#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/66/2226675.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_2226675
loop_
_publ_author_name
'Sivaramkumar, M. S.'
'Velmurugan, R.'
'Sekar, M.'
'Ramesh, P.'
'Ponnuswamy, M. N.'
_publ_section_title
;
 2-Aminopyridinium picrate
;
_journal_coeditor_code           SJ5016
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1821
_journal_paper_doi               10.1107/S1600536810024220
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C5 H7 N2 +, C6 H2 N3 O7 -'
_chemical_formula_moiety         'C5 H7 N2 +, C6 H2 N3 O7 -'
_chemical_formula_sum            'C11 H9 N5 O7'
_chemical_formula_weight         323.23
_chemical_name_common            ' 2-Aminopyridinium picrate '
_chemical_name_systematic
;
2-Aminopyridinium picrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                114.641(4)
_cell_angle_beta                 100.204(3)
_cell_angle_gamma                103.928(3)
_cell_formula_units_Z            4
_cell_length_a                   11.2543(4)
_cell_length_b                   11.6588(5)
_cell_length_c                   12.9883(5)
_cell_measurement_reflns_used    1241
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      29.21
_cell_measurement_theta_min      2.89
_cell_volume                     1427.16(12)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.846
_diffrn_measurement_device_type
'Bruker SMART APEXII area-detector diffractometer'
_diffrn_measurement_method       'ω and φ 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  0.0202
_diffrn_reflns_av_sigmaI/netI    0.0602
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12905
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.21
_diffrn_reflns_theta_min         2.89
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.208
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.904
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     438
_refine_ls_number_reflns         6555
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.904
_refine_ls_R_factor_all          0.1116
_refine_ls_R_factor_gt           0.0537
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0994P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1601
_refine_ls_wR_factor_ref         0.1786
_reflns_number_gt                3011
_reflns_number_total             6555
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5016.cif
_cod_data_source_block           I
_cod_database_code               2226675
_cod_database_fobs_code          2226675
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 O1A 0.09943(15) 0.43819(16) 0.43463(15) 0.0536(5) Uani d . 1 . .
O O1B 0.23913(17) 0.3169(2) 0.1731(2) 0.0813(7) Uani d . 1 . .
O O2A 0.27377(16) 0.3677(2) 0.54622(19) 0.0748(6) Uani d . 1 . .
O O2B 0.40164(17) 0.3168(2) 0.3449(2) 0.0836(7) Uani d U 1 . .
O O3A 0.20270(17) 0.33859(19) 0.67855(17) 0.0710(6) Uani d . 1 . .
O O3B 0.36036(19) 0.1314(2) 0.3494(2) 0.0942(8) Uani d . 1 . .
O O4A -0.20594(19) -0.04375(18) 0.48852(19) 0.0745(6) Uani d . 1 . .
O O4B -0.0709(2) -0.1479(2) 0.2427(2) 0.0963(8) Uani d . 1 . .
O O5A -0.35954(18) -0.03632(19) 0.36907(19) 0.0752(6) Uani d . 1 . .
O O5B -0.2227(2) -0.1377(2) 0.1262(2) 0.1038(9) Uani d . 1 . .
O O6A -0.28300(19) 0.3105(3) 0.2612(2) 0.1067(9) Uani d . 1 . .
O O6B -0.14349(18) 0.1761(2) -0.0134(2) 0.0871(7) Uani d . 1 . .
O O7A -0.09658(17) 0.40685(19) 0.26526(17) 0.0671(6) Uani d . 1 . .
O O7B 0.03844(19) 0.3203(2) 0.0375(2) 0.0870(7) Uani d . 1 . .
N N1A 0.17461(19) 0.6011(2) 0.33902(18) 0.0435(5) Uani d . 1 . .
H H1A 0.124(2) 0.534(3) 0.342(2) 0.061(8) Uiso d . 1 . .
N N1B 0.31598(19) 0.4800(2) 0.08244(18) 0.0478(5) Uani d . 1 . .
H H1B 0.265(2) 0.409(3) 0.093(2) 0.070(8) Uiso d . 1 . .
C C2A 0.1199(3) 0.6384(3) 0.2628(2) 0.0538(7) Uani d . 1 . .
H H2A 0.0306 0.5945 0.2190 0.065 Uiso calc R 1 . .
C C2B 0.2668(3) 0.5098(3) -0.0024(3) 0.0631(8) Uani d . 1 . .
