#------------------------------------------------------------------------------ #$Date: 2025-08-19 12:52:15 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301804 $ #$URL: svn://www.crystallography.net/cod/cif/2/21/41/2214181.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_2214181 loop_ _publ_author_name 'Shoukat, Noreen' 'Rauf, M. Khawar' 'Bolte, Michael' 'Badshah, Amin' _publ_section_title ; 1-(3-Chlorophenyl)-3-pivaloylthiourea ; _journal_coeditor_code EZ2082 _journal_issue 7 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3207 _journal_page_last o3207 _journal_paper_doi 10.1107/S1600536807028280 _journal_volume 63 _journal_year 2007 _chemical_formula_iupac 'C12 H15 Cl N2 O S' _chemical_formula_moiety 'C12 H15 Cl N2 O S' _chemical_formula_sum 'C12 H15 Cl N2 O S' _chemical_formula_weight 270.77 _chemical_name_common 1-Pivaloyl-3-(3-chlorophenyl)thiourea _chemical_name_systematic ; 1-(3-Chlorophenyl)-3-pivaloylthiourea ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.1269(2) _cell_length_b 10.2848(4) _cell_length_c 21.1360(9) _cell_measurement_reflns_used 34614 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 29.8 _cell_measurement_theta_min 3.5 _cell_volume 1331.86(9) _computing_cell_refinement X-AREA _computing_data_collection 'X-AREA (Stoe & Cie, 2001)' _computing_data_reduction X-AREA _computing_molecular_graphics 'XP in SHELXTL-Plus (Sheldrick, 1991)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Stoe IPDSII two-circle' _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 0.052 _diffrn_reflns_av_sigmaI/netI 0.018 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_number 35409 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.6 _diffrn_reflns_theta_min 3.5 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.429 _exptl_absorpt_correction_T_max 0.824 _exptl_absorpt_correction_T_min 0.817 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(MULABS; Spek, 2003; Blessing, 1995)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.350 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 568 _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.49 _exptl_crystal_size_min 0.47 _refine_diff_density_max 0.224 _refine_diff_density_min -0.177 _refine_ls_abs_structure_details 'Flack, (1983), 1573 Friedel pairs' _refine_ls_abs_structure_Flack -0.01(4) _refine_ls_extinction_coef 0.028(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.04 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 191 _refine_ls_number_reflns 3742 _refine_ls_number_restraints 30 _refine_ls_restrained_S_all 1.05 _refine_ls_R_factor_all 0.023 _refine_ls_R_factor_gt 0.023 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0361P)^2^+0.1922P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.062 _refine_ls_wR_factor_ref 0.062 _reflns_number_gt 3700 _reflns_number_total 3742 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ez2082.