#------------------------------------------------------------------------------ #$Date: 2025-08-19 12:52:15 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301804 $ #$URL: svn://www.crystallography.net/cod/cif/2/21/45/2214528.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_2214528 loop_ _publ_author_name 'Siero\'n, Les\/law' _publ_section_title ; Benzimidazolium perchlorate ; _journal_coeditor_code BQ2032 _journal_issue 8 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3585 _journal_page_last o3585 _journal_paper_doi 10.1107/S1600536807035428 _journal_volume 63 _journal_year 2007 _chemical_formula_iupac 'C7 H7 N2 + , Cl O4 -' _chemical_formula_moiety 'C7 H7 N2 + , Cl O4 -' _chemical_formula_sum 'C7 H7 Cl N2 O4' _chemical_formula_weight 218.60 _chemical_name_systematic 'Benzimidazolium perchlorate' _space_group_IT_number 29 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2c -2ac' _symmetry_space_group_name_H-M 'P c a 21' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 9.9885(2) _cell_length_b 9.05090(10) _cell_length_c 19.0182(3) _cell_measurement_reflns_used 11107 _cell_measurement_temperature 297 _cell_measurement_theta_max 29.0 _cell_measurement_theta_min 3.0 _cell_volume 1719.34(5) _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, 2006)' _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2006)' _computing_data_reduction 'CrysAlis RED' _computing_molecular_graphics 'SHELXTL and Mercury (Macrae et al., 2006)' _computing_publication_material 'PLATON (Spek, 2003)' _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 2001)' _diffrn_ambient_temperature 297 _diffrn_detector_area_resol_mean 8.2356 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device '4-circle goniometer' _diffrn_measurement_device_type 'Kuma KM4 CCD area-detector' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0179 _diffrn_reflns_av_sigmaI/netI 0.0117 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 16719 _diffrn_reflns_reduction_process ; ; _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 3.04 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.434 _exptl_absorpt_correction_T_max 0.974 _exptl_absorpt_correction_T_min 0.781 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(CrysAlis RED; Oxford Diffraction, 2006)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.689 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 896 _exptl_crystal_size_max 0.600 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.060 _refine_diff_density_max 0.867 _refine_diff_density_min -0.403 _refine_ls_abs_structure_details 'Flack (1983), with 1462 Friedel pairs' _refine_ls_abs_structure_Flack 0.04(6) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 253 _refine_ls_number_reflns 2923 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.063 _refine_ls_R_factor_all 0.0438 _refine_ls_R_factor_gt 0.0405 _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^)+(0.0829P)^2^+0.431P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1083 _refine_ls_wR_factor_ref 0.1121 _reflns_number_gt 2676 _reflns_number_total 2923 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bq2032.cif _cod_data_source_block I _cod_database_code 2214528 _cod_database_fobs_code 2214528 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,1/2+z 3 1/2-x,y,1/2+z 4 1/2+x,-y,z 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 0.0363(16) 0.0406(15) 0.0346(18) -0.0029(13) 0.0032(15) 0.0083(13) N3 0.0473(17) 0.0253(14) 0.0495(16) 0.0056(12) -0.0026(14) -0.0043(12) C2 0.0382(16) 0.047(2) 0.0436(17) 0.0074(17) -0.0005(15) -0.0034(16) C4 0.045(2) 0.054(3) 0.0339(18) -0.0130(18) 0.0038(16) 0.0057(18) C5 0.038(2) 0.065(2) 0.037(2) -0.0036(18) 0.0033(18) -0.0060(17) C6 0.0455(19) 0.039(2) 0.045(2) 0.0018(16) -0.0006(16) -0.0139(17) C7 0.0388(19) 0.0317(17) 0.052(2) -0.0025(14) -0.0051(16) -0.0034(16) C8 0.0323(18) 0.037(2) 0.0324(17) -0.0023(15) -0.0012(14) 0.0060(14) C9 0.0382(18) 0.0243(16) 0.0421(18) -0.0040(14) -0.0070(15) -0.0011(15) N11 0.0297(15) 0.0434(15) 0.0388(18) 0.0000(13) 0.0066(15) -0.0014(14) N13 0.0439(16) 0.0274(14) 0.0490(15) 0.0046(12) -0.0033(13) -0.0019(12) C12 0.0366(16) 0.050(2) 0.0391(16) 0.0068(16) 0.0030(15) -0.0066(15) C14 0.0400(19) 0.034(2) 0.0402(19) -0.0049(15) -0.0035(15) 0.0091(16) C15 0.038(2) 0.068(3) 0.031(2) 0.0022(18) 0.0044(18) -0.0073(19) C16 0.043(2) 0.050(2) 0.049(2) 0.0070(18) -0.0005(17) -0.0135(18) C17 0.046(2) 0.0269(16) 0.0463(18) -0.0016(14) -0.0029(16) -0.0004(14) C18 0.0352(18) 0.0297(19) 0.0356(18) -0.0004(14) -0.0069(15) -0.0008(14) C19 0.0330(18) 0.0338(18) 0.0295(15) 0.0078(14) -0.0050(13) -0.0033(14) Cl1 0.0330(4) 0.0262(4) 0.0425(5) -0.0005(3) 0.0064(4) -0.0017(4) O1 0.0638(18) 0.0384(16) 0.0648(18) 0.0065(13) 0.0235(15) -0.0125(13) O2 0.094(2) 0.0277(15) 0.0718(19) -0.0002(12) 0.0220(16) 0.0107(13) O3 0.0322(16) 0.0402(17) 0.102(4) -0.0037(11) 0.0316(18) -0.0026(14) O4 0.068(2) 0.077(2) 0.070(2) 0.0044(19) -0.0172(18) -0.0132(19) Cl2 0.0340(4) 0.0273(4) 0.0436(5) 0.0016(3) 0.0077(4) 0.0039(4) O11 0.0701(18) 0.0360(15) 0.0600(16) -0.0022(13) 0.0253(15) 0.0144(13) O12 0.099(2) 0.0226(14) 0.080(2) -0.0070(13) 0.0311(17) -0.0102(13) O13 0.0418(17) 0.0396(17) 0.081(3) 0.0061(11) 0.0095(18) 0.0030(13) O14 0.068(2) 0.089(2) 0.066(2) -0.0168(19) -0.0248(18) 0.022(2) 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_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy N N1 0.1711(3) 1.0228(3) 0.83955(19) 0.0372(9) Uani . . 