Crystal structures of three hydrogen-bonded 1:2 compounds of chloranilic acid with 2-pyridone, 3-hy-droxy-pyridine and 4-hyroxypyridine.
Gotoh, Kazuma; Ishida, Hiroyuki; Acta crystallographica. Section E, Crystallographic communications 73 (2017) 1546–1550; doi:10.1107/S2056989017013536

data_2311444
_publ_section_title
;
 Crystal structures of three hydrogen-bonded 1:2 compounds of chloranilic
 acid with 2-pyridone, 3-hy-droxy-pyridine and 4-hyroxypyridine.
;
_journal_coeditor_code           LH5855
_journal_issue                   'Pt 10'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              1546
_journal_page_last               1550
_journal_paper_doi               10.1107/S2056989017013536
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          '2C5 H6 N O +, C6 Cl2 O4 2-'
_chemical_formula_moiety         '2(C5 H6 N O 1+), C6 Cl2 O4 2-'
_chemical_formula_sum            'C16 H12 Cl2 N2 O6'
_chemical_formula_weight         399.19
_chemical_name_common            'bis(4-hyroxypyridinium) chloranilate'
_chemical_name_systematic
'Bis(4-hyroxypyridinium) 2,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,4-diolate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                102.177(3)
_cell_angle_beta                 93.952(3)
_cell_angle_gamma                95.316(4)
_cell_formula_units_Z            2
_cell_length_a                   5.49136(13)
_cell_length_b                   8.2195(4)
_cell_length_c                   18.1382(9)
_cell_measurement_reflns_used    11077
_cell_measurement_temperature    120.0(10)
_cell_measurement_theta_max      30.09
_cell_measurement_theta_min      3.02
_cell_volume                     793.53(6)
_computing_cell_refinement
;
RAPID-AUTO (Rigaku, 2006)
;
_computing_data_collection
;
RAPID-AUTO (Rigaku, 2006)
;
_computing_data_reduction
;
RAPID-AUTO (Rigaku, 2006)
;
_computing_molecular_graphics
;
<i>ORTEP-3 for Windows</i> (Farrugia, 2012)
;
_computing_publication_material
;
CrystalStructure (Rigaku, 2010) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPIDII'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12373
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.983
_diffrn_reflns_theta_min         3.021
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.448
_exptl_absorpt_correction_T_max  0.948
_exptl_absorpt_correction_T_min  0.890
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(<i>NUMABS</i>; Higashi, 1999)
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.671
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             408.00
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.752
_refine_diff_density_min         -0.341
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4597
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0304
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0406P)^2^+0.3136P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0770
_refine_ls_wR_factor_ref         0.0798
_reflns_number_gt                4124
_reflns_number_total             4597
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            lh5855sup1.cif
_cod_data_source_block           III
_cod_original_cell_volume        793.52(6)
_cod_database_code               2311444
_shelx_hkl_checksum              6799
_shelx_res_checksum              80037