#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/25/2202558.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_2202558 loop_ _publ_author_name 'Ocak, Nazan' 'Kahveci, Bahattin' '\,Sa\,smaz, Selami' 'A\m-Chlorobenzylamino)-3-methyl-4,5-dihydro-1H-1,2,4-triazol-5-one _journal_issue 8 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1137 _journal_page_last o1138 _journal_paper_doi 10.1107/S1600536803015058 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C10 H11 Cl N4 O' _chemical_formula_moiety 'C10 H11 Cl N4 O' _chemical_formula_sum 'C10 H11 Cl N4 O' _chemical_formula_weight 238.68 _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 _cell_angle_alpha 90.00 _cell_angle_beta 114.963(7) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 14.3423(15) _cell_length_b 5.8708(3) _cell_length_c 15.2730(14) _cell_measurement_reflns_used 14391 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 29.30 _cell_measurement_theta_min 1.71 _cell_volume 1165.86(19) _computing_cell_refinement X-AREA _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_data_reduction 'X-RED (Stoe & Cie, 2002)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)' _computing_publication_material 'WinGX (Farrugia, 1999), PARST (Nardelli, 1995) and PLATON (Spek, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 6.67 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Stoe IPDS-II' _diffrn_measurement_method 'rotation method' _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 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0301 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 3218 _diffrn_reflns_theta_full 29.44 _diffrn_reflns_theta_max 29.44 _diffrn_reflns_theta_min 2.69 _exptl_absorpt_coefficient_mu 0.312 _exptl_absorpt_correction_T_max 0.9232 _exptl_absorpt_correction_T_min 0.8394 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details '(X-RED; Stoe & Cie, 2002)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.360 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prismatic _exptl_crystal_F_000 496 _exptl_crystal_size_max 0.600 _exptl_crystal_size_mid 0.460 _exptl_crystal_size_min 0.280 _refine_diff_density_max 0.510 _refine_diff_density_min -0.426 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.856 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 145 _refine_ls_number_reflns 3218 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.856 _refine_ls_R_factor_all 0.1004 _refine_ls_R_factor_gt 0.0625 _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^)+(0.1356P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1899 _refine_ls_wR_factor_ref 0.2053 _reflns_number_gt 1519 _reflns_number_total 3218 _reflns_threshold_expression I>2sigma(I) _cod_data_source_file cv6206.cif _cod_data_source_block I _cod_original_cell_volume 1165.86(17) _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2202558 _cod_database_fobs_code 2202558 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C3 0.8370(4) 0.0088(8) 0.8114(4) 0.1042(13) Uani d . 1 . . C H3 0.8882 -0.0928 0.8149 0.125 Uiso calc R 1 . . H C4 0.8617(3) 0.1920(7) 0.8764(3) 0.0935(11) Uani d . 1 . . C H4 0.9288 0.2121 0.9226 0.112 Uiso calc R 1 . . H O1 0.96137(14) 0.4083(3) 1.16108(13) 0.0729(5) Uani d . 1 . . O C2 0.7405(4) -0.0218(6) 0.7443(3) 0.0943(11) Uani d . 1 . . C H2 0.7249 -0.1444 0.7020 0.113 Uiso calc R 1 . . H C7 0.8070(3) 0.5315(5) 0.9425(2) 0.0869(10) Uani d . 1 . . C H7A 0.8807 0.5448 0.9804 0.104 Uiso calc R 1 . . H H7B 0.7824 0.6739 0.9084 0.104 Uiso calc R 1 . . H C10 0.89134(17) 0.2665(4) 1.13455(14) 0.0510(5) Uani d . 1 . . C C5 0.7855(2) 0.3420(5) 0.87106(18) 0.0658(7) Uani d . 1 . . C N3 0.88941(15) 0.0553(3) 1.16510(13) 0.0572(5) Uani d . 1 . . N H3A 0.9416 -0.0103 1.2095 0.069 Uiso calc R 1 . . H C1 0.6664(3) 0.1265(5) 0.73876(19) 0.0751(8) Uani d . 1 . . C C6 0.6870(2) 0.3086(5) 0.80052(18) 0.0664(7) Uani d . 