##############################################################################
#                                                                            #
# 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.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2012-12-04
_journal_date_accepted     2012-12-11
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2013
_journal_volume     69
_journal_issue      1
_journal_page_first     o94
_journal_page_last     o95
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536812050374
_journal_coeditor_code     IS5229
_publ_contact_author_name     'Ibrahim Abdul Razak'
_publ_contact_author_address
;
School of Physics
Universiti Sains Malaysia
11800 USM, Penang
Malaysia
;
_publ_contact_author_email     'arazaki@usm.my'
_publ_contact_author_fax     '604 6579150'
_publ_contact_author_phone     '604 6535306'
_publ_section_title
;
2-Amino-5-methylpyridinium 4-methylbenzoate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Kaliyaperumal Thanigaimani' ?
;
School of Physics
Universiti Sains Malaysia
11800 USM, Penang
Malaysia
;
    'Abbas Farhadikoutenaei' ?
;
School of Physics
Universiti Sains Malaysia
11800 USM, Penang
Malaysia
Department of Physics
Faculty of Science
University of Mazandaran
Babolsar
Iran
;
    'Suhana Arshad' ?
;
School of Physics
Universiti Sains Malaysia
11800 USM, Penang
Malaysia
;
    'Ibrahim Abdul Razak'
;
Thomson Reuters ResearcherID: A-5599-2009.
;
;
School of Physics
Universiti Sains Malaysia
11800 USM, Penang
Malaysia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2-Amino-5-methylpyridinium 4-methylbenzoate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C6 H9 N2 +, C8 H7 O2 -'
_chemical_formula_sum     'C14 H16 N2 O2'
_chemical_formula_iupac     'C6 H9 N2 +, C8 H7 O2 -'
_chemical_formula_weight     244.29
_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     9.6315(5)
_cell_length_b     10.8713(6)
_cell_length_c     12.1481(7)
_cell_angle_alpha     90.00
_cell_angle_beta     104.0930(10)
_cell_angle_gamma     90.00
_cell_volume     1233.71(12)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     6272
_cell_measurement_theta_min     2.55
_cell_measurement_theta_max     32.56
_cell_measurement_temperature     100.0(10)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.52
_exptl_crystal_size_mid     0.32
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     1.315
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     520
_exptl_absorpt_coefficient_mu     0.089
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2009)'
_exptl_absorpt_correction_T_min     0.9552
_exptl_absorpt_correction_T_max     0.9868
_exptl_special_details
;
The crystal was placed in the cold stream of an Oxford Cryosystems Cobra
open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
;
_diffrn_ambient_temperature     100.0(10)
_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 area-detector
;
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     18139
_diffrn_reflns_av_R_equivalents     0.0274
_diffrn_reflns_av_sigmaI/netI     0.0239
_diffrn_reflns_theta_min     2.55
_diffrn_reflns_theta_max     32.65
_diffrn_reflns_theta_full     32.65
_diffrn_measured_fraction_theta_max     0.993
_diffrn_measured_fraction_theta_full     0.993
_diffrn_reflns_limit_h_min     -14
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_k_max     16
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     0
_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 >
σ(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     4493
_reflns_number_gt     3783
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0527
_refine_ls_R_factor_gt     0.0433
_refine_ls_wR_factor_gt     0.1175
_refine_ls_wR_factor_ref     0.1248
_refine_ls_goodness_of_fit_ref     1.034
_refine_ls_restrained_S_all     1.034
_refine_ls_number_reflns     4493
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0678P)²+0.3153P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.431
_refine_diff_density_min     -0.292
_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, 2009)'
_computing_cell_refinement     'SAINT (Bruker, 2009)'
_computing_data_reduction     'SAINT (Bruker, 2009)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (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
    O O1 0.07967(7) 1.13827(6) 0.07082(5) 0.01774(14) Uani d . 1 1 . .
    O O2 0.20480(8) 1.12140(6) -0.06122(6) 0.01914(15) Uani d . 1 1 . .
    C C1 0.23323(9) 0.93283(8) 0.19086(7) 0.01486(16) Uani d . 1 1 . .
    H H1A 0.1613 0.9680 0.2224 0.018 Uiso calc R 1 1 . .
    C C2 0.31890(10) 0.83760(8) 0.24780(7) 0.01618(16) Uani d . 1 1 . .
    H H2A 0.3048 0.8090 0.3182 0.019 Uiso calc R 1 1 . .
    C C3 0.42490(9) 0.78366(8) 0.20317(7) 0.01589(16) Uani d . 1 1 . .
