#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/49/2204942.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_2204942 loop_ _publ_author_name 'Zhang, Shu-Ping' 'You, Zhong-Lu' 'Shao, Si-Chang' 'Zhu, Hai-Liang' _publ_section_title ; 4-(4-Isopropylphenyl)-3,5-di-2-pyridyl-4H-1,2,4-triazole ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o8 _journal_page_last o9 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C21 H19 N5' _chemical_formula_moiety 'C21 H19 N5' _chemical_formula_sum 'C21 H19 N5' _chemical_formula_weight 341.41 _chemical_name_systematic ; 4-(4-Isopropylphenyl)-3,5-di-2-pyridyl-4H-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 107.580(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.7040(10) _cell_length_b 19.935(2) _cell_length_c 8.1810(10) _cell_measurement_reflns_used 1463 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 21.18 _cell_measurement_theta_min 2.88 _cell_volume 1819.6(3) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1997)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.986 _diffrn_measured_fraction_theta_max 0.986 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method \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 0.0344 _diffrn_reflns_av_sigmaI/netI 0.0496 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_number 7778 _diffrn_reflns_theta_full 25.50 _diffrn_reflns_theta_max 25.50 _diffrn_reflns_theta_min 1.83 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_correction_T_min 0.982 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.246 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 720 _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.193 _refine_diff_density_min -0.155 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 237 _refine_ls_number_reflns 3336 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.002 _refine_ls_R_factor_all 0.0803 _refine_ls_R_factor_gt 0.0500 _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^)+(0.0617P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1114 _refine_ls_wR_factor_ref 0.1263 _reflns_number_gt 2245 _reflns_number_total 3336 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ob6447.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _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_cell_volume 1819.7(3) _cod_database_code 2204942 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 N1 0.33639(14) 0.48210(8) 0.3351(2) 0.0491(5) Uani d . 1 N N2 0.06223(13) 0.39609(8) 0.1856(2) 0.0481(5) Uani d . 1 N N3 0.04281(13) 0.32777(8) 0.1859(2) 0.0482(5) Uani d . 1 N N4 0.24100(14) 0.19918(8) 0.1363(2) 0.0469(4) Uani d . 1 N N5 0.23361(12) 0.34461(7) 0.21519(19) 0.0358(4) Uani d . 