#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2206309.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_2206309 loop_ _publ_author_name 'Liu, Xu-Feng' 'Zhong, Zeng-Pei' 'Xu, Zun-Le' _publ_section_title ; 4-[4,5-Bis(4-methoxyphenyl)-1H-imidazol-2-yl]benzonitrile ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1976 _journal_page_last o1977 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C24 H19 N3 O2' _chemical_formula_moiety 'C24 H19 N3 O2' _chemical_formula_sum 'C24 H19 N3 O2' _chemical_formula_weight 381.42 _chemical_name_systematic ; 4-[4,5-Bis(4-methoxyphenyl)-1H-imidazol-2-yl]benzonitrile ; _space_group_IT_number 61 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _audit_creation_method 'WinGX routine CIF_UPDATE' _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 9.801(3) _cell_length_b 15.549(4) _cell_length_c 26.142(7) _cell_measurement_reflns_used 4326 _cell_measurement_temperature 273(2) _cell_measurement_theta_max 27.0 _cell_measurement_theta_min 2.6 _cell_volume 3983.9(19) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_molecular_graphics SHELXTL _computing_publication_material 'SHELXTL and PLATON (Spek, 1990)' _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Bruker, 1997)' _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker SMART CCD 1K area-detector' _diffrn_measurement_method '\f and \w' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0408 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_number 17659 _diffrn_reflns_theta_full 27.07 _diffrn_reflns_theta_max 27.07 _diffrn_reflns_theta_min 2.58 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_T_max 0.9740 _exptl_absorpt_correction_T_min 0.9614 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1600 _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.32 _refine_diff_density_max 0.38 _refine_diff_density_min -0.56 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_hydrogen_treatment refU _refine_ls_matrix_type full _refine_ls_number_parameters 261 _refine_ls_number_reflns 4326 _refine_ls_number_restraints 4 _refine_ls_restrained_S_all 1.024 _refine_ls_R_factor_gt 0.0541 _refine_ls_shift/su_max 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0634P)^2^+2.2522P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.1296 _reflns_number_gt 2563 _reflns_number_total 4326 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file wk6050.cif _[local]_cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' 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 3984.1(19) _cod_database_code 2206309 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' 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 O1 -0.1756(2) 0.30445(13) 0.00221(6) 0.0669(6) Uani d . 1 . . O O2A 0.5881(4) 0.4511(3) 0.1531(2) 0.0535(16) Uiso d PD 0.453(10) A 1 O O2B 0.5977(3) 0.4568(2) 0.1741(2) 0.0599(14) Uiso d PD 0.547(10) A 2 O N1 -0.03100(18) 0.16509(12) 0.22640(6) 0.0365(4) Uani d . 1 . . N H1A -0.1083 0.1414 0.2198 0.044 Uiso calc R 1 . . H N2 0.15676(18) 0.19979(12) 0.26803(6) 0.0375(4) Uani d . 