##############################################################################
###                                                                        ###
###           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     2007-09-19
_journal_date_accepted     2008-01-15
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2008
_journal_volume     64
_journal_issue      3
_journal_page_first     o123
_journal_page_last     o127
_journal_paper_category     FO
_journal_coeditor_code     GZ3114
_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
Queensland 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
;
The 1:1 proton-transfer compounds of 4-(phenyldiazenyl)aniline (aniline yellow)
with 3-nitrophthalic, 4-nitrophthalic and 5-nitroisophthalic acids
;
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
;
    'David J. Young'
;
School of Biomolecular and Physical Sciences
Griffith University
Nathan
Queensland 4111
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
;
4-(phenyldiazenyl)anilinium 2-carboxy-6-nitrobenzoate
;
_chemical_name_common     '4-(phenylazo)anilinium hydrogen 3-nitrophthalate'
_chemical_formula_moiety     'C12 H12 N3 + , C8 H4 N O6 -'
_chemical_formula_sum     'C20 H16 N4 O6'
_chemical_formula_iupac     'C12 H12 N3 + , C8 H4 N O6 -'
_chemical_formula_weight     408.37
_chemical_melting_point     441
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y+1/2, z+1/2'
_cell_length_a     17.873(2)
_cell_length_b     7.9729(10)
_cell_length_c     13.3054(16)
_cell_angle_alpha     90.00
_cell_angle_beta     98.198(2)
_cell_angle_gamma     90.00
_cell_volume     1876.6(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3539
_cell_measurement_theta_min     2.30
_cell_measurement_theta_max     27.23
_cell_measurement_temperature     130(2)
_exptl_crystal_description     'needle cut from block'
_exptl_crystal_colour     'orange--yellow'
_exptl_crystal_size_max     0.55
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     1.445
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     848
_exptl_absorpt_coefficient_mu     0.109
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 1999)'
_exptl_absorpt_correction_T_min     0.88
_exptl_absorpt_correction_T_max     0.99
_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     9511
_diffrn_reflns_av_R_equivalents     0.0228
_diffrn_reflns_av_sigmaI/netI     0.0273
_diffrn_reflns_theta_min     1.15
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -21
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_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     3306
_reflns_number_gt     2888
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0458
_refine_ls_R_factor_gt     0.0392
_refine_ls_wR_factor_gt     0.0966
_refine_ls_wR_factor_ref     0.1001
_refine_ls_goodness_of_fit_ref     1.043
_refine_ls_restrained_S_all     1.043
_refine_ls_number_reflns     3306
_refine_ls_number_parameters     320
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0506P)²+0.5876P] 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     0.213
_refine_diff_density_min     -0.179
_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     '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 N1 0.16652(16) 0.1941(3) 0.61705(14) 0.0343(8) Uani . . 0.775(8)
    N N4 0.42531(7) 0.58845(17) 0.58646(10) 0.0214(4) Uani . . 1.000
    N N11 0.17087(14) 0.0416(4) 0.59911(15) 0.0355(8) Uani . . 0.775(8)
    C C1 0.23519(19) 0.2852(5) 0.61061(19) 0.0286(9) Uani . . 0.775(8)
    C C2 0.3059(2) 0.2105(4) 0.6120(2) 0.0286(9) Uani . . 0.775(8)
    C C3 0.3675(2) 0.3120(5) 0.6047(3) 0.0298(9) Uani . . 0.775(8)
    C C4 0.3591(3) 0.4821(5) 0.5958(4) 0.0212(11) Uani . . 0.775(8)
    C C5 0.28978(17) 0.5562(7) 0.5953(3) 0.0250(9) Uani . . 0.775(8)
    C C6 0.22771(15) 0.4571(6) 0.6042(2) 0.0308(9) Uani . . 0.775(8)
    C C11 0.10308(18) -0.0511(6) 0.6070(2) 0.0355(9) Uani . . 0.775(8)
    C C21 0.10199(19) -0.2117(6) 0.5708(3) 0.0580(13) Uani . . 0.775(8)
    C C31 0.0405(3) -0.3127(8) 0.5766(5) 0.0727(16) Uani . . 0.775(8)
    C C41 -0.02034(17) -0.2549(4) 0.6186(4) 0.0477(13) Uani . . 0.775(8)
    C C51 -0.0195(2) -0.0934(5) 0.6546(5) 0.0567(13) Uani . . 0.775(8)
    C C61 0.0419(2) 0.0109(4) 0.6479(3) 0.0463(10) Uani . . 0.775(8)
    C C1' 0.2519(5) 0.2387(12) 0.6042(6) 0.017(3) Uiso . G 0.225(8)
    C C2' 0.3263(6) 0.1848(10) 0.6096(7) 0.030(4) Uiso . G 0.225(8)
    C C3' 0.3837(5) 0.3007(14) 0.6037(10) 0.027(3) Uiso . G 0.225(8)
    C C4' 0.3666(6) 0.4703(12) 0.5925(13) 0.021(6) Uiso . G 0.225(8)
    C C5' 0.2921(7) 0.5241(10) 0.5872(13) 0.042(7) Uiso . G 0.225(8)
    C C6' 0.2348(5) 0.4083(13) 0.5930(8) 0.030(4) Uiso . G 0.225(8)
    C C11' 0.0830(5) 0.0086(12) 0.6148(6) 0.024(2) Uiso . G 0.225(8)
    C C21' 0.0932(5) -0.1467(14) 0.5712(7) 0.033(3) Uiso . G 0.225(8)
    C C31' 0.0409(8) -0.2742(11) 0.5765(10) 0.050(5) Uiso . G 0.225(8)
    C C41' -0.0217(7) -0.2464(15) 0.6255(13) 0.068(9) Uiso . G 0.225(8)
