#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/70/2207009.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_2207009 loop_ _publ_author_name 'Xu, Liang-Zhong' 'Yu, Guan-Ping' 'Huang, Yong-Wei' 'Si, Guo-Dong' 'Li, Kai' _publ_section_title 1-(4-Phenyl-3-thioxo-1,2,4-triazolidin-1-yl)-2-(1H-1,2,4-triazol-1-yl)ethanone _journal_issue 10 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3403 _journal_page_last o3404 _journal_paper_doi 10.1107/S1600536805029867 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C12 H12 N6 O S' _chemical_formula_moiety 'C12 H12 N6 O S' _chemical_formula_sum 'C12 H12 N6 O S' _chemical_formula_weight 288.34 _chemical_name_systematic 1-(4-phenyl-3-thioxo-1,2,4-triazolidin-1-yl)-2-(1H-1,2,4-triazol-1-yl)ethanone _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 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 107.362(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.7112(19) _cell_length_b 13.589(3) _cell_length_c 10.711(2) _cell_measurement_reflns_used 1493 _cell_measurement_temperature 294(2) _cell_measurement_theta_max 22.43 _cell_measurement_theta_min 2.49 _cell_volume 1349.1(5) _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction SAINT _computing_molecular_graphics 'SHELXTL (Bruker, 1999)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 294(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \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 0.0496 _diffrn_reflns_av_sigmaI/netI 0.0667 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_number 7473 _diffrn_reflns_theta_full 26.32 _diffrn_reflns_theta_max 26.32 _diffrn_reflns_theta_min 2.20 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.245 _exptl_absorpt_correction_T_max 0.966 _exptl_absorpt_correction_T_min 0.942 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.420 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 600 _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _refine_diff_density_max 0.277 _refine_diff_density_min -0.194 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 185 _refine_ls_number_reflns 2748 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.997 _refine_ls_R_factor_all 0.1025 _refine_ls_R_factor_gt 0.0448 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0520P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0945 _refine_ls_wR_factor_ref 0.1156 _reflns_number_gt 1557 _reflns_number_total 2748 _reflns_threshold_expression I>2\s(I) _cod_data_source_file lh6499.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_cell_volume 1349.0(5) _cod_original_sg_symbol_Hall '-P 2yb c' _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2207009 _cod_database_fobs_code 2207009 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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_type_symbol S1 0.48455(8) 0.68174(5) 0.45003(8) 0.0515(3) Uani d . 1 S N1 0.7120(2) 0.56074(15) 0.5107(2) 0.0385(5) Uani d . 