#------------------------------------------------------------------------------ #$Date: 2017-10-13 07:09:21 +0100 (Fri, 13 Oct 2017) $ #$Revision: 201973 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/52/2205239.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_2205239 loop_ _publ_author_name 'Fu-You Pan' 'Jian-Guo Yang' _publ_section_title ; 3-[(4-Fluorophenyl)methylenehydrazinocarbonyl]-1H-1,2,4-triazole monohydrate ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o712 _journal_page_last o713 _journal_paper_doi 10.1107/S1600536805004162 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C10 H8 F N5 O, H2 O' _chemical_formula_moiety 'C10 H8 F N5 O, H2 O' _chemical_formula_sum 'C10 H10 F N5 O2' _chemical_formula_weight 251.23 _chemical_name_systematic ; 3-[(4-Fluorophenyl)methylenehydrazinocarbonyl]-1H-1,2,4-triazole monohydrate ; _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 93.70(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 21.394(2) _cell_length_b 7.796(2) _cell_length_c 6.918(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 12.48 _cell_measurement_theta_min 8.37 _cell_volume 1151.4(5) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf--Nonius, 1989)' _computing_data_reduction 'CAD-4 Software' _computing_molecular_graphics 'SHELXTL (Bruker, 2002)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 295(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Enraf--Nonius CAD-4' _diffrn_measurement_method \w/2\q _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 0.0643 _diffrn_reflns_av_sigmaI/netI 0.1398 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2623 _diffrn_reflns_theta_full 25.18 _diffrn_reflns_theta_max 25.18 _diffrn_reflns_theta_min 2.78 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_type none _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.449 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 520 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.285 _refine_diff_density_min -0.255 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 171 _refine_ls_number_reflns 2072 _refine_ls_number_restraints 3 _refine_ls_restrained_S_all 1.010 _refine_ls_R_factor_all 0.2202 _refine_ls_R_factor_gt 0.0569 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0903P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1315 _refine_ls_wR_factor_ref 0.1888 _reflns_number_gt 786 _reflns_number_total 2072 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ci6525.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/c' _cod_database_code 2205239 _cod_database_fobs_code 2205239 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 F1 0.95154(15) 1.2356(5) 0.8822(6) 0.1019(14) Uani d . 1 F O1 0.60776(13) 0.8066(4) 0.3476(5) 0.0479(9) Uani d . 1 O H21 0.694(2) 0.326(5) 0.792(10) 0.12(3) Uiso d D 1 H H22 0.715(3) 0.483(6) 0.862(8) 0.14(3) Uiso d D 1 H O2 0.72091(17) 0.4040(5) 0.7805(6) 0.0559(10) Uani d D 1 O N1 0.72591(16) 0.7843(4) 0.5281(5) 0.0376(10) Uani d . 1 N N2 0.68875(15) 0.6451(5) 0.4747(5) 0.0376(10) Uani d . 1 N H2 0.7027 0.5429 0.4961 0.045 Uiso calc R 1 H N3 0.53760(18) 0.5053(5) 0.2974(6) 0.0452(10) Uani d . 1 N N4 0.62348(17) 0.3459(5) 0.3700(6) 0.0459(11) Uani d . 1 N N5 0.52421(17) 0.3365(5) 0.2802(6) 0.0475(11) Uani d . 1 N H5 0.4879 0.2947 0.2462 0.057 Uiso calc R 1 H C1 0.9093(2) 1.1180(8) 0.8123(8) 0.0631(17) Uani d . 1 C C2 0.9296(3) 0.9550(9) 0.7828(9) 0.0736(19) Uani d . 1 C H2A 0.9715 0.9256 0.8089 0.088 Uiso calc R 1 H C3 0.8865(2) 0.8346(8) 0.7133(8) 0.0614(15) Uani d . 1 C H3 0.8996 0.7224 0.6945 0.074 Uiso calc R 1 H C4 0.8248(2) 0.8767(6) 0.6713(7) 0.0425(12) Uani d . 1 C C5 0.8058(2) 1.0450(6) 0.7086(7) 0.0493(13) Uani d . 1 C H5A 0.7640 1.0758 0.6852 0.059 Uiso calc R 1 H C6 0.8485(2) 1.1645(7) 0.7797(7) 0.0562(14) Uani d . 