) . . ? C2 C1 N1 118.95(16) . . ? C3 C2 C1 120.54(17) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C2 C3 C4 119.90(16) . . ? C2 C3 H3A 120.0 . . ? C4 C3 H3A 120.0 . . ? C5 C4 C3 120.06(17) . . ? C5 C4 S1 121.22(14) . . ? C3 C4 S1 118.72(13) . . ? C6 C5 C4 120.03(16) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C1 120.35(16) . . ? C5 C6 H6 119.8 . . ? C1 C6 H6 119.8 . . ? N2 C7 N3 120.88(17) . . ? N2 C7 S2 130.12(15) . . ? N3 C7 S2 108.97(14) . . ? C9 C8 S2 111.64(18) . . ? C9 C8 H8 124.2 . . ? S2 C8 H8 124.2 . . ? C8 C9 N3 112.9(2) . . ? C8 C9 H9 123.5 . . ? N3 C9 H9 123.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.395 _refine_diff_density_min -0.293 _refine_diff_density_rms 0.043 data_suthaz_f3 _database_code_depnum_ccdc_archive 'CCDC 761680' #TrackingRef 'suthaz_f3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H9 N3 O2 S2' _chemical_formula_weight 255.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y+1/2, z+1/2' '-x, -y, -z' '-x, y-1/2, -z-1/2' _cell_length_a 17.5911(11) _cell_length_b 8.5439(4) _cell_length_c 15.5940(10) _cell_angle_alpha 90.00 _cell_angle_beta 113.022(8) _cell_angle_gamma 90.00 _cell_volume 2157.1(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _exptl_crystal_description Parallelepiped _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.572 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 0.481 _cell_measurement_theta_max 26.6864 _cell_measurement_theta_min 2.6867 _cell_measurement_reflns_used 8003 _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _exptl_absorpt_correction_T_min 0.35996 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Goniometer KM4/Xcalibur, detector: Sapphire3' _diffrn_detector_area_resol_mean 16.1048 _diffrn_reflns_number 21997 _diffrn_reflns_av_R_equivalents 0.0343 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.6867 _diffrn_reflns_theta_max 25.350 _diffrn_orient_matrix_UB_11 0.0061245042 _diffrn_orient_matrix_UB_12 0.0144355633 _diffrn_orient_matrix_UB_13 -0.0374077750 _diffrn_orient_matrix_UB_21 -0.0156636703 _diffrn_orient_matrix_UB_22 -0.0769402328 _diffrn_orient_matrix_UB_23 -0.0136394772 _diffrn_orient_matrix_UB_31 -0.0464674576 _diffrn_orient_matrix_UB_32 0.0277623661 _diffrn_orient_matrix_UB_33 -0.0184541939 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -12.00 85.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 13.5170 37.0000 180.0000 97 #__ type_ start__ end____ width___ exp.time_ 2 omega -47.00 44.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 13.5174 -77.0000 0.0000 91 #__ type_ start__ end____ width___ exp.time_ 3 omega -88.00 -32.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -11.1736 179.0000 60.0000 56 #__ type_ start__ end____ width___ exp.time_ 4 omega -17.00 84.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 13.5174 77.0000 330.0000 101 #__ type_ start__ end____ width___ exp.time_ 5 omega -59.00 39.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 13.5174 -37.0000 210.0000 98 #__ type_ start__ end____ width___ exp.time_ 6 omega -12.00 19.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 13.5174 37.0000 300.0000 31 #__ type_ start__ end____ width___ exp.time_ 7 omega -27.00 54.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 13.5174 -97.0000 26.0000 81 ; _diffrn_measurement_method '\w scans' _diffrn_ambient_temperature 293(2) _reflns_number_total 3845 _reflns_number_gt 2492 _reflns_threshold_expression >2sigma(I) _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (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^)+(0.0447P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3845 _refine_ls_number_parameters 305 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0597 _refine_ls_R_factor_gt 0.0324 _refine_ls_wR_factor_ref 0.0748 _refine_ls_wR_factor_gt 0.0708 _refine_ls_goodness_of_fit_ref 0.856 _refine_ls_restrained_S_all 0.856 _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 0.38311(3) -0.39860(6) 0.05831(3) 0.02993(15) Uani 1 1 d . . . S2 S 0.35605(5) -0.17463(8) -0.12203(4) 0.0555(2) Uani 1 1 d . . . N1 N 0.04445(12) -0.3047(2) 0.04904(13) 0.0335(5) Uani 1 1 d D . . H1N1 H 0.0395(13) -0.2054(13) 0.0645(13) 0.040(7) Uiso 1 1 d D . . H2N1 H 0.0054(11) -0.327(2) -0.0059(9) 0.047(7) Uiso 1 1 d D . . N2 N 0.41984(11) -0.22618(19) 0.06949(11) 0.0326(5) Uani 1 1 d . . . N3 N 0.41154(11) 0.02170(19) 0.00775(12) 0.0345(5) Uani 1 1 d . . . H1N3 H 0.4331 0.0642 0.0619 0.045 Uiso 1 1 calc R . . O1 O 0.37670(9) -0.47554(17) -0.02629(9) 0.0399(4) Uani 1 1 d . . . O2 O 0.43105(8) -0.47815(16) 0.14420(9) 0.0390(4) Uani 1 1 d . . . C1 C 0.12383(12) -0.3293(2) 0.04929(13) 0.0260(5) Uani 1 1 d . . . C2 C 0.13613(12) -0.4176(2) -0.01831(13) 0.0279(5) Uani 1 1 d . . . H2 H 0.0910 -0.4629 -0.0656 0.036 Uiso 1 1 calc R . . C3 C 0.21458(12) -0.4397(2) -0.01679(13) 0.0283(5) Uani 1 1 d . . . H3A H 0.2220 -0.4982 -0.0632 0.037 Uiso 1 1 calc R . . C4 C 0.28223(12) -0.3741(2) 0.05433(13) 0.0256(5) Uani 1 1 d . . . C5 C 0.27063(14) -0.2881(2) 0.12343(13) 0.0315(5) Uani 1 1 d . . . H5 H 0.3159 -0.2443 0.1713 0.041 Uiso 1 1 calc R . . C6 C 0.19269(14) -0.2670(2) 0.12172(14) 0.0331(6) Uani 1 1 d . . . H6A H 0.1856 -0.2108 0.1692 0.043 Uiso 1 1 calc R . . C7 C 0.39867(13) -0.1326(2) -0.00333(14) 0.0316(5) Uani 1 1 d . . . C8 C 0.35709(18) 0.0208(3) -0.14873(18) 0.0616(8) Uani 1 1 d . . . H8 H 0.3381 0.0601 -0.2091 0.080 Uiso 1 1 calc R . . C9 C 0.38821(15) 0.1082(3) -0.07298(17) 0.0464(6) Uani 1 1 d . . . H9 H 0.3937 0.2164 -0.0741 0.060 Uiso 1 1 calc R . . S3 S 0.10839(3) 0.12004(6) 0.18189(3) 0.02990(16) Uani 1 1 d . . . S4 S 0.13668(5) 0.34892(7) 0.35946(4) 0.0564(2) Uani 1 1 d . . . N4 N 0.44587(12) 0.1764(2) 0.18248(13) 0.0359(5) Uani 1 1 d D . . H1N4 H 0.4862(11) 0.138(2) 0.2331(10) 0.051(7) Uiso 1 1 d D . . H2N4 H 0.4563(13) 0.2730(14) 0.1693(14) 0.041(7) Uiso 1 1 d D . . N5 N 0.07395(10) 0.29546(18) 0.16830(11) 0.0295(4) Uani 1 1 d . . . N6 N 0.08025(10) 0.54420(18) 0.22939(12) 0.0321(4) Uani 1 1 d . . . H1N6 H 0.0582 0.5862 0.1751 0.042 Uiso 1 1 calc R . . O3 O 0.06002(9) 0.03955(15) 0.09754(10) 0.0422(4) Uani 1 1 d . . . O4 O 0.11369(9) 0.05091(16) 0.26828(9) 0.0403(4) Uani 1 1 d . . . C10 C 0.36733(13) 0.1625(2) 0.18587(14) 0.0284(5) Uani 1 1 d . . . C11 C 0.29895(14) 0.2230(2) 0.11215(14) 0.0339(6) Uani 1 1 d . . . H11 H 0.3060 0.2717 0.0624 0.044 Uiso 1 1 calc R . . C12 C 0.22154(14) 0.2110(2) 0.11291(14) 0.0336(5) Uani 1 1 d . . . H12 H 0.1766 0.2531 0.0640 0.044 Uiso 1 1 calc R . . C13 C 0.20934(12) 0.1369(2) 0.18565(13) 0.0266(5) Uani 1 1 d . . . C14 C 0.27698(13) 0.0744(2) 0.25833(13) 0.0302(5) Uani 1 1 d . . . H14 H 0.2696 0.0238 0.3073 0.039 Uiso 1 1 calc R . . C15 C 0.35507(13) 0.0872(2) 0.25808(13) 0.0307(5) Uani 1 1 d . . . H15 H 0.4000 0.0447 0.3069 0.040 Uiso 1 1 calc R . . C16 C 0.09398(12) 0.3905(2) 0.24115(13) 0.0284(5) Uani 1 1 d . . . C17 C 0.13574(18) 0.5458(3) 0.38577(17) 0.0616(8) Uani 1 1 d . . . H17 H 0.1554 0.5860 0.4460 0.080 Uiso 1 1 calc R . . C18 C 0.10378(15) 0.6311(3) 0.30996(16) 0.0451(6) Uani 1 1 d . . . H18 H 0.0977 0.7391 0.3107 0.059 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 0.0277(3) 0.0279(3) 0.0286(3) -0.0017(2) 0.0049(3) -0.0034(2) S2 0.0819(5) 0.0470(4) 0.0308(4) -0.0006(3) 0.0146(3) -0.0109(3) N1 0.0303(12) 0.0296(11) 0.0355(12) -0.0001(9) 0.0074(10) 0.0036(9) N2 0.0347(11) 0.0297(10) 0.0285(10) 0.0006(8) 0.0069(8) -0.0085(8) N3 0.0377(11) 0.0303(11) 0.0364(11) -0.0014(9) 0.0155(9) -0.0044(8) O1 0.0365(9) 0.0438(9) 0.0375(9) -0.0144(7) 0.0124(7) -0.0041(7) O2 0.0326(9) 0.0321(8) 0.0383(9) 0.0087(7) -0.0011(7) -0.0016(7) C1 0.0277(13) 0.0186(10) 0.0274(12) 0.0063(9) 0.0061(10) 0.0007(9) C2 0.0257(12) 0.0267(11) 