#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/22/2202231.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_2202231 loop_ _publ_author_name 'Chan, Mun Hoe Eddy' 'Crouse, Karen A.' 'Tarafder, M. T. H.' 'Yamin, Bohari. M.' _publ_section_title ; Benzyl N-[1-(thiophen-2-yl)ethylidene)]hydrazinecarbodithioate ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o628 _journal_page_last o629 _journal_paper_doi 10.1107/S1600536803007517 _journal_volume 59 _journal_year 2003 _chemical_formula_moiety 'C14 H14 N2 S3' _chemical_formula_sum 'C14 H14 N2 S3' _chemical_formula_weight 306.45 _chemical_name_systematic ; N-(1-thiophene-2-yl-ethylidene)-hydrazinecarbodithioic acid benzyl ester ; _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 65.369(3) _cell_angle_beta 75.843(3) _cell_angle_gamma 77.150(3) _cell_formula_units_Z 2 _cell_length_a 7.8297(13) _cell_length_b 9.8086(16) _cell_length_c 11.0310(18) _cell_measurement_reflns_used 5262 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 2.1 _cell_volume 739.7(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 _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 293(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 diffractometer ; _diffrn_measurement_method '\w scan' _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 0.016 _diffrn_reflns_av_sigmaI/netI 0.018 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 9682 _diffrn_reflns_theta_full 27.5 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_min 2.1 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.488 _exptl_absorpt_correction_T_max 0.905 _exptl_absorpt_correction_T_min 0.807 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.376 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 320 _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.21 _refine_diff_density_max 0.31 _refine_diff_density_min -0.29 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 173 _refine_ls_number_reflns 3405 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.035 _refine_ls_R_factor_all 0.043 _refine_ls_R_factor_gt 0.039 _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^)+(0.0630P)^2^+0.1918P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.109 _refine_ls_wR_factor_ref 0.113 _reflns_number_gt 3012 _reflns_number_total 3405 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ww6069.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_original_sg_symbol_H-M P-1 _cod_database_code 2202231 _cod_database_fobs_code 2202231 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 0.37330(5) 0.09814(5) 0.34859(4) 0.05016(14) Uani d . 1 . . S S2 0.33305(7) 0.43778(5) 0.19451(5) 0.06214(16) Uani d . 1 . . S S3 0.74689(7) -0.23321(6) 0.20144(5) 0.06809(17) Uani d . 1 . . S N1 0.52191(19) 0.23551(16) 0.10104(15) 0.0526(3) Uani d . 1 . . N H1A 0.5426 0.3081 0.0236 0.063 Uiso calc R 1 . . H N2 0.59887(19) 0.08931(16) 0.11927(15) 0.0500(3) Uani d . 