# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Thomas Gelbrich' 'David S Hughes' 'Mike Hursthouse' 'T Threlfall' _publ_contact_author_name 'Thomas Gelbrich' _publ_contact_author_email GELBRICH@SOTON.AC.UK _publ_section_title ; Packing similarity in polymorphs of sulfathiazole ; # Attachment 'sulfathiazole.cif' data_form_I _database_code_depnum_ccdc_archive 'CCDC 687586' _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 10.534(2) _cell_length_b 12.936(3) _cell_length_c 17.191(3) _cell_angle_alpha 90.00 _cell_angle_beta 107.77(3) _cell_angle_gamma 90.00 _cell_volume 2230.8(9) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.520 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 0.465 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8926 _exptl_absorpt_correction_T_max 0.9637 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19523 _diffrn_reflns_av_R_equivalents 0.0878 _diffrn_reflns_av_sigmaI/netI 0.0627 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 25.03 _reflns_number_total 3938 _reflns_number_gt 2890 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0521P)^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 3938 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0646 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.1016 _refine_ls_wR_factor_gt 0.0917 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 S11 S 0.69239(6) 0.57187(5) -0.08959(4) 0.02329(18) Uani 1 1 d . . . S12 S 0.84723(7) 0.75569(5) 0.03577(4) 0.0300(2) Uani 1 1 d . . . S21 S 0.81776(6) 0.07347(5) 0.11850(4) 0.02438(19) Uani 1 1 d . . . S22 S 0.63514(7) 0.08306(7) -0.07338(5) 0.0379(2) Uani 1 1 d . . . O11 O 0.66220(17) 0.46787(14) -0.11992(11) 0.0313(5) Uani 1 1 d . . . O12 O 0.62019(17) 0.61186(15) -0.03712(11) 0.0320(5) Uani 1 1 d . . . O21 O 0.91444(18) 0.03367(14) 0.19157(11) 0.0337(5) Uani 1 1 d . . . O22 O 0.68019(17) 0.04393(14) 0.10245(11) 0.0315(5) Uani 1 1 d . . . N11 N 0.5716(2) 0.8423(2) -0.38022(16) 0.0311(6) Uani 1 1 d . . . N12 N 0.85087(19) 0.57011(16) -0.04551(12) 0.0217(5) Uani 1 1 d . . . N13 N 1.0391(2) 0.63256(19) 0.05217(14) 0.0261(5) Uani 1 1 d . . . N21 N 0.8434(3) 0.52760(19) 0.15165(15) 0.0295(6) Uani 1 1 d . . . N22 N 0.8744(2) 0.03564(16) 0.04598(13) 0.0243(5) Uani 1 1 d . . . N23 N 0.8466(2) 0.01147(17) -0.09147(13) 0.0251(5) Uani 1 1 d . . . C11 C 0.5977(2) 0.7778(2) -0.31347(16) 0.0234(6) Uani 1 1 d . . . C12 C 0.6640(2) 0.6845(2) -0.31092(16) 0.0224(6) Uani 1 1 d . . . C13 C 0.6944(2) 0.6225(2) -0.24236(15) 0.0210(6) Uani 1 1 d . . . C14 C 0.6594(2) 0.65395(19) -0.17450(15) 0.0208(6) Uani 1 1 d . . . C15 C 0.5924(3) 0.7465(2) -0.17654(17) 0.0256(6) Uani 1 1 d . . . C16 C 0.5602(3) 0.8072(2) -0.24508(16) 0.0268(6) Uani 1 1 d . . . C17 C 0.9102(2) 0.64180(19) 0.00850(15) 0.0215(6) Uani 1 1 d . . . C18 C 1.0876(3) 0.7089(2) 0.10979(18) 0.0326(7) Uani 1 1 d . . . C19 C 0.9986(3) 0.7810(2) 0.10922(19) 0.0337(7) Uani 1 1 d . . . C21 C 0.8373(2) 0.4232(2) 0.13989(15) 0.0224(6) Uani 1 1 d . . . C22 C 0.9523(3) 0.3621(2) 0.16839(16) 0.0254(6) Uani 1 1 d . . . C23 C 0.9471(3) 0.2572(2) 0.15965(17) 0.0253(6) Uani 1 1 d . . . C24 C 0.8260(2) 0.2082(2) 0.12317(15) 0.0210(6) Uani 1 1 d . . . C25 C 0.7110(3) 0.2675(2) 0.09268(16) 0.0250(6) Uani 1 1 d . . . C26 C 0.7169(3) 0.3732(2) 0.10050(17) 0.0274(6) Uani 1 1 d . . . C27 C 0.7984(2) 0.0408(2) -0.03194(16) 0.0235(6) Uani 1 1 d . . . C28 C 0.7626(3) 0.0268(2) -0.16958(18) 0.0307(7) Uani 1 1 d . . . C29 C 0.6454(3) 0.0657(2) -0.17146(18) 0.0371(7) Uani 1 1 d . . . H10 H 0.501(3) 0.890(3) -0.386(2) 0.054(10) Uiso 1 1 d . . . H11 H 0.580(3) 0.815(2) -0.4230(19) 0.039(9) Uiso 1 1 d . . . H12 H 0.685(2) 0.6612(19) -0.3570(16) 0.022(7) Uiso 1 1 d . . . H13 H 0.739(2) 0.5590(19) -0.2414(15) 0.019(7) Uiso 1 1 d . . . H15 H 0.566(2) 0.7633(18) -0.1333(16) 0.018(7) Uiso 1 1 d . . . H16 H 0.507(2) 0.867(2) -0.2491(16) 0.029(7) Uiso 1 1 d . . . H17 H 1.083(3) 0.578(2) 0.0520(17) 0.029(8) Uiso 1 1 d . . . H18 H 1.174(3) 0.700(2) 0.1446(18) 0.038(8) Uiso 1 1 d . . . H19 H 1.008(2) 0.837(2) 0.1424(16) 0.026(7) Uiso 1 1 d . . . H20 H 0.764(3) 0.566(2) 0.1360(17) 0.030(8) Uiso 1 1 d . . . H21 H 0.919(3) 0.555(2) 0.1818(19) 0.039(9) Uiso 1 1 d . . . H22 H 1.033(3) 0.397(2) 0.1948(17) 0.029(7) Uiso 1 1 d . . . H23 H 1.022(3) 0.217(2) 0.1784(16) 0.029(7) Uiso 1 1 d . . . H25 H 0.629(3) 0.235(2) 0.0700(18) 0.035(8) Uiso 1 1 d . . . H26 H 0.640(3) 0.416(2) 0.0812(17) 0.032(8) Uiso 1 1 d . . . H27 H 0.929(3) -0.011(2) -0.0800(18) 0.043(9) Uiso 1 1 d . . . H28 H 0.793(3) 0.006(2) -0.2127(17) 0.029(7) Uiso 1 1 d . . . H29 H 0.569(3) 0.079(3) -0.216(2) 0.067(11) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S11 0.0192(3) 0.0310(4) 0.0177(4) 0.0020(3) 0.0026(3) -0.0022(3) S12 0.0308(4) 0.0253(4) 0.0330(4) -0.0024(3) 0.0084(3) 0.0019(3) S21 0.0241(4) 0.0257(4) 0.0213(4) 0.0038(3) 0.0040(3) 0.0004(3) S22 0.0223(4) 0.0581(6) 0.0270(4) -0.0072(4) -0.0017(3) 0.0134(3) O11 0.0329(10) 0.0280(11) 0.0277(11) 0.0027(9) 0.0014(9) -0.0087(8) O12 0.0259(10) 0.0508(13) 0.0216(10) 0.0032(9) 0.0105(9) 0.0026(9) O21 