##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
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data_global
_audit_creation_method     'by CrystalStructure 3.7'
_journal_date_recd_electronic     2009-02-20
_journal_date_accepted     2009-02-21
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      3
_journal_page_first     o614
_journal_page_last     o614
_journal_paper_category     QO
_journal_coeditor_code     TK2376
_publ_contact_author_name     ' Prof. Hiroyuki Ishida'
_publ_contact_author_address
;
Department of Chemistry
Faculty of Science
Okayama University
Okayama 700-8530
Japan
;
_publ_contact_author_email     ishidah@cc.okayama-u.ac.jp
_publ_contact_author_fax     ' 81-86-251-7832'
_publ_contact_author_phone     ' 81-86-251-7832'
_publ_section_title
;
2-Carboxypyridinium hydrogen chloranilate
;
loop_
    _publ_author_name
    _publ_author_address
    'Gotoh, Kazuma'
;
Department of Chemistry
Faculty of Science
Okayama University
Okayama 700-8530
Japan
;
    'Nagoshi, Hirokazu'
;
Department of Chemistry
Faculty of Science
Okayama University
Okayama 700-8530
Japan
;
    'Ishida, Hiroyuki'
;
Department of Chemistry
Faculty of Science
Okayama University
Okayama 700-8530
Japan
;
data_I
_chemical_name_systematic
;
2-Carboxypyridinium hydrogen chloranilate
;
_chemical_formula_moiety     'C6 H6 N O2 +, C6 H Cl2 O4 -'
_chemical_formula_sum     'C12 H7 Cl2 N O6 '
_chemical_formula_iupac     'C6 H6 N O2 +, C6 H Cl2 O4 -'
_chemical_formula_weight     332.10
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_site_id
    _symmetry_equiv_pos_as_xyz
    1 '+X,+Y,+Z'
    2 '-X,1/2+Y,1/2-Z'
    3 '-X,-Y,-Z'
    4 '+X,1/2-Y,1/2+Z'
_cell_length_a     9.4166(8)
_cell_length_b     19.6900(16)
_cell_length_c     6.7089(6)
_cell_angle_alpha     90
_cell_angle_beta     99.043(3)
_cell_angle_gamma     90
_cell_volume     1228.45(18)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     7392
_cell_measurement_theta_min     3.0
_cell_measurement_theta_max     30.0
_cell_measurement_temperature     103.0(10)
_exptl_crystal_description     'platelet'
_exptl_crystal_colour     'dark purple'
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.23
_exptl_crystal_density_diffrn     1.795
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     672.00
_exptl_absorpt_coefficient_mu     0.557
_exptl_absorpt_correction_type     'Multi-scan'
_exptl_absorpt_process_details     '(<i>ABSCOR</i>; Higashi, 1995)'
_exptl_absorpt_correction_T_min     0.847
_exptl_absorpt_correction_T_max     0.880
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type     'Rigaku R-AXIS RAPID-II'
_diffrn_measurement_method     \w
_diffrn_detector_area_resol_mean     10.00
_diffrn_reflns_number     9710
_diffrn_reflns_av_R_equivalents     0.047
_diffrn_reflns_theta_max     30.0
_diffrn_reflns_theta_full     25.0
_diffrn_measured_fraction_theta_max     0.959
_diffrn_measured_fraction_theta_full     0.981
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -27
_diffrn_reflns_limit_k_max     27
_diffrn_reflns_limit_l_min     -8
_diffrn_reflns_limit_l_max     9
_refine_special_details
;
Refinement of <i>F</i>^2^ against ALL reflections. The weighted <i>R</i>-factor
<i>wR</i> and goodness of fit <i>S</i> are based on <i>F</i>^2^, conventional
<i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for
negative <i>F</i>^2^. The threshold expression of <i>F</i>^2^ >
\s(<i>F</i>^2^) is used only for calculating <i>R</i>-factors(gt) <i>etc</i>.
and is not relevant to the choice of reflections for refinement.
<i>R</i>-factors based on <i>F</i>^2^ are statistically about twice as large
as those based on <i>F</i>, and <i>R</i>- factors based on ALL data will be
even larger.
;
_reflns_number_total     3433
_reflns_number_gt     2228
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_R_factor_all     0.073
_refine_ls_R_factor_gt     0.045
_refine_ls_wR_factor_gt     0.118
_refine_ls_wR_factor_ref     0.144
_refine_ls_goodness_of_fit_ref     1.10
_refine_ls_restrained_S_all     1.10
_refine_ls_number_reflns     3433
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
            'w = 1/[\s^2^(Fo^2^)+(0.0659P)^2^+0.8975P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     ?