H H2B 0.1791 0.4623 -0.0508 0.076 Uiso calc R 1 . .
C C3A 0.1918(3) 0.7381(3) 0.2486(3) 0.0637(8) Uani d . 1 . .
H H3A 0.1542 0.7642 0.1944 0.076 Uiso calc R 1 . .
C C3B 0.3409(3) 0.6061(3) -0.0190(3) 0.0681(8) Uani d . 1 . .
H H3B 0.3069 0.6277 -0.0781 0.082 Uiso calc R 1 . .
C C4A 0.3221(3) 0.8020(3) 0.3147(3) 0.0616(8) Uani d . 1 . .
H H4A 0.3736 0.8727 0.3057 0.074 Uiso calc R 1 . .
C C4B 0.4689(3) 0.6726(3) 0.0531(3) 0.0621(8) Uani d . 1 . .
H H4B 0.5230 0.7404 0.0427 0.075 Uiso calc R 1 . .
C C5A 0.3761(3) 0.7650(2) 0.3913(2) 0.0556(7) Uani d . 1 . .
H H5A 0.4650 0.8096 0.4364 0.067 Uiso calc R 1 . .
C C5B 0.5183(2) 0.6432(2) 0.1379(2) 0.0527(7) Uani d . 1 . .
H H5B 0.6059 0.6905 0.1865 0.063 Uiso calc R 1 . .
C C6A 0.2995(2) 0.6592(2) 0.4042(2) 0.0417(6) Uani d . 1 . .
C C6B 0.4402(2) 0.5433(2) 0.1535(2) 0.0425(6) Uani d . 1 . .
N N7A 0.3450(2) 0.6145(2) 0.4761(2) 0.0557(6) Uani d . 1 . .
H H7A 0.427(3) 0.650(3) 0.514(3) 0.102(8) Uiso d . 1 . .
H H7B 0.287(3) 0.528(3) 0.474(3) 0.102(8) Uiso d . 1 . .
N N7B 0.4794(3) 0.5063(3) 0.2321(2) 0.0626(7) Uani d . 1 . .
H H7C 0.547(3) 0.539(3) 0.265(3) 0.060(10) Uiso d . 1 . .
H H7D 0.423(3) 0.450(3) 0.239(3) 0.070(10) Uiso d . 1 . .
C C8A 0.0194(2) 0.3402(2) 0.43135(19) 0.0361(5) Uani d . 1 . .
C C8B 0.1588(2) 0.2278(2) 0.1784(2) 0.0453(6) Uani d . 1 . .
C C9A 0.0536(2) 0.2783(2) 0.5026(2) 0.0386(5) Uani d . 1 . .
C C9B 0.1927(2) 0.1623(2) 0.2467(2) 0.0442(6) Uani d . 1 . .
C C10A -0.0308(2) 0.1731(2) 0.5044(2) 0.0411(6) Uani d . 1 . .
H H10A -0.0032 0.1371 0.5539 0.049 Uiso calc R 1 . .
C C10B 0.1087(2) 0.0598(2) 0.2493(2) 0.0451(6) Uani d . 1 . .
H H10B 0.1373 0.0203 0.2951 0.054 Uiso calc R 1 . .
C C11A -0.1580(2) 0.1204(2) 0.4318(2) 0.0385(5) Uani d . 1 . .
C C11B -0.0197(2) 0.0135(2) 0.1839(2) 0.0437(6) Uani d . 1 . .
C C12A -0.2003(2) 0.1743(2) 0.3635(2) 0.0389(5) Uani d . 1 . .
H H12A -0.2883 0.1384 0.3164 0.047 Uiso calc R 1 . .
C C12B -0.0629(2) 0.0708(2) 0.1180(2) 0.0397(6) Uani d . 1 . .
H H12B -0.1517 0.0384 0.0742 0.048 Uiso calc R 1 . .
C C13A -0.1151(2) 0.2806(2) 0.36324(19) 0.0376(5) Uani d . 1 . .
C C13B 0.0225(2) 0.1740(2) 0.1161(2) 0.0379(5) Uani d . 1 . .
N N14A 0.18554(19) 0.33227(19) 0.58082(19) 0.0484(5) Uani d . 1 . .
N N14B 0.3273(2) 0.2071(2) 0.3173(2) 0.0579(6) Uani d U 1 . .
N N15A -0.2477(2) 0.00586(19) 0.4296(2) 0.0524(6) Uani d . 1 . .