1 . . C H6 0.6348 0.4095 0.7949 0.080 Uiso calc R 1 . . H N2 0.79365(13) 0.2948(3) 1.06236(12) 0.0463(4) Uani d . 1 . . N N1 0.75691(18) 0.4909(3) 1.00719(13) 0.0641(6) Uani d . 1 . . N H1 0.7103 0.5779 1.0107 0.077 Uiso calc R 1 . . H N4 0.79494(16) -0.0470(3) 1.11810(14) 0.0587(5) Uani d . 1 . . N C8 0.73907(17) 0.1019(3) 1.05554(15) 0.0479(5) Uani d . 1 . . C Cl1 0.54065(9) 0.0838(2) 0.65249(7) 0.1302(5) Uani d . 1 . . Cl C9 0.6299(2) 0.0695(5) 0.9878(2) 0.0744(8) Uani d . 1 . . C H9A 0.6051 0.2038 0.9491 0.112 Uiso calc R 1 . . H H9B 0.5899 0.0423 1.0238 0.112 Uiso calc R 1 . . H H9C 0.6240 -0.0587 0.9468 0.112 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 C3 0.120(3) 0.104(3) 0.129(3) 0.030(3) 0.092(3) 0.034(3) C4 0.0710(18) 0.116(3) 0.099(2) -0.0012(19) 0.0410(17) 0.039(2) O1 0.0712(11) 0.0676(12) 0.0576(9) -0.0243(9) 0.0056(8) -0.0055(8) C2 0.150(3) 0.078(2) 0.092(2) 0.003(2) 0.087(3) 0.0044(18) C7 0.116(2) 0.0664(17) 0.0601(15) -0.0331(17) 0.0200(16) 0.0120(13) C10 0.0567(12) 0.0469(12) 0.0383(9) -0.0031(10) 0.0092(9) -0.0048(9) C5 0.0733(16) 0.0670(15) 0.0564(13) -0.0108(13) 0.0268(12) 0.0164(12) N3 0.0581(11) 0.0478(11) 0.0489(10) 0.0041(9) 0.0062(8) 0.0058(8) C1 0.100(2) 0.0775(19) 0.0546(14) -0.0116(17) 0.0393(15) -0.0046(13) C6 0.0752(16) 0.0672(16) 0.0564(13) 0.0040(13) 0.0273(12) 0.0021(12) N2 0.0555(10) 0.0349(8) 0.0394(8) -0.0005(7) 0.0110(7) 0.0006(6) N1 0.0855(14) 0.0365(9) 0.0509(10) 0.0052(9) 0.0099(10) 0.0060(8) N4 0.0668(12) 0.0443(10) 0.0543(10) -0.0054(9) 0.0151(9) 0.0039(8) C8 0.0554(12) 0.0383(10) 0.0469(10) -0.0027(9) 0.0186(9) -0.0014(8) Cl1 0.1346(9) 0.1493(11) 0.0759(6) -0.0396(8) 0.0143(6) -0.0252(6) C9 0.0547(14) 0.0764(18) 0.0755(17) -0.0105(13) 0.0113(12) 0.0056(14) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C2 C3 C4 120.9(4) C2 C3 H3 119.5 C4 C3 H3 119.5 C5 C4 C3 119.4(3) C5 C4 H4 120.3 C3 C4 H4 120.3 C3 C2 C1 119.5(4) C3 C2 H2 120.2 C1 C2 H2 120.2 N1 C7 C5 111.2(2) N1 C7 H7A 109.4 C5 C7 H7A 109.4 N1 C7 H7B 109.4 C5 C7 H7B 109.4 H7A C7 H7B 108.0 O1 C10 N3 130.5(2) O1 C10 N2 126.4(2) N3 C10 N2 103.19(18) C4 C5 C6 118.6(3) C4 C5 C7 121.1(3) C6 C5 C7 120.2(3) C10 N3 N4 112.71(18) C10 N3 H3A 123.6 N4 N3 H3A 123.6 C2 C1 C6 121.6(3) C2 C1 Cl1 119.4(3) C6 C1 Cl1 119.0(3) C1 C6 C5 119.9(3) C1 C6 H6 120.0 C5 C6 H6 120.0 C8 N2 C10 108.65(17) C8 N2 N1 125.85(18) C10 N2 N1 125.49(19) N2 N1 C7 112.0(2) N2 N1 H1 124.0 C7 N1 H1 124.0 C8 N4 N3 104.91(18) N4 C8 N2 110.50(19) N4 C8 C9 124.9(2) N2 C8 C9 124.6(2) C8 C9 H9A 109.5 C8 C9 H9B 109.5 H9A C9 H9B 109.5 C8 C9 H9C 109.5 H9A C9 H9C 109.5 H9B C9 H9C 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 C3 C2 . 1.341(6) ? C3 C4 . 1.404(6) ? C3 H3 . 0.9300 ? C4 C5 . 1.379(5) ? C4 H4 . 0.9300 ? O1 C10 . 1.234(3) yes C2 C1 . 1.349(5) ? C2 H2 . 0.9300 ? C7 N1 . 1.465(4) ? C7 C5 . 1.497(4) ? C7 H7A . 0.9700 ? C7 H7B . 0.9700 ? C10 N3 . 1.330(3) yes C10 N2 . 1.379(3) yes C5 C6 . 1.381(4) ? N3 N4 . 1.375(3) yes N3 H3A . 0.8600 ? C1 C6 . 1.373(4) ? C1 Cl1 . 1.746(3) yes C6 H6 . 0.9300 ? N2 C8 . 1.356(3) yes N2 N1 . 1.392(2) yes N1 H1 . 0.8600 ? N4 C8 . 1.293(3) yes C8 C9 . 1.480(3) yes C9 H9A . 0.9600 ? C9 H9B . 0.9600 ? C9 H9C . 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 N3 H3A O1 2_747 0.86 1.94 2.752(2) 158 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 C2 C3 C4 C5 0.1(5) C4 C3 C2 C1 0.5(5) C3 C4 C5 C6 -1.0(4) C3 C4 C5 C7 176.3(3) N1 C7 C5 C4 -109.9(3) N1 C7 C5 C6 67.4(3) O1 C10 N3 N4 178.6(2) N2 C10 N3 N4 -2.0(2) C3 C2 C1 C6 -0.3(5) C3 C2 C1 Cl1 -179.1(3) C2 C1 C6 C5 -0.6(4) Cl1 C1 C6 C5 178.2(2) C4 C5 C6 C1 1.2(4) C7 C5 C6 C1 -176.1(2) O1 C10 N2 C8 -179.4(2) N3 C10 N2 C8 1.2(2) O1 C10 N2 N1 -0.6(4) N3 C10 N2 N1 -180.0(2) C8 N2 N1 C7 -113.2(3) C10 N2 N1 C7 68.2(3) C5 C7 N1 N2 62.5(3) C10 N3 N4 C8 2.0(3) N3 N4 C8 N2 -1.1(2) N3 N4 C8 C9 -179.5(2) C10 N2 C8 N4 0.0(3) N1 N2 C8 N4 -178.8(2) C10 N2 C8 C9 178.3(2) N1 N2 C8 C9 -0.5(3) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21131587 2 PubChem 139066093