#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/24/2202485.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_2202485 loop_ _publ_author_name 'Sharon, Ashoke' 'Srivastava, Tumul' 'Katti, B. S.' 'Maulik, Prakas R.' _publ_section_title ; 2-(4-Chlorophenyl)-3-cyclohexylthiazolidin-4-one ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1239 _journal_page_last o1240 _journal_paper_doi 10.1107/S1600536803016477 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C15 H18 Cl N O S' _chemical_formula_moiety 'C15 H18 Cl N O S' _chemical_formula_sum 'C15 H18 Cl N O S' _chemical_formula_weight 295.81 _chemical_melting_point 386 _chemical_name_common Thiazolidin-4-one _chemical_name_systematic ; 2-(4-Chlorophenyl)-3-cyclohexylthiazolidin-4-one ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 97.330(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 17.6000(10) _cell_length_b 9.7750(10) _cell_length_c 17.0890(10) _cell_measurement_reflns_used 40 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 12.455 _cell_measurement_theta_min 5.137 _cell_volume 2916.0(4) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens, 1996)' _computing_data_reduction XSCANS _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Bruker, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method \q-2\q _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 0.0229 _diffrn_reflns_av_sigmaI/netI 0.0490 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 3556 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 26.00 _diffrn_reflns_theta_min 2.33 _diffrn_standards_decay_% none _diffrn_standards_interval_count 97 _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.397 _exptl_absorpt_correction_type none _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.348 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 1248 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.175 _refine_diff_density_max 0.206 _refine_diff_density_min -0.209 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 172 _refine_ls_number_reflns 2866 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.016 _refine_ls_R_factor_all 0.0944 _refine_ls_R_factor_gt 0.0478 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0439P)^2^+1.3546P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1011 _refine_ls_wR_factor_ref 0.1190 _reflns_number_gt 1731 _reflns_number_total 2866 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ci6252.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 2202485 _cod_database_fobs_code 2202485 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -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 S1 0.16274(4) 0.17650(9) 0.16189(5) 0.0718(3) Uani d . 1 . . S C2 0.25050(13) 0.0747(3) 0.17898(14) 0.0494(6) Uani d . 1 . . C H2 0.2387 -0.0131 0.2023 0.059 Uiso calc R 1 . . H N3 0.27374(11) 0.0497(2) 0.10103(11) 0.0494(5) Uani d . 1 . . N C4 0.22676(15) 0.0926(3) 0.03705(17) 0.0580(7) Uani d . 1 . . C C5 0.15605(16) 0.1634(3) 0.05776(18) 0.0741(9) Uani d . 1 . . C H5A 0.1108 0.1116 0.0375 0.089 Uiso calc R 1 . . H H5B 0.1520 0.2539 0.0343 0.089 Uiso calc R 1 . . H C6 0.30938(13) 0.1485(2) 0.23539(14) 0.0441(6) Uani d . 1 . . C C7 0.34244(14) 0.2689(3) 0.21354(14) 0.0493(6) Uani d . 