1.000 N N3 0.1090(3) 0.8084(3) 0.87538(15) 0.0407(9) Uani . . 1.000 C C2 0.1928(3) 0.8817(4) 0.83387(18) 0.0429(10) Uani . . 1.000 C C4 -0.0706(4) 0.8899(5) 0.96160(19) 0.0443(13) Uani . . 1.000 C C5 -0.1273(4) 1.0173(5) 0.9862(3) 0.0467(12) Uani . . 1.000 C C6 -0.0876(4) 1.1586(4) 0.9630(2) 0.0432(11) Uani . . 1.000 C C7 0.0100(3) 1.1771(4) 0.9134(2) 0.0408(11) Uani . . 1.000 C C8 0.0692(4) 1.0482(4) 0.88770(18) 0.0339(11) Uani . . 1.000 C C9 0.0286(3) 0.9077(3) 0.91156(19) 0.0349(10) Uani . . 1.000 N N11 0.0702(3) 0.4754(4) 0.69468(19) 0.0373(9) Uani . . 1.000 N N13 0.1382(3) 0.6899(3) 0.66146(16) 0.0401(9) Uani . . 1.000 C C12 0.0526(3) 0.6176(4) 0.70226(18) 0.0419(10) Uani . . 1.000 C C14 0.3180(4) 0.6058(4) 0.57613(19) 0.0381(11) Uani . . 1.000 C C15 0.3723(4) 0.4758(5) 0.5490(2) 0.0457(14) Uani . . 1.000 C C16 0.3277(4) 0.3378(5) 0.5725(2) 0.0473(12) Uani . . 1.000 C C17 0.2294(4) 0.3210(4) 0.62179(18) 0.0397(10) Uani . . 1.000 C C18 0.1730(4) 0.4499(4) 0.64646(18) 0.0335(11) Uani . . 1.000 C C19 0.2161(3) 0.5872(4) 0.62590(17) 0.0321(10) Uani . . 1.000 Cl Cl1 0.44447(8) 0.96264(9) 0.68820(4) 0.0339(3) Uani . . 1.000 O O1 0.3939(3) 1.0716(3) 0.73581(17) 0.0557(10) Uani . . 1.000 O O2 0.4461(3) 0.8223(3) 0.72205(16) 0.0645(10) Uani . . 1.000 O O3 0.5778(3) 1.0008(3) 0.6670(2) 0.0581(15) Uani . . 1.000 O O4 0.3618(3) 0.9553(4) 0.6270(2) 0.0717(12) Uani . . 1.000 Cl Cl2 0.29983(8) 0.46265(9) 0.84884(4) 0.0350(3) Uani . . 1.000 O O11 0.3484(3) 0.5709(3) 0.79958(17) 0.0554(9) Uani . . 1.000 O O12 0.2998(4) 0.3209(3) 0.81592(16) 0.0672(11) Uani . . 1.000 O O13 0.1659(3) 0.4988(3) 0.8680(2) 0.0541(13) Uani . . 1.000 O O14 0.3814(3) 0.4610(4) 0.9092(2) 0.0743(12) Uani . . 1.000 H H1 0.21380 1.09040 0.81700 0.0450 Uiso . R 1.000 H H2 0.25720 0.83860 0.80510 0.0520 Uiso calc R 1.000 H H3 0.10520 0.71380 0.87920 0.0490 Uiso . R 1.000 H H4 -0.09700 0.79720 0.97750 0.0530 Uiso calc R 1.000 H H5 -0.19490 1.01040 1.01960 0.0560 Uiso calc R 1.000 H H6 -0.12900 1.24150 0.98200 0.0520 Uiso calc R 1.000 H H7 0.03560 1.27020 0.89760 0.0490 Uiso calc R 1.000 H H11 0.02560 0.40790 0.71620 0.0450 Uiso . R 1.000 H H12 -0.01030 0.66140 0.73170 0.0500 Uiso calc R 1.000 H H13 0.14440 0.78440 0.65780 0.0480 Uiso . R 1.000 H H14 0.34750 0.69870 0.56210 0.0460 Uiso calc R 1.000 H H15 0.43890 0.48090 0.51490 0.0550 Uiso calc R 1.000 H H16 0.36680 0.25340 0.55360 0.0570 Uiso calc R 1.000 H H17 0.20230 0.22860 0.63770 0.0480 Uiso calc R 1.000 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' Cl Cl 0.1484 0.1585 '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' C C 0.0033 0.0016 '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 O1 Cl1 O2 109.43(18) no O1 Cl1 O3 109.87(18) no O1 Cl1 