#------------------------------------------------------------------------------ #$Date: 2010-01-30 13:59:17 +0000 (Sat, 30 Jan 2010) $ #$Revision: 966 $ #$URL: svn://www.crystallography.net/cod/cif/2/2206663.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_2206663 loop_ _publ_author_name 'Zhang, Shu-Ping' 'Liu, Zhao-Di' 'Yang, Song' 'Qiu, Xiao-Yang' 'Shao, Si-Chang' _publ_section_title ; 4-(4-Ethoxyphenyl)-3,5-di-2-pyridyl-4H-1,2,4-triazole ; _journal_coeditor_code CI6635 _journal_issue 9 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o3108 _journal_page_last o3109 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C20 H17 N5 O' _chemical_formula_moiety 'C20 H17 N5 O' _chemical_formula_sum 'C20 H17 N5 O' _chemical_formula_weight 343.39 _chemical_name_systematic ; 4-(4-ethoxyphenyl)-3,5-di-2-pyridyl-4H-1,2,4-triazole ; _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 104.657(9) _cell_angle_beta 92.706(8) _cell_angle_gamma 115.133(8) _cell_formula_units_Z 2 _cell_length_a 8.094(5) _cell_length_b 9.468(6) _cell_length_c 13.152(8) _cell_measurement_reflns_used 1021 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.3 _cell_measurement_theta_min 4.6 _cell_volume 868.9(9) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_molecular_graphics 'SHELXTL (Sheldrick, 1997b)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997a)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997a)' _diffrn_ambient_temperature 566(2) _diffrn_measured_fraction_theta_full 0.974 _diffrn_measured_fraction_theta_max 0.974 _diffrn_measurement_device_type 'Bruker SMART CCD 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 0.0333 _diffrn_reflns_av_sigmaI/netI 0.0525 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 4239 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 1.63 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_T_max 0.9915 _exptl_absorpt_correction_T_min 0.9831 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour white _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 360 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.230 _refine_diff_density_min -0.249 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.873 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 235 _refine_ls_number_reflns 2989 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.873 _refine_ls_R_factor_all 0.0745 _refine_ls_R_factor_gt 0.0457 _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^)+(0.0621P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1097 _refine_ls_wR_factor_ref 0.1203 _reflns_number_gt 1790 _reflns_number_total 2989 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ci6635.cif loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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' 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 O1 0.66355(19) -0.11441(17) 0.46033(11) 0.0626(4) Uani d . 1 O N1 0.9530(2) 0.2764(2) 0.01317(14) 0.0627(5) Uani d . 1 N N2 0.8545(3) 0.1194(2) -0.05370(13) 0.0625(5) Uani d . 1 N N3 0.8220(2) 0.11639(19) 0.11082(12) 0.0501(4) Uani d . 1 N N4 1.0429(3) 0.4075(2) 0.29918(14) 0.0689(5) Uani d . 