##############################################################################
###                                                                        ###
###           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 2.4.    #
#                                                                            #
# 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                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
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data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2009-10-11
_journal_date_accepted     2009-11-10
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2009
_journal_volume     65
_journal_issue     12
_journal_page_first     o639
_journal_page_last     o644
_journal_paper_category     FO
_journal_coeditor_code     GD3317
_publ_contact_author_name     'Professor Israel Goldberg'
_publ_contact_author_address
;
School of Chemistry
Tel-Aviv University
Ramat-Aviv
69978 Tel-Aviv
Israel
;
_publ_contact_author_email     goldberg@post.tau.ac.il
_publ_contact_author_fax     '972 3 6409293'
_publ_contact_author_phone     '972 3 6409965'
_publ_section_title
;
Hydrogen bonding and π--π interactions in 1-benzofuran-2,3-dicarboxylic acid
and its 1:1 cocrystals with pyridine, phenazine and 1,4-phenylenediamine
;
loop_
    _publ_author_name
    _publ_author_address
    'Hatem M. Titi'
;
School of Chemistry
Sackler Faculty of Exact Sciences
Tel-Aviv University
Ramat-Aviv
69978 Tel-Aviv
Israel
;
    'Israel Goldberg'
;
School of Chemistry
Sackler Faculty of Exact Sciences
Tel-Aviv University
Ramat-Aviv
69978 Tel-Aviv
Israel
;
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
1-Benzofuran-2,3-dicarboxylic acid
;
_chemical_name_common     ?
_chemical_formula_moiety     'C10 H6 O5'
_chemical_formula_sum     'C10 H6 O5'
_chemical_formula_iupac     'C10 H6 O5'
_chemical_formula_weight     206.15
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     6.9614(3)
_cell_length_b     18.2529(7)
_cell_length_c     7.4731(3)
_cell_angle_alpha     90.00
_cell_angle_beta     116.840(2)
_cell_angle_gamma     90.00
_cell_volume     847.28(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1888
_cell_measurement_theta_min     3.25
_cell_measurement_theta_max     27.87
_cell_measurement_temperature     110(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.45
_exptl_crystal_size_mid     0.35
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.616
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     424
_exptl_absorpt_coefficient_mu     0.133
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
;
_diffrn_ambient_temperature     110(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     'Nonius KappaCCD area-detector'
_diffrn_measurement_method     '1 deg. φ and ω scans'
_diffrn_detector_area_resol_mean     12.8
_diffrn_reflns_number     7021
_diffrn_reflns_av_R_equivalents     0.0350
_diffrn_reflns_av_sigmaI/netI     0.0359
_diffrn_reflns_theta_min     3.25
_diffrn_reflns_theta_max     27.87
_diffrn_reflns_theta_full     27.87
_diffrn_measured_fraction_theta_max     0.986
_diffrn_measured_fraction_theta_full     0.986
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     23
_diffrn_reflns_limit_l_min     -9
_diffrn_reflns_limit_l_max     8
_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 >
σ(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     1982
_reflns_number_gt     1517
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0659
_refine_ls_R_factor_gt     0.0488
_refine_ls_wR_factor_gt     0.1301
_refine_ls_wR_factor_ref     0.1407
_refine_ls_goodness_of_fit_ref     1.065
_refine_ls_restrained_S_all     1.065
_refine_ls_number_reflns     1982
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0934P)²+0.0306P] 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     0.312
_refine_diff_density_min     -0.305
_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'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'COLLECT (Nonius, 1999)'
_computing_cell_refinement     'DENZO (Otwinowski & Minor, 1997)'
_computing_data_reduction     'DENZO (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SIR97 (Altomare et al.,  1994)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae et al.,
2006)
;
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
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 0.24362(17) 0.34674(6) 0.67414(16) 0.0258(3) Uani d . 1 . .
    C C2 0.2572(2) 0.40425(9) 0.5639(2) 0.0236(4) Uani d . 1 . .
    C C3 0.2783(2) 0.38137(9) 0.3988(2) 0.0236(4) Uani d . 1 . .
    C C4 0.2819(2) 0.30208(9) 0.4067(2) 0.0233(4) Uani d . 1 . .
    C C5 0.3014(3) 0.24582(9) 0.2891(3) 0.0283(4) Uani d . 1 . .
    H H5 0.3187 0.2561 0.1726 0.034 Uiso calc R 1 . .
    C C6 0.2944(3) 0.17430(10) 0.3489(3) 0.0325(4) Uani d . 1 . .
    H H6 0.3105 0.1351 0.2731 0.039 Uiso calc R 1 . .
    C C7 0.2642(2) 0.15829(9) 0.5178(3) 0.0322(4) Uani d . 1 . .
    H H7 0.2567 0.1086 0.5516 0.039 Uiso calc R 1 . .
    C C8 0.2452(2) 0.21307(10) 0.6364(3) 0.0308(4) Uani d . 1 . .
    H H8 0.2251 0.2026 0.7514 0.037 Uiso calc R 1 . .
    C C9 0.2573(2) 0.28443(9) 0.5771(2) 0.0249(4) Uani d . 1 . .
    C C10 0.2505(2) 0.47676(9) 0.6501(2) 0.0254(4) Uani d . 1 . .
    O O11 0.23612(18) 0.53520(6) 0.54161(17) 0.0293(3) Uani d . 1 . .
    H H11 0.252(3) 0.5254(11) 0.419(3) 0.035 Uiso d . 1 . .
    O O12 0.25603(19) 0.48259(7) 0.81497(18) 0.0327(3) Uani d . 1 . .
    C C13 0.2827(2) 0.42772(9) 0.2395(2) 0.0250(4) Uani d . 1 . .