1 . . N N3 -0.2246(3) -0.02281(18) 0.48686(10) 0.0870(9) Uani d . 1 . . N C1 0.0502(2) 0.12506(16) 0.36298(8) 0.0426(6) Uani d . 1 . . C H1 0.1312 0.1561 0.3647 0.051 Uiso calc R 1 . . H C2 -0.0146(2) 0.11409(14) 0.31590(7) 0.0342(5) Uani d . 1 . . C C3 0.0395(2) 0.15785(14) 0.27065(8) 0.0344(5) Uani d . 1 . . C C4 0.1590(2) 0.23811(14) 0.22041(8) 0.0357(5) Uani d . 1 . . C C5 0.0422(2) 0.21675(14) 0.19388(8) 0.0343(5) Uani d . 1 . . C C6 -0.1337(2) 0.06622(15) 0.31409(9) 0.0434(6) Uani d . 1 . . C H6 -0.1770 0.0572 0.2829 0.052 Uiso calc R 1 . . H C7 -0.1890(3) 0.03175(16) 0.35818(9) 0.0477(6) Uani d . 1 . . C H7 -0.2695 0.0003 0.3565 0.057 Uiso calc R 1 . . H C8 -0.1246(3) 0.04394(15) 0.40491(8) 0.0436(6) Uani d . 1 . . C C9 -0.0042(3) 0.09058(16) 0.40698(9) 0.0467(6) Uani d . 1 . . C H9 0.0398 0.0986 0.4381 0.056 Uiso calc R 1 . . H C10 -0.1822(3) 0.00799(18) 0.45080(10) 0.0578(7) Uani d . 1 . . C C11 0.2726(2) 0.29387(15) 0.20442(8) 0.0386(5) Uani d . 1 A . C C12 0.3309(3) 0.35160(17) 0.23854(10) 0.0514(6) Uani d . 1 . . C H12 0.2973 0.3551 0.2718 0.062 Uiso calc R 1 . . H C13 0.4376(3) 0.40379(18) 0.22395(12) 0.0629(8) Uani d . 1 A . C H13 0.4748 0.4419 0.2476 0.076 Uiso calc R 1 . . H C14 0.4902(2) 0.40073(16) 0.17515(13) 0.0615(8) Uani d D 1 . . C C15 0.4324(3) 0.34407(18) 0.14061(11) 0.0585(8) Uani d . 1 A . C H15 0.4656 0.3414 0.1073 0.070 Uiso calc R 1 . . H C16 0.3252(2) 0.29106(16) 0.15525(10) 0.0456(6) Uani d . 1 . . C H16 0.2880 0.2530 0.1316 0.055 Uiso calc R 1 A . H C17 -0.0113(2) 0.23867(14) 0.14317(8) 0.0353(5) Uani d . 1 . . C C18 -0.0015(2) 0.32100(15) 0.12327(8) 0.0412(5) Uani d . 1 . . C H18 0.0428 0.3636 0.1419 0.049 Uiso calc R 1 . . H C19 -0.0565(2) 0.34054(16) 0.07613(9) 0.0452(6) Uani d . 1 . . C H19 -0.0481 0.3959 0.0631 0.054 Uiso calc R 1 . . H C20 -0.1239(2) 0.27831(17) 0.04820(8) 0.0441(6) Uani d . 1 . . C C21 -0.1337(3) 0.19588(17) 0.06687(8) 0.0482(6) Uani d . 1 . . C H21 -0.1776 0.1534 0.0480 0.058 Uiso calc R 1 . . H C22 -0.0774(2) 0.17702(16) 0.11402(8) 0.0435(6) Uani d . 1 . . C H22 -0.0840 0.1212 0.1266 0.052 Uiso calc R 1 . . H C23 -0.2822(4) 0.2570(2) -0.01908(11) 0.0846(11) Uani d . 1 . . C H23A -0.3084 0.2821 -0.0511 0.127 Uiso calc R 1 . . H H23B -0.3587 0.2573 0.0038 0.127 Uiso calc R 1 . . H H23C -0.2527 0.1988 -0.0246 0.127 Uiso calc R 1 . . H C24A 0.6389(7) 0.4476(4) 0.1032(2) 0.060(2) Uiso d PD 0.453(10) A 1 C H24A 0.7100 0.4896 0.0993 0.090 Uiso calc PR 0.453(10) A 1 H H24B 0.5667 0.4596 0.0795 0.090 Uiso calc PR 0.453(10) A 1 H H24C 0.6750 0.3913 0.0967 0.090 Uiso calc PR 0.453(10) A 1 H C24B 0.6769(6) 0.4419(4) 0.1306(3) 0.078(2) Uiso d PD 0.547(10) A 2 C H24D 0.7534 0.4805 0.1305 0.117 Uiso calc PR 0.547(10) A 2 H H24E 0.6227 0.4514 0.1006 0.117 Uiso calc PR 0.547(10) A 2 H H24F 0.7091 0.3836 0.1309 0.117 Uiso calc PR 0.547(10) A 2 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 0.0731(13) 0.0811(14) 0.0465(10) -0.0207(11) -0.0216(9) 0.0206(10) N1 0.0314(9) 0.0441(11) 0.0341(10) -0.0072(8) -0.0013(7) -0.0002(8) N2 