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' 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 'Orthorhombic' changed to 'orthorhombic' 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 2214181 _cod_database_fobs_code 2214181 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' loop_ _atom_site_type_symbol _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 Cl Cl1 0.56583(5) 0.11877(3) 0.622329(14) 0.03278(8) Uani d . 1 . . S S1 0.71872(4) 0.66862(3) 0.541901(12) 0.02455(7) Uani d . 1 . . O O1 0.53343(17) 0.53031(9) 0.34538(4) 0.0357(2) Uani d . 1 . . N N1 0.51185(16) 0.50045(9) 0.46671(4) 0.02377(17) Uani d . 1 . . H H1 0.471(3) 0.4776(19) 0.4264(9) 0.052(5) Uiso d . 1 . . N N2 0.72061(15) 0.65585(8) 0.41596(4) 0.02134(16) Uani d . 1 . . H H2 0.821(3) 0.7168(17) 0.4228(8) 0.040(4) Uiso d . 1 . . C C1 0.64372(15) 0.60313(9) 0.47266(5) 0.01990(17) Uani d . 1 . . C C2 0.66320(17) 0.61904(11) 0.35498(5) 0.02307(19) Uani d . 1 A . C C3 0.76111(18) 0.69697(11) 0.30021(5) 0.0255(2) Uani d D 1 . . C C11 0.41745(17) 0.43202(9) 0.51909(5) 0.02176(18) Uani d . 1 . . C C12 0.52851(16) 0.32519(10) 0.54368(5) 0.02213(18) Uani d . 1 . . H H12 0.6688 0.3019 0.5283 0.027 Uiso calc R 1 . . C C13 0.42847(18) 0.25339(10) 0.59147(5) 0.02302(19) Uani d . 1 . . C C14 0.2224(2) 0.28558(11) 0.61466(5) 0.0260(2) Uani d . 1 . . H H14 0.1563 0.2352 0.6471 0.031 Uiso calc R 1 . . C C15 0.11545(18) 0.39324(12) 0.58923(5) 0.0283(2) Uani d . 1 . . H H15 -0.0247 0.4166 0.6047 0.034 Uiso calc R 1 . . C C16 0.21162(18) 0.46708(10) 0.54130(5) 0.02590(19) Uani d . 1 . . H H16 0.1377 0.5402 0.5241 0.031 Uiso calc R 1 . . C C31 0.6919(19) 0.8377(6) 0.3090(4) 0.075(3) Uani d PD 0.501(14) A 1 H H31A 0.7498 0.8706 0.3492 0.112 Uiso calc PR 0.501(14) A 1 H H31B 0.5322 0.8431 0.3095 0.112 Uiso calc PR 0.501(14) A 1 H H31C 0.7491 0.8903 0.2741 0.112 Uiso calc PR 0.501(14) A 1 C C32 0.6826(14) 0.6375(10) 0.2402(3) 0.072(3) Uani d PD 0.501(14) A 1 H H32A 0.7430 0.6855 0.2041 0.108 Uiso calc PR 0.501(14) A 1 H H32B 0.5229 0.6411 0.2387 0.108 Uiso calc PR 0.501(14) A 1 H H32C 0.7303 0.5466 0.2381 0.108 Uiso calc PR 0.501(14) A 1 C C33 1.0128(9) 0.6913(7) 0.3023(3) 0.0448(12) Uani d PD 0.501(14) A 1 H H33A 1.0646 0.7296 0.3420 0.067 Uiso calc PR 0.501(14) A 1 H H33B 1.0729 0.7401 0.2665 0.067 Uiso calc PR 0.501(14) A 1 H H33C 1.0606 0.6005 0.2998 0.067 Uiso calc PR 0.501(14) A 1 C C31' 0.6110(11) 0.8150(7) 0.2875(3) 0.0556(14) Uani d PD 0.499(14) A 2 H H31D 0.4607 0.7849 0.2814 0.083 Uiso calc PR 0.499(14) A 2 H H31E 0.6605 0.8604 0.2493 0.083 Uiso calc PR 0.499(14) A 2 H H31F 0.6168 0.8746 0.3236 