1 N N2 0.7714(2) 0.48294(13) 0.45398(19) 0.0373(5) Uani d . 1 N N3 0.5567(2) 0.52994(13) 0.3165(2) 0.0369(5) Uani d . 1 N N4 1.0114(2) 0.35454(14) 0.7346(2) 0.0401(5) Uani d . 1 N N5 1.1473(2) 0.35944(16) 0.7252(3) 0.0594(7) Uani d . 1 N N6 1.1158(3) 0.21997(15) 0.8267(3) 0.0590(7) Uani d . 1 N O1 0.8705(2) 0.33348(13) 0.47776(19) 0.0574(6) Uani d . 1 O C1 0.5844(3) 0.58960(16) 0.4231(3) 0.0363(6) Uani d . 1 C C2 0.6739(3) 0.46062(17) 0.3252(3) 0.0409(6) Uani d . 1 C H2A 0.6404 0.3931 0.3199 0.049 Uiso calc R 1 H H2B 0.7191 0.4724 0.2572 0.049 Uiso calc R 1 H C3 0.4306(3) 0.52904(17) 0.2071(2) 0.0376(6) Uani d . 1 C C4 0.3803(3) 0.6128(2) 0.1361(3) 0.0542(8) Uani d . 1 C H4 0.4289 0.6721 0.1596 0.065 Uiso calc R 1 H C5 0.2584(3) 0.6090(2) 0.0305(3) 0.0638(9) Uani d . 1 C H5 0.2251 0.6659 -0.0172 0.077 Uiso calc R 1 H C6 0.1857(3) 0.5229(3) -0.0051(3) 0.0707(10) Uani d . 1 C H6 0.1025 0.5211 -0.0760 0.085 Uiso calc R 1 H C7 0.2361(4) 0.4389(2) 0.0644(4) 0.0838(11) Uani d . 1 C H7 0.1872 0.3798 0.0399 0.101 Uiso calc R 1 H C8 0.3591(3) 0.4414(2) 0.1705(3) 0.0635(9) Uani d . 1 C H8 0.3933 0.3842 0.2170 0.076 Uiso calc R 1 H C9 0.8478(3) 0.40966(18) 0.5286(3) 0.0381(6) Uani d . 1 C C10 0.9068(3) 0.42941(17) 0.6733(2) 0.0426(7) Uani d . 1 C H10A 0.9522 0.4937 0.6874 0.051 Uiso calc R 1 H H10B 0.8286 0.4293 0.7123 0.051 Uiso calc R 1 H C11 0.9964(3) 0.27200(18) 0.7938(3) 0.0497(7) Uani d . 1 C H11 0.9115 0.2529 0.8103 0.060 Uiso calc R 1 H C12 1.2040(3) 0.2771(2) 0.7814(3) 0.0657(9) Uani d . 1 C H12 1.2987 0.2592 0.7895 0.079 Uiso calc R 1 H H1 0.770(3) 0.606(2) 0.541(3) 0.065(10) Uiso d . 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 0.0518(4) 0.0422(4) 0.0562(5) 0.0099(3) 0.0097(4) -0.0101(3) N1 0.0431(13) 0.0272(11) 0.0400(14) 0.0018(10) 0.0043(11) -0.0065(10) N2 0.0438(12) 0.0308(10) 0.0352(13) 0.0028(10) 0.0084(11) -0.0040(10) N3 0.0396(12) 0.0308(11) 0.0376(13) 0.0006(9) 0.0074(11) -0.0023(9) N4 0.0385(12) 0.0389(12) 0.0440(14) 0.0073(10) 0.0139(11) 0.0102(10) N5 0.0422(14) 0.0572(15) 0.081(2) 0.0061(12) 0.0212(14) 0.0225(14) N6 0.0613(16) 0.0441(13) 0.073(2) 0.0152(13) 0.0215(15) 0.0210(13) O1 0.0702(13) 0.0474(11) 0.0511(13) 0.0222(10) 0.0128(11) -0.0107(9) C1 0.0396(15) 0.0296(13) 0.0394(16) -0.0052(11) 0.0112(13) 0.0007(12) C2 0.0429(15) 0.0387(14) 0.0395(17) 0.0030(12) 0.0096(13) -0.0046(12) C3 0.0412(15) 0.0397(14) 0.0305(15) -0.0011(12) 0.0085(12) -0.0016(12) C4 0.0613(18) 0.0448(16) 0.0475(19) -0.0024(14) 0.0025(16) 0.0034(14) C5 0.073(2) 0.0617(19) 0.047(2) 0.0127(18) 0.0030(18) 0.0093(16) C6 0.063(2) 0.086(2) 0.046(2) 0.010(2) -0.0091(17) -0.0065(19) C7 0.083(2) 0.070(2) 0.072(3) -0.021(2) -0.018(2) -0.017(2) C8 0.070(2) 0.0433(16) 0.059(2) -0.0058(15) -0.0082(17) -0.0030(15) C9 0.0359(14) 0.0357(14) 0.0431(17) 0.0040(11) 0.0122(13) 0.0023(12) C10 0.0433(16) 0.0393(14) 0.0423(17) 0.0108(12) 0.0082(14) 0.0023(12) C11 0.0516(17) 0.0445(15) 0.057(2) -0.0002(14) 0.0227(16) 