    C C51' -0.0320(6) -0.0911(17) 0.6690(11) 0.046(5) Uiso . G 0.225(8)
    C C61' 0.0204(6) 0.0363(12) 0.6637(7) 0.040(4) Uiso . G 0.225(8)
    N N1' 0.2004(6) 0.1034(11) 0.6076(5) 0.027(2) Uiso . . 0.225(8)
    N N11' 0.1326(6) 0.1493(11) 0.6172(5) 0.031(2) Uiso . . 0.225(8)
    O O11A 0.46342(7) 1.15633(15) 0.40898(9) 0.0386(4) Uani . . 1.000
    O O12A 0.48397(6) 0.95224(13) 0.30108(8) 0.0244(3) Uani . . 1.000
    O O21A 0.40177(6) 0.63962(12) 0.22058(7) 0.0219(3) Uani . . 1.000
    O O22A 0.44206(6) 0.60762(13) 0.38640(7) 0.0229(3) Uani . . 1.000
    O O31A 0.28656(6) 0.47541(14) 0.32131(9) 0.0340(4) Uani . . 1.000
    O O32A 0.17511(6) 0.55324(16) 0.34617(10) 0.0403(4) Uani . . 1.000
    N N3A 0.24065(7) 0.58335(17) 0.33526(10) 0.0260(4) Uani . . 1.000
    C C1A 0.36304(8) 0.96762(19) 0.35585(11) 0.0234(4) Uani . . 1.000
    C C2A 0.34187(8) 0.79910(18) 0.33696(10) 0.0200(4) Uani . . 1.000
    C C3A 0.26627(8) 0.75997(19) 0.34180(11) 0.0233(5) Uani . . 1.000
    C C4A 0.21249(9) 0.8794(2) 0.35647(13) 0.0304(5) Uani . . 1.000
    C C5A 0.23415(9) 1.0444(2) 0.36972(13) 0.0328(5) Uani . . 1.000
    C C6A 0.30919(9) 1.0872(2) 0.37215(12) 0.0288(5) Uani . . 1.000
    C C11A 0.44208(9) 1.03425(19) 0.35914(11) 0.0247(5) Uani . . 1.000
    C C21A 0.39964(8) 0.66948(18) 0.31315(11) 0.0197(4) Uani . . 1.000
    H H61 0.04180 0.12350 0.67130 0.0560 Uiso calc . 0.775(8)
    H H2 0.31150 0.09230 0.61790 0.0340 Uiso calc . 0.775(8)
    H H3 0.41610 0.26330 0.60600 0.0360 Uiso calc . 0.775(8)
    H H5 0.28450 0.67440 0.58900 0.0300 Uiso calc . 0.775(8)
    H H6 0.17970 0.50750 0.60590 0.0370 Uiso calc . 0.775(8)
    H H21 0.14380 -0.25350 0.54170 0.0700 Uiso calc . 0.775(8)
    H H31 0.04010 -0.42410 0.55120 0.0870 Uiso calc . 0.775(8)
    H H41 -0.06250 -0.32570 0.62280 0.0570 Uiso calc . 0.775(8)
    H H42 0.4226(10) 0.683(3) 0.6239(15) 0.038(5) Uiso . . 1.000
    H H43 0.4724(12) 0.529(3) 0.6100(16) 0.049(6) Uiso . . 1.000
    H H44 0.4269(10) 0.618(2) 0.5182(16) 0.041(5) Uiso . . 1.000
    H H51 -0.06120 -0.05270 0.68430 0.0680 Uiso calc . 0.775(8)
    H H2' 0.33800 0.06890 0.61720 0.0350 Uiso calc . 0.225(8)
    H H3' 0.43450 0.26390 0.60730 0.0280 Uiso calc . 0.225(8)
    H H5' 0.28050 0.64010 0.57950 0.0510 Uiso calc . 0.225(8)
    H H6' 0.18390 0.44510 0.58940 0.0360 Uiso calc . 0.225(8)
    H H21' 0.13600 -0.16570 0.53770 0.0390 Uiso calc . 0.225(8)
    H H31' 0.04790 -0.38030 0.54670 0.0600 Uiso calc . 0.225(8)
    H H41' -0.05730 -0.33300 0.63270 0.0820 Uiso calc . 0.225(8)
    H H51' -0.07480 -0.07220 0.70250 0.0550 Uiso calc . 0.225(8)
    H H61' 0.01330 0.14240 0.69350 0.0480 Uiso calc . 0.225(8)
    H H4A 0.16130 0.84770 0.35730 0.0360 Uiso calc R 1.000
    H H5A 0.19760 1.12840 0.37720 0.0390 Uiso calc R 1.000
    H H6A 0.32440 1.20030 0.38520 0.0350 Uiso calc R 1.000
    H H12A 0.5272(13) 1.018(3) 0.2966(17) 0.061(7) 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
    O11A C11A . . 1.2085(19) no
    O12A C11A . . 1.3228(19) no
    O21A C21A . . 1.2604(17) no
    O22A C21A . . 1.2479(18) no
    O31A N3A . . 1.2214(17) no
    O32A N3A . . 1.2245(17) no
    O12A H12A . . 0.94(2) no
    N1 N11 . . 1.244(4) no
    N1 C1 . . 1.439(5) no
    N1' N11' . . 1.290(15) no
    N1' C1' . . 1.423(13) no
    N4 C4' . . 1.421(10) no
    N4 C4 . . 1.475(5) no
    N11 C11 . . 1.436(5) no
    N11' C11' . . 1.427(13) no
    N4 H44 . . 0.94(2) no
    N4 H42 . . 0.91(2) no
    N4 H43 . . 0.98(2) no
    N3A C3A . . 1.480(2) no
    C1 C2 . . 1.395(5) no
    C1 C6 . . 1.379(6) no
    C1' C2' . . 1.3895 no
    C1' C6' . . 1.3896 no
    C2 C3 . . 1.381(5) no
    C2' C3' . . 1.3912 no
    C3 C4 . . 1.368(6) no
    C3' C4' . . 1.3896 no
    C4 C5 . . 1.372(6) no
    C4' C5' . . 1.3911 no
    C5 C6 . . 1.381(5) no
    C5' C6' . . 1.3891 no
    C11 C61 . . 1.381(5) no
    C11 C21 . . 1.367(7) no
    C11' C61' . . 1.3898 no
    C11' C21' . . 1.3903 no
    C21 C31 . . 1.374(7) no
    C21' C31' . . 1.3896 no
    C31 C41 . . 1.371(7) no
    C31' C41' . . 1.3907 no
    C41 C51 . . 1.373(6) no
    C41' C51' . . 1.3901 no
    C51 C61 . . 1.390(5) no
    C51' C61' . . 1.3902 no
    C2 H2 . . 0.9500 no
    C2' H2' . . 0.9500 no
    C3 H3 . . 0.9500 no
    C3' H3' . . 0.9500 no
    C5 H5 . . 0.9500 no
    C5' H5' . . 0.9500 no
    C6 H6 . . 0.9500 no
    C6' H6' . . 0.9500 no
    C21 H21 . . 0.9500 no
    C21' H21' . . 0.9500 no
    C31 H31 . . 0.9500 no
    C31' H31' . . 0.9500 no
    C41 H41 . . 0.9500 no
    C41' H41' . . 0.9500 no
    C51 H51 . . 0.9500 no
    C51' H51' . . 0.9500 no
    C61 H61 . . 0.9500 no
    C61' H61' . . 0.9500 no
    C1A C2A . . 1.409(2) no
    C1A C11A . . 1.504(2) no
    C1A C6A . . 1.394(2) no
    C2A C3A . . 1.397(2) no
    C2A C21A . . 1.526(2) no
    C3A C4A . . 1.386(2) no
    C4A C5A . . 1.376(2) no
    C5A C6A . . 1.380(2) no
    C4A H4A . . 0.9500 no
    C5A H5A . . 0.9500 no
    C6A H6A . . 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
