#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/97/2219727.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_2219727
loop_
_publ_author_name
'Dai, Jing'
_publ_section_title
;
 2-Amino-5-cyanopyridinium nitrate
;
_journal_coeditor_code           WK2092
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1899
_journal_paper_doi               10.1107/S1600536808028031
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C6 H6 N3 + , N O3 -'
_chemical_formula_moiety         'C6 H6 N3 + , N O3 -'
_chemical_formula_sum            'C6 H6 N4 O3'
_chemical_formula_weight         182.15
_chemical_name_systematic
;
2-Amino-5-cyanopyridinium nitrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.91(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.6475(9)
_cell_length_b                   12.713(3)
_cell_length_c                   13.417(3)
_cell_measurement_reflns_used    1796
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.06
_cell_volume                     785.2(3)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Mercury2'
_diffrn_measurement_method       ω
_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  0.0503
_diffrn_reflns_av_sigmaI/netI    0.0409
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8053
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.07
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.167
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         1798
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0949
_refine_ls_R_factor_gt           0.0526
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0514P)²+0.1542P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1269
_reflns_number_gt                1163
_reflns_number_total             1798
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wk2092.cif
_cod_data_source_block           I
_cod_original_cell_volume        785.1(3)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2219727
_cod_database_fobs_code          2219727
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, 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_occupancy
C C2 0.7591(5) 0.86151(17) 0.31844(17) 0.0428(5) Uani d 1
N N4 0.0550(4) 0.94943(14) 0.12683(14) 0.0456(5) Uani d 1
N N2 0.4566(4) 0.71680(19) 0.25422(16) 0.0509(5) Uani d 1
O O1 -0.1866(3) 0.98288(12) 0.08728(13) 0.0604(5) Uani d 1
O O2 0.2162(4) 1.00628(14) 0.18518(14) 0.0651(5) Uani d 1
O O3 0.1266(4) 0.85819(13) 0.10891(13) 0.0610(5) Uani d 1
N N1 0.8152(4) 0.69031(15) 0.38842(14) 0.0406(4) Uani d 1
C C3 0.9809(5) 0.89511(17) 0.38692(17) 0.0435(5) Uani d 1
C C5 1.0356(4) 0.72284(18) 0.45750(17) 0.0402(5) Uani d 1
C C6 1.3541(5) 0.86115(17) 0.53382(18) 0.0476(6) Uani d 1
C C1 0.6718(4) 0.75525(16) 0.31857(15) 0.0379(5) Uani d 1
C C4 1.1235(4) 0.82498(16) 0.45893(16) 0.0388(5) Uani d 1
N N3 1.5342(5) 0.89264(16) 0.59161(18) 0.0684(7) Uani d 1
H H5 1.126(4) 0.6708(16) 0.5011(15) 0.036(5) Uiso d 1
H H2A 0.655(4) 0.9049(16) 0.2716(15) 0.033(5) Uiso d 1
H H3 1.041(4) 0.9695(19) 0.3867(16) 0.051(6) Uiso d 1
H H2B 0.401(5) 0.650(2) 0.2641(17) 0.048(7) Uiso d 1
H H1 0.764(5) 0.620(2) 0.389(2) 0.067(8) Uiso d 1
H H2C 0.370(6) 0.761(3) 0.216(2) 0.082(10) Uiso d 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
C2 0.0473(13) 0.0351(11) 0.0432(12) 0.0020(9) -0.0043(11) 0.0098(10)
N4 0.0556(12) 0.0365(10) 0.0425(10) 0.0046(9) -0.0013(9) 0.0013(9)
N2 0.0512(12) 0.0424(12) 0.0529(12) -0.0048(10) -0.0146(10) 0.0011(10)
O1 0.0532(10) 0.0445(9) 0.0766(12) 0.0102(8) -0.0156(9) -0.0064(8)
O2 0.0615(11) 0.0566(11) 0.0698(11) 0.0031(8) -0.0179(9) -0.0180(9)
O3 0.0770(12) 0.0405(9) 0.0599(11) 0.0171(8) -0.0098(9) -0.0044(8)
N1 0.0405(10) 0.0306(10) 0.0478(11) -0.0032(8) -0.0041(8) 0.0032(8)
C3 0.0471(13) 0.0323(12) 0.0492(13) -0.0021(10) -0.0003(11) 0.0029(10)
C5 0.0394(11) 0.0383(12) 0.0408(12) 0.0034(9) -0.0025(10) 0.0052(10)
C6 0.0495(14) 0.0373(12) 0.0515(14) -0.0002(10) -0.0089(12) 0.0008(10)
C1 0.0356(11) 0.0399(12) 0.0370(11) 0.0027(9) 0.0007(9) 0.0003(9)
C4 0.0355(11) 0.0377(12) 0.0414(11) -0.0002(9) -0.0014(9) 0.0020(10)
N3 0.0697(14) 0.0501(13) 0.0755(16) -0.0045(11) -0.0249(13) -0.0036(11)
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
C3 C2 C1 119.6(2)
C3 C2 H2A 123.7(12)
C1 C2 H2A 116.7(12)
O3 N4 O2 120.89(19)
O3 N4 O1 119.08(18)
O2 N4 O1 120.00(18)
C1 N2 H2B 117.2(15)
C1 N2 H2C 115(2)
H2B N2 H2C 127(3)
C5 N1 C1 123.0(2)
C5 N1 H1 117.7(16)
C1 N1 H1 119.4(17)
C2 C3 C4 120.5(2)
C2 C3 H3 119.4(13)
C4 C3 H3 120.0(13)
N1 C5 C4 120.1(2)
N1 C5 H5 116.3(12)
C4 C5 H5 123.6(12)
N3 C6 C4 177.9(2)
N2 C1 N1 118.9(2)
N2 C1 C2 123.1(2)
N1 C1 C2 118.07(19)
C5 C4 C3 118.77(19)
C5 C4 C6 120.53(19)
C3 C4 C6 120.69(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C2 C3 1.352(3)
C2 C1 1.411(3)
C2 H2A 0.92(2)
N4 O3 1.239(2)
N4 O2 1.239(2)
N4 O1 1.249(2)
N2 C1 1.322(3)
N2 H2B 0.90(2)
N2 H2C 0.83(3)
N1 C5 1.348(3)
N1 C1 1.354(3)
N1 H1 0.92(3)
C3 C4 1.411(3)
C3 H3 0.99(2)
C5 C4 1.361(3)
C5 H5 0.94(2)
C6 N3 1.133(3)
C6 C4 1.440(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
N2 H2B O2 2_545 0.90(2) 2.05(3) 2.941(3) 169(2)
N1 H1 O1 2_545 0.92(3) 1.82(3) 2.733(2) 170(2)
N1 H1 N4 2_545 0.92(3) 2.62(3) 3.505(3) 161(2)
N2 H2C O3 . 0.83(3) 2.10(3) 2.926(3) 174(3)
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
C1 C2 C3 C4 -0.6(3)
C1 N1 C5 C4 -0.2(3)
C5 N1 C1 N2 -179.4(2)
C5 N1 C1 C2 0.2(3)
C3 C2 C1 N2 179.8(2)
C3 C2 C1 N1 0.2(3)
N1 C5 C4 C3 -0.3(3)
N1 C5 C4 C6 178.5(2)
C2 C3 C4 C5 0.6(3)
C2 C3 C4 C6 -178.2(2)
