#------------------------------------------------------------------------------ #$Date: 2013-08-29 18:37:19 +0300 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/20/48/2204852.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_2204852 loop_ _publ_author_name 'Fu-You Pan' 'Jian-Guo Yang' _publ_section_title ; 3-[(2-Chlorophenyl)methylenehydrazinocarbonyl]-1H-1,2,4-triazole ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o63 _journal_page_last o64 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C10 H8 Cl N5 O' _chemical_formula_moiety 'C10 H8 Cl N5 O' _chemical_formula_sum 'C10 H8 Cl N5 O' _chemical_formula_weight 249.66 _chemical_name_systematic ; 3-[(2-Chlorophenyl)methylenehydrazinocarbonyl]-1H-1,2,4-triazole ; _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 98.607(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 19.395(3) _cell_length_b 7.5786(11) _cell_length_c 7.3930(11) _cell_measurement_reflns_used 1143 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 45.804 _cell_measurement_theta_min 5.780 _cell_volume 1074.4(3) _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_collection 'SMART (Bruker, 2002)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Bruker, 2002)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker APEX area-detector' _diffrn_measurement_method '\f and \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 0.0774 _diffrn_reflns_av_sigmaI/netI 0.0689 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 6121 _diffrn_reflns_theta_full 27.00 _diffrn_reflns_theta_max 27.00 _diffrn_reflns_theta_min 2.12 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.346 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.508 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.543 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 512 _exptl_crystal_size_max 0.516 _exptl_crystal_size_mid 0.178 _exptl_crystal_size_min 0.075 _refine_diff_density_max 0.298 _refine_diff_density_min -0.366 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.995 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 186 _refine_ls_number_reflns 2340 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.995 _refine_ls_R_factor_all 0.0950 _refine_ls_R_factor_gt 0.0597 _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^)+(0.0565P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1228 _refine_ls_wR_factor_ref 0.1378 _reflns_number_gt 1504 _reflns_number_total 2340 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ci6470.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_database_code 2204852 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_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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_occupancy _atom_site_type_symbol Cl 0.06964(4) 0.80783(11) 1.09174(13) 0.0592(3) Uani d 1 Cl O1 0.40624(11) 0.7657(2) 0.8501(3) 0.0518(6) Uani d 1 O N1 0.31071(12) 0.8909(3) 0.9416(4) 0.0383(6) Uani d 1 N N2 0.27928(12) 0.7366(3) 0.9749(3) 0.0385(6) Uani d 1 N N3 0.36185(12) 1.2233(3) 0.8900(4) 0.0406(6) Uani d 1 N N4 0.45806(12) 1.1043(3) 0.8001(3) 0.0406(6) Uani d 1 N N5 0.46123(14) 1.2806(3) 0.7988(4) 0.0451(7) Uani d 1 N C1 0.37342(14) 0.8946(3) 0.8812(4) 0.0359(7) Uani d 1 C C2 0.39777(14) 1.0761(3) 0.8570(4) 0.0337(7) Uani d 1 C C3 0.40527(17) 1.3496(4) 0.8505(4) 0.0430(8) Uani d 1 C C4 0.21902(16) 0.7507(4) 1.0188(4) 0.0397(7) Uani d 1 C C5 0.18128(15) 0.5955(4) 1.0691(4) 0.0365(7) Uani d 1 C C6 0.21322(18) 0.4301(4) 1.0888(4) 0.0436(8) Uani d 1 C C7 0.1801(2) 0.2863(4) 1.1471(5) 0.0535(9) Uani d 1 C C8 0.1126(2) 0.3030(5) 1.1854(5) 0.0585(10) Uani d 1 C C9 0.07951(18) 0.4613(5) 1.1657(4) 0.0516(9) Uani d 1 C C10 0.11327(16) 0.6066(4) 1.1083(4) 0.0410(7) Uani d 1 C H1 0.2897(14) 0.982(4) 