#============================================================================== data_global loop_ _journal_name_full 'European Journal of Chemistry' _journal_coden_ASTM EJCUA9 _journal_volume 11 _journal_issue 1 _journal_year 2020 _journal_page_first 50 _journal_page_last 59 #=============================================================================== data_1 _audit_update_record ; 2013-11-18 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 4,5-diphenyl-1H-imidazole _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H12 N2' _chemical_formula_weight 220.27 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' 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' _cell_length_a 11.161(5) _cell_length_b 9.263(5) _cell_length_c 11.794(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 93.572(5) _cell_angle_gamma 90.000(5) _cell_volume 1216.9(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2787 _cell_measurement_theta_min 3.28 _cell_measurement_theta_max 29.21 _exptl_crystal_description 'cubic' _exptl_crystal_colour white _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.47 _exptl_crystal_size_min 0.45 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.202 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.965 _exptl_absorpt_correction_T_max 0.968 _exptl_absorpt_process_details '(North et al., 1968)' _exptl_special_details ? _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5302 _diffrn_reflns_av_R_equivalents 0.0200 _diffrn_reflns_av_sigmaI/netI 0.0387 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 29.21 _reflns_number_total 2787 _reflns_number_gt 1820 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0438P)^2^+0.0939P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0079(17) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2787 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0832 _refine_ls_R_factor_gt 0.0471 _refine_ls_wR_factor_ref 0.1149 _refine_ls_wR_factor_gt 0.0982 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group H1 H 0.3776(15) -0.0645(15) 0.7622(13) 0.058(4) Uiso 1 1 d . . . H H 0.5489(16) -0.230(2) 0.7647(15) 0.077(6) Uiso 1 1 d . . . N2 N 0.47927(11) 0.07707(13) 0.67879(11) 0.0486(3) Uani 1 1 d . . . C2 C 0.64035(13) -0.07080(15) 0.68172(12) 0.0417(4) Uani 1 1 d . . . N1 N 0.54777(11) -0.13652(14) 0.73400(11) 0.0460(3) Uani 1 1 d . . . C3 C 0.59638(13) 0.06232(15) 0.64856(12) 0.0426(4) Uani 1 1 d . . . C4 C 0.65522(13) 0.18616(15) 0.59656(12) 0.0437(4) Uani 1 1 d . . . C10 C 0.75490(13) -0.14468(15) 0.66910(12) 0.0445(4) Uani 1 1 d . . . C1 C 0.45446(15) -0.04541(17) 0.72966(14) 0.0501(4) Uani 1 1 d . . . C6 C 0.82113(16) 0.35072(18) 0.58851(18) 0.0674(5) Uani 1 1 d . . . H6 H 0.8986 0.3779 0.6132 0.081 Uiso 