0.0234(11) -0.0002(9) 0.0012(10) -0.0041(9) C3 0.0338(13) 0.0246(11) 0.0221(11) -0.0010(9) 0.0063(10) -0.0037(9) C4 0.0273(12) 0.0212(11) 0.0231(11) 0.0023(9) 0.0041(9) -0.0028(9) C5 0.0312(14) 0.0308(12) 0.0233(12) -0.0052(9) 0.0008(10) -0.0036(10) C6 0.0386(15) 0.0305(12) 0.0268(12) -0.0046(9) 0.0092(11) -0.0021(10) C7 0.0268(12) 0.0347(13) 0.0337(13) -0.0046(11) 0.0124(10) -0.0055(10) C8 0.081(2) 0.0546(17) 0.0417(16) 0.0135(14) 0.0164(15) -0.0047(15) C9 0.0517(16) 0.0380(14) 0.0509(16) 0.0148(13) 0.0216(13) 0.0012(12) S3 0.0295(3) 0.0242(3) 0.0295(3) -0.0003(2) 0.0044(3) 0.0019(2) S4 0.0896(6) 0.0442(4) 0.0269(4) -0.0008(3) 0.0135(3) 0.0099(4) N4 0.0324(12) 0.0310(12) 0.0387(12) 0.0067(10) 0.0077(10) 0.0011(9) N5 0.0328(11) 0.0253(10) 0.0246(9) -0.0011(8) 0.0048(8) 0.0049(8) N6 0.0358(11) 0.0267(10) 0.0331(10) -0.0025(8) 0.0127(8) 0.0044(8) O3 0.0360(9) 0.0317(8) 0.0435(9) -0.0127(7) -0.0011(7) 0.0011(7) O4 0.0410(10) 0.0371(9) 0.0413(9) 0.0130(7) 0.0146(8) 0.0044(7) C10 0.0312(13) 0.0203(10) 0.0300(12) -0.0022(9) 0.0081(10) 0.0017(9) C11 0.0384(15) 0.0326(12) 0.0283(12) 0.0078(10) 0.0104(11) 0.0034(10) C12 0.0323(14) 0.0351(13) 0.0251(12) 0.0062(10) 0.0023(10) 0.0068(10) C13 0.0304(12) 0.0214(11) 0.0219(11) -0.0022(9) 0.0037(10) 0.0025(9) C14 0.0371(14) 0.0270(11) 0.0229(11) 0.0017(9) 0.0079(10) 0.0035(10) C15 0.0296(13) 0.0311(12) 0.0227(11) 0.0028(9) 0.0007(10) 0.0044(10) C16 0.0255(12) 0.0300(12) 0.0299(12) 0.0013(10) 0.0109(10) 0.0026(9) C17 0.091(2) 0.0503(16) 0.0345(14) -0.0164(13) 0.0149(15) 0.0057(15) C18 0.0538(16) 0.0336(13) 0.0490(16) -0.0150(12) 0.0214(13) 0.0016(12) _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 O1 1.4385(14) . ? S1 O2 1.4434(14) . ? S1 N2 1.5906(17) . ? S1 C4 1.764(2) . ? S2 C8 1.723(3) . ? S2 C7 1.741(2) . ? N1 C1 1.411(3) . ? N1 H1N1 0.896(9) . ? N1 H2N1 0.884(9) . ? N2 C7 1.318(2) . ? N3 C7 1.338(3) . ? N3 C9 1.377(3) . ? N3 H1N3 0.8600 . ? C1 C2 1.381(3) . ? C1 C6 1.398(3) . ? C2 C3 1.384(3) . ? C2 H2 0.9300 . ? C3 C4 1.389(3) . ? C3 H3A 0.9300 . ? C4 C5 1.384(3) . ? C5 C6 1.373(3) . ? C5 H5 0.9300 . ? C6 H6A 0.9300 . ? C8 C9 1.322(3) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? S3 O3 1.4324(14) . ? S3 O4 1.4402(14) . ? S3 N5 1.5993(16) . ? S3 C13 1.759(2) . ? S4 C17 1.733(2) . ? S4 C16 1.735(2) . ? N4 C10 1.408(3) . ? N4 H1N4 0.891(9) . ? N4 H2N4 0.886(9) . ? N5 C16 1.327(2) . ? N6 C16 1.335(2) . ? N6 C18 1.376(2) . ? N6 H1N6 0.8600 . ? C10 C15 1.385(3) . ? C10 C11 1.398(3) . ? C11 C12 1.370(3) . ? C11 H11 0.9300 . ? C12 C13 1.387(3) . ? C12 H12 0.9300 . ? C13 C14 1.390(3) . ? C14 C15 1.379(3) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C17 C18 1.313(3) . ? C17 H17 0.9300 . ? C18 H18 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 O1 S1 O2 116.34(9) . . ? O1 S1 N2 113.99(9) . . ? O2 S1 N2 105.64(8) . . ? O1 S1 C4 107.76(9) . . ? O2 S1 C4 107.65(9) . . ? N2 S1 C4 104.70(9) . . ? C8 S2 C7 90.93(12) . . ? C1 N1 H1N1 110.0(14) . . ? C1 N1 H2N1 111.3(15) . . ? H1N1 N1 H2N1 110.1(19) . . ? C7 N2 S1 120.10(14) . . ? C7 N3 C9 115.88(18) . . ? C7 N3 H1N3 122.1 . . ? C9 N3 H1N3 122.1 . . ? C2 C1 C6 118.7(2) . . ? C2 C1 N1 122.00(18) . . ? C6 C1 N1 119.30(19) . . ? C1 C2 C3 120.96(18) . . ? C1 C2 H2 119.5 . . ? C3 C2 H2 119.5 . . ? C2 C3 C4 119.73(19) . . ? C2 C3 H3A 120.1 . . ? C4 C3 H3A 120.1 . . ? C5 C4 C3 119.7(2) . . ? C5 C4 S1 119.24(15) . . ? C3 C4 S1 121.09(16) . . ? C6 C5 C4 120.33(18) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C1 120.6(2) . . ? C5 C6 H6A 119.7 . . ? C1 C6 H6A 119.7 . . ? N2 C7 N3 120.67(18) . . ? N2 C7 S2 130.56(16) . . ? N3 C7 S2 108.73(15) . . ? C9 C8 S2 111.81(18) . . ? C9 C8 H8 124.1 . . ? S2 C8 H8 124.1 . . ? C8 C9 N3 112.6(2) . . ? C8 C9 H9 123.7 . . ? N3 C9 H9 123.7 . . ? O3 S3 O4 117.38(9) . . ? O3 S3 N5 105.67(8) . . ? O4 S3 N5 113.01(9) . . ? O3 S3 C13 