#------------------------------------------------------------------------------ #$Date: 2015-01-23 12:30:19 +0000 (Fri, 23 Jan 2015) $ #$Revision: 130086 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/22/2202245.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_2202245 loop_ _publ_author_name 'Baumer, Vyacheslav N.' 'Karasev, Alexander A.' 'Sizova, Zoya A.' _publ_section_title ; 2-Amino-7-methoxy-3-(1-methyl-1H-benzimidazol-2-yl)chromenium perchlorate ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o54 _journal_page_last o56 _journal_paper_doi 10.1107/S1600536802022699 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C18 H16 N3 O2 1+, Cl O4 1-' _chemical_formula_moiety 'C18 H16 N3 O2 1+, Cl O4 1-' _chemical_formula_sum 'C18 H16 Cl N3 O6' _chemical_formula_weight 405.79 _chemical_name_systematic ; 2-Amino-7-methoxy-3-(1-methyl-1H-benzimidazol-2-yl)chromenium perchlorate ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 94.71(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.6272(17) _cell_length_b 10.979(3) _cell_length_c 18.788(7) _cell_measurement_reflns_used 24 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 12.0 _cell_measurement_theta_min 11.0 _cell_volume 1773.6(9) _computing_cell_refinement P3 _computing_data_collection 'P3 (Siemens, 1989)' _computing_data_reduction 'XDISK and XPREP (Siemens, 1991)' _computing_molecular_graphics 'XP (Siemens, 1991)' _computing_publication_material 'WinGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Siemens P3/PC' _diffrn_measurement_method 2\q/\q _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 0.043 _diffrn_reflns_av_sigmaI/netI 0.069 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 3526 _diffrn_reflns_theta_full 25.5 _diffrn_reflns_theta_max 25.5 _diffrn_reflns_theta_min 2.5 _diffrn_standards_decay_% 1 _diffrn_standards_interval_count 98 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 0.26 _exptl_absorpt_correction_type none _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.520 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'complex polyhedron' _exptl_crystal_F_000 840 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.23 _refine_diff_density_min -0.28 _refine_ls_extinction_coef 0.0017(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.0017xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.01 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 256 _refine_ls_number_reflns 3297 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.01 _refine_ls_R_factor_all 0.070 _refine_ls_R_factor_gt 0.047 _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^)+(0.03P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.095 _refine_ls_wR_factor_ref 0.099 _reflns_number_gt 1992 _reflns_number_total 3297 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ya6118.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_cell_volume 1773.5(9) _cod_database_code 2202245 _cod_database_fobs_code 2202245 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' 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 O1 0.2177(2) 0.09447(18) 0.53233(9) 0.0370(5) Uani d . 