##############################################################################
#                                                                            #
# 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     SHELXL-97
_journal_date_recd_electronic     2012-06-25
_journal_date_accepted     2012-07-10
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue      8
_journal_page_first     o2474
_journal_page_last     o2474
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536812031352
_journal_coeditor_code     XU5582
_publ_contact_author
;
     Dr. Seik Weng Ng
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
_publ_contact_author_email     seikweng@um.edu.my
_publ_contact_author_fax     '03 7967 4193'
_publ_contact_author_phone     '03 7967 6778'
_publ_section_title
;
4-[(2-Hydroxybenzyl)amino]pyridinium nitrate
;
loop_
    _publ_author_name
    _publ_author_address
    'Gao, Shan'
;
Key Laboratory of Functional Inorganic Materials Chemistry
Ministry of Education
Heilongjiang University
Harbin 150080
People's Republic of China
;
    'Ng, Seik Weng'
;
Department of Chemistry
University of Malaya
50603 Kuala Lumpur
Malaysia
Chemistry Department
Faculty of Science
King Abdulaziz University
PO Box 80203, Jeddah
Saudi Arabia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
4-[(2-Hydroxybenzyl)amino]pyridinium nitrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H13 N2 O +, N O3 -'
_chemical_formula_sum     'C12 H13 N3 O4'
_chemical_formula_iupac     'C12 H13 N2 O +, N O3 -'
_chemical_formula_weight     263.25
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'C c'
_symmetry_space_group_name_Hall     'C -2yc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    'x, -y, z+1/2'
    'x+1/2, y+1/2, z'
    'x+1/2, -y+1/2, z+1/2'
_cell_length_a     13.611(4)
_cell_length_b     12.687(3)
_cell_length_c     10.030(2)
_cell_angle_alpha     90.00
_cell_angle_beta     132.694(12)
_cell_angle_gamma     90.00
_cell_volume     1273.0(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min     ?
_cell_measurement_theta_max     ?
_cell_measurement_temperature     295(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     'faint yellow'
_exptl_crystal_size_max     0.24
_exptl_crystal_size_mid     0.21
_exptl_crystal_size_min     0.21
_exptl_crystal_density_diffrn     1.374
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     552
_exptl_absorpt_coefficient_mu     0.105
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(ABSCOR; Higashi, 1995)'
_exptl_absorpt_correction_T_min     0.9752
_exptl_absorpt_correction_T_max     0.9782
_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     'Rigaku R-AXIS RAPID IP'
_diffrn_measurement_method     'ω scan'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6077
_diffrn_reflns_av_R_equivalents     0.0411
_diffrn_reflns_av_sigmaI/netI     0.0309
_diffrn_reflns_theta_min     3.21
_diffrn_reflns_theta_max     27.48
_diffrn_reflns_theta_full     27.48
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_k_max     16
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     1458
_reflns_number_gt     1176
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0501
_refine_ls_R_factor_gt     0.0426
_refine_ls_wR_factor_gt     0.1047
_refine_ls_wR_factor_ref     0.1161
_refine_ls_goodness_of_fit_ref     1.082
_refine_ls_restrained_S_all     1.080
_refine_ls_number_reflns     1458
_refine_ls_number_parameters     184
_refine_ls_number_restraints     5
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0753P)²] 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     0.001
_refine_diff_density_max     0.201
_refine_diff_density_min     -0.166
_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 0.0000
                         '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 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'RAPID-AUTO (Rigaku, 1998)'
_computing_cell_refinement     'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction     'CrystalClear (Rigaku/MSC, 2002)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'X-SEED (Barbour, 2001)'
_computing_publication_material     'publCIF (Westrip, 2010)'
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 0.5006(2) 0.17761(17) 0.5005(3) 0.0795(6) Uani d D 1 1 . .
    O O2 0.4295(3) 0.38568(15) 0.3747(3) 0.0882(7) Uani d . 1 1 . .
