#------------------------------------------------------------------------------ #$Date: 2020-04-23 13:24:41 +0300 (Thu, 23 Apr 2020) $ #$Revision: 251074 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/78/1557878.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1557878 loop_ _publ_author_name 'Anulewicz, Romana' 'Bak, Tomasz' 'Cyranski, Michal' 'Krygowski, Tadeusz Marek' 'Pawlak, Dorota' 'Pniewska, Barbara' 'Rasala, Danuta' 'Gawinecki, Ryszard' _publ_section_title ; Substituent Effects on the Geometry of the Pyridine Ring in 1-Methyl-4-(4-R-phenyl)-2,6-diphenylpyridinium Perchlorates ; _journal_name_full 'Acta Chemica Scandinavica' _journal_page_first 515 _journal_page_last 523 _journal_paper_doi 10.3891/acta.chem.scand.49-0515 _journal_volume 49 _journal_year 1995 _chemical_formula_sum 'C24 H19 Cl2 N O4' _chemical_formula_weight 456.30 _chemical_name_common ; 1-methy1-4-(4-chloropheny1)-2,6-diphenylpyridinium perchlorate ; _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _cell_angle_alpha 90. _cell_angle_beta 103.35(3) _cell_angle_gamma 90. _cell_formula_units_Z 4 _cell_length_a 13.120(4) _cell_length_b 11.853(2) _cell_length_c 14.182(5) _cell_volume 2145.9(11) _diffrn_ambient_temperature 293 _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.5418 _exptl_absorpt_coefficient_mu 2.990 _exptl_crystal_density_diffrn 1.412 _exptl_crystal_F_000 944 _refine_ls_number_parameters 299 _refine_ls_number_reflns 3237 _refine_ls_R_factor_all 0.0938 _refine_ls_R_factor_gt 0.0832 _refine_ls_wR_factor_gt 0.2177 _refine_ls_wR_factor_ref 0.2576 _cod_data_source_file Acta-Chem-Scand-1995-49-515-523-2.cif _cod_data_source_block 1 _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 1557878 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 x,y,z 2 1/2-x,1/2+y,1/2-z 3 -x,-y,-z 4 1/2+x,1/2-y,1/2+z loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl2 Cl Uiso -0.77550(10) -0.07820(10) 0.56340(10) 1.000 0.0610(10) . . . . Cl1 Cl Uiso 0.00650(10) 0.12640(10) 0.22510(10) 1.000 0.0540(10) . . . . N1 N Uiso -0.3377(2) 0.3589(2) 0.3515(2) 1.000 0.0360(10) . . . . C1 C Uiso -0.2668(3) 0.4351(3) 0.3136(3) 1.000 0.0480(10) . . . . O1 O Uiso 0.0973(2) 0.1906(3) 0.2242(2) 1.000 0.0670(10) . . . . C2 C Uiso -0.3406(3) 0.3611(2) 0.4465(2) 1.000 0.0360(10) . . . . O2 O Uiso -0.0498(2) 0.1027(3) 0.1285(2) 1.000 0.0670(10) . . . . O3 O Uiso 0.0377(5) 0.0251(5) 0.2733(4) 1.000 0.163(3) . . . . C3 C Uiso -0.4154(3) 0.2988(3) 0.4779(2) 1.000 0.0390(10) . . . . C4 C Uiso -0.4871(2) 0.2314(2) 0.4155(2) 1.000 0.0350(10) . . . . O4 O Uiso -0.0571(3) 0.1888(7) 0.2735(3) 1.000 0.161(3) . . . . C5 C Uiso -0.4801(2) 0.2308(3) 0.3189(2) 1.000 0.0380(10) . . . . C6 C Uiso -0.4059(2) 0.2920(2) 0.2873(2) 