#------------------------------------------------------------------------------ #$Date: 2025-08-19 12:52:15 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301804 $ #$URL: svn://www.crystallography.net/cod/cif/2/21/43/2214373.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_2214373 loop_ _publ_author_name 'Campos-Gaxiola, Jos\'e J.' 'Aguirre, Gerardo' 'Parra-Hake, Miguel' _publ_section_title cis-(+-)-Phenyl[2,4,5-tri-2-pyridyl-4,5-dihydroimidazol-1-yl]methanone _journal_coeditor_code PK2022 _journal_issue 7 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3126 _journal_page_last o3127 _journal_paper_doi 10.1107/S1600536807026414 _journal_volume 63 _journal_year 2007 _chemical_formula_iupac 'C25 H19 N5 O' _chemical_formula_moiety 'C25 H19 N5 O' _chemical_formula_sum 'C25 H19 N5 O' _chemical_formula_weight 405.45 _chemical_name_systematic ; cis-(+-)-Phenyl[2,4,5-tri-2-pyridyl-4,5-dihydroimidazol-1-yl]methanone ; _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 108.65(4) _cell_angle_beta 93.56(3) _cell_angle_gamma 99.84(4) _cell_formula_units_Z 2 _cell_length_a 8.004(3) _cell_length_b 10.085(4) _cell_length_c 13.432(4) _cell_measurement_reflns_used 39 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 11.6 _cell_measurement_theta_min 4.6 _cell_volume 1004.2(7) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens, 1996)' _computing_data_reduction XSCANS _computing_molecular_graphics 'SHELXTL (Bruker, 1998)' _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 0.985 _diffrn_measured_fraction_theta_max 0.985 _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method 2\q/\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 0.0300 _diffrn_reflns_av_sigmaI/netI 0.0769 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 3758 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.0 _diffrn_reflns_theta_min 2.2 _diffrn_standards_decay_% 13.67 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.341 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prismatic _exptl_crystal_F_000 424 _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.14 _refine_diff_density_max 0.147 _refine_diff_density_min -0.213 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.994 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 280 _refine_ls_number_reflns 3483 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.994 _refine_ls_R_factor_all 0.1228 _refine_ls_R_factor_gt 0.0569 _refine_ls_shift/su_max 