    O O3 0.3096(2) 0.47126(17) 0.1249(3) 0.0817(6) Uani d . 1 1 . .
    O O4 0.3075(2) 0.30247(17) 0.1215(3) 0.0816(6) Uani d . 1 1 . .
    N N1 0.4372(3) -0.37774(19) 0.4116(4) 0.0740(6) Uani d D 1 1 . .
    N N2 0.6073(2) -0.11750(18) 0.7349(3) 0.0692(6) Uani d D 1 1 . .
    N N3 0.3475(2) 0.38556(18) 0.2053(3) 0.0669(6) Uani d . 1 1 . .
    C C1 0.4016(3) -0.2829(3) 0.3359(4) 0.0739(7) Uani d . 1 1 . .
    H H1A 0.3378 -0.2776 0.2101 0.089 Uiso calc R 1 1 . .
    C C2 0.4552(3) -0.1938(2) 0.4358(4) 0.0660(6) Uani d . 1 1 . .
    H H2A 0.4293 -0.1284 0.3792 0.079 Uiso calc R 1 1 . .
    C C3 0.5510(2) -0.2009(2) 0.6271(4) 0.0588(6) Uani d . 1 1 . .
    C C4 0.5857(3) -0.3036(2) 0.7024(4) 0.0641(6) Uani d . 1 1 . .
    H H4 0.6484 -0.3128 0.8276 0.077 Uiso calc R 1 1 . .
    C C5 0.5270(3) -0.3885(2) 0.5910(4) 0.0720(7) Uani d . 1 1 . .
    H H5 0.5501 -0.4557 0.6411 0.086 Uiso calc R 1 1 . .
    C C6 0.5830(3) -0.0101(2) 0.6719(4) 0.0708(7) Uani d . 1 1 . .
    H H6A 0.5908 -0.0060 0.5828 0.085 Uiso calc R 1 1 . .
    H H6B 0.6522 0.0343 0.7734 0.085 Uiso calc R 1 1 . .
    C C7 0.4489(2) 0.03351(19) 0.5886(3) 0.0569(5) Uani d . 1 1 . .
    C C8 0.3625(3) -0.0166(2) 0.5960(4) 0.0650(6) Uani d . 1 1 . .
    H H8 0.3879 -0.0800 0.6584 0.078 Uiso calc R 1 1 . .
    C C9 0.2390(3) 0.0260(3) 0.5123(5) 0.0784(8) Uani d . 1 1 . .
    H H9 0.1825 -0.0078 0.5201 0.094 Uiso calc R 1 1 . .
    C C10 0.2006(3) 0.1180(3) 0.4180(6) 0.0834(9) Uani d . 1 1 . .
    H H10 0.1164 0.1456 0.3584 0.100 Uiso calc R 1 1 . .
    C C11 0.2847(3) 0.1707(2) 0.4096(4) 0.0742(7) Uani d . 1 1 . .
    H H11 0.2578 0.2336 0.3456 0.089 Uiso calc R 1 1 . .
    C C12 0.4100(3) 0.12908(19) 0.4978(3) 0.0607(6) Uani d . 1 1 . .
    H H1 0.477(4) 0.2368(14) 0.450(4) 0.082(9) Uiso d D 1 1 . .
    H H2 0.670(3) -0.126(3) 0.8524(16) 0.081(10) Uiso d D 1 1 . .
