#------------------------------------------------------------------------------ #$Date: 2025-08-19 15:49:58 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301806 $ #$URL: svn://www.crystallography.net/cod/cif/2/23/91/2239104.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_2239104 loop_ _publ_author_name 'Yamin, Bohari M.' 'Sapari, Suhaila' 'Hasbullah, Siti Aishah' _publ_section_title ; 2,4-Dichloro-N-[ethyl(2-hydroxyethyl)carbamothioyl]benzamide ; _journal_coeditor_code RN2121 _journal_issue 1 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o33 _journal_paper_doi 10.1107/S1600536813032881 _journal_volume 70 _journal_year 2014 _chemical_formula_iupac 'C12 H14 Cl2 N2 O2 S' _chemical_formula_moiety 'C12 H14 Cl2 N2 O2 S' _chemical_formula_sum 'C12 H14 Cl2 N2 O2 S' _chemical_formula_weight 321.21 _chemical_name_systematic ; 2,4-Dichloro-N-[ethyl(2-hydroxyethyl)carbamothioyl]benzamide ; _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' _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 96.441(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.9712(4) _cell_length_b 10.6989(6) _cell_length_c 19.3288(10) _cell_measurement_reflns_used 18947 _cell_measurement_temperature 300(2) _cell_measurement_theta_max 26.5 _cell_measurement_theta_min 2.8 _cell_volume 1432.52(14) _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_collection 'SMART (Bruker,2009)' _computing_data_reduction 'SAINT (Bruker, 2009)' _computing_molecular_graphics ; SHELXTL (Sheldrick, 2008) ; _computing_publication_material ; SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010) ; _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _diffrn_ambient_temperature 300(2) _diffrn_detector_area_resol_mean 83.66 _diffrn_measured_fraction_theta_full 0.99 _diffrn_measured_fraction_theta_max 0.99 _diffrn_measurement_device_type ; Bruker SMART APEX CCD area-detector ; _diffrn_measurement_method '\w scans' _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 0.0358 _diffrn_reflns_av_sigmaI/netI 0.0175 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 30240 _diffrn_reflns_theta_full 26.5 _diffrn_reflns_theta_max 26.5 _diffrn_reflns_theta_min 2.8 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.597 _exptl_absorpt_correction_T_max 0.900 _exptl_absorpt_correction_T_min 0.754 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2009)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.489 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 664 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.44 _refine_diff_density_min -0.36 