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###           Full Paper (Acta Crystallographica Section C)                ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, 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                #
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##############################################################################
data_global
_audit_creation_method     'WinGX routine CIF_UPDATE'
_audit_conform_dict_name     cif_core.dic
_audit_conform_dict_version     2.3
_journal_date_recd_electronic     2006-07-06
_journal_date_accepted     2006-08-07
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2006
_journal_volume     62
_journal_issue     10
_journal_page_first     o587
_journal_page_last     o589
_journal_paper_category     FO
_journal_coeditor_code     SF3013
_publ_contact_author_name     'Bruno, Giuseppe'
_publ_contact_author_address
;
Dipartimento di Chimica Inorganica, Chimica Analitica e Chimica Fisica
Universitá degli Studi di Messina
Via Salita Sperone 31
98166 Vill. S. Agata - Messina
Italy
;
_publ_contact_author_email     gbruno@unime.it
_publ_contact_author_fax      4E307(9)
_publ_contact_author_phone      4E307(9)
_publ_section_title
;
2,5-Dicarboxyanilinium chloride monohydrate
;
loop_
    _publ_author_name
    _publ_author_address
    'Bruno, Giuseppe'
;
Dipartimento di Chimica Inorganica, Chimica Analitica e Chimica Fisica
Universitá degli Studi di Messina
Via Salita Sperone 31
98166 Vill. S. Agata -- Messina
Italy
;
    'Rotondo, Archimede'
;
Dipartimento di Chimica Inorganica, Chimica Analitica e Chimica Fisica
Universitá degli Studi di Messina
Via Salita Sperone 31
98166 Vill. S. Agata -- Messina
Italy
;
    'Brancatelli, Giovanna'
;
Dipartimento di Chimica Inorganica, Chimica Analitica e Chimica Fisica
Universitá degli Studi di Messina
Via Salita Sperone 31
98166 Vill. S. Agata -- Messina
Italy
;
    'Nicoló, Francesco'
;
Dipartimento di Chimica Inorganica, Chimica Analitica e Chimica Fisica
Universitá degli Studi di Messina
Via Salita Sperone 31
98166 Vill. S. Agata -- Messina
Italy
;
    'Marino, Nadia'
;
Dipartimento di Chimica
Universitá della Calabria
Via P. Bucci 14/c
87036 Rende -- Cosenza
Italy
;
data_I
_audit_creation_method     'WinGX routine CIF_UPDATE'
_chemical_name_systematic
;
2,5-Dicarboxyanilinium chloride monohydrate
;
_chemical_name_common     '2-aminotherephtalic acid chlorohydrate and hydrate'
_chemical_formula_moiety     'C8 H8 N O4 + , Cl - , H2 O'
_chemical_formula_sum     'C8 H10 Cl N O5'
_chemical_formula_iupac     'C8 H8 N O4 + , Cl - , H2 O'
_chemical_formula_weight     235.62
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     6.5170(10)
_cell_length_b     16.670(3)
_cell_length_c     9.560(2)
_cell_angle_alpha     90
_cell_angle_beta     108.69(2)
_cell_angle_gamma     90
_cell_volume     983.8(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     30
_cell_measurement_theta_min     15
_cell_measurement_theta_max     30
_cell_measurement_temperature     298(2)
_exptl_crystal_description     irregular
_exptl_crystal_colour     'brown'
_exptl_crystal_size_max     0.40
_exptl_crystal_size_mid     0.19
_exptl_crystal_size_min     0.11
_exptl_crystal_density_diffrn     1.591
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     488
_exptl_absorpt_coefficient_mu     0.39
_exptl_absorpt_correction_type     psi-scan
_exptl_absorpt_process_details     '(North et al.,  1968)'
_exptl_absorpt_correction_T_min     0.860
_exptl_absorpt_correction_T_max     0.962
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker P3'
_diffrn_measurement_method     ω/2θ
_diffrn_reflns_number     2395
_diffrn_reflns_av_R_equivalents     0.0236
_diffrn_reflns_theta_min     2.44
_diffrn_reflns_theta_max     25.05
_diffrn_reflns_theta_full     25.05
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -1
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -1
_diffrn_reflns_limit_k_max     19
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     11
_diffrn_standards_number     1
_diffrn_standards_interval_count     50
_diffrn_standards_decay_%     0
_reflns_number_total     1741
_reflns_number_gt     1155
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_gt     0.0432
_refine_ls_wR_factor_ref     0.1171
_refine_ls_goodness_of_fit_ref     1.035
_refine_ls_restrained_S_all     1.035
_refine_ls_number_reflns     1743
_refine_ls_number_parameters     140
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0478P)²+0.3568P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max     0.008
_refine_diff_density_max     0.251
_refine_diff_density_min     -0.227
_refine_ls_extinction_method     none
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'
    Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'P3/V (Bruker, 1989)'
_computing_cell_refinement     P3/V
_computing_data_reduction     'XDISK (Bruker, 1989)'
_computing_structure_solution     'SIR2004 (Burla et al.,  2005)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'XP (Bruker, 1997)'
_computing_publication_material
;
PARST97 (Nardelli, 1995) and WinGX-PC (Version 1.6.4.05; Farrugia,
1999)
;
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
    C C1 0.6959(5) 0.89096(16) 0.1039(3) 0.0327(7) Uani d . 1 . .