1 N N5 0.5095(3) -0.2215(3) 0.01274(15) 0.0767(6) Uani d . 1 N C1 0.7765(3) 0.0256(3) 0.00556(15) 0.0526(5) Uani d . 1 C C2 0.9332(3) 0.2732(3) 0.11086(16) 0.0531(5) Uani d . 1 C C3 0.6516(3) -0.1499(3) -0.03908(16) 0.0534(5) Uani d . 1 C C4 0.6805(3) -0.2296(3) -0.13034(16) 0.0563(5) Uani d . 1 C H4A 0.7785 -0.1760 -0.1626 0.068 Uiso calc R 1 H C5 0.5649(4) -0.3884(4) -0.1741(2) 0.0897(8) Uani d . 1 C H5 0.5834 -0.4452 -0.2377 0.108 Uiso calc R 1 H C6 0.4201(4) -0.4701(3) -0.1279(2) 0.0852(8) Uani d . 1 C H6A 0.3415 -0.5809 -0.1594 0.102 Uiso calc R 1 H C7 0.3935(3) -0.3855(3) -0.0348(2) 0.0747(7) Uani d . 1 C H7A 0.2954 -0.4395 -0.0028 0.090 Uiso calc R 1 H C8 1.0179(3) 0.4220(3) 0.20219(16) 0.0537(5) Uani d . 1 C C9 1.0713(3) 0.5710(3) 0.18406(18) 0.0631(6) Uani d . 1 C H9A 1.0507 0.5759 0.1151 0.076 Uiso calc R 1 H C10 1.1542(3) 0.7111(3) 0.2675(2) 0.0728(7) Uani d . 1 C H10A 1.1923 0.8127 0.2565 0.087 Uiso calc R 1 H C11 1.1804(3) 0.6995(3) 0.3676(2) 0.0784(7) Uani d . 1 C H11A 1.2359 0.7928 0.4265 0.094 Uiso calc R 1 H C13 0.7819(3) 0.0554(2) 0.20103(14) 0.0469(5) Uani d . 1 C C14 0.6592(3) 0.0847(2) 0.26154(16) 0.0551(5) Uani d . 1 C H14A 0.6011 0.1438 0.2442 0.066 Uiso calc R 1 H C15 0.6231(3) 0.0263(2) 0.34772(15) 0.0542(5) Uani d . 1 C H15A 0.5414 0.0469 0.3894 0.065 Uiso calc R 1 H C16 0.7080(3) -0.0632(2) 0.37258(15) 0.0479(5) Uani d . 1 C C17 0.8286(3) -0.0933(2) 0.31156(15) 0.0530(5) Uani d . 1 C H17A 0.8850 -0.1543 0.3280 0.064 Uiso calc R 1 H C18 0.8667(3) -0.0330(2) 0.22518(15) 0.0533(5) Uani d . 1 C H18A 0.9494 -0.0525 0.1839 0.064 Uiso calc R 1 H C12 1.1229(3) 0.5472(3) 0.37922(19) 0.0795(7) Uani d . 1 C H12A 1.1409 0.5404 0.4479 0.095 Uiso calc R 1 H C20 0.6652(4) -0.2565(3) 0.5833(2) 0.0917(9) Uani d . 1 C H20A 0.7107 -0.3265 0.6024 0.138 Uiso calc R 1 H H20B 0.5321 -0.3111 0.5689 0.138 Uiso calc R 1 H H20C 0.7076 -0.1570 0.6411 0.138 Uiso calc R 1 H C19 0.7355(3) -0.2176(3) 0.48579(18) 0.0712(7) Uani d . 1 C H19A 0.8699 -0.1620 0.4994 0.085 Uiso calc R 1 H H19B 0.6942 -0.3173 0.4269 0.085 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 O1 0.0800(10) 0.0748(10) 0.0537(9) 0.0433(8) 0.0211(7) 0.0368(8) N1 0.0793(13) 0.0692(13) 0.0494(11) 0.0362(11) 0.0180(10) 0.0279(10) N2 0.0816(13) 0.0708(13) 0.0459(11) 0.0395(11) 0.0173(10) 0.0253(10) N3 0.0617(11) 0.0569(11) 0.0399(10) 0.0302(9) 0.0125(8) 0.0211(8) N4 0.0855(14) 0.0676(13) 0.0497(11) 0.0285(11) 0.0060(10) 0.0235(11) N5 0.0770(14) 0.0838(15) 0.0704(14) 0.0357(12) 0.0098(11) 0.0270(12) C1 0.0663(14) 0.0665(15) 0.0397(12) 0.0398(12) 0.0142(10) 0.0215(11) C2 0.0643(14) 0.0605(14) 0.0472(13) 0.0332(12) 0.0151(10) 0.0268(11) C3 0.0628(14) 0.0659(15) 0.0431(13) 0.0356(12) 0.0097(10) 0.0236(11) C4 0.0687(15) 0.0667(15) 0.0398(12) 0.0364(13) 0.0143(11) 0.0149(11) C5 0.113(2) 0.120(3) 0.0548(16) 0.076(2) 0.0141(17) 0.0158(18) C6 0.102(2) 0.0655(17) 0.0740(19) 0.0407(16) -0.0174(17) -0.0005(15) C7 0.0611(15) 0.0703(17) 0.0846(19) 0.0197(14) 0.0035(14) 0.0298(15) C8 0.0576(13) 0.0625(15) 0.0494(13) 0.0285(11) 0.0145(10) 0.0273(12) C9 0.0663(15) 0.0650(15) 0.0589(14) 0.0257(12) 0.0100(12) 0.0275(13) C10 0.0753(16) 