##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2-Ammonio-3-carboxy-5-nitrobenzoate monohydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     "C8 H6 N2 O6, H2 O"
_chemical_formula_sum     'C8 H8 N2 O7'
_chemical_formula_iupac     "C8 H6 N2 O6, H2 O"
_chemical_formula_weight     244.16
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'C 2/c'
_symmetry_space_group_name_Hall     '-C 2yc'
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'
_cell_length_a     25.11(2)
_cell_length_b     6.5742(16)
_cell_length_c     12.221(2)
_cell_angle_alpha     90.00
_cell_angle_beta     112.0020(10)
_cell_angle_gamma     90.00
_cell_volume     1870.6(17)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     1493
_cell_measurement_theta_min     2.789
_cell_measurement_theta_max     26.804
_cell_measurement_temperature     273(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.24
_exptl_crystal_size_mid     0.15
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     1.734
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1008
_exptl_absorpt_coefficient_mu     0.156
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9636
_exptl_absorpt_correction_T_max     0.9776
_exptl_special_details
;
;
_diffrn_ambient_temperature     273(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6078
_diffrn_reflns_av_R_equivalents     0.0318
_diffrn_reflns_av_sigmaI/netI     0.0380
_diffrn_reflns_theta_min     3.22
_diffrn_reflns_theta_max     26.45
_diffrn_reflns_theta_full     26.45
_diffrn_measured_fraction_theta_max     0.972
_diffrn_measured_fraction_theta_full     0.972
_diffrn_reflns_limit_h_min     -31
_diffrn_reflns_limit_h_max     31
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     1881
_reflns_number_gt     965
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1058
_refine_ls_R_factor_gt     0.0507
_refine_ls_wR_factor_gt     0.1591
_refine_ls_wR_factor_ref     0.1800
_refine_ls_goodness_of_fit_ref     1.076
_refine_ls_restrained_S_all     1.075
_refine_ls_number_reflns     1881
_refine_ls_number_parameters     165
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
           'calc w=1/[σ²(Fo²)+(0.095P)²+0.002P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.292
_refine_diff_density_min     -0.335
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_extinction_coef     0.008(2)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
_computing_data_collection     'APEX2 (Bruker, 2005)'
_computing_cell_refinement     'SAINT (Siemens, 1996)'
_computing_data_reduction     'SAINT (Siemens, 1996)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Siemens, 1996)'
_computing_publication_material     'SHELXTL (Siemens, 1996)'
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_disorder_assembly
    _atom_site_disorder_group
    O O1 0.53257(9) 0.2530(4) 1.04684(18) 0.0733(7) Uani d . 1 . .
    H H1 0.5646 0.2449 1.0439 0.110 Uiso calc R 1 . .
    O O2 0.50729(11) 0.2165(5) 0.8602(2) 0.1059(10) Uani d . 1 . .
    O O3 0.29265(9) 0.1319(4) 0.63238(19) 0.0811(8) Uani d . 1 . .
    O O4 0.24250(9) 0.3056(4) 0.70420(19) 0.0803(8) Uani d . 1 . .
    O O5 0.30586(10) 0.3713(4) 1.11162(19) 0.0856(8) Uani d . 1 . .
    O O6 0.39304(11) 0.3002(4) 1.2188(2) 0.0978(9) Uani d . 1 . .
    O O7 0.63154(10) 0.2295(4) 0.0267(2) 0.0743(7) Uani d D 1 . .
    N N1 0.40250(8) 0.2104(4) 0.72988(17) 0.0512(6) Uani d . 1 . .
    H H1A 0.3902 0.0893 0.6978 0.077 Uiso calc R 1 . .
    H H1B 0.4402 0.2200 0.7480 0.077 Uiso calc R 1 . .
    H H1C 0.3846 0.3078 0.6787 0.077 Uiso calc R 1 . .
    N N2 0.35434(12) 0.3203(4) 1.1256(2) 0.0671(8) Uani d . 1 . .
    C C1 0.43519(11) 0.2456(4) 0.9352(2) 0.0526(7) Uani d . 1 . .
