##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# 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.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2011-05-23
_journal_date_accepted     2011-05-31
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue      7
_journal_page_first     o1581
_journal_page_last     o1581
_journal_paper_category     QO
_journal_coeditor_code     CV5099
_publ_contact_author_name     'Ming-Feng Wang'
_publ_contact_author_address
;
Department of Chemisry and Chemical Engineering
Jining University
273155 Qufu
Shandong
People's Republic of China
;
_publ_contact_author_email     mingfengwang_11@163.com
_publ_contact_author_fax     '+86 537 3196089'
_publ_contact_author_phone     '+86 537 3196089'
_publ_section_title
;
1,4-Dihydroquinoxaline-2,3-dione--5-nitroisophthalic acid--water (1/1/1)
;
loop_
    _publ_author_name
    _publ_author_address
    'Ming-Feng Wang'
;
Department of Chemisry and Chemical Engineering
Jining University
273155 Qufu
Shandong
People's Republic of China
;
data_I
_chemical_name_systematic
;
1,4-Dihydroquinoxaline-2,3-dione--5-nitroisophthalic acid--water (1/1/1)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C8 H6 N2 O2, C8 H5 N O6, H2 O'
_chemical_formula_sum     'C16 H13 N3 O9'
_chemical_formula_iupac     'C8 H6 N2 O2 , C8 H5 N O6 , H2 O'
_chemical_formula_weight     391.29
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     7.245(2)
_cell_length_b     8.686(3)
_cell_length_c     13.142(4)
_cell_angle_alpha     93.938(4)
_cell_angle_beta     95.619(4)
_cell_angle_gamma     95.793(4)
_cell_volume     816.3(4)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2442
_cell_measurement_theta_min     2.36
_cell_measurement_theta_max     28.18
_cell_measurement_temperature     295(2)
_exptl_crystal_description     block
_exptl_crystal_colour     orange
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.16
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.592
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     404
_exptl_absorpt_coefficient_mu     0.133
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min     0.9739
_exptl_absorpt_correction_T_max     0.9868
_exptl_special_details
;
;
_diffrn_ambient_temperature     295(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     'Bruker APEXII CCD'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     4482
_diffrn_reflns_av_R_equivalents     0.0166
_diffrn_reflns_av_sigmaI/netI     0.0259
_diffrn_reflns_theta_min     1.56
_diffrn_reflns_theta_max     25.05
_diffrn_reflns_theta_full     25.05
_diffrn_measured_fraction_theta_max     0.987
_diffrn_measured_fraction_theta_full     0.987
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     10
_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_%     ?
_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     2857
_reflns_number_gt     2441
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0390
_refine_ls_R_factor_gt     0.0333
_refine_ls_wR_factor_gt     0.0902
_refine_ls_wR_factor_ref     0.0950
_refine_ls_goodness_of_fit_ref     1.025
_refine_ls_restrained_S_all     1.025
_refine_ls_number_reflns     2857
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0491P)²+0.1990P] 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     0.175
_refine_diff_density_min     -0.193
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.040(3)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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     'APEX2 (Bruker, 2005)'
_computing_cell_refinement     'APEX2 (Bruker, 2005)'
_computing_data_reduction     'SAINT (Bruker, 2005)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N1 0.71730(16) 0.01395(14) 0.43192(9) 0.0305(3) Uani d . 1 1 . .
    H H1 0.6421 -0.0558 0.4543 0.037 Uiso calc R 1 1 . .
    N N2 0.96136(17) 0.23142(14) 0.36451(9) 0.0322(3) Uani d . 1 1 . .
    H H2 1.0403 0.2993 0.3431 0.039 Uiso calc R 1 1 . .
    N N3 0.86203(18) 0.59454(17) -0.10289(9) 0.0406(3) Uani d . 1 1 . .
    O O1 0.53849(14) 0.20004(12) 0.47998(8) 0.0398(3) Uani d . 1 1 . .
    O O2 0.79757(16) 0.42195(12) 0.42271(8) 0.0412(3) Uani d . 1 1 . .