    C11A O12A H12A . . . 107.4(14) no
    N11 N1 C1 . . . 113.9(3) no
    N11' N1' C1' . . . 114.2(8) no
    N1 N11 C11 . . . 114.4(3) no
    N1' N11' C11' . . . 111.4(8) no
    C4 N4 H44 . . . 111.1(11) no
    C4' N4 H44 . . . 110.1(13) no
    C4' N4 H42 . . . 114.9(13) no
    H43 N4 H44 . . . 106.7(16) no
    C4 N4 H43 . . . 111.0(14) no
    H42 N4 H44 . . . 109.4(16) no
    C4 N4 H42 . . . 108.9(12) no
    C4' N4 H43 . . . 105.6(14) no
    H42 N4 H43 . . . 109.7(18) no
    O31A N3A O32A . . . 123.69(14) no
    O32A N3A C3A . . . 118.23(13) no
    O31A N3A C3A . . . 118.07(12) no
    C2 C1 C6 . . . 120.3(3) no
    N1 C1 C6 . . . 115.4(3) no
    N1 C1 C2 . . . 124.2(3) no
    C2' C1' C6' . . . 120.05 no
    N1' C1' C6' . . . 127.4(9) no
    N1' C1' C2' . . . 112.5(8) no
    C1 C2 C3 . . . 118.6(3) no
    C1' C2' C3' . . . 119.97 no
    C2 C3 C4 . . . 120.6(4) no
    C2' C3' C4' . . . 119.98 no
    N4 C4 C5 . . . 119.1(4) no
    C3 C4 C5 . . . 121.0(4) no
    N4 C4 C3 . . . 119.9(4) no
    C3' C4' C5' . . . 119.98 no
    N4 C4' C5' . . . 120.1(8) no
    N4 C4' C3' . . . 119.9(9) no
    C4 C5 C6 . . . 119.3(5) no
    C4' C5' C6' . . . 120.01 no
    C1 C6 C5 . . . 120.2(3) no
    C1' C6' C5' . . . 120.00 no
    N11 C11 C21 . . . 115.2(3) no
    N11 C11 C61 . . . 124.7(4) no
    C21 C11 C61 . . . 120.1(3) no
    C21' C11' C61' . . . 119.94 no
    N11' C11' C21' . . . 126.3(8) no
    N11' C11' C61' . . . 113.8(8) no
    C11 C21 C31 . . . 120.0(4) no
    C11' C21' C31' . . . 120.08 no
    C21 C31 C41 . . . 120.9(5) no
    C21' C31' C41' . . . 119.95 no
    C31 C41 C51 . . . 119.2(4) no
    C31' C41' C51' . . . 120.02 no
    C41 C51 C61 . . . 120.5(4) no
    C41' C51' C61' . . . 119.97 no
    C11 C61 C51 . . . 119.2(4) no
    C11' C61' C51' . . . 120.05 no
    C3 C2 H2 . . . 121.00 no
    C1 C2 H2 . . . 121.00 no
    C3' C2' H2' . . . 120.00 no
    C1' C2' H2' . . . 120.00 no
    C2 C3 H3 . . . 120.00 no
    C4 C3 H3 . . . 120.00 no
    C2' C3' H3' . . . 120.00 no
    C4' C3' H3' . . . 120.00 no
    C4 C5 H5 . . . 120.00 no
    C6 C5 H5 . . . 120.00 no
    C4' C5' H5' . . . 120.00 no
    C6' C5' H5' . . . 120.00 no
    C1 C6 H6 . . . 120.00 no
    C5 C6 H6 . . . 120.00 no
    C1' C6' H6' . . . 120.00 no
    C5' C6' H6' . . . 120.00 no
    C31 C21 H21 . . . 120.00 no
    C11 C21 H21 . . . 120.00 no
    C31' C21' H21' . . . 120.00 no
    C11' C21' H21' . . . 120.00 no
    C21 C31 H31 . . . 120.00 no
    C41 C31 H31 . . . 120.00 no
    C41' C31' H31' . . . 120.00 no
    C21' C31' H31' . . . 120.00 no
    C51 C41 H41 . . . 120.00 no
    C31 C41 H41 . . . 120.00 no
    C51' C41' H41' . . . 118.00 no
    C31' C41' H41' . . . 122.00 no
    C61 C51 H51 . . . 120.00 no
    C41 C51 H51 . . . 120.00 no
    C41' C51' H51' . . . 120.00 no
    C61' C51' H51' . . . 120.00 no
    C51 C61 H61 . . . 120.00 no
    C11 C61 H61 . . . 120.00 no
    C11' C61' H61' . . . 120.00 no
    C51' C61' H61' . . . 120.00 no
    C2A C1A C11A . . . 124.70(13) no
    C6A C1A C11A . . . 114.87(13) no
    C2A C1A C6A . . . 120.43(14) no
    C1A C2A C21A . . . 120.70(13) no
    C3A C2A C21A . . . 123.09(13) no
    C1A C2A C3A . . . 116.21(13) no
    N3A C3A C2A . . . 120.20(13) no
    N3A C3A C4A . . . 116.55(13) no
    C2A C3A C4A . . . 123.20(14) no
    C3A C4A C5A . . . 119.13(15) no
    C4A C5A C6A . . . 119.63(15) no
    C1A C6A C5A . . . 121.18(15) no
    O11A C11A C1A . . . 121.47(14) no
    O12A C11A C1A . . . 114.58(13) no
    O11A C11A O12A . . . 123.91(15) no
    O21A C21A C2A . . . 116.52(12) no
    O22A C21A C2A . . . 117.34(12) no
    O21A C21A O22A . . . 126.08(13) no
    C3A C4A H4A . . . 120.00 no
    C5A C4A H4A . . . 120.00 no
    C4A C5A H5A . . . 120.00 no
    C6A C5A H5A . . . 120.00 no
    C1A C6A H6A . . . 119.00 no
    C5A C6A H6A . . . 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
    C1 N1 N11 C11 . . . . 179.0(2) no
    N11 N1 C1 C2 . . . . -16.8(3) no
    N11 N1 C1 C6 . . . . 164.2(2) no
    N1 N11 C11 C21 . . . . 169.1(3) no
    N1 N11 C11 C61 . . . . -11.2(4) no
    O31A N3A C3A C4A . . . . 179.26(14) no
    O31A N3A C3A C2A . . . . -3.1(2) no
    O32A N3A C3A C2A . . . . 175.50(14) no
    O32A N3A C3A C4A . . . . -2.2(2) no
    N1 C1 C6 C5 . . . . -178.5(3) no
    N1 C1 C2 C3 . . . . 179.6(3) no
    C6 C1 C2 C3 . . . . -1.3(4) no
    C2 C1 C6 C5 . . . . 2.4(4) no
    C1 C2 C3 C4 . . . . -0.3(5) no
    C2 C3 C4 C5 . . . . 0.9(7) no
    C2 C3 C4 N4 . . . . -179.0(3) no
    N4 C4 C5 C6 . . . . -179.9(3) no
    C3 C4 C5 C6 . . . . 0.2(7) no
    C4 C5 C6 C1 . . . . -1.8(5) no
    C61 C11 C21 C31 . . . . -1.1(6) no
    N11 C11 C61 C51 . . . . -177.7(4) no
    C21 C11 C61 C51 . . . . 2.0(6) no
    N11 C11 C21 C31 . . . . 178.6(4) no
    C11 C21 C31 C41 . . . . -0.1(8) no
    C21 C31 C41 C51 . . . . 0.4(9) no
    C31 C41 C51 C61 . . . . 0.5(8) no
    C41 C51 C61 C11 . . . . -1.7(7) no
    C6A C1A C2A C21A . . . . 176.53(13) no
