#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/21/2212148.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_2212148
loop_
_publ_author_name
'Rademeyer, Melanie'
_publ_section_title
;
 2-Aminopyridinium nitrate
;
_journal_coeditor_code           ER2017
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o545
_journal_page_last               o546
_journal_paper_doi               10.1107/S1600536806055693
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C5 H7 N2 + , N O3 -'
_chemical_formula_moiety         'C5 H7 N2 + , N O3 -'
_chemical_formula_sum            'C5 H7 N3 O3'
_chemical_formula_weight         157.14
_chemical_name_systematic
;
2-Aminopyridinium nitrate
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 115.752(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.5559(11)
_cell_length_b                   3.64730(10)
_cell_length_c                   19.4851(8)
_cell_measurement_reflns_used    948
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      2
_cell_volume                     1379.79(11)
_computing_cell_refinement       'CrysAlis CCD'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2003)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2003)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and MERCURY (Macrae et al.,
2006)
;
_computing_publication_material
'PLATON (Spek, 2003) and WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.861
_diffrn_measurement_device_type  'Oxford Excalibur2'
_diffrn_measurement_method       ω/2θ
_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  0.0173
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            20896
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         34.21
_diffrn_reflns_theta_min         4.18
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  0.9825
_exptl_absorpt_correction_T_min  0.9491
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.303
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         4939
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0400
_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)+(0.0641P)²+0.2988P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1217
_reflns_number_gt                3460
_reflns_number_total             4939
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            er2017.cif
_cod_data_source_block           I
_cod_original_cell_volume        1379.79(10)
_cod_original_sg_symbol_H-M      'P 2/c'
_cod_database_code               2212148
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-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
N N2 0.21685(5) 0.7605(3) 0.44255(5) 0.0232(2) Uani d . 1
H H2A 0.2132 0.6850 0.3991 0.028 Uiso calc R 1
H H2B 0.2556 0.7433 0.4823 0.028 Uiso calc R 1
N N4 0.28548(5) 0.2903(3) 0.22943(6) 0.0261(2) Uani d . 1
H H4A 0.2901 0.3560 0.1895 0.031 Uiso calc R 1
H H4B 0.2465 0.3174 0.2311 0.031 Uiso calc R 1
H H3A 0.4017(8) 0.195(4) 0.2444(9) 0.031(4) Uiso d . 1
H H1A 0.1000(8) 0.839(5) 0.3399(9) 0.034(4) Uiso d . 1
O O5 0.07779(4) 0.5833(3) 0.24849(5) 0.0280(2) Uani d . 1
N N1 0.10231(5) 0.9280(3) 0.38510(5) 0.01788(18) Uani d . 1
N N6 0.12834(5) 0.4795(3) 0.23775(5) 0.02012(19) Uani d . 1
C C5 0.16261(6) 0.9039(3) 0.44829(6) 0.0176(2) Uani d . 1
O O6 0.12076(5) 0.3578(3) 0.17551(5) 0.0291(2) Uani d . 1
C C2 0.04407(6) 1.1934(3) 0.45110(6) 0.0217(2) Uani d . 1
H H2 0.0043 1.2898 0.4516 0.026 Uiso calc R 1