_refine_ls_shift/su_max_lt     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.47
_refine_diff_density_min     -0.92
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    'Cl' 'Cl' 0.1484 0.1585
                         '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'
_computing_data_collection     'PROCESS-AUTO (Rigaku/MSC, 2004)'
_computing_cell_refinement     'PROCESS-AUTO (Rigaku/MSC, 2004)'
_computing_data_reduction     'CrystalStructure (Rigaku/MSC, 2004)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
                   'CrystalStructure (Rigaku/MSC, 2004) and PLATON (Spek, 2009)'
loop_
    _atom_site_type_symbol
    _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
    Cl Cl1 -0.17894(6) 0.28996(3) 0.27912(9) 0.02060(16) Uani d . 1 . .
    Cl Cl2 0.46528(6) 0.29140(3) 0.10812(9) 0.02077(16) Uani d . 1 . .
    O O1 0.00723(19) 0.40867(8) 0.2367(3) 0.0218(4) Uani d . 1 . .
    O O2 0.01147(19) 0.17042(9) 0.2397(3) 0.0184(3) Uani d . 1 . .
    O O3 0.27117(18) 0.17271(8) 0.1488(3) 0.0196(4) Uani d . 1 . .
    O O4 0.27772(19) 0.41277(8) 0.1577(3) 0.0209(4) Uani d . 1 . .
    O O5 0.12383(18) 0.45615(9) 0.6917(3) 0.0215(4) Uani d . 1 . .
    O O6 0.3466(2) 0.47658(10) 0.8601(3) 0.0265(4) Uani d . 1 . .
    N N1 0.1860(2) 0.52690(11) 0.3720(3) 0.0199(4) Uani d . 1 . .
    C C1 0.0667(2) 0.35416(11) 0.2174(3) 0.0164(4) Uani d . 1 . .
    C C2 -0.0036(2) 0.28950(11) 0.2347(3) 0.0160(4) Uani d . 1 . .
    C C3 0.0678(2) 0.23079(11) 0.2188(3) 0.0154(4) Uani d . 1 . .
    C C4 0.2206(2) 0.22965(11) 0.1715(3) 0.0155(4) Uani d . 1 . .
    C C5 0.2899(2) 0.29272(11) 0.1544(4) 0.0170(4) Uani d . 1 . .
    C C6 0.2232(2) 0.35480(12) 0.1732(3) 0.0165(4) Uani d . 1 . .
    C C7 0.2794(3) 0.52837(12) 0.5464(4) 0.0198(5) Uani d . 1 . .
    C C8 0.3984(3) 0.56970(13) 0.5626(4) 0.0229(5) Uani d . 1 . .
    H H8 0.4656 0.5708 0.6840 0.027 Uiso calc R 1 . .
    C C9 0.4194(3) 0.60996(13) 0.3987(4) 0.0262(5) Uani d . 1 . .
    H H9 0.5010 0.6388 0.4077 0.031 Uiso calc R 1 . .
    C C10 0.3206(3) 0.60759(13) 0.2230(4) 0.0268(5) Uani d . 1 . .
    H H10 0.3332 0.6352 0.1109 0.032 Uiso calc R 1 . .
    C C11 0.2035(3) 0.56488(13) 0.2118(4) 0.0239(5) Uani d . 1 . .
    H H11 0.1357 0.5624 0.0913 0.029 Uiso calc R 1 . .
    C C12 0.2418(3) 0.48289(12) 0.7090(4) 0.0195(5) Uani d . 1 . .
    H H1 0.109(5) 0.498(2) 0.363(6) 0.053(11) Uiso d . 1 . .
    H H2 0.071(4) 0.1437(17) 0.227(5) 0.032(9) Uiso d . 1 . .
    H H6 0.319(4) 0.4534(18) 0.964(6) 0.043(10) Uiso d . 1 . .
