##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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     'SHELXL97 (Sheldrick, 1997)'
_journal_date_recd_electronic     2008-01-02
_journal_date_accepted     2008-02-07
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2008
_journal_volume     64
_journal_issue      3
_journal_page_first     o180
_journal_page_last     o183
_journal_paper_category     FO
_journal_coeditor_code     GD3186
_publ_contact_author_name     'Dr Graham Smith'
_publ_contact_author_address
;
School of Physical and Chemical Sciences
Queensland University of Technology
GPO Box 2434
Brisbane 4001
Australia
;
_publ_contact_author_email     g.smith@qut.edu.au
_publ_contact_author_fax     '61 7 3864 1804'
_publ_contact_author_phone     '61 7 3864 2293'
_publ_section_title
;
One-dimensional hydrogen-bonded structures in the 1:1 proton-transfer compounds
of 4,5-dichlorophthalic acid with 8-hydroxyquinoline, 8-aminoquinoline and
quinoline-2-carboxylic acid (quinaldic acid)
;
loop_
    _publ_author_name
    _publ_author_address
    'Graham Smith'
;
School of Physical and Chemical Sciences
Queensland University of Technology
GPO Box 2434
Brisbane
Queensland 4001
Australia
;
    'Urs D. Wermuth'
;
School of Physical and Chemical Sciences
Queensland University of Technology
GPO Box 2434
Brisbane
Queensland 4001
Australia
;
    'Jonathan M. White'
;
BIO-21 Molecular Science and Biotechnology
University of Melbourne
Parkville
Victoria 3052
Australia
;
data_I
_audit_creation_method     'SHELXL97 (Sheldrick, 2008)'
_chemical_name_systematic
;
8-hydroxyquinolinium 2-carboxy-4,5-dichlorobenzoate
;
_chemical_name_common     '8-hydroxyquinolinium hydrogen 4,5-dichlorophthalate'
_chemical_formula_moiety     'C9 H8 N O + , C8 H3 Cl2 O4 -'
_chemical_formula_sum     'C17 H11 Cl2 N O5'
_chemical_formula_iupac     'C9 H8 N O + , C8 H3 Cl2 O4 -'
_chemical_formula_weight     380.17
_chemical_melting_point     499
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
_symmetry_space_group_name_Hall     'P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, y+1/2, -z+1/2'
_cell_length_a     6.8915(3)
_cell_length_b     7.2887(2)
_cell_length_c     30.8009(8)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1547.13(9)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3863
_cell_measurement_theta_min     4.3141
_cell_measurement_theta_max     73.3959
_cell_measurement_temperature     130(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     'pale yellow'
_exptl_crystal_size_max     0.614
_exptl_crystal_size_mid     0.560
_exptl_crystal_size_min     0.200
_exptl_crystal_density_diffrn     1.632
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     776
_exptl_absorpt_coefficient_mu     4.061
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.112
_exptl_absorpt_correction_T_max     0.443
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     130(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_source     'Enhance (Cu) X-ray source'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type
                             'Oxford Diffraction Xcalibur KM4 CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     16.0711
_diffrn_reflns_number     4879
_diffrn_reflns_av_R_equivalents     0.0354
_diffrn_reflns_av_sigmaI/netI     0.0215
_diffrn_reflns_theta_min     5.75
_diffrn_reflns_theta_max     73.44
_diffrn_reflns_theta_full     73.44
_diffrn_measured_fraction_theta_max     0.960
_diffrn_measured_fraction_theta_full     0.959
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -38
_diffrn_reflns_limit_l_max     36
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_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     2506
_reflns_number_gt     2437
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0363
_refine_ls_R_factor_gt     0.0357
_refine_ls_wR_factor_gt     0.0981
_refine_ls_wR_factor_ref     0.0985
_refine_ls_goodness_of_fit_ref     1.062
_refine_ls_restrained_S_all     1.062
_refine_ls_number_reflns     2506
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w = 1/[σ²(Fo²)+(0.078P)²+0.296P] 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     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.401
_refine_diff_density_min     -0.257
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0072(7)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details     'Flack (1983), with 662 Friedel pairs'
_refine_ls_abs_structure_Flack     0.035(15)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0181 0.0091
                         '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' 0.0311 0.0180
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0492 0.0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Cl' 'Cl' 0.3639 0.7018
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CrysAlis CCD (Oxford Diffraction, 2007)'
_computing_cell_refinement     'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_data_reduction     'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'PLATON (Spek, 2003)'