N N15B -0.1106(2) -0.0986(2) 0.1844(2) 0.0608(6) Uani d . 1 . .
N N16A -0.1678(2) 0.3358(2) 0.29156(18) 0.0493(5) Uani d . 1 . .
N N16B -0.0302(2) 0.2282(2) 0.04259(18) 0.0481(5) Uani 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 0.0016 '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'
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
C6A N1A C2A . . 123.2(2) ?
C6A N1A H1A . . 121.2(17) ?
C2A N1A H1A . . 115.6(17) ?
C6B N1B C2B . . 122.5(2) ?
C6B N1B H1B . . 115.8(15) ?
C2B N1B H1B . . 121.7(15) ?
C3A C2A N1A . . 120.1(3) ?
C3A C2A H2A . . 120.0 ?
N1A C2A H2A . . 120.0 ?
C3B C2B N1B . . 120.8(3) ?
C3B C2B H2B . . 119.6 ?
N1B C2B H2B . . 119.6 ?
C2A C3A C4A . . 118.9(2) ?
C2A C3A H3A . . 120.6 ?
C4A C3A H3A . . 120.6 ?
C2B C3B C4B . . 117.8(3) ?
C2B C3B H3B . . 121.1 ?
C4B C3B H3B . . 121.1 ?
C5A C4A C3A . . 120.8(2) ?
C5A C4A H4A . . 119.6 ?
C3A C4A H4A . . 119.6 ?
C5B C4B C3B . . 121.7(2) ?
C5B C4B H4B . . 119.2 ?
C3B C4B H4B . . 119.2 ?
C4A C5A C6A . . 119.6(3) ?
C4A C5A H5A . . 120.2 ?
C6A C5A H5A . . 120.2 ?
C4B C5B C6B . . 119.7(2) ?
C4B C5B H5B . . 120.2 ?
C6B C5B H5B . . 120.2 ?
N7A C6A N1A . . 118.9(2) ?
N7A C6A C5A . . 123.7(2) ?
N1A C6A C5A . . 117.4(2) ?
N7B C6B N1B . . 118.1(2) ?
N7B C6B C5B . . 124.3(2) ?
N1B C6B C5B . . 117.6(2) ?
C6A N7A H7A . . 118(2) ?
C6A N7A H7B . . 120.8(17) ?
H7A N7A H7B . . 120(3) ?
C6B N7B H7C . . 114(2) ?
C6B N7B H7D . . 117.1(19) ?
H7C N7B H7D . . 129(3) ?
O1A C8A C13A . . 125.4(2) ?
O1A C8A C9A . . 122.2(2) ?
C13A C8A C9A . . 112.30(19) ?
O1B C8B C13B . . 124.9(2) ?
O1B C8B C9B . . 123.2(2) ?
C13B C8B C9B . . 111.9(2) ?
C10A C9A C8A . . 124.6(2) ?
C10A C9A N14A . . 116.76(19) ?
C8A C9A N14A . . 118.66(19) ?
C10B C9B C8B . . 124.8(2) ?
C10B C9B N14B . . 116.4(2) ?
C8B C9B N14B . . 118.8(2) ?
C9A C10A C11A . . 118.2(2) ?
C9A C10A H10A . . 120.9 ?
C11A C10A H10A . . 120.9 ?
C9B C10B C11B . . 118.6(2) ?
C9B C10B H10B . . 120.7 ?
C11B C10B H10B . . 120.7 ?
C12A C11A C10A . . 121.5(2) ?
C12A C11A N15A . . 119.6(2) ?
C10A C11A N15A . . 118.9(2) ?
C12B C11B C10B . . 121.4(2) ?
C12B C11B N15B . . 119.6(2) ?
C10B C11B N15B . . 119.0(2) ?
C11A C12A C13A . . 119.8(2) ?
C11A C12A H12A . . 120.1 ?
C13A C12A H12A . . 120.1 ?
C13B C12B C11B . . 119.5(2) ?
C13B C12B H12B . . 120.3 ?
C11B C12B H12B . . 120.3 ?
C12A C13A C8A . . 123.6(2) ?
C12A C13A N16A . . 116.78(19) ?
C8A C13A N16A . . 119.61(19) ?
C12B C13B C8B . . 123.8(2) ?
C12B C13B N16B . . 116.4(2) ?
C8B C13B N16B . . 119.77(19) ?
O2A N14A O3A . . 122.7(2) ?
O2A N14A C9A . . 119.2(2) ?
O3A N14A C9A . . 118.1(2) ?
