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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     'from SHELXL-97 with Word-Perfect Macro PRPKAPPA'
_journal_date_recd_electronic     2005-02-22
_journal_date_accepted     2005-02-24
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2005
_journal_volume     61
_journal_issue      4
_journal_page_first     o246
_journal_page_last     o248
_journal_paper_category     FO
_publ_contact_author_name
;
Dr Christopher Glidewell
;
_publ_contact_author_address
;
University of St Andrews,
Fife KY16 9ST, Scotland
;
_publ_contact_author_email     cg@st-andrews.ac.uk
_publ_contact_author_fax     '+1334-463808'
_publ_contact_author_phone     '+1334-463839'
_publ_section_title
;
3-Iodoanilinium 2-carboxy-6-nitrobenzoate: a three-dimensional framework built
from O---H...O and N---H...O hydrogen bonds, and a two-centre iodo--nitro
interaction
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Glidewell, Christopher' .
;    School of Chemistry, University of St Andrews,
     Fife KY16 9ST, Scotland
;
    'Low, John N.' .
;     Department of Chemistry, University of Aberdeen,
      Meston Walk,
      Old Aberdeen AB24 3UE, Scotland
;
    'Skakle, Janet M. S.' .
;    Department of Chemistry, University of Aberdeen,
     Meston Walk,
     Old Aberdeen AB24 3UE, Scotland
;
    'Wardell, James L.' .
;    Instituto de Química, Departamento de Química Inorgânica,
     Universidade Federal do Rio de Janeiro,
     21945-970 Rio de Janeiro, RJ, Brazil
;
data_I
_chemical_name_systematic
;
3-Iodoanilinium 2-carboxy-6-nitrobenzoate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C6 H7 I N +, C8 H4 N O6 -'
_chemical_formula_sum     'C14 H11 I N2 O6'
_chemical_formula_iupac     'C6 H7 I N +, C8 H4 N O6 -'
_chemical_formula_weight     430.15
_chemical_melting_point     ?
_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     16.0068(10)
_cell_length_b     7.8616(5)
_cell_length_c     13.5718(9)
_cell_angle_alpha     90.00
_cell_angle_beta     113.3770(10)
_cell_angle_gamma     90.00
_cell_volume     1567.67(17)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3603
_cell_measurement_theta_min     2.77
_cell_measurement_theta_max     27.50
_cell_measurement_temperature     291(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.50
_exptl_crystal_size_mid     0.10
_exptl_crystal_size_min     0.08
_exptl_crystal_density_diffrn     1.823
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     840
_exptl_absorpt_coefficient_mu     2.075
_exptl_absorpt_correction_type     Multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2000)'
_exptl_absorpt_correction_T_min     0.424
_exptl_absorpt_correction_T_max     0.852
_exptl_special_details
;
?
;
_diffrn_ambient_temperature     291(2)
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed X-ray tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART 1000 CCD area-detector'
_diffrn_measurement_method     φ-ω
_diffrn_reflns_number     11173
_diffrn_reflns_av_R_equivalents     0.0365
_diffrn_reflns_av_sigmaI/netI     0.0372
_diffrn_reflns_theta_min     2.77
_diffrn_reflns_theta_max     27.50
_diffrn_reflns_theta_full     27.50
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     20
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     17
_diffrn_standards_decay_%     nil
_reflns_number_total     3603
_reflns_number_gt     2253
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0779
_refine_ls_R_factor_gt     0.0432
_refine_ls_wR_factor_gt     0.1022
