#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2011143.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_occupancy _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_ _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_bond_atom_site_label_1 _geom_bond_atom_site_label_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_ _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