    C11A C1A C2A C3A . . . . 177.04(13) no
    C6A C1A C2A C3A . . . . -3.7(2) no
    C2A C1A C11A O12A . . . . 29.2(2) no
    C6A C1A C11A O11A . . . . 27.7(2) no
    C6A C1A C11A O12A . . . . -150.09(14) no
    C11A C1A C6A C5A . . . . 179.00(14) no
    C11A C1A C2A C21A . . . . -2.8(2) no
    C2A C1A C6A C5A . . . . -0.4(2) no
    C2A C1A C11A O11A . . . . -152.97(15) no
    C1A C2A C3A N3A . . . . -172.71(13) no
    C1A C2A C21A O22A . . . . 81.36(17) no
    C3A C2A C21A O21A . . . . 84.13(17) no
    C3A C2A C21A O22A . . . . -98.41(17) no
    C1A C2A C3A C4A . . . . 4.8(2) no
    C21A C2A C3A N3A . . . . 7.1(2) no
    C21A C2A C3A C4A . . . . -175.40(14) no
    C1A C2A C21A O21A . . . . -96.10(16) no
    N3A C3A C4A C5A . . . . 175.82(14) no
    C2A C3A C4A C5A . . . . -1.8(2) no
    C3A C4A C5A C6A . . . . -2.5(3) no
    C4A C5A C6A C1A . . . . 3.6(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
    O12A H12A O21A 2_655 0.94(2) 1.64(2) 2.5794(15) 175(2) yes
    N4 H42 O11A 3_676 0.91(2) 2.50(2) 2.8399(18) 102.8(13) yes
    N4 H42 O21A 4_565 0.91(2) 1.98(2) 2.8768(17) 167.7(19) yes
    N4 H43 O22A 3_666 0.98(2) 1.87(2) 2.8194(17) 162.3(19) yes
    N4 H43 O12A 4_565 0.98(2) 2.53(2) 2.9164(17) 103.7(14) yes
    N4 H44 O22A . 0.94(2) 1.81(2) 2.7250(16) 161.7(15) yes
    C6A H6A O31A 1_565 0.95 2.41 3.182(2) 138 yes
data_II
_audit_creation_method     'SHELXL97 (Sheldrick, 2008)'
_chemical_name_systematic
;
4-(phenyldiazenyl)anilinium 2-carboxy-4-nitrobenzoate
;
_chemical_name_common     '4-phenylazoanilinium hydrogen 4-nitrophthalate'
_chemical_formula_moiety     'C12 H12 N3 + , C8 H4 N O6 -'
_chemical_formula_sum     'C20 H16 N4 O6'
_chemical_formula_iupac     'C12 H12 N3 + , C8 H4 N O6 -'
_chemical_formula_weight     408.37
_chemical_melting_point        .511E-305
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'C 2'
_symmetry_space_group_name_Hall     'C 2y'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y, -z'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z'
_cell_length_a     12.950(3)
_cell_length_b     7.5571(18)
_cell_length_c     19.364(5)
_cell_angle_alpha     90.00
_cell_angle_beta     100.371(5)
_cell_angle_gamma     90.00
_cell_volume     1864.1(8)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1103
_cell_measurement_theta_min     3.13
_cell_measurement_theta_max     22.82
_cell_measurement_temperature     130(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     orange-yellow
_exptl_crystal_size_max     0.45
_exptl_crystal_size_mid     0.05
_exptl_crystal_size_min     0.05
_exptl_crystal_density_diffrn     1.455
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     848
_exptl_absorpt_coefficient_mu     0.110
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 1999)'
_exptl_absorpt_correction_T_min     0.98
_exptl_absorpt_correction_T_max     0.99
_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     4865
_diffrn_reflns_av_R_equivalents     0.0347
_diffrn_reflns_av_sigmaI/netI     0.0599
_diffrn_reflns_theta_min     1.07
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -22
_diffrn_reflns_limit_l_max     20
_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     1766
_reflns_number_gt     1564
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0545
_refine_ls_R_factor_gt     0.0459
_refine_ls_wR_factor_gt     0.0923
_refine_ls_wR_factor_ref     0.0961
_refine_ls_goodness_of_fit_ref     1.041
_refine_ls_restrained_S_all     1.041
_refine_ls_number_reflns     1766
_refine_ls_number_parameters     270
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     noref
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
               'calc w = 1/[σ²(Fo²)+(0.0409P)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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.255
_refine_diff_density_min     -0.214
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     ?
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     '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 N1 0.2479(2) 0.0790(4) 0.29899(14) 0.0362(10) Uani . . 1.000
    N N4 0.11130(18) 0.5521(3) 0.07349(12) 0.0201(8) Uani . . 1.000
    N N11 0.2892(2) 0.1422(4) 0.35540(15) 0.0351(10) Uani . . 1.000
    C C1 0.2144(2) 0.2131(4) 0.24523(16) 0.0274(11) Uani . . 1.000
    C C2 0.2039(2) 0.3941(4) 0.25726(16) 0.0278(10) Uani . . 1.000
    C C3 0.1695(2) 0.5059(4) 0.20060(15) 0.0260(10) Uani . . 1.000
    C C4 0.1459(2) 0.4358(4) 0.13358(15) 0.0204(9) Uani . . 1.000
    C C5 0.1566(2) 0.2568(4) 0.12197(15) 0.0239(10) Uani . . 1.000
    C C6 0.1901(2) 0.1456(4) 0.17809(16) 0.0265(10) Uani . . 1.000
    C C11 0.3202(2) 0.0058(4) 0.40853(17) 0.0323(11) Uani . . 1.000
    C C21 0.3574(2) 0.0680(5) 0.47489(17) 0.0373(11) Uani . . 1.000
    C C31 0.3850(3) -0.0494(5) 0.52975(17) 0.0367(11) Uani . . 1.000
    C C41 0.3783(2) -0.2291(5) 0.51785(17) 0.0362(11) Uani . . 1.000
    C C51 0.3428(2) -0.2937(5) 0.45042(17) 0.0363(11) Uani . . 1.000