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.156 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 176 _refine_ls_number_reflns 2967 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.156 _refine_ls_R_factor_all 0.0473 _refine_ls_R_factor_gt 0.0400 _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^)+(0.0666P)^2^+0.6739P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1123 _refine_ls_wR_factor_ref 0.1256 _reflns_number_gt 2619 _reflns_number_total 2967 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL bmy320_0m in P2(1)/n CELL 0.71073 6.9712 10.6989 19.3288 90.000 96.441 90.000 ZERR 4.00 0.0004 0.0006 0.0010 0.000 0.002 0.000 LATT 1 SYMM -x+1/2, y+1/2, -z+1/2 SFAC C H N O S Cl UNIT 48 56 8 8 4 8 L.S. 20 ACTA OMIT -3 53 BOND $H FMAP 2 1 60 DFIX 0.82 0.01 o2 h2a PLAN 10 CONF HTAB SIZE 0.18 0.40 0.50 TEMP 26.95 WGHT 0.066600 0.673900 FVAR 0.16369 CL1 6 0.892405 0.713216 0.931514 11.00000 0.06909 0.03330 = 0.06791 -0.00298 0.02615 -0.00793 CL2 6 0.701106 1.086517 1.093518 11.00000 0.03998 0.05795 = 0.03789 -0.00790 0.01140 -0.00324 S1 5 0.753504 0.908351 0.641818 11.00000 0.04861 0.04807 = 0.03791 -0.00425 -0.00422 -0.01191 O1 4 0.729522 0.799973 0.787109 11.00000 0.13412 0.07455 = 0.04519 -0.01043 0.01105 -0.06986 O2 4 1.085541 1.201975 0.810049 11.00000 0.05196 0.03573 = 0.04586 -0.00527 0.00170 0.00003 N1 3 0.908322 0.974671 0.770301 11.00000 0.04237 0.03784 = 0.03083 -0.00742 0.00831 -0.01542 AFIX 43 H1A 2 0.974182 1.031568 0.793718 11.00000 -1.20000 AFIX 0 N2 3 1.076613 1.033517 0.680751 11.00000 0.03709 0.03569 = 0.02833 -0.00089 0.00529 -0.00334 C1 1 0.816318 0.865880 0.938676 11.00000 0.02633 0.03459 = 0.04462 -0.00202 0.01009 -0.00939 C2 1 0.790431 0.909022 1.004259 11.00000 0.02478 0.04143 = 0.03656 0.00435 0.00594 -0.00711 AFIX 43 H2B 2 0.808985 0.856440 1.042742 11.00000 -1.20000 AFIX 0 C3 1 0.736374 1.032000 1.011416 11.00000 0.02163 0.04542 = 0.03287 -0.00208 0.00615 -0.00392 C4 1 0.709725 1.112814 0.955522 11.00000 0.03103 0.03986 = 0.04509 0.00157 0.00904 0.00163 AFIX 43 H4A 2 0.674355 1.195577 0.961552 11.00000 -1.20000 AFIX 0 C5 1 0.736919 1.067652 0.890399 11.00000 0.03214 0.04620 = 0.03897 0.00784 0.00647 -0.00383 AFIX 43 H5A 2 0.719754 1.121140 0.852280 11.00000 -1.20000 AFIX 0 C6 1 0.789540 0.943665 0.880445 11.00000 0.02747 0.04285 = 0.03493 -0.00149 0.00719 -0.01201 C7 1 0.803635 0.896383 0.808094 11.00000 0.05162 0.04503 = 0.03780 -0.00439 0.00773 -0.02140 C8 1 0.921523 0.973724 0.698762 11.00000 0.03827 0.02680 = 0.03163 -0.00348 0.00465 0.00000 C9 1 1.098250 1.059266 0.607413 11.00000 