#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/21/2202113.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_2202113 loop_ _publ_author_name 'Bohari M. Yamin' 'M.Sukeri M. Yusof' _publ_section_title ; N,N'-Bis(benzamidothiocarbonyl)hydrazine dimethyl sulfoxide disolvate ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o358 _journal_page_last o359 _journal_paper_doi 10.1107/S1600536803003635 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C16 H14 N4 O2 S2, 2(C2 H6 O S)' _chemical_formula_moiety 'C20 H26 N4 O4 S4' _chemical_formula_sum 'C20 H26 N4 O4 S4' _chemical_formula_weight 514.70 _chemical_name_systematic ; N,N'-Bis(benzamidothiocarbonyl)hydrazine dimethyl sulfoxide disolvate ; _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 93.971(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 6.4127(11) _cell_length_b 15.486(3) _cell_length_c 12.805(2) _cell_measurement_reflns_used 1464 _cell_measurement_temperature 273(2) _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 2.1 _cell_volume 1268.6(4) _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 273(2) _diffrn_detector_area_resol_mean 83.66 _diffrn_measured_fraction_theta_full 0.98 _diffrn_measured_fraction_theta_max 0.98 _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 0.034 _diffrn_reflns_av_sigmaI/netI 0.045 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 7458 _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 0.407 _exptl_absorpt_correction_T_max 0.877 _exptl_absorpt_correction_T_min 0.804 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.347 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 540 _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.33 _refine_diff_density_max 0.39 _refine_diff_density_min -0.18 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.03 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 155 _refine_ls_number_reflns 2862 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.03 _refine_ls_R_factor_all 0.084 _refine_ls_R_factor_gt 0.055 _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^)+(0.0599P)^2^+0.1638P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.121 _refine_ls_wR_factor_ref 0.135 _reflns_number_gt 2008 _reflns_number_total 2862 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ob6215.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' 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 'Monoclinic' changed to 'monoclinic' 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 21/n' _cod_original_formula_sum 'C16 H14 N4 O2 S2, 2(C2 H6 O S)' _cod_database_code 2202113 _cod_database_fobs_code 2202113 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_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 C8 0.1962(4) -0.02424(15) 0.09943(18) 0.0459(6) Uani d . 