1 C H6 0.8359 1.2760 0.8052 0.067 Uiso calc R 1 H C7 0.7804(2) 0.7471(6) 0.6035(6) 0.0419(12) Uani d . 1 C H7 0.7918 0.6323 0.6151 0.050 Uiso calc R 1 H C8 0.63178(19) 0.6675(6) 0.3907(6) 0.0342(10) Uani d . 1 C C9 0.59735(19) 0.5051(5) 0.3517(6) 0.0338(10) Uani d . 1 C C10 0.5749(2) 0.2456(6) 0.3230(7) 0.0465(13) Uani d . 1 C H10 0.5764 0.1264 0.3208 0.056 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 F1 0.076(2) 0.107(3) 0.121(3) -0.045(2) -0.004(2) -0.034(2) O1 0.0483(19) 0.0316(18) 0.063(2) 0.0024(16) 0.0002(17) 0.0082(16) O2 0.059(2) 0.038(2) 0.070(3) -0.002(2) -0.0008(18) 0.003(2) N1 0.040(2) 0.032(2) 0.041(2) -0.0035(18) 0.0016(18) -0.0013(17) N2 0.040(2) 0.025(2) 0.047(2) -0.0010(17) 0.0028(18) -0.0065(17) N3 0.048(2) 0.030(2) 0.058(3) -0.0037(19) 0.002(2) -0.004(2) N4 0.047(2) 0.029(2) 0.060(3) 0.001(2) -0.001(2) -0.003(2) N5 0.049(2) 0.030(2) 0.063(3) -0.008(2) 0.004(2) -0.006(2) C1 0.048(3) 0.079(5) 0.062(4) -0.027(3) 0.002(3) -0.009(3) C2 0.049(3) 0.087(5) 0.083(5) -0.004(3) -0.007(3) -0.019(4) C3 0.055(3) 0.066(4) 0.062(4) 0.009(3) -0.001(3) -0.012(3) C4 0.045(3) 0.043(3) 0.040(3) 0.000(2) 0.004(2) 0.001(2) C5 0.048(3) 0.048(3) 0.052(3) -0.003(3) 0.004(2) -0.001(3) C6 0.068(4) 0.045(3) 0.056(4) -0.015(3) 0.005(3) -0.010(3) C7 0.048(3) 0.039(3) 0.039(3) 0.000(2) 0.010(2) 0.001(2) C8 0.035(2) 0.034(3) 0.034(3) 0.001(2) 0.003(2) 0.003(2) C9 0.034(2) 0.032(3) 0.034(3) 0.001(2) -0.001(2) -0.001(2) C10 0.052(3) 0.030(2) 0.056(4) 0.001(3) -0.004(2) -0.003(2) 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' F F 0.0171 0.0103 '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 H21 O2 H22 109(3) C7 N1 N2 115.1(4) C8 N2 N1 120.6(4) C8 N2 H2 119.7 N1 N2 H2 119.7 C9 N3 N5 102.8(4) C10 N4 C9 101.7(4) C10 N5 N3 109.8(4) C10 N5 H5 125.1 N3 N5 H5 125.1 C6 C1 F1 119.3(6) C6 C1 C2 122.5(5) F1 C1 C2 118.2(5) C1 C2 C3 118.2(5) C1 C2 H2A 120.9 C3 C2 H2A 120.9 C4 C3 C2 121.5(5) C4 C3 H3 119.2 C2 C3 H3 119.2 C3 C4 C5 118.1(5) C3 C4 C7 120.4(5) C5 C4 C7 121.4(4) C6 C5 C4 120.4(5) C6 C5 H5A 119.8 C4 C5 H5A 119.8 C1 C6 C5 119.1(5) C1 C6 H6 120.4 C5 C6 H6 120.4 N1 C7 C4 122.5(4) N1 C7 H7 118.7 C4 C7 H7 118.7 O1 C8 N2 125.5(4) O1 C8 C9 121.0(4) N2 C8 C9 113.5(4) N3 C9 N4 114.5(4) N3 C9 C8 121.1(4) N4 C9 C8 124.4(4) N5 C10 N4 111.2(4) N5 C10 H10 124.4 N4 C10 H10 124.4 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance F1 C1 1.355(6) O1 C8 1.229(5) O2 H21 0.850(10) O2 H22 0.850(10) N1 C7 1.279(5) N1 N2 1.382(4) N2 C8 1.328(5) N2 H2 0.86 N3 C9 1.309(5) N3 N5 1.351(5) N4 C10 1.325(5) N4 C9 1.364(5) N5 C10 1.312(5) N5 H5 0.86 C1 C6 1.355(7) C1 C2 1.363(8) C2 C3 1.380(7) C2 H2A 0.93 C3 C4 1.373(6) C3 H3 0.93 C4 C5 1.403(6) C4 C7 1.445(6) C5 C6 1.374(6) C5 H5A 0.93 C6 H6 0.93 C7 H7 0.93 C8 C9 1.481(6) C10 H10 0.93 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 N5 H5 N3 2_645 0.86 2.34 2.934(5) 127 N5 H5 O1 2_645 0.86 2.11 2.913(5) 155 N2 H2 O2 . 0.86 2.26 2.880(5) 129 O2 H22 N1 4_576 0.850(10) 2.16(2) 2.971(5) 161(6) O2 H21 N4 4_566 0.850(10) 2.11(2) 2.948(5) 169(6) 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 C7 N1 N2 C8 -178.4(4) C9 N3 N5 C10 -0.1(5) C6 C1 C2 C3 1.4(9) F1 C1 C2 C3 179.4(5) C1 C2 C3 C4 1.1(9) C2 C3 C4 C5 -2.7(8) C2 C3 C4 C7 -178.4(5) C3 C4 C5 C6 2.0(7) C7 C4 C5 C6 177.6(5) F1 C1 C6 C5 179.9(5) C2 C1 C6 C5 -2.1(9) C4 C5 C6 C1 0.3(8) N2 N1 C7 C4 -178.7(4) C3 C4 C7 N1 -166.4(5) C5 C4 C7 N1 18.1(7) N1 N2 C8 O1 2.4(6) N1 N2 C8 C9 -177.2(4) N5 N3 C9 N4 0.2(5) N5 N3 C9 C8 -179.2(4) C10 N4 C9 N3 -0.2(5) C10 N4 C9 C8 179.1(4) O1 C8 C9 N3 -10.2(7) N2 C8 C9 N3 169.4(4) O1 C8 C9 N4 170.5(4) N2 C8 C9 N4 -9.9(6) N3 N5 C10 N4 0.0(6) C9 N4 C10 N5 0.1(5) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 30654784