0.04785 0.04894 = 0.03055 0.00623 0.00704 -0.00124 AFIX 23 H9A 2 1.165140 1.138224 0.604316 11.00000 -1.20000 H9B 2 0.971183 1.067688 0.581707 11.00000 -1.20000 AFIX 0 C10 1 1.207332 0.959218 0.574209 11.00000 0.05765 0.08733 = 0.03977 -0.00853 0.01229 0.01173 AFIX 33 H10A 2 1.217134 0.980826 0.526529 11.00000 -1.50000 H10B 2 1.140360 0.881101 0.576092 11.00000 -1.50000 H10C 2 1.334385 0.951630 0.598735 11.00000 -1.50000 AFIX 0 C11 1 1.241188 1.072874 0.730575 11.00000 0.03617 0.05083 = 0.03617 -0.00017 0.00636 -0.00793 AFIX 23 H11A 2 1.357611 1.070044 0.707446 11.00000 -1.20000 H11B 2 1.256566 1.013388 0.768666 11.00000 -1.20000 AFIX 0 C12 1 1.221423 1.202579 0.760323 11.00000 0.06443 0.04609 = 0.04639 -0.00237 0.00554 -0.02388 AFIX 23 H12A 2 1.345855 1.230617 0.782354 11.00000 -1.20000 H12B 2 1.179188 1.260381 0.723038 11.00000 -1.20000 AFIX 0 H2A 2 1.000075 1.253090 0.800440 11.00000 0.08071 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM bmy320_0m in P2(1)/n REM R1 = 0.0400 for 2619 Fo > 4sig(Fo) and 0.0473 for all 2967 data REM 176 parameters refined using 1 restraints END WGHT 0.0666 0.6739 REM Highest difference peak 0.441, deepest hole -0.360, 1-sigma level 0.096 Q1 1 0.6359 1.1477 0.8223 11.00000 0.05 0.44 Q2 1 0.6376 0.8663 0.7803 11.00000 0.05 0.35 Q3 1 1.4368 1.2608 0.8390 11.00000 0.05 0.30 Q4 1 1.0454 1.2280 0.8129 11.00000 0.05 0.30 Q5 1 0.5335 1.1839 0.8583 11.00000 0.05 0.28 Q6 1 1.0096 0.7773 0.6234 11.00000 0.05 0.28 Q7 1 1.3819 1.1871 0.8093 11.00000 0.05 0.26 Q8 1 0.5009 1.2281 0.9006 11.00000 0.05 0.26 Q9 1 1.0152 0.8520 0.5620 11.00000 0.05 0.26 Q10 1 1.1263 0.7479 0.6011 11.00000 0.05 0.26 ; _cod_data_source_file rn2121sup1.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2239104 _cod_database_fobs_code 2239104 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_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_symmetry_multiplicity Cl Cl1 0.89241(10) 0.71322(6) 0.93151(4) 0.0554(2) Uani d . 1 1 Cl Cl2 0.70111(8) 1.08652(6) 1.09352(3) 0.04474(18) Uani d . 1 1 S S1 0.75350(9) 0.90835(6) 0.64182(3) 0.04555(19) Uani d . 1 1 O O1 0.7295(4) 0.8000(2) 0.78711(10) 0.0845(9) Uani d . 1 1 O O2 1.0855(3) 1.20198(15) 0.81005(9) 0.0448(4) Uani d D 1 1 N N1 0.9083(3) 0.97467(17) 0.77030(9) 0.0367(4) Uani d . 1 1 H H1A 0.9742 1.0316 0.7937 0.044 Uiso calc R 1 1 N N2 1.0766(3) 1.03352(17) 0.68075(9) 0.0336(4) Uani d . 1 1 C C1 0.8163(3) 0.8659(2) 0.93868(12) 0.0347(5) Uani d . 1 1 C C2 0.7904(3) 0.9090(2) 1.00426(11) 0.0341(5) Uani d . 1 1 H H2B 0.8090 0.8564 1.0427 0.041 Uiso calc R 1 1 C C3 0.7364(3) 1.0320(2) 1.01142(11) 0.0331(4) Uani d . 