_computing_publication_material     'PLATON (Spek, 2003)'
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_thermal_displace_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    O O8A 0.6734(2) 0.5914(2) 0.82329(5) 0.0201(4) Uani . . 1.000
    N N1A 0.3513(3) 0.4331(3) 0.79128(6) 0.0172(5) Uani . . 1.000
    C C2A 0.1943(3) 0.3654(3) 0.77302(7) 0.0210(6) Uani . . 1.000
    C C3A 0.0382(3) 0.3079(3) 0.79842(8) 0.0233(6) Uani . . 1.000
    C C4A 0.0508(3) 0.3210(3) 0.84276(8) 0.0208(6) Uani . . 1.000
    C C5A 0.2455(3) 0.4051(3) 0.90836(7) 0.0210(6) Uani . . 1.000
    C C6A 0.4158(4) 0.4736(3) 0.92433(7) 0.0217(6) Uani . . 1.000
    C C7A 0.5656(3) 0.5351(3) 0.89713(7) 0.0192(6) Uani . . 1.000
    C C8A 0.5450(3) 0.5278(3) 0.85235(7) 0.0151(5) Uani . . 1.000
    C C9A 0.3719(3) 0.4502(3) 0.83541(7) 0.0155(5) Uani . . 1.000
    C C10A 0.2207(3) 0.3908(3) 0.86273(7) 0.0175(5) Uani . . 1.000
    Cl Cl4 0.67789(10) 0.41744(10) 0.49719(2) 0.0323(2) Uani . . 1.000
    Cl Cl5 0.28475(9) 0.59039(9) 0.53303(2) 0.0324(2) Uani . . 1.000
    O O11 0.3598(2) 0.5912(3) 0.69516(5) 0.0269(5) Uani . . 1.000
    O O12 0.6126(3) 0.4418(3) 0.72043(5) 0.0258(5) Uani . . 1.000
    O O21 0.9054(2) 0.3071(2) 0.69386(5) 0.0230(4) Uani . . 1.000
    O O22 1.0662(2) 0.2720(2) 0.63266(5) 0.0230(5) Uani . . 1.000
    C C1 0.5745(3) 0.4727(3) 0.64188(7) 0.0158(5) Uani . . 1.000
    C C2 0.7517(3) 0.3985(3) 0.62641(7) 0.0151(5) Uani . . 1.000
    C C3 0.7780(3) 0.3869(3) 0.58140(7) 0.0181(6) Uani . . 1.000
    C C4 0.6378(3) 0.4416(3) 0.55256(7) 0.0193(6) Uani . . 1.000
    C C5 0.4640(3) 0.5140(3) 0.56761(7) 0.0192(6) Uani . . 1.000
    C C6 0.4364(3) 0.5285(3) 0.61193(7) 0.0184(6) Uani . . 1.000
    C C11 0.5097(3) 0.5050(3) 0.68868(7) 0.0182(6) Uani . . 1.000
    C C21 0.9195(3) 0.3225(3) 0.65280(7) 0.0164(6) Uani . . 1.000
    H H1A 0.461(5) 0.473(5) 0.7755(10) 0.033(9) Uiso . . 1.000
    H H2A 0.18730 0.35580 0.74300 0.0250 Uiso calc R 1.000
    H H3A -0.07320 0.26120 0.78540 0.0280 Uiso calc R 1.000
    H H4A -0.05310 0.28380 0.85990 0.0250 Uiso calc R 1.000
    H H5A 0.14720 0.36840 0.92710 0.0250 Uiso calc R 1.000
    H H6A 0.43290 0.47950 0.95420 0.0260 Uiso calc R 1.000
    H H7A 0.67940 0.58110 0.90920 0.0230 Uiso calc R 1.000
    H H8A 0.758(6) 0.657(5) 0.8351(12) 0.046(10) Uiso . . 1.000
    H H3 0.89430 0.34070 0.57070 0.0220 Uiso calc R 1.000
    H H6 0.32040 0.57770 0.62210 0.0220 Uiso calc R 1.000
    H H12 0.725(6) 0.379(6) 0.7100(13) 0.041(12) Uiso . . 1.000
_geom_special_details
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Cl4 C4 . . 1.737(2) no
    Cl5 C5 . . 1.724(2) no
    O8A C8A . . 1.341(3) no
    O8A H8A . . 0.84(4) no
    O11 C11 . . 1.226(3) no
    O12 C11 . . 1.293(3) no
    O21 C21 . . 1.273(3) no
    O22 C21 . . 1.242(3) no
    O12 H12 . . 0.96(4) no
    N1A C2A . . 1.316(3) no
    N1A C9A . . 1.372(3) no
    N1A H1A . . 0.95(3) no
    C2A C3A . . 1.395(3) no
    C3A C4A . . 1.372(3) no
    C4A C10A . . 1.417(3) no
    C5A C10A . . 1.420(3) no
    C5A C6A . . 1.367(3) no
    C6A C7A . . 1.403(3) no
    C7A C8A . . 1.388(3) no
    C8A C9A . . 1.420(3) no
    C9A C10A . . 1.408(3) no
    C2A H2A . . 0.9300 no
    C3A H3A . . 0.9300 no
    C4A H4A . . 0.9300 no
    C5A H5A . . 0.9300 no
    C6A H6A . . 0.9300 no
    C7A H7A . . 0.9300 no
    C1 C2 . . 1.418(3) no
    C1 C11 . . 1.527(3) no
    C1 C6 . . 1.386(3) no
    C2 C21 . . 1.518(3) no
    C2 C3 . . 1.401(3) no
    C3 C4 . . 1.372(3) no
    C4 C5 . . 1.389(3) no
    C5 C6 . . 1.382(3) no
    C3 H3 . . 0.9300 no
    C6 H6 . . 0.9300 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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C8A O8A H8A . . . 112(3) no
    C11 O12 H12 . . . 111(2) no
    C2A N1A C9A . . . 122.9(2) no
    C2A N1A H1A . . . 123.6(19) no
    C9A N1A H1A . . . 114(2) no
    N1A C2A C3A . . . 120.5(2) no
    C2A C3A C4A . . . 119.3(2) no
    C3A C4A C10A . . . 120.6(2) no
    C6A C5A C10A . . . 119.1(2) no
    C5A C6A C7A . . . 122.2(2) no
    C6A C7A C8A . . . 120.4(2) no
    O8A C8A C9A . . . 116.54(19) no
    O8A C8A C7A . . . 125.63(19) no
    C7A C8A C9A . . . 117.81(19) no
    C8A C9A C10A . . . 121.7(2) no
    N1A C9A C10A . . . 119.18(19) no
    N1A C9A C8A . . . 119.16(19) no
    C5A C10A C9A . . . 118.70(19) no
    C4A C10A C5A . . . 123.8(2) no
    C4A C10A C9A . . . 117.6(2) no
    N1A C2A H2A . . . 120.00 no
    C3A C2A H2A . . . 120.00 no
    C2A C3A H3A . . . 120.00 no
    C4A C3A H3A . . . 120.00 no
    C10A C4A H4A . . . 120.00 no
    C3A C4A H4A . . . 120.00 no
    C6A C5A H5A . . . 120.00 no
    C10A C5A H5A . . . 120.00 no
    C7A C6A H6A . . . 119.00 no
    C5A C6A H6A . . . 119.00 no
    C8A C7A H7A . . . 120.00 no
    C6A C7A H7A . . . 120.00 no
    C2 C1 C11 . . . 128.88(19) no
    C2 C1 C6 . . . 118.7(2) no
    C6 C1 C11 . . . 112.46(18) no
    C1 C2 C21 . . . 127.97(19) no
    C1 C2 C3 . . . 117.84(19) no
    C3 C2 C21 . . . 114.16(18) no
