#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/69/2206935.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_2206935 loop_ _publ_author_name 'Gui-Yun Duan' 'Ya-Wei Sun' 'Jun-Zhi Liu' 'Jian-Wu Wang' _publ_section_title ; Bis(benzimidazol-2-yl)methane ; _journal_coeditor_code CV6580 _journal_issue 10 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3476 _journal_page_last o3477 _journal_paper_doi 10.1107/S1600536805030229 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C15 H12 N4' _chemical_formula_moiety 'C15 H12 N4' _chemical_formula_sum 'C15 H12 N4' _chemical_formula_weight 248.29 _chemical_name_systematic ; Bis(benzimidazol-2-yl)methane ; _space_group_IT_number 88 _symmetry_cell_setting tetragonal _symmetry_space_group_name_Hall '-I 4ad' _symmetry_space_group_name_H-M 'I 41/a :2' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 16 _cell_length_a 18.296(4) _cell_length_b 18.296(4) _cell_length_c 15.728(3) _cell_measurement_reflns_used 4441 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 25.832 _cell_measurement_theta_min 2.225 _cell_volume 5264.8(19) _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction SAINT _computing_molecular_graphics 'SHELXTL (Bruker, 1999)' _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 0.987 _diffrn_measured_fraction_theta_max 0.987 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \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 0.0353 _diffrn_reflns_av_sigmaI/netI 0.0244 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 10662 _diffrn_reflns_theta_full 25.05 _diffrn_reflns_theta_max 25.05 _diffrn_reflns_theta_min 2.81 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_T_max 0.9791 _exptl_absorpt_correction_T_min 0.9500 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.253 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 2080 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.27 _refine_diff_density_max 0.201 _refine_diff_density_min -0.157 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 172 _refine_ls_number_reflns 2307 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.000 _refine_ls_R_factor_all 0.0555 _refine_ls_R_factor_gt 0.0416 _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^)+(0.075P)^2^+1.5659P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1159 _refine_ls_wR_factor_ref 0.1303 _reflns_number_gt 1798 _reflns_number_total 2307 _reflns_threshold_expression I>2\s(I) _cod_data_source_file cv6580.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal' 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 'Tetragonal' changed to 'tetragonal' 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 5264.6(18) _cod_original_sg_symbol_H-M I41/a _cod_database_code 2206935 _cod_database_fobs_code 2206935 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-y+3/4, x+1/4, z+1/4' 'y+3/4, -x+3/4, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1/2, z+1' '-y+5/4, x+3/4, z+3/4' 'y+5/4, -x+5/4, z+5/4' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'y-3/4, -x-1/4, -z-1/4' '-y-3/4, x-3/4, -z-3/4' '-x+1/2, -y+1/2, -z+1/2' 'x, y+1/2, -z' 'y-1/4, -x+1/4, -z+1/4' '-y-1/4, x-1/4, -z-1/4' 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 0.57166(10) 0.30536(8) 0.09757(10) 0.0708(5) Uani d . 