1 . . C H7 0.3277 0.3052 0.1636 0.059 Uiso calc R 1 . . H C8 0.39709(14) 0.3356(3) 0.26506(15) 0.0544(7) Uani d . 1 . . C H8 0.4196 0.4160 0.2501 0.065 Uiso calc R 1 . . H C9 0.41754(15) 0.2808(3) 0.33901(15) 0.0559(7) Uani d . 1 . . C C10 0.38527(16) 0.1633(3) 0.36243(15) 0.0617(8) Uani d . 1 . . C H10 0.3996 0.1283 0.4128 0.074 Uiso calc R 1 . . H C11 0.33070(14) 0.0965(3) 0.31017(15) 0.0538(7) Uani d . 1 . . C H11 0.3084 0.0163 0.3256 0.065 Uiso calc R 1 . . H C12 0.33388(14) -0.0514(3) 0.09054(15) 0.0522(7) Uani d . 1 . . C H12 0.3367 -0.0545 0.0337 0.063 Uiso calc R 1 . . H C13 0.41300(15) -0.0137(3) 0.1280(2) 0.0753(9) Uani d . 1 . . C H13A 0.4133 -0.0056 0.1846 0.090 Uiso calc R 1 . . H H13B 0.4270 0.0745 0.1080 0.090 Uiso calc R 1 . . H C14 0.47162(16) -0.1202(3) 0.1107(2) 0.0775(10) Uani d . 1 . . C H14A 0.4767 -0.1184 0.0548 0.093 Uiso calc R 1 . . H H14B 0.5210 -0.0973 0.1396 0.093 Uiso calc R 1 . . H C15 0.44928(19) -0.2616(3) 0.1332(2) 0.0840(10) Uani d . 1 . . C H15A 0.4857 -0.3269 0.1169 0.101 Uiso calc R 1 . . H H15B 0.4517 -0.2670 0.1901 0.101 Uiso calc R 1 . . H C16 0.37058(18) -0.2992(3) 0.0964(2) 0.0823(10) Uani d . 1 . . C H16A 0.3568 -0.3872 0.1168 0.099 Uiso calc R 1 . . H H16B 0.3703 -0.3082 0.0398 0.099 Uiso calc R 1 . . H C17 0.31159(16) -0.1934(3) 0.11276(18) 0.0668(8) Uani d . 1 . . C H17A 0.2625 -0.2167 0.0832 0.080 Uiso calc R 1 . . H H17B 0.3058 -0.1953 0.1684 0.080 Uiso calc R 1 . . H O18 0.23859(12) 0.0749(2) -0.03095(12) 0.0776(6) Uani d . 1 . . O Cl19 0.48668(5) 0.36355(10) 0.40489(5) 0.0857(3) Uani d . 1 . . Cl 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 0.0430(4) 0.0896(6) 0.0808(5) 0.0129(4) 0.0002(3) -0.0059(5) C2 0.0405(13) 0.0515(16) 0.0565(15) 0.0016(12) 0.0073(11) 0.0039(13) N3 0.0439(11) 0.0568(13) 0.0463(12) 0.0012(11) 0.0015(9) -0.0004(10) C4 0.0549(17) 0.0598(18) 0.0556(18) -0.0145(14) -0.0069(14) 0.0023(14) C5 0.0517(17) 0.084(2) 0.082(2) 0.0014(17) -0.0110(15) 0.0130(18) C6 0.0395(13) 0.0483(16) 0.0451(14) 0.0090(12) 0.0069(10) 0.0009(12) C7 0.0498(15) 0.0530(16) 0.0441(14) 0.0053(13) 0.0023(11) 0.0040(13) C8 0.0463(15) 0.0547(16) 0.0620(17) 0.0044(13) 0.0059(13) -0.0004(14) C9 0.0461(15) 0.066(2) 0.0532(17) 0.0068(14) -0.0016(12) -0.0103(14) C10 0.0615(17) 0.077(2) 0.0438(15) 0.0167(17) -0.0028(13) 0.0042(15) C11 0.0530(16) 0.0578(17) 0.0517(15) 0.0088(14) 0.0111(13) 0.0047(13) C12 0.0485(15) 0.0537(16) 0.0547(15) -0.0035(14) 0.0079(12) -0.0071(13) C13 0.0467(16) 0.063(2) 0.116(3) -0.0045(15) 0.0127(16) -0.0204(18) C14 0.0474(17) 0.070(2) 0.115(3) -0.0027(16) 0.0103(17) -0.0280(19) C15 0.065(2) 0.076(2) 0.109(3) 0.0181(19) 0.0023(18) -0.007(2) C16 0.071(2) 0.0542(19) 0.124(3) -0.0016(17) 0.019(2) -0.0078(19) C17 0.0544(17) 0.0560(18) 0.089(2) -0.0083(15) 0.0069(15) 0.0014(16) O18 0.0921(15) 0.0864(16) 0.0500(12) -0.0093(12) -0.0077(10) 0.0022(11) Cl19 0.0716(5) 0.0996(7) 0.0783(5) 0.0010(5) -0.0200(4) -0.0226(5) 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' Cl Cl 0.1484 0.1585 '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 C5 S1 C2 93.88(13) N3 C2 C6 114.42(19) N3 C2 S1 105.91(16) C6 C2 S1 109.88(17) N3 C2 H2 108.8 C6 C2 H2 108.8 S1 C2 H2 108.8 C4 N3 C2 