0.0312(10) 0.0452(11) 0.0362(10) -0.0021(9) -0.0015(8) 0.0025(8) N3 0.123(3) 0.0772(19) 0.0605(16) -0.0118(17) 0.0285(16) 0.0173(14) C1 0.0370(12) 0.0502(14) 0.0406(12) -0.0026(11) -0.0040(10) 0.0034(11) C2 0.0306(11) 0.0363(12) 0.0357(11) 0.0029(10) 0.0005(9) 0.0023(9) C3 0.0312(11) 0.0390(12) 0.0330(11) 0.0004(10) -0.0004(9) -0.0003(9) C4 0.0319(11) 0.0400(13) 0.0350(11) -0.0009(10) 0.0026(9) -0.0004(9) C5 0.0313(11) 0.0388(12) 0.0330(11) -0.0023(10) 0.0031(9) -0.0008(9) C6 0.0443(14) 0.0446(14) 0.0412(13) -0.0043(11) -0.0032(10) 0.0023(10) C7 0.0472(14) 0.0429(14) 0.0531(15) -0.0111(12) 0.0033(11) 0.0063(11) C8 0.0549(15) 0.0368(13) 0.0393(12) 0.0024(12) 0.0084(11) 0.0053(10) C9 0.0529(15) 0.0514(15) 0.0358(12) 0.0000(13) -0.0041(11) 0.0038(11) C10 0.0739(19) 0.0497(16) 0.0499(15) -0.0016(15) 0.0118(13) 0.0092(13) C11 0.0295(11) 0.0409(13) 0.0455(13) 0.0006(10) -0.0027(9) 0.0063(10) C12 0.0471(14) 0.0529(16) 0.0543(15) -0.0068(13) -0.0078(12) 0.0037(12) C13 0.0485(16) 0.0516(17) 0.089(2) -0.0145(14) -0.0167(15) 0.0069(15) C14 0.0297(13) 0.0402(15) 0.115(3) -0.0059(12) 0.0046(15) 0.0234(16) C15 0.0431(14) 0.0549(17) 0.0774(19) 0.0078(14) 0.0225(13) 0.0215(14) C16 0.0369(13) 0.0468(14) 0.0531(14) 0.0026(11) 0.0057(11) 0.0059(11) C17 0.0312(11) 0.0434(13) 0.0313(11) -0.0017(10) 0.0018(9) -0.0004(9) C18 0.0389(12) 0.0427(13) 0.0419(12) -0.0048(11) -0.0024(10) -0.0030(10) C19 0.0457(13) 0.0436(14) 0.0462(13) -0.0021(12) -0.0017(11) 0.0087(11) C20 0.0416(13) 0.0569(16) 0.0337(12) -0.0058(12) -0.0014(10) 0.0070(10) C21 0.0547(15) 0.0542(16) 0.0357(12) -0.0168(13) -0.0063(11) -0.0017(11) C22 0.0502(14) 0.0429(14) 0.0375(12) -0.0103(12) -0.0003(10) 0.0046(10) C23 0.091(2) 0.106(3) 0.0569(18) -0.024(2) -0.0336(17) 0.0160(18) 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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 C20 O1 C23 118.1(2) C14 O2A C24A 128.5(5) C14 O2B C24B 109.7(4) C3 N1 C5 108.16(17) C3 N1 H1A 125.9 C5 N1 H1A 125.9 C3 N2 C4 105.87(17) C9 C1 C2 120.9(2) C9 C1 H1 119.6 C2 C1 H1 119.6 C6 C2 C1 118.6(2) C6 C2 C3 121.81(19) C1 C2 C3 119.4(2) N2 C3 N1 111.01(18) N2 C3 C2 125.83(18) N1 C3 C2 123.02(19) C5 C4 N2 109.63(18) C5 C4 C11 128.84(19) N2 C4 C11 121.52(18) N1 C5 C4 105.28(18) N1 C5 C17 120.63(18) C4 C5 C17 134.1(2) C7 C6 C2 120.7(2) C7 C6 H6 119.7 C2 C6 H6 119.7 C6 C7 C8 120.2(2) C6 C7 H7 119.9 C8 C7 H7 119.9 C9 C8 C7 119.5(2) C9 C8 C10 120.3(2) C7 C8 C10 120.1(2) C1 C9 C8 120.1(2) C1 C9 H9 120.0 C8 C9 H9 120.0 N3 C10 C8 177.5(3) C16 C11 C12 117.6(2) C16 C11 C4 121.8(2) C12 C11 C4 120.6(2) C13 C12 C11 121.0(3) C13 C12 H12 119.5 C11 C12 H12 119.5 C14 C13 C12 121.4(3) C14 C13 H13 119.3 C12 C13 H13 119.3 O2A C14 C13 129.4(4) O2B C14 C13 106.5(3) O2A C14 C15 112.1(4) O2B C14 C15 135.2(3) C13 C14 C15 118.3(2) C14 C15 C16 120.5(2) C14 C15 H15 119.7 C16 C15 H15 119.7 C11 C16 C15 121.2(3) C11 C16 H16 119.4 C15 C16 H16 119.4 C22 C17 C18 117.7(2) C22 C17 C5 120.3(2) C18 C17 C5 122.0(2) C19 C18 C17 120.8(2) C19 C18 H18 119.6 C17 C18 H18 119.6 C18 