    O O14 0.30575(19) 0.39071(7) 0.10104(18) 0.0308(3) Uani d . 1 . .
    H H14 0.290(3) 0.4214(12) -0.010(3) 0.037 Uiso d . 1 . .
    O O15 0.26407(18) 0.49490(7) 0.23463(17) 0.0298(3) Uani d . 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 C2 . 1.3640(19) ?
    O1 C9 . 1.3750(19) ?
    C2 C3 . 1.372(2) ?
    C2 C10 . 1.482(2) ?
    C3 C4 . 1.448(2) ?
    C3 C13 . 1.472(2) ?
    C4 C9 . 1.397(2) ?
    C4 C5 . 1.397(2) ?
    C5 C6 . 1.388(2) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.401(3) ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.382(3) ?
    C7 H7 . 0.9500 ?
    C8 C9 . 1.391(2) ?
    C8 H8 . 0.9500 ?
    C10 O12 . 1.220(2) ?
    C10 O11 . 1.316(2) ?
    O11 H11 . 0.99(2) ?
    C13 O15 . 1.232(2) ?
    C13 O14 . 1.305(2) ?
    O14 H14 . 0.96(2) ?
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 O1 C9 . . 106.13(12) ?
    O1 C2 C3 . . 111.95(13) ?
    O1 C2 C10 . . 113.61(13) ?
    C3 C2 C10 . . 134.42(15) ?
    C2 C3 C4 . . 105.92(13) ?
    C2 C3 C13 . . 127.03(15) ?
    C4 C3 C13 . . 126.94(14) ?
    C9 C4 C5 . . 119.36(15) ?
    C9 C4 C3 . . 105.12(13) ?
    C5 C4 C3 . . 135.53(15) ?
    C6 C5 C4 . . 117.49(16) ?
    C6 C5 H5 . . 121.3 ?
    C4 C5 H5 . . 121.3 ?
    C5 C6 C7 . . 121.84(16) ?
    C5 C6 H6 . . 119.1 ?
    C7 C6 H6 . . 119.1 ?
    C8 C7 C6 . . 121.60(16) ?
    C8 C7 H7 . . 119.2 ?
    C6 C7 H7 . . 119.2 ?
    C7 C8 C9 . . 115.87(16) ?
    C7 C8 H8 . . 122.1 ?
    C9 C8 H8 . . 122.1 ?
    O1 C9 C8 . . 125.32(15) ?
    O1 C9 C4 . . 110.86(13) ?
    C8 C9 C4 . . 123.81(15) ?
    O12 C10 O11 . . 120.69(15) ?
    O12 C10 C2 . . 121.61(15) ?
    O11 C10 C2 . . 117.70(15) ?
    C10 O11 H11 . . 114.5(12) ?
    O15 C13 O14 . . 122.77(15) ?
    O15 C13 C3 . . 123.73(15) ?
    O14 C13 C3 . . 113.50(15) ?
    C13 O14 H14 . . 111.9(13) ?
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
    O11 H11 O15 . 0.99(2) 1.52(2) 2.4990(16) 168.6(19)
    O14 H14 O12 1_554 0.96(2) 1.66(2) 2.6143(17) 172.7(19)
    C7 H7 O12 2_546 0.95 2.52 3.468(2) 173
data_II
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
Pyridinium 2-carboxylato-1-benzofuran-3-carboxylic acid
;
_chemical_name_common     ?
_chemical_formula_moiety     'C5 H6 N + , C10 H5 O5 -'
_chemical_formula_sum     'C15 H11 N O5'
_chemical_formula_iupac     'C5 H6 N + , C10 H5 O5 -'
_chemical_formula_weight     285.25
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     3.75760(10)
_cell_length_b     18.3933(6)
_cell_length_c     17.9788(7)
_cell_angle_alpha     90.00
_cell_angle_beta     93.5522(11)
_cell_angle_gamma     90.00
_cell_volume     1240.21(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2696
_cell_measurement_theta_min     2.49
_cell_measurement_theta_max     27.88
_cell_measurement_temperature     110(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.50
_exptl_crystal_size_mid     0.10
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.528
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     592
_exptl_absorpt_coefficient_mu     0.117
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
;
_diffrn_ambient_temperature     110(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     'Nonius KappaCCD area-detector'
_diffrn_measurement_method     '1 deg. φ and ω scans'
_diffrn_detector_area_resol_mean     12.8
_diffrn_reflns_number     10181
_diffrn_reflns_av_R_equivalents     0.0670
_diffrn_reflns_av_sigmaI/netI     0.0788
_diffrn_reflns_theta_min     2.49
_diffrn_reflns_theta_max     27.88
_diffrn_reflns_theta_full     27.88
_diffrn_measured_fraction_theta_max     0.986
_diffrn_measured_fraction_theta_full     0.986
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     4
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     24
_diffrn_reflns_limit_l_min     -23
_diffrn_reflns_limit_l_max     23
_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 >
σ(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     2897
_reflns_number_gt     1675
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1111
_refine_ls_R_factor_gt     0.0516
_refine_ls_wR_factor_gt     0.1118
_refine_ls_wR_factor_ref     0.1387
_refine_ls_goodness_of_fit_ref     0.974
_refine_ls_restrained_S_all     0.974
_refine_ls_number_reflns     2897
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
               'calc w = 1/[σ²(Fo²)+(0.0730P)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     0.347
_refine_diff_density_min     -0.330
_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'
_computing_data_collection     'COLLECT (Nonius, 1999)'
_computing_cell_refinement     'DENZO (Otwinowski & Minor, 1997)'
_computing_data_reduction     'DENZO (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SIR97 (Altomare et al.,  1994)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae et al.,
2006)
;
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
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 0.3813(3) -0.03491(8) 0.71947(8) 0.0210(4) Uani d . 1 . .