1 . . C C7 0.4313(4) 0.10169(16) 0.12607(19) 0.0494(6) Uani d . 1 . . C C6 0.6199(4) 0.13210(15) 0.18956(19) 0.0471(6) Uani d . 1 . . C C5 0.6327(5) 0.21923(16) 0.2150(2) 0.0606(7) Uani d . 1 . . C H5 0.5233 0.2561 0.1940 0.073 Uiso calc R 1 . . H C4 0.8070(5) 0.25130(19) 0.2713(2) 0.0671(8) Uani d . 1 . . C H4 0.8134 0.3094 0.2896 0.081 Uiso calc R 1 . . H C3 0.9710(5) 0.1975(2) 0.3003(2) 0.0671(8) Uani d . 1 . . C H3 1.0902 0.2195 0.3363 0.081 Uiso calc R 1 . . H C2 0.9593(5) 0.1108(2) 0.2761(2) 0.0633(8) Uani d . 1 . . C H2 1.0701 0.0744 0.2964 0.076 Uiso calc R 1 . . H C1 0.7836(4) 0.07799(17) 0.2218(2) 0.0525(6) Uani d . 1 . . C H1 0.7751 0.0193 0.2069 0.063 Uiso calc R 1 . . H C9 -0.0485(6) 0.3424(2) -0.0043(3) 0.0917(11) Uani d . 1 . . C H9A -0.1850 0.3251 0.0140 0.137 Uiso calc R 1 . . H H9B 0.0168 0.2955 -0.0386 0.137 Uiso calc R 1 . . H H9C -0.0608 0.3912 -0.0506 0.137 Uiso calc R 1 . . H C10 0.3287(6) 0.4055(3) 0.0486(3) 0.0910(11) Uani d . 1 . . C H10A 0.2898 0.4507 -0.0002 0.136 Uiso calc R 1 . . H H10B 0.3850 0.3577 0.0120 0.136 Uiso calc R 1 . . H H10C 0.4322 0.4267 0.1001 0.136 Uiso calc R 1 . . H N2 0.0878(4) 0.01835(15) 0.02432(16) 0.0530(6) Uani d . 1 . . N H2A 0.118(4) 0.0642(18) 0.006(2) 0.054(8) Uiso d . 1 . . H N1 0.3683(3) 0.01850(13) 0.14610(17) 0.0487(5) Uani d . 1 . . N H1A 0.418(4) -0.0048(18) 0.202(2) 0.068(9) Uiso d . 1 . . H O1 0.3384(3) 0.14790(12) 0.06077(16) 0.0712(6) Uani d . 1 . . O O2 0.0077(3) 0.45101(12) 0.15261(14) 0.0713(6) Uani d . 1 . . O S1 0.13058(13) -0.12222(4) 0.13923(6) 0.0678(3) Uani d . 1 . . S S2 0.10644(12) 0.37118(4) 0.11115(5) 0.0561(2) Uani d . 1 . . S 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 C8 0.0536(15) 0.0403(13) 0.0429(13) 0.0017(11) -0.0022(11) 0.0005(10) C7 0.0566(16) 0.0453(14) 0.0463(14) -0.0037(12) 0.0029(12) 0.0055(11) C6 0.0532(15) 0.0431(14) 0.0456(13) -0.0030(12) 0.0073(11) 0.0035(11) C5 0.0650(18) 0.0435(15) 0.0728(18) -0.0019(13) 0.0016(14) 0.0040(13) C4 0.076(2) 0.0500(17) 0.075(2) -0.0146(15) 0.0021(16) -0.0044(14) C3 0.0613(19) 0.073(2) 0.0664(18) -0.0251(16) -0.0004(14) 0.0035(15) C2 0.0495(17) 0.073(2) 0.0671(18) -0.0021(14) 0.0007(14) 0.0076(15) C1 0.0558(17) 0.0441(15) 0.0578(15) 0.0008(12) 0.0064(13) 0.0008(12) C9 0.101(3) 0.097(3) 0.074(2) 0.005(2) -0.020(2) -0.0299(19) C10 0.096(3) 0.098(3) 0.082(2) -0.007(2) 0.025(2) -0.0033(19) N2 0.0658(15) 0.0438(13) 0.0472(12) -0.0099(11) -0.0117(10) 0.0099(10) N1 0.0549(13) 0.0424(11) 0.0471(12) -0.0034(10) -0.0082(10) 0.0076(10) O1 0.0814(14) 0.0539(11) 0.0747(13) -0.0139(10) -0.0206(11) 0.0245(10) O2 0.0927(16) 0.0657(12) 0.0543(11) 0.0232(11) -0.0032(10) -0.0146(9) S1 0.0825(6) 0.0400(4) 0.0764(5) -0.0093(3) -0.0256(4) 0.0140(3) S2 0.0736(5) 0.0477(4) 0.0467(4) 0.0033(3) 0.0015(3) -0.0052(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' 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' N N 0.0061 0.0033 '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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N2 C8 N1 . . 