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
    Cl1 0.0146(3) 0.0253(3) 0.0233(3) 0.0013(2) 0.0076(2) -0.0006(2)
    Cl2 0.0151(3) 0.0258(3) 0.0230(3) -0.0018(2) 0.0080(2) -0.0011(2)
    O1 0.0207(8) 0.0196(8) 0.0256(9) 0.0020(7) 0.0051(7) -0.0022(7)
    O2 0.0163(8) 0.0164(7) 0.0238(9) 0.0013(7) 0.0074(7) -0.0008(7)
    O3 0.0176(8) 0.0201(8) 0.0220(8) 0.0016(7) 0.0063(7) -0.0008(7)
    O4 0.0232(9) 0.0200(8) 0.0210(9) -0.0027(7) 0.0083(7) 0.0019(6)
    O5 0.0177(8) 0.0212(8) 0.0274(9) -0.0017(7) 0.0094(7) 0.0018(7)
    O6 0.0221(9) 0.0336(10) 0.0235(9) -0.0063(8) 0.0024(7) 0.0050(8)
    N1 0.0145(9) 0.0229(10) 0.0229(10) -0.0018(8) 0.0050(8) 0.0000(8)
    C1 0.0182(10) 0.0180(10) 0.0130(10) 0.0007(9) 0.0020(8) 0.0001(8)
    C2 0.0130(10) 0.0197(10) 0.0152(10) 0.0009(8) 0.0023(8) -0.0019(8)
    C3 0.0154(10) 0.0183(10) 0.0132(10) -0.0002(8) 0.0048(8) 0.0005(8)
    C4 0.0149(10) 0.0193(10) 0.0132(10) 0.0009(8) 0.0048(8) 0.0003(8)
    C5 0.0132(10) 0.0207(10) 0.0176(10) -0.0013(9) 0.0041(8) -0.0006(9)
    C6 0.0165(10) 0.0204(10) 0.0133(10) -0.0014(9) 0.0039(8) -0.0011(8)
    C7 0.0179(11) 0.0184(11) 0.0241(12) 0.0001(9) 0.0067(9) -0.0006(9)
    C8 0.0188(11) 0.0236(12) 0.0272(13) 0.0000(10) 0.0066(10) -0.0018(10)
    C9 0.0223(12) 0.0231(12) 0.0355(14) -0.0031(10) 0.0118(11) 0.0023(11)
    C10 0.0292(13) 0.0248(12) 0.0291(13) 0.0006(11) 0.0129(11) 0.0049(10)
    C11 0.0229(12) 0.0270(12) 0.0221(12) 0.0049(10) 0.0051(10) 0.0028(10)
    C12 0.0210(11) 0.0193(10) 0.0197(11) -0.0002(9) 0.0076(9) -0.0021(9)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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
    Cl1 C2 . 1.723(2) ?
    Cl2 C5 . 1.727(2) ?
    O1 C1 . 1.227(3) ?
    O2 C3 . 1.318(3) ?
    O2 H2 . 0.79(3) ?
    O3 C4 . 1.237(3) ?
    O4 C6 . 1.263(3) ?
    O5 C12 . 1.218(3) ?
    O6 C12 . 1.305(3) ?
    O6 H6 . 0.90(4) ?
    N1 C11 . 1.340(3) ?
    N1 C7 . 1.349(3) ?
    N1 H1 . 0.92(4) ?
    C1 C2 . 1.448(3) ?
    C1 C6 . 1.548(3) ?
    C2 C3 . 1.350(3) ?
    C3 C4 . 1.521(3) ?
    C4 C5 . 1.416(3) ?
    C5 C6 . 1.389(3) ?
    C7 C8 . 1.375(3) ?
    C7 C12 . 1.497(3) ?
    C8 C9 . 1.394(4) ?
    C8 H8 . 0.9500 ?
    C9 C10 . 1.383(4) ?
    C9 H9 . 0.9500 ?
    C10 C11 . 1.379(4) ?
    C10 H10 . 0.9500 ?
    C11 H11 . 0.9500 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C3 O2 H2 . . 107(3) ?
    C12 O6 H6 . . 112(2) ?
    C11 N1 C7 . . 122.5(2) ?
    C11 N1 H1 . . 119(2) ?
    C7 N1 H1 . . 118(2) ?
    O1 C1 C2 . . 122.6(2) ?
    O1 C1 C6 . . 118.5(2) ?
    C2 C1 C6 . . 118.91(19) ?
    C3 C2 C1 . . 120.4(2) ?
    C3 C2 Cl1 . . 121.40(18) ?
    C1 C2 Cl1 . . 118.15(17) ?
    O2 C3 C2 . . 123.3(2) ?
    O2 C3 C4 . . 114.75(19) ?
    C2 C3 C4 . . 121.9(2) ?
    O3 C4 C5 . . 126.4(2) ?
    O3 C4 C3 . . 115.7(2) ?
    C5 C4 C3 . . 117.85(19) ?
    C6 C5 C4 . . 122.9(2) ?
    C6 C5 Cl2 . . 119.23(17) ?
