#------------------------------------------------------------------------------ #$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/29/2012970.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_2012970 loop_ _publ_author_name 'V\'azquez Garc\'ia, Rosa A.' 'Bern\`es, Sylvain' 'Guti\'errez P\'erez, Ren\'e' 'Mart\'inez Garc\'ia, Marcos' _publ_section_title ; 2-Methyl-1,4,5-triphenyl-1H-imidazole ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o619 _journal_page_last o620 _journal_volume 58 _journal_year 2002 _chemical_formula_moiety 'C22 H18 N2' _chemical_formula_sum 'C22 H18 N2' _chemical_formula_weight 310.38 _chemical_melting_point 533 _chemical_name_systematic 2-Methyl-1,4,5-triphenyl-1H-imidazole _space_group_IT_number 2 _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 SHELXL97 _cell_angle_alpha 96.288(6) _cell_angle_beta 92.042(4) _cell_angle_gamma 106.338(5) _cell_formula_units_Z 2 _cell_length_a 8.5768(5) _cell_length_b 9.8285(9) _cell_length_c 10.7315(7) _cell_measurement_reflns_used 78 _cell_measurement_temperature 299.0(10) _cell_measurement_theta_max 15.01 _cell_measurement_theta_min 4.52 _cell_volume 860.79(11) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens, 1996)' _computing_data_reduction XSCANS _computing_molecular_graphics SHELXTL-Plus _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXTL-Plus (Sheldrick, 1998)' _diffrn_ambient_temperature 299.0(10) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.016 _diffrn_reflns_av_sigmaI/netI 0.025 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 5916 _diffrn_reflns_theta_full 30.00 _diffrn_reflns_theta_max 30.00 _diffrn_reflns_theta_min 1.91 _diffrn_standards_decay_% 2 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.198 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description regular_prism _exptl_crystal_F_000 328 _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.65 _exptl_crystal_size_min 0.36 _refine_diff_density_max 0.27 _refine_diff_density_min -0.20 _refine_ls_extinction_coef 0.034(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 219 _refine_ls_number_reflns 4985 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.044 _refine_ls_R_factor_all 0.069 _refine_ls_R_factor_gt 0.050 _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^)+(0.0582P)^2^+0.1152P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.132 _refine_ls_wR_factor_ref 0.145 _reflns_number_gt 3642 _reflns_number_total 4985 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file fg1661.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M P-1 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' 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 'Triclinic' changed to 'triclinic' 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_database_code 2012970 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -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 N1 0.47519(12) 0.26420(11) 0.39603(9) 0.0503(2) Uani d . 