##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
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##############################################################################
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2012-11-06
_journal_date_accepted     2013-03-21
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2013
_journal_volume     69
_journal_issue      4
_journal_page_first     o610
_journal_page_last     o610
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536813007939
_journal_coeditor_code     LX2273
_publ_contact_author_name     'M. N. Ponnuswamy'
_publ_contact_author_address
;   Centre of Advanced Study in Crystallography and Biophysics
    University of Madras
    Guindy Campus
    Chennai 600 025
    India
;
_publ_contact_author_email     'mnpsy2004@yahoo.com'
_publ_contact_author_fax     '+9144 22352494'
_publ_contact_author_phone     '+9144 22300122'
_publ_section_title
;
2-Amino-6-methylpyridinium 4-hydroxybenzoate
;
loop_
    _publ_author_name
    _publ_author_address
    'V. Kannan'
;
      Department of Physics
      M.A.M. School of Engineering
      Siruganur,
      Tiruchirappalli 621 105
      India
;
    'P. Sugumar'
;
      Centre of Advanced Study in Crystallography and Biophysics
      University of Madras
      Guindy Campus
      Chennai 600 025
      India
;
    'S. Brahadeeswaran'
;
      Department of Physics
      Anna University
      BIT Campus
      Tiruchirappalli 620 024
      India.
;
    'M. N. Ponnuswamy'
;
      Centre of Advanced Study in Crystallography and Biophysics
      University of Madras
      Guindy Campus
      Chennai 600 025
      India
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2-Amino-6-methylpyridinium 4-hydroxybenzoate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C6 H9 N2 +, C7 H5 O3 -'
_chemical_formula_sum     'C13 H14 N2 O3'
_chemical_formula_iupac     'C6 H9 N2 +, C7 H5 O3 -'
_chemical_formula_weight     246.26
_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_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     11.9488(3)
_cell_length_b     9.2952(3)
_cell_length_c     12.4067(3)
_cell_angle_alpha     90.00
_cell_angle_beta     117.116(2)
_cell_angle_gamma     90.00
_cell_volume     1226.51(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2671
_cell_measurement_theta_min     1.91
_cell_measurement_theta_max     28.43
_cell_measurement_temperature     293(2)
_exptl_crystal_description     'Block'
_exptl_crystal_colour     'White Crystalline'
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.18
_exptl_crystal_size_min     0.17
_exptl_crystal_density_diffrn     1.334
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     520
_exptl_absorpt_coefficient_mu     0.096
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2008)'
_exptl_absorpt_correction_T_min     0.981
_exptl_absorpt_correction_T_max     0.984
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEXII CCD'
_diffrn_measurement_method     'ω and φ scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     11403
_diffrn_reflns_av_R_equivalents     0.0233
_diffrn_reflns_av_sigmaI/netI     0.0205
_diffrn_reflns_theta_min     1.91
_diffrn_reflns_theta_max     28.43
_diffrn_reflns_theta_full     28.43
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -16
_diffrn_reflns_limit_h_max     15
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3084
_reflns_number_gt     2471
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0529
_refine_ls_R_factor_gt     0.0412
_refine_ls_wR_factor_gt     0.1120
_refine_ls_wR_factor_ref     0.1218
_refine_ls_goodness_of_fit_ref     1.041
_refine_ls_restrained_S_all     1.041
_refine_ls_number_reflns     3084
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0582P)²+0.2532P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.253
_refine_diff_density_min     -0.202
_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'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2008)'
_computing_cell_refinement     'SAINT (Bruker, 2008)'
_computing_data_reduction     'SAINT (Bruker, 2008)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEP-3 for Windows
(Farrugia, 2012) and DIAMOND (Brandenburg,
1998)
;
_computing_publication_material
              'SHELXL97 (Sheldrick, 2008) 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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C2 0.63520(11) 0.65353(14) 0.57200(11) 0.0399(3) Uani d . 1 2 . .
    C C3 0.72343(13) 0.56067(17) 0.57177(14) 0.0528(3) Uani d . 1 2 . .
    H H3 0.7947 0.5393 0.6434 0.063 Uiso calc R 1 2 . .
    C C4 0.70557(14) 0.49803(16) 0.46291(15) 0.0562(4) Uani d . 1 2 . .
    H H4 0.7652 0.4342 0.4623 0.067 Uiso calc R 1 2 . .
    C C5 0.60208(14) 0.52912(14) 0.35780(13) 0.0486(3) Uani d . 1 2 . .