0.0392(11) 0.0333(12) 0.0223(11) 0.0092(9) -0.0001(9) 0.0041(9) O22 0.0266(10) 0.0339(12) 0.0350(12) 0.0007(9) 0.0109(9) -0.0060(8) N11 0.0347(14) 0.0305(15) 0.0296(15) 0.0081(12) 0.0122(12) 0.0060(11) N12 0.0169(11) 0.0278(12) 0.0173(12) -0.0023(10) 0.0007(9) -0.0005(9) N13 0.0215(12) 0.0259(14) 0.0266(14) -0.0027(11) 0.0011(10) -0.0016(10) N21 0.0312(14) 0.0269(14) 0.0264(14) 0.0006(11) 0.0027(12) -0.0017(12) N22 0.0214(11) 0.0252(13) 0.0223(13) 0.0007(10) 0.0006(10) 0.0045(9) N23 0.0196(12) 0.0289(13) 0.0243(13) 0.0005(10) 0.0027(11) 0.0056(10) C11 0.0205(13) 0.0269(15) 0.0210(15) 0.0017(12) 0.0036(12) -0.0038(11) C12 0.0191(13) 0.0303(16) 0.0191(15) -0.0032(12) 0.0077(12) 0.0013(11) C13 0.0157(12) 0.0243(15) 0.0219(15) 0.0010(12) 0.0040(11) 0.0024(11) C14 0.0172(12) 0.0279(15) 0.0144(14) 0.0007(11) 0.0005(11) -0.0015(11) C15 0.0264(14) 0.0321(16) 0.0188(15) -0.0038(12) 0.0076(13) 0.0028(12) C16 0.0292(15) 0.0245(16) 0.0257(16) -0.0005(13) 0.0068(13) 0.0045(13) C17 0.0219(13) 0.0239(15) 0.0195(14) 0.0044(12) 0.0074(12) -0.0010(11) C18 0.0301(16) 0.0338(18) 0.0270(17) -0.0050(14) -0.0018(14) -0.0084(14) C19 0.0390(17) 0.0239(16) 0.0357(18) -0.0086(14) 0.0077(15) -0.0062(14) C21 0.0259(14) 0.0261(15) 0.0158(14) 0.0003(11) 0.0073(12) -0.0007(12) C22 0.0187(14) 0.0316(16) 0.0239(15) -0.0056(12) 0.0034(12) -0.0052(12) C23 0.0186(14) 0.0293(16) 0.0255(16) -0.0007(12) 0.0029(12) 0.0040(12) C24 0.0218(13) 0.0258(15) 0.0148(13) 0.0003(11) 0.0049(11) 0.0008(11) C25 0.0178(14) 0.0320(17) 0.0235(16) -0.0031(12) 0.0036(12) -0.0024(12) C26 0.0209(14) 0.0320(17) 0.0261(16) -0.0016(13) 0.0023(12) 0.0052(13) C27 0.0173(13) 0.0232(15) 0.0257(16) -0.0003(12) 0.0003(12) 0.0004(11) C28 0.0295(16) 0.0353(18) 0.0224(17) -0.0025(13) 0.0007(13) 0.0033(13) C29 0.0297(16) 0.052(2) 0.0209(17) -0.0072(14) -0.0046(13) 0.0110(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S11 O12 1.4417(19) . ? S11 O11 1.4427(19) . ? S11 N12 1.609(2) . ? S11 C14 1.752(3) . ? S12 C19 1.737(3) . ? S12 C17 1.738(3) . ? S21 O22 1.4417(18) . ? S21 O21 1.4489(19) . ? S21 N22 1.613(2) . ? S21 C24 1.746(3) . ? S22 C27 1.736(2) . ? S22 C29 1.737(3) . ? N11 C11 1.377(3) . ? N11 H10 0.95(3) . ? N11 H11 0.84(3) . ? N12 C17 1.326(3) . ? N13 C17 1.342(3) . ? N13 C18 1.382(4) . ? N13 H17 0.85(3) . ? N21 C21 1.365(3) . ? N21 H20 0.94(3) . ? N21 H21 0.88(3) . ? N22 C27 1.336(3) . ? N23 C27 1.329(3) . ? N23 C28 1.378(3) . ? N23 H27 0.88(3) . ? C11 C12 1.388(4) . ? C11 C16 1.403(4) . ? C12 C13 1.380(4) . ? C12 H12 0.94(3) . ? C13 C14 1.387(3) . ? C13 H13 0.95(2) . ? C14 C15 1.385(4) . ? C15 C16 1.369(4) . ? C15 H15 0.90(2) . ? C16 H16 0.94(3) . ? C18 C19 1.320(4) . ? C18 H18 0.93(3) . ? C19 H19 0.91(3) . ? C21 C26 1.400(4) . ? C21 C22 1.403(4) . ? C22 C23 1.364(4) . ? C22 H22 0.95(3) . ? C23 C24 1.391(4) . ? C23 H23 0.92(3) . ? C24 C25 1.394(4) . ? C25 C26 1.373(4) . ? C25 H25 0.94(3) . ? C26 H26 0.95(3) . ? C28 C29 1.324(4) . ? C28 H28 0.93(3) . ? C29 H29 0.94(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O12 S11 O11 117.42(11) . . ? O12 S11 N12 112.33(11) . . ? O11 S11 N12 103.86(11) . . ? O12 S11 C14 107.19(12) . . ? O11 S11 C14 107.36(12) . . ? N12 S11 C14 108.32(11) . . ? C19 S12 C17 90.85(13) . . ? O22 S21 O21 118.12(12) . . ? O22 S21 N22 111.02(11) . . ? O21 S21 N22 103.55(11) . . ? O22 S21 C24 107.83(11) . . ? O21 S21 C24 107.64(12) . . ? N22 S21 C24 108.27(11) . . ? C27 S22 C29 90.58(14) . . ? C11 N11 H10 115.7(19) . . ? C11 N11 H11 115(2) . . ? H10 N11 H11 118(3) . . ? C17 N12 S11 121.28(18) . . ? C17 N13 C18 115.3(2) . . ? C17 N13 H17 122.2(19) . . ? C18 N13 H17 121.2(19) . . ? C21 N21 H20 118.8(17) . . ? C21 N21 H21 118.5(19) . . ? H20 N21 H21 122(3) . . ? C27 N22 S21 120.65(18) . . ? C27 N23 C28 115.3(2) . . ? C27 N23 H27 120(2) . . ? C28 N23 H27 124(2) . . ? N11 C11 C12 121.6(2) . . ? N11 C11 C16 119.9(3) . . ? C12 C11 C16 118.5(2) . . ? C13 C12 C11 121.0(2) . . ? C13 C12 H12 118.8(15) . . ? C11 C12 H12 120.1(15) . . ? C12 C13 C14 119.7(2) . . ? C12 C13 H13 120.3(15) . . ? C14 C13 H13 120.0(15) . . ? C15 C14 C13 119.8(2) . . ? C15 C14 S11 120.99(19) . . ? C13 C14 S11 119.1(2) . . ? C16 C15 C14 120.5(3) . . ? C16 C15 H15 121.0(16) . . ? C14 C15 H15 118.3(16) . . ? C15 C16 C11 120.4(3) . . ? C15 C16 H16 121.2(16) . . ? C11 C16 H16 118.2(16) . . ? N12 C17 N13 120.6(2) . . ? N12 C17 S12 130.15(19) . . ? N13 C17 S12 109.21(19) . . ? C19 C18 N13 113.2(3) . . ? C19 C18 H18 130.0(18) . . ? N13 C18 H18 116.7(18) . . ? C18 C19 S12 111.4(2) . . ? C18 C19 H19 128.3(17) . . ? S12 C19 H19 120.2(16) . . ? N21 C21 C26 121.5(2) . . ? N21 C21 C22 120.6(2) . . ? C26 C21 C22 117.9(3) . . ? C23 C22 C21 121.3(2) . . ? C23 C22 H22 121.9(16) . . ? C21 C22 H22 116.8(16) . . ? C22 C23 C24 120.3(3) . . ? C22 C23 H23 121.7(17) . . ? C24 C23 H23 118.0(17) . . ? C23 C24 C25 119.4(3) . . ? C23 C24 S21 120.1(2) . . ? C25 C24 S21 120.5(2) . . ? C26 C25 C24 120.2(3) . . ? C26 C25 H25 120.1(17) . . ? C24 C25 H25 119.6(17) . . ? C25 C26 C21 120.9(3) . . ? C25 C26 H26 122.1(17) . . ? C21 C26 H26 117.0(17) . . ? N23 C27 N22 