1 . . O O2 0.4061(3) -0.2083(2) 0.38248(11) 0.0481(6) Uani d . 1 . . O N1 0.1405(3) 0.2207(2) 0.61471(12) 0.0435(7) Uani d . 1 . . N H1A 0.2088 0.1854 0.6436 0.052 Uiso calc R 1 . . H H1B 0.0845 0.2786 0.6297 0.052 Uiso calc R 1 . . H N2 -0.1836(3) 0.4127(2) 0.46649(12) 0.0338(6) Uani d . 1 . . N N3 -0.0873(3) 0.3797(2) 0.58101(12) 0.0373(6) Uani d . 1 . . N C2 0.1217(3) 0.1862(3) 0.54781(15) 0.0334(7) Uani d . 1 . . C C3 0.0097(3) 0.2379(3) 0.49303(14) 0.0296(6) Uani d . 1 . . C C4 0.0008(3) 0.1797(3) 0.42742(15) 0.0354(7) Uani d . 1 . . C H4 -0.0728 0.2066 0.3920 0.042 Uiso calc R 1 . . H C5 0.0930(3) 0.0197(3) 0.34432(15) 0.0402(7) Uani d . 1 . . C H5 0.0212 0.0445 0.3075 0.048 Uiso calc R 1 . . H C6 0.1930(3) -0.0758(3) 0.33348(15) 0.0408(7) Uani d . 1 . . C H6 0.1873 -0.1150 0.2895 0.049 Uiso calc R 1 . . H C7 0.3041(3) -0.1147(3) 0.38878(16) 0.0365(7) Uani d . 1 . . C C8 0.3112(3) -0.0554(3) 0.45627(15) 0.0373(7) Uani d . 1 . . C H8 0.3827 -0.0796 0.4933 0.045 Uiso calc R 1 . . H C9 0.0993(3) 0.0806(3) 0.41163(14) 0.0314(6) Uani d . 1 . . C C10 0.2093(3) 0.0390(3) 0.46522(14) 0.0323(7) Uani d . 1 . . C C11 -0.0868(3) 0.3423(3) 0.51298(15) 0.0320(6) Uani d . 1 . . C C12 -0.2499(3) 0.5016(3) 0.50854(15) 0.0316(6) Uani d . 1 . . C C13 -0.3558(3) 0.5969(3) 0.49194(17) 0.0412(7) Uani d . 1 . . C H13 -0.3968 0.6109 0.4453 0.049 Uiso calc R 1 . . H C14 -0.3963(4) 0.6687(3) 0.54801(17) 0.0448(8) Uani d . 1 . . C H14 -0.4661 0.7324 0.5386 0.054 Uiso calc R 1 . . H C15 -0.3347(4) 0.6483(3) 0.61938(18) 0.0482(9) Uani d . 1 . . C H15 -0.3650 0.6986 0.6555 0.058 Uiso calc R 1 . . H C16 -0.2299(4) 0.5545(3) 0.63627(17) 0.0469(8) Uani d . 1 . . C H16 -0.1880 0.5419 0.6829 0.056 Uiso calc R 1 . . H C17 -0.1893(3) 0.4788(3) 0.57931(15) 0.0344(7) Uani d . 1 . . C C18 -0.2094(4) 0.4112(3) 0.38722(15) 0.0446(8) Uani d . 1 . . C H18A -0.1111 0.4051 0.3670 0.067 Uiso calc R 1 . . H H18B -0.2606 0.4850 0.3711 0.067 Uiso calc R 1 . . H H18C -0.2730 0.3426 0.3724 0.067 Uiso calc R 1 . . H C19 0.4059(4) -0.2701(3) 0.31384(16) 0.0519(9) Uani d . 1 . . C H19A 0.3054 -0.3054 0.3017 0.078 Uiso calc R 1 . . H H19B 0.4833 -0.3331 0.3169 0.078 Uiso calc R 1 . . H H19C 0.4288 -0.2125 0.2777 0.078 Uiso calc R 1 . . H Cl 0.36755(9) -0.08682(7) 0.70706(4) 0.0405(2) Uani d . 1 . . Cl O3 0.3694(3) -0.1181(2) 0.63269(11) 0.0646(7) Uani d . 1 . . O O4 0.5102(3) -0.1211(3) 0.74588(14) 0.0854(10) Uani d . 1 . . O O5 0.3416(4) 0.0426(2) 0.71428(14) 0.0817(9) Uani d . 1 . . O O6 0.2427(3) -0.1529(3) 0.73705(14) 0.0749(8) Uani d . 