    C2 C3 C4 . . . 122.2(2) no
    Cl4 C4 C5 . . . 120.24(16) no
    C3 C4 C5 . . . 120.1(2) no
    Cl4 C4 C3 . . . 119.63(16) no
    C4 C5 C6 . . . 118.52(19) no
    Cl5 C5 C4 . . . 122.33(17) no
    Cl5 C5 C6 . . . 119.14(16) no
    C1 C6 C5 . . . 122.7(2) no
    O11 C11 C1 . . . 118.63(19) no
    O12 C11 C1 . . . 119.91(19) no
    O11 C11 O12 . . . 121.5(2) no
    O22 C21 C2 . . . 117.44(19) no
    O21 C21 O22 . . . 122.15(19) no
    O21 C21 C2 . . . 120.38(18) no
    C2 C3 H3 . . . 119.00 no
    C4 C3 H3 . . . 119.00 no
    C1 C6 H6 . . . 119.00 no
    C5 C6 H6 . . . 119.00 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
    C9A N1A C2A C3A . . . . 0.4(3) no
    C2A N1A C9A C8A . . . . -178.9(2) no
    C2A N1A C9A C10A . . . . 1.0(3) no
    N1A C2A C3A C4A . . . . -0.6(3) no
    C2A C3A C4A C10A . . . . -0.5(3) no
    C3A C4A C10A C5A . . . . -178.8(2) no
    C3A C4A C10A C9A . . . . 1.7(3) no
    C10A C5A C6A C7A . . . . 1.7(3) no
    C6A C5A C10A C4A . . . . 179.7(2) no
    C6A C5A C10A C9A . . . . -0.9(3) no
    C5A C6A C7A C8A . . . . -0.1(3) no
    C6A C7A C8A O8A . . . . 176.2(2) no
    C6A C7A C8A C9A . . . . -2.4(3) no
    O8A C8A C9A N1A . . . . 4.4(3) no
    O8A C8A C9A C10A . . . . -175.46(19) no
    C7A C8A C9A N1A . . . . -176.9(2) no
    C7A C8A C9A C10A . . . . 3.2(3) no
    N1A C9A C10A C4A . . . . -2.0(3) no
    N1A C9A C10A C5A . . . . 178.5(2) no
    C8A C9A C10A C4A . . . . 177.9(2) no
    C8A C9A C10A C5A . . . . -1.7(3) no
    C6 C1 C2 C3 . . . . 0.5(3) no
    C6 C1 C2 C21 . . . . -177.5(2) no
    C11 C1 C2 C3 . . . . -178.5(2) no
    C11 C1 C2 C21 . . . . 3.5(4) no
    C2 C1 C6 C5 . . . . 0.3(3) no
    C11 C1 C6 C5 . . . . 179.4(2) no
    C2 C1 C11 O11 . . . . 171.3(2) no
    C2 C1 C11 O12 . . . . -8.7(4) no
    C6 C1 C11 O11 . . . . -7.7(3) no
    C6 C1 C11 O12 . . . . 172.3(2) no
    C1 C2 C3 C4 . . . . -1.1(3) no
    C21 C2 C3 C4 . . . . 177.1(2) no
    C1 C2 C21 O21 . . . . 5.5(3) no
    C1 C2 C21 O22 . . . . -176.6(2) no
    C3 C2 C21 O21 . . . . -172.6(2) no
    C3 C2 C21 O22 . . . . 5.4(3) no
    C2 C3 C4 Cl4 . . . . -178.26(17) no
    C2 C3 C4 C5 . . . . 1.0(3) no
    Cl4 C4 C5 Cl5 . . . . -2.4(3) no
    Cl4 C4 C5 C6 . . . . 179.04(17) no
    C3 C4 C5 Cl5 . . . . 178.36(17) no
    C3 C4 C5 C6 . . . . -0.3(3) no
    Cl5 C5 C6 C1 . . . . -179.07(17) no
    C4 C5 C6 C1 . . . . -0.4(3) 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
    N1A H1A O8A . 0.95(3) 2.25(3) 2.689(3) 108(2) no
    N1A H1A O12 . 0.95(3) 2.01(3) 2.830(3) 145(3) yes
    O8A H8A O22 4_756 0.84(4) 1.78(4) 2.607(2) 171(4) yes
    O12 H12 O21 . 0.96(4) 1.44(4) 2.389(2) 173(4) yes
    C2A H2A O11 . 0.93 2.56 3.124(3) 120 no
    C2A H2A O21 1_455 0.93 2.49 3.176(3) 131 no
    C3 H3 O22 . 0.93 2.30 2.672(3) 103 no
    C3A H3A O11 4_546 0.93 2.41 3.171(3) 139 no
    C6 H6 O11 . 0.93 2.27 2.657(3) 104 no
    C7A H7A O22 4_756 0.93 2.58 3.203(3) 125 no
data_II
_audit_creation_method     'SHELXL97 (Sheldrick, 2008)'
_chemical_name_systematic
;
8-aminoquinolinium 2-carboxy-4,5-dichlorobenzoate
;
_chemical_name_common     '8-aminoquinolinium hydrogen 4,5-dichlorophthalate'
_chemical_formula_moiety     'C9 H9 N2 + , C8 H3 Cl2 O4 -'
_chemical_formula_sum     'C17 H12 Cl2 N2 O4'
_chemical_formula_iupac     'C9 H9 N2 + , C8 H3 Cl2 O4 -'
_chemical_formula_weight     379.19
_chemical_melting_point     471
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
_symmetry_space_group_name_Hall     'P 2ac 2ab'
loop_
    _symmetry_equiv_pos_site_id
    _symmetry_equiv_pos_as_xyz
    1 x,y,z
    2 1/2-x,-y,1/2+z
    3 1/2+x,1/2-y,-z
    4 -x,1/2+y,1/2-z
_cell_length_a     7.2003(6)
_cell_length_b     7.3039(6)
_cell_length_c     29.438(3)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1548.2(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5985
_cell_measurement_theta_min     2.77
_cell_measurement_theta_max     27.54
_cell_measurement_temperature     130(2)
_exptl_crystal_description     'cut plate'
_exptl_crystal_colour     'pale brown'
_exptl_crystal_size_max     0.45
_exptl_crystal_size_mid     0.40
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.627
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     776
_exptl_absorpt_coefficient_mu     0.447
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.842
_exptl_absorpt_correction_T_max     0.956
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     130(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9645
_diffrn_reflns_av_R_equivalents     0.0221
_diffrn_reflns_av_sigmaI/netI     0.0262
_diffrn_reflns_theta_min     1.38
_diffrn_reflns_theta_max     27.57
_diffrn_reflns_theta_full     27.57
_diffrn_measured_fraction_theta_max     0.993
_diffrn_measured_fraction_theta_full     0.993
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     4
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -37
_diffrn_reflns_limit_l_max     38
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0.0