120.3(2) . . ? N23 C27 S22 109.70(19) . . ? N22 C27 S22 130.0(2) . . ? C29 C28 N23 113.2(3) . . ? C29 C28 H28 129.3(17) . . ? N23 C28 H28 117.4(16) . . ? C28 C29 S22 111.1(2) . . ? C28 C29 H29 130(2) . . ? S22 C29 H29 118(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O12 S11 N12 C17 -33.3(2) . . . . ? O11 S11 N12 C17 -161.2(2) . . . . ? C14 S11 N12 C17 84.9(2) . . . . ? O22 S21 N22 C27 39.3(2) . . . . ? O21 S21 N22 C27 167.0(2) . . . . ? C24 S21 N22 C27 -78.9(2) . . . . ? N11 C11 C12 C13 177.3(2) . . . . ? C16 C11 C12 C13 -1.0(4) . . . . ? C11 C12 C13 C14 -0.6(4) . . . . ? C12 C13 C14 C15 1.0(4) . . . . ? C12 C13 C14 S11 177.32(19) . . . . ? O12 S11 C14 C15 9.0(2) . . . . ? O11 S11 C14 C15 136.0(2) . . . . ? N12 S11 C14 C15 -112.4(2) . . . . ? O12 S11 C14 C13 -167.18(19) . . . . ? O11 S11 C14 C13 -40.2(2) . . . . ? N12 S11 C14 C13 71.4(2) . . . . ? C13 C14 C15 C16 0.1(4) . . . . ? S11 C14 C15 C16 -176.1(2) . . . . ? C14 C15 C16 C11 -1.7(4) . . . . ? N11 C11 C16 C15 -176.2(3) . . . . ? C12 C11 C16 C15 2.2(4) . . . . ? S11 N12 C17 N13 171.72(18) . . . . ? S11 N12 C17 S12 -8.5(3) . . . . ? C18 N13 C17 N12 -176.4(2) . . . . ? C18 N13 C17 S12 3.8(3) . . . . ? C19 S12 C17 N12 177.3(3) . . . . ? C19 S12 C17 N13 -2.9(2) . . . . ? C17 N13 C18 C19 -2.8(4) . . . . ? N13 C18 C19 S12 0.4(3) . . . . ? C17 S12 C19 C18 1.4(2) . . . . ? N21 C21 C22 C23 177.7(2) . . . . ? C26 C21 C22 C23 -1.3(4) . . . . ? C21 C22 C23 C24 -1.1(4) . . . . ? C22 C23 C24 C25 2.6(4) . . . . ? C22 C23 C24 S21 -175.5(2) . . . . ? O22 S21 C24 C23 162.1(2) . . . . ? O21 S21 C24 C23 33.6(2) . . . . ? N22 S21 C24 C23 -77.7(2) . . . . ? O22 S21 C24 C25 -16.0(2) . . . . ? O21 S21 C24 C25 -144.4(2) . . . . ? N22 S21 C24 C25 104.2(2) . . . . ? C23 C24 C25 C26 -1.7(4) . . . . ? S21 C24 C25 C26 176.5(2) . . . . ? C24 C25 C26 C21 -0.8(4) . . . . ? N21 C21 C26 C25 -176.7(2) . . . . ? C22 C21 C26 C25 2.2(4) . . . . ? C28 N23 C27 N22 -175.7(2) . . . . ? C28 N23 C27 S22 3.8(3) . . . . ? S21 N22 C27 N23 178.61(19) . . . . ? S21 N22 C27 S22 -0.8(4) . . . . ? C29 S22 C27 N23 -3.5(2) . . . . ? C29 S22 C27 N22 175.9(3) . . . . ? C27 N23 C28 C29 -2.0(4) . . . . ? N23 C28 C29 S22 -0.9(4) . . . . ? C27 S22 C29 C28 2.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.315 _refine_diff_density_min -0.475 _refine_diff_density_rms 0.077 data_SUTHAZ05_form_II_CSD _database_code_depnum_ccdc_archive 'CCDC 137993' _audit_creation_date 2000-01-11 _audit_creation_method CSD-ConQuest-V1 _database_code_CSD SUTHAZ05 _chemical_formula_sum 'C9 H9 N3 O2 S2' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2+x,1/2-y,1/2+z 3 -x,-y,-z 4 -1/2-x,-1/2+y,-1/2-z _cell_length_a 10.399(2) _cell_length_b 15.132(3) _cell_length_c 14.280(3) _cell_angle_alpha 90 _cell_angle_beta 91.21(3) _cell_angle_gamma 90 _cell_formula_units_Z 8 loop_ _atom_type_symbol _atom_type_radius_bond _atom_type_radius_vdwaals C 0.68 1.7 H 0.23 1.2 O 0.68 1.7 S 1.02 2.1 N 0.68 1.55 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z S1 S 0.17581(7) 0.40001(6) -0.14444(6) S2 S 0.33345(8) 0.37399(7) 0.05805(6) O1 O 0.1372(2) 0.35111(16) -0.22744(16) O2 O 0.11201(19) 0.37652(15) -0.05911(16) N1 N 0.0924(3) 0.7823(2) -0.1961(3) H1 H 0.129(3) 0.816(2) -0.240(2) H2 H 0.036(4) 0.815(3) -0.159(3) N2 N 0.3282(2) 0.38965(19) -0.13676(18) N3 N 0.5198(2) 0.38573(18) -0.05178(19) H3 H 0.56460 0.39120 -0.10140 C1 C 0.1098(3) 0.6944(2) -0.1880(2) C2 C 0.2078(3) 0.6499(2) -0.2361(2) H4 H 0.26010 0.68140 -0.27620 C3 C 0.2270(3) 0.5608(2) -0.2246(2) H5 H 0.29180 0.53250 -0.25710 C4 C 0.1496(3) 0.5122(2) -0.1643(2) C5 C 0.0505(3) 0.5555(2) -0.1180(2) H6 H -0.00270 0.52380 -0.07870 C6 C 0.0312(3) 0.6450(2) -0.1301(2) H7 H -0.03530 0.67270 -0.09910 C7 C 0.3906(3) 0.3844(2) -0.0549(2) C8 C 0.5758(3) 0.3777(3) 0.0362(2) H8 H 0.66420 0.37660 0.04750 C9 C 0.4893(3) 0.3716(3) 0.1032(3) H9 H 0.50990 0.36670 0.16670 S3 S 0.17103(7) 0.05317(6) 0.17760(6) S4 S 0.32040(8) 0.10341(8) -0.01384(6) O3 O 0.0954(2) 0.09562(15) 0.10411(16) O4 O 0.1264(2) 0.06537(17) 0.27229(16) N4 N 0.1688(3) -0.3323(2) 0.1077(2) H10 H 0.100(2) -0.356(2) 0.077(2) H11 H 0.192(3) -0.366(2) 0.1568(18) N5 N 0.3178(2) 0.08555(18) 0.18073(19) N6 N 0.5033(3) 0.1230(2) 0.1031(2) H12 H 0.54740 0.12670 0.15460 C10 C 0.1670(3) -0.2432(2) 0.1252(2) C11 C 0.0845(3) -0.1869(2) 0.0750(2) H13 H 0.02670 -0.21050 0.03120 C12 C 0.0873(3) -0.0971(2) 0.0894(2) H14 H 0.03140 -0.06080 0.05520 C13 C 0.1724(3) -0.0601(2) 0.1542(2) C14 C 0.2561(3) -0.1149(2) 0.2054(2) H15 H 0.31340 -0.09060 0.24920 C15 C 0.2536(3) -0.2050(2) 0.1910(2) H16 H 0.30980 -0.24110 0.22510 C16 C 0.3776(3) 0.1022(2) 0.1020(2) C17 C 0.5577(4) 0.1382(3) 0.0176(3) H17 H 0.64370 0.15280 0.00990 C18 C 0.4728(4) 0.1297(3) -0.0526(3) H18 H 0.49260 0.13700 -0.11530 data_form_III _database_code_depnum_ccdc_archive 'CCDC 687587' _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 17.448(3) _cell_length_b 8.498(2) _cell_length_c 15.511(3) _cell_angle_alpha 90.00 _cell_angle_beta 112.81(3) _cell_angle_gamma 90.00 _cell_volume 2120.0(9) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.600 