0.010 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0581P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1126 _refine_ls_wR_factor_ref 0.1402 _reflns_number_gt 1931 _reflns_number_total 3483 _reflns_threshold_expression I>2\s(I) _cod_data_source_file pk2022.cif _cod_data_source_block I _cod_database_code 2214373 _cod_database_fobs_code 2214373 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_type_symbol _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 C C1 0.4369(4) 0.1653(3) 0.7048(2) 0.0388(7) Uani d . 1 C C2 0.4347(4) 0.1829(3) 0.5448(2) 0.0433(8) Uani d . 1 H H2B 0.5467 0.1729 0.5211 0.052 Uiso calc R 1 C C3 0.4522(4) 0.3372(3) 0.6233(2) 0.0435(8) Uani d . 1 H H3B 0.5464 0.4015 0.6087 0.052 Uiso calc R 1 C C4 0.4006(4) 0.1088(3) 0.7916(2) 0.0388(7) Uani d . 1 C C5 0.3979(4) -0.0332(3) 0.7776(3) 0.0479(8) Uani d . 1 H H5B 0.4261 -0.0932 0.7152 0.057 Uiso calc R 1 C C6 0.3527(5) -0.0842(4) 0.8574(3) 0.0589(10) Uani d . 1 H H6A 0.3497 -0.1795 0.8500 0.071 Uiso calc R 1 C C7 0.3124(4) 0.0069(4) 0.9475(3) 0.0578(10) Uani d . 1 H H7A 0.2817 -0.0248 1.0029 0.069 Uiso calc R 1 C C8 0.3181(4) 0.1471(4) 0.9550(3) 0.0539(9) Uani d . 1 H H8A 0.2899 0.2086 1.0167 0.065 Uiso calc R 1 C C9 0.3068(4) 0.1464(3) 0.4479(2) 0.0415(8) Uani d . 1 C C10 0.1672(4) 0.0362(3) 0.4222(3) 0.0513(9) Uani d . 1 H H10A 0.1478 -0.0208 0.4644 0.062 Uiso calc R 1 C C11 0.0569(5) 0.0117(4) 0.3332(3) 0.0625(10) Uani d . 1 H H11A -0.0397 -0.0612 0.3146 0.075 Uiso calc R 1 C C12 0.0912(5) 0.0962(4) 0.2719(3) 0.0583(10) Uani d . 1 H H12A 0.0182 0.0819 0.2112 0.070 Uiso calc R 1 C C13 0.2343(5) 0.2014(4) 0.3016(3) 0.0557(9) Uani d . 1 H H13A 0.2579 0.2573 0.2589 0.067 Uiso calc R 1 C C14 0.2925(4) 0.3986(3) 0.6281(2) 0.0407(8) Uani d . 1 C C15 0.2940(5) 0.5330(3) 0.6216(3) 0.0561(9) Uani d . 1 H H15A 0.3945 0.5878 0.6131 0.067 Uiso calc R 1 C C16 0.1466(6) 0.5843(4) 0.6277(3) 0.0683(11) Uani d . 1 H H16A 0.1453 0.6745 0.6236 0.082 Uiso calc R 1 C C17 0.0008(5) 0.5011(4) 0.6399(3) 0.0669(11) Uani d . 1 H H17A -0.1013 0.5337 0.6449 0.080 Uiso calc R 1 C C18 0.0088(5) 0.3687(4) 0.6447(3) 0.0587(9) Uani d . 1 H H18A -0.0912 0.3117 0.6514 0.070 Uiso calc R 1 C C19 0.5967(4) 0.4186(3) 0.8071(2) 0.0459(8) Uani d . 1 C C20 0.6959(4) 0.3814(3) 0.8878(2) 0.0401(8) Uani d . 1 C C21 0.7149(4) 0.4693(3) 0.9926(3) 0.0479(8) Uani d . 1 H H21A 0.6591 0.5457 1.0118 0.057 Uiso calc R 1 C C22 0.8166(5) 0.4436(4) 1.0685(3) 0.0590(10) Uani d . 