1 . . N C2 0.39422(15) 0.31749(13) 0.48871(11) 0.0520(3) Uani d . 1 . . C N3 0.46889(13) 0.32914(11) 0.59994(9) 0.0532(3) Uani d . 1 . . N C4 0.60569(15) 0.28237(13) 0.58033(11) 0.0496(3) Uani d . 1 . . C C5 0.61126(15) 0.24018(13) 0.45447(11) 0.0482(3) Uani d . 1 . . C C6 0.42645(14) 0.23693(13) 0.26405(11) 0.0510(3) Uani d . 1 . . C C7 0.42207(17) 0.34995(15) 0.19951(13) 0.0607(3) Uani d . 1 . . C H7 0.4539 0.4429 0.2404 0.073 Uiso calc R 1 . . H C8 0.36975(19) 0.32349(19) 0.07298(14) 0.0726(4) Uani d . 1 . . C H8 0.3637 0.3987 0.0293 0.087 Uiso calc R 1 . . H C9 0.32680(19) 0.1863(2) 0.01208(14) 0.0761(4) Uani d . 1 . . C H9 0.2921 0.1691 -0.0728 0.091 Uiso calc R 1 . . H C10 0.3350(2) 0.07479(19) 0.07588(14) 0.0763(4) Uani d . 1 . . C H10 0.3076 -0.0175 0.0337 0.092 Uiso calc R 1 . . H C11 0.38393(18) 0.09873(15) 0.20340(13) 0.0639(3) Uani d . 1 . . C H11 0.3880 0.0230 0.2471 0.077 Uiso calc R 1 . . H C12 0.23945(16) 0.35349(16) 0.46493(14) 0.0639(4) Uani d . 1 . . C H12A 0.2049 0.3889 0.5430 0.096 Uiso calc PR 0.63(2) A 1 H H12B 0.1572 0.2694 0.4274 0.096 Uiso calc PR 0.63(2) A 1 H H12C 0.2564 0.4254 0.4091 0.096 Uiso calc PR 0.63(2) A 1 H H12D 0.2230 0.3593 0.3769 0.096 Uiso d PR 0.37(2) A 2 H H12E 0.2452 0.4438 0.5121 0.096 Uiso d PR 0.37(2) A 2 H H12F 0.1503 0.2807 0.4904 0.096 Uiso d PR 0.37(2) A 2 H C13 0.72423(16) 0.29509(13) 0.68670(11) 0.0518(3) Uani d . 1 . . C C14 0.88829(18) 0.31270(17) 0.67127(13) 0.0660(4) Uani d . 1 . . C H14 0.9251 0.3125 0.5908 0.079 Uiso calc R 1 . . H C15 0.9983(2) 0.33053(19) 0.77360(15) 0.0749(4) Uani d . 1 . . C H15 1.1076 0.3409 0.7613 0.090 Uiso calc R 1 . . H C16 0.9462(2) 0.33292(19) 0.89336(15) 0.0789(5) Uani d . 1 . . C H16 1.0200 0.3455 0.9622 0.095 Uiso calc R 1 . . H C17 0.7844(2) 0.3166(2) 0.91031(14) 0.0813(5) Uani d . 1 . . C H17 0.7489 0.3183 0.9912 0.098 Uiso calc R 1 . . H C18 0.6738(2) 0.29779(17) 0.80862(13) 0.0668(4) Uani d . 1 . . C H18 0.5645 0.2868 0.8217 0.080 Uiso calc R 1 . . H C19 0.72545(15) 0.17892(13) 0.38347(10) 0.0503(3) Uani d . 1 . . C C20 0.80897(18) 0.24451(19) 0.28823(13) 0.0689(4) Uani d . 1 . . C H20 0.7947 0.3299 0.2676 0.083 Uiso calc R 1 . . H C21 0.91500(19) 0.1822(2) 0.22297(14) 0.0847(5) Uani d . 1 . . C H21 0.9705 0.2261 0.1585 0.102 Uiso calc R 1 . . H C22 0.9376(2) 0.0571(2) 0.25327(16) 0.0823(5) Uani d . 1 . . C H22 1.0084 0.0163 0.2096 0.099 Uiso calc R 1 . . H C23 0.8569(2) -0.0069(2) 0.34668(18) 0.0854(5) Uani d . 1 . . C H23 0.8732 -0.0915 0.3676 0.103 Uiso calc R 1 . . H C24 0.7505(2) 0.05196(16) 0.41149(15) 0.0690(4) Uani d . 