116.0(2) yes N2 C8 S1 . . 123.1(2) yes N1 C8 S1 . . 120.94(18) yes O1 C7 N1 . . 122.5(2) yes O1 C7 C6 . . 121.9(2) ? N1 C7 C6 . . 115.6(2) ? C1 C6 C5 . . 119.1(2) ? C1 C6 C7 . . 122.9(2) ? C5 C6 C7 . . 118.0(2) ? C4 C5 C6 . . 120.3(3) ? C4 C5 H5 . . 119.8 ? C6 C5 H5 . . 119.8 ? C3 C4 C5 . . 120.0(3) ? C3 C4 H4 . . 120.0 ? C5 C4 H4 . . 120.0 ? C4 C3 C2 . . 120.2(3) ? C4 C3 H3 . . 119.9 ? C2 C3 H3 . . 119.9 ? C3 C2 C1 . . 120.1(3) ? C3 C2 H2 . . 120.0 ? C1 C2 H2 . . 120.0 ? C2 C1 C6 . . 120.3(2) ? C2 C1 H1 . . 119.9 ? C6 C1 H1 . . 119.9 ? S2 C9 H9A . . 109.5 ? S2 C9 H9B . . 109.5 ? H9A C9 H9B . . 109.5 ? S2 C9 H9C . . 109.5 ? H9A C9 H9C . . 109.5 ? H9B C9 H9C . . 109.5 ? S2 C10 H10A . . 109.5 ? S2 C10 H10B . . 109.5 ? H10A C10 H10B . . 109.5 ? S2 C10 H10C . . 109.5 ? H10A C10 H10C . . 109.5 ? H10B C10 H10C . . 109.5 ? C8 N2 N2 . 3 119.8(3) ? C8 N2 H2A . . 123(2) ? N2 N2 H2A 3 . 117(2) ? C7 N1 C8 . . 126.9(2) ? C7 N1 H1A . . 117.1(19) ? C8 N1 H1A . . 114.0(19) ? O2 S2 C10 . . 106.64(16) ? O2 S2 C9 . . 105.94(15) ? C10 S2 C9 . . 96.91(19) ? 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 C8 N2 . 1.323(3) yes C8 N1 . 1.386(3) yes C8 S1 . 1.664(2) yes C7 O1 . 1.224(3) yes C7 N1 . 1.380(3) yes C7 C6 . 1.486(4) ? C6 C1 . 1.384(3) ? C6 C5 . 1.389(3) ? C5 C4 . 1.380(4) ? C5 H5 . 0.9300 ? C4 C3 . 1.372(4) ? C4 H4 . 0.9300 ? C3 C2 . 1.379(4) ? C3 H3 . 0.9300 ? C2 C1 . 1.379(4) ? C2 H2 . 0.9300 ? C1 H1 . 0.9300 ? C9 S2 . 1.780(3) yes C9 H9A . 0.9600 ? C9 H9B . 0.9600 ? C9 H9C . 0.9600 ? C10 S2 . 1.764(3) yes C10 H10A . 0.9600 ? C10 H10B . 0.9600 ? C10 H10C . 0.9600 ? N2 N2 3 1.372(4) yes N2 H2A . 0.78(3) ? N1 H1A . 0.85(3) ? O2 S2 . 1.5026(19) yes 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 0.78(3) 2.01(3) 2.593(3) 132(2) yes N2 H2A S1 3_555 0.78(3) 2.53(3) 2.920(2) 113(2) yes N1 H1A O2 2_545 0.84(3) 2.01(3) 2.843(3) 169(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_site_symmetry_4 _geom_torsion O1 C7 C6 C1 . -146.5(3) N1 C7 C6 C1 . 33.8(3) O1 C7 C6 C5 . 31.9(4) N1 C7 C6 C5 . -147.8(2) C1 C6 C5 C4 . 0.3(4) C7 C6 C5 C4 . -178.2(3) C6 C5 C4 C3 . 1.6(4) C5 C4 C3 C2 . -2.0(4) C4 C3 C2 C1 . 0.6(4) C3 C2 C1 C6 . 1.3(4) C5 C6 C1 C2 . -1.7(4) C7 C6 C1 C2 . 176.7(2) N1 C8 N2 N2 3 -178.4(3) S1 C8 N2 N2 3 0.1(4) O1 C7 N1 C8 . -1.1(4) C6 C7 N1 C8 . 178.6(2) N2 C8 N1 C7 . 3.5(4) S1 C8 N1 C7 . -175.1(2) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139065846