O2B N14B O3B . . 121.8(2) ?
O2B N14B C9B . . 120.4(2) ?
O3B N14B C9B . . 117.7(2) ?
O5A N15A O4A . . 123.5(2) ?
O5A N15A C11A . . 118.3(2) ?
O4A N15A C11A . . 118.2(2) ?
O4B N15B O5B . . 123.4(2) ?
O4B N15B C11B . . 118.7(2) ?
O5B N15B C11B . . 117.9(2) ?
O7A N16A O6A . . 121.4(2) ?
O7A N16A C13A . . 120.0(2) ?
O6A N16A C13A . . 118.5(2) ?
O7B N16B O6B . . 121.4(2) ?
O7B N16B C13B . . 120.5(2) ?
O6B N16B C13B . . 118.1(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
O1A C8A . 1.252(2) ?
O1B C8B . 1.237(3) ?
O2A N14A . 1.214(3) ?
O2B N14B . 1.208(3) ?
O3A N14A . 1.217(2) ?
O3B N14B . 1.226(2) ?
O4A N15A . 1.230(3) ?
O4B N15B . 1.212(3) ?
O5A N15A . 1.214(3) ?
O5B N15B . 1.212(3) ?
O6A N16A . 1.209(2) ?
O6B N16B . 1.206(2) ?
O7A N16A . 1.208(2) ?
O7B N16B . 1.197(2) ?
N1A C6A . 1.339(3) ?
N1A C2A . 1.350(3) ?
N1A H1A . 0.87(3) ?
N1B C6B . 1.352(3) ?
N1B C2B . 1.356(3) ?
N1B H1B . 0.96(3) ?
C2A C3A . 1.348(3) ?
C2A H2A . 0.9500 ?
C2B C3B . 1.347(4) ?
C2B H2B . 0.9500 ?
C3A C4A . 1.391(4) ?
C3A H3A . 0.9500 ?
C3B C4B . 1.390(4) ?
C3B H3B . 0.9500 ?
C4A C5A . 1.348(3) ?
C4A H4A . 0.9500 ?
C4B C5B . 1.351(4) ?
C4B H4B . 0.9500 ?
C5A C6A . 1.416(3) ?
C5A H5A . 0.9500 ?
C5B C6B . 1.393(3) ?
C5B H5B . 0.9500 ?
C6A N7A . 1.331(3) ?
C6B N7B . 1.312(3) ?
N7A H7A . 0.87(3) ?
N7A H7B . 1.05(3) ?
N7B H7C . 0.72(3) ?
N7B H7D . 0.84(3) ?
C8A C13A . 1.436(3) ?
C8A C9A . 1.446(3) ?
C8B C13B . 1.441(3) ?
C8B C9B . 1.450(3) ?
C9A C10A . 1.371(3) ?
C9A N14A . 1.454(3) ?
C9B C10B . 1.351(3) ?
C9B N14B . 1.461(3) ?
C10A C11A . 1.389(3) ?
C10A H10A . 0.9500 ?
C10B C11B . 1.381(3) ?
C10B H10B . 0.9500 ?
C11A C12A . 1.367(3) ?
C11A N15A . 1.453(3) ?
C11B C12B . 1.379(3) ?
C11B N15B . 1.457(3) ?
C12A C13A . 1.374(3) ?
C12A H12A . 0.9500 ?
C12B C13B . 1.359(3) ?
C12B H12B . 0.9500 ?
C13A N16A . 1.456(3) ?
C13B N16B . 1.465(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
N1B H1B O1B 1 0.96(3) 1.79(3) 2.681(3) 152(2)
N1B H1B O7B 1 0.96(3) 2.36(3) 3.035(3) 127(2)
N7B H7D O1B 1 0.84(3) 2.04(3) 2.784(3) 148(3)
N7B H7D O2B 1 0.84(3) 2.47(3) 3.165(3) 141(2)
N1A H1A O1A 1 0.87(3) 1.97(3) 2.726(2) 145(2)
N1A H1A O7A 1 0.87(3) 2.34(3) 3.031(3) 137(2)
N7A H7B O2A 1 1.05(3) 2.40(3) 3.329(3) 147(2)
C10A H10A O4B 2_556 0.95 2.57 3.438(3) 152.7
N7A H7A O2B 2_666 0.87(3) 2.24(3) 3.029(3) 152(3)
N7B H7C O2A 2_666 0.72(3) 2.49(3) 3.137(3) 149(3)