    H H5 0.5912 0.4868 0.2857 0.058 Uiso calc R 1 2 . .
    C C6 0.51139(12) 0.62547(13) 0.35806(11) 0.0384(3) Uani d . 1 2 . .
    C C7 0.64299(12) 0.72809(17) 0.68095(12) 0.0490(3) Uani d . 1 2 . .
    H H7A 0.5776 0.6934 0.6988 0.074 Uiso calc R 1 2 . .
    H H7B 0.6331 0.8298 0.6660 0.074 Uiso calc R 1 2 . .
    H H7C 0.7234 0.7094 0.7485 0.074 Uiso calc R 1 2 . .
    C C8 0.81847(10) 0.98339(13) 0.59471(10) 0.0370(3) Uani d . 1 2 . .
    C C9 0.90757(11) 0.92379(15) 0.70239(11) 0.0415(3) Uani d . 1 2 . .
    H H9 0.9070 0.9489 0.7747 0.050 Uiso calc R 1 2 . .
    C C10 0.99711(12) 0.82801(15) 0.70462(11) 0.0433(3) Uani d . 1 2 . .
    H H10 1.0556 0.7891 0.7778 0.052 Uiso calc R 1 2 . .
    C C11 0.99954(11) 0.79001(15) 0.59772(11) 0.0435(3) Uani d . 1 2 . .
    C C12 0.91149(14) 0.84879(19) 0.48968(12) 0.0592(4) Uani d . 1 2 . .
    H H12 0.9124 0.8242 0.4175 0.071 Uiso calc R 1 2 . .
    C C13 0.82247(13) 0.94363(18) 0.48875(12) 0.0542(4) Uani d . 1 2 . .
    H H13 0.7637 0.9819 0.4154 0.065 Uiso calc R 1 2 . .
    C C14 0.72117(10) 1.08629(13) 0.59372(10) 0.0369(3) Uani d . 1 2 . .
    N N1 0.53173(9) 0.68267(11) 0.46589(8) 0.0359(2) Uani d . 1 2 . .
    H H1 0.4763 0.7405 0.4674 0.043 Uiso calc R 1 2 . .
    N N2 0.40790(11) 0.66254(13) 0.26020(9) 0.0482(3) Uani d . 1 2 . .
    H H2A 0.3555 0.7216 0.2661 0.058 Uiso calc R 1 2 . .
    H H2B 0.3930 0.6276 0.1908 0.058 Uiso calc R 1 2 . .
    O O1 0.63458(8) 1.12882(11) 0.49535(8) 0.0503(3) Uani d . 1 2 . .
    O O2 0.73063(8) 1.12516(11) 0.69528(8) 0.0474(2) Uani d . 1 2 . .
    O O3 1.08494(10) 0.69729(13) 0.59355(10) 0.0598(3) Uani d . 1 2 . .
    H H3A 1.145(2) 0.672(2) 0.675(2) 0.089(6) Uiso d . 1 2 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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
    C2 N1 . 1.3606(15) ?
    C2 C3 . 1.3634(18) ?
    C2 C7 . 1.4837(18) ?
    C3 C4 . 1.395(2) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.358(2) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.4070(17) ?
    C5 H5 . 0.9300 ?
    C6 N2 . 1.3241(16) ?
    C6 N1 . 1.3547(15) ?
    C7 H7A . 0.9600 ?
    C7 H7B . 0.9600 ?
    C7 H7C . 0.9600 ?
    C8 C13 . 1.3873(17) ?
    C8 C9 . 1.3887(16) ?
    C8 C14 . 1.5013(16) ?
    C9 C10 . 1.3825(17) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.3855(17) ?
    C10 H10 . 0.9300 ?
    C11 O3 . 1.3546(15) ?
    C11 C12 . 1.3844(18) ?
    C12 C13 . 1.3775(19) ?
    C12 H12 . 0.9300 ?
    C13 H13 . 0.9300 ?
    C14 O1 . 1.2511(14) ?
    C14 O2 . 1.2653(14) ?
    N1 H1 . 0.8600 ?
    N2 H2A . 0.8600 ?
    N2 H2B . 0.8600 ?
    O3 H3A . 0.97(2) ?
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
    N1 C2 C3 . . 119.11(12) ?
    N1 C2 C7 . . 116.13(11) ?
    C3 C2 C7 . . 124.75(12) ?
    C2 C3 C4 . . 119.27(13) ?