0.952(4) 0.041(9) Uiso d 1 H H3 0.3950(13) 1.464(3) 0.856(3) 0.031(7) Uiso d 1 H H4 0.1969(14) 0.868(3) 1.023(4) 0.044(8) Uiso d 1 H H5 0.498(2) 1.348(4) 0.764(5) 0.091(13) Uiso d 1 H H6 0.2583(16) 0.424(4) 1.069(4) 0.056(10) Uiso d 1 H H7 0.2060(18) 0.174(4) 1.164(5) 0.068(11) Uiso d 1 H H8 0.0897(16) 0.210(4) 1.222(4) 0.053(9) Uiso d 1 H H9 0.0337(15) 0.478(4) 1.191(4) 0.049(9) 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 Cl 0.0462(5) 0.0639(6) 0.0727(7) 0.0065(4) 0.0263(5) 0.0038(4) O1 0.0425(13) 0.0275(10) 0.0921(18) 0.0037(9) 0.0322(13) 0.0001(11) N1 0.0317(14) 0.0258(13) 0.0618(18) -0.0007(11) 0.0216(13) 0.0023(12) N2 0.0362(14) 0.0320(12) 0.0493(16) -0.0072(10) 0.0132(12) 0.0034(11) N3 0.0430(15) 0.0259(12) 0.0561(17) 0.0006(10) 0.0177(13) 0.0007(11) N4 0.0327(14) 0.0348(13) 0.0576(17) -0.0049(10) 0.0175(12) 0.0040(12) N5 0.0432(16) 0.0350(14) 0.0588(18) -0.0139(12) 0.0130(14) 0.0097(13) C1 0.0313(16) 0.0341(15) 0.0438(18) -0.0022(12) 0.0105(14) 0.0014(13) C2 0.0338(16) 0.0293(14) 0.0400(17) 0.0004(12) 0.0117(13) 0.0003(12) C3 0.052(2) 0.0229(15) 0.055(2) -0.0006(14) 0.0085(16) 0.0028(14) C4 0.0398(18) 0.0348(16) 0.0472(19) -0.0028(13) 0.0156(15) 0.0022(14) C5 0.0366(17) 0.0417(16) 0.0327(16) -0.0120(13) 0.0099(13) 0.0009(13) C6 0.044(2) 0.0443(18) 0.0437(19) -0.0076(14) 0.0109(16) 0.0005(14) C7 0.067(2) 0.0395(19) 0.056(2) -0.0147(17) 0.0156(19) -0.0009(17) C8 0.073(3) 0.050(2) 0.055(2) -0.028(2) 0.019(2) 0.0028(18) C9 0.045(2) 0.066(2) 0.049(2) -0.0205(17) 0.0205(17) -0.0022(17) C10 0.0374(17) 0.0475(17) 0.0393(18) -0.0028(14) 0.0099(14) -0.0001(14) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl C10 1.740(3) ? O1 C1 1.207(3) yes N1 C1 1.357(3) yes N1 N2 1.358(3) yes N1 H1 0.81(3) ? N2 C4 1.263(4) yes N3 C3 1.336(4) yes N3 C2 1.357(3) yes N4 C2 1.318(3) yes N4 N5 1.337(3) yes N5 C3 1.312(4) yes N5 H5 0.95(4) ? C1 C2 1.473(3) ? C3 H3 0.89(2) ? C4 C5 1.463(4) ? C4 H4 0.99(3) ? C5 C10 1.395(4) ? C5 C6 1.396(4) ? C6 C7 1.366(4) ? C6 H6 0.91(3) ? C7 C8 1.387(5) ? C7 H7 0.98(3) ? C8 C9 1.358(5) ? C8 H8 0.89(3) ? C9 C10 1.380(4) ? C9 H9 0.94(3) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C1 N1 N2 121.8(2) C1 N1 H1 120(2) N2 N1 H1 118(2) C4 N2 N1 115.6(2) C3 N3 C2 101.1(2) C2 N4 N5 102.0(2) C3 N5 N4 110.8(2) C3 N5 H5 124(2) N4 N5 H5 125(2) O1 C1 N1 124.7(2) O1 C1 C2 123.0(2) N1 C1 C2 112.3(2) N4 C2 N3 115.3(2) N4 C2 C1 120.4(2) N3 C2 C1 124.3(2) N5 C3 N3 110.7(3) N5 C3 H3 126.8(16) N3 C3 H3 122.4(16) N2 C4 C5 121.0(3) N2 C4 H4 120.4(16) C5 C4 H4 118.6(15) C10 C5 C6 116.8(3) C10 C5 C4 121.9(3) C6 C5 C4 121.1(3) C7 C6 C5 121.8(3) C7 C6 H6 121.5(18) C5 C6 H6 116.6(18) C6 C7 C8 119.6(3) C6 C7 H7 118.3(19) C8 C7 H7 122.1(19) C9 C8 C7 120.2(3) C9 C8 H8 119(2) C7 C8 H8 121(2) C8 C9 C10 120.0(3) C8 C9 H9 122.7(18) C10 C9 H9 117.3(18) C9 C10 C5 121.5(3) C9 C10 Cl 118.2(2) C5 C10 Cl 120.2(2) 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 _geom_torsion_publ_flag C1 N1 N2 C4 -175.4(3) yes C2 N4 N5 C3 -0.6(3) ? N2 N1 C1 O1 0.8(5) ? N2 N1 C1 C2 -179.2(3) ? N5 N4 C2 N3 0.7(3) ? N5 N4 C2 C1 -179.2(3) ? C3 N3 C2 N4 -0.6(4) ? C3 N3 C2 C1 179.3(3) ? O1 C1 C2 N4 -0.4(5) ? N1 C1 C2 N4 179.6(3) ? O1 C1 C2 N3 179.7(3) ? N1 C1 C2 N3 -0.3(4) ? N4 N5 C3 N3 0.3(4) ? C2 N3 C3 N5 0.1(4) ? N1 N2 C4 C5 -176.2(3) yes N2 C4 C5 C10 -176.4(3) yes N2 C4 C5 C6 6.8(5) yes C10 C5 C6 C7 -1.3(5) ? C4 C5 C6 C7 175.7(3) ? C5 C6 C7 C8 1.0(5) ? C6 C7 C8 C9 -0.2(6) ? C7 C8 C9 C10 -0.3(5) ? C8 C9 C10 C5 0.0(5) ? C8 C9 C10 Cl -178.1(3) ? C6 C5 C10 C9 0.7(4) ? C4 C5 C10 C9 -176.3(3) ? C6 C5 C10 Cl 178.8(2) ? C4 C5 C10 Cl 1.9(4) ? 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 O1 2_656 0.95(4) 2.23(4) 2.946(3) 131(3) N5 H5 N4 2_656 0.95(4) 2.20(4) 3.057(3) 150(3) _cod_database_fobs_code 2204852