#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/22/2202244.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_2202244 loop_ _publ_author_name 'M. Sukeri M. Yusof' 'Bohari M. Yamin' _publ_section_title ; 3-(3-Benzoylthioureido)propionic acid ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o828 _journal_page_last o829 _journal_paper_doi 10.1107/S1600536803010389 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C11 H12 N2 O3 S' _chemical_formula_moiety 'C11 H12 N2 O3 S' _chemical_formula_sum 'C11 H12 N2 O3 S' _chemical_formula_weight 252.29 _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 94.685(3) _cell_angle_beta 91.341(3) _cell_angle_gamma 96.759(3) _cell_formula_units_Z 2 _cell_length_a 4.5868(9) _cell_length_b 10.582(2) _cell_length_c 13.080(3) _cell_measurement_reflns_used 2840 _cell_measurement_temperature 273(2) _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 1.6 _cell_volume 628.0(2) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material 'SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1997)' _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 273(2) _diffrn_detector_area_resol_mean 83.66 _diffrn_measured_fraction_theta_full 0.985 _diffrn_measured_fraction_theta_max 0.985 _diffrn_measurement_device_type 'Bruker SMART APEX CCD area-detector' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0166 _diffrn_reflns_av_sigmaI/netI 0.0224 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 7220 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_min 1.6 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.256 _exptl_absorpt_correction_T_max 0.9554 _exptl_absorpt_correction_T_min 0.8659 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_method 'not measured' _exptl_crystal_description slab _exptl_crystal_F_000 264 _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.267 _refine_diff_density_min -0.193 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 155 _refine_ls_number_reflns 2818 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.027 _refine_ls_R_factor_all 0.0533 _refine_ls_R_factor_gt 0.0452 _refine_ls_shift/su_max <0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0612P)^2^+0.1496P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1164 _refine_ls_wR_factor_ref 0.1227 _reflns_number_gt 2363 _reflns_number_total 2818 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ww6087.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' 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 'Triclinic' changed to 'triclinic' 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 ; _cod_database_code 2202244 _cod_database_fobs_code 2202244 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 S1 0.36044(11) 0.13532(4) 0.10273(4) 0.06111(18) Uani d . 1 . . S O1 0.9292(4) 0.39011(12) -0.09335(10) 0.0719(4) Uani d . 1 . . O O2 0.4306(4) 0.50196(17) 0.37633(10) 0.0815(5) Uani d . 1 . . O O3 0.7400(5) 0.3907(2) 0.44855(12) 0.1109(8) Uani d . 1 . . O H3 0.6841 0.4268 0.5011 0.166 Uiso calc R 1 . . H N1 0.7182(3) 0.20049(13) -0.04471(10) 0.0472(3) Uani d . 1 . . N H1A 0.6920 0.1198 -0.0624 0.057 Uiso calc R 1 . . H N2 0.6622(3) 0.35995(13) 0.08252(11) 0.0524(4) Uani d . 1 . . N H2A 0.7783 0.4088 0.0480 0.063 Uiso calc R 1 . . H C1 1.1061(4) 0.09273(17) -0.19906(14) 0.0542(4) Uani d . 1 . . C H1B 1.1175 0.0551 -0.1375 0.065 Uiso calc R 1 . . H C2 1.2122(5) 0.0361(2) -0.28751(17) 0.0703(5) Uani d . 1 . . C H2B 1.2983 -0.0389 -0.2850 0.084 Uiso calc R 1 . . H C3 1.1911(6) 0.0898(2) -0.37851(17) 0.0779(6) Uani d . 1 . . C H3A 1.2609 0.0506 -0.4378 0.094 Uiso calc R 1 . . H C4 1.0673(6) 0.2013(2) -0.38280(16) 0.0812(7) Uani d . 1 . . C H4A 1.0525 0.2373 -0.4450 0.097 Uiso calc R 1 . . H C5 0.9654(5) 0.2597(2) -0.29529(15) 0.0685(5) Uani d . 