#------------------------------------------------------------------------------ #$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/11/2011143.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_2011143 loop_ _publ_author_name 'Zhu, Dun-Ru' 'Xu, Yan' 'Zhang, Yong' 'Wang, Tian-Wei' 'You, Xiao-Zeng' _publ_section_title ; 4-Phenyl-3,5-bis(2-pyridyl)-4H-1,2,4-triazole ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 895 _journal_page_last 896 _journal_volume 56 _journal_year 2000 _chemical_formula_sum 'C18 H13 N5' _chemical_formula_weight 299.33 _chemical_name_systematic ; 4-Phenyl-3,5-bis(2-pyridyl)-4H-1,2,4-triazole ; _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' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 95.188(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 5.9217(8) _cell_length_b 15.3265(15) _cell_length_c 15.9824(14) _cell_measurement_reflns_used 57 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 12.50 _cell_measurement_theta_min 6.73 _cell_volume 1444.6(3) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens, 1994)' _computing_data_reduction XSCANS _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full .999 _diffrn_measured_fraction_theta_max .999 _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method 2\q/\w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .028 _diffrn_reflns_av_sigmaI/netI .0507 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 3576 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 1.84 _diffrn_standards_decay_% 6.81 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .087 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.376 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 624 _exptl_crystal_size_max .58 _exptl_crystal_size_mid .25 _exptl_crystal_size_min .22 _refine_diff_density_max .13 _refine_diff_density_min -.14 _refine_ls_extinction_coef .0124(18) _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 261 _refine_ls_number_reflns 2531 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.006 _refine_ls_R_factor_all .071 _refine_ls_R_factor_gt .042 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0443P)^2^+0.1874P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .109 _reflns_number_gt 1800 _reflns_number_total 2531 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file na1465.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_database_code 2011143 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 N1 .3306(3) .84246(11) .49567(10) .0482(5) Uani d . 1 . . N N2 -.2020(3) .60687(11) .69336(10) .0496(5) Uani d . 1 . . N N3 .1859(3) .86351(12) .70647(10) .0469(4) Uani d . 1 . . N N4 .0210(3) .81881(12) .74456(10) .0470(4) Uani d . 1 . . N N5 .0770(2) .75137(10) .62623(9) .0358(4) Uani d . 1 . . N C1 .7260(4) .92555(15) .55923(15) .0528(6) Uani d . 1 . . C C2 .6804(4) .91365(15) .47415(15) .0537(6) Uani d . 1 . . C C3 .4824(4) .87269(15) .44526(14) .0526(6) Uani d . 1 . . C C4 .5745(4) .89531(13) .61220(14) .0454(5) Uani d . 1 . . C C5 .3807(3) .85378(12) .57871(12) .0392(5) Uani d . 1 . . C C6 .2171(3) .82263(13) .63602(11) .0388(5) Uani d . 1 . . C C7 -.0421(3) .75221(13) .69594(11) .0386(5) Uani d . 1 . . C C8 -.2166(3) .69029(13) .71807(11) .0394(5) Uani d . 1 . . C C9 -.3842(4) .71994(15) .76649(13) .0474(5) Uani d . 1 . . C C10 -.3624(4) .55241(16) .71603(14) .0552(6) Uani d . 1 . . C C11 -.5364(4) .57694(17) .76219(14) .0559(6) Uani d . 1 . . C C12 -.5461(4) .66227(17) .78824(15) .0566(6) Uani d . 1 . . C C13 .0534(3) .69175(12) .55562(11) .0363(5) Uani d . 1 . . C C14 .2325(4) .63951(14) .53913(13) .0447(5) Uani d . 1 . . C C15 .2099(4) .58560(15) .46972(14) .0566(6) Uani d . 1 . . C C16 .0108(5) .58402(16) .41804(14) .0575(6) Uani d . 1 . . C C17 -.1670(4) .63640(15) .43552(13) .0524(6) Uani d . 1 . . C C18 -.1470(4) .69085(14) .50468(12) .0430(5) Uani d . 1 . . C H14 .372(4) .6405(13) .5774(12) .048(6) Uiso d . 1 . . H H12 -.661(4) .6824(14) .8235(13) .059(6) Uiso d . 