##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# 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 data    # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_database_code_depnum_ccdc_archive 'CCDC 1478169'
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2-Amino-6-methylpyridinium 2-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     tetragonal
_symmetry_space_group_name_H-M     'I 41/a'
_symmetry_space_group_name_Hall     '-I 4ad'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y+1/2, z'
    '-y+3/4, x+1/4, z+1/4'
    'y+1/4, -x+1/4, z+1/4'
    'x+1/2, y+1/2, z+1/2'
    '-x+1/2, -y+1, z+1/2'
    '-y+5/4, x+3/4, z+3/4'
    'y+3/4, -x+3/4, z+3/4'
    '-x, -y, -z'
    'x, y-1/2, -z'
    'y-3/4, -x-1/4, -z-1/4'
    '-y-1/4, x-1/4, -z-1/4'
    '-x+1/2, -y+1/2, -z+1/2'
    'x+1/2, y, -z+1/2'
    'y-1/4, -x+1/4, -z+1/4'
    '-y+1/4, x+1/4, -z+1/4'
_cell_length_a     14.1096(6)
_cell_length_b     14.1096(6)
_cell_length_c     24.6537(11)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     4908.1(4)
_cell_formula_units_Z     16
_cell_measurement_reflns_used     9075
_cell_measurement_theta_min     2.6
_cell_measurement_theta_max     27.3
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.28
_exptl_crystal_size_mid     0.24
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.333
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     2080
_exptl_absorpt_coefficient_mu     0.096
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2004)
;
_exptl_absorpt_correction_T_min     0.9736
_exptl_absorpt_correction_T_max     0.9810
_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 Kappa APEXII CCD'
_diffrn_measurement_method     'ω and φ scan'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     33461
_diffrn_reflns_av_R_equivalents     0.0406
_diffrn_reflns_av_sigmaI/netI     0.0217
_diffrn_reflns_theta_min     2.63
_diffrn_reflns_theta_max     27.09
_diffrn_reflns_theta_full     27.09
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     18
_diffrn_reflns_limit_k_min     -18
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -31
_diffrn_reflns_limit_l_max     31
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     0
_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     2705
_reflns_number_gt     1564
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1063
_refine_ls_R_factor_gt     0.0546
_refine_ls_wR_factor_gt     0.1401
_refine_ls_wR_factor_ref     0.1910
_refine_ls_goodness_of_fit_ref     1.052
_refine_ls_restrained_S_all     1.052
_refine_ls_number_reflns     2705
_refine_ls_number_parameters     169
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0790P)²+4.2162P] 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     0.169
_refine_diff_density_min     -0.177
_refine_ls_extinction_method
;
SHELXL97 (Sheldrick, 2008)
;
_refine_ls_extinction_coef     0.0018(4)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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, 2004)
;
_computing_cell_refinement
;
SAINT (Bruker, 2004)
;
_computing_data_reduction
;
SAINT (Bruker, 2004)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_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 C1 0.3466(2) 0.3614(2) 0.53227(11) 0.0800(9) Uani d . 1 1 . .
    H H1 0.3287 0.3597 0.5686 0.096 Uiso calc R 1 1 . .
    C C2 0.4403(2) 0.3718(3) 0.51924(13) 0.1165(15) Uani d . 1 1 . .
    H H2 0.4854 0.3779 0.5465 0.140 Uiso calc R 1 1 . .
    C C3 0.4674(2) 0.3733(3) 0.46571(13) 0.1088(13) Uani d . 1 1 . .
    H H3 0.5311 0.3798 0.4568 0.131 Uiso calc R 1 1 . .
    C C4 0.4020(2) 0.3655(2) 0.42581(12) 0.0780(8) Uani d . 1 1 . .
    H H4 0.4210 0.3666 0.3897 0.094 Uiso calc R 1 1 . .
    C C5 0.30732(18) 0.35571(17) 0.43851(9) 0.0585(6) Uani d . 1 1 . .
    C C6 0.27839(17) 0.35353(16) 0.49277(9) 0.0544(6) Uani d . 1 1 . .
    C C7 0.17649(18) 0.34951(17) 0.50774(10) 0.0599(6) Uani d . 1 1 . .
    C C8 0.13374(19) 0.61715(17) 0.54553(10) 0.0614(6) Uani d . 1 1 . .
    C C9 0.2265(2) 0.6006(2) 0.53459(12) 0.0730(7) Uani d . 1 1 . .
    H H9 0.2712 0.6010 0.5623 0.088 Uiso calc R 1 1 . .