107.42(9) . . ? O4 S3 C13 107.88(9) . . ? N5 S3 C13 104.64(9) . . ? C17 S4 C16 90.73(11) . . ? C10 N4 H1N4 112.9(15) . . ? C10 N4 H2N4 112.5(15) . . ? H1N4 N4 H2N4 112(2) . . ? C16 N5 S3 120.00(13) . . ? C16 N6 C18 115.55(18) . . ? C16 N6 H1N6 122.2 . . ? C18 N6 H1N6 122.2 . . ? C15 C10 C11 118.9(2) . . ? C15 C10 N4 122.47(19) . . ? C11 C10 N4 118.62(19) . . ? C12 C11 C10 120.2(2) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C11 C12 C13 120.89(19) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C12 C13 C14 119.0(2) . . ? C12 C13 S3 119.15(15) . . ? C14 C13 S3 121.79(16) . . ? C15 C14 C13 120.22(19) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C10 120.72(19) . . ? C14 C15 H15 119.6 . . ? C10 C15 H15 119.6 . . ? N5 C16 N6 120.74(17) . . ? N5 C16 S4 130.13(15) . . ? N6 C16 S4 109.12(14) . . ? C18 C17 S4 111.45(18) . . ? C18 C17 H17 124.3 . . ? S4 C17 H17 124.3 . . ? C17 C18 N6 113.1(2) . . ? C17 C18 H18 123.4 . . ? N6 C18 H18 123.4 . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.212 _refine_diff_density_min -0.332 _refine_diff_density_rms 0.052 data_suthaz_f4 _database_code_depnum_ccdc_archive 'CCDC 761681' #TrackingRef 'suthaz_f4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H9 N3 O2 S2' _chemical_formula_weight 255.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, -z-1/2' _cell_length_a 10.8598(3) _cell_length_b 8.5347(2) _cell_length_c 11.4387(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.941(2) _cell_angle_gamma 90.00 _cell_volume 1059.59(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _exptl_crystal_description Parallelepiped _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.600 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.490 _cell_measurement_theta_max 29.0572 _cell_measurement_theta_min 2.5374 _cell_measurement_reflns_used 3157 _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _exptl_absorpt_correction_T_min 0.88384 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 16.1048 _diffrn_reflns_number 6307 _diffrn_reflns_av_R_equivalents 0.0206 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.5374 _diffrn_reflns_theta_max 26.370 _diffrn_orient_matrix_UB_11 0.0285105509 _diffrn_orient_matrix_UB_12 -0.0606852213 _diffrn_orient_matrix_UB_13 -0.0316539204 _diffrn_orient_matrix_UB_21 -0.0364605618 _diffrn_orient_matrix_UB_22 -0.0563764056 _diffrn_orient_matrix_UB_23 0.0285409129 _diffrn_orient_matrix_UB_31 -0.0461302163 _diffrn_orient_matrix_UB_32 0.0069964548 _diffrn_orient_matrix_UB_33 -0.0450286296 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -47.00 53.00 1.0000 9.7200 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.3903 77.0000 180.0000 0.0000 0.0000 100 #__ type_ start__ end____ width___ exp.time_ 2 omega -47.00 5.00 1.0000 9.7200 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.3903 77.0000 0.0000 0.0000 0.0000 52 #__ type_ start__ end____ width___ exp.time_ 3 omega -47.00 46.00 1.0000 9.7200 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.3903 77.0000 120.0000 0.0000 0.0000 93 #__ type_ start__ end____ width___ exp.time_ 4 omega -9.00 38.00 1.0000 9.7200 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 19.7341 77.0000 60.0000 0.0000 0.0000 47 ; _diffrn_ambient_temperature 293(2) _reflns_number_total 2149 _reflns_number_gt 1642 _reflns_threshold_expression >2sigma(I) _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (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^)+(0.0601P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2149 _refine_ls_number_parameters 153 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0462 _refine_ls_R_factor_gt 0.0315 _refine_ls_wR_factor_ref 0.1044 _refine_ls_wR_factor_gt 0.1005 _refine_ls_goodness_of_fit_ref 1.128 _refine_ls_restrained_S_all 1.128 _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 0.01503(5) 0.11590(6) 