_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     3529
_reflns_number_gt     3425
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0301
_refine_ls_R_factor_gt     0.0290
_refine_ls_wR_factor_gt     0.0726
_refine_ls_wR_factor_ref     0.0732
_refine_ls_goodness_of_fit_ref     1.075
_refine_ls_restrained_S_all     1.075
_refine_ls_number_reflns     3529
_refine_ls_number_parameters     242
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0415P)²+0.3288P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.313
_refine_diff_density_min     -0.218
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details
                                    'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack     0.04(5)
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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 2000)'
_computing_cell_refinement     'SMART (Bruker, 2000)'
_computing_data_reduction     'SAINT (Bruker, 1999)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'PLATON (Spek, 2003)'
_computing_publication_material     'PLATON (Spek, 2003)'
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_thermal_displace_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    N N1A 0.30022(19) 0.4127(2) 0.79305(5) 0.0177(3) Uani . . 1.000
    N N8A 0.6450(2) 0.5704(2) 0.81739(5) 0.0201(4) Uani . . 1.000
    C C2A 0.1402(2) 0.3402(2) 0.77963(6) 0.0222(5) Uani . . 1.000
    C C3A 0.0133(2) 0.2717(2) 0.81111(7) 0.0232(5) Uani . . 1.000
    C C4A 0.0552(2) 0.2849(2) 0.85632(6) 0.0218(5) Uani . . 1.000
    C C5A 0.2733(2) 0.3763(2) 0.91764(6) 0.0201(5) Uani . . 1.000
    C C6A 0.4420(2) 0.4512(2) 0.92918(5) 0.0208(5) Uani . . 1.000
    C C7A 0.5679(2) 0.5105(2) 0.89594(6) 0.0186(4) Uani . . 1.000
    C C8A 0.5286(2) 0.4997(2) 0.84991(6) 0.0168(4) Uani . . 1.000
    C C9A 0.3525(2) 0.4239(2) 0.83767(5) 0.0161(4) Uani . . 1.000
    C C10A 0.2259(2) 0.3606(2) 0.87131(6) 0.0177(4) Uani . . 1.000
    Cl Cl4 0.60192(6) 0.42315(7) 0.492190(10)
                                            0.02750(10)
                                                      Uani . . 1.000
    Cl Cl5 0.24836(6) 0.57856(6) 0.543970(10)
                                            0.02570(10)
                                                      Uani . . 1.000
    O O11 0.41286(18) 0.53291(17) 0.71080(4) 0.0240(3) Uani . . 1.000
    O O12 0.67963(18) 0.39657(19) 0.72501(4) 0.0273(4) Uani . . 1.000
    O O21 0.94065(18) 0.26731(18) 0.68629(4) 0.0254(4) Uani . . 1.000
    O O22 1.05293(18) 0.2509(2) 0.61728(5) 0.0309(4) Uani . . 1.000
    C C1 0.5875(2) 0.4385(2) 0.64629(5) 0.0161(4) Uani . . 1.000
    C C2 0.7469(2) 0.37106(19) 0.62314(5) 0.0157(4) Uani . . 1.000
    C C3 0.7462(2) 0.3702(2) 0.57580(6) 0.0175(4) Uani . . 1.000
    C C4 0.5946(2) 0.4311(2) 0.55079(5) 0.0174(4) Uani . . 1.000
    C C5 0.4386(2) 0.4959(2) 0.57347(6) 0.0181(4) Uani . . 1.000
    C C6 0.4368(2) 0.4990(2) 0.62025(5) 0.0182(4) Uani . . 1.000
    C C11 0.5566(2) 0.4572(2) 0.69732(5) 0.0198(4) Uani . . 1.000
    C C21 0.9274(2) 0.2923(2) 0.64275(6) 0.0187(4) Uani . . 1.000
    H H1A 0.366(3) 0.466(3) 0.7723(8) 0.030(6) Uiso . . 1.000
    H H2A 0.11170 0.33500 0.74810 0.0270 Uiso calc R 1.000
    H H3A -0.09970 0.21710 0.80140 0.0280 Uiso calc R 1.000
    H H4A -0.03190 0.24230 0.87810 0.0260 Uiso calc R 1.000
    H H5A 0.18990 0.33560 0.94050 0.0240 Uiso calc R 1.000
    H H6A 0.47390 0.46310 0.96030 0.0250 Uiso calc R 1.000
    H H7A 0.68400 0.55960 0.90530 0.0220 Uiso calc R 1.000
    H H81A 0.648(4) 0.524(3) 0.7928(8) 0.036(7) Uiso . . 1.000
    H H82A 0.748(3) 0.615(3) 0.8268(7) 0.024(5) Uiso . . 1.000
    H H3 0.85270 0.32660 0.56010 0.0220 Uiso calc R 1.000
    H H6 0.32940 0.54360 0.63540 0.0210 Uiso calc R 1.000
    H H21 0.827(5) 0.315(4) 0.7022(9) 0.058(8) Uiso . . 1.000
_geom_special_details
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Cl4 C4 . . 1.7269(15) no
    Cl5 C5 . . 1.7306(16) no
    O11 C11 . . 1.2387(19) no
    O12 C11 . . 1.2827(19) no
    O21 C21 . . 1.298(2) no
    O22 C21 . . 1.213(2) no
    O21 H21 . . 1.01(3) no
    N1A C2A . . 1.328(2) no
    N1A C9A . . 1.369(2) no
    N8A C8A . . 1.373(2) no
    N1A H1A . . 0.87(2) no
    N8A H81A . . 0.80(2) no
    N8A H82A . . 0.86(2) no
    C2A C3A . . 1.394(2) no
    C3A C4A . . 1.368(3) no
    C4A C10A . . 1.418(2) no
    C5A C6A . . 1.375(2) no
    C5A C10A . . 1.411(2) no
    C6A C7A . . 1.403(2) no
    C7A C8A . . 1.387(2) no
    C8A C9A . . 1.430(2) no
    C9A C10A . . 1.423(2) no
    C2A H2A . . 0.9500 no
    C3A H3A . . 0.9500 no
    C4A H4A . . 0.9500 no
    C5A H5A . . 0.9500 no
    C6A H6A . . 0.9500 no
    C7A H7A . . 0.9500 no
    C1 C2 . . 1.423(2) no
    C1 C11 . . 1.525(2) no
    C1 C6 . . 1.400(2) no
    C2 C21 . . 1.534(2) no
    C2 C3 . . 1.394(2) no
    C3 C4 . . 1.390(2) no
    C4 C5 . . 1.390(2) no
    C5 C6 . . 1.377(2) no
    C3 H3 . . 0.9500 no
    C6 H6 . . 0.9500 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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C21 O21 H21 . . . 110.6(16) no
