#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/91/2009117.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2009117 loop_ _publ_author_name 'Hughes, David S.' 'Hursthouse, Michael B.' 'Threlfall, Terry' 'Tavener, Stewart' _publ_section_title ; A new polymorph of sulfathiazole ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1831 _journal_page_last 1833 _journal_paper_doi 10.1107/S0108270199010112 _journal_volume 55 _journal_year 1999 _chemical_formula_sum 'C9 H9 N3 O2 S2' _chemical_formula_weight 255.31 _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _audit_creation_method 'WinGX routine CIF_UPDATE' _cell_angle_alpha 90 _cell_angle_beta 91.21(3) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 10.399(2) _cell_length_b 15.132(3) _cell_length_c 14.280(3) _cell_measurement_reflns_used 2749 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 25.00 _cell_measurement_theta_min 3.05 _cell_volume 2246.6(8) _computing_cell_refinement 'DENZO and COLLECT' _computing_data_collection 'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)' _computing_data_reduction 'DENZO and COLLECT' _computing_molecular_graphics 'CAMERON (Watkin & Pearce, 1993)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_measurement_device 'Nonius Kappa CCD area detector' _diffrn_measurement_method '\f + \w scans to fill the Ewald sphere' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.098 _diffrn_reflns_av_sigmaI/netI 0.064 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 28369 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_min 3.05 _diffrn_standards_decay_% none _exptl_absorpt_coefficient_mu 0.462 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_correction_T_min 0.868 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'using SORTAV (Blessing, 1995)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.51 _exptl_crystal_description block _exptl_crystal_F_000 1056 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.256 _refine_diff_density_min -0.373 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.858 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 319 _refine_ls_number_reflns 3936 _refine_ls_number_restraints 4 _refine_ls_restrained_S_all 0.882 _refine_ls_R_factor_gt 0.046 _refine_ls_shift/su_max -0.038 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.1P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.079 _reflns_number_gt 2749 _reflns_number_total 3936 _reflns_threshold_expression I>2\s(I) _cod_data_source_file fg1566.cif _cod_data_source_block s92 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.1P)^2^] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.1P)^2^] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2009117 _cod_database_fobs_code 2009117 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' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol S11 .17581(7) .40001(6) -.14444(6) .0275(2) Uani d . 1 . . S S12 .33345(8) .37399(7) .05805(6) .0404(3) Uani d . 1 . . S O11 .1372(2) .35111(16) -.22744(16) .0351(6) Uani d . 1 . . O O12 .11201(19) .37652(15) -.05911(16) .0317(6) Uani d . 1 . . O N11 .0924(3) .7823(2) -.1961(3) .0519(9) Uani d D 1 . . N H10 .129(3) .816(2) -.240(2) .042(10) Uiso d D 1 . . H H11 .036(4) .815(3) -.159(3) .092(17) Uiso d D 1 . . H N12 .3282(2) .38965(19) -.13676(18) .0288(7) Uani d . 1 . . N N13 .5198(2) .38573(18) -.05178(19) .0287(6) Uani d . 