    C C2 0.3553(5) 0.03917(11) 0.72630(11) 0.0189(5) Uani d . 1 . .
    C C3 0.2207(5) 0.05777(11) 0.79301(11) 0.0197(5) Uani d . 1 . .
    C C4 0.1552(5) -0.00923(12) 0.83098(11) 0.0200(5) Uani d . 1 . .
    C C5 0.0238(5) -0.02886(13) 0.89954(12) 0.0240(5) Uani d . 1 . .
    H H5 -0.0491 0.0070 0.9334 0.029 Uiso calc R 1 . .
    C C6 0.0036(5) -0.10205(12) 0.91624(12) 0.0257(5) Uani d . 1 . .
    H H6 -0.0819 -0.1164 0.9627 0.031 Uiso calc R 1 . .
    C C7 0.1060(5) -0.15561(13) 0.86651(12) 0.0254(5) Uani d . 1 . .
    H H7 0.0853 -0.2054 0.8796 0.030 Uiso calc R 1 . .
    C C8 0.2367(5) -0.13754(12) 0.79863(12) 0.0231(5) Uani d . 1 . .
    H H8 0.3071 -0.1734 0.7645 0.028 Uiso calc R 1 . .
    C C9 0.2583(5) -0.06430(11) 0.78375(11) 0.0199(5) Uani d . 1 . .
    C C10 0.4765(5) 0.08092(12) 0.66180(12) 0.0217(5) Uani d . 1 . .
    O O11 0.5909(4) 0.04490(8) 0.60852(8) 0.0270(4) Uani d . 1 . .
    O O12 0.4586(4) 0.14932(8) 0.66389(8) 0.0275(4) Uani d . 1 . .
    C C13 0.1479(5) 0.13089(13) 0.82411(12) 0.0240(5) Uani d . 1 . .
    O O14 0.2145(4) 0.18934(8) 0.78447(9) 0.0281(4) Uani d . 1 . .
    H H14 0.306(6) 0.1739(13) 0.7370(14) 0.034 Uiso d . 1 . .
    O O15 0.0275(4) 0.13638(9) 0.88545(9) 0.0312(4) Uani d . 1 . .
    N N16 0.8733(4) 0.12783(10) 0.50874(10) 0.0212(4) Uani d . 1 . .
    H H16 0.759(5) 0.0932(12) 0.5495(12) 0.025 Uiso d . 1 . .
    C C17 0.9583(5) 0.09473(12) 0.44592(12) 0.0225(5) Uani d . 1 . .
    H H17 0.9110 0.0444 0.4390 0.027 Uiso calc R 1 . .
    C C18 1.1151(5) 0.13408(12) 0.39114(12) 0.0236(5) Uani d . 1 . .
    H H18 1.1818 0.1109 0.3469 0.028 Uiso calc R 1 . .
    C C19 1.1735(5) 0.20767(12) 0.40165(12) 0.0247(5) Uani d . 1 . .
    H H19 1.2777 0.2356 0.3642 0.030 Uiso calc R 1 . .
    C C20 1.0797(5) 0.24058(12) 0.46692(12) 0.0240(5) Uani d . 1 . .
    H H20 1.1166 0.2912 0.4745 0.029 Uiso calc R 1 . .
    C C21 0.9324(5) 0.19892(12) 0.52042(12) 0.0240(5) Uani d . 1 . .
    H H21 0.8722 0.2206 0.5659 0.029 Uiso calc R 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 C2 . 1.372(2) ?
    O1 C9 . 1.381(2) ?
    C2 C3 . 1.373(3) ?
    C2 C10 . 1.486(3) ?
    C3 C4 . 1.437(3) ?
    C3 C13 . 1.488(3) ?
    C4 C9 . 1.392(3) ?
    C4 C5 . 1.403(3) ?
    C5 C6 . 1.382(3) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.400(3) ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.384(3) ?
    C7 H7 . 0.9500 ?
    C8 C9 . 1.377(3) ?
    C8 H8 . 0.9500 ?
    C10 O12 . 1.260(3) ?
    C10 O11 . 1.262(3) ?
    C13 O15 . 1.222(3) ?
    C13 O14 . 1.322(3) ?
    O14 H14 . 0.98(2) ?
    N16 C17 . 1.339(3) ?
    N16 C21 . 1.341(3) ?
    N16 H16 . 1.08(2) ?
    C17 C18 . 1.383(3) ?
    C17 H17 . 0.9500 ?
    C18 C19 . 1.382(3) ?
    C18 H18 . 0.9500 ?
    C19 C20 . 1.385(3) ?
    C19 H19 . 0.9500 ?
    C20 C21 . 1.373(3) ?
    C20 H20 . 0.9500 ?
    C21 H21 . 0.9500 ?
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 O1 C9 . . 106.52(15) ?
    O1 C2 C3 . . 110.95(17) ?
    O1 C2 C10 . . 114.61(17) ?
    C3 C2 C10 . . 134.4(2) ?
    C2 C3 C4 . . 106.52(18) ?
    C2 C3 C13 . . 129.7(2) ?
    C4 C3 C13 . . 123.74(19) ?
    C9 C4 C5 . . 118.4(2) ?
    C9 C4 C3 . . 105.78(18) ?
    C5 C4 C3 . . 135.9(2) ?
    C6 C5 C4 . . 117.9(2) ?
    C6 C5 H5 . . 121.0 ?
    C4 C5 H5 . . 121.0 ?