    C C4 0.44248(10) 0.82614(9) 0.09878(8) 0.01896(18) Uani d . 1 1 . .
    H H4A 0.5132 0.7900 0.0665 0.023 Uiso calc R 1 1 . .
    C C5 0.35734(10) 0.92094(9) 0.04167(7) 0.01693(17) Uani d . 1 1 . .
    H H5A 0.3702 0.9484 -0.0294 0.020 Uiso calc R 1 1 . .
    C C6 0.25310(9) 0.97626(8) 0.08768(7) 0.01277(15) Uani d . 1 1 . .
    C C7 0.17236(9) 1.08592(8) 0.02773(7) 0.01374(15) Uani d . 1 1 . .
    C C8 0.51917(10) 0.68238(9) 0.26587(8) 0.02109(19) Uani d . 1 1 . .
    H H8A 0.5215 0.6869 0.3469 0.032 Uiso calc R 1 1 . .
    H H8B 0.6164 0.6921 0.2556 0.032 Uiso calc R 1 1 . .
    H H8C 0.4808 0.6024 0.2358 0.032 Uiso calc R 1 1 . .
    N N1 0.94348(8) 0.32387(7) 0.93651(6) 0.01462(15) Uani d . 1 1 . .
    N N2 1.04273(9) 0.28128(8) 0.78450(7) 0.01928(16) Uani d . 1 1 . .
    C C9 0.95687(9) 0.35009(8) 0.83058(7) 0.01471(16) Uani d . 1 1 . .
    C C10 0.87654(10) 0.45002(9) 0.77234(7) 0.01714(17) Uani d . 1 1 . .
    H H10A 0.8825 0.4703 0.6976 0.021 Uiso calc R 1 1 . .
    C C11 0.79056(10) 0.51697(8) 0.82424(8) 0.01771(17) Uani d . 1 1 . .
    H H11A 0.7373 0.5839 0.7847 0.021 Uiso calc R 1 1 . .
    C C12 0.77883(9) 0.48901(8) 0.93576(8) 0.01643(16) Uani d . 1 1 . .
    C C13 0.85738(9) 0.39091(8) 0.98802(7) 0.01558(16) Uani d . 1 1 . .
    H H13A 0.8517 0.3689 1.0625 0.019 Uiso calc R 1 1 . .
    C C14 0.68490(11) 0.56433(9) 0.99240(9) 0.02191(19) Uani d . 1 1 . .
    H H14A 0.6859 0.5287 1.0667 0.033 Uiso calc R 1 1 . .
    H H14B 0.5867 0.5644 0.9450 0.033 Uiso calc R 1 1 . .
    H H14C 0.7209 0.6489 1.0024 0.033 Uiso calc R 1 1 . .
    H H1N2 1.0977(16) 0.2237(15) 0.8310(13) 0.035(4) Uiso d . 1 1 . .
    H H2N2 1.0599(17) 0.3085(15) 0.7168(14) 0.035(4) Uiso d . 1 1 . .
    H H1N1 0.9942(18) 0.2547(17) 0.9795(15) 0.046(5) Uiso d . 1 1 . .
_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
    O1 C7 . 1.2737(10) ?
    O2 C7 . 1.2564(11) ?
    C1 C6 . 1.3956(12) ?
    C1 C2 . 1.3975(12) ?
    C1 H1A . 0.9500 ?
    C2 C3 . 1.3962(13) ?
    C2 H2A . 0.9500 ?
    C3 C4 . 1.3981(13) ?
    C3 C8 . 1.5100(12) ?
    C4 C5 . 1.3924(12) ?
    C4 H4A . 0.9500 ?
    C5 C6 . 1.3984(12) ?
    C5 H5A . 0.9500 ?
    C6 C7 . 1.5101(12) ?
    C8 H8A . 0.9800 ?
    C8 H8B . 0.9800 ?
    C8 H8C . 0.9800 ?
    N1 C9 . 1.3545(11) ?
    N1 C13 . 1.3649(11) ?
    N1 H1N1 . 0.976(18) ?
    N2 C9 . 1.3351(12) ?
    N2 H1N2 . 0.920(16) ?
    N2 H2N2 . 0.926(16) ?
    C9 C10 . 1.4187(12) ?
    C10 C11 . 1.3665(13) ?
    C10 H10A . 0.9500 ?
    C11 C12 . 1.4195(13) ?
    C11 H11A . 0.9500 ?
    C12 C13 . 1.3708(12) ?
    C12 C14 . 1.5052(13) ?
    C13 H13A . 0.9500 ?
    C14 H14A . 0.9800 ?
    C14 H14B . 0.9800 ?