1 1 calc R . . C9 C 0.59218(16) 0.26933(18) 0.51524(13) 0.0572(4) Uani 1 1 d . . . H9 H 0.5148 0.2427 0.4897 0.069 Uiso 1 1 calc R . . C5 C 0.77069(14) 0.22855(16) 0.63222(14) 0.0541(4) Uani 1 1 d . . . H5 H 0.8146 0.1739 0.6863 0.065 Uiso 1 1 calc R . . C11 C 0.79825(15) -0.24584(18) 0.74810(14) 0.0575(4) Uani 1 1 d . . . H11 H 0.7543 -0.2667 0.8105 0.069 Uiso 1 1 calc R . . C15 C 0.90575(17) -0.3160(2) 0.73532(16) 0.0715(5) Uani 1 1 d . . . H15 H 0.9330 -0.3845 0.7885 0.086 Uiso 1 1 calc R . . C7 C 0.7575(2) 0.4323(2) 0.50878(18) 0.0745(6) Uani 1 1 d . . . H7 H 0.7913 0.5151 0.4797 0.089 Uiso 1 1 calc R . . C12 C 0.82289(15) -0.11632(18) 0.57667(14) 0.0595(5) Uani 1 1 d . . . H12 H 0.7951 -0.0504 0.5217 0.071 Uiso 1 1 calc R . . C14 C 0.97242(17) -0.2852(2) 0.64497(17) 0.0737(6) Uani 1 1 d . . . H14 H 1.0453 -0.3317 0.6371 0.088 Uiso 1 1 calc R . . C13 C 0.93112(17) -0.1852(2) 0.56598(16) 0.0718(5) Uani 1 1 d . . . H13 H 0.9766 -0.1637 0.5047 0.086 Uiso 1 1 calc R . . C8 C 0.6436(2) 0.3912(2) 0.47216(15) 0.0727(6) Uani 1 1 d . . . H8 H 0.6005 0.4462 0.4177 0.087 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N2 0.0465(8) 0.0424(7) 0.0577(8) -0.0003(6) 0.0090(6) 0.0007(6) C2 0.0465(9) 0.0385(8) 0.0406(7) -0.0035(7) 0.0056(6) -0.0025(7) N1 0.0516(8) 0.0343(7) 0.0529(8) -0.0017(6) 0.0091(6) -0.0028(6) C3 0.0457(8) 0.0399(8) 0.0424(8) -0.0038(7) 0.0040(6) -0.0006(7) C4 0.0501(9) 0.0393(8) 0.0426(8) -0.0013(7) 0.0091(7) 0.0032(7) C10 0.0492(9) 0.0407(9) 0.0438(8) -0.0063(7) 0.0034(7) -0.0013(7) C1 0.0474(10) 0.0429(9) 0.0610(10) -0.0055(8) 0.0100(8) -0.0032(8) C6 0.0522(11) 0.0535(11) 0.0987(14) 0.0054(10) 0.0208(10) -0.0030(8) C9 0.0665(11) 0.0601(11) 0.0449(9) 0.0068(8) 0.0019(8) 0.0018(8) C5 0.0476(9) 0.0452(9) 0.0698(11) 0.0067(8) 0.0069(8) 0.0028(7) C11 0.0590(11) 0.0633(11) 0.0504(9) 0.0034(8) 0.0051(8) 0.0073(9) C15 0.0688(13) 0.0828(14) 0.0619(11) 0.0019(10) -0.0050(9) 0.0255(10) C7 0.0878(15) 0.0521(11) 0.0875(14) 0.0165(10) 0.0362(12) -0.0004(10) C12 0.0677(12) 0.0575(10) 0.0548(10) 0.0017(8) 0.0152(8) 0.0107(9) C14 0.0559(11) 0.0943(15) 0.0709(12) -0.0120(11) 0.0046(9) 0.0225(10) C13 0.0677(12) 0.0826(13) 0.0675(12) -0.0058(10) 0.0236(10) 0.0105(10) C8 0.0937(16) 0.0673(12) 0.0579(11) 0.0224(9) 0.0104(10) 0.0070(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N2 C1 1.321(2) . ? N2 C3 1.3829(19) . ? C2 C3 1.375(2) . ? C2 N1 1.3776(18) . ? C2 C10 1.466(2) . ? N1 C1 1.339(2) . ? N1 H 0.936(18) . ? C3 C4 1.474(2) . ? C4 C5 1.387(2) . ? C4 C9 1.387(2) . ? C10 C11 1.387(2) . ? C10 C12 1.392(2) . ? C1 H1 0.977(16) . ? C6 C7 1.370(3) . ? C6 C5 1.378(2) . ? C6 H6 0.9300 . ? C9 C8 1.378(2) . ? C9 H9 0.9300 . ? C5 H5 0.9300 . ? C11 C15 1.381(2) . ? C11 H11 0.9300 . ? C15 C14 