1.000 0.0350(10) . . . . C21 C Uiso -0.2622(3) 0.4270(3) 0.5177(2) 1.000 0.0420(10) . . . . C22 C Uiso -0.1550(3) 0.4083(3) 0.5294(3) 1.000 0.0550(10) . . . . C23 C Uiso -0.0841(4) 0.4667(4) 0.6005(3) 1.000 0.0670(10) . . . . C24 C Uiso -0.1194(4) 0.5429(4) 0.6603(4) 1.000 0.0720(10) . . . . C25 C Uiso -0.2235(4) 0.5591(3) 0.6495(3) 1.000 0.0660(10) . . . . C26 C Uiso -0.2967(3) 0.5017(3) 0.5796(2) 1.000 0.0480(10) . . . . C41 C Uiso -0.5609(2) 0.1581(3) 0.4513(2) 1.000 0.0360(10) . . . . C42 C Uiso -0.6515(3) 0.1154(3) 0.3894(2) 1.000 0.0450(10) . . . . C43 C Uiso -0.7173(3) 0.0432(3) 0.4223(2) 1.000 0.0470(10) . . . . C44 C Uiso -0.6930(3) 0.0125(3) 0.5191(3) 1.000 0.0430(10) . . . . C45 C Uiso -0.6054(3) 0.0541(3) 0.5828(2) 1.000 0.0420(10) . . . . C46 C Uiso -0.5399(3) 0.1266(3) 0.5485(2) 1.000 0.0400(10) . . . . C61 C Uiso -0.3956(2) 0.2849(2) 0.1858(2) 1.000 0.0350(10) . . . . C62 C Uiso -0.4742(3) 0.3254(3) 0.1107(2) 1.000 0.0450(10) . . . . C63 C Uiso -0.4638(3) 0.3179(3) 0.0157(2) 1.000 0.0480(10) . . . . C64 C Uiso -0.3761(3) 0.2685(3) -0.0043(2) 1.000 0.0450(10) . . . . C65 C Uiso -0.2981(3) 0.2270(3) 0.0699(2) 1.000 0.0450(10) . . . . C66 C Uiso -0.3064(3) 0.2357(3) 0.1650(2) 1.000 0.0430(10) . . . . loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 ' 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_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Cl1 O4 110.7(4) . . . yes O1 Cl1 O4 108.5(3) . . . yes O1 Cl1 O2 110.33(19) . . . yes O1 Cl1 O3 108.3(3) . . . yes O2 Cl1 O3 109.2(3) . . . yes O2 Cl1 O4 109.8(2) . . . yes C1 N1 C6 118.6(3) . . . yes C1 N1 C2 120.8(3) . . . yes C2 N1 C6 120.4(3) . . . yes N1 C2 C21 120.7(3) . . . yes N1 C2 C3 119.7(3) . . . yes C3 C2 C21 119.6(3) . . . no C2 C3 C4 122.0(3) . . . no C3 C4 C41 121.5(3) . . . no C3 C4 C5 116.2(3) . . . no C5 C4 C41 122.2(3) . . . no C4 C5 C6 122.1(3) . . . no N1 C6 C5 119.5(3) . . . yes C5 C6 C61 121.3(2) . . . no N1 C6 C61 119.1(2) . . . yes C22 C21 C26 119.4(3) . . . no C2 C21 C22 121.2(3) . . . no C2 C21 C26 119.2(3) . . . no C21 C22 C23 119.7(4) . . . no C22 C23 C24 120.4(5) . . . no C23 C24 C25 119.6(5) . . . no C24 C25 C26 121.7(4) . . . no C21 C26 C25 119.3(4) . . . no C42 C41 C46 118.0(3) . . . no C4 C41 C42 121.8(3) . . . no C4 C41 C46 120.2(3) . . . no C41 C42 C43 121.5(3) . . . no C42 C43 C44 118.8(3) . . . no Cl2 C44 C43 120.0(3) . . . yes C43 C44 C45 121.5(3) . . . no Cl2 C44 C45 118.5(3) . . . yes C44 C45 C46 119.0(3) . . . no C41 C46 C45 121.2(3) . . . no C6 C61 C62 120.6(3) . . . no C6 C61 C66 119.9(2) . . . no C62 C61 C66 119.5(3) . . . no C61 C62 C63 120.1(3) . . . no C62 C63 C64 120.1(3) . . . no C63 C64 C65 120.2(3) . . . no C64 C65 C66 120.4(4) . . . no C61 C66 C65 