1 . . N C1 -0.0544(3) 0.3186(3) 0.5255(2) 0.0639(5) Uani d . 1 . . C H1 0.0011 0.3451 0.5765 0.077 Uiso calc R 1 . . H C2 -0.2325(3) 0.3694(3) 0.5196(2) 0.0801(7) Uani d . 1 . . C H2 -0.2964 0.4288 0.5674 0.096 Uiso calc R 1 . . H C3 -0.3149(3) 0.3332(3) 0.4441(3) 0.0772(7) Uani d . 1 . . C H3 -0.4345 0.3687 0.4392 0.093 Uiso calc R 1 . . H C4 -0.2215(3) 0.2446(3) 0.3756(3) 0.0749(6) Uani d . 1 . . C H4 -0.2776 0.2197 0.3239 0.090 Uiso calc R 1 . . H C5 -0.0440(3) 0.1916(2) 0.3826(2) 0.0604(4) Uani d . 1 . . C H5 0.0179 0.1298 0.3366 0.073 Uiso calc R 1 . . H C6 0.0426(2) 0.22882(18) 0.45635(16) 0.0456(3) Uani d . 1 . . C C7 0.2357(2) 0.1733(2) 0.46939(18) 0.0515(4) Uani d . 1 . . C H7A 0.2404 0.0954 0.5592 0.062 Uiso calc R 1 . . H H7B 0.2884 0.2568 0.4639 0.062 Uiso calc R 1 . . H C8 0.4141(2) 0.26343(18) 0.20559(17) 0.0463(3) Uani d . 1 . . C C9 0.6901(2) 0.06283(18) 0.01655(16) 0.0452(3) Uani d . 1 . . C C10 0.7763(2) -0.09249(18) 0.04300(17) 0.0462(3) Uani d . 1 . . C C11 0.8851(3) -0.3636(2) 0.1462(3) 0.0714(6) Uani d . 1 . . C H11 0.9105 -0.4647 0.2018 0.086 Uiso calc R 1 . . H C12 0.9533(3) -0.3057(2) 0.0147(3) 0.0746(6) Uani d . 1 . . C H12 1.0318 -0.3614 -0.0315 0.089 Uiso calc R 1 . . H C13 0.8915(3) -0.1482(2) -0.0467(2) 0.0663(5) Uani d . 1 . . C H13 0.9255 -0.0896 -0.1377 0.080 Uiso calc R 1 . . H C14 0.7158(3) 0.1744(2) -0.12607(19) 0.0626(5) Uani d . 1 . . C H14A 0.6138 0.2510 -0.1398 0.094 Uiso calc R 1 . . H H14B 0.7301 0.1235 -0.1865 0.094 Uiso calc R 1 . . H H14C 0.8200 0.2207 -0.1438 0.094 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 S1 0.0456(2) 0.0432(2) 0.0506(2) 0.00041(16) -0.00379(17) -0.01294(18) S2 0.0642(3) 0.0408(2) 0.0663(3) 0.00181(19) 0.0027(2) -0.0180(2) S3 0.0679(3) 0.0564(3) 0.0575(3) 0.0049(2) -0.0046(2) -0.0102(2) N1 0.0521(8) 0.0410(7) 0.0516(8) -0.0001(6) -0.0003(6) -0.0130(6) N2 0.0465(7) 0.0415(7) 0.0530(8) 0.0013(5) -0.0044(6) -0.0153(6) C1 0.0622(11) 0.0729(12) 0.0568(10) 0.0068(9) -0.0130(8) -0.0316(10) C2 0.0653(13) 0.0865(16) 0.0727(14) 0.0164(11) -0.0029(11) -0.0335(12) C3 0.0423(10) 0.0777(15) 0.0865(15) -0.0018(9) -0.0057(10) -0.0132(12) C4 0.0572(11) 0.0761(14) 0.0959(16) -0.0150(10) -0.0259(11) -0.0272(12) C5 0.0513(10) 0.0668(11) 0.0711(12) -0.0070(8) -0.0124(8) -0.0336(10) C6 0.0421(8) 0.0468(8) 0.0411(7) -0.0057(6) -0.0039(6) -0.0122(6) C7 0.0449(8) 0.0608(10) 0.0476(8) -0.0024(7) -0.0093(7) -0.0213(8) C8 0.0385(7) 0.0424(8) 0.0521(8) -0.0008(6) -0.0076(6) -0.0149(7) C9 0.0438(8) 0.0427(8) 0.0474(8) -0.0047(6) -0.0083(6) -0.0159(7) C10 0.0482(8) 0.0438(8) 0.0462(8) -0.0038(6) -0.0104(6) -0.0169(7) C11 0.0738(13) 0.0457(10) 0.0855(15) 0.0049(9) -0.0194(11) -0.0195(10) C12 0.0923(16) 0.0533(11) 0.0783(14) 0.0095(10) -0.0132(12) -0.0358(11) C13 0.0893(14) 0.0516(10) 0.0559(10) 0.0015(9) -0.0079(10) -0.0267(9) C14 0.0812(13) 0.0478(9) 