1.367(3) . ? C15 H15 0.9300 . ? C7 C8 1.371(3) . ? C7 H7 0.9300 . ? C12 C13 1.379(2) . ? C12 H12 0.9300 . ? C14 C13 1.373(3) . ? C14 H14 0.9300 . ? C13 H13 0.9300 . ? C8 H8 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N2 C3 105.10(12) . . ? C3 C2 N1 105.03(13) . . ? C3 C2 C10 133.46(13) . . ? N1 C2 C10 121.49(13) . . ? C1 N1 C2 107.92(14) . . ? C1 N1 H 126.0(11) . . ? C2 N1 H 126.1(11) . . ? C2 C3 N2 109.98(12) . . ? C2 C3 C4 130.98(14) . . ? N2 C3 C4 118.88(12) . . ? C5 C4 C9 118.29(14) . . ? C5 C4 C3 121.58(13) . . ? C9 C4 C3 119.99(14) . . ? C11 C10 C12 117.99(15) . . ? C11 C10 C2 121.14(14) . . ? C12 C10 C2 120.87(14) . . ? N2 C1 N1 111.97(15) . . ? N2 C1 H1 123.2(9) . . ? N1 C1 H1 124.8(9) . . ? C7 C6 C5 120.21(18) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C8 C9 C4 120.35(17) . . ? C8 C9 H9 119.8 . . ? C4 C9 H9 119.8 . . ? C6 C5 C4 120.83(16) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C15 C11 C10 120.90(16) . . ? C15 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C14 C15 C11 120.38(17) . . ? C14 C15 H15 119.8 . . ? C11 C15 H15 119.8 . . ? C6 C7 C8 119.63(17) . . ? C6 C7 H7 120.2 . . ? C8 C7 H7 120.2 . . ? C13 C12 C10 120.53(17) . . ? C13 C12 H12 119.7 . . ? C10 C12 H12 119.7 . . ? C15 C14 C13 119.57(17) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C14 C13 C12 120.61(17) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C7 C8 C9 120.69(17) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 C2 N1 C1 0.69(16) . . . . ? C10 C2 N1 C1 -178.06(13) . . . . ? N1 C2 C3 N2 -0.61(15) . . . . ? C10 C2 C3 N2 177.92(15) . . . . ? N1 C2 C3 C4 174.68(14) . . . . ? C10 C2 C3 C4 -6.8(3) . . . . ? C1 N2 C3 C2 0.29(16) . . . . ? C1 N2 C3 C4 -175.64(13) . . . . ? C2 C3 C4 C5 -41.2(2) . . . . ? N2 C3 C4 C5 133.77(15) . . . . ? C2 C3 C4 C9 143.21(16) . . . . ? N2 C3 C4 C9 -41.85(19) . . . . ? C3 C2 C10 C11 151.24(16) . . . . ? N1 C2 C10 C11 -30.4(2) . . . . ? C3 C2 C10 C12 -29.4(2) . . . . ? N1 C2 C10 C12 148.93(14) . . . . ? C3 N2 C1 N1 0.16(17) . . . . ? C2 N1 C1 N2 -0.54(18) . . . . ? C5 C4 C9 C8 -0.4(2) . . . . ? C3 C4 C9 C8 175.34(15) . . . . ? C7 C6 C5 C4 0.0(3) . . . . ? C9 C4 C5 C6 0.4(2) . . . . ? C3 C4 C5 C6 -175.26(14) . . . . ? C12 C10 C11 C15 0.1(2) . . . . ? C2 C10 C11 C15 179.48(15) . . . . ? C10 C11 C15 C14 0.9(3) . . . . ? C5 C6 C7 C8 -0.4(3) . . . . ? C11 C10 C12 C13 -1.3(2) . . . . ? C2 C10 C12 C13 179.36(15) . . . . ? C11 C15 C14 C13 -0.8(3) . . . . ? C15 C14 C13 C12 -0.4(3) . . . . ? C10 C12 C13 C14 1.4(3) . . . . ? C6 C7 C8 C9 0.4(3) . . . . ? C4 C9 C8 C7 0.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 29.21 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.132 _refine_diff_density_min -0.134 _refine_diff_density_rms 0.027