1 . . C H24 0.6948 0.0058 0.4748 0.083 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 0.0495(5) 0.0548(5) 0.0449(5) 0.0157(4) 0.0026(4) -0.0032(4) C2 0.0490(6) 0.0528(6) 0.0509(6) 0.0131(5) 0.0065(5) -0.0037(5) N3 0.0533(6) 0.0559(6) 0.0485(5) 0.0153(4) 0.0082(4) -0.0020(4) C4 0.0522(6) 0.0509(6) 0.0447(6) 0.0142(5) 0.0077(5) 0.0013(4) C5 0.0490(6) 0.0506(6) 0.0441(6) 0.0144(5) 0.0043(4) 0.0017(4) C6 0.0452(6) 0.0589(7) 0.0453(6) 0.0136(5) 0.0008(4) -0.0046(5) C7 0.0618(8) 0.0618(7) 0.0550(7) 0.0164(6) -0.0035(6) -0.0016(6) C8 0.0718(9) 0.0880(11) 0.0556(8) 0.0206(8) -0.0046(7) 0.0079(7) C9 0.0666(9) 0.1012(12) 0.0489(7) 0.0127(8) -0.0032(6) -0.0084(7) C10 0.0756(10) 0.0776(10) 0.0607(8) 0.0095(8) 0.0002(7) -0.0219(7) C11 0.0671(8) 0.0585(7) 0.0599(7) 0.0133(6) 0.0035(6) -0.0071(6) C12 0.0517(7) 0.0728(8) 0.0667(8) 0.0215(6) 0.0050(6) -0.0036(6) C13 0.0614(7) 0.0510(6) 0.0440(6) 0.0189(5) 0.0049(5) 0.0026(5) C14 0.0628(8) 0.0854(10) 0.0491(7) 0.0233(7) 0.0032(6) 0.0007(6) C15 0.0681(9) 0.0919(11) 0.0657(9) 0.0287(8) -0.0055(7) 0.0014(8) C16 0.0945(12) 0.0896(11) 0.0565(8) 0.0373(9) -0.0156(8) 0.0041(7) C17 0.1053(13) 0.1051(13) 0.0439(7) 0.0458(11) 0.0064(7) 0.0120(7) C18 0.0756(9) 0.0829(10) 0.0481(7) 0.0311(8) 0.0106(6) 0.0104(6) C19 0.0480(6) 0.0606(7) 0.0405(5) 0.0161(5) 0.0026(4) -0.0027(5) C20 0.0594(8) 0.0996(11) 0.0536(7) 0.0278(8) 0.0089(6) 0.0204(7) C21 0.0608(9) 0.1465(17) 0.0460(7) 0.0279(10) 0.0130(6) 0.0113(9) C22 0.0615(9) 0.1152(14) 0.0683(9) 0.0362(9) 0.0008(7) -0.0245(9) C23 0.0846(11) 0.0763(10) 0.0999(13) 0.0374(9) 0.0152(10) -0.0107(9) C24 0.0741(9) 0.0610(8) 0.0753(9) 0.0248(7) 0.0189(7) 0.0034(7) 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 C2 . 1.3732(15) y N1 C5 . 1.3950(16) y N1 C6 . 1.4368(15) y C2 N3 . 1.3123(16) y C2 C12 . 1.4874(18) y N3 C4 . 1.3900(15) y C4 C5 . 1.3754(15) y C4 C13 . 1.4721(17) y C5 C19 . 1.4787(16) y C6 C7 . 1.3803(19) n C6 C11 . 1.3829(18) n C7 C8 . 1.3880(19) n C7 H7 . 0.9300 n C8 C9 . 1.375(2) n C8 H8 . 0.9300 n C9 C10 . 1.371(2) n C9 H9 . 0.9300 n C10 C11 . 1.392(2) n C10 H10 . 0.9300 n C11 H11 . 0.9300 n C12 H12A . 0.9600 n C12 H12B . 0.9600 n C12 H12C . 0.9600 n C12 H12D . 0.9601 n C12 H12E . 0.9600 n C12 H12F . 0.9600 n C13 C14 . 1.3868(19) n C13 C18 . 1.3925(18) n C14 C15 . 1.385(2) n C14 H14 . 0.9300 n C15 C16 . 1.375(2) n C15 H15 . 0.9300 n C16 C17 . 1.373(3) n C16 H16 . 0.9300 n C17 C18 . 1.382(2) n C17 H17 . 0.9300 n C18 H18 . 0.9300 n C19 C20 . 1.3821(18) n C19 C24 . 1.3863(19) n C20 C21 . 1.399(2) n C20 H20 . 0.9300 n C21 C22 . 1.368(3) n C21 H21 . 0.9300 n C22 C23 . 1.350(3) n C22 H22 . 0.9300 n C23 C24 . 1.381(2) n C23 H23 . 0.9300 n C24 H24 . 0.9300 n 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_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 3 5 4 -1 5 1 1 -2 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 C2 N1 C5 107.14(10) y C2 N1 C6 125.99(10) y C5 N1 C6 126.87(10) y N3 C2 N1 111.36(11) y N3 C2 C12 124.87(11) y N1 C2 C12 123.75(11) y C2 N3 C4 106.25(10) y C5 C4 N3 109.98(11) y C5 C4 C13 130.35(11) y N3 C4 C13 119.44(10) y C4 C5 N1 105.28(10) y C4 C5 C19 132.45(11) y N1 C5 C19 122.27(10) y C7 C6 C11 120.84(12) n C7 C6 N1 119.17(11) n C11 C6 N1 119.99(12) n C6 C7 