    H H3 0.400(3) -0.4320(18) 0.337(4) 0.081(10) Uiso d D 1 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
    O1 0.0804(12) 0.0576(10) 0.1069(16) 0.0045(9) 0.0660(12) 0.0162(10)
    O2 0.1108(18) 0.0634(12) 0.0670(14) -0.0060(11) 0.0509(14) -0.0011(9)
    O3 0.0915(14) 0.0660(12) 0.0782(13) 0.0112(10) 0.0539(12) 0.0097(10)
    O4 0.0855(13) 0.0665(12) 0.0805(13) -0.0092(10) 0.0514(12) -0.0138(9)
    N1 0.0745(14) 0.0683(15) 0.0895(17) -0.0068(12) 0.0597(14) -0.0155(13)
    N2 0.0629(13) 0.0570(13) 0.0657(14) 0.0038(9) 0.0349(12) 0.0069(10)
    N3 0.0683(12) 0.0654(15) 0.0713(14) 0.0001(10) 0.0490(12) -0.0010(10)
    C1 0.0661(15) 0.0879(19) 0.0658(15) 0.0049(14) 0.0440(13) -0.0032(14)
    C2 0.0633(14) 0.0672(15) 0.0679(15) 0.0097(12) 0.0446(13) 0.0088(12)
    C3 0.0562(12) 0.0546(13) 0.0682(15) 0.0055(10) 0.0432(13) 0.0058(10)
    C4 0.0664(15) 0.0564(14) 0.0701(15) 0.0080(11) 0.0465(13) 0.0094(11)
    C5 0.0798(17) 0.0559(15) 0.095(2) 0.0059(12) 0.0648(17) 0.0061(13)
    C6 0.0637(13) 0.0531(14) 0.0834(17) -0.0003(11) 0.0450(13) 0.0036(12)
    C7 0.0619(13) 0.0460(11) 0.0593(12) -0.0046(9) 0.0397(11) -0.0073(9)
    C8 0.0780(15) 0.0521(12) 0.0761(15) -0.0087(12) 0.0566(13) -0.0094(11)
    C9 0.0841(18) 0.0707(18) 0.108(2) -0.0118(14) 0.0759(19) -0.0190(16)
    C10 0.0751(17) 0.075(2) 0.112(2) 0.0063(14) 0.0680(19) -0.0095(17)
    C11 0.0767(16) 0.0611(15) 0.0868(19) 0.0102(12) 0.0562(16) 0.0047(12)
    C12 0.0665(13) 0.0504(13) 0.0675(14) -0.0021(11) 0.0463(12) -0.0055(10)
_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 C12 . 1.362(3) ?
    O1 H1 . 0.837(10) ?
    O2 N3 . 1.250(3) ?
    O3 N3 . 1.238(3) ?
    O4 N3 . 1.222(3) ?
    N1 C1 . 1.327(4) ?
    N1 C5 . 1.330(4) ?
    N1 H3 . 0.882(10) ?
    N2 C3 . 1.324(4) ?
    N2 C6 . 1.443(3) ?
    N2 H2 . 0.874(10) ?
    C1 C2 . 1.350(4) ?
    C1 H1A . 0.9300 ?
    C2 C3 . 1.413(4) ?
    C2 H2A . 0.9300 ?
    C3 C4 . 1.418(3) ?
    C4 C5 . 1.354(4) ?
    C4 H4 . 0.9300 ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.505(4) ?
    C6 H6A . 0.9700 ?
    C6 H6B . 0.9700 ?
    C7 C8 . 1.383(4) ?
    C7 C12 . 1.388(3) ?
    C8 C9 . 1.381(4) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.364(5) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.376(5) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.387(4) ?
    C11 H11 . 0.9300 ?
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
    C12 O1 H1 . . 115(3) ?
    C1 N1 C5 . . 120.7(3) ?
    C1 N1 H3 . . 116(2) ?
    C5 N1 H3 . . 123(2) ?
    C3 N2 C6 . . 124.3(2) ?
    C3 N2 H2 . . 120(2) ?
    C6 N2 H2 . . 116(2) ?
    O4 N3 O3 . . 121.0(2) ?
    O4 N3 O2 . . 120.5(2) ?
    O3 N3 O2 . . 118.5(2) ?
    N1 C1 C2 . . 122.0(3) ?
    N1 C1 H1A . . 119.0 ?
    C2 C1 H1A . . 119.0 ?
    C1 C2 C3 . . 119.5(3) ?
    C1 C2 H2A . . 120.3 ?