    C5 C6 C7 . . 121.7(2) ?
    C5 C6 H6 . . 119.1 ?
    C7 C6 H6 . . 119.1 ?
    C8 C7 C6 . . 121.4(2) ?
    C8 C7 H7 . . 119.3 ?
    C6 C7 H7 . . 119.3 ?
    C9 C8 C7 . . 115.8(2) ?
    C9 C8 H8 . . 122.1 ?
    C7 C8 H8 . . 122.1 ?
    C8 C9 O1 . . 124.91(19) ?
    C8 C9 C4 . . 124.9(2) ?
    O1 C9 C4 . . 110.22(18) ?
    O12 C10 O11 . . 124.60(19) ?
    O12 C10 C2 . . 118.25(18) ?
    O11 C10 C2 . . 117.2(2) ?
    O15 C13 O14 . . 120.8(2) ?
    O15 C13 C3 . . 120.0(2) ?
    O14 C13 C3 . . 119.14(19) ?
    C13 O14 H14 . . 108.8(14) ?
    C17 N16 C21 . . 121.98(19) ?
    C17 N16 H16 . . 115.4(12) ?
    C21 N16 H16 . . 122.6(12) ?
    N16 C17 C18 . . 119.8(2) ?
    N16 C17 H17 . . 120.1 ?
    C18 C17 H17 . . 120.1 ?
    C17 C18 C19 . . 119.1(2) ?
    C17 C18 H18 . . 120.5 ?
    C19 C18 H18 . . 120.5 ?
    C18 C19 C20 . . 119.8(2) ?
    C18 C19 H19 . . 120.1 ?
    C20 C19 H19 . . 120.1 ?
    C21 C20 C19 . . 119.0(2) ?
    C21 C20 H20 . . 120.5 ?
    C19 C20 H20 . . 120.5 ?
    N16 C21 C20 . . 120.3(2) ?
    N16 C21 H21 . . 119.8 ?
    C20 C21 H21 . . 119.8 ?
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
    O14 H14 O12 . 0.98(2) 1.53(3) 2.516(2) 178(2)
    N16 H16 O11 . 1.08(2) 1.55(2) 2.628(2) 179(2)
    C17 H17 O11 3_656 0.95 2.60 3.400(3) 142
    C18 H18 O1 3_756 0.95 2.51 3.366(3) 150
    C19 H19 O14 4_765 0.95 2.64 3.562(3) 165
data_III
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
Phenazinium 3-carboxylato-1-benzofuran-2-carboxylic acid
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H9 N2 + , C10 H5 O5 -'
_chemical_formula_sum     'C22 H14 N2 O5'
_chemical_formula_iupac     'C12 H9 N2 + , C10 H5 O5 -'
_chemical_formula_weight     386.35
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P n'
_symmetry_space_group_name_Hall     'P -2yac'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    'x+1/2, -y, z+1/2'
_cell_length_a     5.3881(2)
_cell_length_b     8.3227(4)
_cell_length_c     18.6514(11)
_cell_angle_alpha     90.00
_cell_angle_beta     90.3794(18)
_cell_angle_gamma     90.00
_cell_volume     836.38(7)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2631
_cell_measurement_theta_min     2.32
_cell_measurement_theta_max     27.83
_cell_measurement_temperature     110(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.50
_exptl_crystal_size_mid     0.40
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.534
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     400
_exptl_absorpt_coefficient_mu     0.111
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
;
_diffrn_ambient_temperature     110(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     'Nonius KappaCCD area-detector'
_diffrn_measurement_method     '1 deg. φ and ω scans'
_diffrn_detector_area_resol_mean     12.8
_diffrn_reflns_number     7323
_diffrn_reflns_av_R_equivalents     0.0443
_diffrn_reflns_av_sigmaI/netI     0.0758
_diffrn_reflns_theta_min     3.28
_diffrn_reflns_theta_max     27.83
_diffrn_reflns_theta_full     27.83
_diffrn_measured_fraction_theta_max     0.992
_diffrn_measured_fraction_theta_full     0.992
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     24
_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 >
σ(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.
The Friedel pairs were merged as suggested by Checkcif. As a result, the
data-to-parameters ratio is somewhat low.
;
_reflns_number_total     1970
_reflns_number_gt     1352
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0810
_refine_ls_R_factor_gt     0.0448
_refine_ls_wR_factor_gt     0.0918
_refine_ls_wR_factor_ref     0.1051
_refine_ls_goodness_of_fit_ref     1.024
_refine_ls_restrained_S_all     1.023
_refine_ls_number_reflns     1970
_refine_ls_number_parameters     269
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
               'calc w = 1/[σ²(Fo²)+(0.0543P)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     0.000
_refine_diff_density_max     0.284
_refine_diff_density_min     -0.214
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.014(4)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details     ?
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     'COLLECT (Nonius, 1999)'
_computing_cell_refinement     'DENZO (Otwinowski & Minor, 1997)'
_computing_data_reduction     'DENZO (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SIR97 (Altomare et al.,  1994)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae et al.,
2006)
;
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
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 -0.0823(4) 0.0534(3) 0.33621(13) 0.0288(6) Uani d . 1 . .
    C C2 0.0873(6) 0.1450(4) 0.37378(18) 0.0267(8) Uani d . 1 . .
    C C3 0.2624(6) 0.2099(4) 0.32969(19) 0.0255(8) Uani d . 1 . .
    C C4 0.2029(6) 0.1535(4) 0.25793(18) 0.0244(8) Uani d . 1 . .
    C C5 0.3084(6) 0.1660(4) 0.18949(18) 0.0272(8) Uani d . 1 . .
