#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/53/2225377.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2225377
loop_
_publ_author_name
'Hemamalini, Madhukar'
'Fun, Hoong-Kun'
_publ_section_title
;
 2-Amino-5-methylpyridinium 4-nitrobenzoate
;
_journal_coeditor_code           SJ2727
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o621
_journal_paper_doi               10.1107/S1600536810005301
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C6 H9 N2 +, C7 H4 N O4 -'
_chemical_formula_moiety         'C6 H9 N2 +, C7 H4 N O4 -'
_chemical_formula_sum            'C13 H13 N3 O4'
_chemical_formula_weight         275.26
_chemical_name_systematic
;
2-Amino-5-methylpyridinium 4-nitrobenzoate
;
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 114.94(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.684(12)
_cell_length_b                   4.025(4)
_cell_length_c                   12.706(11)
_cell_measurement_reflns_used    1854
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.15
_cell_measurement_theta_min      3.21
_cell_volume                     634.6(10)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
;
Bruker APEX DUO CCD area-detector diffractometer
;
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_sigmaI/netI    0.0383
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7053
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         1.64
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.9914
_exptl_absorpt_correction_T_min  0.9614
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.204
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         1854
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0604P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.1157
_reflns_number_gt                1283
_reflns_number_total             1854
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2727.cif
_cod_data_source_block           I
_cod_original_cell_volume        634.5(10)
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               2225377
_cod_database_fobs_code          2225377
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
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
N N1 0.83203(19) 0.0861(6) 0.16111(18) 0.0407(6) Uani d . 1 . .
N N2 0.7398(2) 0.0221(8) -0.0369(2) 0.0498(7) Uani d . 1 . .
C C1 0.8230(2) 0.1476(7) 0.0532(2) 0.0399(7) Uani d . 1 . .
C C2 0.9053(3) 0.3372(8) 0.0431(3) 0.0489(8) Uani d . 1 . .
C C3 0.9897(3) 0.4449(9) 0.1392(3) 0.0508(8) Uani d . 1 . .
C C4 0.9979(3) 0.3777(7) 0.2514(3) 0.0459(7) Uani d . 1 . .
C C5 0.9169(2) 0.1971(8) 0.2569(3) 0.0429(7) Uani d . 1 . .
C C6 1.0921(3) 0.4935(10) 0.3582(3) 0.0653(9) Uani d . 1 . .
H H6A 1.0781 0.4540 0.4251 0.098 Uiso calc R 1 . .
H H6B 1.1030 0.7269 0.3519 0.098 Uiso calc R 1 . .
H H6C 1.1555 0.3739 0.3662 0.098 Uiso calc R 1 . .
O O1 0.1957(2) -0.0891(11) 0.1134(2) 0.0995(12) Uani d . 1 . .
O O2 0.2751(3) -0.0198(10) 0.2954(3) 0.0953(11) Uani d . 1 . .
O O3 0.61995(19) 0.6210(7) 0.04604(18) 0.0613(7) Uani d . 1 . .
O O4 0.70099(15) 0.7415(6) 0.23282(17) 0.0504(5) Uani d . 1 . .
N N3 0.2718(2) 0.0063(7) 0.1991(2) 0.0548(7) Uani d . 1 . .
C C7 0.5306(2) 0.4378(8) 0.2704(2) 0.0401(6) Uani d . 1 . .
C C8 0.4456(2) 0.2895(8) 0.2828(2) 0.0428(6) Uani d . 1 . .
C C9 0.3641(2) 0.1565(7) 0.1870(2) 0.0400(6) Uani d . 1 . .
C C10 0.3648(3) 0.1575(8) 0.0790(3) 0.0470(7) Uani d . 1 . .
C C11 0.4522(2) 0.3019(8) 0.0683(2) 0.0443(7) Uani d . 1 . .
C C12 0.5345(2) 0.4473(7) 0.1622(2) 0.0339(5) Uani d . 1 . .
C C13 0.6260(2) 0.6165(7) 0.1462(2) 0.0401(7) Uani d . 1 . .
H H2A 0.896(2) 0.396(9) -0.035(3) 0.048(8) Uiso d . 1 . .
H H3A 1.042(3) 0.577(9) 0.131(3) 0.059(10) Uiso d . 1 . .
H H5A 0.915(3) 0.145(9) 0.328(3) 0.055(9) Uiso d . 1 . .
H H7A 0.585(2) 0.545(7) 0.333(2) 0.034(7) Uiso d . 1 . .
H H9A 0.442(3) 0.273(8) 0.355(4) 0.061(10) Uiso d . 1 . .
H H10A 0.308(3) 0.083(10) 0.017(3) 0.065(11) Uiso d . 1 . .
H H11A 0.459(3) 0.323(10) -0.006(4) 0.070(11) Uiso d . 1 . .
H H1N1 0.775(4) -0.035(9) 0.171(3) 0.059(10) Uiso d . 1 . .
H H1N2 0.728(3) 0.097(9) -0.107(3) 0.052(9) Uiso d . 1 . .
H H2N2 0.691(3) -0.087(9) -0.019(3) 0.055(10) Uiso d . 1 . .
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'
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
C1 N1 C5 . . 122.0(3) ?
C1 N1 H1N1 . . 119(2) ?
C5 N1 H1N1 . . 119(2) ?
C1 N2 H1N2 . . 117(2) ?
C1 N2 H2N2 . . 115(2) ?
H1N2 N2 H2N2 . . 125(3) ?
N2 C1 N1 . . 119.0(3) ?
N2 C1 C2 . . 123.7(3) ?
N1 C1 C2 . . 117.2(3) ?
C3 C2 C1 . . 120.2(3) ?