    C2A N1A C9A . . . 123.22(14) no
    C9A N1A H1A . . . 120.0(15) no
    C2A N1A H1A . . . 116.4(15) no
    C8A N8A H81A . . . 119.2(18) no
    C8A N8A H82A . . . 116.5(14) no
    H81A N8A H82A . . . 116(2) no
    N1A C2A C3A . . . 120.92(16) no
    C2A C3A C4A . . . 118.48(14) no
    C3A C4A C10A . . . 121.42(15) no
    C6A C5A C10A . . . 119.01(14) no
    C5A C6A C7A . . . 121.44(14) no
    C6A C7A C8A . . . 122.17(14) no
    N8A C8A C9A . . . 120.75(15) no
    N8A C8A C7A . . . 122.37(14) no
    C7A C8A C9A . . . 116.70(14) no
    N1A C9A C8A . . . 120.59(14) no
    N1A C9A C10A . . . 118.18(13) no
    C8A C9A C10A . . . 121.23(14) no
    C4A C10A C9A . . . 117.73(15) no
    C5A C10A C9A . . . 119.43(13) no
    C4A C10A C5A . . . 122.84(15) no
    N1A C2A H2A . . . 120.00 no
    C3A C2A H2A . . . 120.00 no
    C2A C3A H3A . . . 121.00 no
    C4A C3A H3A . . . 121.00 no
    C10A C4A H4A . . . 119.00 no
    C3A C4A H4A . . . 119.00 no
    C6A C5A H5A . . . 121.00 no
    C10A C5A H5A . . . 120.00 no
    C7A C6A H6A . . . 119.00 no
    C5A C6A H6A . . . 119.00 no
    C8A C7A H7A . . . 119.00 no
    C6A C7A H7A . . . 119.00 no
    C2 C1 C11 . . . 128.36(13) no
    C2 C1 C6 . . . 118.18(13) no
    C6 C1 C11 . . . 113.46(12) no
    C1 C2 C21 . . . 129.27(14) no
    C1 C2 C3 . . . 118.53(13) no
    C3 C2 C21 . . . 112.19(13) no
    C2 C3 C4 . . . 122.08(14) no
    Cl4 C4 C5 . . . 121.07(12) no
    C3 C4 C5 . . . 119.30(14) no
    Cl4 C4 C3 . . . 119.64(12) no
    C4 C5 C6 . . . 119.57(14) no
    Cl5 C5 C4 . . . 121.16(13) no
    Cl5 C5 C6 . . . 119.24(12) no
    C1 C6 C5 . . . 122.34(13) no
    O11 C11 C1 . . . 118.52(13) no
    O12 C11 C1 . . . 119.63(13) no
    O11 C11 O12 . . . 121.84(14) no
    O22 C21 C2 . . . 119.49(15) no
    O21 C21 O22 . . . 121.37(15) no
    O21 C21 C2 . . . 119.11(13) no
    C2 C3 H3 . . . 119.00 no
    C4 C3 H3 . . . 119.00 no
    C1 C6 H6 . . . 119.00 no
    C5 C6 H6 . . . 119.00 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
    C9A N1A C2A C3A . . . . 0.7(2) no
    C2A N1A C9A C8A . . . . 178.55(14) no
    C2A N1A C9A C10A . . . . -2.3(2) no
    N1A C2A C3A C4A . . . . 1.6(2) no
    C2A C3A C4A C10A . . . . -2.1(2) no
    C3A C4A C10A C5A . . . . 179.95(14) no
    C3A C4A C10A C9A . . . . 0.4(2) no
    C10A C5A C6A C7A . . . . -0.6(2) no
    C6A C5A C10A C4A . . . . 179.90(14) no
    C6A C5A C10A C9A . . . . -0.6(2) no
    C5A C6A C7A C8A . . . . 1.0(2) no
    C6A C7A C8A N8A . . . . 174.84(14) no
    C6A C7A C8A C9A . . . . -0.3(2) no
    N8A C8A C9A N1A . . . . 3.0(2) no
    N8A C8A C9A C10A . . . . -176.07(14) no
    C7A C8A C9A N1A . . . . 178.21(14) no
    C7A C8A C9A C10A . . . . -0.9(2) no
    N1A C9A C10A C4A . . . . 1.8(2) no
    N1A C9A C10A C5A . . . . -177.81(14) no
    C8A C9A C10A C4A . . . . -179.13(14) no
    C8A C9A C10A C5A . . . . 1.3(2) no
    C6 C1 C2 C3 . . . . 0.7(2) no
    C6 C1 C2 C21 . . . . -178.21(14) no
    C11 C1 C2 C3 . . . . -178.55(14) no
    C11 C1 C2 C21 . . . . 2.6(2) no
    C2 C1 C6 C5 . . . . -0.3(2) no
    C11 C1 C6 C5 . . . . 179.05(13) no
    C2 C1 C11 O11 . . . . 174.38(15) no
    C2 C1 C11 O12 . . . . -4.9(2) no
    C6 C1 C11 O11 . . . . -4.9(2) no
    C6 C1 C11 O12 . . . . 175.87(14) no
    C1 C2 C3 C4 . . . . -0.7(2) no
    C21 C2 C3 C4 . . . . 178.36(13) no
    C1 C2 C21 O21 . . . . 5.8(2) no
    C1 C2 C21 O22 . . . . -175.88(15) no
    C3 C2 C21 O21 . . . . -173.16(14) no
    C3 C2 C21 O22 . . . . 5.2(2) no
    C2 C3 C4 Cl4 . . . . -179.08(12) no
    C2 C3 C4 C5 . . . . 0.3(2) no
    Cl4 C4 C5 Cl5 . . . . -2.23(18) no
    Cl4 C4 C5 C6 . . . . 179.48(11) no
    C3 C4 C5 Cl5 . . . . 178.39(11) no
    C3 C4 C5 C6 . . . . 0.1(2) no
    Cl5 C5 C6 C1 . . . . -178.44(12) no
    C4 C5 C6 C1 . . . . -0.1(2) 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
    O21 H12 O12 . 1.01(3) 1.39(3) 2.3922(18) 174(3) yes
    N1A H1A O11 . 0.87(2) 1.91(2) 2.7002(19) 152(2) yes
    N8A H81A O12 . 0.80(2) 2.21(2) 3.0116(19) 176(3) yes
    N8A H82A O21 4_756 0.86(2) 2.53(2) 3.314(2) 152.2(18) yes
    N8A H82A O22 4_756 0.86(2) 2.40(2) 3.189(2) 153.8(18) yes
    C2A H2A O21 1_455 0.9500 2.2500 3.146(2) 156.00 no
    C3 H3 O22 . 0.9500 2.2800 2.670(2) 103.00 no
    C6 H6 O11 . 0.9500 2.3000 2.6826(19) 103.00 no
    C7A H7A O22 4_756 0.9500 2.4500 3.269(2) 145.00 no
data_III
_audit_creation_method     'SHELXL97 (Sheldrick, 2008)'
_chemical_name_systematic
;
2-carboxyquinolinium 2-carboxy-4,5-dichlorobenzoate quinolinium
2-carboxylate monohydrate
;
_chemical_name_common
;
2-carboxyquinolinium hydrogen 4,5-dichlorophthalate quinaldic
acid monohydrate
;
_chemical_formula_moiety
                           'C10 H8 N O2 + , C8 H3 Cl2 O4 - , C10 H7 N O2 , H2 O'
_chemical_formula_sum     'C28 H20 Cl2 N2 O9'
_chemical_formula_iupac
                           'C10 H8 N O2 + , C8 H3 Cl2 O4 - , C10 H7 N O2 , H2 O'
_chemical_formula_weight     599.36
_chemical_melting_point     455
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     7.1893(9)