0.083 Uiso calc PR 0.499(14) A 2 C C32' 0.7525(16) 0.6115(6) 0.2407(3) 0.058(2) Uani d PD 0.499(14) A 2 H H32D 0.6026 0.5814 0.2338 0.087 Uiso calc PR 0.499(14) A 2 H H32E 0.8488 0.5363 0.2462 0.087 Uiso calc PR 0.499(14) A 2 H H32F 0.8007 0.6622 0.2040 0.087 Uiso calc PR 0.499(14) A 2 C C33' 0.9919(10) 0.7433(11) 0.3097(3) 0.0562(19) Uani d PD 0.499(14) A 2 H H33D 1.0396 0.7918 0.2722 0.084 Uiso calc PR 0.499(14) A 2 H H33E 1.0880 0.6682 0.3161 0.084 Uiso calc PR 0.499(14) A 2 H H33F 0.9985 0.7999 0.3469 0.084 Uiso calc PR 0.499(14) A 2 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 Cl1 0.04062(15) 0.02760(12) 0.03014(13) 0.00457(11) -0.00164(11) 0.00577(10) S1 0.02621(11) 0.02688(12) 0.02055(11) -0.00204(9) -0.00021(9) -0.00280(9) O1 0.0454(5) 0.0378(5) 0.0238(4) -0.0202(4) -0.0028(4) 0.0016(3) N1 0.0308(4) 0.0221(4) 0.0184(4) -0.0057(3) 0.0028(3) -0.0004(3) N2 0.0240(4) 0.0209(3) 0.0191(4) -0.0036(3) 0.0014(3) 0.0001(3) C1 0.0200(4) 0.0185(4) 0.0212(4) 0.0025(3) 0.0025(3) 0.0009(3) C2 0.0266(4) 0.0229(4) 0.0197(4) -0.0017(4) 0.0002(3) 0.0014(4) C3 0.0312(5) 0.0255(4) 0.0198(4) -0.0044(4) 0.0005(4) 0.0033(4) C11 0.0247(4) 0.0215(4) 0.0190(4) -0.0034(4) 0.0031(4) -0.0006(3) C12 0.0220(4) 0.0238(4) 0.0207(4) -0.0019(3) 0.0014(3) -0.0013(4) C13 0.0274(5) 0.0214(4) 0.0203(4) -0.0014(4) -0.0018(4) 0.0002(3) C14 0.0296(5) 0.0278(5) 0.0205(4) -0.0051(4) 0.0051(4) 0.0003(4) C15 0.0261(5) 0.0324(5) 0.0264(5) 0.0012(4) 0.0074(4) -0.0012(4) C16 0.0276(4) 0.0254(4) 0.0247(5) 0.0029(4) 0.0025(4) 0.0006(4) C31 0.118(6) 0.039(2) 0.068(4) 0.031(3) 0.045(4) 0.032(2) C32 0.077(4) 0.120(6) 0.019(2) -0.063(4) -0.013(2) 0.018(3) C33 0.0357(15) 0.060(3) 0.0384(19) -0.0093(19) 0.0065(13) 0.016(2) C31' 0.067(3) 0.052(3) 0.048(3) 0.025(2) 0.018(2) 0.027(2) C32' 0.106(6) 0.0388(18) 0.029(2) -0.036(3) 0.022(3) -0.0107(15) C33' 0.043(2) 0.092(5) 0.034(2) -0.034(3) -0.0109(18) 0.030(3) 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' Cl Cl 0.1484 0.1585 '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 C1 N1 C11 124.02(9) C1 N1 H1 117.0(12) C11 N1 H1 118.8(13) C2 N2 C1 127.23(9) C2 N2 H2 121.2(11) C1 N2 H2 111.5(11) N1 C1 N2 115.47(9) N1 C1 S1 124.48(8) N2 C1 S1 120.05(7) O1 C2 N2 121.35(9) O1 C2 C3 121.22(9) N2 C2 C3 117.39(9) C32 C3 C31 114.0(4) C32 C3 C2 107.6(3) C33' C3 C2 115.7(2) C31 C3 C2 107.3(2) C32 C3 C32' 19.1(5) C33' C3 C32' 108.8(4) C2 C3 C32' 107.8(3) C32 C3 C33 109.4(4) C31 C3 C33 108.1(4) C2 C3 C33 110.5(3) C33' C3 C31' 109.5(4) C2 C3 C31' 108.0(2) C32' C3 C31' 106.6(3) C16 C11 C12 121.37(9) C16 C11 N1 119.89(9) C12 C11 N1 118.57(9) C11 C12 C13 118.27(9) C11 C12 H12 120.9 C13 C12 H12 120.9 C12 C13 C14 121.83(10) C12 C13 Cl1 118.61(8) C14 C13 Cl1 119.56(8) C13 C14 C15 118.60(10) C13 C14 H14 120.7 C15 