1 . . N H17 .5646 .3912 -.1014 .055(13) Uiso calc R 1 . . H C11 .1098(3) .6944(2) -.1880(2) .0315(8) Uani d . 1 . . C C12 .2078(3) .6499(2) -.2361(2) .0327(8) Uani d . 1 . . C H12 .2601 .6814 -.2762 .042(10) Uiso calc R 1 . . H C13 .2270(3) .5608(2) -.2246(2) .0301(8) Uani d . 1 . . C H13 .2918 .5325 -.2571 .022(8) Uiso calc R 1 . . H C14 .1496(3) .5122(2) -.1643(2) .0253(7) Uani d . 1 . . C C15 .0505(3) .5555(2) -.1180(2) .0280(8) Uani d . 1 . . C H15 -.0027 .5238 -.0787 .037(10) Uiso calc R 1 . . H C16 .0312(3) .6450(2) -.1301(2) .0305(8) Uani d . 1 . . C H16 -.0353 .6727 -.0991 .030(9) Uiso calc R 1 . . H C17 .3906(3) .3844(2) -.0549(2) .0273(7) Uani d . 1 . . C C18 .5758(3) .3777(3) .0362(2) .0366(9) Uani d . 1 . . C H18 .6642 .3766 .0475 .047(11) Uiso calc R 1 . . H C19 .4893(3) .3716(3) .1032(3) .0458(10) Uani d . 1 . . C H19 .5099 .3667 .1667 .070(14) Uiso calc R 1 . . H S21 .17103(7) .05317(6) .17760(6) .0286(2) Uani d . 1 . . S S22 .32040(8) .10341(8) -.01384(6) .0442(3) Uani d . 1 . . S O22 .0954(2) .09562(15) .10411(16) .0337(6) Uani d . 1 . . O O21 .1264(2) .06537(17) .27229(16) .0376(6) Uani d . 1 . . O N21 .1688(3) -.3323(2) .1077(2) .0326(7) Uani d D 1 . . N H20 .100(2) -.356(2) .077(2) .038(10) Uiso d D 1 . . H H21 .192(3) -.366(2) .1568(18) .034(10) Uiso d D 1 . . H N22 .3178(2) .08555(18) .18073(19) .0298(7) Uani d . 1 . . N N23 .5033(3) .1230(2) .1031(2) .0347(7) Uani d . 1 . . N H27 .5474 .1267 .1546 .033(10) Uiso calc R 1 . . H C21 .1670(3) -.2432(2) .1252(2) .0273(8) Uani d . 1 . . C C26 .0845(3) -.1869(2) .0750(2) .0344(8) Uani d . 1 . . C H26 .0267 -.2105 .0312 .035(9) Uiso calc R 1 . . H C25 .0873(3) -.0971(2) .0894(2) .0329(8) Uani d . 1 . . C H25 .0314 -.0608 .0552 .050(11) Uiso calc R 1 . . H C24 .1724(3) -.0601(2) .1542(2) .0255(7) Uani d . 1 . . C C23 .2561(3) -.1149(2) .2054(2) .0293(8) Uani d . 1 . . C H23 .3134 -.0906 .2492 .039(10) Uiso calc R 1 . . H C22 .2536(3) -.2050(2) .1910(2) .0297(8) Uani d . 1 . . C H22 .3098 -.2411 .2251 .040(10) Uiso calc R 1 . . H C27 .3776(3) .1022(2) .1020(2) .0282(8) Uani d . 1 . . C C28 .5577(4) .1382(3) .0176(3) .0454(10) Uani d . 1 . . C H28 .6437 .1528 .0099 .103(19) Uiso calc R 1 . . H C29 .4728(4) .1297(3) -.0526(3) .0552(12) Uani d . 1 . . C H29 .4926 .1370 -.1153 .066(13) Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S11 .0228(4) .0311(5) .0284(5) .0004(3) .0002(3) -.0026(4) S12 .0271(5) .0705(7) .0238(5) -.0056(4) .0024(3) .0010(5) O11 .0335(13) .0350(15) .0365(14) .0007(10) -.0070(10) -.0115(11) O12 .0248(12) .0347(14) .0357(14) -.0012(10) .0055(10) .0025(11) N11 .064(2) .036(2) .057(2) .0119(17) .0298(18) .0190(18) N12 .0213(14) .0406(18) .0244(15) .0041(11) .0018(11) -.0002(13) N13 .0213(14) .0364(17) .0285(16) .0014(11) .0026(12) .0010(13) C11 .0324(18) .036(2) .0260(19) .0039(15) .0008(14) .0056(16) C12 .0335(19) .037(2) .0271(19) -.0010(15) .0060(14) .0099(16) C13 .0255(17) .040(2) .0250(18) .0049(15) .0019(13) -.0032(16) C14 .0230(16) .030(2) .0229(17) .0001(13) -.0011(13) -.0032(15) C15 .0275(17) .032(2) .0244(18) -.0044(14) .0029(13) -.0018(15) C16 .0231(17) .037(2) .0316(19) .0016(14) .0046(13) -.0012(17) C17 .0248(17) .031(2) .0266(18) -.0023(13) .0029(13) -.0026(15) C18 .0240(18) .053(3) .033(2) -.0016(15) -.0052(15) -.0009(18) C19 .033(2) .077(3) .028(2) -.0043(19) -.0055(15) -.004(2) S21 .0275(5) .0324(5) .0260(5) .0017(3) .0019(3) -.0017(4) S22 .0350(5) .0720(8) .0256(5) -.0069(4) .0002(4) .0033(5) O22 .0340(13) .0333(14) .0335(14) .0054(10) -.0024(10) .0023(11) O21 .0385(14) .0441(16) .0307(14) .0016(11) .0113(10) -.0037(11) N21 .0333(17) .0300(19) .0342(18) -.0030(13) -.0041(13) .0027(15) N22 .0289(15) .0339(17) .0266(16) -.0035(12) .0008(11) -.0016(13) N23 .0299(16) .045(2) .0290(17) -.0055(13) -.0037(12) .0015(14) C21 .0249(17) .032(2) .0247(18) -.0019(13) .0029(13) .0027(15) C26 .0304(18) .035(2) .038(2) -.0039(15) -.0117(15) .0020(17) C25 .0342(19) .033(2) .031(2) .0004(15) -.0099(15) .0049(17) C24 .0234(16) .0266(19) .0266(18) -.0007(13) .0007(13) .0034(15) C23 .0279(17) .036(2) .0238(18) -.0016(14) -.0028(13) .0006(16) C22 .0230(16) .039(2) .0273(18) .0011(14) -.0037(13) .0052(16) C27 .0311(18) .0249(19) .0285(19) .0007(13) -.0036(14) .0006(15) C28 .039(2) .064(3) .034(2) -.0075(18) .0062(17) .013(2) C29 .039(2) .099(4) .028(2) -.006(2) .0075(17) .013(2) 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 0 '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 0.006 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle O12 S11 O11 116.16(14) O12 S11 N12 113.06(14) O11 S11 N12 105.32(14) O12 S11 C14 107.72(14) O11 S11 C14 108.97(15) N12 S11 C14 105.02(15) C19 S12 C17 90.67(17) C17 N12 S11 122.2(2) C17 N13 C18 115.6(3) N11 C11 C16 120.2(3) N11 C11 C12 121.8(3) C16 C11 C12 118.1(3) C13 C12 C11 121.0(3) C12 C13 C14 120.4(3) C13 C14 C15 118.9(3) C13 C14 S11 121.5(2) C15 C14 S11 119.6(2) C16 C15 C14 120.5(3) C15 C16 C11 121.1(3) N12 C17 N13 119.9(3) N12 C17 S12 130.7(2) N13 C17 S12 109.4(2) C19 C18 N13 112.4(3) C18 C19 S12 111.9(3) O22 S21 O21 116.09(14) O22 S21 N22 112.76(14) O21 S21 N22 104.95(14) O22 S21 C24 107.67(15) O21 S21 C24 107.88(15) N22 S21 C24 107.07(14) C29 S22 C27 90.54(17) C27 N22 S21 120.0(2) C27 N23 C28 116.6(3) N21 C21 C26 121.1(3) N21 C21 C22 120.9(3) C26 C21 C22 117.9(3) C25 C26 C21 121.0(3) C26 C25 C24 120.6(3) C25 C24 C23 119.5(3) C25 C24 S21 121.1(3) C23 C24 S21 119.3(2) C22 C23 C24 119.9(3) C23 C22 C21 120.9(3) N22 C27 N23 120.7(3) N22 C27 S22 130.6(2) N23 C27 S22 108.7(2) C29 C28 N23 112.0(3) C28 C29 S22 112.3(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S11 O12 . 1.444(2) ? S11 O11 . 1.447(2) ? S11 N12 . 1.594(3) ? S11 C14 . 1.741(3) ? S12 C19 . 1.732(4) ? S12 C17 . 1.738(3) ? N11 C11 . 1.347(5) ? N12 C17 . 1.327(4) ? N13 C17 . 1.343(4) ? N13 C18 . 1.379(4) ? C11 C16 . 1.392(5) ? C11 C12 . 1.413(5) ? C12 C13 . 1.372(5) ? C13 C14 . 1.400(4) ? C14 C15 . 1.399(4) ? C15 C16 . 1.378(5) ? C18 C19 . 1.330(5) ? S21 O22 . 1.448(2) ? S21 O21 . 1.451(2) ? S21 N22 . 1.603(3) ? S21 C24 . 1.747(3) ? S22 C29 . 1.735(4) ? S22 C27 . 1.747(3) ? N21 C21 . 1.372(4) ? N22 C27 . 1.320(4) ? N23 C27 . 1.344(4) ? N23 C28 . 1.376(4) ? C21 C26 . 1.397(5) ? C21 C22 . 1.411(4) ? C26 C25 . 1.374(5) ? C25 C24 . 1.386(5) ? C24 C23 . 1.397(4) ? C23 C22 . 1.379(5) ? C28 C29 . 1.328(5) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N11 H10 N12 2_554 0.90(2) 2.14(2) 3.016(4) 165(3) N11 H10 O11 2_554 0.90(2) 2.54(3) 3.211(4) 132(3) N11 H11 O22 3_565 0.93(2) 2.10(2) 3.010(4) 167(5) N13 H17 O21 4_665 0.86 2.04 2.865(4) 161 N21 H20 O12 3 0.90(2) 2.24(2) 3.061(4) 152(3) N21 H21 O21 2_545 0.90(2) 2.37(3) 3.116(4) 141(3) N21 H21 N22 2_545 0.90(2) 2.44(2) 3.267(4) 154(3) N23 H27 O11 4_666 0.86 1.94 2.794(4) 173 loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 5148 2 PubChem 139056890