    C C2 0.39154(13) 0.2310(4) 0.8246(3) 0.0579(8) Uani d . 1 . .
    C C3 0.33520(12) 0.2444(4) 0.8198(2) 0.0548(8) Uani d . 1 . .
    C C4 0.32250(12) 0.2752(4) 0.9165(2) 0.0570(8) Uani d . 1 . .
    H H4A 0.2847 0.2900 0.9110 0.068 Uiso calc R 1 . .
    C C5 0.36690(13) 0.2835(4) 1.0216(2) 0.0543(7) Uani d . 1 . .
    C C6 0.42259(12) 0.2684(4) 1.0317(3) 0.0549(7) Uani d . 1 . .
    H H6 0.4520 0.2739 1.1058 0.066 Uiso calc R 1 . .
    C C7 0.49491(12) 0.2382(5) 0.9441(3) 0.0617(8) Uani d . 1 . .
    C C8 0.28710(11) 0.2269(4) 0.7107(2) 0.0442(7) Uani d . 1 . .
    H H7A 0.6655(11) 0.222(7) 0.077(3) 0.105(18) Uiso d D 1 . .
    H H7B 0.6325(18) 0.218(7) -0.0425(19) 0.101(18) Uiso d 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
    O1 0.0405(13) 0.1081(18) 0.0635(14) -0.0010(11) 0.0108(11) -0.0007(10)
    O2 0.0443(13) 0.214(3) 0.0611(15) 0.0020(14) 0.0221(12) 0.0004(15)
    O3 0.0511(13) 0.119(2) 0.0651(14) -0.0077(12) 0.0123(11) -0.0048(13)
    O4 0.0402(13) 0.126(2) 0.0684(14) 0.0065(11) 0.0126(11) 0.0054(12)
    O5 0.0617(16) 0.128(2) 0.0783(15) 0.0096(13) 0.0387(13) -0.0036(13)
    O6 0.0690(18) 0.171(3) 0.0483(14) 0.0109(15) 0.0165(13) -0.0057(14)
    O7 0.0417(13) 0.1032(19) 0.0696(16) 0.0009(11) 0.0112(12) 0.0034(13)
    N1 0.0270(11) 0.0904(17) 0.0363(12) -0.0005(10) 0.0119(9) -0.0018(10)
    N2 0.0597(18) 0.0849(19) 0.0620(17) 0.0006(14) 0.0288(15) -0.0031(13)
    C1 0.0363(15) 0.0686(19) 0.0512(17) -0.0007(12) 0.0142(13) 0.0003(12)
    C2 0.0461(17) 0.074(2) 0.0523(17) 0.0027(13) 0.0175(14) 0.0012(13)
    C3 0.0401(16) 0.073(2) 0.0498(16) 0.0001(12) 0.0150(13) 0.0044(13)
    C4 0.0448(17) 0.0675(19) 0.0594(18) 0.0024(12) 0.0204(15) 0.0051(13)
    C5 0.0513(17) 0.0668(18) 0.0483(16) 0.0012(13) 0.0228(14) -0.0009(12)
    C6 0.0382(15) 0.0675(19) 0.0538(17) -0.0005(12) 0.0113(13) -0.0022(13)
    C7 0.0409(16) 0.090(2) 0.0520(17) -0.0022(14) 0.0144(15) 0.0026(14)
    C8 0.0284(13) 0.0701(18) 0.0332(13) -0.0006(11) 0.0105(10) 0.0007(12)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C7 . 1.261(3) ?
    O1 H1 . 0.8200 ?
    O2 C7 . 1.186(3) ?
    O3 C8 . 1.194(3) ?
    O4 C8 . 1.209(3) ?
    O5 N2 . 1.211(3) ?
    O6 N2 . 1.196(3) ?
    O7 H7A . 0.845(19) ?
    O7 H7B . 0.859(19) ?
    N1 C2 . 1.293(3) ?
    N1 H1A . 0.8900 ?
    N1 H1B . 0.8900 ?
    N1 H1C . 0.8900 ?
    N2 C5 . 1.440(4) ?
    C1 C6 . 1.340(4) ?
    C1 C2 . 1.388(4) ?
