#------------------------------------------------------------------------------ #$Date: 2020-04-23 13:25:17 +0300 (Thu, 23 Apr 2020) $ #$Revision: 251077 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/78/1557881.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_1557881 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 'C26 H25 Cl N2 O4' _chemical_formula_weight 464.95 _chemical_name_common ; 1-methy1-4-(4-dimethylpheny1)-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 97.52(4) _cell_angle_gamma 90. _cell_formula_units_Z 4 _cell_length_a 7.979(4) _cell_length_b 17.892(8) _cell_length_c 16.954(8) _cell_volume 2400(2) _diffrn_ambient_temperature 293 _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.5418 _exptl_absorpt_coefficient_mu 1.693 _exptl_crystal_density_diffrn 1.287 _exptl_crystal_F_000 976 _refine_ls_number_parameters 341 _refine_ls_number_reflns 3749 _refine_ls_R_factor_all 0.1178 _refine_ls_R_factor_gt 0.0753 _refine_ls_wR_factor_gt 0.2069 _refine_ls_wR_factor_ref 0.2655 _cod_data_source_file Acta-Chem-Scand-1995-49-515-523-5.cif _cod_data_source_block 1 _cod_original_cell_volume 2400(12) _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 1557881 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 Cl1 Cl Uiso 0.56780(10) 0.22330(10) 0.73210(10) 1.000 0.0930(10) . . . . N1 N Uiso 0.0633(3) 0.2165(2) 0.7381(2) 1.000 0.0440(10) . . . . N2 N Uiso 0.2809(6) 0.5516(2) 1.0893(2) 1.000 0.0810(10) . . . . C1 C Uiso 0.0158(6) 0.1596(2) 0.6762(2) 1.000 0.0650(10) . . . . O1 O Uiso 0.7058(8) 0.2295(6) 0.7883(5) 1.000 0.214(4) . . . . O2 O Uiso 0.6132(11) 0.2406(5) 0.6605(4) 1.000 0.206(3) . . . . C2 C Uiso 0.0870(4) 0.1963(2) 0.8166(2) 1.000 0.0450(10) . . . . C3 C Uiso 0.1189(5) 0.2496(2) 0.8740(2) 1.000 0.0500(10) . . . . O3 O Uiso 0.4723(17) 0.2925(7) 0.7450(9) 0.500 0.157(6) . . . . C4 C Uiso 0.1281(5) 0.3285(2) 0.8560(2) 1.000 0.0490(10) . . . . O4 O Uiso 0.598(3) 0.1399(9) 0.7456(9) 0.500 0.206(7) . . . . O5 O Uiso 0.4479(12) 0.1718(6) 0.6976(8) 0.500 0.139(4) . . . . C5 C Uiso 0.1002(5) 0.3492(2) 0.7746(2) 1.000 0.0550(10) . . . . O6 O Uiso 0.4416(16) 0.2356(13) 0.7689(9) 0.500 0.205(8) . . . . C6 C Uiso 0.0705(4) 0.2900(2) 0.7173(2) 1.000 0.0470(10) . . . . C21 C Uiso 0.0765(5) 0.1157(2) 0.8372(2) 1.000 0.0550(10) . . . . C22 C Uiso -0.0581(7) 0.0912(3) 0.8731(3) 1.000 0.0780(10) . . . . C23 C Uiso -0.0736(11) 0.0172(3) 0.8958(4) 1.000 0.108(2) . . . . C24 C Uiso 0.0441(13) -0.0308(4) 0.8833(3) 1.000 0.120(3) . . . . C25 C Uiso 0.1857(11) -0.0098(3) 0.8500(4) 1.000 0.112(2) . . . . C26 C Uiso 0.2025(8) 0.0660(3) 0.8243(3) 1.000 0.086(2) . . . . C41 C Uiso 0.1671(5) 0.3832(2) 0.9168(2) 1.000 0.0540(10) . . . . C42 C Uiso 0.1481(5) 0.3716(2) 0.9961(2) 1.000 0.0550(10) . . . . C43 C Uiso 0.1841(5) 0.4261(2) 1.0527(2) 1.000 0.0590(10) . . . . C44 C Uiso 0.2433(6) 0.4964(2) 1.0335(2) 1.000 0.0640(10) . . . . C45 C Uiso 0.2635(8) 0.5082(3) 0.9544(3) 1.000 0.093(2) . . . . C46 C Uiso 0.2254(8) 0.4539(3) 0.8988(3) 1.000 0.084(2) . . . . C61 C Uiso 0.0491(5) 0.3114(2) 0.6321(2) 1.000 0.0540(10) . . . . C62 C Uiso -0.0829(6) 0.3551(3) 0.6017(2) 1.000 0.0740(10) . . . . C63 C Uiso -0.0982(8) 0.3787(3) 0.5226(3) 1.000 0.093(2) . . . . C64 C Uiso 0.0148(8) 0.3562(3) 0.4749(3) 1.000 0.092(2) . . . . C65 C Uiso 0.1474(8) 0.3117(3) 0.5045(3) 1.000 0.0810(10) . . . . C66 C Uiso 0.1656(6) 0.2895(3) 0.5830(2) 1.000 0.0690(10) . . . . C441 C Uiso 0.2640(10) 0.5380(3) 1.1725(3) 1.000 0.097(2) . . . . C442 C Uiso 0.3299(11) 0.6258(3) 1.0657(4) 1.000 0.109(2) . . . . 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 O1 Cl1 O5 142.3(7) . . . yes O1 Cl1 O6 105.2(7) . . . yes O2 Cl1 O3 98.3(7) . . . yes O2 Cl1 O4 107.7(8) . . . yes O2 Cl1 O5 91.4(6) . . . yes O2 Cl1 O6 136.6(9) . . . yes O3 Cl1 O4 150.3(10) . . . yes O3 Cl1 O5 105.9(7) . . . yes O3 Cl1 O6 47.8(12) . . . yes O4 Cl1 O5 60.3(9) . . . yes O4 Cl1 O6 102.5(13) . . . yes O5 Cl1 O6 77.1(10) . . . yes O1 Cl1 O2 108.9(5) . . . yes O1 Cl1 O3 102.3(7) . . . yes O1 Cl1 O4 83.0(9) . . . yes C1 N1 C2 120.0(3) . . . yes C1 N1 C6 119.8(3) . . . yes C2 N1 C6 120.1(3) . . . yes C44 N2 C441 120.5(4) . . . yes C44 N2 C442 120.6(4) . . . yes C441 N2 C442 118.8(4) . . . yes N1 C2 C3 119.9(3) . . . yes N1 C2 C21 118.6(3) . . . yes C3 C2 C21 121.4(3) . . . no C2 C3 C4 122.8(3) . . . no Cl1 O3 O6 56.2(10) . . . yes C3 C4 C5 117.0(3) . . . no C3 C4 C41 121.9(3) . . . no Cl1 O4 O5 55.7(8) . . . yes C5 C4 C41 121.1(3) . . . no Cl1 O5 O6 48.0(6) . . . yes O4 O5 O6 88.0(10) . . . yes Cl1 O5 O4 64.0(8) . . . yes C4 C5 C6 117.2(3) . . . no Cl1 O6 O3 76.0(12) . . . yes N1 C6 C5 123.0(3) . . . yes Cl1 O6 O5 54.9(8) . . . yes O3 O6 O5 109.1(13) . . . yes N1 C6 C61 119.8(3) . . . yes C5 C6 C61 117.2(3) . . . no C22 C21 