    C14 H14C . 0.9800 ?
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
    C6 C1 C2 . . 120.10(8) ?
    C6 C1 H1A . . 120.0 ?
    C2 C1 H1A . . 120.0 ?
    C3 C2 C1 . . 121.23(8) ?
    C3 C2 H2A . . 119.4 ?
    C1 C2 H2A . . 119.4 ?
    C2 C3 C4 . . 118.36(8) ?
    C2 C3 C8 . . 121.14(8) ?
    C4 C3 C8 . . 120.51(8) ?
    C5 C4 C3 . . 120.64(8) ?
    C5 C4 H4A . . 119.7 ?
    C3 C4 H4A . . 119.7 ?
    C4 C5 C6 . . 120.81(8) ?
    C4 C5 H5A . . 119.6 ?
    C6 C5 H5A . . 119.6 ?
    C1 C6 C5 . . 118.84(8) ?
    C1 C6 C7 . . 122.21(7) ?
    C5 C6 C7 . . 118.84(7) ?
    O2 C7 O1 . . 124.21(8) ?
    O2 C7 C6 . . 116.77(8) ?
    O1 C7 C6 . . 118.99(7) ?
    C3 C8 H8A . . 109.5 ?
    C3 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    C3 C8 H8C . . 109.5 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
    C9 N1 C13 . . 122.15(8) ?
    C9 N1 H1N1 . . 121.3(10) ?
    C13 N1 H1N1 . . 116.6(10) ?
    C9 N2 H1N2 . . 116.5(10) ?
    C9 N2 H2N2 . . 117.1(10) ?
    H1N2 N2 H2N2 . . 124.3(14) ?
    N2 C9 N1 . . 119.50(8) ?
    N2 C9 C10 . . 122.56(8) ?
    N1 C9 C10 . . 117.94(8) ?
    C11 C10 C9 . . 119.73(8) ?
    C11 C10 H10A . . 120.1 ?
    C9 C10 H10A . . 120.1 ?
    C10 C11 C12 . . 121.62(8) ?
    C10 C11 H11A . . 119.2 ?
    C12 C11 H11A . . 119.2 ?
    C13 C12 C11 . . 116.45(8) ?
    C13 C12 C14 . . 122.48(8) ?
    C11 C12 C14 . . 121.08(8) ?
    N1 C13 C12 . . 122.11(8) ?
    N1 C13 H13A . . 118.9 ?
    C12 C13 H13A . . 118.9 ?
    C12 C14 H14A . . 109.5 ?
    C12 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    C12 C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
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 . . . . -0.32(13) ?
    C1 C2 C3 C4 . . . . -0.82(13) ?
    C1 C2 C3 C8 . . . . 178.86(8) ?
    C2 C3 C4 C5 . . . . 0.77(14) ?
    C8 C3 C4 C5 . . . . -178.91(9) ?
    C3 C4 C5 C6 . . . . 0.41(14) ?
    C2 C1 C6 C5 . . . . 1.49(13) ?
    C2 C1 C6 C7 . . . . -174.64(8) ?
    C4 C5 C6 C1 . . . . -1.54(13) ?
    C4 C5 C6 C7 . . . . 174.72(8) ?
    C1 C6 C7 O2 . . . . 175.94(8) ?
    C5 C6 C7 O2 . . . . -0.19(12) ?
    C1 C6 C7 O1 . . . . -2.27(12) ?
    C5 C6 C7 O1 . . . . -178.40(8) ?
    C13 N1 C9 N2 . . . . 179.99(8) ?
    C13 N1 C9 C10 . . . . -0.73(13) ?
    N2 C9 C10 C11 . . . . -179.98(9) ?
    N1 C9 C10 C11 . . . . 0.77(13) ?
    C9 C10 C11 C12 . . . . -0.17(14) ?
    C10 C11 C12 C13 . . . . -0.48(13) ?
    C10 C11 C12 C14 . . . . 179.36(9) ?
    C9 N1 C13 C12 . . . . 0.07(13) ?
    C11 C12 C13 N1 . . . . 0.54(13) ?
    C14 C12 C13 N1 . . . . -179.30(8) ?
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
    N2 H1N2 O2 1_646 0.920(16) 1.832(16) 2.7469(11) 172.7(15) yes
    N2 H2N2 O1 4_676 0.926(16) 1.919(17) 2.8424(11) 175.4(15) yes
    N1 H1N1 O1 1_646 0.976(18) 1.751(18) 2.7224(10) 173.1(16) yes
    C10 H10A O2 2_645 0.95 2.34 3.1120(11) 138 yes