0.0141(14) C12 0.0515(19) 0.0639(19) 0.084(3) 0.0226(16) 0.0239(19) 0.0246(18) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C1 N1 N2 108.6(2) C1 N1 H1 115.0(19) N2 N1 H1 114(2) C9 N2 N1 121.0(2) C9 N2 C2 119.65(19) N1 N2 C2 109.12(18) C1 N3 C3 127.2(2) C1 N3 C2 112.1(2) C3 N3 C2 120.74(19) C11 N4 N5 109.1(2) C11 N4 C10 130.7(2) N5 N4 C10 119.9(2) C12 N5 N4 102.1(2) C11 N6 C12 101.5(2) N3 C1 N1 108.5(2) N3 C1 S1 128.0(2) N1 C1 S1 123.55(19) N2 C2 N3 101.59(18) N2 C2 H2A 111.5 N3 C2 H2A 111.5 N2 C2 H2B 111.5 N3 C2 H2B 111.5 H2A C2 H2B 109.3 C4 C3 C8 119.6(3) C4 C3 N3 121.7(2) C8 C3 N3 118.7(2) C5 C4 C3 120.1(3) C5 C4 H4 119.9 C3 C4 H4 119.9 C6 C5 C4 120.7(3) C6 C5 H5 119.7 C4 C5 H5 119.7 C5 C6 C7 119.5(3) C5 C6 H6 120.2 C7 C6 H6 120.2 C6 C7 C8 120.4(3) C6 C7 H7 119.8 C8 C7 H7 119.8 C3 C8 C7 119.7(3) C3 C8 H8 120.2 C7 C8 H8 120.2 O1 C9 N2 120.1(2) O1 C9 C10 123.1(2) N2 C9 C10 116.7(2) N4 C10 C9 109.9(2) N4 C10 H10A 109.7 C9 C10 H10A 109.7 N4 C10 H10B 109.7 C9 C10 H10B 109.7 H10A C10 H10B 108.2 N6 C11 N4 111.8(2) N6 C11 H11 124.1 N4 C11 H11 124.1 N5 C12 N6 115.5(2) N5 C12 H12 122.2 N6 C12 H12 122.2 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S1 C1 1.661(2) yes N1 C1 1.369(3) yes N1 N2 1.425(3) yes N1 H1 0.83(3) ? N2 C9 1.352(3) ? N2 C2 1.453(3) ? N3 C1 1.360(3) ? N3 C3 1.420(3) ? N3 C2 1.459(3) ? N4 C11 1.318(3) yes N4 N5 1.355(3) yes N4 C10 1.449(3) ? N5 C12 1.312(3) yes N6 C11 1.313(3) yes N6 C12 1.349(3) yes O1 C9 1.220(3) ? C2 H2A 0.9700 ? C2 H2B 0.9700 ? C3 C4 1.375(3) ? C3 C8 1.375(3) ? C4 C5 1.372(4) ? C4 H4 0.9300 ? C5 C6 1.361(4) ? C5 H5 0.9300 ? C6 C7 1.371(4) ? C6 H6 0.9300 ? C7 C8 1.382(4) ? C7 H7 0.9300 ? C8 H8 0.9300 ? C9 C10 1.507(3) ? C10 H10A 0.9700 ? C10 H10B 0.9700 ? C11 H11 0.9300 ? C12 H12 0.9300 ? 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 N6 2_756 0.83(3) 2.16(3) 2.962(3) 160(3) C2 H2B N5 3_766 0.97 2.61 3.138(3) 114.7 C5 H5 O1 2_655 0.93 2.54 3.288(4) 137.5 C11 H11 O1 4_566 0.93 2.28 2.978(3) 131.8 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 C1 N1 N2 C9 -146.4(2) C1 N1 N2 C2 -1.4(3) C11 N4 N5 C12 -0.1(3) C10 N4 N5 C12 -174.9(2) C3 N3 C1 N1 174.7(2) C2 N3 C1 N1 -4.1(3) C3 N3 C1 S1 -4.4(4) C2 N3 C1 S1 176.81(18) N2 N1 C1 N3 3.3(3) N2 N1 C1 S1 -177.53(16) C9 N2 C2 N3 144.6(2) N1 N2 C2 N3 -0.9(2) C1 N3 C2 N2 3.1(2) C3 N3 C2 N2 -175.8(2) C1 N3 C3 C4 54.0(4) C2 N3 C3 C4 -127.3(3) C1 N3 C3 C8 -127.1(3) C2 N3 C3 C8 51.6(3) C8 C3 C4 C5 0.9(4) N3 C3 C4 C5 179.7(3) C3 C4 C5 C6 0.2(5) C4 C5 C6 C7 -0.9(5) C5 C6 C7 C8 0.5(6) C4 C3 C8 C7 -1.2(5) N3 C3 C8 C7 180.0(3) C6 C7 C8 C3 0.5(6) N1 N2 C9 O1 163.8(2) C2 N2 C9 O1 22.4(3) N1 N2 C9 C10 -18.8(3) C2 N2 C9 C10 -160.3(2) C11 N4 C10 C9 -94.7(3) N5 N4 C10 C9 78.9(3) O1 C9 C10 N4 10.1(3) N2 C9 C10 N4 -167.2(2) C12 N6 C11 N4 -0.6(3) N5 N4 C11 N6 0.5(3) C10 N4 C11 N6 174.5(3) N4 N5 C12 N6 -0.3(4) C11 N6 C12 N5 0.6(4) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21128768 2 PubChem 71405764