#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/45/2204524.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_2204524 loop_ _publ_author_name 'Hiroyuki Ishida' _publ_section_title ; Bis(2,4,6-trimethylpyridinium) chloranilate ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o2005 _journal_page_last o2006 _journal_paper_doi 10.1107/S1600536804025334 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac '2C8 H12 N 1+, C6 Cl2 O4 2-' _chemical_formula_moiety '2C8 H12 N 1+, C6 Cl2 O4 2-' _chemical_formula_sum 'C22 H24 Cl2 N2 O4' _chemical_formula_weight 451.35 _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 115.456(12) _cell_angle_beta 112.034(10) _cell_angle_gamma 94.799(13) _cell_formula_units_Z 1 _cell_length_a 8.4902(9) _cell_length_b 9.0205(16) _cell_length_c 9.3236(14) _cell_measurement_reflns_used 25 _cell_measurement_temperature 296 _cell_measurement_theta_max 12.5 _cell_measurement_theta_min 10.5 _cell_volume 571.48(18) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1990) ; _computing_data_reduction 'TEXSAN for Windows (MSC, 1997-1999)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'PLATON (Spek, 2003)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 296 _diffrn_measured_fraction_theta_full 1.00 _diffrn_measured_fraction_theta_max 1.00 _diffrn_measurement_device 'Rigaku AFC-5R' _diffrn_measurement_method \w-2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.014 _diffrn_reflns_av_sigmaI/netI 0.0417 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 2780 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_reflns_theta_full 27.5 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_min 2.62 _diffrn_standards_decay_% 0.45 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.314 _exptl_absorpt_correction_T_max 0.940 _exptl_absorpt_correction_T_min 0.895 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour brown _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 236 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.22 _refine_diff_density_min -0.31 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.01 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 143 _refine_ls_number_reflns 2615 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.01 _refine_ls_R_factor_all 0.087 _refine_ls_R_factor_gt 0.046 _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^)+(0.051P)^2^+0.175P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.106 _refine_ls_wR_factor_ref 0.122 _reflns_number_gt 1704 _reflns_number_total 2615 _reflns_threshold_expression >2\s(I) _cod_data_source_file kp6006.cif _cod_data_source_block I _cod_database_code 2204524 _cod_database_fobs_code 2204524 loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x, -y, -z' 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 Cl 0.97851(9) 0.90062(9) 0.12221(8) 0.0634(2) Uani d . 1 Cl O1 0.7611(2) 0.7043(2) 0.2076(2) 0.0579(5) Uani d . 1 O O2 1.2070(3) 1.2135(2) 0.4692(2) 0.0663(5) Uani d . 1 O N 0.6331(3) 0.4395(3) 0.2357(2) 0.0464(5) Uani d . 1 N C1 0.8768(3) 0.8412(3) 0.3384(3) 0.0412(5) Uani d . 1 C C2 0.9916(3) 0.9509(3) 0.3293(3) 0.0419(5) Uani d . 1 C C3 1.1118(3) 1.1101(3) 0.4770(3) 0.0429(5) Uani d . 1 C C4 0.4803(3) 0.4105(3) 0.2456(3) 0.0455(5) Uani d . 1 C C5 0.4314(3) 0.2695(3) 0.2595(3) 0.0520(6) Uani d . 1 C C6 0.5347(3) 0.1593(3) 0.2593(3) 0.0560(6) Uani d . 1 C C7 0.6899(4) 0.1955(4) 0.2474(4) 0.0598(7) Uani d . 1 C C8 0.7394(3) 0.3382(3) 0.2371(3) 0.0549(6) Uani d . 1 C C9 0.3746(3) 0.5330(3) 0.2393(4) 0.0599(7) Uani d . 1 C C10 0.4829(5) 0.0040(4) 0.2743(5) 0.0847(10) Uani d . 1 C C11 0.9090(4) 0.3891(4) 0.2307(5) 0.0804(9) Uani d . 1 C H1 0.674(4) 0.538(4) 0.240(4) 0.079(9) Uiso d . 