    H H5 0.4541 0.2280 0.1821 0.033 Uiso calc R 1 . .
    C C6 0.1955(6) 0.0862(4) 0.13342(19) 0.0291(8) Uani d . 1 . .
    H H6 0.2662 0.0924 0.0870 0.035 Uiso calc R 1 . .
    C C7 -0.0216(6) -0.0040(5) 0.14333(18) 0.0323(9) Uani d . 1 . .
    H H7 -0.0965 -0.0555 0.1032 0.039 Uiso calc R 1 . .
    C C8 -0.1290(6) -0.0196(5) 0.21002(18) 0.0287(8) Uani d . 1 . .
    H H8 -0.2757 -0.0805 0.2174 0.034 Uiso calc R 1 . .
    C C9 -0.0080(6) 0.0599(4) 0.26538(18) 0.0258(8) Uani d . 1 . .
    C C10 0.0409(7) 0.1437(5) 0.45215(19) 0.0306(9) Uani d . 1 . .
    O O11 0.1996(5) 0.2263(3) 0.49206(14) 0.0373(7) Uani d . 1 . .
    H H11 0.312(8) 0.288(6) 0.461(2) 0.045 Uiso d . 1 . .
    O O12 -0.1297(4) 0.0690(3) 0.47726(13) 0.0383(7) Uani d . 1 . .
    C C13 0.4685(6) 0.3198(4) 0.3483(2) 0.0290(8) Uani d . 1 . .
    O O14 0.5928(4) 0.3723(3) 0.29539(13) 0.0324(6) Uani d . 1 . .
    O O15 0.5115(4) 0.3595(3) 0.41287(13) 0.0351(7) Uani d . 1 . .
    C C16 0.9288(6) 0.4975(5) 0.16645(19) 0.0309(9) Uani d . 1 . .
    H H16 0.7843 0.4349 0.1746 0.037 Uiso calc R 1 . .
    C C17 1.0186(7) 0.5167(5) 0.09880(19) 0.0330(9) Uani d . 1 . .
    H H17 0.9324 0.4690 0.0596 0.040 Uiso calc R 1 . .
    C C18 1.2367(7) 0.6057(5) 0.0857(2) 0.0336(9) Uani d . 1 . .
    H H18 1.2961 0.6159 0.0380 0.040 Uiso calc R 1 . .
    C C19 1.3626(6) 0.6769(4) 0.14050(19) 0.0301(8) Uani d . 1 . .
    H H19 1.5097 0.7360 0.1310 0.036 Uiso calc R 1 . .
    C C20 1.2749(6) 0.6632(4) 0.21200(19) 0.0259(8) Uani d . 1 . .
    N N21 1.3953(5) 0.7381(4) 0.26556(16) 0.0277(7) Uani d . 1 . .
    C C22 1.3032(6) 0.7270(4) 0.3321(2) 0.0274(8) Uani d . 1 . .
    C C23 1.4220(6) 0.8082(5) 0.38998(19) 0.0290(8) Uani d . 1 . .
    H H23 1.5665 0.8707 0.3818 0.035 Uiso calc R 1 . .
    C C24 1.3275(6) 0.7959(5) 0.4571(2) 0.0325(9) Uani d . 1 . .
    H H24 1.4084 0.8494 0.4957 0.039 Uiso calc R 1 . .
    C C25 1.1094(7) 0.7041(5) 0.4708(2) 0.0329(9) Uani d . 1 . .
    H H25 1.0456 0.6993 0.5181 0.039 Uiso calc R 1 . .
    C C26 0.9915(6) 0.6236(5) 0.41720(19) 0.0295(8) Uani d . 1 . .
    H H26 0.8491 0.5604 0.4271 0.035 Uiso calc R 1 . .
    C C27 1.0827(6) 0.6349(4) 0.34679(19) 0.0260(8) Uani d . 1 . .
    N N28 0.9682(5) 0.5593(4) 0.29184(15) 0.0266(7) Uani d . 1 . .
    H H28 0.815(7) 0.492(5) 0.3054(19) 0.032 Uiso d . 1 . .
    C C29 1.0546(6) 0.5726(4) 0.22423(19) 0.0255(8) Uani d . 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 C2 . 1.378(4) ?
    O1 C9 . 1.384(4) ?
    C2 C3 . 1.367(5) ?
    C2 C10 . 1.484(5) ?
    C3 C4 . 1.452(5) ?
    C3 C13 . 1.478(5) ?
    C4 C9 . 1.385(5) ?
    C4 C5 . 1.405(5) ?
    C5 C6 . 1.377(5) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.403(5) ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.381(5) ?
    C7 H7 . 0.9500 ?
    C8 C9 . 1.385(5) ?
    C8 H8 . 0.9500 ?
    C10 O12 . 1.207(4) ?
    C10 O11 . 1.323(4) ?
    O11 H11 . 0.99(5) ?
    C13 O15 . 1.269(4) ?
    C13 O14 . 1.273(4) ?
    C16 C17 . 1.364(5) ?
    C16 C29 . 1.415(5) ?
    C16 H16 . 0.9500 ?
    C17 C18 . 1.412(5) ?
    C17 H17 . 0.9500 ?
    C18 C19 . 1.359(5) ?
    C18 H18 . 0.9500 ?
    C19 C20 . 1.422(5) ?
    C19 H19 . 0.9500 ?
    C20 N21 . 1.341(4) ?
    C20 C29 . 1.426(5) ?
    N21 C22 . 1.343(4) ?
    C22 C23 . 1.422(5) ?
    C22 C27 . 1.442(5) ?
    C23 C24 . 1.359(5) ?