1 N C1 0.23198(15) 0.47184(9) 0.2130(2) 0.0387(5) Uani d . 1 C C2 0.17375(17) 0.52152(10) 0.1013(3) 0.0463(5) Uani d . 1 C H2 0.1014 0.5125 0.0182 0.056 Uiso calc R 1 H C3 0.22357(19) 0.58447(10) 0.1139(3) 0.0522(6) Uani d . 1 C H3 0.1848 0.6188 0.0413 0.063 Uiso calc R 1 H C4 0.33144(19) 0.59550(11) 0.2355(3) 0.0550(6) Uani d . 1 C H4 0.3685 0.6372 0.2455 0.066 Uiso calc R 1 H C5 0.38387(19) 0.54358(11) 0.3425(3) 0.0565(6) Uani d . 1 C H5 0.4569 0.5516 0.4253 0.068 Uiso calc R 1 H C6 0.17627(15) 0.40498(9) 0.2038(2) 0.0380(5) Uani d . 1 C C7 0.14581(15) 0.29796(9) 0.2035(2) 0.0375(5) Uani d . 1 C C8 0.15823(15) 0.22444(10) 0.2014(2) 0.0395(5) Uani d . 1 C C9 0.08093(17) 0.18484(10) 0.2573(3) 0.0501(5) Uani d . 1 C H9 0.0257 0.2042 0.3043 0.060 Uiso calc R 1 H C10 0.0865(2) 0.11667(12) 0.2428(3) 0.0626(6) Uani d . 1 C H10 0.0343 0.0890 0.2779 0.075 Uiso calc R 1 H C11 0.1704(2) 0.08980(11) 0.1755(3) 0.0629(6) Uani d . 1 C H11 0.1760 0.0437 0.1630 0.075 Uiso calc R 1 H C12 0.2458(2) 0.13272(11) 0.1271(3) 0.0550(6) Uani d . 1 C H12 0.3042 0.1141 0.0850 0.066 Uiso calc R 1 H C13 0.35922(15) 0.33573(9) 0.2325(2) 0.0344(4) Uani d . 1 C C14 0.43403(15) 0.30263(9) 0.3705(2) 0.0386(5) Uani d . 1 C H14 0.4039 0.2829 0.4520 0.046 Uiso calc R 1 H C15 0.55490(15) 0.29904(9) 0.3867(3) 0.0404(5) Uani d . 1 C H15 0.6055 0.2761 0.4796 0.048 Uiso calc R 1 H C16 0.60298(16) 0.32859(9) 0.2686(3) 0.0391(5) Uani d . 1 C C17 0.52392(17) 0.36000(10) 0.1301(3) 0.0484(5) Uani d . 1 C H17 0.5534 0.3797 0.0479 0.058 Uiso calc R 1 H C18 0.40303(17) 0.36325(10) 0.1091(3) 0.0460(5) Uani d . 1 C H18 0.3515 0.3838 0.0128 0.055 Uiso calc R 1 H C19 0.73650(17) 0.33113(10) 0.2898(3) 0.0474(5) Uani d . 1 C H19 0.7454 0.3231 0.1761 0.057 Uiso calc R 1 H C20 0.81032(18) 0.27857(12) 0.4070(4) 0.0728(8) Uani d . 1 C H20A 0.8060 0.2853 0.5211 0.109 Uiso calc R 1 H H20B 0.8922 0.2820 0.4073 0.109 Uiso calc R 1 H H20C 0.7799 0.2349 0.3673 0.109 Uiso calc R 1 H C21 0.78588(19) 0.40087(11) 0.3439(4) 0.0728(8) Uani d . 1 C H21A 0.7388 0.4334 0.2658 0.109 Uiso calc R 1 H H21B 0.8675 0.4032 0.3426 0.109 Uiso calc R 1 H H21C 0.7826 0.4100 0.4576 0.109 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 N1 0.0434(9) 0.0388(10) 0.0578(11) -0.0004(8) 0.0044(8) 0.0015(8) N2 0.0368(9) 0.0414(10) 0.0648(12) 0.0035(8) 0.0133(8) 0.0036(8) N3 0.0370(9) 0.0418(10) 0.0639(12) -0.0007(8) 0.0123(8) 0.0018(8) N4 0.0539(10) 0.0410(10) 0.0471(11) 0.0035(8) 0.0172(8) -0.0014(8) N5 0.0316(8) 0.0337(9) 0.0415(10) 0.0028(7) 0.0101(7) 0.0023(7) C1 0.0343(10) 0.0373(11) 0.0456(12) 0.0033(8) 0.0135(9) 0.0007(9) C2 0.0418(11) 0.0420(12) 0.0516(13) 0.0051(9) 0.0090(9) 0.0039(10) C3 