C8 119.33(13) n C6 C7 H7 120.3 n C8 C7 H7 120.3 n C9 C8 C7 120.15(15) n C9 C8 H8 119.9 n C7 C8 H8 119.9 n C10 C9 C8 120.29(14) n C10 C9 H9 119.9 n C8 C9 H9 119.9 n C9 C10 C11 120.43(14) n C9 C10 H10 119.8 n C11 C10 H10 119.8 n C6 C11 C10 118.92(15) n C6 C11 H11 120.5 n C10 C11 H11 120.5 n C2 C12 H12A 109.5 n C2 C12 H12B 109.5 n H12A C12 H12B 109.5 n C2 C12 H12C 109.5 n H12A C12 H12C 109.5 n H12B C12 H12C 109.5 n C2 C12 H12D 109.5 n H12A C12 H12D 138.1 n H12B C12 H12D 70.8 n C2 C12 H12E 109.5 n H12B C12 H12E 138.1 n H12C C12 H12E 70.8 n H12D C12 H12E 109.5 n C2 C12 H12F 109.5 n H12A C12 H12F 70.8 n H12C C12 H12F 138.1 n H12D C12 H12F 109.5 n H12E C12 H12F 109.5 n C14 C13 C18 117.88(13) n C14 C13 C4 122.39(11) n C18 C13 C4 119.63(12) n C15 C14 C13 121.16(14) n C15 C14 H14 119.4 n C13 C14 H14 119.4 n C16 C15 C14 120.15(16) n C16 C15 H15 119.9 n C14 C15 H15 119.9 n C17 C16 C15 119.42(15) n C17 C16 H16 120.3 n C15 C16 H16 120.3 n C16 C17 C18 120.76(14) n C16 C17 H17 119.6 n C18 C17 H17 119.6 n C17 C18 C13 120.63(15) n C17 C18 H18 119.7 n C13 C18 H18 119.7 n C20 C19 C24 118.23(13) n C20 C19 C5 121.82(12) n C24 C19 C5 119.95(12) n C19 C20 C21 119.85(16) n C19 C20 H20 120.1 n C21 C20 H20 120.1 n C22 C21 C20 120.52(15) n C22 C21 H21 119.7 n C20 C21 H21 119.7 n C23 C22 C21 119.81(15) n C23 C22 H22 120.1 n C21 C22 H22 120.1 n C22 C23 C24 120.66(17) n C22 C23 H23 119.7 n C24 C23 H23 119.7 n C23 C24 C19 120.93(15) n C23 C24 H24 119.5 n C19 C24 H24 119.5 n 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 C5 N1 C2 N3 0.23(14) n C6 N1 C2 N3 179.47(11) n C5 N1 C2 C12 -178.35(12) n C6 N1 C2 C12 0.89(19) n N1 C2 N3 C4 0.33(14) n C12 C2 N3 C4 178.89(12) n C2 N3 C4 C5 -0.78(14) n C2 N3 C4 C13 174.26(11) n N3 C4 C5 N1 0.91(13) n C13 C4 C5 N1 -173.43(12) n N3 C4 C5 C19 -178.01(12) n C13 C4 C5 C19 7.7(2) n C2 N1 C5 C4 -0.69(13) n C6 N1 C5 C4 -179.92(11) n C2 N1 C5 C19 178.37(11) n C6 N1 C5 C19 -0.86(19) n C2 N1 C6 C7 63.99(17) n C5 N1 C6 C7 -116.92(14) n C2 N1 C6 C11 -115.71(15) n C5 N1 C6 C11 63.38(17) n C11 C6 C7 C8 1.9(2) n N1 C6 C7 C8 -177.82(12) n C6 C7 C8 C9 -1.7(2) n C7 C8 C9 C10 0.2(3) n C8 C9 C10 C11 1.2(3) n C7 C6 C11 C10 -0.6(2) n N1 C6 C11 C10 179.12(12) n C9 C10 C11 C6 -1.0(2) n C5 C4 C13 C14 23.2(2) n N3 C4 C13 C14 -150.74(13) n C5 C4 C13 C18 -160.56(14) n N3 C4 C13 C18 25.55(18) n C18 C13 C14 C15 0.8(2) n C4 C13 C14 C15 177.19(14) n C13 C14 C15 C16 -0.9(3) n C14 C15 C16 C17 0.4(3) n C15 C16 C17 C18 0.1(3) n C16 C17 C18 C13 -0.1(3) n C14 C13 C18 C17 -0.4(2) n C4 C13 C18 C17 -176.84(14) n C4 C5 C19 C20 -121.98(16) n N1 C5 C19 C20 59.26(17) n C4 C5 C19 C24 58.3(2) n N1 C5 C19 C24 -120.45(14) n C24 C19 C20 C21 0.2(2) n C5 C19 C20 C21 -179.56(13) n C19 C20 C21 C22 -0.5(2) n C20 C21 C22 C23 0.1(3) n C21 C22 C23 C24 0.5(3) n C22 C23 C24 C19 -0.9(3) n C20 C19 C24 C23 0.5(2) n C5 C19 C24 C23 -179.78(14) n _cod_database_fobs_code 2012970 _journal_paper_doi 10.1107/S0108270102016220