#------------------------------------------------------------------------------
#$Date: 2016-02-20 17:35:30 +0100 (Sat 20 de Feb de 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/58/2215867.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_2215867
loop_
_publ_author_name
'Aghabozorg, Hossein'
'Manteghi, Faranak'
'Ghadermazi, Mohammad'
_publ_section_title
;
 Ammonium 6-carboxypyridine-2-carboxylate
;
_journal_coeditor_code           CV2318
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4454
_journal_page_last               o4454
_journal_paper_doi               10.1107/S1600536807052610
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'H4 N + , C7 H4 N O4 -'
_chemical_formula_moiety         'H4 N + , C7 H4 N O4 -'
_chemical_formula_sum            'C7 H8 N2 O4'
_chemical_formula_weight         184.15
_chemical_name_systematic
;
Ammonium 6-carboxypyridine-2-carboxylate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 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                 125.651(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7033(11)
_cell_length_b                   12.0722(12)
_cell_length_c                   7.2121(7)
_cell_measurement_reflns_used    1992
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      34.82
_cell_measurement_theta_min      2.89
_cell_volume                     757.24(13)
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'APEX2 (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1998)'
_computing_publication_material  'SHELXTL (Sheldrick, 1998)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 1998)'
_computing_structure_solution    'SHELXTL (Sheldrick, 1998)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0201
_diffrn_reflns_av_sigmaI/netI    0.0183
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3303
_diffrn_reflns_theta_full        30.49
_diffrn_reflns_theta_max         30.49
_diffrn_reflns_theta_min         2.89
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  0.9358
_exptl_absorpt_correction_T_min  0.9358
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(APEX2; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cube
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.50
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.220
_refine_ls_extinction_coef       0.016(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 1998)'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     62
_refine_ls_number_reflns         1158
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0343
_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)+(0.0629P)²+0.3876P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1015
_reflns_number_gt                1081
_reflns_number_total             1158
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv2318.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2215867
_cod_database_fobs_code          2215867
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_refinement_flags
_atom_site_occupancy
O O1 0.73809(7) 0.61754(5) 0.13711(11) 0.01439(18) Uani d . 1
O O2 0.62331(7) 0.45370(5) 0.08777(12) 0.01787(19) Uani d . 1
H H1 0.5518 0.5000 0.0356 0.027 Uiso d PR 0.50
N N1 1.0000 0.50758(8) 0.2500 0.0100(2) Uani d S 1
C C1 0.73808(9) 0.51498(7) 0.14117(13) 0.01132(19) Uani d . 1
C C2 0.87885(8) 0.44959(6) 0.20657(12) 0.00989(19) Uani d . 1
C C3 0.87534(9) 0.33428(7) 0.21115(14) 0.01224(19) Uani d . 1
H H3A 0.7893 0.2967 0.1881 0.015 Uiso calc R 1
C C4 1.0000 0.27524(9) 0.2500 0.0135(2) Uani d S 1
H H4A 1.0000 0.1966 0.2500 0.016 Uiso calc SR 1
N N2 1.0000 0.75422(8) 0.2500 0.0144(2) Uani d S 1
H H2 0.9523 0.7984 0.1263 0.017 Uiso d R 1
H H3 0.9317 0.7089 0.2460 0.017 Uiso d R 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
O1 0.0108(3) 0.0103(3) 0.0208(3) 0.00095(19) 0.0085(3) -0.0002(2)
O2 0.0092(3) 0.0123(3) 0.0316(4) -0.0001(2) 0.0115(3) 0.0008(2)
N1 0.0080(4) 0.0092(4) 0.0121(4) 0.000 0.0054(4) 0.000
C1 0.0087(4) 0.0116(4) 0.0136(4) 0.0003(2) 0.0064(3) 0.0001(2)
C2 0.0076(3) 0.0095(4) 0.0117(4) 0.0001(2) 0.0052(3) 0.0000(2)
C3 0.0094(3) 0.0102(4) 0.0156(4) -0.0011(2) 0.0064(3) 0.0001(2)
C4 0.0112(5) 0.0087(4) 0.0180(5) 0.000 0.0070(4) 0.000
N2 0.0119(4) 0.0107(4) 0.0183(5) 0.000 0.0076(4) 0.000
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
C1 O2 H1 . . 102.4
C2 N1 C2 . 2_755 117.01(9)
O1 C1 O2 . . 125.55(7)
O1 C1 C2 . . 121.02(7)
O2 C1 C2 . . 113.41(7)
N1 C2 C3 . . 123.51(7)
N1 C2 C1 . . 116.90(7)
C3 C2 C1 . . 119.54(7)
C4 C3 C2 . . 118.76(7)
C4 C3 H3A . . 120.6
C2 C3 H3A . . 120.6
C3 C4 C3 2_755 . 118.29(10)
C3 C4 H4A 2_755 . 120.9
C3 C4 H4A . . 120.9
H2 N2 H3 . . 110.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C1 . 1.2385(10)
O2 C1 . 1.2857(9)
O2 H1 . 0.8389
N1 C2 . 1.3402(9)
N1 C2 2_755 1.3402(9)
C1 C2 . 1.5125(11)
C2 C3 . 1.3934(11)
C3 C4 . 1.3896(9)
C3 H3A . 0.9500
C4 C3 2_755 1.3896(9)
C4 H4A . 0.9500
N2 H2 . 0.8999
N2 H3 . 0.9000
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
O2 H1 O2 5_665 0.84 1.64 2.4340(10) 158 yes
N2 H2 O1 7_665 0.90 2.07 2.8970(10) 153 yes
N2 H3 O1 1_555 0.90 2.06 2.9300(10) 163 yes
N2 H3 N1 1_555 0.90 2.53 2.9770(10) 111 ?
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_4
_geom_torsion
C2 N1 C2 C3 2_755 . 1.91(5)
C2 N1 C2 C1 2_755 . -175.78(7)
O1 C1 C2 N1 . . -2.72(10)
O2 C1 C2 N1 . . 175.75(6)
O1 C1 C2 C3 . . 179.50(7)
O2 C1 C2 C3 . . -2.04(10)
N1 C2 C3 C4 . . -3.76(11)
C1 C2 C3 C4 . . 173.87(6)
C2 C3 C4 C3 . 2_755 1.74(5)