    C1 C7 . 1.463(4) ?
    C2 C3 . 1.397(4) ?
    C3 C4 . 1.351(4) ?
    C3 C8 . 1.430(4) ?
    C4 C5 . 1.350(4) ?
    C4 H4A . 0.9300 ?
    C5 C6 . 1.361(4) ?
    C6 H6 . 0.9300 ?
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
    _geom_angle_publ_flag
    C7 O1 H1 . . 109.5 ?
    H7A O7 H7B . . 108(3) ?
    C2 N1 H1A . . 109.5 ?
    C2 N1 H1B . . 109.5 ?
    H1A N1 H1B . . 109.5 ?
    C2 N1 H1C . . 109.5 ?
    H1A N1 H1C . . 109.5 ?
    H1B N1 H1C . . 109.5 ?
    O6 N2 O5 . . 125.5(3) ?
    O6 N2 C5 . . 116.9(3) ?
    O5 N2 C5 . . 117.6(3) ?
    C6 C1 C2 . . 120.3(3) ?
    C6 C1 C7 . . 120.8(3) ?
    C2 C1 C7 . . 118.9(3) ?
    N1 C2 C1 . . 121.6(3) ?
    N1 C2 C3 . . 121.4(3) ?
    C1 C2 C3 . . 117.0(3) ?
    C4 C3 C2 . . 122.7(3) ?
    C4 C3 C8 . . 115.8(3) ?
    C2 C3 C8 . . 121.5(3) ?
    C5 C4 C3 . . 117.2(3) ?
    C5 C4 H4A . . 121.4 ?
    C3 C4 H4A . . 121.4 ?
    C4 C5 C6 . . 122.5(3) ?
    C4 C5 N2 . . 118.1(3) ?
    C6 C5 N2 . . 119.3(3) ?
    C1 C6 C5 . . 120.2(3) ?
    C1 C6 H6 . . 119.9 ?
    C5 C6 H6 . . 119.9 ?
    O2 C7 O1 . . 121.9(3) ?
    O2 C7 C1 . . 122.2(3) ?
    O1 C7 C1 . . 115.9(3) ?
    O3 C8 O4 . . 123.7(3) ?
    O3 C8 C3 . . 118.6(3) ?
    O4 C8 C3 . . 117.7(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
    _geom_hbond_publ_flag
    N1 H1B O2 . 0.89 1.73 2.514(3) 146 yes
    O7 H7B O3 2_655 0.859(19) 2.57(3) 3.254(4) 137(3) yes
    O7 H7B N1 2_655 0.859(19) 2.12(2) 2.927(4) 156(4) yes
    N1 H1C O6 6_565 0.89 2.62 3.225(3) 126 yes
    N1 H1C N2 6_565 0.89 2.57 3.384(3) 152 yes
    N1 H1C O7 2_655 0.89 2.44 2.927(4) 115 yes
    N1 H1B O2 2_656 0.89 2.19 2.866(4) 132 yes
    N1 H1A O6 6 0.89 2.57 3.365(3) 149 yes
    O1 H1 O7 1_556 0.82 1.77 2.592(4) 176 yes
data_global
_journal_date_recd_electronic     2007-09-27
_journal_date_accepted     2007-10-03
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue     11
_journal_page_first     o4267
_journal_page_last     o4267
_journal_paper_category     QO
_journal_coeditor_code     AT2415
_publ_contact_author_name     'T. Liu'
_publ_contact_author_address
;
      College of Engineering,
      Jinggangshan University,
      Jian 343009, People's Republic of China
;
_publ_contact_author_email     taoliu07@126.com
_publ_contact_author_fax     +86-796-8106067
_publ_contact_author_phone     +86-796-8106067
_publ_section_title
;
2-Ammonio-3-carboxy-5-nitrobenzoate monohydrate
;
loop_
    _publ_author_name
    _publ_author_address
    'T. Liu'
;
      College of Engineering,
      Jinggangshan University,
      Jian 343009, People's Republic of China
;
    'J. Y. Zhu'
;
      Department of Information Engineering,
      Jiangxi University of Science and Techology,
      Nanchang 330013, People's Republic of China
;