C3 C2 H2A . . 122.6(19) ?
C1 C2 H2A . . 117.1(19) ?
C2 C3 C4 . . 121.7(3) ?
C2 C3 H3A . . 119(2) ?
C4 C3 H3A . . 119(2) ?
C5 C4 C3 . . 116.0(3) ?
C5 C4 C6 . . 122.1(3) ?
C3 C4 C6 . . 121.8(3) ?
C4 C5 N1 . . 122.8(3) ?
C4 C5 H5A . . 122(2) ?
N1 C5 H5A . . 116(2) ?
C4 C6 H6A . . 109.5 ?
C4 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C4 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
O1 N3 O2 . . 122.2(3) ?
O1 N3 C9 . . 119.3(3) ?
O2 N3 C9 . . 118.4(3) ?
C8 C7 C12 . . 120.6(3) ?
C8 C7 H7A . . 121.1(18) ?
C12 C7 H7A . . 118.2(18) ?
C9 C8 C7 . . 118.7(3) ?
C9 C8 H9A . . 118(2) ?
C7 C8 H9A . . 123(2) ?
C8 C9 C10 . . 122.8(3) ?
C8 C9 N3 . . 118.9(2) ?
C10 C9 N3 . . 118.3(3) ?
C9 C10 C11 . . 117.9(3) ?
C9 C10 H10A . . 120(2) ?
C11 C10 H10A . . 122(2) ?
C12 C11 C10 . . 121.1(3) ?
C12 C11 H11A . . 115(2) ?
C10 C11 H11A . . 124(2) ?
C11 C12 C7 . . 118.9(3) ?
C11 C12 C13 . . 119.7(2) ?
C7 C12 C13 . . 121.4(2) ?
O3 C13 O4 . . 124.8(3) ?
O3 C13 C12 . . 116.3(2) ?
O4 C13 C12 . . 118.8(2) ?
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
N1 C1 . 1.347(3) ?
N1 C5 . 1.355(4) ?
N1 H1N1 . 0.97(4) ?
N2 C1 . 1.328(4) ?
N2 H1N2 . 0.89(4) ?
N2 H2N2 . 0.90(4) ?
C1 C2 . 1.410(4) ?
C2 C3 . 1.350(5) ?
C2 H2A . 0.97(3) ?
C3 C4 . 1.408(5) ?
C3 H3A . 0.94(4) ?
C4 C5 . 1.352(5) ?
C4 C6 . 1.499(5) ?
C5 H5A . 0.93(4) ?
C6 H6A . 0.9600 ?
C6 H6B . 0.9600 ?
C6 H6C . 0.9600 ?
O1 N3 . 1.208(4) ?
O2 N3 . 1.210(4) ?
O3 C13 . 1.241(3) ?
O4 C13 . 1.251(3) ?
N3 C9 . 1.466(4) ?
C7 C8 . 1.374(4) ?
C7 C12 . 1.399(4) ?
C7 H7A . 0.94(3) ?
C8 C9 . 1.366(4) ?
C8 H9A . 0.94(4) ?
C9 C10 . 1.375(4) ?
C10 C11 . 1.387(5) ?
C10 H10A . 0.89(4) ?
C11 C12 . 1.379(4) ?
C11 H11A . 0.98(4) ?
C12 C13 . 1.512(4) ?
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 H1N1 O3 1_545 0.97(5) 2.47(4) 3.238(5) 136(3) yes
N1 H1N1 O4 1_545 0.97(5) 1.77(5) 2.711(4) 163(3) yes
N2 H1N2 O4 2_564 0.89(4) 2.02(4) 2.905(4) 179(5) yes
N2 H2N2 O3 1_545 0.91(4) 1.92(4) 2.804(5) 165(4) yes
C3 H3A O1 1_665 0.93(4) 2.58(4) 3.514(6) 176(3) yes
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 N2 . . . . 177.7(3) ?
C5 N1 C1 C2 . . . . -0.7(4) ?
N2 C1 C2 C3 . . . . -177.3(3) ?
N1 C1 C2 C3 . . . . 1.1(4) ?
C1 C2 C3 C4 . . . . -1.0(5) ?
C2 C3 C4 C5 . . . . 0.6(5) ?
C2 C3 C4 C6 . . . . 179.3(3) ?
C3 C4 C5 N1 . . . . -0.2(5) ?
C6 C4 C5 N1 . . . . -178.9(3) ?
C1 N1 C5 C4 . . . . 0.3(4) ?
C12 C7 C8 C9 . . . . -1.1(4) ?
C7 C8 C9 C10 . . . . 1.6(5) ?
C7 C8 C9 N3 . . . . -178.3(3) ?
O1 N3 C9 C8 . . . . 174.4(4) ?
O2 N3 C9 C8 . . . . -6.1(5) ?
O1 N3 C9 C10 . . . . -5.5(5) ?
O2 N3 C9 C10 . . . . 173.9(3) ?
C8 C9 C10 C11 . . . . -0.3(5) ?
N3 C9 C10 C11 . . . . 179.6(3) ?
C9 C10 C11 C12 . . . . -1.6(5) ?
C10 C11 C12 C7 . . . . 2.1(4) ?
C10 C11 C12 C13 . . . . -177.2(3) ?
C8 C7 C12 C11 . . . . -0.8(4) ?
C8 C7 C12 C13 . . . . 178.5(3) ?
C11 C12 C13 O3 . . . . 1.7(4) ?
C7 C12 C13 O3 . . . . -177.6(3) ?
C11 C12 C13 O4 . . . . -178.7(3) ?
C7 C12 C13 O4 . . . . 2.1(4) ?