1 H H22A 0.8246 0.5001 1.1392 0.071 Uiso calc R 1 C C23 0.9049(5) 0.3364(4) 1.0408(3) 0.0632(10) Uani d . 1 H H23A 0.9764 0.3222 1.0921 0.076 Uiso calc R 1 C C24 0.8890(4) 0.2488(4) 0.9372(3) 0.0565(9) Uani d . 1 H H24A 0.9488 0.1749 0.9185 0.068 Uiso calc R 1 C C25 0.7838(4) 0.2708(3) 0.8608(3) 0.0465(8) Uani d . 1 H H25A 0.7721 0.2107 0.7908 0.056 Uiso calc R 1 N N1 0.5004(3) 0.3120(2) 0.72264(18) 0.0417(6) Uani d . 1 N N2 0.3949(3) 0.0892(3) 0.6083(2) 0.0443(7) Uani d . 1 N N3 0.3616(3) 0.1996(3) 0.8789(2) 0.0448(7) Uani d . 1 N N4 0.3427(3) 0.2286(3) 0.3890(2) 0.0505(7) Uani d . 1 N N5 0.1514(4) 0.3169(3) 0.6402(2) 0.0522(7) Uani d . 1 O O1 0.6116(3) 0.5423(2) 0.80961(17) 0.0641(7) Uani d . 1 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 C1 0.0382(18) 0.0368(17) 0.0389(18) 0.0068(14) 0.0009(14) 0.0105(15) C2 0.0434(19) 0.0461(18) 0.0357(18) 0.0063(15) 0.0033(15) 0.0092(15) C3 0.047(2) 0.0443(18) 0.0369(18) 0.0011(15) 0.0008(15) 0.0160(14) C4 0.0349(17) 0.0384(17) 0.0388(18) 0.0022(14) -0.0060(14) 0.0119(15) C5 0.053(2) 0.0417(19) 0.047(2) 0.0091(16) -0.0030(16) 0.0156(16) C6 0.069(3) 0.043(2) 0.063(2) 0.0028(18) -0.011(2) 0.0245(19) C7 0.061(2) 0.060(2) 0.053(2) -0.0052(19) -0.0043(18) 0.0316(19) C8 0.056(2) 0.064(2) 0.042(2) 0.0058(18) 0.0062(17) 0.0199(18) C9 0.048(2) 0.0400(18) 0.0363(18) 0.0123(16) 0.0086(15) 0.0102(15) C10 0.052(2) 0.051(2) 0.048(2) 0.0009(17) 0.0044(17) 0.0180(17) C11 0.050(2) 0.064(2) 0.059(2) -0.0017(18) -0.0064(19) 0.009(2) C12 0.054(2) 0.063(2) 0.050(2) 0.0173(19) -0.0115(18) 0.0091(19) C13 0.069(3) 0.055(2) 0.046(2) 0.016(2) -0.0006(19) 0.0208(18) C14 0.048(2) 0.0377(18) 0.0313(17) 0.0019(15) -0.0016(14) 0.0093(14) C15 0.065(2) 0.041(2) 0.057(2) -0.0011(18) -0.0061(18) 0.0183(17) C16 0.084(3) 0.044(2) 0.077(3) 0.017(2) -0.013(2) 0.024(2) C17 0.067(3) 0.061(2) 0.066(3) 0.023(2) -0.003(2) 0.008(2) C18 0.054(2) 0.058(2) 0.064(2) 0.0099(19) 0.0120(19) 0.0217(19) C19 0.049(2) 0.0395(19) 0.0426(19) -0.0007(16) 0.0011(16) 0.0103(15) C20 0.0380(18) 0.0421(18) 0.0351(18) -0.0026(15) -0.0020(14) 0.0129(15) C21 0.046(2) 0.0458(19) 0.046(2) 0.0005(16) 0.0052(16) 0.0133(16) C22 0.065(2) 0.063(2) 0.0367(19) -0.005(2) -0.0083(18) 0.0106(17) C23 0.059(2) 0.070(3) 0.058(3) -0.002(2) -0.0115(19) 0.030(2) C24 0.050(2) 0.053(2) 0.067(3) 0.0056(17) -0.0057(19) 0.0248(19) C25 0.0432(19) 0.049(2) 0.0407(19) -0.0006(16) 0.0011(15) 0.0117(15) N1 0.0479(16) 0.0360(14) 