#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/49/2224912.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_2224912
loop_
_publ_author_name
'Hemamalini, Madhukar'
'Fun, Hoong-Kun'
_publ_section_title
;
 2-Amino-4-methylpyridinium 4-nitrobenzoate
;
_journal_coeditor_code           CI5013
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o335
_journal_paper_doi               10.1107/S1600536810000693
_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-4-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                 92.1940(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.5267(2)
_cell_length_b                   5.01870(10)
_cell_length_c                   12.2436(3)
_cell_measurement_reflns_used    3965
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      34.79
_cell_measurement_theta_min      3.33
_cell_volume                     646.36(2)
_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  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
;
Bruker SMART APEXII 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  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0343
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10644
_diffrn_reflns_theta_full        35.04
_diffrn_reflns_theta_max         35.04
_diffrn_reflns_theta_min         1.94
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.9828
_exptl_absorpt_correction_T_min  0.9493
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.491
_exptl_crystal_size_mid          0.282
_exptl_crystal_size_min          0.162
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.296
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2841
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0468
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0808P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1171
_refine_ls_wR_factor_ref         0.1244
_reflns_number_gt                2390
_reflns_number_total             2841
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci5013.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               2224912
_cod_database_fobs_code          2224912
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
O O1 0.80158(13) 0.6741(3) -0.02376(11) 0.0242(3) Uani d . 1 . .
O O2 0.71718(12) 0.7465(3) 0.13779(10) 0.0199(2) Uani d . 1 . .
O O3 1.22450(16) -0.2278(4) 0.19930(13) 0.0424(5) Uani d . 1 . .
O O4 1.13745(12) -0.1978(3) 0.35531(10) 0.0223(3) Uani d . 1 . .
N N1 1.14461(14) -0.1369(3) 0.25872(13) 0.0198(3) Uani d . 1 . .
C C1 0.79450(13) 0.6328(3) 0.07603(12) 0.0153(3) Uani d . 1 . .
C C2 0.88627(14) 0.4321(3) 0.12679(12) 0.0148(3) Uani d . 1 . .
C C3 0.96760(16) 0.2969(4) 0.05869(14) 0.0207(3) Uani d . 1 . .
C C4 1.05331(17) 0.1098(4) 0.10127(14) 0.0222(3) Uani d . 1 . .
C C5 1.05432(15) 0.0620(3) 0.21297(13) 0.0171(3) Uani d . 1 . .
C C6 0.97482(15) 0.1920(3) 0.28289(13) 0.0162(3) Uani d . 1 . .
C C7 0.88970(14) 0.3788(4) 0.23830(13) 0.0160(3) Uani d . 1 . .
N N2 0.57997(13) 0.1076(3) 1.02192(11) 0.0178(3) Uani d . 1 . .
N N3 0.67843(14) 0.0756(3) 0.85722(12) 0.0210(3) Uani d . 1 . .
C C8 0.49010(17) 0.2097(4) 1.08697(15) 0.0214(3) Uani d . 1 . .
C C9 0.40877(17) 0.4041(4) 1.05116(16) 0.0240(3) Uani d . 1 . .
C C10 0.41950(16) 0.5031(3) 0.94309(15) 0.0207(3) Uani d . 1 . .
C C11 0.51011(15) 0.3970(3) 0.87848(14) 0.0193(3) Uani d . 1 . .
C C12 0.59201(15) 0.1925(3) 0.91783(14) 0.0169(3) Uani d . 1 . .
C C13 0.33051(18) 0.7156(4) 0.90181(19) 0.0259(4) Uani d . 1 . .
H H13A 0.3574 0.7791 0.8324 0.039 Uiso calc R 1 . .
H H13B 0.3308 0.8605 0.9530 0.039 Uiso calc R 1 . .
H H13C 0.2462 0.6439 0.8934 0.039 Uiso calc R 1 . .
H H3A 0.969(2) 0.351(5) -0.017(2) 0.023(6) Uiso d . 1 . .
H H4A 1.110(2) 0.010(5) 0.055(2) 0.020(6) Uiso d . 1 . .
H H6A 0.977(2) 0.176(5) 0.364(2) 0.025(6) Uiso d . 1 . .
H H7A 0.833(2) 0.476(6) 0.289(2) 0.028(7) Uiso d . 1 . .
H H8A 0.479(3) 0.152(6) 1.160(3) 0.045(9) Uiso d . 1 . .
H H9A 0.347(3) 0.490(6) 1.095(2) 0.036(7) Uiso d . 1 . .
H H11A 0.519(3) 0.464(6) 0.804(2) 0.029(6) Uiso d . 1 . .
H H1N2 0.631(3) -0.026(7) 1.052(3) 0.043(8) Uiso d . 1 . .
H H1N3 0.690(3) 0.148(8) 0.796(3) 0.054(10) Uiso d . 1 . .
H H2N3 0.726(3) -0.058(7) 0.894(3) 0.046(8) 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
O3 N1 O4 . . 123.39(16) ?
O3 N1 C5 . . 118.38(16) ?
O4 N1 C5 . . 118.21(14) ?
O1 C1 O2 . . 125.08(16) ?
O1 C1 C2 . . 116.94(13) ?
O2 C1 C2 . . 117.98(14) ?
C7 C2 C3 . . 120.02(15) ?
C7 C2 C1 . . 121.57(13) ?
C3 C2 C1 . . 118.40(14) ?
C4 C3 C2 . . 120.61(16) ?
C4 C3 H3A . . 121.0(14) ?
C2 C3 H3A . . 118.0(14) ?
C5 C4 C3 . . 117.84(15) ?
C5 C4 H4A . . 120.0(14) ?
C3 C4 H4A . . 122.1(14) ?
C6 C5 C4 . . 123.09(15) ?