0.0605(13) 0.0389(12) 0.0558(14) 0.0070(10) 0.0155(11) 0.0106(10) C4 0.0597(13) 0.0396(13) 0.0642(15) -0.0067(11) 0.0166(11) 0.0026(11) C5 0.0517(12) 0.0448(14) 0.0629(15) -0.0044(11) 0.0023(10) -0.0018(11) C6 0.0326(10) 0.0365(12) 0.0422(12) 0.0046(8) 0.0073(8) 0.0037(9) C7 0.0312(10) 0.0397(12) 0.0406(12) -0.0017(8) 0.0092(8) 0.0010(9) C8 0.0363(10) 0.0390(12) 0.0386(12) -0.0001(9) 0.0044(8) 0.0016(9) C9 0.0428(11) 0.0496(14) 0.0569(14) -0.0009(10) 0.0136(10) 0.0064(10) C10 0.0624(14) 0.0472(14) 0.0735(18) -0.0118(12) 0.0135(12) 0.0109(12) C11 0.0787(16) 0.0336(13) 0.0663(16) -0.0029(12) 0.0067(13) -0.0007(11) C12 0.0701(15) 0.0421(14) 0.0525(14) 0.0098(11) 0.0180(11) -0.0025(10) C13 0.0325(9) 0.0318(10) 0.0403(11) -0.0003(8) 0.0132(8) -0.0023(8) C14 0.0393(10) 0.0366(11) 0.0426(12) 0.0025(9) 0.0164(9) 0.0079(9) C15 0.0340(10) 0.0380(11) 0.0466(12) 0.0056(8) 0.0083(9) 0.0057(9) C16 0.0366(10) 0.0325(11) 0.0508(13) -0.0007(8) 0.0171(9) -0.0028(9) C17 0.0478(12) 0.0528(13) 0.0513(14) 0.0016(10) 0.0250(10) 0.0103(11) C18 0.0436(11) 0.0517(13) 0.0419(12) 0.0063(9) 0.0118(9) 0.0087(10) C19 0.0404(11) 0.0458(13) 0.0604(14) -0.0011(9) 0.0219(10) -0.0026(10) C20 0.0397(12) 0.0680(16) 0.109(2) 0.0074(11) 0.0201(12) 0.0175(15) C21 0.0528(13) 0.0514(15) 0.121(2) -0.0144(11) 0.0366(14) -0.0143(14) 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' 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 C5 N1 C1 116.50(17) ? C6 N2 N3 107.21(14) yes C7 N3 N2 107.49(14) yes C12 N4 C8 116.50(17) ? C6 N5 C7 104.53(14) yes C6 N5 C13 125.34(14) ? C7 N5 C13 130.12(14) ? N1 C1 C2 122.74(18) ? N1 C1 C6 117.75(16) ? C2 C1 C6 119.47(17) ? C3 C2 C1 119.48(19) ? C3 C2 H2 120.3 ? C1 C2 H2 120.3 ? C4 C3 C2 118.58(19) ? C4 C3 H3 120.7 ? C2 C3 H3 120.7 ? C3 C4 C5 118.6(2) ? C3 C4 H4 120.7 ? C5 C4 H4 120.7 ? N1 C5 C4 124.1(2) ? N1 C5 H5 118.0 ? C4 C5 H5 118.0 ? N2 C6 N5 110.55(16) yes N2 C6 C1 123.19(16) ? N5 C6 C1 126.26(15) ? N3 C7 N5 110.22(16) yes N3 C7 C8 122.66(16) ? N5 C7 C8 127.05(15) ? N4 C8 C9 122.92(19) ? N4 C8 C7 117.72(16) ? C9 C8 C7 119.27(17) ? C10 C9 C8 119.2(2) ? C10 C9 H9 120.4 ? C8 C9 H9 120.4 ? C9 C10 C11 118.8(2) ? C9 C10 H10 120.6 ? C11 C10 H10 120.6 ? C12 C11 C10 118.3(2) ? C12 C11 H11 120.9 ? C10 C11 H11 120.9 ? N4 C12 C11 124.3(2) ? N4 C12 H12 117.8 ? C11 C12 H12 117.8 ? C14 C13 C18 120.60(16) ? C14 C13 N5 121.14(16) ? C18 C13 N5 118.23(16) ? C13 C14 C15 118.95(17) ? C13 C14 H14 120.5 ? C15 C14 H14 120.5 ? C14 C15 C16 122.00(18) ? C14 C15 H15 119.0 ? C16 C15 H15 119.0 ? C17 C16 C15 116.91(17) ? C17 C16 C19 119.38(17) ? C15 C16 C19 123.62(18) ? C18 C17 C16 122.30(18) ? C18 C17 H17 118.9 ? C16 C17 H17 118.9 ? C17 C18 C13 119.16(18) ? C17 C18 H18 120.4 ? C13 C18 H18 120.4 ? C20 C19 C21 110.91(19) ? C20 C19 C16 114.98(17) ? C21 C19 C16 110.57(16) ? C20 C19 H19 106.6 ? C21 C19 H19 106.6 ? C16 C19 H19 106.6 ? 