1 . . H H18 -.269(3) .7255(13) .5178(12) .045(6) Uiso d . 1 . . H H10 -.351(4) .4903(15) .6970(13) .058(6) Uiso d . 1 . . H H17 -.306(4) .6379(15) .3991(14) .069(7) Uiso d . 1 . . H H3 .442(4) .8658(16) .3838(15) .074(7) Uiso d . 1 . . H H1 .864(4) .9566(15) .5813(13) .061(7) Uiso d . 1 . . H H11 -.652(4) .5338(16) .7744(14) .069(7) Uiso d . 1 . . H H2 .783(4) .9357(16) .4375(14) .071(7) Uiso d . 1 . . H H15 .341(5) .5464(17) .4575(15) .081(8) Uiso d . 1 . . H H16 -.006(4) .5442(16) .3670(15) .077(7) Uiso d . 1 . . H H4 .602(4) .9031(14) .6713(14) .057(6) Uiso d . 1 . . H H9 -.385(3) .7822(15) .7848(12) .050(6) 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 N1 .0484(10) .0495(11) .0466(10) -.0039(9) .0031(8) .0007(8) N2 .0590(12) .0474(11) .0437(10) .0009(10) .0123(9) -.0011(8) N3 .0473(10) .0476(10) .0454(10) -.0006(9) .0024(8) -.0080(8) N4 .0477(10) .0514(10) .0423(9) .0011(9) .0059(8) -.0072(8) N5 .0357(9) .0390(9) .0328(8) .0019(8) .0026(7) -.0023(7) C1 .0411(13) .0463(13) .0705(15) -.0023(11) .0015(12) .0002(11) C2 .0507(14) .0475(13) .0651(15) -.0026(12) .0171(12) .0022(11) C3 .0555(14) .0556(14) .0473(13) -.0034(12) .0082(11) .0008(11) C4 .0443(13) .0418(11) .0486(13) .0011(10) -.0040(10) .0015(10) C5 .0399(11) .0347(10) .0428(10) .0039(9) .0025(9) .0004(9) C6 .0362(10) .0390(11) .0402(10) .0023(9) -.0015(8) -.0015(9) C7 .0379(11) .0435(11) .0341(10) .0082(10) .0016(8) -.0006(9) C8 .0413(11) .0444(12) .0324(10) .0053(10) .0020(8) .0020(8) C9 .0486(13) .0461(13) .0491(12) .0084(11) .0137(10) .0053(10) C10 .0711(16) .0463(13) .0497(12) -.0042(13) .0134(12) .0009(11) C11 .0573(15) .0600(15) .0515(13) -.0050(13) .0113(11) .0118(12) C12 .0548(14) .0631(16) .0550(13) .0132(13) .0210(12) .0135(11) C13 .0406(11) .0340(10) .0345(9) -.0010(9) .0057(8) .0011(8) C14 .0430(12) .0471(12) .0443(11) .0073(10) .0057(10) -.0006(10) C15 .0628(15) .0531(14) .0567(14) .0088(13) .0200(12) -.0084(11) C16 .0726(17) .0551(14) .0463(13) -.0099(13) .0144(12) -.0138(11) C17 .0549(14) .0585(14) .0427(12) -.0116(12) -.0025(11) -.0009(11) C18 .0397(12) .0447(12) .0441(11) .0011(11) .0020(9) -.0004(10) 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 N1 C3 . 1.343(3) yes N1 C5 . 1.345(2) yes N2 C10 . 1.339(3) yes N2 C8 . 1.343(3) yes N3 C6 . 1.316(2) yes N3 N4 . 1.378(2) yes N4 C7 . 1.316(2) yes N5 C7 . 1.372(2) yes N5 C6 . 1.372(2) yes N5 C13 . 1.449(2) yes C1 C4 . 1.369(3) ? C1 C2 . 1.374(3) ? C2 C3 . 1.373(3) ? C4 C5 . 1.378(3) ? C5 C6 . 1.472(3) ? C7 C8 . 1.470(3) ? C8 C9 . 1.389(3) ? C9 C12 . 1.372(3) ? C10 C11 . 1.373(3) ? C11 C12 . 1.375(3) ? C13 C14 . 1.373(3) ? C13 C18 . 1.377(3) ? C14 C15 . 1.380(3) ? C15 C16 . 1.377(3) ? C16 C17 . 1.373(3) ? C17 C18 . 1.381(3) ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .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 _geom_angle_publ_flag C3 N1 C5 116.6(2) ? C10 N2 C8 116.6(2) ? C6 N3 N4 107.5(2) yes C7 N4 N3 107.4(2) yes C7 N5 C6 104.5(2) yes C7 N5 C13 128.2(2) ? C6 N5 C13 127.3(2) ? C4 C1 C2 119.1(2) ? C3 C2 C1 118.6(2) ? N1 C3 C2 123.6(2) ? C1 C4 C5 119.1(2) ? N1 C5 C4 123.0(2) ? N1 C5 C6 118.3(2) ? C4 C5 C6 118.7(2) ? N3 C6 N5 110.3(2) yes N3 C6 C5 122.0(2) yes N5 C6 C5 127.8(2) yes N4 C7 N5 110.3(2) yes N4 C7 C8 121.8(2) yes N5 C7 C8 127.9(2) ? N2 C8 C9 122.9(2) ? N2 C8 C7 118.6(2) ? C9 C8 C7 118.4(2) ? C12 C9 C8 118.8(2) ? N2 C10 C11 124.0(2) ? C10 C11 C12 118.5(2) ? C9 C12 C11 119.1(2) ? C14 C13 C18 121.3(2) ? C14 C13 N5 119.7(2) ? C18 C13 N5 119.0(2) ? C13 C14 C15 118.9(2) ? C16 C15 C14 120.5(2) ? C17 C16 C15 119.9(2) ? C16 C17 C18 120.3(2) ? C13 C18 C17 119.1(2) ? 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 C4 H4 N3 . .95(2) 2.65(2) 2.904(3) 96(2) yes C9 H9 N4 . 1.00(2) 2.61(2) 2.886(3) 96.0(10) yes C17 H17 N4 4_575 .96(2) 2.67(2) 3.490(3) 143(2) yes C11 H11 N3 2_446 .98(3) 2.64(3) 3.437(3) 138(2) yes _cod_database_fobs_code 2011143 _journal_paper_doi 10.1107/S0108270100005473