#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/37/2233794.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_2233794
loop_
_publ_author_name
'Millán Corrales, Guadalupe'
'Morales-Morales, David'
'Hernández-Ortega, Simón'
'Campos-Gaxiola, José J.'
'Cruz Enríquez, Adriana'
_publ_section_title
;
 2-(3-Aminopyridinium-1-yl)-3-carboxypropanoate monohydrate
;
_journal_coeditor_code           FJ2513
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o853
_journal_paper_doi               10.1107/S1600536812006897
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C9 H10 N2 O4, H2 O'
_chemical_formula_moiety         'C9 H10 N2 O4, H2 O'
_chemical_formula_sum            'C9 H12 N2 O5'
_chemical_formula_weight         228.21
_chemical_name_systematic
;
2-(3-Aminopyridinium-1-yl)-3-carboxypropanoate monohydrate
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4939(8)
_cell_length_b                   19.446(2)
_cell_length_c                   7.0227(7)
_cell_measurement_reflns_used    5172
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.30
_cell_measurement_theta_min      2.91
_cell_volume                     1023.39(18)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and SHELXL97 (Sheldrick, 2008)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 0.83
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'omega 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  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0294
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            10663
_diffrn_reflns_theta_full        25.31
_diffrn_reflns_theta_max         25.31
_diffrn_reflns_theta_min         2.09
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.112
_refine_diff_density_min         -0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         1868
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0281
_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)+(0.0280P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0562
_refine_ls_wR_factor_ref         0.0575
_reflns_number_gt                1642
_reflns_number_total             1868
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fj2513.cif
_cod_data_source_block           I
_cod_original_cell_volume        1023.39(19)
_cod_database_code               2233794
_cod_database_fobs_code          2233794
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'
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
O O1 1.04824(15) 0.51597(6) 0.4732(2) 0.0417(3) Uani d . 1 1
O O2 1.13193(13) 0.41287(5) 0.36700(19) 0.0395(3) Uani d . 1 1
O O3 0.44407(15) 0.45071(7) 0.4070(2) 0.0565(4) Uani d D 1 1
H H3 0.3347(15) 0.4376(9) 0.389(3) 0.068 Uiso d D 1 1
O O4 0.45279(16) 0.39455(7) 0.67937(19) 0.0528(4) Uani d . 1 1
O O5 0.59669(18) 0.13525(7) 0.8132(2) 0.0557(4) Uani d D 1 1
H H5A 0.6976(17) 0.1248(11) 0.767(3) 0.067 Uiso d D 1 1
H H5B 0.559(3) 0.0989(7) 0.870(3) 0.067 Uiso d D 1 1
N N1 0.79643(15) 0.36728(7) 0.3184(2) 0.0291(3) Uani d . 1 1
N N2 0.6301(2) 0.28176(8) -0.1026(2) 0.0554(4) Uani d D 1 1