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 0.489 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9085 _exptl_absorpt_correction_T_max 0.9302 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) __diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17182 _diffrn_reflns_av_R_equivalents 0.1049 _diffrn_reflns_av_sigmaI/netI 0.0904 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 25.03 _reflns_number_total 3723 _reflns_number_gt 2239 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0463P)^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 3723 _refine_ls_number_parameters 361 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1024 _refine_ls_R_factor_gt 0.0485 _refine_ls_wR_factor_ref 0.1072 _refine_ls_wR_factor_gt 0.0946 _refine_ls_goodness_of_fit_ref 0.930 _refine_ls_restrained_S_all 0.929 _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 S11 S 0.38389(6) 0.89999(10) 0.05813(5) 0.0224(2) Uani 1 1 d . . . S12 S 0.35594(7) 0.67522(11) -0.12332(6) 0.0358(3) Uani 1 1 d . . . O11 O 0.43201(15) 0.9805(3) 0.14457(14) 0.0265(6) Uani 1 1 d . . . O12 O 0.37758(15) 0.9780(3) -0.02689(14) 0.0266(6) Uani 1 1 d . . . N11 N 0.0429(2) 0.8058(3) 0.04887(19) 0.0229(7) Uani 1 1 d D . . N12 N 0.42098(19) 0.7271(3) 0.06960(17) 0.0243(7) Uani 1 1 d . . . N13 N 0.41198(18) 0.4768(3) 0.00738(18) 0.0226(7) Uani 1 1 d D . . C11 C 0.1228(2) 0.8299(4) 0.0495(2) 0.0201(8) Uani 1 1 d . . . C12 C 0.1921(2) 0.7666(4) 0.1219(2) 0.0217(9) Uani 1 1 d . . . C13 C 0.2708(3) 0.7879(4) 0.1239(2) 0.0229(9) Uani 1 1 d . . . C14 C 0.2825(2) 0.8755(4) 0.0544(2) 0.0202(8) Uani 1 1 d . . . C15 C 0.2139(2) 0.9412(4) -0.0170(2) 0.0218(9) Uani 1 1 d . . . C16 C 0.1357(2) 0.9194(4) -0.0190(2) 0.0195(8) Uani 1 1 d . . . C17 C 0.3990(2) 0.6322(4) -0.0041(2) 0.0230(8) Uani 1 1 d . . . C18 C 0.3886(3) 0.3902(5) -0.0737(2) 0.0296(9) Uani 1 1 d . . . C19 C 0.3571(3) 0.4784(4) -0.1498(3) 0.0371(11) Uani 1 1 d . . . S21 S 0.10697(6) 0.38054(10) 0.18198(5) 0.0227(2) Uani 1 1 d . . . S22 S 0.13791(7) 0.14944(11) 0.36058(5) 0.0360(3) Uani 1 1 d . . . O21 O 0.05793(15) 0.4621(3) 0.09711(14) 0.0283(6) Uani 1 1 d . . . O22 O 0.11267(15) 0.4496(3) 0.26910(14) 0.0264(6) Uani 1 1 d . . . N21 N 0.4468(2) 0.3251(4) 0.18213(19) 0.0249(7) Uani 1 1 d D . . N22 N 0.07236(18) 0.2041(3) 0.16818(16) 0.0215(7) Uani 1 1 d . . . N23 N 0.08016(19) -0.0471(3) 0.22929(17) 0.0228(7) Uani 1 1 d D . . C21 C 0.3679(2) 0.3390(4) 0.1853(2) 0.0200(8) Uani 1 1 d . . . C22 C 0.2995(3) 0.2777(4) 0.1113(2) 0.0241(9) Uani 1 1 d . . . C23 C 0.2210(3) 0.2898(4) 0.1116(2) 0.0252(9) Uani 1 1 d . . . C24 C 0.2085(2) 0.3648(4) 0.1857(2) 0.0202(8) Uani 1 1 d . . . C25 C 0.2768(2) 0.4266(4) 0.2589(2) 0.0225(9) Uani 1 1 d . . . C26 C 0.3556(2) 0.4148(4) 0.2586(2) 0.0226(9) Uani 1 1 d . . . C27 C 0.0934(2) 0.1072(4) 0.2418(2) 0.0227(8) Uani 1 1 d . . . C28 C 0.1057(2) -0.1349(4) 0.3107(2) 0.0302(10) Uani 1 1 d . . . C29 C 0.1377(3) -0.0492(4) 0.3866(3) 0.0384(11) Uani 1 1 d . . . H10 H 0.0052(19) 0.821(4) -0.0079(15) 0.039(12) Uiso 1 1 d D . . H11 H 0.038(2) 0.707(2) 0.064(2) 0.038(11) Uiso 1 1 d D . . H12 H 0.1815(19) 0.709(3) 0.1685(19) 0.016(8) Uiso 1 1 d . . . H13 H 0.314(2) 0.741(3) 0.1720(19) 0.011(8) Uiso 1 1 d . . . H15 H 0.226(2) 1.001(4) -0.061(2) 0.027(9) Uiso 1 1 d . . . H16 H 0.087(2) 0.961(3) -0.070(2) 0.021(9) Uiso 1 1 d . . . H17 H 0.431(2) 0.435(4) 0.0640(14) 0.027(10) Uiso 1 1 d D . . H18 H 0.397(2) 0.284(4) -0.067(2) 0.027(10) Uiso 1 1 d . . . H19 H 0.340(2) 0.450(4) -0.209(2) 0.042(12) Uiso 1 1 d . . . H20 H 0.4873(18) 0.360(4) 0.2329(17) 0.043(12) Uiso 1 1 d D . . H21 H 0.456(2) 0.232(2) 0.1679(19) 0.017(9) Uiso 1 1 d D . . H22 H 0.309(2) 0.225(4) 0.058(2) 0.044(11) Uiso 1 1 d . . . H23 H 0.173(2) 0.244(4) 0.066(2) 0.019(9) Uiso 1 1 d . . . H25 H 0.270(2) 0.482(4) 0.310(2) 0.023(9) Uiso 1 1 d . . . H26 H 0.403(2) 0.447(4) 0.312(2) 0.026(9) Uiso 1 1 d . . . H27 H 0.063(3) -0.088(4) 0.1721(16) 0.059(13) Uiso 1 1 d D . . H28 H 0.097(2) -0.241(4) 0.301(2) 0.027(10) Uiso 1 1 d . . . H29 H 0.161(2) -0.073(4) 0.451(2) 0.039(11) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S11 0.0240(6) 0.0206(5) 0.0196(4) 0.0007(4) 0.0051(4) 0.0021(4) S12 0.0517(8) 0.0297(6) 0.0219(5) 0.0002(4) 0.0100(5) 0.0057(5) O11 0.0265(16) 0.0210(13) 0.0242(12) -0.0038(10) 0.0011(11) -0.0020(11) O12 0.0259(16) 0.0287(14) 0.0240(12) 0.0085(10) 0.0082(11) 0.0032(12) N11 0.023(2) 0.0202(18) 0.0218(16) 0.0018(13) 0.0046(14) -0.0021(15) N12 0.028(2) 0.0221(17) 0.0202(14) 0.0001(12) 0.0060(13) 0.0063(14) N13 0.026(2) 0.0224(18) 0.0199(15) 0.0009(13) 0.0088(14) 0.0017(14) C11 0.023(2) 0.0155(19) 0.0192(17) -0.0019(14) 0.0049(15) 0.0008(16) C12 0.026(3) 0.0170(19) 0.0207(18) 0.0009(15) 0.0076(17) 0.0014(17) C13 0.027(3) 0.021(2) 0.0132(17) 0.0023(15) -0.0009(17) 0.0027(18) C14 0.025(2) 0.0176(18) 0.0173(17) -0.0057(14) 0.0070(15) -0.0028(16) C15 0.027(3) 0.020(2) 0.0126(17) -0.0016(14) 0.0018(16) -0.0009(17) C16 0.018(2) 0.0203(19) 0.0142(17) -0.0036(14) -0.0004(16) 0.0017(17) C17 0.021(2) 0.023(2) 0.0268(18) 0.0012(16) 