0.0337(14) -0.0023(12) -0.0069(12) 0.0095(11) N2 0.0532(17) 0.0366(14) 0.0405(16) 0.0062(12) 0.0007(13) 0.0117(12) N3 0.0463(16) 0.0445(15) 0.0422(16) 0.0042(13) 0.0040(13) 0.0157(13) N4 0.0567(18) 0.0476(16) 0.0436(16) 0.0035(14) 0.0008(14) 0.0152(14) N5 0.0569(19) 0.0499(17) 0.0538(18) 0.0121(15) 0.0124(15) 0.0213(14) O1 0.0910(19) 0.0381(14) 0.0542(15) -0.0024(13) -0.0156(13) 0.0157(11) 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_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle N2 C1 N1 114.6(3) N2 C1 C4 122.2(3) N1 C1 C4 122.7(3) N2 C2 C9 113.5(3) N2 C2 C3 105.2(2) C9 C2 C3 114.1(2) N2 C2 H2B 107.9 C9 C2 H2B 107.9 C3 C2 H2B 107.9 N1 C3 C14 111.5(2) N1 C3 C2 98.9(2) C14 C3 C2 115.8(3) N1 C3 H3B 110.1 C14 C3 H3B 110.1 C2 C3 H3B 110.1 N3 C4 C5 123.3(3) N3 C4 C1 116.2(3) C5 C4 C1 120.3(3) C6 C5 C4 118.7(3) C6 C5 H5B 120.6 C4 C5 H5B 120.6 C7 C6 C5 118.9(3) C7 C6 H6A 120.5 C5 C6 H6A 120.5 C6 C7 C8 118.6(3) C6 C7 H7A 120.7 C8 C7 H7A 120.7 N3 C8 C7 123.8(3) N3 C8 H8A 118.1 C7 C8 H8A 118.1 N4 C9 C10 123.1(3) N4 C9 C2 114.1(3) C10 C9 C2 122.8(3) C11 C10 C9 118.8(3) C11 C10 H10A 120.6 C9 C10 H10A 120.6 C10 C11 C12 118.9(3) C10 C11 H11A 120.5 C12 C11 H11A 120.5 C13 C12 C11 118.8(3) C13 C12 H12A 120.6 C11 C12 H12A 120.6 N4 C13 C12 123.3(3) N4 C13 H13A 118.3 C12 C13 H13A 118.3 N5 C14 C15 122.2(3) N5 C14 C3 116.2(3) C15 C14 C3 121.6(3) C16 C15 C14 119.3(3) C16 C15 H15A 120.3 C14 C15 H15A 120.3 C15 C16 C17 119.0(3) C15 C16 H16A 120.5 C17 C16 H16A 120.5 C18 C17 C16 118.4(4) C18 C17 H17A 120.8 C16 C17 H17A 120.8 N5 C18 C17 123.8(4) N5 C18 H18A 118.1 C17 C18 H18A 118.1 O1 C19 N1 119.1(3) O1 C19 C20 121.1(3) N1 C19 C20 119.5(3) C25 C20 C21 118.8(3) C25 C20 C19 122.2(3) C21 C20 C19 118.7(3) C22 C21 C20 120.1(3) C22 C21 H21A 119.9 C20 C21 H21A 119.9 C23 C22 C21 120.6(3) C23 C22 H22A 119.7 C21 C22 H22A 119.7 C22 C23 C24 120.2(3) C22 C23 H23A 119.9 C24 C23 H23A 119.9 C23 C24 C25 119.9(3) C23 C24 H24A 120.1 C25 C24 H24A 120.1 C24 C25 C20 120.4(3) C24 C25 H25A 119.8 C20 C25 H25A 119.8 C19 N1 C1 132.2(3) C19 N1 C3 121.1(2) C1 N1 C3 106.6(2) C1 N2 C2 107.4(2) C4 N3 C8 116.6(3) C9 N4 C13 117.1(3) C14 N5 C18 117.3(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 N2 1.267(4) C1 N1 1.416(4) C1 C4 1.476(4) C2 N2 1.473(4) C2 C9 1.509(4) C2 C3 1.552(4) C2 H2B 0.9800 C3 N1 1.477(4) C3 C14 1.509(4) C3 H3B 0.9800 C4 N3 1.330(4) C4 C5 1.380(4) C5 C6 1.371(4) C5 H5B 0.9300 C6 C7 1.361(5) C6 H6A 0.9300 C7 C8 