    C C61 0.3125(2) -0.1760(5) 0.39561(16) 0.0357(11) Uani . . 1.000
    O O11A 0.41526(14) 0.8566(2) 0.05343(9) 0.0230(7) Uani . . 1.000
    O O12A 0.25676(14) 0.8309(3) 0.08423(9) 0.0199(6) Uani . . 1.000
    O O21A 0.31481(14) 0.4916(2) 0.02563(10) 0.0209(6) Uani . . 1.000
    O O22A 0.42168(15) 0.2602(3) 0.05663(10) 0.0271(7) Uani . . 1.000
    O O41A 0.53126(19) 0.1819(3) 0.31060(11) 0.0431(9) Uani . . 1.000
    O O42A 0.53465(19) 0.4019(3) 0.38214(11) 0.0408(9) Uani . . 1.000
    N N4A 0.5181(2) 0.3399(4) 0.32290(13) 0.0297(9) Uani . . 1.000
    C C1A 0.3989(2) 0.6736(4) 0.15072(14) 0.0173(9) Uani . . 1.000
    C C2A 0.4146(2) 0.4903(4) 0.14021(14) 0.0184(9) Uani . . 1.000
    C C3A 0.4541(2) 0.3839(4) 0.19709(14) 0.0207(10) Uani . . 1.000
    C C4A 0.4782(2) 0.4568(4) 0.26329(15) 0.0362(11) Uani . . 1.000
    C C5A 0.4646(2) 0.6362(4) 0.27563(15) 0.0235(9) Uani . . 1.000
    C C6A 0.4257(2) 0.7418(4) 0.21851(14) 0.0217(9) Uani . . 1.000
    C C11A 0.3551(2) 0.7957(3) 0.09052(14) 0.0184(9) Uani . . 1.000
    C C21A 0.3846(2) 0.4033(4) 0.06952(14) 0.0176(9) Uani . . 1.000
    H H2 0.21970 0.43930 0.30260 0.0330 Uiso calc R 1.000
    H H3 0.16250 0.62670 0.20770 0.0310 Uiso calc R 1.000
    H H5 0.14140 0.21160 0.07660 0.0290 Uiso calc R 1.000
    H H6 0.19630 0.02480 0.17060 0.0320 Uiso calc R 1.000
    H H21 0.36400 0.18920 0.48290 0.0450 Uiso calc R 1.000
    H H31 0.40840 -0.00690 0.57490 0.0440 Uiso calc R 1.000
    H H41 0.39750 -0.30740 0.55500 0.0430 Uiso calc R 1.000
    H H42 0.041 0.603 0.0728 0.043 Uiso . . 1.000
    H H43 0.103 0.490 0.0322 0.057 Uiso . . 1.000
    H H44 0.160 0.640 0.0730 0.040 Uiso . . 1.000
    H H51 0.33940 -0.41500 0.44220 0.0440 Uiso calc R 1.000
    H H61 0.28720 -0.21780 0.35060 0.0430 Uiso calc R 1.000
    H H3A 0.46420 0.26370 0.19060 0.0250 Uiso calc R 1.000
    H H5A 0.48120 0.68330 0.32060 0.0280 Uiso calc R 1.000
    H H6A 0.41700 0.86220 0.22550 0.0260 Uiso calc R 1.000
    H H21A 0.288 0.434 -0.014 0.025 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
    O11A C11A . . 1.239(3) no
    O12A C11A . . 1.285(3) no
    O21A C21A . . 1.307(3) no
    O22A C21A . . 1.227(4) no
    O41A N4A . . 1.235(4) no
    O42A N4A . . 1.222(3) no
    O21A H21A . . 0.90 no
    N1 C1 . . 1.462(4) no
    N1 N11 . . 1.224(4) no
    N4 C4 . . 1.463(4) no
    N11 C11 . . 1.461(4) no
    N4 H43 . . 0.92 no
    N4 H44 . . 0.92 no
    N4 H42 . . 0.99 no
    N4A C4A . . 1.471(4) no
    C1 C6 . . 1.379(4) no
    C1 C2 . . 1.398(4) no
    C2 C3 . . 1.393(4) no
    C3 C4 . . 1.384(4) no
    C4 C5 . . 1.382(4) no
    C5 C6 . . 1.380(4) no
    C11 C21 . . 1.372(5) no
    C11 C61 . . 1.397(5) no
    C21 C31 . . 1.381(5) no
    C31 C41 . . 1.378(5) no
    C41 C51 . . 1.392(5) no
    C51 C61 . . 1.386(5) no
    C2 H2 . . 0.9300 no
    C3 H3 . . 0.9300 no
    C5 H5 . . 0.9300 no
    C6 H6 . . 0.9300 no
    C21 H21 . . 0.9300 no
    C31 H31 . . 0.9300 no
    C41 H41 . . 0.9300 no
    C51 H51 . . 0.9300 no
    C61 H61 . . 0.9300 no
    C1A C2A . . 1.420(4) no
    C1A C11A . . 1.515(4) no
    C1A C6A . . 1.395(4) no
    C2A C3A . . 1.385(4) no
    C2A C21A . . 1.505(4) no
    C3A C4A . . 1.379(4) no
    C4A C5A . . 1.393(4) no
    C5A C6A . . 1.383(4) no
    C3A H3A . . 0.9300 no
    C5A H5A . . 0.9300 no
    C6A H6A . . 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
    C21A O21A H21A . . . 115 no
    N11 N1 C1 . . . 113.0(3) no
    N1 N11 C11 . . . 112.0(3) no
    H43 N4 H44 . . . 110 no
    C4 N4 H44 . . . 109.3 no
    C4 N4 H42 . . . 113.3 no
    C4 N4 H43 . . . 111 no
    H42 N4 H43 . . . 103 no
    H42 N4 H44 . . . 111 no
    O41A N4A O42A . . . 123.0(3) no
    O41A N4A C4A . . . 118.1(2) no
    O42A N4A C4A . . . 118.9(3) no
    C2 C1 C6 . . . 120.4(3) no
    N1 C1 C6 . . . 113.8(3) no
    N1 C1 C2 . . . 125.8(3) no
    C1 C2 C3 . . . 119.3(3) no
    C2 C3 C4 . . . 119.5(3) no
    N4 C4 C5 . . . 118.9(2) no
    C3 C4 C5 . . . 121.0(3) no
    N4 C4 C3 . . . 120.0(3) no
    C4 C5 C6 . . . 119.6(3) no
    C1 C6 C5 . . . 120.2(3) no
    N11 C11 C21 . . . 115.1(3) no
    C21 C11 C61 . . . 120.4(3) no
    N11 C11 C61 . . . 124.5(3) no
    C11 C21 C31 . . . 119.9(3) no
    C21 C31 C41 . . . 120.3(3) no
    C31 C41 C51 . . . 120.2(3) no
    C41 C51 C61 . . . 119.6(3) no
    C11 C61 C51 . . . 119.5(3) no
    C1 C2 H2 . . . 120.00 no
    C3 C2 H2 . . . 120.00 no
    C2 C3 H3 . . . 120.00 no
    C4 C3 H3 . . . 120.00 no
    C6 C5 H5 . . . 120.00 no
    C4 C5 H5 . . . 120.00 no
    C5 C6 H6 . . . 120.00 no
    C1 C6 H6 . . . 120.00 no
    C31 C21 H21 . . . 120.00 no
    C11 C21 H21 . . . 120.00 no
    C21 C31 H31 . . . 120.00 no
    C41 C31 H31 . . . 120.00 no
    C31 C41 H41 . . . 120.00 no
    C51 C41 H41 . . . 120.00 no
    C61 C51 H51 . . . 120.00 no
    C41 C51 H51 . . . 120.00 no
    C11 C61 H61 . . . 120.00 no
    C51 C61 H61 . . . 120.00 no
    C2A C1A C11A . . . 121.8(2) no
    C6A C1A C11A . . . 119.6(3) no
    C2A C1A C6A . . . 118.5(3) no