1 H H2 0.3277 0.2485 0.2691 0.062 Uiso calc R 1 H H3 0.7611 0.1225 0.2463 0.072 Uiso calc R 1 H H4 0.4533 0.6457 0.2953 0.090 Uiso calc R 1 H H5 0.3058 0.5352 0.3013 0.090 Uiso calc R 1 H H6 0.2965 0.4971 0.1172 0.090 Uiso calc R 1 H H7 0.3607 -0.0187 0.2509 0.127 Uiso calc R 1 H H8 0.5567 0.0259 0.3925 0.127 Uiso calc R 1 H H9 0.4982 -0.0937 0.1889 0.127 Uiso calc R 1 H H10 0.8814 0.3828 0.1182 0.121 Uiso calc R 1 H H11 0.9779 0.3125 0.2441 0.121 Uiso calc R 1 H H12 0.9760 0.5044 0.3258 0.121 Uiso calc R 1 H 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 Cl 0.0733(5) 0.0690(4) 0.0382(3) -0.0015(3) 0.0299(3) 0.0191(3) O1 0.0672(11) 0.0474(9) 0.0398(8) -0.0093(8) 0.0225(8) 0.0125(7) O2 0.0780(13) 0.0580(11) 0.0489(10) -0.0155(9) 0.0323(9) 0.0188(8) N 0.0471(11) 0.0403(11) 0.0424(10) 0.0022(9) 0.0198(9) 0.0154(8) C1 0.0460(12) 0.0375(11) 0.0368(10) 0.0066(10) 0.0197(9) 0.0163(9) C2 0.0486(13) 0.0441(12) 0.0324(10) 0.0066(10) 0.0217(9) 0.0170(9) C3 0.0458(12) 0.0452(12) 0.0394(11) 0.0076(10) 0.0228(10) 0.0207(10) C4 0.0416(12) 0.0468(13) 0.0366(10) 0.0039(10) 0.0155(9) 0.0152(10) C5 0.0436(13) 0.0593(15) 0.0512(13) 0.0050(12) 0.0208(11) 0.0286(12) C6 0.0552(15) 0.0554(15) 0.0538(14) 0.0085(13) 0.0198(12) 0.0300(12) C7 0.0578(16) 0.0583(16) 0.0697(17) 0.0219(13) 0.0308(14) 0.0347(14) C8 0.0510(14) 0.0575(15) 0.0517(13) 0.0111(13) 0.0274(12) 0.0210(12) C9 0.0544(16) 0.0568(16) 0.0662(16) 0.0159(13) 0.0267(13) 0.0296(13) C10 0.086(2) 0.079(2) 0.109(3) 0.0192(18) 0.043(2) 0.066(2) C11 0.068(2) 0.085(2) 0.108(3) 0.0268(18) 0.060(2) 0.047(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 1 3 -2 2 -1 0 0 0 -2 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle C8 N C4 . 123.6(2) C8 N H1 . 116.6(19) C4 N H1 . 119.5(19) O1 C1 C2 . 125.42(19) O1 C1 C3 2_776 116.55(18) C2 C1 C3 2_776 118.03(18) C1 C2 C3 . 123.99(18) C1 C2 Cl . 118.86(16) C3 C2 Cl . 116.97(15) O2 C3 C2 . 124.79(19) O2 C3 C1 2_776 117.33(19) C2 C3 C1 2_776 117.87(18) N C4 C5 . 118.2(2) N C4 C9 . 117.4(2) C5 C4 C9 . 124.4(2) C4 C5 C6 . 120.7(2) C4 C5 H2 . 119.7 C6 C5 H2 . 119.7 C5 C6 C7 . 118.3(2) C5 C6 C10 . 121.3(2) C7 C6 C10 . 120.4(3) C8 C7 C6 . 120.6(3) C8 C7 H3 . 119.7 C6 C7 H3 . 119.7 N C8 C7 . 118.6(2) N C8 C11 . 117.9(2) C7 C8 C11 . 123.6(3) C4 C9 H4 . 109.5 C4 C9 H5 . 109.5 C4 C9 H6 . 109.5 H4 C9 H5 . 109.5 H4 C9 H6 . 109.5 H5 C9 H6 . 109.5 C6 C10 H7 . 109.5 C6 C10 H8 . 109.5 C6 C10 H9 . 109.5 H7 C10 H8 . 109.5 H7 C10 H9 . 109.5 H8 C10 H9 . 109.5 C8 C11 H10 . 109.5 C8 C11 H11 . 109.5 C8 C11 H12 . 109.5 H10 C11 H11 . 109.5 H10 C11 H12 . 109.5 H11 C11 H12 . 109.5 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 Cl C2 . 1.739(2) yes O1 C1 . 1.257(3) yes O2 C3 . 1.227(2) yes C1 C2 . 1.381(3) yes C1 C3 2_776 1.543(3) yes C2 C3 . 1.414(3) yes C3 C1 2_776 1.543(3) ? N C8 . 1.338(3) yes N C4 . 1.347(3) yes N H1 . 0.91(3) ? C4 C5 . 1.379(3) ? C4 C9 . 1.487(3) ? C5 C6 . 1.380(4) ? C5 H2 . 0.93 ? C6 C7 . 1.387(4) ? C6 C10 . 1.512(4) ? C7 C8 . 1.374(4) ? C7 H3 . 0.93 ? C8 C11 . 1.505(3) ? C9 H4 . 0.96 ? C9 H5 . 0.96 ? C9 H6 . 0.96 ? C10 H7 . 0.96 ? C10 H8 . 0.96 ? C10 H9 . 0.96 ? C11 H10 . 0.96 ? C11 H11 . 0.96 ? C11 H12 . 0.96 ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 N 2.697(3) . no O1 C11 3.260(5) . no O1 C9 3.404(3) 2_665 no O2 N 2.880(3) 2_776 no O2 C4 3.327(3) 2_776 no O2 C5 3.345(4) 1_665 no O2 C9 3.360(4) 2_776 no C2 C7 3.597(5) 1_565 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 N H1 O1 . 0.91(4) 1.81(4) 2.697(3) 168(3) yes N H1 O2 2_776 0.91(4) 2.40(3) 2.880(3) 114(2) yes C5 H2 O2 1_445 0.93 2.55 3.345(4) 143 yes C9 H6 O1 2_665 0.96 2.59 3.404(3) 142 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_site_symmetry_1 _geom_torsion_site_symmetry_4 _geom_torsion O1 C1 C2 C3 . . 175.3(2) C3 C1 C2 C3 2_776 . -3.9(4) O1 C1 C2 Cl . . 0.3(3) C3 C1 C2 Cl 2_776 . -178.84(17) C1 C2 C3 O2 . . -175.5(2) Cl C2 C3 O2 . . -0.4(3) C1 C2 C3 C1 . 2_776 3.9(4) Cl C2 C3 C1 . 2_776 178.92(17) C8 N C4 C5 . . 0.5(3) C8 N C4 C9 . . -179.0(2) N C4 C5 C6 . . -1.4(3) C9 C4 C5 C6 . . 178.1(2) C4 C5 C6 C7 . . 0.9(4) C4 C5 C6 C10 . . -179.9(3) C5 C6 C7 C8 . . 0.4(4) C10 C6 C7 C8 . . -178.8(3) C4 N C8 C7 . . 0.7(4) C4 N C8 C11 . . -178.2(2) C6 C7 C8 N . . -1.2(4) C6 C7 C8 C11 . . 177.7(3) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139067137