    C C2 0.5401(5) 0.86214(15) 0.1624(3) 0.0310(7) Uani d . 1 . .
    C C3 0.4424(5) 0.91096(16) 0.2384(3) 0.0346(7) Uani d . 1 . .
    H H3 0.3387 0.8905 0.2765 0.042 Uiso calc R 1 . .
    C C4 0.5019(5) 0.99215(15) 0.2575(3) 0.0305(6) Uani d . 1 . .
    C C5 0.6607(5) 1.02127(17) 0.2045(3) 0.0382(7) Uani d . 1 . .
    H H5 0.7037 1.0746 0.2203 0.046 Uiso calc R 1 . .
    C C6 0.7557(5) 0.97153(16) 0.1283(3) 0.0352(7) Uani d . 1 . .
    H H6 0.8619 0.9919 0.0924 0.042 Uiso calc R 1 . .
    C C7 0.7865(5) 0.83905(18) 0.0116(3) 0.0360(7) Uani d . 1 . .
    N N8 0.4741(5) 0.77770(13) 0.1451(3) 0.0438(7) Uani d . 1 . .
    H H8A 0.3924 0.7671 0.2017 0.066 Uiso calc R 1 . .
    H H8B 0.5912 0.7466 0.172 0.066 Uiso calc R 1 . .
    H H8C 0.3985 0.7682 0.0511 0.066 Uiso calc R 1 . .
    C C9 0.3929(5) 1.04754(17) 0.3341(3) 0.0394(8) Uani d . 1 . .
    O O10 0.7172(4) 0.77266(12) -0.0302(2) 0.0493(6) Uani d . 1 . .
    O O11 0.9458(4) 0.87355(12) -0.0228(2) 0.0495(6) Uani d . 1 . .
    H H11 0.9902 0.8429 -0.0738 0.074 Uiso calc R 1 . .
    O O12 0.4395(4) 1.11797(12) 0.3518(3) 0.0622(7) Uani d . 1 . .
    O O13 0.2440(4) 1.01330(12) 0.3797(2) 0.0480(6) Uani d . 1 . .
    H H13 0.1896 1.0469 0.4197 0.072 Uiso calc R 1 . .
    O O14 0.9600(5) 0.61422(14) 0.0047(3) 0.0626(7) Uani d G 1 . .
    H H14A 1.0218 0.6244 -0.0702 0.094 Uiso d G 1 . .
    H H14B 0.8769 0.6604 0.0053 0.094 Uiso d G 1 . .
    Cl Cl1 0.13607(15) 0.74474(5) 0.31639(9) 0.0519(3) Uani 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
    C1 0.0379(18) 0.0301(15) 0.0314(14) 0.0011(14) 0.0129(13) 0.0000(11)
    C2 0.0431(19) 0.0210(13) 0.0311(14) 0.0013(14) 0.0150(14) -0.0001(11)
    C3 0.0444(19) 0.0295(15) 0.0346(15) -0.0033(14) 0.0194(14) 0.0010(12)
    C4 0.0382(17) 0.0253(13) 0.0288(13) 0.0040(13) 0.0120(13) 0.0003(11)
    C5 0.048(2) 0.0280(15) 0.0412(15) -0.0041(15) 0.0174(15) -0.0021(13)
    C6 0.0371(18) 0.0320(15) 0.0399(15) -0.0062(14) 0.0169(14) 0.0009(13)
    C7 0.0375(19) 0.0353(16) 0.0386(15) -0.0030(15) 0.0168(15) -0.0018(13)
    N8 0.0651(19) 0.0274(13) 0.0507(15) -0.0022(13) 0.0350(14) 0.0006(11)
    C9 0.050(2) 0.0305(16) 0.0383(16) 0.0051(16) 0.0149(16) -0.0001(13)
    O10 0.0560(15) 0.0422(13) 0.0621(14) -0.0081(12) 0.0362(12) -0.0141(11)
    O11 0.0524(16) 0.0457(13) 0.0649(14) -0.0088(12) 0.0390(13) -0.0113(11)
    O12 0.094(2) 0.0256(11) 0.0848(17) -0.0011(13) 0.0527(16) -0.0085(11)
    O13 0.0564(15) 0.0379(12) 0.0615(13) 0.0008(12) 0.0357(12) -0.0092(10)
    O14 0.074(2) 0.0506(14) 0.0774(17) -0.0058(14) 0.0451(15) 0.0108(12)
    Cl1 0.0633(6) 0.0487(5) 0.0570(5) -0.0027(5) 0.0380(5) 0.0060(4)
_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
    C1 C2 . 1.392(4) ?