0.23768(5) 0.02863(18) Uani 1 1 d . . . S2 S 0.15608(7) 0.34106(9) 0.43076(6) 0.0560(2) Uani 1 1 d . . . N1 N -0.48462(17) 0.1911(2) 0.42781(17) 0.0330(4) Uani 1 1 d D . . H1N1 H -0.489(3) 0.168(3) 0.5027(11) 0.060(9) Uiso 1 1 d D . . H2N1 H -0.506(2) 0.2901(14) 0.4181(19) 0.036(7) Uiso 1 1 d D . . N2 N 0.05479(16) 0.2913(2) 0.20697(14) 0.0288(4) Uani 1 1 d . . . N3 N 0.11080(16) 0.5381(2) 0.27199(16) 0.0314(4) Uani 1 1 d . . . H1N3 H 0.0887 0.5806 0.2064 0.041 Uiso 1 1 calc R . . O1 O 0.09456(14) 0.04342(19) 0.32504(14) 0.0398(4) Uani 1 1 d . . . O2 O -0.00078(15) 0.03756(18) 0.12727(13) 0.0412(4) Uani 1 1 d . . . C1 C -0.36588(19) 0.1706(2) 0.38576(18) 0.0269(5) Uani 1 1 d . . . C2 C -0.27595(19) 0.0876(2) 0.44731(17) 0.0283(5) Uani 1 1 d . . . H2 H -0.2940 0.0424 0.5187 0.037 Uiso 1 1 calc R . . C3 C -0.15911(19) 0.0708(2) 0.40392(17) 0.0286(5) Uani 1 1 d . . . H3 H -0.0989 0.0160 0.4468 0.037 Uiso 1 1 calc R . . C4 C -0.13194(18) 0.1355(2) 0.29669(17) 0.0257(5) Uani 1 1 d . . . C5 C -0.2228(2) 0.2158(3) 0.23343(18) 0.0320(5) Uani 1 1 d . . . H5 H -0.2052 0.2590 0.1612 0.042 Uiso 1 1 calc R . . C6 C -0.3379(2) 0.2320(3) 0.27647(18) 0.0318(5) Uani 1 1 d . . . H6 H -0.3985 0.2846 0.2325 0.041 Uiso 1 1 calc R . . C7 C 0.10033(18) 0.3844(3) 0.29080(18) 0.0272(5) Uani 1 1 d . . . C8 C 0.1876(3) 0.5365(3) 0.4572(3) 0.0621(8) Uani 1 1 d . . . H8 H 0.2203 0.5754 0.5276 0.081 Uiso 1 1 calc R . . C9 C 0.1592(2) 0.6242(3) 0.3644(2) 0.0437(6) Uani 1 1 d . . . H9 H 0.1708 0.7321 0.3620 0.057 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 0.0384(3) 0.0228(3) 0.0250(3) 0.0001(2) 0.0049(2) -0.0015(2) S2 0.0852(5) 0.0430(4) 0.0378(4) 0.0034(3) -0.0264(3) -0.0090(4) N1 0.0398(11) 0.0279(11) 0.0316(11) -0.0010(9) 0.0057(8) 0.0021(8) N2 0.0386(10) 0.0238(10) 0.0240(9) 0.0003(7) 0.0009(7) -0.0053(8) N3 0.0341(9) 0.0270(11) 0.0331(10) -0.0017(8) 0.0008(7) -0.0041(8) O1 0.0423(9) 0.0360(10) 0.0412(9) 0.0125(8) 0.0036(7) 0.0066(7) O2 0.0634(11) 0.0302(9) 0.0308(9) -0.0108(7) 0.0129(7) -0.0101(8) C1 0.0357(11) 0.0197(10) 0.0253(11) -0.0045(9) 0.0015(8) -0.0039(9) C2 0.0403(12) 0.0277(12) 0.0168(10) 0.0018(9) 0.0022(9) -0.0043(9) C3 0.0374(11) 0.0248(12) 0.0231(11) 0.0019(9) -0.0041(9) -0.0007(9) C4 0.0353(11) 0.0202(11) 0.0215(10) -0.0015(8) 0.0005(8) -0.0041(8) C5 0.0428(13) 0.0312(12) 0.0218(11) 0.0069(9) -0.0011(9) -0.0006(10) C6 0.0372(12) 0.0293(12) 0.0287(12) 0.0052(9) -0.0029(9) 0.0021(9) C7 0.0276(10) 0.0276(12) 0.0265(11) 0.0007(9) 0.0011(8) -0.0012(9) C8 0.086(2) 0.0510(18) 0.0480(17) -0.0120(14) -0.0225(14) -0.0184(16) C9 0.0486(14) 0.0354(15) 0.0467(15) -0.0114(12) -0.0034(11) -0.0130(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 O2 1.4341(15) . ? S1 O1 1.4383(16) . ? S1 N2 1.6001(18) . ? S1 C4 1.762(2) . ? S2 C8 1.728(3) . ? S2 C7 1.732(2) . ? N1 C1 1.402(3) . ? N1 H1N1 0.884(10) . ? N1 H2N1 0.881(10) . ? N2 C7 1.328(3) . ? N3 C7 1.335(3) . ? N3 C9 1.377(3) . ? N3 H1N3 0.8600 . ? C1 C2 1.380(3) . ? C1 C6 1.398(3) . ? C2 C3 1.386(3) . ? C2 H2 0.9300 . ? C3 C4 1.386(3) . ? C3 H3 0.9300 . ? C4 C5 1.385(3) . ? C5 C6 1.367(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C8 C9 1.326(4) . ? C8 H8 0.9300 . ? C9 H9 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 O2 S1 O1 117.55(10) . . ? O2 S1 N2 105.54(9) . . ? O1 S1 N2 113.24(10) . . ? O2 S1 C4 107.37(9) . . ? O1 S1 C4 107.76(9) . . ? N2 S1 C4 104.48(9) . . ? C8 S2 C7 90.95(12) . . ? C1 N1 H1N1 112.9(18) . . ? C1 N1 H2N1 108.3(15) . . ? H1N1 N1 H2N1 108(2) . . ? C7 N2 S1 119.87(14) . . ? C7 N3 C9 115.66(19) . . ? C7 N3 H1N3 122.2 . . ? C9 N3 H1N3 122.2 . . ? C2 C1 C6 118.50(19) . . ? C2 C1 N1 122.14(19) . . ? C6 C1 N1 119.33(19) . . ? C1 C2 C3 120.75(19) . . ? C1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? C2 C3 C4 120.05(19) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C5 C4 C3 