O4 110.09(19) no O2 Cl1 O3 109.35(18) no O2 Cl1 O4 109.5(2) no O3 Cl1 O4 108.6(2) no O11 Cl2 O12 109.04(18) no O11 Cl2 O13 109.06(18) no O11 Cl2 O14 110.05(19) no O12 Cl2 O13 108.6(2) no O12 Cl2 O14 110.4(2) no O13 Cl2 O14 109.7(2) no C2 N1 C8 109.9(3) no C2 N3 C9 109.6(3) no C2 N3 H3 125 no C2 N1 H1 125 no C8 N1 H1 125 no C9 N3 H3 125 no C12 N11 C18 109.5(3) no C12 N13 C19 108.4(3) no C12 N11 H11 125 no C18 N11 H11 125 no C12 N13 H13 126 no C19 N13 H13 126 no N1 C2 N3 109.7(3) no C5 C4 C9 115.7(4) no C4 C5 C6 122.8(4) no C5 C6 C7 121.9(4) no C6 C7 C8 116.2(3) no N1 C8 C7 132.8(3) no C7 C8 C9 121.3(3) no N1 C8 C9 105.9(3) no C4 C9 C8 122.2(3) no N3 C9 C4 132.9(3) no N3 C9 C8 105.0(3) no N1 C2 H2 125 no N3 C2 H2 125 no C5 C4 H4 122 no C9 C4 H4 122 no C6 C5 H5 119 no C4 C5 H5 119 no C5 C6 H6 119 no C7 C6 H6 119 no C8 C7 H7 122 no C6 C7 H7 122 no N11 C12 N13 109.5(3) no C15 C14 C19 115.6(3) no C14 C15 C16 120.7(4) no C15 C16 C17 123.2(4) no C16 C17 C18 115.7(4) no N11 C18 C17 131.6(3) no C17 C18 C19 122.8(3) no N11 C18 C19 105.6(3) no N13 C19 C18 107.0(3) no N13 C19 C14 131.0(3) no C14 C19 C18 122.0(3) no N11 C12 H12 125 no N13 C12 H12 125 no C15 C14 H14 122 no C19 C14 H14 122 no C14 C15 H15 120 no C16 C15 H15 120 no C15 C16 H16 118 no C17 C16 H16 118 no C18 C17 H17 122 no C16 C17 H17 122 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl1 O1 1.431(3) no Cl1 O2 1.424(3) no Cl1 O3 1.434(3) no Cl1 O4 1.429(4) no Cl2 O11 1.440(3) no Cl2 O12 1.428(3) no Cl2 O13 1.425(3) no Cl2 O14 1.408(4) no N1 C2 1.300(5) no N1 C8 1.388(5) no N3 C2 1.328(4) no N3 C9 1.388(4) no N1 H1 0.86 no N3 H3 0.86 no N11 C12 1.307(5) no N11 C18 1.396(5) no N13 C19 1.388(4) no N13 C12 1.327(4) no N11 H11 0.86 no N13 H13 0.86 no C4 C5 1.367(6) no C4 C9 1.383(5) no C5 C6 1.410(6) no C6 C7 1.367(5) no C7 C8 1.396(5) no C8 C9 1.410(5) no C2 H2 0.93 no C4 H4 0.93 no C5 H5 0.93 no C6 H6 0.93 no C7 H7 0.93 no C14 C19 1.400(5) no C14 C15 1.395(6) no C15 C16 1.399(6) no C16 C17 1.366(5) no C17 C18 1.378(5) no C18 C19 1.372(5) no C12 H12 0.93 no C14 H14 0.93 no C15 H15 0.93 no C16 H16 0.93 no C17 H17 0.93 no 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 _geom_hbond_publ_flag N1 H1 O1 . 0.86 2.38 3.007(5) 130 yes N1 H1 O12 1_565 0.86 2.26 3.022(4) 148 yes N3 H3 O13 . 0.86 2.05 2.863(4) 157 yes N11 H11 O11 4_465 0.86 2.38 3.011(5) 130 yes N11 H11 O2 4_465 0.86 2.23 3.011(4) 151 yes N13 H13 O3 4_475 0.86 2.06 2.866(4) 155 yes C2 H2 O2 . 0.93 2.47 3.349(4) 159 yes C2 H2 O11 . 0.93 2.59 3.279(4) 131 yes C7 H7 O13 1_565 0.93 2.51 3.413(5) 164 yes C12 H12 O12 4_465 0.93 2.49 3.370(5) 158 yes C17 H17 O3 4_465 0.93 2.48 3.393(5) 166 yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 15204364 2 PubChem 139072621