    C1A C2A C21A . . . 122.4(2) no
    C3A C2A C21A . . . 117.9(3) no
    C1A C2A C3A . . . 119.6(3) no
    C2A C3A C4A . . . 119.8(3) no
    N4A C4A C3A . . . 118.6(3) no
    C3A C4A C5A . . . 122.3(3) no
    N4A C4A C5A . . . 119.2(3) no
    C4A C5A C6A . . . 117.6(3) no
    C1A C6A C5A . . . 122.2(3) no
    O11A C11A C1A . . . 119.0(2) no
    O12A C11A C1A . . . 115.2(2) no
    O11A C11A O12A . . . 125.7(2) no
    O21A C21A C2A . . . 113.8(2) no
    O22A C21A C2A . . . 121.6(2) no
    O21A C21A O22A . . . 124.6(2) no
    C2A C3A H3A . . . 120.00 no
    C4A C3A H3A . . . 120.00 no
    C4A C5A H5A . . . 121.00 no
    C6A C5A H5A . . . 121.00 no
    C1A C6A H6A . . . 119.00 no
    C5A C6A H6A . . . 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
    C1 N1 N11 C11 . . . . 179.0(2) no
    N11 N1 C1 C2 . . . . -15.5(4) no
    N11 N1 C1 C6 . . . . 166.0(3) no
    N1 N11 C11 C21 . . . . -173.7(3) no
    N1 N11 C11 C61 . . . . 5.3(4) no
    O41A N4A C4A C3A . . . . 2.2(4) no
    O41A N4A C4A C5A . . . . -178.8(3) no
    O42A N4A C4A C3A . . . . -176.4(3) no
    O42A N4A C4A C5A . . . . 2.7(4) no
    C6 C1 C2 C3 . . . . -0.6(4) no
    N1 C1 C6 C5 . . . . 179.6(2) no
    N1 C1 C2 C3 . . . . -179.0(3) no
    C2 C1 C6 C5 . . . . 1.0(4) no
    C1 C2 C3 C4 . . . . 0.3(4) no
    C2 C3 C4 C5 . . . . -0.4(4) no
    C2 C3 C4 N4 . . . . -179.0(2) no
    C3 C4 C5 C6 . . . . 0.8(4) no
    N4 C4 C5 C6 . . . . 179.4(2) no
    C4 C5 C6 C1 . . . . -1.1(4) no
    N11 C11 C21 C31 . . . . 177.4(3) no
    C61 C11 C21 C31 . . . . -1.6(4) no
    N11 C11 C61 C51 . . . . -179.0(3) no
    C21 C11 C61 C51 . . . . 0.0(4) no
    C11 C21 C31 C41 . . . . 1.9(5) no
    C21 C31 C41 C51 . . . . -0.5(5) no
    C31 C41 C51 C61 . . . . -1.1(4) no
    C41 C51 C61 C11 . . . . 1.4(4) no
    C6A C1A C2A C3A . . . . 1.1(4) no
    C6A C1A C2A C21A . . . . 177.8(2) no
    C11A C1A C2A C3A . . . . -179.5(2) no
    C11A C1A C2A C21A . . . . -2.8(4) no
    C2A C1A C6A C5A . . . . -1.5(4) no
    C11A C1A C6A C5A . . . . 179.1(2) no
    C2A C1A C11A O11A . . . . -82.4(3) no
    C2A C1A C11A O12A . . . . 99.6(3) no
    C6A C1A C11A O11A . . . . 97.0(3) no
    C6A C1A C11A O12A . . . . -80.9(3) no
    C1A C2A C3A C4A . . . . -0.3(4) no
    C21A C2A C3A C4A . . . . -177.1(2) no
    C1A C2A C21A O21A . . . . -20.9(4) no
    C1A C2A C21A O22A . . . . 160.9(3) no
    C3A C2A C21A O21A . . . . 155.9(2) no
    C3A C2A C21A O22A . . . . -22.3(4) no
    C2A C3A C4A N4A . . . . 178.8(2) no
    C2A C3A C4A C5A . . . . -0.2(4) no
    N4A C4A C5A C6A . . . . -179.2(2) no
    C3A C4A C5A C6A . . . . -0.2(4) no
    C4A C5A C6A C1A . . . . 1.0(4) 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
    O21A H21A O12A 4_545 0.90 1.58 2.480(3) 179 yes
    N4 H42 O11A 3_445 0.99 2.46 2.902(3) 107 yes
    N4 H42 O22A 3_455 0.99 1.93 2.885(3) 162 yes
    N4 H43 O11A 4_545 0.92 1.92 2.835(3) 179 yes
    N4 H44 O12A . 0.92 1.90 2.809(3) 172 yes
    C6 H6 O12A 1_545 0.93 2.46 3.205(4) 138 yes
    C41 H41 O42A 2_646 0.93 2.59 3.466(4) 158 no
data_III
_audit_creation_method     'SHELXL97 (Sheldrick, 2008)'
_chemical_name_systematic
;
4-(phenyldiazenyl)anilinium 3-carboxy-5-nitrobenzoate monohydrate
;
_chemical_name_common
               '4-(phenylazo)anilinium hydrogen 5-nitroisophthalate monohydrate'
_chemical_formula_moiety     'C12 H12 N3 + , C8 H4 N O6 - , H2 O'
_chemical_formula_sum     'C20 H18 N4 O7'
_chemical_formula_iupac     'C12 H12 N3 + , C8 H4 N O6 - , H2 O'
_chemical_formula_weight     426.38
_chemical_melting_point     393
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P b c a'
_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
    5 -x,-y,-z
    6 1/2+x,y,1/2-z
    7 1/2-x,1/2+y,z
    8 x,1/2-y,1/2+z
_cell_length_a     14.0965(15)
_cell_length_b     6.7602(7)
_cell_length_c     43.091(5)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     4106.4(8)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     3315
_cell_measurement_theta_min     2.38
_cell_measurement_theta_max     25.38
_cell_measurement_temperature     130(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     red
_exptl_crystal_size_max     0.50
_exptl_crystal_size_mid     0.15
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     1.379
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1776
_exptl_absorpt_coefficient_mu     0.107
_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     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     20144
_diffrn_reflns_av_R_equivalents     0.0964
_diffrn_reflns_av_sigmaI/netI     0.0720
_diffrn_reflns_theta_min     1.73
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     7
_diffrn_reflns_limit_l_min     -51
_diffrn_reflns_limit_l_max     42
_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     3612
_reflns_number_gt     2720
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1060
_refine_ls_R_factor_gt     0.0846
_refine_ls_wR_factor_gt     0.2040