0.0114(16) -0.0014(17) C18 0.037(3) 0.022(2) 0.030(2) -0.0040(18) 0.0134(18) -0.003(2) C19 0.051(3) 0.031(2) 0.026(2) -0.0055(18) 0.011(2) 0.000(2) S21 0.0242(6) 0.0194(5) 0.0207(5) 0.0004(3) 0.0047(4) -0.0008(4) S22 0.0561(8) 0.0281(6) 0.0190(5) 0.0004(4) 0.0094(5) -0.0050(5) O21 0.0291(16) 0.0214(13) 0.0247(12) 0.0066(10) -0.0002(11) 0.0002(12) O22 0.0305(17) 0.0243(14) 0.0227(12) -0.0069(10) 0.0082(11) -0.0014(12) N21 0.025(2) 0.0215(19) 0.0246(17) -0.0057(14) 0.0058(15) 0.0006(16) N22 0.025(2) 0.0165(15) 0.0199(14) 0.0021(12) 0.0049(13) -0.0009(13) N23 0.029(2) 0.0195(17) 0.0191(15) 0.0040(13) 0.0083(14) 0.0016(14) C21 0.022(2) 0.0137(18) 0.0212(18) 0.0031(14) 0.0047(16) 0.0001(16) C22 0.029(3) 0.023(2) 0.0186(18) -0.0020(15) 0.0084(17) -0.0020(17) C23 0.029(3) 0.021(2) 0.0218(19) -0.0035(16) 0.0053(18) -0.0041(19) C24 0.028(2) 0.0131(18) 0.0187(17) 0.0041(14) 0.0078(16) -0.0004(16) C25 0.029(3) 0.0192(19) 0.0151(17) 0.0005(15) 0.0045(16) -0.0015(17) C26 0.025(3) 0.022(2) 0.0145(17) -0.0007(15) 0.0006(16) -0.0018(17) C27 0.021(2) 0.021(2) 0.0235(17) -0.0009(15) 0.0059(16) -0.0017(16) C28 0.037(3) 0.024(2) 0.030(2) 0.0065(18) 0.0137(19) 0.001(2) C29 0.056(3) 0.032(2) 0.023(2) 0.0089(18) 0.011(2) -0.005(2) _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 S11 O12 1.442(2) . ? S11 O11 1.448(2) . ? S11 N12 1.588(3) . ? S11 C14 1.760(4) . ? S12 C19 1.725(4) . ? S12 C17 1.744(3) . ? N11 C11 1.406(4) . ? N11 H10 0.881(18) . ? N11 H11 0.887(18) . ? N12 C17 1.328(4) . ? N13 C17 1.340(4) . ? N13 C18 1.376(4) . ? N13 H17 0.884(17) . ? C11 C16 1.393(4) . ? C11 C12 1.401(5) . ? C12 C13 1.374(5) . ? C12 H12 0.95(3) . ? C13 C14 1.388(4) . ? C13 H13 0.92(3) . ? C14 C15 1.395(5) . ? C15 C16 1.365(5) . ? C15 H15 0.94(3) . ? C16 H16 0.97(3) . ? C18 C19 1.324(5) . ? C18 H18 0.92(3) . ? C19 H19 0.89(3) . ? S21 O21 1.440(2) . ? S21 O22 1.441(2) . ? S21 N22 1.600(3) . ? S21 C24 1.755(4) . ? S22 C29 1.736(4) . ? S22 C27 1.736(3) . ? N21 C21 1.401(5) . ? N21 H20 0.880(18) . ? N21 H21 0.854(18) . ? N22 C27 1.339(4) . ? N23 C27 1.333(4) . ? N23 C28 1.384(4) . ? N23 H27 0.888(18) . ? C21 C26 1.395(4) . ? C21 C22 1.396(5) . ? C22 C23 1.376(5) . ? C22 H22 1.01(3) . ? C23 C24 1.404(4) . ? C23 H23 0.94(3) . ? C24 C25 1.392(5) . ? C25 C26 1.381(5) . ? C25 H25 0.97(3) . ? C26 H26 0.96(3) . ? C28 C29 1.310(5) . ? C28 H28 0.92(3) . ? C29 H29 0.94(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 O12 S11 O11 116.16(14) . . ? O12 S11 N12 114.29(14) . . ? O11 S11 N12 105.58(14) . . ? O12 S11 C14 107.78(15) . . ? O11 S11 C14 107.50(14) . . ? N12 S11 C14 104.78(16) . . ? C19 S12 C17 90.50(18) . . ? C11 N11 H10 110(2) . . ? C11 N11 H11 110(3) . . ? H10 N11 H11 108(3) . . ? C17 N12 S11 119.8(2) . . ? C17 N13 C18 115.5(3) . . ? C17 N13 H17 120(2) . . ? C18 N13 H17 124(2) . . ? C16 C11 C12 118.4(4) . . ? C16 C11 N11 121.9(3) . . ? C12 C11 N11 119.7(3) . . ? C13 C12 C11 120.8(3) . . ? C13 C12 H12 122.7(19) . . ? C11 C12 H12 117(2) . . ? C12 C13 C14 120.0(3) . . ? C12 C13 H13 117.4(19) . . ? C14 C13 H13 122.6(19) . . ? C13 C14 C15 119.5(3) . . ? C13 C14 S11 119.1(3) . . ? C15 C14 S11 121.4(3) . . ? C16 C15 C14 120.4(3) . . ? C16 C15 H15 124(2) . . ? C14 C15 H15 116(2) . . ? C15 C16 C11 120.8(3) . . ? C15 C16 H16 121.3(19) . . ? C11 C16 H16 117.8(19) . . ? N12 C17 N13 120.4(3) . . ? N12 C17 S12 130.3(3) . . ? N13 C17 S12 109.2(2) . . ? C19 C18 N13 112.7(4) . . ? C19 C18 H18 131(2) . . ? N13 C18 H18 117(2) . . ? C18 C19 S12 112.1(3) . . ? C18 C19 H19 129(2) . . ? S12 C19 H19 119(2) . . ? O21 S21 O22 117.51(14) . . ? O21 S21 N22 105.62(14) . . ? O22 S21 N22 113.13(14) . . ? O21 S21 C24 107.53(14) . . ? O22 S21 C24 107.36(15) . . ? N22 S21 C24 104.88(15) . . ? C29 S22 C27 90.30(17) . . ? C21 N21 H20 114(2) . . ? C21 N21 H21 112(2) . . ? H20 N21 H21 112(3) . . ? C27 N22 S21 119.8(2) . . ? C27 N23 C28 114.9(3) . . ? C27 N23 H27 120(3) . . ? C28 N23 H27 125(3) . . ? C26 C21 C22 119.3(4) . . ? C26 C21 N21 122.1(3) . . ? C22 C21 N21 118.6(3) . . ? C23 C22 C21 120.4(3) . . ? C23 C22 H22 121(2) . . ? C21 C22 H22 118(2) . . ? C22 C23 C24 120.5(4) . . ? C22 C23 H23 124(2) . . ? C24 C23 H23 116(2) . . ? C25 C24 C23 119.0(3) . . ? C25 C24 S21 122.1(3) . . ? C23 C24 S21 118.9(3) . . ? C26 C25 C24 120.5(3) . . ? C26 C25 H25 119(2) . . ? C24 C25 H25 121(2) . . ? C25 C26 C21 120.4(3) . . ? C25 C26 H26 121(2) . . ? C21 C26 H26 119(2) . . ? N23 C27 N22 120.4(3) . . ? N23 C27 S22 109.8(2) . . ? N22 C27 S22 129.8(3) . . ? C29 C28 N23 113.2(3) . . ? C29 C28 H28 133(2) . . ? N23 C28 H28 114(2) . . ? C28 C29 S22 111.7(3) . . ? C28 C29 H29 133(2) . . ? S22 C29 H29 115(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O12 S11 N12 C17 -39.9(3) . . . . ? O11 S11 N12 C17 -168.8(3) . . . . ? C14 S11 N12 C17 77.8(3) . . . . ? C16 C11 C12 C13 -2.0(5) . . . . ? N11 C11 C12 C13 179.7(3) . . . . ? C11 C12 C13 C14 1.2(5) . . . . ? C12 C13 C14 C15 0.0(5) . . . . ? C12 C13 C14 S11 -179.6(2) . . . . ? O12 S11 C14 C13 173.1(2) . . . . ? O11 S11 C14 C13 -61.0(3) . . . . ? N12 S11 C14 C13 51.0(3) . . . . ? O12 S11 C14 C15 -6.4(3) . . . . ? O11 