    C2 C3 H3 . . 120.4 ?
    C4 C3 H3 . . 120.4 ?
    C5 C4 C3 . . 120.77(12) ?
    C5 C4 H4 . . 119.6 ?
    C3 C4 H4 . . 119.6 ?
    C4 C5 C6 . . 119.91(12) ?
    C4 C5 H5 . . 120.0 ?
    C6 C5 H5 . . 120.0 ?
    N2 C6 N1 . . 118.40(11) ?
    N2 C6 C5 . . 124.19(12) ?
    N1 C6 C5 . . 117.41(12) ?
    C2 C7 H7A . . 109.5 ?
    C2 C7 H7B . . 109.5 ?
    H7A C7 H7B . . 109.5 ?
    C2 C7 H7C . . 109.5 ?
    H7A C7 H7C . . 109.5 ?
    H7B C7 H7C . . 109.5 ?
    C13 C8 C9 . . 117.58(11) ?
    C13 C8 C14 . . 121.54(11) ?
    C9 C8 C14 . . 120.88(11) ?
    C10 C9 C8 . . 121.54(11) ?
    C10 C9 H9 . . 119.2 ?
    C8 C9 H9 . . 119.2 ?
    C9 C10 C11 . . 119.92(11) ?
    C9 C10 H10 . . 120.0 ?
    C11 C10 H10 . . 120.0 ?
    O3 C11 C12 . . 117.87(12) ?
    O3 C11 C10 . . 122.92(11) ?
    C12 C11 C10 . . 119.21(12) ?
    C13 C12 C11 . . 120.25(12) ?
    C13 C12 H12 . . 119.9 ?
    C11 C12 H12 . . 119.9 ?
    C12 C13 C8 . . 121.50(12) ?
    C12 C13 H13 . . 119.2 ?
    C8 C13 H13 . . 119.2 ?
    O1 C14 O2 . . 122.68(11) ?
    O1 C14 C8 . . 120.15(11) ?
    O2 C14 C8 . . 117.16(10) ?
    C6 N1 C2 . . 123.52(10) ?
    C6 N1 H1 . . 118.2 ?
    C2 N1 H1 . . 118.2 ?
    C6 N2 H2A . . 120.0 ?
    C6 N2 H2B . . 120.0 ?
    H2A N2 H2B . . 120.0 ?
    C11 O3 H3A . . 109.1(12) ?
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
    N1 C2 C3 C4 . . . . 0.1(2) ?
    C7 C2 C3 C4 . . . . -179.57(13) ?
    C2 C3 C4 C5 . . . . 0.3(2) ?
    C3 C4 C5 C6 . . . . 0.0(2) ?
    C4 C5 C6 N2 . . . . 179.79(13) ?
    C4 C5 C6 N1 . . . . -0.64(19) ?
    C13 C8 C9 C10 . . . . -0.1(2) ?
    C14 C8 C9 C10 . . . . 179.48(12) ?
    C8 C9 C10 C11 . . . . 0.3(2) ?
    C9 C10 C11 O3 . . . . 179.75(13) ?
    C9 C10 C11 C12 . . . . -0.1(2) ?
    O3 C11 C12 C13 . . . . 179.97(15) ?
    C10 C11 C12 C13 . . . . -0.1(3) ?
    C11 C12 C13 C8 . . . . 0.3(3) ?
    C9 C8 C13 C12 . . . . -0.1(2) ?
    C14 C8 C13 C12 . . . . -179.76(14) ?
    C13 C8 C14 O1 . . . . 6.19(19) ?
    C9 C8 C14 O1 . . . . -173.41(12) ?
    C13 C8 C14 O2 . . . . -174.60(12) ?
    C9 C8 C14 O2 . . . . 5.80(18) ?
    N2 C6 N1 C2 . . . . -179.31(11) ?
    C5 C6 N1 C2 . . . . 1.10(17) ?
    C3 C2 N1 C6 . . . . -0.82(18) ?
    C7 C2 N1 C6 . . . . 178.85(11) ?
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
    N1 H1 O1 3_676 0.86 2.00 2.8499(13) 169.2
    N2 H2A O2 3_676 0.86 1.94 2.7879(14) 167.8
    N2 H2B O1 2_645 0.86 2.18 2.9902(14) 157.2
    O3 H3A O2 2_746 0.97(2) 1.67(2) 2.6281(14) 168.5(19)
    C4 H4 O3 3_766 0.93 2.51 3.4134(17) 163.3