0.0630(16) 0.0792(18) 0.0280(13) 0.0095(14) 0.0267(15) C11 0.0846(18) 0.0657(17) 0.0693(17) 0.0257(14) 0.0042(14) 0.0117(14) C13 0.0567(12) 0.0510(12) 0.0374(11) 0.0259(10) 0.0090(9) 0.0174(9) C14 0.0632(13) 0.0673(14) 0.0505(13) 0.0387(12) 0.0144(11) 0.0260(11) C15 0.0612(13) 0.0672(14) 0.0479(12) 0.0361(12) 0.0178(10) 0.0252(11) C16 0.0552(12) 0.0501(12) 0.0406(11) 0.0225(10) 0.0091(10) 0.0192(10) C17 0.0676(14) 0.0548(13) 0.0473(12) 0.0345(11) 0.0109(10) 0.0203(10) C18 0.0650(13) 0.0611(13) 0.0437(12) 0.0355(11) 0.0158(10) 0.0185(10) C12 0.0923(19) 0.0841(19) 0.0514(15) 0.0303(15) 0.0035(13) 0.0219(15) C20 0.124(2) 0.113(2) 0.0829(18) 0.0724(19) 0.0363(17) 0.0663(17) C19 0.0937(17) 0.0779(16) 0.0640(15) 0.0485(14) 0.0173(13) 0.0388(13) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C16 1.368(2) O1 C19 1.427(2) N1 C2 1.309(2) N1 N2 1.373(2) N2 C1 1.310(2) N3 C1 1.368(2) N3 C2 1.370(2) N3 C13 1.439(2) N4 C8 1.332(2) N4 C12 1.334(3) N5 C3 1.375(3) N5 C7 1.378(3) C1 C3 1.467(3) C2 C8 1.464(3) C3 C4 1.335(3) C4 C5 1.335(3) C4 H4A 0.93 C5 C6 1.369(3) C5 H5 0.93 C6 C7 1.365(4) C6 H6A 0.93 C7 H7A 0.93 C8 C9 1.377(3) C9 C10 1.361(3) C9 H9A 0.93 C10 C11 1.363(3) C10 H10A 0.93 C11 C12 1.367(3) C11 H11A 0.93 C13 C18 1.369(2) C13 C14 1.376(3) C14 C15 1.374(3) C14 H14A 0.93 C15 C16 1.382(3) C15 H15A 0.93 C16 C17 1.369(3) C17 C18 1.387(3) C17 H17A 0.93 C18 H18A 0.93 C12 H12A 0.93 C20 C19 1.494(3) C20 H20A 0.96 C20 H20B 0.96 C20 H20C 0.96 C19 H19A 0.97 C19 H19B 0.97 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C16 O1 C19 118.19(16) C2 N1 N2 107.82(16) C1 N2 N1 107.39(17) C1 N3 C2 104.47(16) C1 N3 C13 126.82(17) C2 N3 C13 128.20(16) C8 N4 C12 115.90(19) C3 N5 C7 116.1(2) N2 C1 N3 110.31(19) N2 C1 C3 122.95(18) N3 C1 C3 126.67(17) N1 C2 N3 110.01(18) N1 C2 C8 121.92(19) N3 C2 C8 128.05(17) C4 C3 N5 123.9(2) C4 C3 C1 117.2(2) N5 C3 C1 118.81(19) C3 C4 C5 118.2(2) C3 C4 H4A 120.9 C5 C4 H4A 120.9 C4 C5 C6 122.0(2) C4 C5 H5 119.0 C6 C5 H5 119.0 C7 C6 C5 118.6(3) C7 C6 H6A 120.7 C5 C6 H6A 120.7 C6 C7 N5 121.2(2) C6 C7 H7A 119.4 N5 C7 H7A 119.4 N4 C8 C9 122.8(2) N4 C8 C2 118.46(18) C9 C8 C2 118.71(19) C10 C9 C8 119.6(2) C10 C9 H9A 120.2 C8 C9 H9A 120.2 C9 C10 C11 118.7(2) C9 C10 H10A 120.7 C11 C10 H10A 120.7 C10 C11 C12 118.2(2) C10 C11 H11A 120.9 C12 C11 H11A 120.9 C18 C13 C14 120.64(17) C18 C13 N3 118.98(17) C14 C13 N3 120.37(17) C15 C14 C13 119.67(19) C15 C14 H14A 120.2 C13 C14 H14A 120.2 C14 C15 C16 120.0(2) C14 C15 H15A 120.0 C16 C15 H15A 120.0 O1 C16 C17 124.62(18) O1 C16 C15 115.32(18) C17 C16 C15 120.05(17) C16 C17 C18 119.98(19) C16 C17 H17A 120.0 C18 C17 H17A 120.0 C13 C18 C17 119.61(19) C13 C18 H18A 120.2 C17 C18 H18A 120.2 N4 C12 C11 124.7(2) N4 C12 H12A 117.6 C11 C12 H12A 117.6 C19 C20 H20A 109.5 C19 C20 H20B 109.5 H20A C20 H20B 109.5 C19 C20 H20C 109.5 H20A C20 H20C 109.5 H20B C20 H20C 109.5 O1 C19 C20 107.36(19) O1 C19 H19A 110.2 C20 C19 H19A 110.2 O1 C19 H19B 110.2 C20 C19 H19B 110.2 H19A C19 H19B 108.5 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 C9 H9A N1 2_765 0.93 2.46 3.308(4) 152 yes C18 H18A N2 2_755 0.93 2.53 3.459(4) 174 yes _cod_database_code 2206663