    O O3 0.54289(17) 0.39843(12) 0.20331(9) 0.0467(3) Uani d . 1 1 . .
    O O4 0.49185(15) 0.61637(12) 0.28917(8) 0.0383(3) Uani d . 1 1 . .
    H H4A 0.4479 0.5555 0.3277 0.058 Uiso calc R 1 1 . .
    O O5 0.85764(19) 0.45403(16) -0.11072(9) 0.0569(4) Uani d . 1 1 . .
    O O6 0.9246(2) 0.67836(17) -0.16454(10) 0.0640(4) Uani d . 1 1 . .
    O O7 0.7393(2) 1.14774(14) 0.02107(10) 0.0599(4) Uani d . 1 1 . .
    O O8 0.62819(19) 1.11218(13) 0.17111(9) 0.0538(3) Uani d . 1 1 . .
    H H8 0.6236 1.2062 0.1725 0.081 Uiso calc R 1 1 . .
    O O9 0.32657(14) 0.43362(12) 0.40853(8) 0.0369(3) Uani d . 1 1 . .
    H H9A 0.4013 0.3730 0.4352 0.055 Uiso d R 1 1 . .
    H H9B 0.3007 0.4804 0.4643 0.055 Uiso d R 1 1 . .
    C C1 0.67867(19) 0.16099(17) 0.44281(10) 0.0293(3) Uani d . 1 1 . .
    C C2 0.8180(2) 0.28385(17) 0.40886(10) 0.0296(3) Uani d . 1 1 . .
    C C3 0.9929(2) 0.07624(17) 0.35027(10) 0.0299(3) Uani d . 1 1 . .
    C C4 1.1426(2) 0.0307(2) 0.30139(12) 0.0417(4) Uani d . 1 1 . .
    H H4 1.2255 0.1047 0.2770 0.050 Uiso calc R 1 1 . .
    C C5 1.1677(2) -0.1238(2) 0.28923(13) 0.0481(4) Uani d . 1 1 . .
    H H5 1.2657 -0.1545 0.2547 0.058 Uiso calc R 1 1 . .
    C C6 1.0477(2) -0.2347(2) 0.32807(12) 0.0436(4) Uani d . 1 1 . .
    H H6 1.0674 -0.3389 0.3208 0.052 Uiso calc R 1 1 . .
    C C7 0.8999(2) -0.19105(18) 0.37722(11) 0.0346(3) Uani d . 1 1 . .
    H H7 0.8201 -0.2652 0.4037 0.042 Uiso calc R 1 1 . .
    C C8 0.87052(19) -0.03525(16) 0.38704(10) 0.0280(3) Uani d . 1 1 . .
    C C9 0.63865(19) 0.64015(17) 0.13886(10) 0.0296(3) Uani d . 1 1 . .
    C C10 0.7140(2) 0.57178(18) 0.05592(10) 0.0324(3) Uani d . 1 1 . .
    H H10 0.7161 0.4648 0.0475 0.039 Uiso calc R 1 1 . .
    C C11 0.7857(2) 0.66751(18) -0.01360(10) 0.0334(3) Uani d . 1 1 . .
    C C12 0.7849(2) 0.82652(19) -0.00467(11) 0.0366(4) Uani d . 1 1 . .
    H H12 0.8342 0.8876 -0.0530 0.044 Uiso calc R 1 1 . .
    C C13 0.7085(2) 0.89318(18) 0.07831(11) 0.0334(3) Uani d . 1 1 . .
    C C14 0.6363(2) 0.79974(17) 0.14970(10) 0.0318(3) Uani d . 1 1 . .
    H H14 0.5858 0.8448 0.2054 0.038 Uiso calc R 1 1 . .
    C C15 0.5552(2) 0.53871(17) 0.21328(10) 0.0312(3) Uani d . 1 1 . .
    C C16 0.6963(2) 1.06385(19) 0.08583(12) 0.0394(4) Uani d . 1 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
    N1 C1 . 1.3360(18) ?