_refine_ls_wR_factor_ref     0.2109
_refine_ls_goodness_of_fit_ref     1.222
_refine_ls_restrained_S_all     1.222
_refine_ls_number_reflns     3612
_refine_ls_number_parameters     304
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w = 1/[σ²(Fo²)+(0.0P)²+14.8749P] 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     0.365
_refine_diff_density_min     -0.279
_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     '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 N1 0.7409(3) 0.7594(6) 0.18617(9) 0.0357(14) Uani . . 1.000
    N N4 0.6279(4) 0.7422(7) 0.06108(10) 0.0363(16) Uani . . 1.000
    N N11 0.8281(3) 0.7834(6) 0.19166(10) 0.0390(16) Uani . . 1.000
    C C1 0.7194(3) 0.7529(7) 0.15412(11) 0.0303(16) Uani . . 1.000
    C C2 0.7849(3) 0.7528(6) 0.13009(11) 0.0290(14) Uani . . 1.000
    C C3 0.7550(3) 0.7490(7) 0.09974(11) 0.0297(16) Uani . . 1.000
    C C4 0.6583(3) 0.7474(7) 0.09334(11) 0.0273(16) Uani . . 1.000
    C C5 0.5918(4) 0.7462(7) 0.11685(12) 0.0363(17) Uani . . 1.000
    C C6 0.6227(3) 0.7468(8) 0.14728(11) 0.0353(17) Uani . . 1.000
    C C11 0.8511(4) 0.7887(7) 0.22392(13) 0.0430(19) Uani . . 1.000
    C C21 0.9417(5) 0.8544(9) 0.23093(15) 0.056(2) Uani . . 1.000
    C C31 0.9690(5) 0.8677(10) 0.26147(17) 0.068(3) Uani . . 1.000
    C C41 0.9082(6) 0.8142(10) 0.28480(16) 0.069(3) Uani . . 1.000
    C C51 0.8184(5) 0.7438(10) 0.27790(15) 0.065(3) Uani . . 1.000
    C C61 0.7894(4) 0.7324(8) 0.24733(13) 0.0500(19) Uani . . 1.000
    O O11A 0.4375(2) 0.8187(5) 0.06107(8) 0.0397(12) Uani . . 1.000
    O O12A 0.3634(2) 0.7778(5) 0.01579(7) 0.0301(10) Uani . . 1.000
    O O31A 0.0232(2) 0.7423(5) 0.01107(8) 0.0342(11) Uani . . 1.000
    O O32A -0.0683(2) 0.8198(6) 0.05154(9) 0.0477(14) Uani . . 1.000
    O O51A 0.0952(4) 0.9375(10) 0.15158(11) 0.094(3) Uani . . 1.000
    O O52A 0.2474(4) 0.9688(7) 0.15270(9) 0.0720(18) Uani . . 1.000
    N N5A 0.1738(4) 0.9320(8) 0.13951(11) 0.0527(19) Uani . . 1.000
    C C1A 0.2698(3) 0.8203(6) 0.06086(11) 0.0263(16) Uani . . 1.000
    C C2A 0.1865(3) 0.7948(6) 0.04427(11) 0.0260(14) Uani . . 1.000
    C C3A 0.0991(3) 0.8107(6) 0.05857(11) 0.0280(16) Uani . . 1.000
    C C4A 0.0943(4) 0.8520(7) 0.09006(11) 0.0340(17) Uani . . 1.000
    C C5A 0.1772(4) 0.8766(7) 0.10612(11) 0.0340(16) Uani . . 1.000
    C C6A 0.2661(4) 0.8620(7) 0.09240(11) 0.0310(16) Uani . . 1.000
    C C11A 0.3650(3) 0.8046(6) 0.04523(11) 0.0280(16) Uani . . 1.000
    C C31A 0.0101(4) 0.7900(7) 0.04039(12) 0.0330(17) Uani . . 1.000
    O O1W 0.7467(3) 0.9794(5) 0.02378(8) 0.0322(11) Uani . . 1.000
    H H2 0.84940 0.75530 0.13460 0.0350 Uiso calc R 1.000
    H H3 0.79890 0.74750 0.08360 0.0350 Uiso calc R 1.000
    H H5 0.52740 0.74500 0.11230 0.0440 Uiso calc R 1.000
    H H6 0.57870 0.74310 0.16330 0.0420 Uiso calc R 1.000
    H H21 0.98350 0.88910 0.21510 0.0680 Uiso calc R 1.000
    H H31 1.02940 0.91350 0.26630 0.0820 Uiso calc R 1.000
    H H41 0.92740 0.82520 0.30540 0.0830 Uiso calc R 1.000
    H H42 0.660(4) 0.821(8) 0.0501(12) 0.041(15) Uiso . . 1.000
    H H43 0.639(5) 0.622(8) 0.0530(12) 0.050(16) Uiso . . 1.000
    H H44 0.564(4) 0.766(7) 0.0596(11) 0.044(14) Uiso . . 1.000
    H H51 0.77790 0.70440 0.29380 0.0780 Uiso calc R 1.000
    H H61 0.72890 0.68730 0.24250 0.0600 Uiso calc R 1.000
    H H2A 0.18940 0.76650 0.02320 0.0310 Uiso calc R 1.000
    H H4A 0.03600 0.86270 0.10000 0.0410 Uiso calc R 1.000
    H H6A 0.32130 0.87960 0.10390 0.0380 Uiso calc R 1.000
    H H31A -0.037(5) 0.759(11) 0.0001(16) 0.08(2) Uiso . . 1.000
    H H1W 0.708(3) 1.049(7) 0.0119(11) 0.043(13) Uiso . . 1.000
    H H2W 0.782(6) 0.903(14) 0.0086(19) 0.042(3) Uiso . . 1.000
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
    O11A C11A . . 1.233(5) no
    O12A C11A . . 1.282(6) no
    O31A C31A . . 1.317(6) no
    O32A C31A . . 1.222(6) no
    O51A N5A . . 1.225(8) no
    O52A N5A . . 1.209(8) no
    O31A H31A . . 0.98(7) no
    O1W H2W . . 0.97(8) no
    O1W H1W . . 0.88(5) no
    N1 C1 . . 1.415(6) no
    N1 N11 . . 1.262(6) no
    N4 C4 . . 1.455(6) no
    N11 C11 . . 1.428(7) no
    N4 H44 . . 0.92(6) no
    N4 H43 . . 0.90(5) no
    N4 H42 . . 0.84(6) no
    N5A C5A . . 1.488(7) no
    C1 C6 . . 1.395(6) no
    C1 C2 . . 1.387(6) no
    C2 C3 . . 1.374(7) no
    C3 C4 . . 1.391(6) no
    C4 C5 . . 1.380(7) no
    C5 C6 . . 1.382(7) no
    C11 C61 . . 1.385(8) no
    C11 C21 . . 1.386(9) no
    C21 C31 . . 1.374(10) no
    C31 C41 . . 1.370(10) no
    C41 C51 . . 1.385(11) no
    C51 C61 . . 1.381(9) no
    C2 H2 . . 0.9300 no
    C3 H3 . . 0.9300 no
    C5 H5 . . 0.9300 no
    C6 H6 . . 0.9300 no
    C21 H21 . . 0.9300 no
    C31 H31 . . 0.9300 no
    C41 H41 . . 0.9300 no
    C51 H51 . . 0.9300 no
    C61 H61 . . 0.9300 no
    C1A C2A . . 1.386(6) no
    C1A C11A . . 1.505(6) no
    C1A C6A . . 1.389(7) no
    C2A C3A . . 1.382(6) no
    C3A C4A . . 1.387(7) no
    C3A C31A . . 1.486(7) no
    C4A C5A . . 1.368(8) no