1 . . C H5A 0.8842 0.3359 -0.2981 0.082 Uiso calc R 1 . . H C6 0.9834(4) 0.20516(16) -0.20277(12) 0.0485(4) Uani d . 1 . . C C7 0.8787(4) 0.27413(16) -0.10954(12) 0.0494(4) Uani d . 1 . . C C8 0.5922(3) 0.24015(15) 0.04628(12) 0.0455(4) Uani d . 1 . . C C9 0.5530(4) 0.41369(18) 0.17796(13) 0.0554(4) Uani d . 1 . . C H9A 0.3463 0.3830 0.1824 0.067 Uiso calc R 1 . . H H9B 0.5715 0.5060 0.1782 0.067 Uiso calc R 1 . . H C10 0.7189(5) 0.3781(2) 0.26981(14) 0.0679(5) Uani d . 1 . . C H10B 0.7032 0.2857 0.2683 0.081 Uiso calc R 1 . . H H10C 0.9250 0.4097 0.2651 0.081 Uiso calc R 1 . . H C11 0.6123(4) 0.4292(2) 0.36940(14) 0.0603(5) Uani d . 1 . . C 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 S1 0.0664(3) 0.0559(3) 0.0578(3) -0.0070(2) 0.0181(2) 0.0009(2) O1 0.1110(12) 0.0454(7) 0.0559(8) -0.0062(7) 0.0267(7) -0.0013(6) O2 0.0981(11) 0.1067(12) 0.0465(7) 0.0474(10) 0.0087(7) -0.0042(7) O3 0.1393(16) 0.1595(19) 0.0484(8) 0.0909(15) -0.0011(9) -0.0077(10) N1 0.0566(8) 0.0419(7) 0.0411(7) -0.0002(6) 0.0058(6) -0.0010(5) N2 0.0636(9) 0.0486(8) 0.0436(7) 0.0011(6) 0.0135(6) -0.0009(6) C1 0.0588(10) 0.0540(10) 0.0491(9) 0.0027(8) 0.0061(7) 0.0047(7) C2 0.0789(14) 0.0658(12) 0.0673(13) 0.0172(10) 0.0125(10) -0.0035(10) C3 0.0939(16) 0.0880(16) 0.0509(11) 0.0158(13) 0.0158(10) -0.0107(10) C4 0.1131(19) 0.0905(16) 0.0419(10) 0.0180(14) 0.0094(11) 0.0070(10) C5 0.0985(16) 0.0637(12) 0.0454(10) 0.0162(11) 0.0065(9) 0.0064(8) C6 0.0550(9) 0.0481(9) 0.0400(8) -0.0021(7) 0.0042(7) 0.0000(6) C7 0.0587(10) 0.0469(9) 0.0408(8) 0.0000(7) 0.0043(7) 0.0017(7) C8 0.0460(8) 0.0495(9) 0.0404(8) 0.0047(7) 0.0005(6) 0.0024(6) C9 0.0630(11) 0.0552(10) 0.0480(9) 0.0098(8) 0.0117(8) -0.0027(7) C10 0.0679(12) 0.0863(14) 0.0499(10) 0.0228(10) 0.0039(9) -0.0121(9) C11 0.0603(11) 0.0736(12) 0.0465(10) 0.0126(9) 0.0053(8) -0.0052(8) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C11 O3 H3 109.5 ? C7 N1 C8 127.95(14) yes C7 N1 H1A 116.0 ? C8 N1 H1A 116.0 ? C8 N2 C9 123.27(15) yes C8 N2 H2A 118.4 ? C9 N2 H2A 118.4 ? C6 C1 C2 119.61(18) ? C6 C1 H1B 120.2 ? C2 C1 H1B 120.2 ? C3 C2 C1 120.4(2) ? C3 C2 H2B 119.8 ? C1 C2 H2B 119.8 ? C2 C3 C4 120.23(19) ? C2 C3 H3A 119.9 ? C4 C3 H3A 119.9 ? C3 C4 C5 120.0(2) ? C3 C4 H4A 120.0 ? C5 C4 H4A 120.0 ? C4 C5 C6 120.1(2) ? C4 C5 H5A 119.9 ? C6 C5 H5A 119.9 ? C1 C6 C5 119.62(17) ? C1 C6 C7 122.26(15) ? C5 C6 C7 118.08(16) ? O1 C7 N1 122.27(15) ? O1 C7 C6 121.61(15) ? N1 C7 C6 116.11(14) ? N2 C8 N1 117.26(14) yes N2 C8 S1 123.77(13) yes N1 C8 S1 118.97(12) yes N2 C9 C10 111.62(15) ? N2 C9 H9A 109.3 ? C10 C9 H9A 109.3 ? N2 C9 H9B 109.3 ? C10 C9 H9B 109.3 ? H9A C9 H9B 108.0 ? C11 C10 C9 113.63(16) ? C11 C10 H10B 108.8 ? C9 C10 H10B 108.8 ? C11 C10 H10C 108.8 ? C9 C10 H10C 108.8 ? H10B C10 H10C 107.7 ? O2 C11 O3 122.94(17) ? O2 C11 C10 123.40(18) ? O3 C11 C10 113.64(17) ? 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 S1 C8 . 1.6728(17) yes O1 C7 . 1.222(2) yes O2 C11 . 1.199(2) yes O3 C11 . 1.296(2) yes O3 H3 . 0.8200 ? N1 C7 . 1.368(2) ? N1 C8 . 1.391(2) ? N1 H1A . 0.8600 ? N2 C8 . 1.317(2) yes N2 C9 . 1.454(2) yes N2 H2A . 0.8600 ? C1 C6 . 1.378(3) ? C1 C2 . 1.384(3) ? C1 H1B . 0.9300 ? C2 C3 . 1.366(3) ? C2 H2B . 0.9300 ? C3 C4 . 1.373(3) ? C3 H3A . 0.9300 ? C4 C5 . 1.374(3) ? C4 H4A . 0.9300 ? C5 C6 . 1.387(3) ? C5 H5A . 0.9300 ? C6 C7 . 1.488(2) ? C9 C10 . 1.504(3) ? C9 H9A . 0.9700 ? C9 H9B . 0.9700 ? C10 C11 . 1.485(3) ? C10 H10B . 0.9700 ? C10 H10C . 0.9700 ? 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 _geom_hbond_publ_flag N2 H2A O1 1_555 0.86 1.99 2.656(2) 133 yes N2 H2A O1 2_765 0.86 2.40 3.047(2) 132 yes N1 H1A S1 2_655 0.86 2.69 3.5466(16) 175 yes O3 H3 O2 2_666 0.82 1.83 2.649(2) 176 yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 3346225 2 PubChem 4133430