1 . . O 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 O1 0.0438(12) 0.0351(11) 0.0308(10) 0.0063(10) -0.0043(9) -0.0023(9) O2 0.0522(15) 0.0495(14) 0.0424(13) 0.0171(11) 0.0032(11) -0.0046(11) N1 0.0512(17) 0.0482(17) 0.0299(14) 0.0090(14) -0.0034(12) -0.0010(12) N2 0.0320(13) 0.0369(14) 0.0325(13) -0.0012(12) 0.0022(10) 0.0018(12) N3 0.0400(15) 0.0419(15) 0.0303(13) 0.0055(12) 0.0045(11) -0.0015(11) C2 0.0353(17) 0.0302(16) 0.0352(16) -0.0068(13) 0.0067(13) 0.0011(13) C3 0.0301(15) 0.0306(15) 0.0282(14) -0.0034(13) 0.0032(12) 0.0041(12) C4 0.0328(16) 0.0379(17) 0.0343(16) 0.0009(14) -0.0042(13) -0.0007(13) C5 0.0367(18) 0.0435(18) 0.0396(17) 0.0054(15) -0.0026(14) -0.0007(15) C6 0.0419(18) 0.0460(18) 0.0342(16) -0.0009(16) 0.0019(13) 0.0005(15) C7 0.0361(17) 0.0349(18) 0.0394(17) 0.0025(13) 0.0081(13) 0.0020(13) C8 0.0387(18) 0.0338(17) 0.0384(17) 0.0005(13) -0.0034(13) 0.0040(13) C9 0.0301(15) 0.0314(15) 0.0326(15) -0.0003(13) 0.0014(12) -0.0019(13) C10 0.0348(16) 0.0327(16) 0.0293(15) -0.0010(13) 0.0015(12) -0.0001(12) C11 0.0309(16) 0.0287(15) 0.0362(16) -0.0035(12) 0.0025(13) 0.0003(13) C12 0.0252(15) 0.0299(15) 0.0396(16) -0.0041(12) 0.0022(12) 0.0031(13) C13 0.0346(17) 0.0391(18) 0.0496(19) 0.0001(15) 0.0019(14) 0.0038(16) C14 0.0392(19) 0.0349(17) 0.061(2) 0.0076(15) 0.0099(16) 0.0079(16) C15 0.045(2) 0.046(2) 0.054(2) 0.0045(17) 0.0123(16) -0.0004(17) C16 0.056(2) 0.048(2) 0.0375(18) 0.0085(16) 0.0083(15) 0.0017(15) C17 0.0304(16) 0.0370(16) 0.0372(16) 0.0018(14) 0.0105(12) 0.0012(14) C18 0.054(2) 0.0404(18) 0.0377(17) 0.0065(17) -0.0039(14) 0.0006(15) C19 0.057(2) 0.053(2) 0.046(2) 0.0138(18) 0.0104(17) -0.0112(17) Cl 0.0435(4) 0.0432(4) 0.0335(4) -0.0015(4) -0.0042(3) 0.0010(4) O3 0.092(2) 0.0649(18) 0.0374(13) -0.0005(15) 0.0059(12) -0.0063(12) O4 0.0526(16) 0.115(3) 0.083(2) 0.0114(17) -0.0301(14) -0.0025(18) O5 0.136(3) 0.0403(15) 0.0669(18) 0.0129(16) -0.0035(17) -0.0051(13) O6 0.0661(17) 0.089(2) 0.0726(19) -0.0169(16) 0.0220(14) 0.0212(16) 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' Cl Cl 0.1484 0.1585 '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 C2 O1 C10 122.2(2) yes C7 O2 C19 118.3(2) yes C2 N1 H1A 120.0 no C2 N1 H1B 120.0 no H1A N1 H1B 120.0 no C11 N2 C12 106.5(2) yes C11 N2 C18 130.9(2) yes C12 N2 C18 122.4(2) yes C11 N3 C17 105.5(2) yes N1 C2 O1 113.1(3) yes N1 C2 C3 125.7(3) yes O1 C2 C3 121.2(2) yes C4 C3 C2 115.5(3) yes C4 C3 C11 126.2(3) yes C2 C3 C11 118.2(2) yes C3 C4 C9 123.1(3) yes C3 C4 H4 118.4 no C9 C4 H4 118.4 no C6 C5 C9 120.4(3) yes C6 C5 H5 119.8 no C9 C5 H5 119.8 no C5 C6 C7 120.8(3) yes C5 C6 H6 119.6 no C7 C6 H6 119.6 no O2 C7 C8 116.2(3) yes O2 C7 C6 124.4(3) yes C6 C7 C8 119.4(3) yes C10 C8 C7 118.1(3) yes C10 C8 H8 120.9 no C7 C8 H8 120.9 no C10 C9 C4 118.6(2) yes C10 C9 C5 117.2(3) yes C4 C9 C5 124.2(3) yes C8 C10 O1 116.9(2) yes C8 C10 C9 124.0(3) yes O1 C10 C9 119.2(2) yes N3 C11 N2 112.3(3) yes N3 C11 C3 121.5(2) yes N2 C11 C3 126.2(3) yes N2 C12 C17 105.7(2) yes N2 C12 C13 132.7(3) yes C13 C12 C17 121.6(3) yes C14 C13 C12 117.1(3) yes C14 C13 H13 121.5 no C12 C13 H13 121.5 no C13 C14 C15 122.1(3) yes C13 C14 H14 119.0 no C15 C14 H14 119.0 no C16 C15 C14 121.3(3) yes C16 C15 H15 119.4 no C14 C15 H15 119.4 no C15 C16 C17 117.2(3) yes C15 C16 H16 121.4 no C17 C16 H16 121.4 no N3 C17 C12 110.1(3) yes N3 C17 C16 129.1(3) yes C12 