S11 C14 C15 119.5(3) . . . . ? N12 S11 C14 C15 -128.5(3) . . . . ? C13 C14 C15 C16 -0.2(5) . . . . ? S11 C14 C15 C16 179.4(2) . . . . ? C14 C15 C16 C11 -0.8(5) . . . . ? C12 C11 C16 C15 1.8(5) . . . . ? N11 C11 C16 C15 -180.0(3) . . . . ? S11 N12 C17 N13 -163.1(3) . . . . ? S11 N12 C17 S12 19.5(5) . . . . ? C18 N13 C17 N12 -178.6(3) . . . . ? C18 N13 C17 S12 -0.7(4) . . . . ? C19 S12 C17 N12 178.4(4) . . . . ? C19 S12 C17 N13 0.7(3) . . . . ? C17 N13 C18 C19 0.2(5) . . . . ? N13 C18 C19 S12 0.4(5) . . . . ? C17 S12 C19 C18 -0.6(4) . . . . ? O21 S21 N22 C27 -166.3(3) . . . . ? O22 S21 N22 C27 -36.4(3) . . . . ? C24 S21 N22 C27 80.2(3) . . . . ? C26 C21 C22 C23 -1.0(5) . . . . ? N21 C21 C22 C23 -179.6(3) . . . . ? C21 C22 C23 C24 0.4(5) . . . . ? C22 C23 C24 C25 0.0(5) . . . . ? C22 C23 C24 S21 178.9(3) . . . . ? O21 S21 C24 C25 121.5(3) . . . . ? O22 S21 C24 C25 -5.8(3) . . . . ? N22 S21 C24 C25 -126.4(3) . . . . ? O21 S21 C24 C23 -57.4(3) . . . . ? O22 S21 C24 C23 175.3(2) . . . . ? N22 S21 C24 C23 54.7(3) . . . . ? C23 C24 C25 C26 0.2(5) . . . . ? S21 C24 C25 C26 -178.7(2) . . . . ? C24 C25 C26 C21 -0.7(5) . . . . ? C22 C21 C26 C25 1.2(5) . . . . ? N21 C21 C26 C25 179.7(3) . . . . ? C28 N23 C27 N22 179.1(3) . . . . ? C28 N23 C27 S22 -1.3(4) . . . . ? S21 N22 C27 N23 -165.8(3) . . . . ? S21 N22 C27 S22 14.7(5) . . . . ? C29 S22 C27 N23 1.1(3) . . . . ? C29 S22 C27 N22 -179.3(4) . . . . ? C27 N23 C28 C29 0.9(5) . . . . ? N23 C28 C29 S22 0.0(5) . . . . ? C27 S22 C29 C28 -0.6(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N11 H10 N22 0.881(18) 2.33(2) 3.184(4) 162(3) 3_565 N11 H11 O21 0.887(18) 2.14(2) 3.001(4) 164(3) . N13 H17 N21 0.884(17) 1.978(19) 2.846(4) 167(3) . N21 H20 O11 0.880(18) 2.14(2) 3.005(4) 168(3) 2_645 N21 H21 O11 0.854(18) 2.18(2) 2.977(4) 155(3) 1_545 N23 H27 N11 0.888(18) 2.02(2) 2.899(4) 171(4) 1_545 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.434 _refine_diff_density_min -0.479 _refine_diff_density_rms 0.077 data_form_IV _database_code_depnum_ccdc_archive 'CCDC 687588' _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 8.193(2) _cell_length_b 8.538(2) _cell_length_c 15.437(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.01(3) _cell_angle_gamma 90.00 _cell_volume 1077.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.574 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.482 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9098 _exptl_absorpt_correction_T_max 0.9313 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10998 _diffrn_reflns_av_R_equivalents 0.0341 _diffrn_reflns_av_sigmaI/netI 0.0259 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 25.02 _reflns_number_total 1893 _reflns_number_gt 1771 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0450P)^2^+0.7248P] 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 1893 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0335 _refine_ls_R_factor_gt 0.0310 _refine_ls_wR_factor_ref 0.0827 _refine_ls_wR_factor_gt 0.0812 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 S11 S 0.72911(5) 0.10805(5) 0.61714(3) 0.01635(15) Uani 1 1 d . . . S12 S 0.78781(7) 0.33354(6) 0.45120(3) 0.02974(17) Uani 1 1 d . . . O11 O 0.63364(15) 0.02699(14) 0.67837(8) 0.0218(3) Uani 1 1 d . . . O12 O 0.74220(15) 0.03243(15) 0.53434(8) 0.0226(3) Uani 1 1 d . . . N11 N 1.39656(19) 0.18311(19) 0.79035(10) 0.0196(3) Uani 1 1 d . . . N12 N 0.65663(18) 0.28125(17) 0.61053(9) 0.0189(3) Uani 1 1 d . . . N13 N 0.67330(18) 0.53000(17) 0.55278(10) 0.0189(3) Uani 1 1 d . . . C11 C 1.2409(2) 0.16591(18) 0.74689(11) 0.0164(4) Uani 1 1 d . . . C12 C 1.1046(2) 0.2289(2) 0.78418(11) 0.0189(4) Uani 1 1 d . . . C13 C 0.9500(2) 0.2127(2) 0.74370(11) 0.0186(4) Uani 1 1 d . . . C14 C 0.9288(2) 0.12985(19) 0.66592(11) 0.0161(4) Uani 1 1 d . . . C15 C 1.0627(2) 0.0658(2) 0.62891(11) 0.0169(4) Uani 1 1 d . . . C16 C 1.2185(2) 0.0828(2) 0.66907(11) 0.0173(4) Uani 1 1 d . . . C17 C 0.6999(2) 0.3757(2) 0.54814(11) 0.0175(4) Uani 1 1 d . . . C18 C 0.7213(2) 0.6171(2) 0.48362(12) 0.0256(4) Uani 1 1 d . . . C19 C 0.7855(3) 0.5308(2) 0.42364(14) 0.0341(5) Uani 1 1 d . . . H10 H 1.477(3) 0.153(3) 0.7580(15) 0.029(6) Uiso 1 1 d . . . H11 H 1.411(3) 0.276(3) 0.8087(14) 0.026(6) Uiso 1 1 d . . . H12 H 1.120(3) 0.284(3) 0.8371(14) 0.026(5) Uiso 1 1 d . . . H13 H 0.858(3) 0.255(2) 0.7688(13) 0.020(5) Uiso 1 1 d . . . H15 H 1.049(2) 0.011(2) 0.5790(14) 0.020(5) Uiso 1 1 d . . . H16 H 1.307(3) 0.044(2) 0.6408(12) 0.018(5) Uiso 1 1 d . . . H17 H 0.635(3) 0.571(3) 0.6000(15) 0.031(6) Uiso 1 1 d . . . H18 H 0.705(3) 0.725(3) 0.4850(14) 0.031(6) Uiso 1 1 d . . . H19 H 0.826(3) 0.559(3) 0.3727(17) 0.042(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S11 0.0156(3) 0.0158(2) 0.0180(2) -0.00017(15) 0.00376(17) 0.00174(15) S12 0.0439(3) 0.0259(3) 0.0208(3) 0.00337(18) 0.0127(2) 0.0072(2) O11 0.0195(7) 0.0188(6) 0.0280(7) 0.0039(5) 0.0082(5) 0.0007(5) O12 0.0219(7) 0.0252(7) 0.0207(7) -0.0073(5) 0.0020(5) 0.0026(5) N11 0.0171(8) 0.0187(8) 0.0233(8) -0.0038(6) 0.0026(6) 0.0002(6) N12 0.0190(8) 