1 1 C C4 0.7097(3) 1.1128(2) 0.95552(12) 0.0383(5) Uani d . 1 1 H H4A 0.6744 1.1956 0.9616 0.046 Uiso calc R 1 1 C C5 0.7369(3) 1.0677(2) 0.89040(12) 0.0389(5) Uani d . 1 1 H H5A 0.7198 1.1211 0.8523 0.047 Uiso calc R 1 1 C C6 0.7895(3) 0.9437(2) 0.88045(11) 0.0348(5) Uani d . 1 1 C C7 0.8036(4) 0.8964(2) 0.80809(12) 0.0446(6) Uani d . 1 1 C C8 0.9215(3) 0.97372(19) 0.69876(11) 0.0322(4) Uani d . 1 1 C C9 1.0983(4) 1.0593(2) 0.60741(11) 0.0422(5) Uani d . 1 1 H H9A 1.1651 1.1382 0.6043 0.051 Uiso calc R 1 1 H H9B 0.9712 1.0677 0.5817 0.051 Uiso calc R 1 1 C C10 1.2073(4) 0.9592(3) 0.57421(14) 0.0611(8) Uani d . 1 1 H H10A 1.2171 0.9808 0.5265 0.092 Uiso calc R 1 1 H H10B 1.1404 0.8811 0.5761 0.092 Uiso calc R 1 1 H H10C 1.3344 0.9516 0.5987 0.092 Uiso calc R 1 1 C C11 1.2412(3) 1.0729(2) 0.73058(12) 0.0409(5) Uani d . 1 1 H H11A 1.3576 1.0700 0.7074 0.049 Uiso calc R 1 1 H H11B 1.2566 1.0134 0.7687 0.049 Uiso calc R 1 1 C C12 1.2214(4) 1.2026(2) 0.76032(14) 0.0524(6) Uani d . 1 1 H H12A 1.3459 1.2306 0.7824 0.063 Uiso calc R 1 1 H H12B 1.1792 1.2604 0.7230 0.063 Uiso calc R 1 1 H H2A 1.000(4) 1.253(3) 0.8004(19) 0.081(12) Uiso d D 1 1 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 0.0691(4) 0.0333(3) 0.0679(4) -0.0079(3) 0.0262(3) -0.0030(3) Cl2 0.0400(3) 0.0580(4) 0.0379(3) -0.0032(2) 0.0114(2) -0.0079(2) S1 0.0486(4) 0.0481(4) 0.0379(3) -0.0119(3) -0.0042(3) -0.0043(2) O1 0.134(2) 0.0746(15) 0.0452(11) -0.0699(15) 0.0110(12) -0.0104(10) O2 0.0520(10) 0.0357(9) 0.0459(9) 0.0000(7) 0.0017(8) -0.0053(7) N1 0.0424(10) 0.0378(10) 0.0308(9) -0.0154(8) 0.0083(7) -0.0074(7) N2 0.0371(9) 0.0357(9) 0.0283(9) -0.0033(7) 0.0053(7) -0.0009(7) C1 0.0263(9) 0.0346(11) 0.0446(12) -0.0094(8) 0.0101(8) -0.0020(9) C2 0.0248(9) 0.0414(12) 0.0366(11) -0.0071(8) 0.0059(8) 0.0043(9) C3 0.0216(9) 0.0454(12) 0.0329(10) -0.0039(8) 0.0061(7) -0.0021(9) C4 0.0310(10) 0.0399(12) 0.0451(12) 0.0016(9) 0.0090(9) 0.0016(9) C5 0.0321(11) 0.0462(13) 0.0390(12) -0.0038(9) 0.0065(9) 0.0078(9) C6 0.0275(9) 0.0429(12) 0.0349(11) -0.0120(8) 0.0072(8) -0.0015(9) C7 0.0516(13) 0.0450(13) 0.0378(12) -0.0214(11) 0.0077(10) -0.0044(10) C8 0.0383(11) 0.0268(10) 0.0316(10) 0.0000(8) 0.0047(8) -0.0035(8) C9 0.0478(13) 0.0489(13) 0.0306(11) -0.0012(10) 0.0070(9) 0.0062(9) C10 0.0576(16) 0.087(2) 0.0398(13) 0.0117(15) 0.0123(12) -0.0085(14) C11 0.0362(11) 0.0508(13) 0.0362(11) -0.0079(10) 0.0064(9) -0.0002(10) C12 0.0644(16) 0.0461(14) 0.0464(14) -0.0239(12) 0.0055(12) -0.0024(11) 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 