C6 C5 N1 . . 118.73(15) ?
C4 C5 N1 . . 118.17(15) ?
C5 C6 C7 . . 118.03(15) ?
C5 C6 H6A . . 126.2(14) ?
C7 C6 H6A . . 115.6(14) ?
C2 C7 C6 . . 120.40(14) ?
C2 C7 H7A . . 121.4(16) ?
C6 C7 H7A . . 118.2(16) ?
C12 N2 C8 . . 121.65(14) ?
C12 N2 H1N2 . . 122.2(19) ?
C8 N2 H1N2 . . 116.1(19) ?
C12 N3 H1N3 . . 116(2) ?
C12 N3 H2N3 . . 114.0(19) ?
H1N3 N3 H2N3 . . 130(3) ?
C9 C8 N2 . . 121.68(17) ?
C9 C8 H8A . . 115.0(19) ?
N2 C8 H8A . . 123.4(19) ?
C8 C9 C10 . . 118.65(15) ?
C8 C9 H9A . . 125.2(17) ?
C10 C9 H9A . . 116.0(18) ?
C11 C10 C9 . . 118.90(15) ?
C11 C10 C13 . . 121.55(17) ?
C9 C10 C13 . . 119.53(17) ?
C10 C11 C12 . . 120.97(16) ?
C10 C11 H11A . . 119.6(16) ?
C12 C11 H11A . . 119.4(16) ?
N3 C12 N2 . . 118.43(15) ?
N3 C12 C11 . . 123.42(16) ?
N2 C12 C11 . . 118.13(15) ?
C10 C13 H13A . . 109.5 ?
C10 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C10 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
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 C1 . 1.244(2) ?
O2 C1 . 1.2675(19) ?
O3 N1 . 1.221(2) ?
O4 N1 . 1.227(2) ?
N1 C5 . 1.474(2) ?
C1 C2 . 1.513(2) ?
C2 C7 . 1.390(2) ?
C2 C3 . 1.394(2) ?
C3 C4 . 1.390(3) ?
C3 H3A . 0.96(3) ?
C4 C5 . 1.388(2) ?
C4 H4A . 0.98(2) ?
C5 C6 . 1.383(2) ?
C6 C7 . 1.394(2) ?
C6 H6A . 0.99(3) ?
C7 H7A . 1.00(3) ?
N2 C12 . 1.354(2) ?
N2 C8 . 1.360(2) ?
N2 H1N2 . 0.93(3) ?
N3 C12 . 1.332(2) ?
N3 H1N3 . 0.85(4) ?
N3 H2N3 . 0.94(3) ?
C8 C9 . 1.359(3) ?
C8 H8A . 0.95(3) ?
C9 C10 . 1.422(3) ?
C9 H9A . 0.96(3) ?
C10 C11 . 1.370(2) ?
C10 C13 . 1.495(3) ?
C11 C12 . 1.413(2) ?
C11 H11A . 0.98(3) ?
C13 H13A . 0.96 ?
C13 H13B . 0.96 ?
C13 H13C . 0.96 ?
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 O1 1_546 0.93(3) 2.55(3) 3.254(2) 134(3) yes
N2 H1N2 O2 1_546 0.93(3) 1.78(3) 2.688(2) 167(3) yes
N3 H1N3 O2 2_565 0.85(4) 2.04(4) 2.875(2) 170(4) yes
N3 H2N3 O1 1_546 0.94(3) 1.84(3) 2.778(2) 173(3) yes
C3 H3A O4 2_554 0.97(2) 2.53(2) 3.160(2) 123(2) yes
C6 H6A O1 2_565 1.00(2) 2.46(2) 3.116(2) 123(3) yes
C7 H7A O1 2_565 1.00(3) 2.45(3) 3.102(2) 122(2) yes
C9 H9A O3 1_466 0.96(3) 2.33(3) 3.276(3) 168(3) yes
C13 H13C O4 2_455 0.96 2.55 3.335(2) 139 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
O1 C1 C2 C7 . . . . 177.48(16) ?
O2 C1 C2 C7 . . . . -2.2(2) ?
O1 C1 C2 C3 . . . . -3.3(2) ?
O2 C1 C2 C3 . . . . 177.03(16) ?
C7 C2 C3 C4 . . . . -0.5(3) ?
C1 C2 C3 C4 . . . . -179.77(17) ?
C2 C3 C4 C5 . . . . 0.4(3) ?
C3 C4 C5 C6 . . . . -0.3(3) ?
C3 C4 C5 N1 . . . . 179.75(17) ?
O3 N1 C5 C6 . . . . -171.50(18) ?
O4 N1 C5 C6 . . . . 6.8(2) ?
O3 N1 C5 C4 . . . . 8.5(3) ?
O4 N1 C5 C4 . . . . -173.20(17) ?
C4 C5 C6 C7 . . . . 0.2(3) ?
N1 C5 C6 C7 . . . . -179.78(15) ?
C3 C2 C7 C6 . . . . 0.5(2) ?
C1 C2 C7 C6 . . . . 179.72(15) ?
C5 C6 C7 C2 . . . . -0.4(2) ?
C12 N2 C8 C9 . . . . -0.7(3) ?
N2 C8 C9 C10 . . . . -0.5(3) ?
C8 C9 C10 C11 . . . . 0.8(3) ?
C8 C9 C10 C13 . . . . 179.63(18) ?
C9 C10 C11 C12 . . . . 0.0(2) ?
C13 C10 C11 C12 . . . . -178.76(16) ?
C8 N2 C12 N3 . . . . -177.11(16) ?
C8 N2 C12 C11 . . . . 1.5(2) ?
C10 C11 C12 N3 . . . . 177.40(17) ?
C10 C11 C12 N2 . . . . -1.2(2) ?