119.7(3) . . . no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl2 C44 1.742(4) . . yes Cl1 O4 1.407(6) . . yes Cl1 O3 1.396(6) . . yes Cl1 O1 1.416(3) . . yes Cl1 O2 1.426(3) . . yes N1 C6 1.372(4) . . yes N1 C2 1.357(4) . . yes N1 C1 1.484(5) . . yes C2 C21 1.486(5) . . no C2 C3 1.382(5) . . no C3 C4 1.386(4) . . no C4 C5 1.394(4) . . no C4 C41 1.476(4) . . no C5 C6 1.370(4) . . no C6 C61 1.479(4) . . no C21 C26 1.394(5) . . no C21 C22 1.395(6) . . no C22 C23 1.389(6) . . no C23 C24 1.390(7) . . no C24 C25 1.352(8) . . no C25 C26 1.389(6) . . no C41 C46 1.393(4) . . no C41 C42 1.399(5) . . no C42 C43 1.372(5) . . no C43 C44 1.384(5) . . no C44 C45 1.379(5) . . no C45 C46 1.381(5) . . no C61 C62 1.386(4) . . no C61 C66 1.399(5) . . no C62 C63 1.388(4) . . no C63 C64 1.378(5) . . no C64 C65 1.378(5) . . no C65 C66 1.382(4) . . no 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 C1 N1 C2 C3 172.7(3) . . . . no C1 N1 C2 C21 -9.2(4) . . . . no C6 N1 C2 C3 -2.5(4) . . . . no C6 N1 C2 C21 175.7(3) . . . . no C1 N1 C6 C5 -172.6(3) . . . . no C1 N1 C6 C61 9.3(4) . . . . no C2 N1 C6 C5 2.7(4) . . . . no C2 N1 C6 C61 -175.5(3) . . . . no N1 C2 C3 C4 1.4(5) . . . . no C21 C2 C3 C4 -176.7(3) . . . . no N1 C2 C21 C22 -56.3(4) . . . . no N1 C2 C21 C26 129.4(3) . . . . no C3 C2 C21 C22 121.9(4) . . . . no C3 C2 C21 C26 -52.5(4) . . . . no C2 C3 C4 C5 -0.6(5) . . . . no C2 C3 C4 C41 174.9(3) . . . . no C3 C4 C5 C6 0.8(4) . . . . no C41 C4 C5 C6 -174.6(3) . . . . no C3 C4 C41 C42 161.3(3) . . . . no C3 C4 C41 C46 -20.7(5) . . . . no C5 C4 C41 C42 -23.5(5) . . . . no C5 C4 C41 C46 154.5(3) . . . . no C4 C5 C6 N1 -1.9(4) . . . . no C4 C5 C6 C61 176.2(3) . . . . no N1 C6 C61 C62 -115.0(3) . . . . no N1 C6 C61 C66 65.8(3) . . . . no C5 C6 C61 C62 66.9(4) . . . . no C5 C6 C61 C66 -112.4(3) . . . . no C2 C21 C22 C23 -176.3(3) . . . . no C26 C21 C22 C23 -1.9(5) . . . . no C2 C21 C26 C25 176.7(3) . . . . no C22 C21 C26 C25 2.3(5) . . . . no C21 C22 C23 C24 0.4(6) . . . . no C22 C23 C24 C25 0.7(7) . . . . no C23 C24 C25 C26 -0.3(7) . . . . no C24 C25 C26 C21 -1.2(6) . . . . no C4 C41 C42 C43 177.0(3) . . . . no C46 C41 C42 C43 -1.1(5) . . . . no C4 C41 C46 C45 -177.1(3) . . . . no C42 C41 C46 C45 1.0(5) . . . . no C41 C42 C43 C44 0.1(6) . . . . no C42 C43 C44 Cl2 179.5(3) . . . . no C42 C43 C44 C45 0.9(6) . . . . no Cl2 C44 C45 C46 -179.6(3) . . . . no C43 C44 C45 C46 -1.0(6) . . . . no C44 C45 C46 C41 0.0(6) . . . . no C6 C61 C62 C63 -179.8(3) . . . . no C66 C61 C62 C63 -0.5(5) . . . . no C6 C61 C66 C65 178.6(3) . . . . no C62 C61 C66 C65 -0.7(5) . . . . no C61 C62 C63 C64 1.1(5) . . . . no C62 C63 C64 C65 -0.4(6) . . . . no C63 C64 C65 C66 -0.8(6) . . . . no C64 C65 C66 C61 1.3(5) . . . . no