_cell_length_b     10.1172(13)
_cell_length_c     19.520(3)
_cell_angle_alpha     87.558(2)
_cell_angle_beta     88.577(2)
_cell_angle_gamma     83.996(2)
_cell_volume     1410.4(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2565
_cell_measurement_theta_min     3
_cell_measurement_theta_max     25
_cell_measurement_temperature     130(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.40
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.25
_exptl_crystal_density_diffrn     1.407
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     616
_exptl_absorpt_coefficient_mu     0.287
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.865
_exptl_absorpt_correction_T_max     0.931
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     130(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6939
_diffrn_reflns_av_R_equivalents     0.0939
_diffrn_reflns_av_sigmaI/netI     0.0708
_diffrn_reflns_theta_min     1.04
_diffrn_reflns_theta_max     24.99
_diffrn_reflns_theta_full     24.99
_diffrn_measured_fraction_theta_max     0.981
_diffrn_measured_fraction_theta_full     0.981
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     23
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_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     4878
_reflns_number_gt     3980
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0668
_refine_ls_R_factor_gt     0.0587
_refine_ls_wR_factor_gt     0.1538
_refine_ls_wR_factor_ref     0.1600
_refine_ls_goodness_of_fit_ref     1.026
_refine_ls_restrained_S_all     1.026
_refine_ls_number_reflns     4878
_refine_ls_number_parameters     390
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
               'calc w = 1/[σ²(Fo²)+(0.1022P)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     0.002
_refine_ls_shift/su_mean     0.001
_refine_diff_density_max     0.667
_refine_diff_density_min     -0.513
_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'
    '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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 2000)'
_computing_cell_refinement     'SMART (Bruker, 2000)'
_computing_data_reduction     'SAINT (Bruker, 1999)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'PLATON (Spek, 2003)'
_computing_publication_material     'PLATON (Spek, 2003)'
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_thermal_displace_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    O O21A 0.6202(3) -0.26013(17) 0.38453(8) 0.0313(6) Uani . . 1.000
    O O22A 0.6907(3) -0.05882(17) 0.41323(9) 0.0328(6) Uani . . 1.000
    N N1A 0.6843(3) -0.1319(2) 0.54646(10) 0.0237(6) Uani . . 1.000
    C C2A 0.6535(3) -0.2210(2) 0.50092(12) 0.0227(7) Uani . . 1.000
    C C3A 0.6174(4) -0.3493(2) 0.52295(13) 0.0260(8) Uani . . 1.000
    C C4A 0.6132(4) -0.3814(3) 0.59198(13) 0.0276(8) Uani . . 1.000
    C C5A 0.6397(4) -0.3142(3) 0.71237(13) 0.0312(8) Uani . . 1.000
    C C6A 0.6690(4) -0.2180(3) 0.75589(13) 0.0320(8) Uani . . 1.000
    C C7A 0.7045(4) -0.0909(3) 0.73113(13) 0.0323(8) Uani . . 1.000
    C C8A 0.7106(4) -0.0590(3) 0.66192(13) 0.0297(8) Uani . . 1.000
    C C9A 0.6807(3) -0.1583(3) 0.61645(12) 0.0249(8) Uani . . 1.000
    C C10A 0.6436(3) -0.2872(3) 0.64041(12) 0.0250(8) Uani . . 1.000
    C C21A 0.6560(4) -0.1747(2) 0.42600(12) 0.0248(8) Uani . . 1.000
    O O21B 0.8848(3) 0.3200(2) 0.55248(9) 0.0436(7) Uani . . 1.000
    O O22B 0.7896(3) 0.12477(19) 0.52688(9) 0.0369(7) Uani . . 1.000
    N N1B 0.8280(3) 0.1844(2) 0.39254(10) 0.0244(7) Uani . . 1.000
    C C2B 0.8547(3) 0.2770(3) 0.43689(12) 0.0256(8) Uani . . 1.000
    C C3B 0.8867(4) 0.4046(3) 0.41316(13) 0.0294(8) Uani . . 1.000
    C C4B 0.8820(4) 0.4360(3) 0.34454(13) 0.0302(8) Uani . . 1.000
    C C5B 0.8531(4) 0.3625(3) 0.22533(13) 0.0309(8) Uani . . 1.000
    C C6B 0.8292(4) 0.2637(3) 0.18274(13) 0.0305(8) Uani . . 1.000
    C C7B 0.8055(4) 0.1340(3) 0.20960(13) 0.0288(8) Uani . . 1.000
    C C8B 0.8058(4) 0.1057(2) 0.27853(13) 0.0272(8) Uani . . 1.000
    C C9B 0.8297(3) 0.2075(2) 0.32263(12) 0.0241(8) Uani . . 1.000
    C C10B 0.8553(3) 0.3381(2) 0.29723(13) 0.0254(8) Uani . . 1.000
    C C21B 0.8426(4) 0.2353(3) 0.51320(13) 0.0282(8) Uani . . 1.000
    Cl Cl4 0.59274(10) 0.16384(7) 1.03271(3) 0.0350(2) Uani . . 1.000
    Cl Cl5 0.17722(10) 0.11042(7) 1.07312(3) 0.0347(2) Uani . . 1.000
    O O11 0.0013(3) 0.32387(18) 0.77895(10) 0.0330(6) Uani . . 1.000
    O O12 -0.1359(3) 0.15182(18) 0.82527(9) 0.0327(6) Uani . . 1.000
    O O21 0.3468(3) 0.17710(18) 0.73890(9) 0.0350(6) Uani . . 1.000
    O O22 0.4659(3) 0.36120(17) 0.76824(9) 0.0307(6) Uani . . 1.000
    C C1 0.1439(4) 0.2071(2) 0.87320(12) 0.0235(7) Uani . . 1.000
    C C2 0.3284(4) 0.2281(2) 0.85538(12) 0.0239(7) Uani . . 1.000
    C C3 0.4653(4) 0.2136(2) 0.90452(13) 0.0279(8) Uani . . 1.000
    C C4 0.4187(4) 0.1793(2) 0.97204(12) 0.0271(8) Uani . . 1.000
    C C5 0.2378(4) 0.1581(2) 0.98994(12) 0.0261(8) Uani . . 1.000