119.4(2) . . ? C5 C4 S1 119.01(16) . . ? C3 C4 S1 121.60(16) . . ? C6 C5 C4 120.39(19) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C1 120.9(2) . . ? C5 C6 H6 119.6 . . ? C1 C6 H6 119.6 . . ? N2 C7 N3 120.23(19) . . ? N2 C7 S2 130.50(17) . . ? N3 C7 S2 109.25(15) . . ? C9 C8 S2 111.4(2) . . ? C9 C8 H8 124.3 . . ? S2 C8 H8 124.3 . . ? C8 C9 N3 112.7(2) . . ? C8 C9 H9 123.7 . . ? N3 C9 H9 123.7 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.297 _refine_diff_density_min -0.283 _refine_diff_density_rms 0.050 data_sf51 _database_code_depnum_ccdc_archive 'CCDC 761682' #TrackingRef 'suthaz_f5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H9 N3 O2 S2' _chemical_formula_weight 255.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, -z-1/2' _cell_length_a 10.4125(5) _cell_length_b 15.2429(10) _cell_length_c 14.3121(6) _cell_angle_alpha 90.00 _cell_angle_beta 91.042(4) _cell_angle_gamma 90.00 _cell_volume 2271.2(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _exptl_crystal_description Parallelepiped _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.493 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 0.457 _cell_measurement_theta_max 28.5825 _cell_measurement_theta_min 2.6568 _cell_measurement_reflns_used 3049 _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _exptl_absorpt_correction_T_min 0.89394 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 16.1048 _diffrn_reflns_number 9761 _diffrn_reflns_av_R_equivalents 0.0380 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.6568 _diffrn_reflns_theta_max 25.350 _diffrn_orient_matrix_UB_11 -0.0150914515 _diffrn_orient_matrix_UB_12 0.0246642888 _diffrn_orient_matrix_UB_13 -0.0407030527 _diffrn_orient_matrix_UB_21 0.0306545880 _diffrn_orient_matrix_UB_22 -0.0320892112 _diffrn_orient_matrix_UB_23 -0.0277416434 _diffrn_orient_matrix_UB_31 -0.0588281546 _diffrn_orient_matrix_UB_32 -0.0231059565 _diffrn_orient_matrix_UB_33 -0.0051277873 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -53.00 52.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -20.0250 77.0000 330.0000 0.0000 0.0000 105 #__ type_ start__ end____ width___ exp.time_ 2 omega -2.00 52.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -20.0250 77.0000 90.0000 0.0000 0.0000 54 #__ type_ start__ end____ width___ exp.time_ 3 omega 26.00 91.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 22.2125 77.0000 210.0000 0.0000 0.0000 65 #__ type_ start__ end____ width___ exp.time_ 4 omega 40.00 65.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 22.2125 77.0000 240.0000 0.0000 0.0000 25 ; _diffrn_ambient_temperature 293(2) _reflns_number_total 4006 _reflns_number_gt 2355 _reflns_threshold_expression >2sigma(I) _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (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^)+(0.0646P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4006 _refine_ls_number_parameters 305 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1031 _refine_ls_R_factor_gt 0.0510 _refine_ls_wR_factor_ref 0.1288 _refine_ls_wR_factor_gt 0.1165 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.985 _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 0.32473(9) 0.09815(7) 0.64701(7) 0.0408(3) Uani 1 1 d . . . S2 S 0.16955(10) 0.12400(9) 0.44574(7) 0.0654(4) Uani 1 1 d . . . N1 N 0.4025(5) -0.2816(3) 0.6926(3) 0.0852(15) Uani 1 1 d D . . H1N1 H 0.355(3) -0.307(2) 0.735(2) 0.066(14) Uiso 1 1 d D . . H2N1 H 0.467(3) -0.309(2) 0.666(3) 0.067(14) Uiso 1 1 d D . . N2 N 0.1734(3) 0.1102(2) 0.6396(2) 0.0413(8) Uani 1 1 d . . . N3 N -0.0156(3) 0.1159(2) 0.5546(2) 0.0418(8) Uani 1 1 d . . . H1N3 H -0.0609 0.1118 0.6041 0.054 Uiso 1 1 calc R . . O1 O 0.3897(2) 0.12308(17) 0.56333(18) 0.0480(7) Uani 1 1 d . . . O2 O 0.3629(3) 0.14437(19) 0.73136(18) 0.0578(8) Uani 1 1 d . . . C1 C 0.3864(4) -0.1943(3) 0.6856(3) 