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 ? C19 C21 H21A 109.5 ? C19 C21 H21B 109.5 ? H21A C21 H21B 109.5 ? C19 C21 H21C 109.5 ? H21A C21 H21C 109.5 ? H21B C21 H21C 109.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C5 1.339(2) ? N1 C1 1.340(2) ? N2 C6 1.310(2) yes N2 N3 1.381(2) yes N3 C7 1.312(2) yes N4 C12 1.329(2) ? N4 C8 1.337(2) ? N5 C6 1.367(2) yes N5 C7 1.368(2) yes N5 C13 1.445(2) ? C1 C2 1.380(3) ? C1 C6 1.476(2) ? C2 C3 1.374(3) ? C2 H2 0.9300 ? C3 C4 1.369(3) ? C3 H3 0.9300 ? C4 C5 1.375(3) ? C4 H4 0.9300 ? C5 H5 0.9300 ? C7 C8 1.473(3) ? C8 C9 1.379(3) ? C9 C10 1.367(3) ? C9 H9 0.9300 ? C10 C11 1.372(3) ? C10 H10 0.9300 ? C11 C12 1.370(3) ? C11 H11 0.9300 ? C12 H12 0.9300 ? C13 C14 1.371(2) ? C13 C18 1.376(3) ? C14 C15 1.382(2) ? C14 H14 0.9300 ? C15 C16 1.388(3) ? C15 H15 0.9300 ? C16 C17 1.378(3) ? C16 C19 1.520(2) ? C17 C18 1.374(3) ? C17 H17 0.9300 ? C18 H18 0.9300 ? C19 C20 1.504(3) ? C19 C21 1.519(3) ? C19 H19 0.9800 ? C20 H20A 0.9600 ? C20 H20B 0.9600 ? C20 H20C 0.9600 ? C21 H21A 0.9600 ? C21 H21B 0.9600 ? C21 H21C 0.9600 ? 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 C6 N2 N3 C7 -0.3(2) ? C5 N1 C1 C2 -1.0(3) ? C5 N1 C1 C6 -178.83(17) ? N1 C1 C2 C3 0.0(3) ? C6 C1 C2 C3 177.72(17) ? C1 C2 C3 C4 1.4(3) ? C2 C3 C4 C5 -1.6(3) ? C1 N1 C5 C4 0.8(3) ? C3 C4 C5 N1 0.5(3) ? N3 N2 C6 N5 0.4(2) ? N3 N2 C6 C1 -178.67(17) ? C7 N5 C6 N2 -0.3(2) ? C13 N5 C6 N2 178.67(16) ? C7 N5 C6 C1 178.68(18) ? C13 N5 C6 C1 -2.3(3) ? N1 C1 C6 N2 134.5(2) ? C2 C1 C6 N2 -43.3(3) ? N1 C1 C6 N5 -44.3(3) yes C2 C1 C6 N5 137.79(19) ? N2 N3 C7 N5 0.1(2) ? N2 N3 C7 C8 -177.18(16) ? C6 N5 C7 N3 0.1(2) ? C13 N5 C7 N3 -178.77(17) ? C6 N5 C7 C8 177.24(18) ? C13 N5 C7 C8 -1.7(3) ? C12 N4 C8 C9 0.1(3) ? C12 N4 C8 C7 -176.33(17) ? N3 C7 C8 N4 147.41(18) ? N5 C7 C8 N4 -29.4(3) ? N3 C7 C8 C9 -29.2(3) yes N5 C7 C8 C9 154.06(18) ? N4 C8 C9 C10 -1.5(3) ? C7 C8 C9 C10 174.92(18) ? C8 C9 C10 C11 1.1(3) ? C9 C10 C11 C12 0.6(3) ? C8 N4 C12 C11 1.7(3) ? C10 C11 C12 N4 -2.0(3) ? C6 N5 C13 C14 120.9(2) ? C7 N5 C13 C14 -60.4(3) yes C6 N5 C13 C18 -57.1(2) ? C7 N5 C13 C18 121.6(2) ? C18 C13 C14 C15 1.9(3) ? N5 C13 C14 C15 -176.03(16) ? C13 C14 C15 C16 0.8(3) ? C14 C15 C16 C17 -2.1(3) ? C14 C15 C16 C19 174.39(17) ? C15 C16 C17 C18 0.9(3) ? C19 C16 C17 C18 -175.78(18) ? C16 C17 C18 C13 1.7(3) ? C14 C13 C18 C17 -3.1(3) ? N5 C13 C18 C17 174.90(16) ? C17 C16 C19 C20 -161.1(2) ? C15 C16 C19 C20 22.5(3) ? C17 C16 C19 C21 72.4(3) ? C15 C16 C19 C21 -104.1(2) ?