    C1 C6 . 1.397(4) ?
    C1 C7 . 1.487(4) ?
    C2 C3 . 1.375(4) ?
    C2 N8 . 1.466(3) ?
    C3 C4 . 1.403(4) ?
    C3 H3 . 0.93 ?
    C4 C5 . 1.378(4) ?
    C4 C9 . 1.492(4) ?
    C5 C6 . 1.375(4) ?
    C5 H5 . 0.93 ?
    C6 H6 . 0.93 ?
    C7 O10 . 1.214(3) Yes
    C7 O11 . 1.318(3) Yes
    N8 H8A . 0.89 ?
    N8 H8B . 0.89 ?
    N8 H8C . 0.89 ?
    C9 O12 . 1.211(3) Yes
    C9 O13 . 1.315(4) Yes
    O11 H11 . 0.82 ?
    O13 H13 . 0.82 ?
    O14 H14A . 0.9419 ?
    O14 H14B . 0.9419 ?
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
    C2 C1 C6 . . 117.7(3) ?
    C2 C1 C7 . . 121.1(2) ?
    C6 C1 C7 . . 121.1(3) ?
    C3 C2 C1 . . 121.9(2) ?
    C3 C2 N8 . . 117.4(3) ?
    C1 C2 N8 . . 120.8(2) ?
    C2 C3 C4 . . 119.0(3) ?
    C2 C3 H3 . . 120.5 ?
    C4 C3 H3 . . 120.5 ?
    C5 C4 C3 . . 120.0(3) ?
    C5 C4 C9 . . 119.6(3) ?
    C3 C4 C9 . . 120.4(3) ?
    C6 C5 C4 . . 120.1(3) ?
    C6 C5 H5 . . 120 ?
    C4 C5 H5 . . 120 ?
    C5 C6 C1 . . 121.3(3) ?
    C5 C6 H6 . . 119.4 ?
    C1 C6 H6 . . 119.4 ?
    O10 C7 O11 . . 123.8(3) ?
    O10 C7 C1 . . 123.3(3) ?
    O11 C7 C1 . . 112.9(2) ?
    C2 N8 H8A . . 109.5 ?
    C2 N8 H8B . . 109.5 ?
    H8A N8 H8B . . 109.5 ?
    C2 N8 H8C . . 109.5 ?
    H8A N8 H8C . . 109.5 ?
    H8B N8 H8C . . 109.5 ?
    O12 C9 O13 . . 123.6(3) ?
    O12 C9 C4 . . 122.1(3) ?
    O13 C9 C4 . . 114.3(2) ?
    C7 O11 H11 . . 109.5 ?
    C9 O13 H13 . . 109.5 ?
    H14A O14 H14B . . 104.2 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C6 C1 C2 C3 . . . . 1.8(4) ?
    C7 C1 C2 C3 . . . . -174.9(3) ?
    C6 C1 C2 N8 . . . . -178.1(3) ?
    C7 C1 C2 N8 . . . . 5.2(4) ?
    C1 C2 C3 C4 . . . . 0.0(4) ?
    N8 C2 C3 C4 . . . . 179.9(3) ?
    C2 C3 C4 C5 . . . . -2.0(4) ?
    C2 C3 C4 C9 . . . . 177.5(3) ?
    C3 C4 C5 C6 . . . . 2.3(4) ?
    C9 C4 C5 C6 . . . . -177.2(3) ?
    C4 C5 C6 C1 . . . . -0.5(4) ?
    C2 C1 C6 C5 . . . . -1.5(4) ?
    C7 C1 C6 C5 . . . . 175.2(3) ?
    C2 C1 C7 O10 . . . . 7.5(5) Yes
    C6 C1 C7 O10 . . . . -169.0(3) Yes
    C2 C1 C7 O11 . . . . -174.1(3) Yes
    C6 C1 C7 O11 . . . . 9.4(4) Yes
    C5 C4 C9 O12 . . . . -0.1(4) Yes
    C3 C4 C9 O12 . . . . -179.7(3) Yes
    C5 C4 C9 O13 . . . . 179.9(3) Yes
    C3 C4 C9 O13 . . . . 0.3(4) Yes
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
    N8 H8A Cl1 . 0.89 2.3 3.186(3) 171.1
    N8 H8B O12 2_645 0.89 2.16 2.720(3) 120.4
    N8 H8C Cl1 4_575 0.89 2.35 3.229(3) 167.5
    O11 H11 Cl1 4_675 0.82 2.19 3.002(2) 172.7
    O13 H13 O14 2_655 0.82 1.78 2.600(3) 172.9