C17 C16 120.7(3) yes N2 C18 H18A 109.5 no N2 C18 H18B 109.5 no H18A C18 H18B 109.5 no N2 C18 H18C 109.5 no H18A C18 H18C 109.5 no H18B C18 H18C 109.5 no O2 C19 H19A 109.5 no O2 C19 H19B 109.5 no H19A C19 H19B 109.5 no O2 C19 H19C 109.5 no H19A C19 H19C 109.5 no H19B C19 H19C 109.5 no O4 Cl O3 110.78(17) yes O4 Cl O5 110.15(19) yes O3 Cl O5 109.83(15) yes O4 Cl O6 107.82(18) yes O3 Cl O6 108.98(16) yes O5 Cl O6 109.2(2) yes 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 O1 C2 . 1.351(3) yes O1 C10 . 1.397(3) yes O2 C7 . 1.364(3) yes O2 C19 . 1.457(3) yes N1 C2 . 1.310(3) yes N1 H1A . 0.8600 no N1 H1B . 0.8600 no N2 C11 . 1.392(3) yes N2 C12 . 1.406(3) yes N2 C18 . 1.488(3) yes N3 C11 . 1.343(3) yes N3 C17 . 1.399(4) yes C2 C3 . 1.467(4) yes C3 C4 . 1.385(4) yes C3 C11 . 1.483(4) yes C4 C9 . 1.426(4) yes C4 H4 . 0.9300 no C5 C6 . 1.384(4) yes C5 C9 . 1.427(4) yes C5 H5 . 0.9300 no C6 C7 . 1.420(4) yes C6 H6 . 0.9300 no C7 C8 . 1.422(4) yes C8 C10 . 1.378(4) yes C8 H8 . 0.9300 no C9 C10 . 1.403(4) yes C12 C17 . 1.410(4) yes C12 C13 . 1.407(4) yes C13 C14 . 1.384(4) yes C13 H13 . 0.9300 no C14 C15 . 1.419(4) yes C14 H14 . 0.9300 no C15 C16 . 1.389(4) yes C15 H15 . 0.9300 no C16 C17 . 1.421(4) yes C16 H16 . 0.9300 no C18 H18A . 0.9600 no C18 H18B . 0.9600 no C18 H18C . 0.9600 no C19 H19A . 0.9600 no C19 H19B . 0.9600 no C19 H19C . 0.9600 no Cl O4 . 1.428(2) yes Cl O3 . 1.440(2) yes Cl O5 . 1.446(2) yes Cl O6 . 1.450(3) yes loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H1A O5 0.86 2.30 3.130(4) 163 yes N1 H1B N3 0.86 2.01 2.665(4) 132 yes 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 C10 O1 C2 N1 175.7(2) yes C10 O1 C2 C3 -4.1(4) yes N1 C2 C3 C4 -174.5(3) no O1 C2 C3 C4 5.3(4) yes N1 C2 C3 C11 3.1(4) yes O1 C2 C3 C11 -177.1(2) no C2 C3 C4 C9 -3.6(4) yes C11 C3 C4 C9 179.0(3) yes C9 C5 C6 C7 -0.3(5) no C19 O2 C7 C8 -178.5(3) yes C19 O2 C7 C6 2.4(4) no C5 C6 C7 O2 179.7(3) no C5 C6 C7 C8 0.7(4) no O2 C7 C8 C10 -179.4(3) no C6 C7 C8 C10 -0.3(4) no C3 C4 C9 C10 0.7(4) no C3 C4 C9 C5 -179.6(3) no C6 C5 C9 C10 -0.3(4) no C6 C5 C9 C4 180.0(3) no C7 C8 C10 O1 179.2(3) no C7 C8 C10 C9 -0.3(4) no C2 O1 C10 C8 -178.6(3) no C2 O1 C10 C9 0.9(4) no C4 C9 C10 C8 -179.6(3) no C5 C9 C10 C8 0.7(4) no C4 C9 C10 O1 0.8(4) no C5 C9 C10 O1 -178.9(3) no C17 N3 C11 N2 0.2(3) yes C17 N3 C11 C3 179.7(2) yes C12 N2 C11 N3 0.2(3) yes C18 N2 C11 N3 174.5(3) yes C12 N2 C11 C3 -179.3(3) yes C18 N2 C11 C3 -5.0(5) yes C4 C3 C11 N3 169.0(3) yes C2 C3 C11 N3 -8.3(4) yes C4 C3 C11 N2 -11.6(5) yes C2 C3 C11 N2 171.1(3) yes C11 N2 C12 C17 -0.5(3) yes C18 N2 C12 C17 -175.4(2) yes C11 N2 C12 C13 -179.8(3) yes C18 N2 C12 C13 5.4(5) yes N2 C12 C13 C14 -179.8(3) no C17 C12 C13 C14 1.0(4) no C12 C13 C14 C15 0.0(5) no C13 C14 C15 C16 0.1(5) no C14 C15 C16 C17 -1.1(5) no C11 N3 C17 C12 -0.5(3) no C11 N3 C17 C16 -178.2(3) no N2 C12 C17 N3 0.6(3) no C13 C12 C17 N3 180.0(3) no N2 C12 C17 C16 178.5(3) no C13 C12 C17 C16 -2.1(4) no C15 C16 C17 N3 179.5(3) no C15 C16 C17 C12 2.1(5) no