    C C6 0.1002(4) 0.1717(2) 0.94129(12) 0.0251(8) Uani . . 1.000
    C C11 -0.0116(4) 0.2228(2) 0.82307(12) 0.0239(7) Uani . . 1.000
    C C21 0.3865(3) 0.2625(2) 0.78261(12) 0.0242(8) Uani . . 1.000
    O O1W 0.7776(4) 0.3400(3) 0.68150(13) 0.0508(9) Uani . . 1.000
    H H1A 0.731(5) -0.048(4) 0.5342(18) 0.064(11) Uiso . . 1.000
    H H3A 0.59580 -0.41430 0.49100 0.0310 Uiso calc R 1.000
    H H4A 0.58950 -0.46850 0.60730 0.0330 Uiso calc R 1.000
    H H5A 0.61650 -0.40010 0.73010 0.0370 Uiso calc R 1.000
    H H6A 0.66540 -0.23700 0.80400 0.0380 Uiso calc R 1.000
    H H7A 0.72490 -0.02530 0.76280 0.0390 Uiso calc R 1.000
    H H8A 0.73430 0.02750 0.64540 0.0360 Uiso calc R 1.000
    H H21A 0.632(6) -0.230(4) 0.341(2) 0.040(10) Uiso . . 1.000
    H H1B 0.794(4) 0.096(3) 0.4080(16) 0.046(9) Uiso . . 1.000
    H H3B 0.91170 0.46930 0.44460 0.0350 Uiso calc R 1.000
    H H4B 0.89670 0.52430 0.32840 0.0360 Uiso calc R 1.000
    H H5B 0.86860 0.44910 0.20670 0.0370 Uiso calc R 1.000
    H H6B 0.82830 0.28140 0.13460 0.0370 Uiso calc R 1.000
    H H7B 0.78900 0.06570 0.17910 0.0340 Uiso calc R 1.000
    H H8B 0.79000 0.01860 0.29620 0.0330 Uiso calc R 1.000
    H H3 0.59080 0.22710 0.89220 0.0330 Uiso calc R 1.000
    H H6 -0.02450 0.15690 0.95410 0.0300 Uiso calc R 1.000
    H H11 -0.095(6) 0.330(4) 0.754(2) 0.072(13) Uiso . . 1.000
    H H1W 0.643(6) 0.347(5) 0.693(2) 0.062(16) Uiso . . 1.000
    H H2W 0.800(6) 0.333(4) 0.635(2) 0.059(14) Uiso . . 1.000
_geom_special_details
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Cl4 C4 . . 1.735(3) no
    Cl5 C5 . . 1.732(2) no
    O21A C21A . . 1.259(3) no
    O22A C21A . . 1.238(3) no
    O21A H21A . . 0.90(4) no
    O21B C21B . . 1.239(3) no
    O22B C21B . . 1.235(4) no
    O11 C11 . . 1.318(3) no
    O12 C11 . . 1.202(3) no
    O21 C21 . . 1.297(3) no
    O22 C21 . . 1.220(3) no
    O11 H11 . . 0.85(4) no
    O1W H2W . . 0.92(4) no
    O1W H1W . . 0.98(4) no
    N1A C2A . . 1.331(3) no
    N1A C9A . . 1.381(3) no
    N1A H1A . . 0.96(4) no
    N1B C2B . . 1.334(3) no
    N1B C9B . . 1.375(3) no
    N1B H1B . . 0.99(3) no
    C2A C3A . . 1.398(3) no
    C2A C21A . . 1.517(3) no
    C3A C4A . . 1.373(4) no
    C4A C10A . . 1.407(4) no
    C5A C6A . . 1.355(4) no
    C5A C10A . . 1.420(3) no
    C6A C7A . . 1.401(4) no
    C7A C8A . . 1.376(4) no
    C8A C9A . . 1.405(4) no
    C9A C10A . . 1.416(4) no
    C3A H3A . . 0.9500 no
    C4A H4A . . 0.9500 no
    C5A H5A . . 0.9500 no
    C6A H6A . . 0.9500 no
    C7A H7A . . 0.9500 no
    C8A H8A . . 0.9500 no
    C2B C21B . . 1.534(4) no
    C2B C3B . . 1.393(4) no
    C3B C4B . . 1.364(4) no
    C4B C10B . . 1.413(4) no
    C5B C6B . . 1.354(4) no
    C5B C10B . . 1.415(4) no
    C6B C7B . . 1.418(4) no
    C7B C8B . . 1.364(4) no
    C8B C9B . . 1.397(3) no
    C9B C10B . . 1.420(3) no
    C3B H3B . . 0.9500 no
    C4B H4B . . 0.9500 no
    C5B H5B . . 0.9500 no
    C6B H6B . . 0.9500 no
    C7B H7B . . 0.9500 no
    C8B H8B . . 0.9500 no
    C1 C2 . . 1.398(4) no
    C1 C11 . . 1.496(4) no
    C1 C6 . . 1.399(3) no
    C2 C3 . . 1.384(4) no
    C2 C21 . . 1.507(3) no
    C3 C4 . . 1.390(3) no
    C4 C5 . . 1.374(4) no
    C5 C6 . . 1.381(4) no
    C3 H3 . . 0.9500 no
    C6 H6 . . 0.9500 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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C21A O21A H21A . . . 111(3) no
    C11 O11 H11 . . . 107(3) no
    H1W O1W H2W . . . 112(4) no
    C2A N1A C9A . . . 123.3(2) no
    C9A N1A H1A . . . 113(2) no
    C2A N1A H1A . . . 124(2) no
    C2B N1B C9B . . . 123.3(2) no
    C9B N1B H1B . . . 114.8(18) no
    C2B N1B H1B . . . 121.7(18) no
    N1A C2A C21A . . . 116.71(18) no
    N1A C2A C3A . . . 120.2(2) no
    C3A C2A C21A . . . 123.1(2) no
    C2A C3A C4A . . . 119.1(2) no
    C3A C4A C10A . . . 121.0(3) no
    C6A C5A C10A . . . 120.2(3) no
    C5A C6A C7A . . . 121.0(2) no
    C6A C7A C8A . . . 121.4(3) no
    C7A C8A C9A . . . 117.9(3) no
    N1A C9A C10A . . . 117.9(2) no
    C8A C9A C10A . . . 121.6(2) no
    N1A C9A C8A . . . 120.5(2) no
    C4A C10A C5A . . . 123.6(3) no
    C5A C10A C9A . . . 117.9(2) no
    C4A C10A C9A . . . 118.6(2) no
    O22A C21A C2A . . . 116.8(2) no
    O21A C21A O22A . . . 128.2(2) no
    O21A C21A C2A . . . 114.99(19) no
    C4A C3A H3A . . . 120.00 no
    C2A C3A H3A . . . 121.00 no
    C3A C4A H4A . . . 120.00 no
    C10A C4A H4A . . . 119.00 no
    C10A C5A H5A . . . 120.00 no
    C6A C5A H5A . . . 120.00 no
    C7A C6A H6A . . . 119.00 no
    C5A C6A H6A . . . 120.00 no
    C6A C7A H7A . . . 119.00 no
    C8A C7A H7A . . . 119.00 no
    C9A C8A H8A . . . 121.00 no
    C7A C8A H8A . . . 121.00 no
    N1B C2B C21B . . . 116.4(2) no
    C3B C2B C21B . . . 123.4(2) no
    N1B C2B C3B . . . 120.1(2) no
    C2B C3B C4B . . . 119.6(3) no
    C3B C4B C10B . . . 120.5(3) no
    C6B C5B C10B . . . 120.7(3) no
    C5B C6B C7B . . . 120.4(2) no
    C6B C7B C8B . . . 121.1(2) no
    C7B C8B C9B . . . 118.7(2) no
    N1B C9B C10B . . . 117.7(2) no