    C C10 0.2540(2) 0.5829(2) 0.48125(12) 0.0745(8) Uani d . 1 1 . .
    H H10 0.3176 0.5717 0.4736 0.089 Uiso calc R 1 1 . .
    C C11 0.19078(19) 0.58161(18) 0.44066(11) 0.0670(7) Uani d . 1 1 . .
    H H11 0.2104 0.5699 0.4053 0.080 Uiso calc R 1 1 . .
    C C12 0.09491(17) 0.59811(17) 0.45197(10) 0.0576(6) Uani d . 1 1 . .
    C C13 0.0943(2) 0.6378(2) 0.59994(11) 0.0778(8) Uani d . 1 1 . .
    H H13A 0.1448 0.6403 0.6260 0.117 Uiso calc R 1 1 . .
    H H13B 0.0504 0.5888 0.6099 0.117 Uiso calc R 1 1 . .
    H H13C 0.0620 0.6977 0.5992 0.117 Uiso calc R 1 1 . .
    N N1 0.07022(14) 0.61524(13) 0.50402(7) 0.0560(5) Uani d . 1 1 . .
    H H1B 0.0115 0.6254 0.5113 0.067 Uiso calc R 1 1 . .
    N N2 0.02771(16) 0.59673(17) 0.41480(8) 0.0744(7) Uani d . 1 1 . .
    H H2A -0.0303 0.6066 0.4239 0.089 Uiso calc R 1 1 . .
    H H2B 0.0419 0.5860 0.3814 0.089 Uiso calc R 1 1 . .
    O O1 0.24464(16) 0.35081(17) 0.39747(7) 0.0842(6) Uani d D 1 1 . .
    O O2 0.11578(12) 0.35100(14) 0.46963(7) 0.0710(5) Uani d . 1 1 . .
    O O3 0.15438(14) 0.34665(16) 0.55672(7) 0.0848(6) Uani d . 1 1 . .
    H H1A 0.1912(12) 0.351(3) 0.4121(13) 0.103(12) Uiso d D 1 1 . .
_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
    C1 C2 . 1.368(4) ?
    C1 C6 . 1.374(3) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.374(4) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.353(4) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.379(4) ?
    C4 H4 . 0.9300 ?
    C5 O1 . 1.346(3) ?
    C5 C6 . 1.399(3) ?
    C6 C7 . 1.485(3) ?
    C7 O3 . 1.248(3) ?
    C7 O2 . 1.272(3) ?
    C8 C9 . 1.357(4) ?
    C8 N1 . 1.361(3) ?
    C8 C13 . 1.481(4) ?
    C9 C10 . 1.394(4) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.341(4) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.401(4) ?
    C11 H11 . 0.9300 ?
    C12 N2 . 1.319(3) ?
    C12 N1 . 1.351(3) ?
    C13 H13A . 0.9600 ?
    C13 H13B . 0.9600 ?
    C13 H13C . 0.9600 ?
    N1 H1B . 0.8600 ?
    N2 H2A . 0.8600 ?
    N2 H2B . 0.8600 ?
    O1 H1A . 0.835(10) ?
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
    C2 C1 C6 . . 121.3(3) ?
    C2 C1 H1 . . 119.4 ?
    C6 C1 H1 . . 119.4 ?
    C1 C2 C3 . . 119.7(3) ?
    C1 C2 H2 . . 120.1 ?
    C3 C2 H2 . . 120.1 ?
    C4 C3 C2 . . 120.5(3) ?
    C4 C3 H3 . . 119.8 ?
    C2 C3 H3 . . 119.7 ?
    C3 C4 C5 . . 120.2(3) ?
    C3 C4 H4 . . 119.9 ?
    C5 C4 H4 . . 119.9 ?
    O1 C5 C4 . . 118.1(2) ?
    O1 C5 C6 . . 121.7(2) ?
    C4 C5 C6 . . 120.1(2) ?
    C1 C6 C5 . . 118.1(2) ?
    C1 C6 C7 . . 120.3(2) ?
    C5 C6 C7 . . 121.4(2) ?
    O3 C7 O2 . . 123.2(2) ?
    O3 C7 C6 . . 118.9(2) ?
    O2 C7 C6 . . 117.9(2) ?
    C9 C8 N1 . . 118.8(2) ?
    C9 C8 C13 . . 125.2(3) ?
    N1 C8 C13 . . 115.9(2) ?
    C8 C9 C10 . . 119.1(3) ?
    C8 C9 H9 . . 120.4 ?
    C10 C9 H9 . . 120.4 ?