0.0185(8) 0.0196(7) 0.0021(6) 0.0037(6) 0.0039(6) N13 0.0202(8) 0.0182(8) 0.0181(8) 0.0005(6) 0.0002(6) 0.0016(6) C11 0.0193(9) 0.0119(8) 0.0183(9) 0.0034(6) 0.0024(7) -0.0004(6) C12 0.0231(10) 0.0166(9) 0.0176(9) -0.0028(7) 0.0044(7) 0.0007(7) C13 0.0182(9) 0.0192(9) 0.0193(9) -0.0004(7) 0.0073(7) 0.0034(7) C14 0.0164(9) 0.0141(8) 0.0180(8) 0.0029(6) 0.0021(7) 0.0009(6) C15 0.0203(9) 0.0155(8) 0.0153(9) -0.0001(7) 0.0042(7) 0.0020(7) C16 0.0166(9) 0.0173(8) 0.0191(9) 0.0013(7) 0.0073(7) 0.0027(7) C17 0.0151(9) 0.0213(9) 0.0158(9) -0.0001(7) -0.0006(7) 0.0008(7) C18 0.0288(11) 0.0228(10) 0.0250(10) 0.0074(8) 0.0002(8) 0.0001(8) C19 0.0462(13) 0.0311(11) 0.0264(11) 0.0110(9) 0.0116(10) 0.0041(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 S11 O12 1.4427(13) . ? S11 O11 1.4448(13) . ? S11 N12 1.5941(15) . ? S11 C14 1.7625(18) . ? S12 C19 1.737(2) . ? S12 C17 1.7431(18) . ? N11 C11 1.407(2) . ? N12 C17 1.323(2) . ? N13 C17 1.338(2) . ? N13 C18 1.381(2) . ? C11 C16 1.396(2) . ? C11 C12 1.399(3) . ? C12 C13 1.379(3) . ? C13 C14 1.394(2) . ? C14 C15 1.385(3) . ? C15 C16 1.386(3) . ? C18 C19 1.321(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 O12 S11 O11 116.26(8) . . ? O12 S11 N12 114.14(8) . . ? O11 S11 N12 105.66(8) . . ? O12 S11 C14 107.55(8) . . ? O11 S11 C14 107.45(8) . . ? N12 S11 C14 105.06(8) . . ? C19 S12 C17 90.70(9) . . ? C17 N12 S11 119.62(13) . . ? C17 N13 C18 115.64(16) . . ? C16 C11 C12 119.23(16) . . ? C16 C11 N11 121.59(16) . . ? C12 C11 N11 119.14(16) . . ? C13 C12 C11 120.61(16) . . ? C12 C13 C14 119.75(16) . . ? C15 C14 C13 120.08(16) . . ? C15 C14 S11 121.38(14) . . ? C13 C14 S11 118.54(14) . . ? C14 C15 C16 120.33(17) . . ? C15 C16 C11 119.98(17) . . ? N12 C17 N13 120.53(16) . . ? N12 C17 S12 130.32(14) . . ? N13 C17 S12 109.12(13) . . ? C19 C18 N13 112.98(18) . . ? C18 C19 S12 111.56(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O12 S11 N12 C17 -39.22(16) . . . . ? O11 S11 N12 C17 -168.20(13) . . . . ? C14 S11 N12 C17 78.35(15) . . . . ? C16 C11 C12 C13 -1.6(3) . . . . ? N11 C11 C12 C13 -179.34(16) . . . . ? C11 C12 C13 C14 1.5(3) . . . . ? C12 C13 C14 C15 -0.8(3) . . . . ? C12 C13 C14 S11 178.72(13) . . . . ? O12 S11 C14 C15 -6.00(16) . . . . ? O11 S11 C14 C15 119.85(15) . . . . ? N12 S11 C14 C15 -127.96(14) . . . . ? O12 S11 C14 C13 174.47(13) . . . . ? O11 S11 C14 C13 -59.68(15) . . . . ? N12 S11 C14 C13 52.51(15) . . . . ? C13 C14 C15 C16 0.3(3) . . . . ? S11 C14 C15 C16 -179.18(13) . . . . ? C14 C15 C16 C11 -0.5(3) . . . . ? C12 C11 C16 C15 1.1(2) . . . . ? N11 C11 C16 C15 178.79(15) . . . . ? S11 N12 C17 N13 -164.09(13) . . . . ? S11 N12 C17 S12 17.9(2) . . . . ? C18 N13 C17 N12 -179.19(16) . . . . ? C18 N13 C17 S12 -0.82(19) . . . . ? C19 S12 C17 N12 178.96(18) . . . . ? C19 S12 C17 N13 0.80(14) . . . . ? C17 N13 C18 C19 0.4(3) . . . . ? N13 C18 C19 S12 0.3(2) . . . . ? C17 S12 C19 C18 -0.63(18) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N11 H10 O11 0.89(2) 2.13(3) 3.001(2) 165(2) 1_655 N11 H11 O11 0.85(2) 2.19(2) 2.989(2) 157.8(19) 2_756 N13 H17 N11 0.89(2) 1.98(2) 2.845(2) 166(2) 2_756 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.235 _refine_diff_density_min -0.479 _refine_diff_density_rms 0.056 data_form_V _database_code_depnum_ccdc_archive 'CCDC 687589' _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 10.7740(10) _cell_length_b 8.4670(10) _cell_length_c 11.3670(10) _cell_angle_alpha 90.00 _cell_angle_beta 91.650(10) _cell_angle_gamma 90.00 _cell_volume 1036.51(18) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.636 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.500 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8851 _exptl_absorpt_correction_T_max 0.9706 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7262 _diffrn_reflns_av_R_equivalents 0.0756 _diffrn_reflns_av_sigmaI/netI 0.0643 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2026 _reflns_number_gt 1655 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0515P)^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 2026 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0555 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.0959 _refine_ls_wR_factor_gt 0.0910 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 S11 S 0.48228(5) 0.11472(6) 0.26293(4) 0.01403(18) Uani 1 1 d . . . S12 S 0.34389(6) 0.34250(6) 0.06718(5) 0.02392(19) Uani 1 1 d . . . O11 O 0.49723(14) 0.03463(15) 0.37404(12) 0.0190(4) Uani 1 1 d . . . O12 O 0.40188(14) 0.04220(15) 0.17448(12) 0.0181(4) Uani 1 1 d . . . N11 N 0.98740(17) 0.1901(2) 0.07072(16) 0.0163(4) Uani 1 1 d . . . N12 N 0.44221(16) 0.29157(19) 0.29397(14) 0.0146(4) Uani 1 1 d . . . N13 N 0.38859(17) 0.54216(19) 0.22789(15) 0.0144(4) Uani 1 1 d . . . C11 C 0.8672(2) 0.1691(2) 0.11378(17) 0.0135(4) Uani 1 1 d . . . C12 C 0.8393(2) 0.2310(2) 0.22415(18) 0.0152(5) Uani 1 1 d . . . C13 C 0.7221(2) 0.2152(2) 0.26780(17) 0.0144(5) Uani 1 1 d . . . C14 C 0.63056(19) 0.1339(2) 0.20310(17) 0.0134(4) Uani 1 1 d . . . C15 C 0.6582(2) 0.0682(2) 0.09514(17) 0.0141(4) Uani 1 1 d . . . C16 