0.0470(10) Uani 1 1 d . . . C2 C 0.2889(4) -0.1513(3) 0.7330(3) 0.0479(10) Uani 1 1 d . . . H2 H 0.2354 -0.1832 0.7717 0.062 Uiso 1 1 calc R . . C3 C 0.2711(4) -0.0626(3) 0.7232(2) 0.0436(10) Uani 1 1 d . . . H3A H 0.2068 -0.0348 0.7562 0.057 Uiso 1 1 calc R . . C4 C 0.3487(3) -0.0136(3) 0.6641(2) 0.0372(9) Uani 1 1 d . . . C5 C 0.4465(3) -0.0567(3) 0.6178(3) 0.0435(10) Uani 1 1 d . . . H5 H 0.4999 -0.0250 0.5788 0.057 Uiso 1 1 calc R . . C6 C 0.4655(4) -0.1451(3) 0.6285(3) 0.0445(10) Uani 1 1 d . . . H6A H 0.5320 -0.1725 0.5973 0.058 Uiso 1 1 calc R . . C7 C 0.1119(3) 0.1152(2) 0.5582(3) 0.0364(9) Uani 1 1 d . . . C8 C 0.0142(4) 0.1282(4) 0.4009(3) 0.0751(15) Uani 1 1 d . . . H8 H -0.0064 0.1331 0.3376 0.098 Uiso 1 1 calc R . . C9 C -0.0708(4) 0.1236(3) 0.4669(3) 0.0563(12) Uani 1 1 d . . . H9 H -0.1590 0.1254 0.4558 0.073 Uiso 1 1 calc R . . S3 S 0.82970(9) 0.05535(7) 0.82281(7) 0.0432(3) Uani 1 1 d . . . S4 S 0.68130(11) 0.10430(10) 1.01450(8) 0.0724(4) Uani 1 1 d . . . N4 N 0.8318(3) -0.3265(2) 0.8889(3) 0.0523(9) Uani 1 1 d D . . H1N4 H 0.903(2) -0.348(3) 0.915(3) 0.074(15) Uiso 1 1 d D . . H2N4 H 0.794(3) -0.360(2) 0.8455(19) 0.048(12) Uiso 1 1 d D . . N5 N 0.6840(3) 0.0867(2) 0.8215(2) 0.0422(8) Uani 1 1 d . . . N6 N 0.4997(3) 0.1225(2) 0.8992(2) 0.0534(9) Uani 1 1 d . . . H1N6 H 0.4550 0.1257 0.8482 0.069 Uiso 1 1 calc R . . O3 O 0.9053(2) 0.09668(17) 0.89638(18) 0.0520(7) Uani 1 1 d . . . O4 O 0.8727(3) 0.06871(19) 0.72888(18) 0.0612(8) Uani 1 1 d . . . C10 C 0.8334(3) -0.2383(3) 0.8713(3) 0.0389(9) Uani 1 1 d . . . C11 C 0.9161(4) -0.1835(3) 0.9211(3) 0.0534(11) Uani 1 1 d . . . H11 H 0.9741 -0.2075 0.9642 0.069 Uiso 1 1 calc R . . C12 C 0.9136(4) -0.0949(3) 0.9079(3) 0.0517(11) Uani 1 1 d . . . H12 H 0.9698 -0.0593 0.9420 0.067 Uiso 1 1 calc R . . C13 C 0.8286(3) -0.0576(2) 0.8444(2) 0.0373(9) Uani 1 1 d . . . C14 C 0.7457(4) -0.1118(3) 0.7941(3) 0.0430(10) Uani 1 1 d . . . H14 H 0.6879 -0.0876 0.7510 0.056 Uiso 1 1 calc R . . C15 C 0.7484(4) -0.2000(3) 0.8075(3) 0.0437(10) Uani 1 1 d . . . H15 H 0.6923 -0.2355 0.7732 0.057 Uiso 1 1 calc R . . C16 C 0.6245(4) 0.1031(2) 0.8997(3) 0.0413(9) Uani 1 1 d . . . C17 C 0.5298(5) 0.1302(4) 1.0537(3) 0.0902(18) Uani 1 1 d . . . H17 H 0.5100 0.1382 1.1162 0.117 Uiso 1 1 calc R . . C18 C 0.4468(4) 0.1372(3) 0.9847(3) 0.0715(14) Uani 1 1 d . . . H18 H 0.3606 0.1507 0.9927 0.093 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 0.0343(5) 0.0484(6) 0.0395(6) -0.0048(5) -0.0012(4) 0.0014(5) S2 0.0423(6) 0.1201(12) 0.0340(6) -0.0006(6) 0.0050(5) -0.0082(7) N1 0.105(4) 0.051(3) 0.102(4) 0.032(3) 0.060(3) 0.024(3) N2 0.0352(17) 0.057(2) 0.0317(18) -0.0023(16) 0.0018(13) 0.0062(16) N3 0.0326(16) 0.057(2) 0.0360(18) 0.0012(16) 0.0041(13) -0.0006(16) O1 0.0366(14) 0.0518(17) 0.0558(18) 0.0051(14) 0.0092(12) -0.0030(13) O2 0.0570(17) 0.0585(19) 0.0573(19) -0.0213(15) -0.0173(14) 0.0075(15) C1 0.050(2) 0.051(3) 0.039(2) 0.008(2) 0.0024(19) 0.007(2) C2 0.047(2) 0.057(3) 0.040(2) 0.012(2) 0.0128(18) 0.002(2) C3 0.042(2) 0.058(3) 0.031(2) -0.002(2) 0.0065(17) 0.005(2) C4 0.032(2) 0.050(2) 0.029(2) -0.0030(19) -0.0025(16) -0.0004(19) C5 0.037(2) 0.055(3) 0.039(2) 0.002(2) 0.0067(17) -0.003(2) C6 0.040(2) 0.049(3) 0.044(2) 0.005(2) 0.0074(18) 0.010(2) C7 0.037(2) 0.036(2) 0.036(2) -0.0033(18) 0.0052(16) -0.0026(18) C8 0.051(3) 0.138(5) 0.037(3) 0.003(3) -0.008(2) -0.005(3) C9 0.038(2) 0.082(3) 0.048(3) 0.002(2) -0.007(2) -0.002(2) S3 0.0431(6) 0.0492(6) 0.0374(6) 0.0033(5) 0.0033(4) -0.0026(5) S4 0.0586(7) 0.1220(12) 0.0366(6) -0.0061(7) -0.0015(5) 0.0099(8) N4 0.048(2) 0.044(2) 0.064(3) -0.008(2) -0.0130(19) 0.006(2) N5 0.0470(19) 0.047(2) 0.0325(18) -0.0022(15) 0.0013(14) 0.0050(16) N6 0.047(2) 0.069(2) 0.044(2) -0.0042(18) -0.0027(16) 0.0137(19) O3 0.0524(17) 0.0500(17) 0.0533(18) -0.0045(14) -0.0081(13) -0.0097(14) O4 