C26 119.5(4) . . . no C2 C21 C22 119.0(4) . . . no C2 C21 C26 121.5(4) . . . no C21 C22 C23 122.0(6) . . . no C22 C23 C24 119.2(7) . . . no C23 C24 C25 122.0(7) . . . no C24 C25 C26 119.7(7) . . . no C21 C26 C25 117.5(6) . . . no C4 C41 C42 123.8(3) . . . no C4 C41 C46 120.8(3) . . . no C42 C41 C46 115.4(4) . . . no C41 C42 C43 122.1(3) . . . no C42 C43 C44 121.6(3) . . . no C43 C44 C45 116.6(4) . . . no N2 C44 C43 122.5(3) . . . yes N2 C44 C45 120.9(4) . . . yes C44 C45 C46 121.2(5) . . . no C41 C46 C45 123.1(5) . . . no C6 C61 C66 120.8(3) . . . no C62 C61 C66 118.9(3) . . . no C6 C61 C62 120.2(3) . . . no C61 C62 C63 120.3(4) . . . no C62 C63 C64 120.3(5) . . . no C63 C64 C65 120.0(5) . . . no C64 C65 C66 120.1(5) . . . no C61 C66 C65 120.4(5) . . . 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 Cl1 O1 1.363(8) . . yes Cl1 O2 1.348(7) . . yes Cl1 O3 1.485(13) . . yes Cl1 O4 1.524(16) . . yes Cl1 O5 1.400(11) . . yes Cl1 O6 1.271(14) . . yes N1 C1 1.476(5) . . yes N1 C2 1.368(5) . . yes N1 C6 1.365(5) . . yes N2 C442 1.455(7) . . yes N2 C441 1.455(6) . . yes N2 C44 1.373(5) . . yes C2 C3 1.363(5) . . no C2 C21 1.489(5) . . no C3 C4 1.448(5) . . no O3 O6 1.13(3) . . yes C4 C5 1.418(5) . . no C4 C41 1.426(5) . . no O4 O5 1.47(2) . . yes C5 C6 1.436(5) . . no O5 O6 1.67(2) . . yes C6 C61 1.483(5) . . no C21 C22 1.374(7) . . no C21 C26 1.381(7) . . no C22 C23 1.389(8) . . no C23 C24 1.310(12) . . no C24 C25 1.380(13) . . no C25 C26 1.436(8) . . no C41 C42 1.388(5) . . no C41 C46 1.395(7) . . no C42 C43 1.372(5) . . no C43 C44 1.397(5) . . no C44 C45 1.388(6) . . no C45 C46 1.360(7) . . no C61 C66 1.383(6) . . no C61 C62 1.358(6) . . no C62 C63 1.396(6) . . no C63 C64 1.349(8) . . no C64 C65 1.366(8) . . no C65 C66 1.378(6) . . 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 O2 Cl1 O4 O5 -81.2(9) . . . . no O3 Cl1 O4 O5 68.8(18) . . . . no O6 Cl1 O4 O5 67.1(10) . . . . no O1 Cl1 O5 O4 -14.4(13) . . . . no O1 Cl1 O5 O6 98.3(12) . . . . no O2 Cl1 O5 O4 109.7(9) . . . . no O2 Cl1 O5 O6 -137.7(10) . . . . no O3 Cl1 O5 O4 -151.3(10) . . . . no O3 Cl1 O5 O6 -38.6(11) . . . . no O4 Cl1 O5 O6 112.7(12) . . . . no O6 Cl1 O5 O4 -112.7(12) . . . . no O1 Cl1 O6 O3 92.9(11) . . . . no O1 Cl1 O6 O5 -141.1(7) . . . . no O2 Cl1 O6 O3 -47.8(17) . . . . no O2 Cl1 O6 O5 78.2(13) . . . . no O3 Cl1 O6 O5 126.0(12) . . . . no O4 Cl1 O6 O3 