H H2A 0.605(2) 0.2377(6) -0.137(3) 0.066 Uiso d D 1 1
H H2B 0.581(2) 0.3184(8) -0.163(3) 0.066 Uiso d D 1 1
C C1 1.0183(2) 0.45789(8) 0.4126(2) 0.0307(4) Uani d . 1 1
C C2 0.81973(19) 0.43883(7) 0.3871(2) 0.0299(4) Uani d . 1 1
H H2 0.7699 0.4696 0.2902 0.036 Uiso calc R 1 1
C C3 0.7156(2) 0.45043(9) 0.5703(3) 0.0363(4) Uani d . 1 1
H H3A 0.7718 0.4246 0.6721 0.044 Uiso calc R 1 1
H H3B 0.7217 0.4988 0.6036 0.044 Uiso calc R 1 1
C C4 0.5235(2) 0.42955(8) 0.5568(3) 0.0341(4) Uani d . 1 1
C C5 0.7281(2) 0.35719(8) 0.1437(2) 0.0325(4) Uani d . 1 1
H H5 0.6999 0.3950 0.0682 0.039 Uiso calc R 1 1
C C6 0.6988(2) 0.29126(9) 0.0739(3) 0.0359(4) Uani d . 1 1
C C7 0.7427(2) 0.23635(9) 0.1932(3) 0.0411(5) Uani d . 1 1
H H7 0.7242 0.1914 0.1522 0.049 Uiso calc R 1 1
C C8 0.8125(2) 0.24828(8) 0.3696(3) 0.0412(4) Uani d . 1 1
H H8 0.8415 0.2114 0.4481 0.049 Uiso calc R 1 1
C C9 0.8403(2) 0.31445(8) 0.4320(3) 0.0376(4) Uani d . 1 1
H H9 0.8891 0.3225 0.5517 0.045 Uiso calc R 1 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
C4 O3 H3 117.7(16)
H5A O5 H5B 106(2)
C9 N1 C5 121.62(14)
C9 N1 C2 119.75(14)
C5 N1 C2 118.62(13)
C6 N2 H2A 116.6(14)
C6 N2 H2B 118.2(14)
H2A N2 H2B 122.2(18)
O1 C1 O2 127.07(14)
O1 C1 C2 115.91(14)
O2 C1 C2 117.02(14)
N1 C2 C3 110.72(13)
N1 C2 C1 112.11(12)
C3 C2 C1 111.15(13)
N1 C2 H2 107.5
C3 C2 H2 107.5
C1 C2 H2 107.5
C4 C3 C2 113.52(14)
C4 C3 H3A 108.9
C2 C3 H3A 108.9
C4 C3 H3B 108.9
C2 C3 H3B 108.9
H3A C3 H3B 107.7
O4 C4 O3 124.03(15)
O4 C4 C3 121.62(16)
O3 C4 C3 114.34(16)
N1 C5 C6 121.11(15)
N1 C5 H5 119.4
C6 C5 H5 119.4
N2 C6 C5 120.55(16)
N2 C6 C7 122.28(17)
C5 C6 C7 117.17(17)
C8 C7 C6 120.32(16)
C8 C7 H7 119.8
C6 C7 H7 119.8
C7 C8 C9 120.42(17)
C7 C8 H8 119.8
C9 C8 H8 119.8
N1 C9 C8 119.35(16)
N1 C9 H9 120.3
C8 C9 H9 120.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2276(18)
O2 C1 1.2623(19)
O3 C4 1.277(2)
O3 H3 0.868(9)
O4 C4 1.2183(19)
O5 H5A 0.848(9)
O5 H5B 0.861(9)
N1 C9 1.341(2)
N1 C5 1.344(2)
N1 C2 1.4830(18)
N2 C6 1.355(2)
N2 H2A 0.909(9)
N2 H2B 0.907(9)
C1 C2 1.544(2)
C2 C3 1.522(2)
C2 H2 0.9800
C3 C4 1.499(2)
C3 H3A 0.9700
C3 H3B 0.9700
C5 C6 1.390(2)
C5 H5 0.9300
C6 C7 1.396(2)
C7 C8 1.365(3)
C7 H7 0.9300
C8 C9 1.375(2)
C8 H8 0.9300
C9 H9 0.9300
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
O3 H3 O2 1_455 0.868(9) 1.601(10) 2.4681(15) 177(2)
O5 H5A O4 3 0.848(9) 2.043(10) 2.8879(18) 174(2)
O5 H5B O1 4_645 0.861(9) 1.941(10) 2.7968(19) 173(2)
N2 H2A O5 1_554 0.909(9) 2.024(10) 2.920(2) 168.3(18)
N2 H2B O4 1_554 0.907(9) 2.084(10) 2.987(2) 173(2)
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
C9 N1 C2 C3 -57.28(17)
C5 N1 C2 C3 121.47(14)
C9 N1 C2 C1 67.48(17)
C5 N1 C2 C1 -113.77(15)
O1 C1 C2 N1 -178.48(14)
O2 C1 C2 N1 2.4(2)
O1 C1 C2 C3 -53.95(19)
O2 C1 C2 C3 126.92(16)
N1 C2 C3 C4 -51.92(18)
C1 C2 C3 C4 -177.22(13)
C2 C3 C4 O4 132.57(18)
C2 C3 C4 O3 -46.5(2)
C9 N1 C5 C6 0.5(2)
C2 N1 C5 C6 -178.25(13)
N1 C5 C6 N2 -179.88(16)
N1 C5 C6 C7 0.3(2)
N2 C6 C7 C8 179.63(17)
C5 C6 C7 C8 -0.5(3)
C6 C7 C8 C9 0.1(3)
C5 N1 C9 C8 -0.9(2)
C2 N1 C9 C8 177.77(14)
C7 C8 C9 N1 0.7(3)