    C11 C10 C9 . . 121.4(3) ?
    C11 C10 H10 . . 119.3 ?
    C9 C10 H10 . . 119.3 ?
    C10 C11 C12 . . 119.4(3) ?
    C10 C11 H11 . . 120.3 ?
    C12 C11 H11 . . 120.3 ?
    N2 C12 N1 . . 118.5(2) ?
    N2 C12 C11 . . 123.6(2) ?
    N1 C12 C11 . . 117.9(2) ?
    C8 C13 H13A . . 109.5 ?
    C8 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    C8 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
    C12 N1 C8 . . 123.2(2) ?
    C12 N1 H1B . . 118.4 ?
    C8 N1 H1B . . 118.4 ?
    C12 N2 H2A . . 120.0 ?
    C12 N2 H2B . . 120.0 ?
    H2A N2 H2B . . 120.0 ?
    C5 O1 H1A . . 106(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
    C6 C1 C2 C3 . . . . -0.8(6) ?
    C1 C2 C3 C4 . . . . 0.6(7) ?
    C2 C3 C4 C5 . . . . -0.1(6) ?
    C3 C4 C5 O1 . . . . 178.2(3) ?
    C3 C4 C5 C6 . . . . -0.2(4) ?
    C2 C1 C6 C5 . . . . 0.4(5) ?
    C2 C1 C6 C7 . . . . -175.4(3) ?
    O1 C5 C6 C1 . . . . -178.3(3) ?
    C4 C5 C6 C1 . . . . 0.1(4) ?
    O1 C5 C6 C7 . . . . -2.4(4) ?
    C4 C5 C6 C7 . . . . 175.9(2) ?
    C1 C6 C7 O3 . . . . -5.0(4) ?
    C5 C6 C7 O3 . . . . 179.2(2) ?
    C1 C6 C7 O2 . . . . 173.6(3) ?
    C5 C6 C7 O2 . . . . -2.1(3) ?
    N1 C8 C9 C10 . . . . 0.5(4) ?
    C13 C8 C9 C10 . . . . -179.4(3) ?
    C8 C9 C10 C11 . . . . -0.2(4) ?
    C9 C10 C11 C12 . . . . -0.2(4) ?
    C10 C11 C12 N2 . . . . -178.9(3) ?
    C10 C11 C12 N1 . . . . 0.3(4) ?
    N2 C12 N1 C8 . . . . 179.2(2) ?
    C11 C12 N1 C8 . . . . 0.0(3) ?
    C9 C8 N1 C12 . . . . -0.4(4) ?
    C13 C8 N1 C12 . . . . 179.5(2) ?
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
    O1 H1A O2 . 0.835(10) 1.774(18) 2.544(3) 152(3) y
    N1 H1B O2 9_566 0.86 1.89 2.745(3) 177 y
    N2 H2A O3 9_566 0.86 1.93 2.781(3) 169 y
    N2 H2B O3 8_454 0.86 2.00 2.836(3) 163 y
data_global
_journal_date_recd_electronic     2016-04-26
_journal_date_accepted     2016-05-04
_journal_name_full     'IUCrData'
_journal_year     2016
_journal_volume     1
_journal_issue      5
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2414314616007471
_journal_coeditor_code     BT4008
_publ_contact_author_name     'G. Chakkaravarthi'
_publ_contact_author_address
;
Department of Physics
CPCL Polytechnic College
Chennai 600 068
India
;
_publ_contact_author_email
                        'chakkaravarthi_2005@yahoo.com, israel.samuel@gmail.com'
_publ_contact_author_fax     ?
_publ_contact_author_phone     '08608587478'
_publ_section_title
;
2-Amino-6-methylpyridinium 2-hydroxybenzoate
;
loop_
    _publ_author_name
    _publ_author_address
    'P. Sivakumar'
;
Research and Development Centre,
Bharathiar University
Coimbatore 641 046
India
Department of Physics,
CPCL Polytechnic College,
Chennai 600 068,
India
;
    'S. Sudhahar'
;
Department of Physics,
Alagappa University,
Karaikkudi 630 003,
India
;
    'S. Israel'
;
Department of Physics,
The American College,
Madurai 625 002
India
;
    'G. Chakkaravarthi'
;
Department of Physics,
CPCL Polytechnic College,
Chennai 600 068,
India
;
_publ_section_synopsis
;
In the title molecular salt, the pyridine ring of the cation is protonated at
its N atom and the anion is deprotonated at an O atom. In the crystal, the
ions are linked via three N---H...O hydrogen bonds into tetramers.
;