0.0622(18) 0.077(2) 0.0456(18) 0.0115(15) 0.0190(14) -0.0027(16) C10 0.038(2) 0.039(2) 0.040(2) -0.008(2) 0.0001(17) 0.004(2) C11 0.054(3) 0.044(3) 0.060(3) -0.003(2) -0.025(2) 0.010(2) C12 0.049(2) 0.051(3) 0.054(3) -0.007(2) -0.022(2) -0.003(2) C13 0.034(2) 0.045(2) 0.032(2) -0.0066(19) 0.0023(17) 0.0003(19) C14 0.040(2) 0.053(3) 0.035(2) 0.000(2) -0.0091(17) 0.002(2) C15 0.039(2) 0.046(3) 0.045(2) -0.007(2) -0.0093(18) -0.004(2) C16 0.048(2) 0.040(2) 0.036(2) 0.0007(19) -0.0039(18) -0.002(2) C17 0.073(3) 0.156(6) 0.042(3) -0.014(3) 0.016(3) 0.015(4) C18 0.053(3) 0.107(4) 0.055(3) -0.018(3) 0.011(2) 0.010(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.437(3) . ? S1 O2 1.447(3) . ? S1 N2 1.588(3) . ? S1 C4 1.738(4) . ? S2 C8 1.731(4) . ? S2 C7 1.733(4) . ? N1 C1 1.345(5) . ? N1 H1N1 0.883(10) . ? N1 H2N1 0.885(10) . ? N2 C7 1.321(4) . ? N3 C7 1.328(4) . ? N3 C9 1.376(5) . ? N3 H1N3 0.8600 . ? C1 C6 1.390(5) . ? C1 C2 1.394(5) . ? C2 C3 1.372(5) . ? C2 H2 0.9300 . ? C3 C4 1.397(5) . ? C3 H3A 0.9300 . ? C4 C5 1.389(5) . ? C5 C6 1.371(5) . ? C5 H5 0.9300 . ? C6 H6A 0.9300 . ? C8 C9 1.308(5) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? S3 O4 1.439(3) . ? S3 O3 1.447(3) . ? S3 N5 1.590(3) . ? S3 C13 1.749(4) . ? S4 C17 1.729(5) . ? S4 C16 1.736(4) . ? N4 C10 1.368(5) . ? N4 H1N4 0.885(10) . ? N4 H2N4 0.889(10) . ? N5 C16 1.314(4) . ? N6 C16 1.332(5) . ? N6 C18 1.369(5) . ? N6 H1N6 0.8600 . ? C10 C11 1.388(5) . ? C10 C15 1.389(5) . ? C11 C12 1.363(5) . ? C11 H11 0.9300 . ? C12 C13 1.380(5) . ? C12 H12 0.9300 . ? C13 C14 1.387(5) . ? C14 C15 1.358(5) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C17 C18 1.305(6) . ? C17 H17 0.9300 . ? C18 H18 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 O1 S1 O2 116.10(17) . . ? O1 S1 N2 113.26(15) . . ? O2 S1 N2 104.86(16) . . ? O1 S1 C4 107.91(16) . . ? O2 S1 C4 108.87(17) . . ? N2 S1 C4 105.25(17) . . ? C8 S2 C7 90.59(19) . . ? C1 N1 H1N1 115(3) . . ? C1 N1 H2N1 121(3) . . ? H1N1 N1 H2N1 122(4) . . ? C7 N2 S1 122.0(3) . . ? C7 N3 C9 115.8(3) . . ? C7 N3 H1N3 122.1 . . ? C9 N3 H1N3 122.1 . . ? N1 C1 C6 120.2(4) . . ? N1 C1 C2 121.3(4) . . ? C6 C1 C2 118.5(4) . . ? C3 C2 C1 120.7(4) . . ? C3 C2 H2 119.6 . . ? C1 C2 H2 119.6 . . ? C2 C3 C4 120.7(3) . . ? C2 C3 H3A 119.6 . . ? C4 C3 H3A 119.6 . . ? C5 C4 C3 118.2(4) . . ? C5 C4 S1 120.0(3) . . ? C3 C4 S1 121.7(3) . . ? C6 C5 C4 121.1(4) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C1 120.7(4) . . ? C5 C6 H6A 119.6 . . ? C1 C6 H6A 119.6 . . ? N2 C7 N3 120.1(3) . . ? N2 C7 S2 130.7(3) . . ? N3 C7 S2 109.1(3) . . ? C9 C8 S2 111.7(3) . . ? C9 C8 H8 124.2 . . ? S2 C8 H8 124.2 . . ? C8 C9 N3 112.8(4) . . ? C8 C9 H9 123.6 . . ? N3 C9 H9 123.6 . . ? O4 S3 O3 116.35(17) . . ? O4 S3 N5 105.01(16) . . ? O3 S3 N5 112.61(16) . . ? O4 S3 C13 107.90(17) . . ? O3 S3 C13 107.76(17) . . ? N5 S3 C13 106.75(17) . . ? C17 S4 C16 90.7(2) . . ? C10 N4 H1N4 115(3) . . ? C10 N4 H2N4 116(2) . . ? H1N4 N4 H2N4 116(4) . . ? C16 N5 S3 120.8(3) . . ? C16 N6 C18 116.1(4) . . ? C16 N6 H1N6 122.0 . . ? C18 N6 H1N6 122.0 . . ? N4 C10 C11 120.5(4) . . ? N4 C10 C15 121.6(4) . . ? C11 C10 C15 117.8(4) . . ? C12 C11 C10 121.0(4) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C11 C12 C13 120.7(4) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C12 C13 C14 118.8(4) . . ? C12 C13 S3 121.1(3) . . ? C14 C13 S3 120.1(3) . . ? C15 C14 C13 120.4(4) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C10 121.4(4) . . ? C14 C15 H15 119.3 . . ? C10 C15 H15 119.3 . . ? N5 C16 N6 120.9(3) . . ? N5 C16 S4 130.6(3) . . ? N6 C16 S4 108.6(3) . . ? C18 C17 S4 111.6(4) . . ? C18 C17 H17 124.2 . . ? S4 C17 H17 124.2 . . ? C17 C18 N6 113.0(4) . . ? C17 C18 H18 123.5 . . ? N6 C18 H18 123.5 . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.261 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.072