_refine_ls_wR_factor_ref     0.1134
_refine_ls_goodness_of_fit_ref     0.948
_refine_ls_restrained_S_all     0.948
_refine_ls_number_reflns     3603
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                      'w=1/[σ²(Fo²)+(0.0656P)²] 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     0.891
_refine_diff_density_min     -0.948
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    'I' 'I' -0.4742 1.8119
                         '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     'SMART (Bruker, 1998)'
_computing_cell_refinement     'SAINT (Bruker, 2000)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'PLATON (Spek, 2003)'
_computing_publication_material     'SHELXL97 and PRPKAPPA (Ferguson, 1999)'
loop_
    _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
    _atom_site_type_symbol
    O11 0.4599(2) 1.1267(4) 0.5676(2) 0.0730(10) Uani d . 1 . . O
    O12 0.47858(18) 0.9237(3) 0.68785(18) 0.0444(6) Uani d . 1 . . O
    O21 0.37966(16) 0.5996(3) 0.70209(17) 0.0382(5) Uani d . 1 . . O
    O22 0.43485(16) 0.5855(3) 0.57526(18) 0.0383(5) Uani d . 1 . . O
    O31 0.2429(2) 0.4413(4) 0.5109(3) 0.0745(10) Uani d . 1 . . O
    O32 0.1067(2) 0.5267(5) 0.4370(4) 0.1004(14) Uani d . 1 . . O
    N31 0.1878(2) 0.5516(4) 0.4787(3) 0.0470(8) Uani d . 1 . . N
    C1 0.3376(2) 0.9371(4) 0.5372(3) 0.0336(7) Uani d . 1 . . C
    C2 0.3109(2) 0.7683(4) 0.5447(2) 0.0287(7) Uani d . 1 . . C
    C3 0.2203(2) 0.7291(4) 0.4839(3) 0.0347(8) Uani d . 1 . . C
    C4 0.1571(3) 0.8466(5) 0.4206(3) 0.0485(10) Uani d . 1 . . C
    C5 0.1859(3) 1.0100(5) 0.4148(3) 0.0528(10) Uani d . 1 . . C
    C6 0.2757(3) 1.0524(5) 0.4719(3) 0.0483(10) Uani d . 1 . . C
    C11 0.4318(3) 1.0030(5) 0.5986(3) 0.0408(8) Uani d . 1 . . C
    C21 0.3805(2) 0.6391(4) 0.6130(2) 0.0298(7) Uani d . 1 . . C
    I43 0.04980(2) 0.70440(6) 0.12973(2) 0.07919(18) Uani d . 1 . . I
    N41 0.41182(18) 0.6134(4) 0.3645(2) 0.0353(6) Uani d . 1 . . N
    C41 0.3258(2) 0.5310(4) 0.2994(2) 0.0349(8) Uani d . 1 . . C
    C42 0.2487(2) 0.6300(5) 0.2550(3) 0.0394(8) Uani d . 1 . . C
    C43 0.1665(3) 0.5514(6) 0.1956(3) 0.0522(11) Uani d . 1 . . C
    C44 0.1623(3) 0.3772(7) 0.1795(3) 0.0664(13) Uani d . 1 . . C
    C45 0.2406(4) 0.2826(6) 0.2226(4) 0.0673(14) Uani d . 1 . . C
    C46 0.3238(3) 0.3574(5) 0.2847(3) 0.0494(10) Uani d . 1 . . C
    H4 0.0966 0.8157 0.3829 0.058 Uiso calc R 1 . . H
    H5 0.1449 1.0910 0.3727 0.063 Uiso calc R 1 . . H
    H6 0.2950 1.1622 0.4662 0.058 Uiso calc R 1 . . H
    H12 0.5223 0.9822 0.7245 0.067 Uiso calc R 1 . . H
    H41A 0.4160 0.6247 0.4315 0.053 Uiso calc R 1 . . H
    H41B 0.4140 0.7156 0.3374 0.053 Uiso calc R 1 . . H
    H41C 0.4579 0.5502 0.3642 0.053 Uiso calc R 1 . . H
    H42 0.2517 0.7472 0.2649 0.047 Uiso calc R 1 . . H
    H44 0.1070 0.3248 0.1399 0.080 Uiso calc R 1 . . H
    H45 0.2381 0.1660 0.2102 0.081 Uiso calc R 1 . . H
    H46 0.3764 0.2922 0.3152 0.059 Uiso calc R 1 . . H
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 C6 . 1.376(5) no
    C1 C2 . 1.410(5) no
    C1 C11 . 1.496(5) no
    C11 O11 . 1.214(4) y
    C11 O12 . 1.302(4) y
    O12 H12 . 0.82 no
    C2 C3 . 1.388(5) no
    C2 C21 . 1.522(4) no
    C21 O21 . 1.253(4) y
    C21 O22 . 1.245(4) y
    C3 C4 . 1.388(5) no
    C3 N31 . 1.481(5) no
    N31 O31 . 1.190(4) no
    N31 O32 . 1.209(4) no
    C4 C5 . 1.377(6) no
    C4 H4 . 0.93 no
    C5 C6 . 1.376(6) no
    C5 H5 . 0.93 no
    C6 H6 . 0.93 no
    C41 C46 . 1.378(5) no
    C41 C42 . 1.380(5) no
    C41 N41 . 1.459(4) no