C C3 0.10593(6) 1.1731(3) 0.51847(6) 0.0220(2) Uani d . 1
H H3 0.1070 1.2551 0.5641 0.026 Uiso calc R 1
C C4 0.16429(6) 1.0348(3) 0.51749(6) 0.0209(2) Uani d . 1
H H4 0.2050 1.0264 0.5621 0.025 Uiso calc R 1
C C1 0.04402(6) 1.0682(3) 0.38525(6) 0.0208(2) Uani d . 1
H H1 0.0038 1.0789 0.3401 0.025 Uiso calc R 1
O O4 0.18725(5) 0.5006(4) 0.29127(6) 0.0528(4) Uani d . 1
N N3 0.39917(5) 0.1076(3) 0.28445(5) 0.01796(18) Uani d . 1
C C10 0.33863(6) 0.1468(3) 0.28865(6) 0.0184(2) Uani d . 1
C C9 0.33569(6) 0.0333(3) 0.35649(7) 0.0229(2) Uani d . 1
H H9 0.2951 0.0597 0.3619 0.027 Uiso calc R 1
C C7 0.45429(6) -0.1560(3) 0.40664(6) 0.0230(2) Uani d . 1
H H7 0.4930 -0.2599 0.4456 0.028 Uiso calc R 1
C C8 0.39264(7) -0.1154(3) 0.41411(6) 0.0240(2) Uani d . 1
H H8 0.3906 -0.1904 0.4587 0.029 Uiso calc R 1
C C6 0.45608(6) -0.0401(3) 0.34132(6) 0.0209(2) Uani d . 1
H H6 0.4965 -0.0621 0.3355 0.025 Uiso calc R 1
O O1 0.37945(5) 0.6265(3) 0.05292(5) 0.0315(2) Uani d . 1
O O2 0.42056(4) 0.5031(3) 0.17353(5) 0.0272(2) Uani d . 1
N N5 0.37156(5) 0.5033(3) 0.10757(5) 0.0212(2) Uani d . 1
O O3 0.31433(5) 0.3739(3) 0.09833(5) 0.0344(2) 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
C5 N2 H2A 120.0
C5 N2 H2B 120.0
H2A N2 H2B 120.0
C10 N4 H4A 120.0
C10 N4 H4B 120.0
H4A N4 H4B 120.0
C5 N1 C1 123.21(9)
C5 N1 H1A 118.7(10)
C1 N1 H1A 118.1(10)
O6 N6 O4 119.74(10)
O6 N6 O5 121.26(10)
O4 N6 O5 119.00(9)
N2 C5 N1 118.85(9)
N2 C5 C4 123.59(10)
N1 C5 C4 117.56(10)
C1 C2 C3 118.24(10)
C1 C2 H2 120.9
C3 C2 H2 120.9
C4 C3 C2 120.80(10)
C4 C3 H3 119.6
C2 C3 H3 119.6
C3 C4 C5 119.75(10)
C3 C4 H4 120.1
C5 C4 H4 120.1
N1 C1 C2 120.44(10)
N1 C1 H1 119.8
C2 C1 H1 119.8
C10 N3 C6 123.17(9)
C10 N3 H3A 117.1(11)
C6 N3 H3A 119.6(11)
N4 C10 N3 118.68(9)
N4 C10 C9 123.73(10)
N3 C10 C9 117.59(10)
C8 C9 C10 119.75(10)
C8 C9 H9 120.1
C10 C9 H9 120.1
C6 C7 C8 118.52(10)
C6 C7 H7 120.7
C8 C7 H7 120.7
C9 C8 C7 120.61(10)
C9 C8 H8 119.7
C7 C8 H8 119.7
N3 C6 C7 120.36(10)
N3 C6 H6 119.8
C7 C6 H6 119.8
O1 N5 O3 120.47(10)
O1 N5 O2 120.79(10)
O3 N5 O2 118.75(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N2 C5 1.3292(14)
N2 H2A 0.8600
N2 H2B 0.8600
N4 C10 1.3301(15)
N4 H4A 0.8600
N4 H4B 0.8600
O5 N6 1.2540(12)
N1 C5 1.3501(13)
N1 C1 1.3577(14)
N1 H1A 0.920(16)
N6 O6 1.2338(12)
N6 O4 1.2470(13)
C5 C4 1.4159(14)
C2 C1 1.3616(15)
C2 C3 1.4092(16)
C2 H2 0.9300
C3 C4 1.3631(16)
C3 H3 0.9300
C4 H4 0.9300
C1 H1 0.9300
N3 C10 1.3503(13)
N3 C6 1.3571(14)
N3 H3A 0.866(16)
C10 C9 1.4125(15)
C9 C8 1.3653(17)
C9 H9 0.9300
C7 C6 1.3573(16)
C7 C8 1.4061(17)
C7 H7 0.9300
C8 H8 0.9300
C6 H6 0.9300
O1 N5 1.2339(12)
O2 N5 1.2600(12)
N5 O3 1.2585(13)
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
N3 H3A O2 . 0.866(16) 1.956(16) 2.7983(13) 164(2)
N4 H4B O4 . 0.86 2.18 2.9564(14) 150
N4 H4A O3 . 0.86 2.06 2.8959(13) 164
N1 H1A O5 . 0.920(16) 1.878(16) 2.7790(13) 166(2)
N2 H2A O4 . 0.86 2.04 2.8915(14) 170
N2 H2B O3 4_566 0.86 2.10 2.8856(13) 152
N4 H4B O6 . 0.86 2.45 3.2450(14) 154
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 N1 C5 N2 179.64(10)
C1 N1 C5 C4 -0.41(16)
C1 C2 C3 C4 0.58(17)
C2 C3 C4 C5 -1.08(17)
N2 C5 C4 C3 -179.06(11)
N1 C5 C4 C3 0.98(16)
C5 N1 C1 C2 -0.09(17)
C3 C2 C1 N1 0.01(16)
C6 N3 C10 N4 -179.08(11)
C6 N3 C10 C9 1.19(16)
N4 C10 C9 C8 179.21(12)
N3 C10 C9 C8 -1.08(17)
C10 C9 C8 C7 0.12(18)
C6 C7 C8 C9 0.78(18)
C10 N3 C6 C7 -0.30(17)
C8 C7 C6 N3 -0.71(17)