    C3 C2 H2A . . 120.3 ?
    N2 C3 C2 . . 123.3(2) ?
    N2 C3 C4 . . 120.1(2) ?
    C2 C3 C4 . . 116.7(2) ?
    C5 C4 C3 . . 119.6(3) ?
    C5 C4 H4 . . 120.2 ?
    C3 C4 H4 . . 120.2 ?
    N1 C5 C4 . . 121.5(3) ?
    N1 C5 H5 . . 119.3 ?
    C4 C5 H5 . . 119.3 ?
    N2 C6 C7 . . 115.0(2) ?
    N2 C6 H6A . . 108.5 ?
    C7 C6 H6A . . 108.5 ?
    N2 C6 H6B . . 108.5 ?
    C7 C6 H6B . . 108.5 ?
    H6A C6 H6B . . 107.5 ?
    C8 C7 C12 . . 118.5(2) ?
    C8 C7 C6 . . 123.8(2) ?
    C12 C7 C6 . . 117.7(2) ?
    C9 C8 C7 . . 121.1(3) ?
    C9 C8 H8 . . 119.5 ?
    C7 C8 H8 . . 119.5 ?
    C10 C9 C8 . . 119.5(3) ?
    C10 C9 H9 . . 120.2 ?
    C8 C9 H9 . . 120.2 ?
    C9 C10 C11 . . 121.0(3) ?
    C9 C10 H10 . . 119.5 ?
    C11 C10 H10 . . 119.5 ?
    C10 C11 C12 . . 119.3(3) ?
    C10 C11 H11 . . 120.3 ?
    C12 C11 H11 . . 120.3 ?
    O1 C12 C11 . . 123.0(2) ?
    O1 C12 C7 . . 116.4(2) ?
    C11 C12 C7 . . 120.6(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
    C5 N1 C1 C2 . . . . 0.8(4) ?
    N1 C1 C2 C3 . . . . -0.8(4) ?
    C6 N2 C3 C2 . . . . -2.9(4) ?
    C6 N2 C3 C4 . . . . 177.4(2) ?
    C1 C2 C3 N2 . . . . -179.3(3) ?
    C1 C2 C3 C4 . . . . 0.5(3) ?
    N2 C3 C4 C5 . . . . 179.6(3) ?
    C2 C3 C4 C5 . . . . -0.1(3) ?
    C1 N1 C5 C4 . . . . -0.4(4) ?
    C3 C4 C5 N1 . . . . 0.1(4) ?
    C3 N2 C6 C7 . . . . 73.7(4) ?
    N2 C6 C7 C8 . . . . 10.2(4) ?
    N2 C6 C7 C12 . . . . -169.2(2) ?
    C12 C7 C8 C9 . . . . 1.3(4) ?
    C6 C7 C8 C9 . . . . -178.1(3) ?
    C7 C8 C9 C10 . . . . 1.2(4) ?
    C8 C9 C10 C11 . . . . -2.0(5) ?
    C9 C10 C11 C12 . . . . 0.3(5) ?
    C10 C11 C12 O1 . . . . -178.2(3) ?
    C10 C11 C12 C7 . . . . 2.1(4) ?
    C8 C7 C12 O1 . . . . 177.4(2) ?
    C6 C7 C12 O1 . . . . -3.2(3) ?
    C8 C7 C12 C11 . . . . -2.9(3) ?
    C6 C7 C12 C11 . . . . 176.5(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
    O1 H1 O2 . 0.84(2) 1.97(2) 2.800(3) 169(4)
    N1 H3 O2 1_545 0.88(3) 2.33(2) 3.017(3) 134(2)
    N1 H3 O3 1_545 0.88(3) 2.00(3) 2.860(4) 165(3)
    N2 H2 O3 3_546 0.875(13) 2.36(2) 3.089(3) 141(3)
    N2 H2 O4 3_546 0.875(13) 2.182(19) 3.027(3) 162(3)