C14 H14 120.7 C14 C15 C16 120.87(10) C14 C15 H15 119.6 C16 C15 H15 119.6 C11 C16 C15 119.05(10) C11 C16 H16 120.5 C15 C16 H16 120.5 C3 C31 H31A 109.5 C3 C31 H31B 109.5 H31A C31 H31B 109.5 C3 C31 H31C 109.5 H31A C31 H31C 109.5 H31B C31 H31C 109.5 C3 C32 H32A 109.5 C3 C32 H32B 109.5 H32A C32 H32B 109.5 C3 C32 H32C 109.5 H32A C32 H32C 109.5 H32B C32 H32C 109.5 C3 C33 H33A 109.5 C3 C33 H33B 109.5 H33A C33 H33B 109.5 C3 C33 H33C 109.5 H33A C33 H33C 109.5 H33B C33 H33C 109.5 C3 C31' H31D 109.5 C3 C31' H31E 109.5 H31D C31' H31E 109.5 C3 C31' H31F 109.5 H31D C31' H31F 109.5 H31E C31' H31F 109.5 C3 C32' H32D 109.5 C3 C32' H32E 109.5 H32D C32' H32E 109.5 C3 C32' H32F 109.5 H32D C32' H32F 109.5 H32E C32' H32F 109.5 C3 C33' H33D 109.5 C3 C33' H33E 109.5 H33D C33' H33E 109.5 C3 C33' H33F 109.5 H33D C33' H33F 109.5 H33E C33' H33F 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C13 1.7466(11) ? S1 C1 1.6753(10) y O1 C2 1.2272(13) y N1 C1 1.3356(13) y N1 C11 1.4337(13) y N1 H1 0.918(19) ? N2 C2 1.3887(13) y N2 C1 1.3972(12) y N2 H2 0.889(18) ? C2 C3 1.5304(14) ? C3 C32 1.489(6) ? C3 C33' 1.506(5) ? C3 C31 1.520(5) ? C3 C32' 1.536(5) ? C3 C33 1.544(5) ? C3 C31' 1.547(5) ? C11 C16 1.3931(14) ? C11 C12 1.3930(14) ? C12 C13 1.3932(14) ? C12 H12 0.9500 ? C13 C14 1.3940(16) ? C14 C15 1.3945(16) ? C14 H14 0.9500 ? C15 C16 1.3965(15) ? C15 H15 0.9500 ? C16 H16 0.9500 ? C31 H31A 0.9800 ? C31 H31B 0.9800 ? C31 H31C 0.9800 ? C32 H32A 0.9800 ? C32 H32B 0.9800 ? C32 H32C 0.9800 ? C33 H33A 0.9800 ? C33 H33B 0.9800 ? C33 H33C 0.9800 ? C31' H31D 0.9800 ? C31' H31E 0.9800 ? C31' H31F 0.9800 ? C32' H32D 0.9800 ? C32' H32E 0.9800 ? C32' H32F 0.9800 ? C33' H33D 0.9800 ? C33' H33E 0.9800 ? C33' H33F 0.9800 ? 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 N1 H1 O1 . 0.918(19) 1.836(19) 2.5863(12) 137.2(18) N2 H2 S1 4_566 0.889(18) 2.808(18) 3.6560(9) 159.8(14) 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_publ_flag C11 N1 C1 N2 179.50(9) ? C11 N1 C1 S1 -0.31(15) ? C2 N2 C1 N1 4.83(15) y C2 N2 C1 S1 -175.35(8) ? C1 N2 C2 O1 -0.89(17) y C1 N2 C2 C3 176.75(9) ? O1 C2 C3 C32 -4.2(5) ? N2 C2 C3 C32 178.2(5) ? O1 C2 C3 C33' -146.3(5) ? N2 C2 C3 C33' 36.1(5) ? O1 C2 C3 C31 118.8(6) ? N2 C2 C3 C31 -58.8(6) ? O1 C2 C3 C32' -24.3(4) ? N2 C2 C3 C32' 158.1(4) ? O1 C2 C3 C33 -123.5(3) ? N2 C2 C3 C33 58.8(3) ? O1 C2 C3 C31' 90.7(4) ? N2 C2 C3 C31' -87.0(4) ? C1 N1 C11 C16 92.59(13) ? C1 N1 C11 C12 -92.01(13) ? C16 C11 C12 C13 -0.02(15) ? N1 C11 C12 C13 -175.36(9) ? C11 C12 C13 C14 0.19(15) ? C11 C12 C13 Cl1 179.68(7) ? C12 C13 C14 C15 -0.34(16) ? Cl1 C13 C14 C15 -179.83(9) ? C13 C14 C15 C16 0.33(17) ? C12 C11 C16 C15 0.02(16) ? N1 C11 C16 C15 175.29(10) ? C14 C15 C16 C11 -0.18(17) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 4927582