1 N N2 0.58129(8) 0.42431(7) 0.11565(8) 0.0560(4) Uani d . 1 N H2A 0.5790 0.4704 0.1049 0.067 Uiso calc R 1 H N3 0.41074(8) 0.42962(7) -0.06625(8) 0.0578(4) Uani d . 1 N N4 0.41095(8) 0.32348(7) 0.00088(8) 0.0563(4) Uani d . 1 N H4A 0.4271 0.2856 0.0273 0.068 Uiso calc R 1 H C1 0.60520(9) 0.39271(9) 0.18957(11) 0.0563(4) Uani d . 1 C C2 0.63143(12) 0.42248(11) 0.26529(12) 0.0767(6) Uani d . 1 C H2 0.6354 0.4727 0.2728 0.092 Uiso calc R 1 H C3 0.65094(15) 0.37490(13) 0.32774(14) 0.0954(8) Uani d . 1 C H3 0.6693 0.3931 0.3786 0.114 Uiso calc R 1 H C4 0.64421(17) 0.30066(14) 0.31753(17) 0.1144(10) Uani d . 1 C H4 0.6575 0.2699 0.3620 0.137 Uiso calc R 1 H C5 0.61850(17) 0.27091(12) 0.24371(17) 0.1101(10) Uani d . 1 C H5 0.6142 0.2206 0.2372 0.132 Uiso calc R 1 H C6 0.59899(11) 0.31847(10) 0.17871(12) 0.0669(5) Uani d . 1 C C7 0.56216(9) 0.37014(8) 0.06352(10) 0.0514(4) Uani d . 1 C C8 0.53220(10) 0.38310(11) -0.02331(10) 0.0635(5) Uani d . 1 C H8A 0.5526 0.3470 -0.0617 0.076 Uiso calc R 1 H H8B 0.5481 0.4309 -0.0427 0.076 Uiso calc R 1 H C9 0.45082(9) 0.37953(8) -0.02848(9) 0.0511(4) Uani d . 1 C C10 0.33919(10) 0.40476(9) -0.06135(10) 0.0557(4) Uani d . 1 C C11 0.27477(12) 0.43470(11) -0.09232(13) 0.0752(6) Uani d . 1 C H11 0.2745 0.4795 -0.1203 0.090 Uiso calc R 1 H C12 0.21142(12) 0.39574(13) -0.08007(14) 0.0813(6) Uani d . 1 C H12 0.1675 0.4146 -0.1000 0.098 Uiso calc R 1 H C13 0.21165(12) 0.32914(13) -0.03878(14) 0.0782(6) Uani d . 1 C H13 0.1679 0.3040 -0.0321 0.094 Uiso calc R 1 H C14 0.27489(11) 0.29906(11) -0.00732(12) 0.0699(5) Uani d . 1 C H14 0.2748 0.2544 0.0208 0.084 Uiso calc R 1 H C15 0.33900(9) 0.33830(9) -0.01940(9) 0.0538(4) Uani d . 1 C 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 0.1020(12) 0.0503(8) 0.0599(9) 0.0033(8) -0.0166(8) -0.0050(7) N2 0.0746(9) 0.0432(7) 0.0503(8) -0.0022(6) -0.0062(6) 0.0046(6) N3 0.0764(10) 0.0527(8) 0.0442(7) -0.0072(7) -0.0072(6) 0.0067(6) N4 0.0748(9) 0.0468(7) 0.0472(8) 0.0037(6) 0.0050(6) 0.0072(6) C1 0.0640(10) 0.0522(9) 0.0527(10) -0.0008(7) -0.0092(8) 0.0029(7) C2 0.0981(15) 0.0647(11) 0.0672(12) -0.0069(10) -0.0244(11) -0.0038(9) C3 0.126(2) 0.0895(16) 0.0703(14) -0.0084(14) -0.0436(13) 0.0050(11) C4 0.172(3) 0.0834(16) 0.0881(17) -0.0068(16) -0.0636(18) 0.0252(13) C5 0.173(3) 0.0557(12) 0.1017(19) -0.0041(13) -0.0560(18) 0.0158(12) C6 0.0873(13) 0.0515(10) 0.0618(11) 0.0012(8) -0.0199(9) 0.0017(8) C7 0.0573(9) 0.0510(9) 0.0460(9) 0.0001(7) 0.0037(7) -0.0005(7) C8 0.0739(11) 0.0769(12) 0.0398(9) -0.0046(9) 0.0032(8) 0.0018(8) C9 0.0706(10) 0.0504(9) 0.0324(7) -0.0023(7) 0.0006(7) -0.0002(6) C10 0.0725(11) 0.0548(9) 0.0397(8) -0.0040(8) -0.0025(7) -0.0037(7) C11 0.0876(14) 0.0743(12) 0.0639(12) 0.0041(10) -0.0142(10) 0.0057(9) C12 0.0713(13) 0.1036(17) 0.0690(13) 0.0044(11) -0.0093(10) -0.0094(12) C13 0.0715(13) 0.0945(15) 0.0686(13) -0.0101(11) 0.0116(10) -0.0168(11) C14 0.0827(13) 0.0652(11) 0.0618(11) -0.0112(9) 0.0167(10) -0.0051(9) C15 0.0702(11) 0.0519(9) 