C19 C20 120.4(2) C18 C19 H19 119.8 C20 C19 H19 119.8 O1 C20 C21 124.3(2) O1 C20 C19 115.8(2) C21 C20 C19 119.9(2) C20 C21 C22 119.1(2) C20 C21 H21 120.4 C22 C21 H21 120.4 C21 C22 C17 122.0(2) C21 C22 H22 119.0 C17 C22 H22 119.0 O1 C23 H23A 109.5 O1 C23 H23B 109.5 H23A C23 H23B 109.5 O1 C23 H23C 109.5 H23A C23 H23C 109.5 H23B C23 H23C 109.5 O2A C24A H24A 109.5 O2A C24A H24B 109.5 H24A C24A H24B 109.5 O2A C24A H24C 109.5 H24A C24A H24C 109.5 H24B C24A H24C 109.5 O2B C24B H24D 109.5 O2B C24B H24E 109.5 H24D C24B H24E 109.5 O2B C24B H24F 109.5 H24D C24B H24F 109.5 H24E C24B H24F 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C20 1.367(3) O1 C23 1.395(3) O2A C14 1.3663(10) O2A C24A 1.3961(11) O2B C14 1.3677(10) O2B C24B 1.3966(11) N1 C3 1.352(2) N1 C5 1.372(3) N1 H1A 0.8600 N2 C3 1.323(3) N2 C4 1.380(3) N3 C10 1.136(3) C1 C9 1.377(3) C1 C2 1.395(3) C1 H1 0.9300 C2 C6 1.386(3) C2 C3 1.464(3) C4 C5 1.380(3) C4 C11 1.472(3) C5 C17 1.466(3) C6 C7 1.381(3) C6 H6 0.9300 C7 C8 1.388(3) C7 H7 0.9300 C8 C9 1.386(3) C8 C10 1.439(3) C9 H9 0.9300 C11 C16 1.386(3) C11 C12 1.388(3) C12 C13 1.378(4) C12 H12 0.9300 C13 C14 1.377(4) C13 H13 0.9300 C14 C15 1.383(4) C15 C16 1.390(3) C15 H15 0.9300 C16 H16 0.9300 C17 C22 1.385(3) C17 C18 1.385(3) C18 C19 1.379(3) C18 H18 0.9300 C19 C20 1.381(3) C19 H19 0.9300 C20 C21 1.375(3) C21 C22 1.382(3) C21 H21 0.9300 C22 H22 0.9300 C23 H23A 0.9600 C23 H23B 0.9600 C23 H23C 0.9600 C24A H24A 0.9600 C24A H24B 0.9600 C24A H24C 0.9600 C24B H24D 0.9600 C24B H24E 0.9600 C24B H24F 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 C9 C1 C2 C6 -1.3(3) C9 C1 C2 C3 174.7(2) C4 N2 C3 N1 2.1(2) C4 N2 C3 C2 -173.7(2) C5 N1 C3 N2 -2.0(2) C5 N1 C3 C2 173.91(19) C6 C2 C3 N2 -175.1(2) C1 C2 C3 N2 9.1(3) C6 C2 C3 N1 9.6(3) C1 C2 C3 N1 -166.2(2) C3 N2 C4 C5 -1.4(2) C3 N2 C4 C11 177.4(2) C3 N1 C5 C4 1.1(2) C3 N1 C5 C17 -178.0(2) N2 C4 C5 N1 0.2(2) C11 C4 C5 N1 -178.5(2) N2 C4 C5 C17 179.1(2) C11 C4 C5 C17 0.4(4) C1 C2 C6 C7 1.5(3) C3 C2 C6 C7 -174.4(2) C2 C6 C7 C8 -0.7(4) C6 C7 C8 C9 -0.3(4) C6 C7 C8 C10 -180.0(2) C2 C1 C9 C8 0.3(4) C7 C8 C9 C1 0.5(4) C10 C8 C9 C1 -179.8(2) C5 C4 C11 C16 -41.6(3) N2 C4 C11 C16 139.9(2) C5 C4 C11 C12 138.3(2) N2 C4 C11 C12 -40.2(3) C16 C11 C12 C13 -0.3(4) C4 C11 C12 C13 179.7(2) C11 C12 C13 C14 0.0(4) C24A O2A C14 O2B 162.0(10) C24A O2A C14 C13 -179.1(5) C24A O2A C14 C15 -4.3(6) C24B O2B C14 O2A -29.9(6) C24B O2B C14 C13 165.2(4) C24B O2B C14 C15 -11.9(6) C12 C13 C14 O2A 175.0(3) C12 C13 C14 O2B -177.2(3) C12 C13 C14 C15 0.5(4) O2A C14 C15 C16 -176.2(3) O2B C14 C15 C16 176.1(3) C13 C14 C15 C16 -0.8(4) C12 C11 C16 C15 0.1(3) C4 C11 C16 C15 180.0(2) C14 C15 C16 C11 0.5(4) N1 C5 C17 C22 -40.5(3) C4 C5 C17 C22 140.8(3) N1 C5 C17 C18 137.8(2) C4 C5 C17 C18 -41.0(4) C22 C17 C18 C19 0.4(3) C5 C17 C18 C19 -178.0(2) C17 C18 C19 C20 0.8(4) C23 O1 C20 C21 23.1(4) C23 O1 C20 C19 -157.8(3) C18 C19 C20 O1 179.4(2) C18 C19 C20 C21 -1.5(4) O1 C20 C21 C22 -179.9(2) C19 C20 C21 C22 1.1(4) C20 C21 C22 C17 0.1(4) C18 C17 C22 C21 -0.8(3) C5 C17 C22 C21 177.6(2)