    N41 H41A . 0.89 no
    N41 H41B . 0.89 no
    N41 H41C . 0.89 no
    C42 C43 . 1.386(5) no
    C42 H42 . 0.93 no
    C43 C44 . 1.384(7) no
    C43 I43 . 2.099(4) no
    C44 C45 . 1.373(7) no
    C44 H44 . 0.93 no
    C45 C46 . 1.392(7) no
    C45 H45 . 0.93 no
    C46 H46 . 0.93 no
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
    C6 C1 C2 . . 120.3(3) no
    C6 C1 C11 . . 116.1(3) no
    C2 C1 C11 . . 123.6(3) no
    O11 C11 O12 . . 123.4(4) no
    O11 C11 C1 . . 120.9(3) no
    O12 C11 C1 . . 115.6(3) no
    C11 O12 H12 . . 109.5 no
    C3 C2 C1 . . 116.2(3) no
    C3 C2 C21 . . 123.6(3) no
    C1 C2 C21 . . 120.1(3) no
    O22 C21 O21 . . 126.2(3) no
    O22 C21 C2 . . 115.9(3) no
    O21 C21 C2 . . 117.9(3) no
    C4 C3 C2 . . 123.6(3) no
    C4 C3 N31 . . 116.2(3) no
    C2 C3 N31 . . 120.1(3) no
    O31 N31 O32 . . 123.8(4) no
    O31 N31 C3 . . 118.2(3) no
    O32 N31 C3 . . 117.8(3) no
    C5 C4 C3 . . 118.5(4) no
    C5 C4 H4 . . 120.7 no
    C3 C4 H4 . . 120.7 no
    C6 C5 C4 . . 119.5(3) no
    C6 C5 H5 . . 120.2 no
    C4 C5 H5 . . 120.2 no
    C1 C6 C5 . . 121.8(4) no
    C1 C6 H6 . . 119.1 no
    C5 C6 H6 . . 119.1 no
    C46 C41 C42 . . 122.0(3) no
    C46 C41 N41 . . 119.3(3) no
    C42 C41 N41 . . 118.7(3) no
    C41 N41 H41A . . 109.5 no
    C41 N41 H41B . . 109.5 no
    H41A N41 H41B . . 109.5 no
    C41 N41 H41C . . 109.5 no
    H41A N41 H41C . . 109.5 no
    H41B N41 H41C . . 109.5 no
    C41 C42 C43 . . 118.8(4) no
    C41 C42 H42 . . 120.6 no
    C43 C42 H42 . . 120.6 no
    C44 C43 C42 . . 120.5(4) no
    C44 C43 I43 . . 121.4(3) no
    C42 C43 I43 . . 118.1(3) no
    C45 C44 C43 . . 119.3(4) no
    C45 C44 H44 . . 120.3 no
    C43 C44 H44 . . 120.3 no
    C44 C45 C46 . . 121.4(4) no
    C44 C45 H45 . . 119.3 no
    C46 C45 H45 . . 119.3 no
    C41 C46 C45 . . 117.9(4) no
    C41 C46 H46 . . 121.1 no
    C45 C46 H46 . . 121.1 no
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 C11 O11 . . . . -23.6(5) no
    C2 C1 C11 O11 . . . . 157.3(4) y
    C6 C1 C11 O12 . . . . 153.6(3) no
    C2 C1 C11 O12 . . . . -25.5(5) no
    C6 C1 C2 C3 . . . . -0.4(5) no
    C11 C1 C2 C3 . . . . 178.7(3) no
    C6 C1 C2 C21 . . . . 177.3(3) no
    C11 C1 C2 C21 . . . . -3.7(5) no
    C3 C2 C21 O22 . . . . 103.3(4) no
    C1 C2 C21 O22 . . . . -74.1(4) no
    C3 C2 C21 O21 . . . . -78.3(4) no
    C1 C2 C21 O21 . . . . 104.2(4) y
    C1 C2 C3 C4 . . . . -1.7(5) no
    C21 C2 C3 C4 . . . . -179.2(3) no
    C1 C2 C3 N31 . . . . 174.4(3) no
    C21 C2 C3 N31 . . . . -3.1(5) no
    C4 C3 N31 O31 . . . . 163.0(4) no
    C2 C3 N31 O31 . . . . -13.4(5) y
    C4 C3 N31 O32 . . . . -13.3(5) no
    C2 C3 N31 O32 . . . . 170.3(4) no
    C2 C3 C4 C5 . . . . 2.1(6) no
    N31 C3 C4 C5 . . . . -174.2(3) no
    C3 C4 C5 C6 . . . . -0.3(6) no
    C2 C1 C6 C5 . . . . 2.0(6) no
    C11 C1 C6 C5 . . . . -177.1(4) no
    C4 C5 C6 C1 . . . . -1.7(6) no
    C46 C41 C42 C43 . . . . 1.2(5) no
    N41 C41 C42 C43 . . . . -178.3(3) no
    C41 C42 C43 C44 . . . . -1.1(5) no
    C41 C42 C43 I43 . . . . 179.6(2) no
    C42 C43 C44 C45 . . . . -0.3(6) no
    I43 C43 C44 C45 . . . . 178.9(3) no
    C43 C44 C45 C46 . . . . 1.8(7) no
    C42 C41 C46 C45 . . . . 0.2(6) no
    N41 C41 C46 C45 . . . . 179.7(3) no
    C44 C45 C46 C41 . . . . -1.7(7) no
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
    O12 H12 O21 4_667 0.82 1.75 2.570(3) 176 y
    N41 H41A O22 . 0.89 1.88 2.745(4) 164 y
    N41 H41B O21 2_564 0.89 2.23 3.052(4) 153 y
    N41 H41C O22 3_666 0.89 1.91 2.747(4) 156 y