0.0393(8) -0.0007(8) 0.0067(7) -0.0075(7) 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 C7 N1 C6 105.43(14) yes C7 N2 C1 106.98(13) yes C7 N2 H2A 126.5 ? C1 N2 H2A 126.5 ? C9 N3 C10 105.81(13) yes C9 N4 C15 106.79(13) yes C9 N4 H4A 126.6 ? C15 N4 H4A 126.6 ? N2 C1 C6 106.58(14) ? N2 C1 C2 132.04(16) ? C6 C1 C2 121.38(16) ? C3 C2 C1 117.20(19) ? C3 C2 H2 121.4 ? C1 C2 H2 121.4 ? C2 C3 C4 121.7(2) ? C2 C3 H3 119.2 ? C4 C3 H3 119.2 ? C5 C4 C3 121.6(2) ? C5 C4 H4 119.2 ? C3 C4 H4 119.2 ? C4 C5 C6 117.7(2) ? C4 C5 H5 121.2 ? C6 C5 H5 121.2 ? C1 C6 C5 120.44(18) ? C1 C6 N1 108.32(14) ? C5 C6 N1 131.25(18) ? N1 C7 N2 112.69(14) ? N1 C7 C8 124.49(15) ? N2 C7 C8 122.81(15) ? C7 C8 C9 114.19(14) yes C7 C8 H8A 108.7 ? C9 C8 H8A 108.7 ? C7 C8 H8B 108.7 ? C9 C8 H8B 108.7 ? H8A C8 H8B 107.6 ? N3 C9 N4 112.65(15) ? N3 C9 C8 123.38(14) ? N4 C9 C8 123.89(15) ? C15 C10 C11 120.81(17) ? C15 C10 N3 108.47(14) ? C11 C10 N3 130.70(16) ? C12 C11 C10 117.53(19) ? C12 C11 H11 121.2 ? C10 C11 H11 121.2 ? C11 C12 C13 121.4(2) ? C11 C12 H12 119.3 ? C13 C12 H12 119.3 ? C14 C13 C12 121.72(19) ? C14 C13 H13 119.1 ? C12 C13 H13 119.1 ? C13 C14 C15 117.08(19) ? C13 C14 H14 121.5 ? C15 C14 H14 121.5 ? N4 C15 C10 106.27(14) ? N4 C15 C14 132.23(17) ? C10 C15 C14 121.46(17) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C7 1.312(2) yes N1 C6 1.391(2) yes N2 C7 1.333(2) yes N2 C1 1.370(2) yes N2 H2A 0.8600 ? N3 C9 1.315(2) yes N3 C10 1.388(2) yes N4 C9 1.340(2) yes N4 C15 1.381(2) yes N4 H4A 0.8600 ? C1 C6 1.374(2) ? C1 C2 1.395(2) ? C2 C3 1.360(3) ? C2 H2 0.9300 ? C3 C4 1.373(3) ? C3 H3 0.9300 ? C4 C5 1.366(4) ? C4 H4 0.9300 ? C5 C6 1.389(3) ? C5 H5 0.9300 ? C7 C8 1.491(2) yes C8 C9 1.493(2) yes C8 H8A 0.9700 ? C8 H8B 0.9700 ? C10 C15 1.384(2) ? C10 C11 1.388(3) ? C11 C12 1.374(3) ? C11 H11 0.9300 ? C12 C13 1.381(3) ? C12 H12 0.9300 ? C13 C14 1.373(3) ? C13 H13 0.9300 ? C14 C15 1.388(2) ? C14 H14 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 N2 H2A N3 9_665 0.86 1.94 2.7869(18) 169 N4 H4A N1 6_554 0.86 2.00 2.823(2) 160 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 C7 N2 C1 C6 -0.26(19) C7 N2 C1 C2 -179.9(2) N2 C1 C2 C3 179.9(2) C6 C1 C2 C3 0.3(3) C1 C2 C3 C4 -1.0(4) C2 C3 C4 C5 0.9(5) C3 C4 C5 C6 -0.2(5) N2 C1 C6 C5 -179.3(2) C2 C1 C6 C5 0.4(3) N2 C1 C6 N1 0.4(2) C2 C1 C6 N1 -179.91(18) C4 C5 C6 C1 -0.4(4) C4 C5 C6 N1 179.9(3) C7 N1 C6 C1 -0.4(2) C7 N1 C6 C5 179.3(3) C6 N1 C7 N2 0.2(2) C6 N1 C7 C8 -178.84(16) C1 N2 C7 N1 0.0(2) C1 N2 C7 C8 179.10(15) N1 C7 C8 C9 81.0(2) N2 C7 C8 C9 -97.94(19) C10 N3 C9 N4 0.06(17) C10 N3 C9 C8 176.91(14) C15 N4 C9 N3 -0.03(17) C15 N4 C9 C8 -176.87(14) C7 C8 C9 N3 131.44(16) C7 C8 C9 N4 -52.1(2) C9 N3 C10 C15 -0.06(17) C9 N3 C10 C11 -178.29(18) C15 C10 C11 C12 -0.3(3) N3 C10 C11 C12 177.74(17) C10 C11 C12 C13 -0.2(3) C11 C12 C13 C14 0.7(3) C12 C13 C14 C15 -0.5(3) C9 N4 C15 C10 -0.01(16) C9 N4 C15 C14 177.71(17) C11 C10 C15 N4 178.48(15) N3 C10 C15 N4 0.04(17) C11 C10 C15 C14 0.5(2) N3 C10 C15 C14 -177.98(14) C13 C14 C15 N4 -177.49(17) C13 C14 C15 C10 -0.1(2) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 229071 2 PubChem 260968