    C5A C6A . . 1.389(8) no
    C2A H2A . . 0.9300 no
    C4A H4A . . 0.9300 no
    C6A H6A . . 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
    C31A O31A H31A . . . 108(4) no
    H1W O1W H2W . . . 102(6) no
    N11 N1 C1 . . . 113.3(4) no
    N1 N11 C11 . . . 114.0(4) no
    C4 N4 H44 . . . 111(3) no
    C4 N4 H42 . . . 111(4) no
    H43 N4 H44 . . . 108(5) no
    H42 N4 H44 . . . 112(5) no
    H42 N4 H43 . . . 105(5) no
    C4 N4 H43 . . . 110(4) no
    O51A N5A O52A . . . 124.8(5) no
    O51A N5A C5A . . . 116.6(5) no
    O52A N5A C5A . . . 118.6(5) no
    C2 C1 C6 . . . 119.5(4) no
    N1 C1 C6 . . . 114.6(4) no
    N1 C1 C2 . . . 125.9(4) no
    C1 C2 C3 . . . 120.4(4) no
    C2 C3 C4 . . . 119.3(4) no
    N4 C4 C5 . . . 120.1(4) no
    N4 C4 C3 . . . 118.6(4) no
    C3 C4 C5 . . . 121.3(5) no
    C4 C5 C6 . . . 118.8(5) no
    C1 C6 C5 . . . 120.6(4) no
    C21 C11 C61 . . . 120.5(5) no
    N11 C11 C21 . . . 115.4(5) no
    N11 C11 C61 . . . 124.0(5) no
    C11 C21 C31 . . . 119.2(6) no
    C21 C31 C41 . . . 120.7(7) no
    C31 C41 C51 . . . 120.4(6) no
    C41 C51 C61 . . . 119.6(6) no
    C11 C61 C51 . . . 119.6(5) no
    C3 C2 H2 . . . 120.00 no
    C1 C2 H2 . . . 120.00 no
    C2 C3 H3 . . . 120.00 no
    C4 C3 H3 . . . 120.00 no
    C6 C5 H5 . . . 121.00 no
    C4 C5 H5 . . . 121.00 no
    C5 C6 H6 . . . 120.00 no
    C1 C6 H6 . . . 120.00 no
    C11 C21 H21 . . . 120.00 no
    C31 C21 H21 . . . 121.00 no
    C21 C31 H31 . . . 120.00 no
    C41 C31 H31 . . . 120.00 no
    C31 C41 H41 . . . 120.00 no
    C51 C41 H41 . . . 120.00 no
    C61 C51 H51 . . . 120.00 no
    C41 C51 H51 . . . 120.00 no
    C51 C61 H61 . . . 120.00 no
    C11 C61 H61 . . . 120.00 no
    C6A C1A C11A . . . 119.1(4) no
    C2A C1A C6A . . . 119.9(4) no
    C2A C1A C11A . . . 121.1(4) no
    C1A C2A C3A . . . 121.1(4) no
    C2A C3A C31A . . . 120.7(4) no
    C4A C3A C31A . . . 119.6(4) no
    C2A C3A C4A . . . 119.7(4) no
    C3A C4A C5A . . . 118.5(5) no
    N5A C5A C6A . . . 117.3(5) no
    N5A C5A C4A . . . 119.5(5) no
    C4A C5A C6A . . . 123.1(5) no
    C1A C6A C5A . . . 117.7(5) no
    O12A C11A C1A . . . 115.9(4) no
    O11A C11A O12A . . . 125.0(4) no
    O11A C11A C1A . . . 119.1(4) no
    O32A C31A C3A . . . 122.8(5) no
    O31A C31A O32A . . . 123.0(5) no
    O31A C31A C3A . . . 114.2(4) no
    C3A C2A H2A . . . 119.00 no
    C1A C2A H2A . . . 120.00 no
    C3A C4A H4A . . . 121.00 no
    C5A C4A H4A . . . 121.00 no
    C1A C6A H6A . . . 121.00 no
    C5A C6A H6A . . . 121.00 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
    C1 N1 N11 C11 . . . . -179.5(4) no
    N11 N1 C1 C2 . . . . 6.0(7) no
    N11 N1 C1 C6 . . . . -173.8(4) no
    N1 N11 C11 C21 . . . . -167.4(5) no
    N1 N11 C11 C61 . . . . 13.0(7) no
    O51A N5A C5A C4A . . . . 5.6(8) no
    O51A N5A C5A C6A . . . . -177.5(5) no
    O52A N5A C5A C4A . . . . -174.1(5) no
    O52A N5A C5A C6A . . . . 2.8(7) no
    C6 C1 C2 C3 . . . . 0.7(7) no
    N1 C1 C6 C5 . . . . 178.0(5) no
    N1 C1 C2 C3 . . . . -179.1(4) no
    C2 C1 C6 C5 . . . . -1.8(7) no
    C1 C2 C3 C4 . . . . 0.7(7) no
    C2 C3 C4 C5 . . . . -1.1(7) no
    C2 C3 C4 N4 . . . . -179.6(4) no
    C3 C4 C5 C6 . . . . 0.1(7) no
    N4 C4 C5 C6 . . . . 178.6(5) no
    C4 C5 C6 C1 . . . . 1.4(8) no
    N11 C11 C21 C31 . . . . 178.8(5) no
    C61 C11 C21 C31 . . . . -1.6(9) no
    N11 C11 C61 C51 . . . . -179.7(5) no
    C21 C11 C61 C51 . . . . 0.6(8) no
    C11 C21 C31 C41 . . . . 0.9(10) no
    C21 C31 C41 C51 . . . . 0.7(11) no
    C31 C41 C51 C61 . . . . -1.6(10) no
    C41 C51 C61 C11 . . . . 1.0(9) no
    C6A C1A C2A C3A . . . . 0.2(6) no
    C11A C1A C2A C3A . . . . -179.5(4) no
    C2A C1A C6A C5A . . . . 0.0(6) no
    C11A C1A C6A C5A . . . . 179.7(4) no
    C2A C1A C11A O11A . . . . -176.5(4) no
    C2A C1A C11A O12A . . . . 3.8(6) no
    C6A C1A C11A O11A . . . . 3.8(6) no
    C6A C1A C11A O12A . . . . -175.9(4) no
    C1A C2A C3A C4A . . . . -0.3(6) no
    C1A C2A C3A C31A . . . . 177.9(4) no
    C2A C3A C4A C5A . . . . 0.2(7) no
    C31A C3A C4A C5A . . . . -178.0(4) no
    C2A C3A C31A O31A . . . . 4.7(6) no
    C2A C3A C31A O32A . . . . -173.5(4) no
    C4A C3A C31A O31A . . . . -177.2(4) no
    C4A C3A C31A O32A . . . . 4.6(7) no
    C3A C4A C5A N5A . . . . 176.6(4) no
    C3A C4A C5A C6A . . . . -0.1(7) no
    N5A C5A C6A C1A . . . . -176.8(4) no
    C4A C5A C6A C1A . . . . 0.0(7) no
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    O31A H31A O12A 3_465 0.98(7) 1.58(7) 2.536(4) 164(7) yes
    O1W H1W O12A 5_675 0.88(5) 1.95(5) 2.830(5) 173(4) yes
    O1W H2W O12A 3_565 0.97(8) 1.98(9) 2.939(5) 170(8) yes
    N4 H42 O1W . 0.84(6) 1.98(5) 2.821(6) 173(5) yes
    N4 H43 O1W 7_645 0.90(5) 2.26(6) 2.977(6) 137(5) yes
    N4 H43 O32A 7_545 0.90(5) 2.27(6) 3.005(6) 138(6) yes
    N4 H44 O11A . 0.92(6) 1.82(6) 2.733(6) 174(4) yes
    C3 H3 O32A 1_655 0.93 2.38 3.278(6) 163 yes
    C5 H5 O11A . 0.93 2.59 3.279(6) 131 yes