C 0.7761(2) 0.0845(2) 0.05115(17) 0.0137(4) Uani 1 1 d . . . C17 C 0.39804(19) 0.3863(2) 0.20909(17) 0.0145(4) Uani 1 1 d . . . C18 C 0.3421(2) 0.6287(3) 0.13377(19) 0.0188(5) Uani 1 1 d . . . C19 C 0.3143(2) 0.5414(3) 0.0404(2) 0.0270(6) Uani 1 1 d . . . H10 H 0.989(2) 0.164(3) -0.005(2) 0.027(7) Uiso 1 1 d . . . H11 H 1.010(2) 0.283(3) 0.082(2) 0.027(7) Uiso 1 1 d . . . H12 H 0.900(2) 0.289(3) 0.2670(19) 0.017(6) Uiso 1 1 d . . . H13 H 0.704(2) 0.263(2) 0.346(2) 0.016(5) Uiso 1 1 d . . . H15 H 0.595(2) 0.013(3) 0.053(2) 0.024(6) Uiso 1 1 d . . . H16 H 0.794(2) 0.038(2) -0.0242(19) 0.012(5) Uiso 1 1 d . . . H17 H 0.4147(19) 0.581(2) 0.2943(18) 0.008(5) Uiso 1 1 d . . . H18 H 0.337(2) 0.740(3) 0.144(2) 0.028(6) Uiso 1 1 d . . . H19 H 0.290(2) 0.562(3) -0.032(2) 0.032(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S11 0.0169(3) 0.0127(3) 0.0126(3) 0.0002(2) 0.0022(2) 0.0007(2) S12 0.0347(4) 0.0194(3) 0.0171(3) -0.0012(2) -0.0086(2) 0.0037(2) O11 0.0272(9) 0.0151(7) 0.0148(7) 0.0028(6) 0.0054(6) 0.0038(6) O12 0.0170(8) 0.0185(8) 0.0188(8) -0.0044(6) 0.0015(6) -0.0034(6) N11 0.0185(11) 0.0150(9) 0.0156(10) -0.0022(8) 0.0032(8) -0.0010(8) N12 0.0172(10) 0.0136(9) 0.0130(8) 0.0007(7) 0.0013(7) 0.0019(7) N13 0.0155(10) 0.0137(9) 0.0141(9) -0.0008(8) 0.0004(7) 0.0013(7) C11 0.0173(11) 0.0092(9) 0.0141(10) 0.0036(8) 0.0006(8) 0.0029(8) C12 0.0184(12) 0.0120(10) 0.0151(10) -0.0004(9) -0.0017(9) 0.0000(8) C13 0.0201(12) 0.0117(10) 0.0115(10) -0.0012(8) -0.0003(8) 0.0013(8) C14 0.0154(12) 0.0119(10) 0.0130(10) 0.0023(8) 0.0014(8) 0.0026(8) C15 0.0173(12) 0.0114(10) 0.0136(10) 0.0009(9) -0.0009(9) 0.0014(8) C16 0.0190(12) 0.0123(10) 0.0098(10) 0.0003(8) 0.0005(8) 0.0030(8) C17 0.0120(11) 0.0172(10) 0.0145(10) -0.0013(9) 0.0031(8) 0.0001(8) C18 0.0184(13) 0.0175(11) 0.0205(11) 0.0045(10) 0.0003(9) 0.0034(9) C19 0.0330(16) 0.0262(13) 0.0214(12) 0.0033(11) -0.0052(10) 0.0049(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 S11 O11 1.4384(14) . ? S11 O12 1.4449(14) . ? S11 N12 1.6006(17) . ? S11 C14 1.762(2) . ? S12 C19 1.739(2) . ? S12 C17 1.740(2) . ? N11 C11 1.409(3) . ? N11 H10 0.89(3) . ? N11 H11 0.84(3) . ? N12 C17 1.332(3) . ? N13 C17 1.341(3) . ? N13 C18 1.379(3) . ? N13 H17 0.86(2) . ? C11 C16 1.394(3) . ? C11 C12 1.400(3) . ? C12 C13 1.376(3) . ? C12 H12 0.94(2) . ? C13 C14 1.395(3) . ? C13 H13 1.00(2) . ? C14 C15 1.387(3) . ? C15 C16 1.385(3) . ? C15 H15 0.95(2) . ? C16 H16 0.97(2) . ? C18 C19 1.321(3) . ? C18 H18 0.95(3) . ? C19 H19 0.88(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 O11 S11 O12 117.41(9) . . ? O11 S11 N12 105.76(9) . . ? O12 S11 N12 113.01(9) . . ? O11 S11 C14 107.60(9) . . ? O12 S11 C14 107.62(9) . . ? N12 S11 C14 104.61(9) . . ? C19 S12 C17 90.61(11) . . ? C11 N11 H10 110.6(17) . . ? C11 N11 H11 109.6(17) . . ? H10 N11 H11 112(2) . . ? C17 N12 S11 119.79(14) . . ? C17 N13 C18 115.27(18) . . ? C17 N13 H17 119.4(13) . . ? C18 N13 H17 125.3(13) . . ? C16 C11 C12 118.9(2) . . ? C16 C11 N11 121.88(19) . . ? C12 C11 N11 119.18(19) . . ? C13 C12 C11 120.6(2) . . ? C13 C12 H12 119.7(14) . . ? C11 C12 H12 119.6(14) . . ? C12 C13 C14 119.99(19) . . ? C12 C13 H13 118.8(13) . . ? C14 C13 H13 121.2(13) . . ? C15 C14 C13 119.9(2) . . ? C15 C14 S11 121.63(16) . . ? C13 C14 S11 118.50(15) . . ? C16 C15 C14 120.1(2) . . ? C16 C15 H15 121.6(14) . . ? C14 C15 H15 118.3(14) . . ? C15 C16 C11 120.43(19) . . ? C15 C16 H16 119.1(13) . . ? C11 C16 H16 120.5(13) . . ? N12 C17 N13 120.29(17) . . ? N12 C17 S12 130.27(15) . . ? N13 C17 S12 109.43(15) . . ? C19 C18 N13 113.2(2) . . ? C19 C18 H18 129.5(14) . . ? N13 C18 H18 117.3(14) . . ? C18 C19 S12 111.44(18) . . ? C18 C19 H19 134.4(16) . . ? S12 C19 H19 114.0(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O11 S11 N12 C17 -166.91(16) . . . . ? O12 S11 N12 C17 -37.16(19) . . . . ? C14 S11 N12 C17 79.62(18) . . . . ? C16 C11 C12 C13 -3.1(3) . . . . ? N11 C11 C12 C13 178.76(17) . . . . ? C11 C12 C13 C14 1.4(3) . . . . ? C12 C13 C14 C15 0.4(3) . . . . ? C12 C13 C14 S11 179.36(15) . . . . ? O11 S11 C14 C15 120.15(17) . . . . ? O12 S11 C14 C15 -7.25(19) . . . . ? N12 S11 C14 C15 -127.69(16) . . . . ? O11 S11 C14 C13 -58.79(16) . . . . ? O12 S11 C14 C13 173.80(14) . . . . ? N12 S11 C14 C13 53.37(17) . . . . ? C13 C14 C15 C16 -0.6(3) . . . . ? S11 C14 C15 C16 -179.49(14) . . . . ? C14 C15 C16 C11 -1.1(3) . . . . ? C12 C11 C16 C15 2.9(3) . . . . ? N11 C11 C16 C15 -178.98(17) . . . . ? S11 N12 C17 N13 -166.05(16) . . . . ? S11 N12 C17 S12 15.0(3) . . . . ? C18 N13 C17 N12 179.78(19) . . . . ? C18 N13 C17 S12 -1.0(2) . . . . ? C19 S12 C17 N12 -179.7(2) . . . . ? C19 S12 C17 N13 1.20(17) . . . . ? C17 N13 C18 C19 0.2(3) . . . . ? N13 C18 C19 S12 0.8(3) . . . . ? C17 S12 C19 C18 -1.1(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N11 H10 N12 0.89(3) 2.36(3) 3.173(2) 153(2) 4_665 N11 H11 O11 0.84(3) 2.19(3) 2.988(2) 160(2) 2_655 N13 H17 N11 0.86(2) 2.06(2) 2.902(3) 166.3(19) 2_655 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.430 _refine_diff_density_min -0.591 _refine_diff_density_rms 0.111