C12 O2 H2A 112(3) C7 N1 C8 128.33(18) C7 N1 H1A 115.8 C8 N1 H1A 115.8 C8 N2 C9 121.02(18) C8 N2 C11 124.05(17) C9 N2 C11 114.86(17) C2 C1 C6 121.5(2) C2 C1 Cl1 117.57(17) C6 C1 Cl1 120.91(17) C1 C2 C3 118.5(2) C1 C2 H2B 120.8 C3 C2 H2B 120.8 C2 C3 C4 122.2(2) C2 C3 Cl2 118.74(16) C4 C3 Cl2 119.03(17) C3 C4 C5 118.3(2) C3 C4 H4A 120.8 C5 C4 H4A 120.8 C4 C5 C6 121.6(2) C4 C5 H5A 119.2 C6 C5 H5A 119.2 C1 C6 C5 118.0(2) C1 C6 C7 122.3(2) C5 C6 C7 119.6(2) O1 C7 N1 125.2(2) O1 C7 C6 122.2(2) N1 C7 C6 112.59(18) N2 C8 N1 113.57(17) N2 C8 S1 123.90(16) N1 C8 S1 122.48(16) N2 C9 C10 113.0(2) N2 C9 H9A 109.0 C10 C9 H9A 109.0 N2 C9 H9B 109.0 C10 C9 H9B 109.0 H9A C9 H9B 107.8 C9 C10 H10A 109.5 C9 C10 H10B 109.5 H10A C10 H10B 109.5 C9 C10 H10C 109.5 H10A C10 H10C 109.5 H10B C10 H10C 109.5 N2 C11 C12 114.4(2) N2 C11 H11A 108.7 C12 C11 H11A 108.7 N2 C11 H11B 108.7 C12 C11 H11B 108.7 H11A C11 H11B 107.6 O2 C12 C11 110.37(19) O2 C12 H12A 109.6 C11 C12 H12A 109.6 O2 C12 H12B 109.6 C11 C12 H12B 109.6 H12A C12 H12B 108.1 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Cl1 C1 1.728(2) Cl2 C3 1.734(2) S1 C8 1.668(2) O1 C7 1.203(3) O2 C12 1.423(3) O2 H2A 0.815(10) N1 C7 1.374(3) N1 C8 1.396(3) N1 H1A 0.8600 N2 C8 1.336(3) N2 C9 1.468(3) N2 C11 1.474(3) C1 C2 1.380(3) C1 C6 1.395(3) C2 C3 1.380(3) C2 H2B 0.9300 C3 C4 1.380(3) C4 C5 1.381(3) C4 H4A 0.9300 C5 C6 1.395(3) C5 H5A 0.9300 C6 C7 1.501(3) C9 C10 1.498(4) C9 H9A 0.9700 C9 H9B 0.9700 C10 H10A 0.9600 C10 H10B 0.9600 C10 H10C 0.9600 C11 C12 1.514(4) C11 H11A 0.9700 C11 H11B 0.9700 C12 H12A 0.9700 C12 H12B 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 N1 H1A O2 1_555 0.86 1.99 2.796(3) 155 yes C9 H9B S1 1_555 0.97 2.64 3.031(3) 105 yes O2 H2A S1 2_656 0.81(3) 2.75(3) 3.438(2) 143(3) yes O2 H2A O1 2_656 0.81(3) 2.25(3) 2.920(3) 140(3) yes 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 C6 C1 C2 C3 0.2(3) Cl1 C1 C2 C3 177.72(15) C1 C2 C3 C4 -0.7(3) C1 C2 C3 Cl2 179.34(15) C2 C3 C4 C5 0.6(3) Cl2 C3 C4 C5 -179.50(16) C3 C4 C5 C6 0.2(3) C2 C1 C6 C5 0.5(3) Cl1 C1 C6 C5 -176.96(15) C2 C1 C6 C7 -175.70(19) Cl1 C1 C6 C7 6.8(3) C4 C5 C6 C1 -0.7(3) C4 C5 C6 C7 175.6(2) C8 N1 C7 O1 13.0(5) C8 N1 C7 C6 -167.0(2) C1 C6 C7 O1 44.6(4) C5 C6 C7 O1 -131.6(3) C1 C6 C7 N1 -135.5(2) C5 C6 C7 N1 48.4(3) C9 N2 C8 N1 -170.21(19) C11 N2 C8 N1 12.9(3) C9 N2 C8 S1 7.5(3) C11 N2 C8 S1 -169.33(17) C7 N1 C8 N2 -160.2(2) C7 N1 C8 S1 22.0(3) C8 N2 C9 C10 -92.3(3) C11 N2 C9 C10 84.8(3) C8 N2 C11 C12 -89.9(3) C9 N2 C11 C12 93.1(2) N2 C11 C12 O2 74.2(3) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139086369