    C23 H23 . 0.9500 ?
    C24 C25 . 1.426(6) ?
    C24 H24 . 0.9500 ?
    C25 C26 . 1.357(5) ?
    C25 H25 . 0.9500 ?
    C26 C27 . 1.408(5) ?
    C26 H26 . 0.9500 ?
    C27 N28 . 1.349(4) ?
    N28 C29 . 1.351(4) ?
    N28 H28 . 1.03(4) ?
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 O1 C9 . . 105.6(3) ?
    C3 C2 O1 . . 111.8(3) ?
    C3 C2 C10 . . 135.8(3) ?
    O1 C2 C10 . . 112.4(3) ?
    C2 C3 C4 . . 106.1(3) ?
    C2 C3 C13 . . 128.6(3) ?
    C4 C3 C13 . . 125.2(3) ?
    C9 C4 C5 . . 118.0(3) ?
    C9 C4 C3 . . 105.4(3) ?
    C5 C4 C3 . . 136.5(3) ?
    C6 C5 C4 . . 118.3(3) ?
    C6 C5 H5 . . 120.8 ?
    C4 C5 H5 . . 120.8 ?
    C5 C6 C7 . . 121.5(3) ?
    C5 C6 H6 . . 119.2 ?
    C7 C6 H6 . . 119.2 ?
    C8 C7 C6 . . 121.6(3) ?
    C8 C7 H7 . . 119.2 ?
    C6 C7 H7 . . 119.2 ?
    C7 C8 C9 . . 115.4(3) ?
    C7 C8 H8 . . 122.3 ?
    C9 C8 H8 . . 122.3 ?
    O1 C9 C8 . . 123.7(3) ?
    O1 C9 C4 . . 111.1(3) ?
    C8 C9 C4 . . 125.2(3) ?
    O12 C10 O11 . . 122.7(3) ?
    O12 C10 C2 . . 121.3(3) ?
    O11 C10 C2 . . 116.0(3) ?
    C10 O11 H11 . . 110(2) ?
    O15 C13 O14 . . 123.6(3) ?
    O15 C13 C3 . . 121.0(3) ?
    O14 C13 C3 . . 115.4(3) ?
    C17 C16 C29 . . 118.8(3) ?
    C17 C16 H16 . . 120.6 ?
    C29 C16 H16 . . 120.6 ?
    C16 C17 C18 . . 121.5(3) ?
    C16 C17 H17 . . 119.2 ?
    C18 C17 H17 . . 119.2 ?
    C19 C18 C17 . . 120.7(3) ?
    C19 C18 H18 . . 119.7 ?
    C17 C18 H18 . . 119.7 ?
    C18 C19 C20 . . 120.2(3) ?
    C18 C19 H19 . . 119.9 ?
    C20 C19 H19 . . 119.9 ?
    N21 C20 C19 . . 119.9(3) ?
    N21 C20 C29 . . 121.7(3) ?
    C19 C20 C29 . . 118.3(3) ?
    C22 N21 C20 . . 118.5(3) ?
    N21 C22 C23 . . 120.1(3) ?
    N21 C22 C27 . . 121.5(3) ?
    C23 C22 C27 . . 118.4(3) ?
    C24 C23 C22 . . 119.6(3) ?
    C24 C23 H23 . . 120.2 ?
    C22 C23 H23 . . 120.2 ?
    C23 C24 C25 . . 121.3(4) ?
    C23 C24 H24 . . 119.4 ?
    C25 C24 H24 . . 119.4 ?
    C26 C25 C24 . . 121.0(4) ?
    C26 C25 H25 . . 119.5 ?
    C24 C25 H25 . . 119.5 ?
    C25 C26 C27 . . 119.3(3) ?
    C25 C26 H26 . . 120.3 ?
    C27 C26 H26 . . 120.3 ?
    N28 C27 C26 . . 121.1(3) ?
    N28 C27 C22 . . 118.5(3) ?
    C26 C27 C22 . . 120.4(3) ?
    C27 N28 C29 . . 120.8(3) ?
    C27 N28 H28 . . 115(2) ?
    C29 N28 H28 . . 124(2) ?
    N28 C29 C16 . . 120.5(3) ?
    N28 C29 C20 . . 119.0(3) ?
    C16 C29 C20 . . 120.5(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
    O11 H11 O15 . 0.99(5) 1.52(5) 2.503(3) 171(4)
    N28 H28 O14 . 1.03(4) 1.57(4) 2.553(4) 158(3)
    C6 H6 O12 2_554 0.95 2.51 3.328(4) 143.7
    C8 H8 N21 1_345 0.95 2.50 3.427(4) 165.3
    C26 H26 O15 . 0.95 2.48 3.395(4) 160.8
data_IV
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
4-Aminoanilinium 2-carboxylato-1-benzofuran-3-carboxylic acid
;
_chemical_name_common     ?