0.0500(10) -0.0075(9) -0.0069(9) -0.0132(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' 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 C8 S1 C7 101.92(8) yes C11 S3 C10 91.97(10) ? C8 N1 N2 119.20(14) ? C8 N1 H1A 120.4 ? N2 N1 H1A 120.4 ? C9 N2 N1 118.42(14) yes C2 C1 C6 120.8(2) ? C2 C1 H1 119.6 ? C6 C1 H1 119.6 ? C3 C2 C1 120.3(2) ? C3 C2 H2 119.9 ? C1 C2 H2 119.9 ? C2 C3 C4 119.66(19) ? C2 C3 H3 120.2 ? C4 C3 H3 120.2 ? C3 C4 C5 120.4(2) ? C3 C4 H4 119.8 ? C5 C4 H4 119.8 ? C6 C5 C4 120.95(19) ? C6 C5 H5 119.5 ? C4 C5 H5 119.5 ? C5 C6 C1 117.95(17) ? C5 C6 C7 123.59(16) ? C1 C6 C7 118.44(16) ? C6 C7 S1 117.69(12) ? C6 C7 H7A 107.9 ? S1 C7 H7A 107.9 ? C6 C7 H7B 107.9 ? S1 C7 H7B 107.9 ? H7A C7 H7B 107.2 ? N1 C8 S2 121.51(13) yes N1 C8 S1 112.89(12) yes S2 C8 S1 125.60(10) yes N2 C9 C10 116.05(15) ? N2 C9 C14 126.35(16) ? C10 C9 C14 117.60(15) ? C13 C10 C9 127.77(16) ? C13 C10 S3 110.35(13) ? C9 C10 S3 121.86(13) ? C12 C11 S3 112.98(16) ? C12 C11 H11 123.5 ? S3 C11 H11 123.5 ? C11 C12 C13 111.98(19) ? C11 C12 H12 124.0 ? C13 C12 H12 124.0 ? C10 C13 C12 112.73(19) ? C10 C13 H13 123.6 ? C12 C13 H13 123.6 ? C9 C14 H14A 109.5 ? C9 C14 H14B 109.5 ? H14A C14 H14B 109.5 ? C9 C14 H14C 109.5 ? H14A C14 H14C 109.5 ? H14B C14 H14C 109.5 ? 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 . 1.7525(17) yes S1 C7 . 1.8009(18) yes S2 C8 . 1.6503(17) yes S3 C11 . 1.700(2) ? S3 C10 . 1.7165(17) ? N1 C8 . 1.342(2) yes N1 N2 . 1.3765(19) yes N1 H1A . 0.8600 ? N2 C9 . 1.276(2) yes C1 C2 . 1.381(3) ? C1 C6 . 1.383(2) ? C1 H1 . 0.9300 ? C2 C3 . 1.360(4) ? C2 H2 . 0.9300 ? C3 C4 . 1.362(4) ? C3 H3 . 0.9300 ? C4 C5 . 1.381(3) ? C4 H4 . 0.9300 ? C5 C6 . 1.371(2) ? C5 H5 . 0.9300 ? C6 C7 . 1.510(2) ? C7 H7A . 0.9700 ? C7 H7B . 0.9700 ? C9 C10 . 1.460(2) ? C9 C14 . 1.490(2) ? C10 C13 . 1.373(3) ? C11 C12 . 1.335(3) ? C11 H11 . 0.9300 ? C12 C13 . 1.426(3) ? C12 H12 . 0.9300 ? C13 H13 . 0.9300 ? C14 H14A . 0.9600 ? C14 H14B . 0.9600 ? C14 H14C . 0.9600 ? 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 S2 2_665 0.86 2.81 3.6450(17) 165 yes C5 H5 S1 1_555 0.93 2.76 3.164(2) 107 yes C7 H7B S2 1_555 0.97 2.73 3.114(2) 104 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 C8 N1 N2 C9 174.78(15) C6 C1 C2 C3 -0.8(4) C1 C2 C3 C4 0.9(4) C2 C3 C4 C5 0.0(4) C3 C4 C5 C6 -1.1(4) C4 C5 C6 C1 1.2(3) C4 C5 C6 C7 179.29(19) C2 C1 C6 C5 -0.3(3) C2 C1 C6 C7 -178.5(2) C5 C6 C7 S1 17.1(2) C1 C6 C7 S1 -164.82(15) C8 S1 C7 C6 77.65(15) N2 N1 C8 S2 174.13(12) N2 N1 C8 S1 -5.8(2) C7 S1 C8 N1 177.78(13) C7 S1 C8 S2 -2.12(14) N1 N2 C9 C10 176.87(14) N1 N2 C9 C14 -3.3(3) N2 C9 C10 C13 -174.75(19) C14 C9 C10 C13 5.4(3) N2 C9 C10 S3 3.4(2) C14 C9 C10 S3 -176.48(14) C11 S3 C10 C13 -0.64(16) C11 S3 C10 C9 -179.06(15) C10 S3 C11 C12 0.6(2) S3 C11 C12 C13 -0.4(3) C9 C10 C13 C12 178.83(18) S3 C10 C13 C12 0.5(2) C11 C12 C13 C10 -0.1(3) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 8525496 2 PubChem 10350041