1.377(4) C7 H7A 0.9300 C8 N3 1.332(4) C8 H8A 0.9300 C9 N4 1.327(4) C9 C10 1.373(4) C10 C11 1.369(4) C10 H10A 0.9300 C11 C12 1.369(5) C11 H11A 0.9300 C12 C13 1.362(5) C12 H12A 0.9300 C13 N4 1.340(4) C13 H13A 0.9300 C14 N5 1.331(4) C14 C15 1.384(4) C15 C16 1.363(5) C15 H15A 0.9300 C16 C17 1.368(5) C16 H16A 0.9300 C17 C18 1.369(5) C17 H17A 0.9300 C18 N5 1.331(4) C18 H18A 0.9300 C19 O1 1.222(3) C19 N1 1.366(4) C19 C20 1.483(4) C20 C25 1.383(4) C20 C21 1.385(4) C21 C22 1.381(4) C21 H21A 0.9300 C22 C23 1.358(5) C22 H22A 0.9300 C23 C24 1.373(5) C23 H23A 0.9300 C24 C25 1.384(4) C24 H24A 0.9300 C25 H25A 0.9300 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 C13 H13A O1 2_666 0.93 2.57 3.469(5) 162.6 C15 H15A N4 2_666 0.93 2.56 3.483(5) 171.1 C5 H5B N4 2_656 0.93 2.69 3.515(5) 149.0 C21 H21A N3 2_667 0.93 2.56 3.413(5) 153.1 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 N2 C2 C3 N1 25.5(3) C9 C2 C3 N1 150.6(3) N2 C2 C3 C14 -93.6(3) C9 C2 C3 C14 31.4(4) N2 C1 C4 N3 -144.7(3) N1 C1 C4 N3 26.8(4) N2 C1 C4 C5 31.4(4) N1 C1 C4 C5 -157.1(3) N3 C4 C5 C6 0.0(5) C1 C4 C5 C6 -175.8(3) C4 C5 C6 C7 -0.1(5) C5 C6 C7 C8 0.2(5) C6 C7 C8 N3 -0.3(5) N2 C2 C9 N4 -178.9(3) C3 C2 C9 N4 60.5(4) N2 C2 C9 C10 0.0(4) C3 C2 C9 C10 -120.6(3) N4 C9 C10 C11 -1.8(5) C2 C9 C10 C11 179.4(3) C9 C10 C11 C12 1.2(5) C10 C11 C12 C13 0.2(5) C11 C12 C13 N4 -1.1(5) N1 C3 C14 N5 -62.1(3) C2 C3 C14 N5 49.9(4) N1 C3 C14 C15 117.1(3) C2 C3 C14 C15 -130.9(3) N5 C14 C15 C16 0.0(5) C3 C14 C15 C16 -179.2(3) C14 C15 C16 C17 -0.1(5) C15 C16 C17 C18 -0.5(6) C16 C17 C18 N5 1.4(6) O1 C19 C20 C25 -132.3(3) N1 C19 C20 C25 41.0(4) O1 C19 C20 C21 41.1(5) N1 C19 C20 C21 -145.6(3) C25 C20 C21 C22 -1.7(5) C19 C20 C21 C22 -175.4(3) C20 C21 C22 C23 3.0(5) C21 C22 C23 C24 -2.4(6) C22 C23 C24 C25 0.6(5) C23 C24 C25 C20 0.7(5) C21 C20 C25 C24 -0.2(5) C19 C20 C25 C24 173.3(3) O1 C19 N1 C1 -168.1(3) C20 C19 N1 C1 18.4(5) O1 C19 N1 C3 16.1(5) C20 C19 N1 C3 -157.4(3) N2 C1 N1 C19 -160.5(3) C4 C1 N1 C19 27.4(5) N2 C1 N1 C3 15.7(3) C4 C1 N1 C3 -156.4(3) C14 C3 N1 C19 -85.2(3) C2 C3 N1 C19 152.4(3) C14 C3 N1 C1 98.1(3) C2 C3 N1 C1 -24.3(3) N1 C1 N2 C2 2.3(3) C4 C1 N2 C2 174.4(3) C9 C2 N2 C1 -143.8(3) C3 C2 N2 C1 -18.3(3) C5 C4 N3 C8 -0.1(4) C1 C4 N3 C8 175.9(3) C7 C8 N3 C4 0.2(5) C10 C9 N4 C13 0.9(5) C2 C9 N4 C13 179.8(3) C12 C13 N4 C9 0.6(5) C15 C14 N5 C18 0.7(4) C3 C14 N5 C18 180.0(3) C17 C18 N5 C14 -1.5(5) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139072545