_chemical_formula_moiety     'C6 H9 N2 + , C10 H5 O5 -'
_chemical_formula_sum     'C16 H14 N2 O5'
_chemical_formula_iupac     'C6 H9 N2 + , C10 H5 O5 -'
_chemical_formula_weight     314.29
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21'
_symmetry_space_group_name_Hall     'P 2yb'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     5.8427(2)
_cell_length_b     17.5893(7)
_cell_length_c     7.1302(3)
_cell_angle_alpha     90.00
_cell_angle_beta     104.6337(16)
_cell_angle_gamma     90.00
_cell_volume     708.99(5)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1601
_cell_measurement_theta_min     2.32
_cell_measurement_theta_max     27.83
_cell_measurement_temperature     110(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.50
_exptl_crystal_size_mid     0.50
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.472
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     328
_exptl_absorpt_coefficient_mu     0.111
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
;
_diffrn_ambient_temperature     110(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     'Nonius KappaCCD area-detector'
_diffrn_measurement_method     '1 deg. φ and ω scans'
_diffrn_detector_area_resol_mean     12.8
_diffrn_reflns_number     5908
_diffrn_reflns_av_R_equivalents     0.0360
_diffrn_reflns_av_sigmaI/netI     0.0492
_diffrn_reflns_theta_min     2.32
_diffrn_reflns_theta_max     27.83
_diffrn_reflns_theta_full     27.83
_diffrn_measured_fraction_theta_max     0.991
_diffrn_measured_fraction_theta_full     0.991
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -20
_diffrn_reflns_limit_k_max     22
_diffrn_reflns_limit_l_min     -9
_diffrn_reflns_limit_l_max     9
_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 >
σ(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.
Friedel pairs were merged as suggested by Checkcif. This results in a somewhat
low data-to-parameters ratio.
;
_reflns_number_total     1729
_reflns_number_gt     1422
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0554
_refine_ls_R_factor_gt     0.0419
_refine_ls_wR_factor_gt     0.1043
_refine_ls_wR_factor_ref     0.1103
_refine_ls_goodness_of_fit_ref     1.018
_refine_ls_restrained_S_all     1.018
_refine_ls_number_reflns     1729
_refine_ls_number_parameters     227
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
               'calc w = 1/[σ²(Fo²)+(0.0777P)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     0.269
_refine_diff_density_min     -0.219
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.046(10)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details     ?
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'
    'O' 'O' 0.0106 0.0060
                         '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'
_computing_data_collection     'COLLECT (Nonius, 1999)'
_computing_cell_refinement     'DENZO (Otwinowski & Minor, 1997)'
_computing_data_reduction     'DENZO (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SIR97 (Altomare et al.,  1994)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae et al.,
2006)
;
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
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 -0.1944(3) 0.32257(12) 1.0762(3) 0.0291(5) Uani d . 1 . .
    C C2 -0.0264(5) 0.28504(19) 1.0082(4) 0.0277(6) Uani d . 1 . .
    C C3 0.0331(4) 0.21694(18) 1.1014(4) 0.0268(6) Uani d . 1 . .
    C C4 -0.1035(5) 0.21197(18) 1.2452(4) 0.0291(6) Uani d . 1 . .
    C C5 -0.1210(5) 0.16029(18) 1.3889(4) 0.0326(7) Uani d . 1 . .
    H H5 -0.0289 0.1151 1.4099 0.039 Uiso calc R 1 . .
    C C6 -0.2773(5) 0.1771(2) 1.5001(4) 0.0372(7) Uani d . 1 . .
    H H6 -0.2906 0.1427 1.5996 0.045 Uiso calc R 1 . .
    C C7 -0.4161(6) 0.2427(2) 1.4713(5) 0.0364(7) Uani d . 1 . .
    H H7 -0.5229 0.2517 1.5495 0.044 Uiso calc R 1 . .
    C C8 -0.3994(5) 0.29529(19) 1.3283(4) 0.0320(7) Uani d . 1 . .
    H H8 -0.4924 0.3403 1.3057 0.038 Uiso calc R 1 . .
    C C9 -0.2383(5) 0.27746(18) 1.2220(4) 0.0279(6) Uani d . 1 . .
    C C10 0.0579(5) 0.32876(17) 0.8592(4) 0.0273(6) Uani d . 1 . .
    O O11 0.2357(3) 0.29930(13) 0.8088(3) 0.0337(5) Uani d . 1 . .
    O O12 -0.0338(3) 0.38930(13) 0.8012(3) 0.0324(5) Uani d . 1 . .
    C C13 0.1937(5) 0.15629(18) 1.0649(4) 0.0292(6) Uani d . 1 . .
    O O14 0.3351(3) 0.17217(13) 0.9513(3) 0.0327(5) Uani d . 1 . .
    H H14 0.295(6) 0.217(3) 0.870(6) 0.049 Uiso d . 1 . .
    O O15 0.1950(3) 0.09354(12) 1.1364(3) 0.0336(5) Uani d . 1 . .
    N N16 0.4894(4) 0.42962(15) 0.7505(4) 0.0264(5) Uani d . 1 . .
    H H16A 0.393(6) 0.387(2) 0.745(5) 0.040 Uiso d . 1 . .
    H H16B 0.645(7) 0.424(2) 0.804(5) 0.040 Uiso d . 1 . .
    H H16C 0.438(6) 0.470(2) 0.839(5) 0.040 Uiso d . 1 . .
    C C17 0.4405(5) 0.45689(17) 0.5500(4) 0.0245(6) Uani d . 1 . .
    C C18 0.2187(5) 0.44712(17) 0.4257(4) 0.0261(6) Uani d . 1 . .
    H H18 0.0972 0.4223 0.4692 0.031 Uiso calc R 1 . .
    C C19 0.1752(5) 0.47390(17) 0.2364(4) 0.0265(6) Uani d . 1 . .
    H H19 0.0234 0.4674 0.1501 0.032 Uiso calc R 1 . .
    C C20 0.3550(5) 0.51046(16) 0.1732(4) 0.0241(6) Uani d . 1 . .
    N N23 0.3133(4) 0.53619(15) -0.0210(3) 0.0270(5) Uani d . 1 . .
    H H23A 0.401(6) 0.573(3) -0.024(5) 0.041 Uiso d . 1 . .
    H H23B 0.155(6) 0.544(2) -0.074(5) 0.041 Uiso d . 1 . .