178.9(11) . . . . no O4 Cl1 O6 O5 -55.2(9) . . . . no O5 Cl1 O6 O3 -126.0(12) . . . . no O4 Cl1 O3 O6 -2(2) . . . . no O1 Cl1 O3 O6 -99.5(11) . . . . no O2 Cl1 O3 O6 149.0(11) . . . . no O5 Cl1 O3 O6 55.2(12) . . . . no O1 Cl1 O4 O5 171.2(8) . . . . no C6 N1 C2 C3 -0.4(5) . . . . no C1 N1 C2 C3 -175.3(3) . . . . no C1 N1 C2 C21 4.5(5) . . . . no C6 N1 C2 C21 179.4(3) . . . . no C1 N1 C6 C5 174.0(3) . . . . no C1 N1 C6 C61 -6.7(5) . . . . no C2 N1 C6 C5 -0.8(5) . . . . no C2 N1 C6 C61 178.4(3) . . . . no C441 N2 C44 C43 1.5(8) . . . . no C441 N2 C44 C45 -178.2(6) . . . . no C442 N2 C44 C43 -175.3(5) . . . . no C442 N2 C44 C45 5.0(8) . . . . no C3 C2 C21 C26 -107.6(5) . . . . no N1 C2 C3 C4 0.5(6) . . . . no C21 C2 C3 C4 -179.3(4) . . . . no N1 C2 C21 C22 -110.3(4) . . . . no N1 C2 C21 C26 72.6(5) . . . . no C3 C2 C21 C22 69.5(5) . . . . no Cl1 O3 O6 O5 -44.5(8) . . . . no C2 C3 C4 C5 0.7(6) . . . . no C2 C3 C4 C41 -177.9(4) . . . . no C3 C4 C41 C42 -20.8(6) . . . . no C3 C4 C41 C46 160.4(4) . . . . no C5 C4 C41 C46 -18.2(6) . . . . no C3 C4 C5 C6 -1.9(5) . . . . no C5 C4 C41 C42 160.6(4) . . . . no C41 C4 C5 C6 176.8(4) . . . . no Cl1 O4 O5 O6 -43.3(7) . . . . no C4 C5 C6 N1 2.0(5) . . . . no Cl1 O5 O6 O3 56.2(11) . . . . no O4 O5 O6 Cl1 56.1(10) . . . . no O4 O5 O6 O3 112.3(14) . . . . no C4 C5 C6 C61 -177.3(3) . . . . no N1 C6 C61 C62 117.5(4) . . . . no N1 C6 C61 C66 -64.7(5) . . . . no C5 C6 C61 C66 114.6(4) . . . . no C5 C6 C61 C62 -63.2(5) . . . . no C26 C21 C22 C23 -1.2(7) . . . . no C2 C21 C22 C23 -178.3(5) . . . . no C22 C21 C26 C25 -0.3(7) . . . . no C2 C21 C26 C25 176.7(4) . . . . no C21 C22 C23 C24 0.6(9) . . . . no C22 C23 C24 C25 1.7(10) . . . . no C23 C24 C25 C26 -3.2(10) . . . . no C24 C25 C26 C21 2.4(9) . . . . no C46 C41 C42 C43 0.1(6) . . . . no C4 C41 C42 C43 -178.8(4) . . . . no C42 C41 C46 C45 0.7(8) . . . . no C4 C41 C46 C45 179.6(5) . . . . no C41 C42 C43 C44 -0.5(6) . . . . no C42 C43 C44 C45 0.1(7) . . . . no C42 C43 C44 N2 -179.7(4) . . . . no C43 C44 C45 C46 0.7(8) . . . . no N2 C44 C45 C46 -179.6(5) . . . . no C44 C45 C46 C41 -1.1(9) . . . . no C6 C61 C62 C63 176.5(4) . . . . no C66 C61 C62 C63 -1.4(7) . . . . no C62 C61 C66 C65 -0.1(7) . . . . no C6 C61 C66 C65 -177.9(4) . . . . no C61 C62 C63 C64 2.3(8) . . . . no C62 C63 C64 C65 -1.7(9) . . . . no C63 C64 C65 C66 0.2(9) . . . . no C64 C65 C66 C61 0.7(8) . . . . no