#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:49:58 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301806 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/12/2231225.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_2231225
loop_
_publ_author_name
'Berrah, Fadila'
'Bouacida, Sofiane'
'Roisnel, Thierry'
_publ_section_title
;
 2-Amino-3-carboxypyridinium nitrate
;
_journal_coeditor_code           LX2193
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2057
_journal_page_last               o2058
_journal_paper_doi               10.1107/S1600536811027978
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C6 H7 N2 O2 +, N O3 -'
_chemical_formula_moiety         'C6 H7 N2 O2 +, N O3 -'
_chemical_formula_structural     'C6 H7 N2 O2, N O3'
_chemical_formula_sum            'C6 H7 N3 O5'
_chemical_formula_weight         201.15
_chemical_name_systematic
;
2-Amino-3-carboxypyridinium nitrate
;
_space_group_IT_number           110
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'I 4bw -2c'
_symmetry_space_group_name_H-M   'I 41 c d'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   16.122(2)
_cell_length_b                   16.122(2)
_cell_length_c                   12.446(3)
_cell_measurement_reflns_used    491
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      20.26
_cell_measurement_theta_min      3.27
_cell_volume                     3235.0(10)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg & Berndt, 2001)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2002 (Burla et al., 2005)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1116
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5438
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.27
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.476
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.284
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1509
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.964
_refine_ls_R_factor_all          0.1093
_refine_ls_R_factor_gt           0.0593
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0760P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1308
_refine_ls_wR_factor_ref         0.1577
_reflns_number_gt                921
_reflns_number_total             1509
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            lx2193.cif
_cod_data_source_block           I
_cod_original_cell_volume        3235.0(11)
_cod_database_code               2231225
_cod_database_fobs_code          2231225
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -y,1/2+x,1/4+z
3 1/2-x,1/2-y,1/2+z
4 1/2+y,-x,3/4+z
5 -x,y,1/2+z
6 -y,1/2-x,3/4+z
7 1/2+x,1/2-y,z
8 1/2+y,x,1/4+z
9 1/2+x,1/2+y,1/2+z
10 1/2-y,x,3/4+z
11 -x,-y,z
12 y,1/2-x,1/4+z
13 1/2-x,1/2+y,z
14 1/2-y,-x,1/4+z
15 x,-y,1/2+z
16 y,1/2+x,3/4+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_symmetry_multiplicity
C C1 0.1754(3) 0.1137(3) 0.0309(6) 0.0288(11) Uani d . 1 2
C C2 0.1875(3) 0.0223(2) 0.0276(6) 0.0229(10) Uani d . 1 2
C C3 0.1218(3) -0.0300(3) 0.0259(6) 0.0295(12) Uani d . 1 2
H H3 0.0686 -0.0078 0.0264 0.035 Uiso calc R 1 2
C C4 0.1311(3) -0.1174(3) 0.0233(7) 0.0309(11) Uani d . 1 2
H H4 0.0854 -0.1526 0.0215 0.037 Uiso calc R 1 2
C C5 0.2092(3) -0.1469(3) 0.0235(7) 0.0302(12) Uani d . 1 2
H H5 0.2179 -0.2039 0.0221 0.036 Uiso calc R 1 2
C C6 0.2702(2) -0.0099(3) 0.0279(10) 0.0234(10) Uani d . 1 2
N N1 0.1623(2) -0.0149(2) 0.2777(8) 0.0247(8) Uani d . 1 2
N N2 0.2755(2) -0.0950(2) 0.0256(5) 0.0269(9) Uani d . 1 2
H H2 0.3242 -0.1168 0.0256 0.032 Uiso calc R 1 2
N N3 0.3388(2) 0.0327(2) 0.0312(5) 0.0308(10) Uani d . 1 2
H H3A 0.3858 0.0075 0.032 0.037 Uiso calc R 1 2
H H3B 0.3371 0.086 0.0326 0.037 Uiso calc R 1 2
O O1 0.20156(19) 0.05016(19) 0.2755(4) 0.0313(8) Uani d . 1 2
O O2 0.08451(16) -0.01536(18) 0.2757(5) 0.0293(8) Uani d . 1 2
O O3 0.19907(18) -0.08530(18) 0.2798(5) 0.0309(8) Uani d . 1 2
O O5 0.09671(19) 0.13575(18) 0.0242(4) 0.0342(9) Uani d . 1 2
H H51 0.0932 0.1865 0.0259 0.051 Uiso calc R 1 2
O O4 0.2318(2) 0.1628(2) 0.0360(4) 0.0355(10) Uani d . 1 2
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 0 '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 0.006 '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
O4 C1 O5 123.4(4)
O4 C1 C2 123.5(4)
O5 C1 C2 113.0(4)
C3 C2 C6 120.2(4)
C3 C2 C1 121.0(4)
C6 C2 C1 118.8(4)
C2 C3 C4 122.5(4)
C2 C3 H3 118.8
C4 C3 H3 118.8
C5 C4 C3 116.8(4)
C5 C4 H4 121.6
C3 C4 H4 121.6
C4 C5 N2 121.2(4)
C4 C5 H5 119.4
N2 C5 H5 119.4
N3 C6 N2 118.2(4)
N3 C6 C2 126.9(5)
N2 C6 C2 114.8(4)
O1 N1 O2 121.4(4)
O1 N1 O3 121.4(3)
O2 N1 O3 117.2(3)
C5 N2 C6 124.5(4)
C5 N2 H2 117.8
C6 N2 H2 117.8
C6 N3 H3A 120
C6 N3 H3B 120
H3A N3 H3B 120
C1 O5 H51 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O4 1.207(6)
C1 O5 1.319(6)
C1 C2 1.487(6)
C2 C3 1.354(6)
C2 C6 1.431(5)
C3 C4 1.417(6)
C3 H3 0.93
C4 C5 1.347(8)
C4 H4 0.93
C5 N2 1.359(6)
C5 H5 0.93
C6 N3 1.303(5)
C6 N2 1.375(6)
N1 O1 1.225(4)
N1 O2 1.255(4)
N1 O3 1.281(4)
N2 H2 0.86
N3 H3A 0.86
N3 H3B 0.86
O5 H51 0.82
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 H2 O3 4_554 0.86 1.97 2.803(4) 162 yes
N3 H3A O2 4_554 0.86 2.18 3.017(4) 165 yes
N3 H3A O2 10_554 0.86 2.43 2.967(4) 121 yes
N3 H3B O4 . 0.86 2.10 2.716(5) 128 yes
O5 H51 O3 6_554 0.82 1.85 2.670(4) 180 yes
C4 H4 O1 16_544 0.93 2.42 3.197(6) 141 yes
C5 H5 O4 13_545 0.93 2.30 3.216(6) 167 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
O4 C1 C2 C3 177.5(7)
O5 C1 C2 C3 -4.4(11)
O4 C1 C2 C6 -1.6(13)
O5 C1 C2 C6 176.4(9)
C6 C2 C3 C4 -0.6(12)
C1 C2 C3 C4 -179.7(7)
C2 C3 C4 C5 0.5(11)
C3 C4 C5 N2 -0.3(12)
C3 C2 C6 N3 -178.8(9)
C1 C2 C6 N3 0.4(17)
C3 C2 C6 N2 0.3(14)
C1 C2 C6 N2 179.5(7)
C4 C5 N2 C6 0.0(14)
N3 C6 N2 C5 179.1(8)
C2 C6 N2 C5 -0.1(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139081711