    C C21 0.5767(5) 0.51948(17) 0.2998(4) 0.0266(6) Uani d . 1 . .
    H H21 0.6989 0.5442 0.2568 0.032 Uiso calc R 1 . .
    C C22 0.6210(4) 0.49279(17) 0.4883(4) 0.0257(6) Uani d . 1 . .
    H H22 0.7730 0.4989 0.5746 0.031 Uiso calc R 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 C2 . 1.370(3) ?
    O1 C9 . 1.382(4) ?
    C2 C3 . 1.371(5) ?
    C2 C10 . 1.492(4) ?
    C3 C4 . 1.452(4) ?
    C3 C13 . 1.487(4) ?
    C4 C9 . 1.382(4) ?
    C4 C5 . 1.393(4) ?
    C5 C6 . 1.384(4) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.395(5) ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.398(5) ?
    C7 H7 . 0.9500 ?
    C8 C9 . 1.386(4) ?
    C8 H8 . 0.9500 ?
    C10 O12 . 1.216(4) ?
    C10 O11 . 1.290(3) ?
    C13 O15 . 1.215(4) ?
    C13 O14 . 1.325(4) ?
    O14 H14 . 0.97(5) ?
    N16 C17 . 1.466(4) ?
    N16 H16A . 0.93(4) ?
    N16 H16B . 0.90(4) ?
    N16 H16C . 1.05(4) ?
    C17 C18 . 1.383(4) ?
    C17 C22 . 1.393(4) ?
    C18 C19 . 1.391(4) ?
    C18 H18 . 0.9500 ?
    C19 C20 . 1.400(4) ?
    C19 H19 . 0.9500 ?
    C20 C21 . 1.388(4) ?
    C20 N23 . 1.418(4) ?
    N23 H23A . 0.83(4) ?
    N23 H23B . 0.92(4) ?
    C21 C22 . 1.385(4) ?
    C21 H21 . 0.9500 ?
    C22 H22 . 0.9500 ?
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 O1 C9 . . 106.0(2) ?
    O1 C2 C3 . . 111.5(3) ?
    O1 C2 C10 . . 113.5(3) ?
    C3 C2 C10 . . 134.9(3) ?
    C2 C3 C4 . . 106.1(3) ?
    C2 C3 C13 . . 129.5(3) ?
    C4 C3 C13 . . 124.3(3) ?
    C9 C4 C5 . . 119.1(3) ?
    C9 C4 C3 . . 105.3(3) ?
    C5 C4 C3 . . 135.6(3) ?
    C6 C5 C4 . . 117.6(3) ?
    C6 C5 H5 . . 121.2 ?
    C4 C5 H5 . . 121.2 ?
    C5 C6 C7 . . 122.4(3) ?
    C5 C6 H6 . . 118.8 ?
    C7 C6 H6 . . 118.8 ?
    C6 C7 C8 . . 120.7(3) ?
    C6 C7 H7 . . 119.7 ?
    C8 C7 H7 . . 119.7 ?
    C9 C8 C7 . . 115.5(3) ?
    C9 C8 H8 . . 122.2 ?
    C7 C8 H8 . . 122.2 ?
    C4 C9 O1 . . 111.1(2) ?
    C4 C9 C8 . . 124.7(3) ?
    O1 C9 C8 . . 124.2(3) ?
    O12 C10 O11 . . 125.0(3) ?
    O12 C10 C2 . . 119.8(2) ?
    O11 C10 C2 . . 115.1(3) ?
    O15 C13 O14 . . 120.6(3) ?
    O15 C13 C3 . . 121.0(3) ?
    O14 C13 C3 . . 118.3(3) ?
    C13 O14 H14 . . 116(2) ?
    C17 N16 H16A . . 105(2) ?
    C17 N16 H16B . . 112(2) ?
    H16A N16 H16B . . 117(4) ?
    C17 N16 H16C . . 110(2) ?
    H16A N16 H16C . . 108(3) ?
    H16B N16 H16C . . 104(3) ?
    C18 C17 C22 . . 121.0(3) ?
    C18 C17 N16 . . 120.3(2) ?
    C22 C17 N16 . . 118.7(2) ?
    C17 C18 C19 . . 119.5(2) ?
    C17 C18 H18 . . 120.3 ?
    C19 C18 H18 . . 120.3 ?
    C18 C19 C20 . . 120.0(3) ?
    C18 C19 H19 . . 120.0 ?
    C20 C19 H19 . . 120.0 ?
    C21 C20 C19 . . 119.7(3) ?
    C21 C20 N23 . . 120.0(2) ?
    C19 C20 N23 . . 120.2(2) ?
    C20 N23 H23A . . 109(3) ?
    C20 N23 H23B . . 111(2) ?
    H23A N23 H23B . . 115(3) ?
    C22 C21 C20 . . 120.5(3) ?
    C22 C21 H21 . . 119.8 ?
    C20 C21 H21 . . 119.8 ?
    C21 C22 C17 . . 119.3(2) ?
    C21 C22 H22 . . 120.4 ?
    C17 C22 H22 . . 120.4 ?
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
    O14 H14 O11 . 0.97(5) 1.53(5) 2.464(3) 160(4)
    N16 H16A O11 . 0.93(4) 1.91(4) 2.817(3) 164(3)
    N16 H16B O12 1_655 0.90(4) 1.98(4) 2.808(3) 153(3)
    N16 H16C N23 1_556 1.05(4) 1.80(4) 2.842(4) 173(3)
    N23 H23A O14 2_656 0.83(4) 2.30(4) 3.110(3) 166(3)
    N23 H23B O15 2_556 0.92(4) 2.16(4) 3.047(3) 162(3)