    C4 C5 Cl2 . . 117.86(17) ?
    O4 C6 C5 . . 126.3(2) ?
    O4 C6 C1 . . 115.8(2) ?
    C5 C6 C1 . . 117.90(19) ?
    N1 C7 C8 . . 119.6(2) ?
    N1 C7 C12 . . 115.0(2) ?
    C8 C7 C12 . . 125.4(2) ?
    C7 C8 C9 . . 119.3(2) ?
    C7 C8 H8 . . 120.4 ?
    C9 C8 H8 . . 120.4 ?
    C10 C9 C8 . . 119.5(2) ?
    C10 C9 H9 . . 120.2 ?
    C8 C9 H9 . . 120.2 ?
    C11 C10 C9 . . 119.5(2) ?
    C11 C10 H10 . . 120.3 ?
    C9 C10 H10 . . 120.3 ?
    N1 C11 C10 . . 119.7(2) ?
    N1 C11 H11 . . 120.2 ?
    C10 C11 H11 . . 120.2 ?
    O5 C12 O6 . . 126.9(2) ?
    O5 C12 C7 . . 120.4(2) ?
    O6 C12 C7 . . 112.7(2) ?
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_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O1 C1 C2 C3 . . . . -177.9(2) ?
    C6 C1 C2 C3 . . . . 2.1(3) ?
    O1 C1 C2 Cl1 . . . . 1.3(3) ?
    C6 C1 C2 Cl1 . . . . -178.77(16) ?
    C1 C2 C3 O2 . . . . 177.7(2) ?
    Cl1 C2 C3 O2 . . . . -1.4(3) ?
    C1 C2 C3 C4 . . . . -3.3(3) ?
    Cl1 C2 C3 C4 . . . . 177.58(16) ?
    O2 C3 C4 O3 . . . . 3.3(3) ?
    C2 C3 C4 O3 . . . . -175.8(2) ?
    O2 C3 C4 C5 . . . . -177.73(19) ?
    C2 C3 C4 C5 . . . . 3.2(3) ?
    O3 C4 C5 C6 . . . . 177.0(2) ?
    C3 C4 C5 C6 . . . . -1.8(3) ?
    O3 C4 C5 Cl2 . . . . -3.0(3) ?
    C3 C4 C5 Cl2 . . . . 178.11(16) ?
    C4 C5 C6 O4 . . . . -179.2(2) ?
    Cl2 C5 C6 O4 . . . . 0.8(3) ?
    C4 C5 C6 C1 . . . . 0.7(3) ?
    Cl2 C5 C6 C1 . . . . -179.21(16) ?
    O1 C1 C6 O4 . . . . -0.9(3) ?
    C2 C1 C6 O4 . . . . 179.2(2) ?
    O1 C1 C6 C5 . . . . 179.2(2) ?
    C2 C1 C6 C5 . . . . -0.7(3) ?
    C11 N1 C7 C8 . . . . -0.6(4) ?
    C11 N1 C7 C12 . . . . 179.6(2) ?
    N1 C7 C8 C9 . . . . 0.7(4) ?
    C12 C7 C8 C9 . . . . -179.5(2) ?
    C7 C8 C9 C10 . . . . -0.1(4) ?
    C8 C9 C10 C11 . . . . -0.7(4) ?
    C7 N1 C11 C10 . . . . -0.2(4) ?
    C9 C10 C11 N1 . . . . 0.8(4) ?
    N1 C7 C12 O5 . . . . -11.4(3) ?
    C8 C7 C12 O5 . . . . 168.8(2) ?
    N1 C7 C12 O6 . . . . 168.4(2) ?
    C8 C7 C12 O6 . . . . -11.4(3) ?
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
    N1 H1 O1 . 0.92(4) 2.11(3) 2.932(2) 147(3) y
    N1 H1 O5 . 0.92(4) 2.33(4) 2.698(2) 103(2) n
    N1 H1 O5 3_566 0.92(4) 2.34(4) 2.900(2) 119(3) n
    O2 H2 O3 . 0.79(3) 2.11(3) 2.612(2) 122(3) n
    O2 H2 O5 4_554 0.79(3) 2.05(3) 2.746(2) 148(3) y
    O6 H6 O4 1_556 0.90(3) 1.63(3) 2.528(2) 177.1(15) y
    C8 H8 O4 3_666 0.95 2.50 3.338(3) 147 y
    C9 H9 O3 2_655 0.95 2.33 3.227(3) 156 y
    C11 H11 O1 3_565 0.95 2.46 3.374(3) 162 y