    C8B C9B C10B . . . 121.6(2) no
    N1B C9B C8B . . . 120.8(2) no
    C4B C10B C9B . . . 118.7(2) no
    C4B C10B C5B . . . 123.7(2) no
    C5B C10B C9B . . . 117.6(2) no
    O21B C21B C2B . . . 114.3(2) no
    O22B C21B C2B . . . 116.3(2) no
    O21B C21B O22B . . . 129.4(2) no
    C4B C3B H3B . . . 120.00 no
    C2B C3B H3B . . . 120.00 no
    C3B C4B H4B . . . 120.00 no
    C10B C4B H4B . . . 120.00 no
    C10B C5B H5B . . . 120.00 no
    C6B C5B H5B . . . 120.00 no
    C5B C6B H6B . . . 120.00 no
    C7B C6B H6B . . . 120.00 no
    C8B C7B H7B . . . 119.00 no
    C6B C7B H7B . . . 119.00 no
    C9B C8B H8B . . . 121.00 no
    C7B C8B H8B . . . 121.00 no
    C2 C1 C11 . . . 123.2(2) no
    C2 C1 C6 . . . 119.0(2) no
    C6 C1 C11 . . . 117.8(2) no
    C1 C2 C21 . . . 121.8(2) no
    C3 C2 C21 . . . 117.9(2) no
    C1 C2 C3 . . . 120.3(2) no
    C2 C3 C4 . . . 119.8(3) no
    Cl4 C4 C5 . . . 120.98(18) no
    C3 C4 C5 . . . 120.3(2) no
    Cl4 C4 C3 . . . 118.8(2) no
    Cl5 C5 C6 . . . 118.3(2) no
    C4 C5 C6 . . . 120.4(2) no
    Cl5 C5 C4 . . . 121.2(2) no
    C1 C6 C5 . . . 120.2(3) no
    O12 C11 C1 . . . 122.4(2) no
    O11 C11 O12 . . . 125.0(2) no
    O11 C11 C1 . . . 112.6(2) no
    O22 C21 C2 . . . 121.5(2) no
    O21 C21 O22 . . . 124.8(2) no
    O21 C21 C2 . . . 113.66(19) no
    C2 C3 H3 . . . 120.00 no
    C4 C3 H3 . . . 120.00 no
    C1 C6 H6 . . . 120.00 no
    C5 C6 H6 . . . 120.00 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
    C9A N1A C2A C3A . . . . -0.8(4) no
    C9A N1A C2A C21A . . . . 178.0(2) no
    C2A N1A C9A C8A . . . . -178.7(2) no
    C2A N1A C9A C10A . . . . 0.5(3) no
    C2B N1B C9B C8B . . . . 178.3(2) no
    C2B N1B C9B C10B . . . . -2.1(3) no
    C9B N1B C2B C3B . . . . -0.1(4) no
    C9B N1B C2B C21B . . . . 178.3(2) no
    C3A C2A C21A O21A . . . . 1.0(4) no
    N1A C2A C21A O21A . . . . -177.7(2) no
    N1A C2A C21A O22A . . . . 1.6(3) no
    N1A C2A C3A C4A . . . . 0.4(4) no
    C21A C2A C3A C4A . . . . -178.3(2) no
    C3A C2A C21A O22A . . . . -179.7(2) no
    C2A C3A C4A C10A . . . . 0.3(4) no
    C3A C4A C10A C9A . . . . -0.6(4) no
    C3A C4A C10A C5A . . . . 179.6(3) no
    C6A C5A C10A C4A . . . . -179.5(3) no
    C6A C5A C10A C9A . . . . 0.7(4) no
    C10A C5A C6A C7A . . . . -0.3(4) no
    C5A C6A C7A C8A . . . . 0.1(5) no
    C6A C7A C8A C9A . . . . -0.2(4) no
    C7A C8A C9A N1A . . . . 179.7(2) no
    C7A C8A C9A C10A . . . . 0.6(4) no
    N1A C9A C10A C5A . . . . -179.9(2) no
    C8A C9A C10A C4A . . . . 179.4(2) no
    C8A C9A C10A C5A . . . . -0.8(4) no
    N1A C9A C10A C4A . . . . 0.2(3) no
    N1B C2B C3B C4B . . . . 3.0(4) no
    C21B C2B C3B C4B . . . . -175.3(3) no
    N1B C2B C21B O21B . . . . 173.8(2) no
    N1B C2B C21B O22B . . . . -7.5(4) no
    C3B C2B C21B O21B . . . . -7.9(4) no
    C3B C2B C21B O22B . . . . 170.9(3) no
    C2B C3B C4B C10B . . . . -3.5(4) no
    C3B C4B C10B C5B . . . . -178.5(3) no
    C3B C4B C10B C9B . . . . 1.3(4) no
    C10B C5B C6B C7B . . . . 0.2(4) no
    C6B C5B C10B C4B . . . . 179.2(3) no
    C6B C5B C10B C9B . . . . -0.7(4) no
    C5B C6B C7B C8B . . . . 0.1(4) no
    C6B C7B C8B C9B . . . . 0.1(4) no
    C7B C8B C9B N1B . . . . 179.0(2) no
    C7B C8B C9B C10B . . . . -0.6(4) no
    N1B C9B C10B C4B . . . . 1.5(3) no
    N1B C9B C10B C5B . . . . -178.7(2) no
    C8B C9B C10B C4B . . . . -178.9(2) no
    C8B C9B C10B C5B . . . . 0.9(3) no
    C6 C1 C2 C3 . . . . 0.2(3) no
    C6 C1 C2 C21 . . . . 178.17(19) no
    C11 C1 C2 C3 . . . . 179.12(19) no
    C11 C1 C2 C21 . . . . -2.9(3) no
    C2 C1 C6 C5 . . . . 0.1(3) no
    C11 C1 C6 C5 . . . . -178.89(19) no
    C2 C1 C11 O11 . . . . -38.2(3) no
    C2 C1 C11 O12 . . . . 143.8(2) no
    C6 C1 C11 O11 . . . . 140.8(2) no
    C6 C1 C11 O12 . . . . -37.2(3) no
    C1 C2 C3 C4 . . . . -0.7(3) no
    C21 C2 C3 C4 . . . . -178.72(18) no
    C1 C2 C21 O21 . . . . -55.7(3) no
    C1 C2 C21 O22 . . . . 125.4(2) no
    C3 C2 C21 O21 . . . . 122.4(2) no
    C3 C2 C21 O22 . . . . -56.5(3) no
    C2 C3 C4 Cl4 . . . . -179.22(16) no
    C2 C3 C4 C5 . . . . 0.8(3) no
    Cl4 C4 C5 Cl5 . . . . -1.9(3) no
    Cl4 C4 C5 C6 . . . . 179.50(16) no
    C3 C4 C5 Cl5 . . . . 178.05(16) no
    C3 C4 C5 C6 . . . . -0.6(3) no
    Cl5 C5 C6 C1 . . . . -178.56(16) no
    C4 C5 C6 C1 . . . . 0.1(3) 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
    O11 H11 O1W 1_455 0.85(4) 1.70(4) 2.510(3) 159(4) yes
    O21A H21A O21 2_656 0.90(4) 1.64(4) 2.531(2) 179(5) yes
    N1A H1A O22B . 0.96(4) 1.84(4) 2.788(3) 168(3) yes
    N1B H1B O22A . 0.99(3) 1.80(3) 2.756(3) 163(3) yes
    O1W H1W O22 . 0.98(4) 1.92(4) 2.771(3) 143(4) yes
    O1W H2W O21B . 0.92(4) 1.71(4) 2.625(3) 169(4) yes
    C3 H3 O12 1_655 0.95 2.41 3.239(3) 146 no
    C5B H5B O11 2_666 0.95 2.60 3.441(4) 148 no
    C7A H7A O12 1_655 0.95 2.51 3.435(3) 163 no
    C8A H8A O22B . 0.95 2.51 3.234(3) 133 no
    C8B H8B O22A . 0.95 2.50 3.190(3) 130 no
    C8B H8B O21 2_656 0.95 2.43 3.204(3) 138 no