118.1(2) C4 N3 C12 118.9(2) C2 N3 C12 120.72(19) O18 C4 N3 124.5(3) O18 C4 C5 122.4(3) N3 C4 C5 113.0(2) C4 C5 S1 108.55(19) C4 C5 H5A 110.0 S1 C5 H5A 110.0 C4 C5 H5B 110.0 S1 C5 H5B 110.0 H5A C5 H5B 108.4 C11 C6 C7 119.2(2) C11 C6 C2 120.0(2) C7 C6 C2 120.8(2) C8 C7 C6 120.8(2) C8 C7 H7 119.6 C6 C7 H7 119.6 C9 C8 C7 118.7(3) C9 C8 H8 120.7 C7 C8 H8 120.7 C10 C9 C8 121.8(2) C10 C9 Cl19 118.9(2) C8 C9 Cl19 119.3(2) C9 C10 C11 119.2(2) C9 C10 H10 120.4 C11 C10 H10 120.4 C6 C11 C10 120.4(3) C6 C11 H11 119.8 C10 C11 H11 119.8 N3 C12 C13 115.1(2) N3 C12 C17 111.9(2) C13 C12 C17 112.1(2) N3 C12 H12 105.6 C13 C12 H12 105.6 C17 C12 H12 105.6 C12 C13 C14 111.3(2) C12 C13 H13A 109.4 C14 C13 H13A 109.4 C12 C13 H13B 109.4 C14 C13 H13B 109.4 H13A C13 H13B 108.0 C15 C14 C13 112.0(3) C15 C14 H14A 109.2 C13 C14 H14A 109.2 C15 C14 H14B 109.2 C13 C14 H14B 109.2 H14A C14 H14B 107.9 C16 C15 C14 112.2(3) C16 C15 H15A 109.2 C14 C15 H15A 109.2 C16 C15 H15B 109.2 C14 C15 H15B 109.2 H15A C15 H15B 107.9 C15 C16 C17 112.0(3) C15 C16 H16A 109.2 C17 C16 H16A 109.2 C15 C16 H16B 109.2 C17 C16 H16B 109.2 H16A C16 H16B 107.9 C12 C17 C16 112.1(2) C12 C17 H17A 109.2 C16 C17 H17A 109.2 C12 C17 H17B 109.2 C16 C17 H17B 109.2 H17A C17 H17B 107.9 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 C5 . 1.773(3) ? S1 C2 . 1.829(2) ? C2 N3 . 1.463(3) ? C2 C6 . 1.506(3) ? C2 H2 . 0.98 ? N3 C4 . 1.351(3) ? N3 C12 . 1.475(3) ? C4 O18 . 1.219(3) ? C4 C5 . 1.505(4) ? C5 H5A . 0.97 ? C5 H5B . 0.97 ? C6 C11 . 1.382(3) ? C6 C7 . 1.385(3) ? C7 C8 . 1.382(3) ? C7 H7 . 0.93 ? C8 C9 . 1.378(4) ? C8 H8 . 0.93 ? C9 C10 . 1.364(4) ? C9 Cl19 . 1.747(3) ? C10 C11 . 1.388(4) ? C10 H10 . 0.93 ? C11 H11 . 0.93 ? C12 C13 . 1.502(4) ? C12 C17 . 1.504(4) ? C12 H12 . 0.98 ? C13 C14 . 1.521(4) ? C13 H13A . 0.97 ? C13 H13B . 0.97 ? C14 C15 . 1.500(4) ? C14 H14A . 0.97 ? C14 H14B . 0.97 ? C15 C16 . 1.492(4) ? C15 H15A . 0.97 ? C15 H15B . 0.97 ? C16 C17 . 1.517(4) ? C16 H16A . 0.97 ? C16 H16B . 0.97 ? C17 H17A . 0.97 ? C17 H17B . 0.97 ? 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 C5 H5B O18 7 0.97 2.56 3.226(4) 126 C7 H7 O18 7 0.93 2.68 3.601(3) 169 C12 H12 O18 . 0.98 2.31 2.785(3) 109 C13 H13A Cg1 . 0.97 2.99 3.717(3) 133 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 C5 S1 C2 N3 6.17(19) C5 S1 C2 C6 130.24(19) C6 C2 N3 C4 -126.3(2) S1 C2 N3 C4 -5.1(3) C6 C2 N3 C12 70.7(3) S1 C2 N3 C12 -168.12(17) C2 N3 C4 O18 -178.0(3) C12 N3 C4 O18 -14.7(4) C2 N3 C4 C5 0.8(3) C12 N3 C4 C5 164.1(2) O18 C4 C5 S1 -177.0(2) N3 C4 C5 S1 4.1(3) C2 S1 C5 C4 -5.9(2) N3 C2 C6 C11 -129.3(2) S1 C2 C6 C11 111.8(2) N3 C2 C6 C7 51.1(3) S1 C2 C6 C7 -67.9(3) C11 C6 C7 C8 1.1(4) C2 C6 C7 C8 -179.3(2) C6 C7 C8 C9 -0.6(4) C7 C8 C9 C10 -0.1(4) C7 C8 C9 Cl19 179.87(19) C8 C9 C10 C11 0.5(4) Cl19 C9 C10 C11 -179.54(19) C7 C6 C11 C10 -0.8(4) C2 C6 C11 C10 179.6(2) C9 C10 C11 C6 0.0(4) C4 N3 C12 C13 129.3(3) C2 N3 C12 C13 -67.8(3) C4 N3 C12 C17 -101.2(3) C2 N3 C12 C17 61.7(3) N3 C12 C13 C14 -177.2(2) C17 C12 C13 C14 53.4(3) C12 C13 C14 C15 -53.6(4) C13 C14 C15 C16 53.8(4) C14 C15 C16 C17 -53.1(4) N3 C12 C17 C16 175.8(2) C13 C12 C17 C16 -53.2(3) C15 C16 C17 C12 52.8(4) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 2521512 2 PubChem 741657