    N1 C8 . 1.3972(17) ?
    N1 H1 . 0.8600 ?
    N2 C2 . 1.3428(17) ?
    N2 C3 . 1.3928(19) ?
    N2 H2 . 0.8600 ?
    N3 O5 . 1.2147(19) ?
    N3 O6 . 1.2158(18) ?
    N3 C11 . 1.4764(18) ?
    O1 C1 . 1.2365(16) ?
    O2 C2 . 1.2268(18) ?
    O3 C15 . 1.2098(18) ?
    O4 C15 . 1.3114(16) ?
    O4 H4A . 0.8200 ?
    O7 C16 . 1.201(2) ?
    O8 C16 . 1.327(2) ?
    O8 H8 . 0.8200 ?
    O9 H9A . 0.8597 ?
    O9 H9B . 0.8598 ?
    C1 C2 . 1.514(2) ?
    C3 C8 . 1.390(2) ?
    C3 C4 . 1.391(2) ?
    C4 C5 . 1.373(2) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.389(3) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.376(2) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.390(2) ?
    C7 H7 . 0.9300 ?
    C9 C14 . 1.386(2) ?
    C9 C10 . 1.3900(19) ?
    C9 C15 . 1.492(2) ?
    C10 C11 . 1.381(2) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.379(2) ?
    C12 C13 . 1.388(2) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.388(2) ?
    C13 C16 . 1.491(2) ?
    C14 H14 . 0.9300 ?
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
    C1 N1 C8 . . 125.04(12) ?
    C1 N1 H1 . . 117.5 ?
    C8 N1 H1 . . 117.5 ?
    C2 N2 C3 . . 125.43(12) ?
    C2 N2 H2 . . 117.3 ?
    C3 N2 H2 . . 117.3 ?
    O5 N3 O6 . . 123.82(13) ?
    O5 N3 C11 . . 118.00(13) ?
    O6 N3 C11 . . 118.17(14) ?
    C15 O4 H4A . . 109.5 ?
    C16 O8 H8 . . 109.5 ?
    H9A O9 H9B . . 98.3 ?
    O1 C1 N1 . . 123.40(13) ?
    O1 C1 C2 . . 119.59(13) ?
    N1 C1 C2 . . 117.01(12) ?
    O2 C2 N2 . . 123.62(14) ?
    O2 C2 C1 . . 120.46(12) ?
    N2 C2 C1 . . 115.92(12) ?
    C8 C3 C4 . . 119.61(14) ?
    C8 C3 N2 . . 118.35(12) ?
    C4 C3 N2 . . 122.04(14) ?
    C5 C4 C3 . . 119.81(16) ?
    C5 C4 H4 . . 120.1 ?
    C3 C4 H4 . . 120.1 ?
    C4 C5 C6 . . 120.48(14) ?
    C4 C5 H5 . . 119.8 ?
    C6 C5 H5 . . 119.8 ?
    C7 C6 C5 . . 120.25(15) ?
    C7 C6 H6 . . 119.9 ?
    C5 C6 H6 . . 119.9 ?
    C6 C7 C8 . . 119.52(15) ?
    C6 C7 H7 . . 120.2 ?
    C8 C7 H7 . . 120.2 ?
    C3 C8 C7 . . 120.28(13) ?
    C3 C8 N1 . . 118.07(12) ?
    C7 C8 N1 . . 121.64(13) ?
    C14 C9 C10 . . 120.07(13) ?
    C14 C9 C15 . . 120.96(12) ?
    C10 C9 C15 . . 118.95(13) ?
    C11 C10 C9 . . 117.97(14) ?
    C11 C10 H10 . . 121.0 ?
    C9 C10 H10 . . 121.0 ?
    C12 C11 C10 . . 123.11(13) ?
    C12 C11 N3 . . 118.92(13) ?
    C10 C11 N3 . . 117.95(14) ?
    C11 C12 C13 . . 118.30(14) ?
    C11 C12 H12 . . 120.8 ?
    C13 C12 H12 . . 120.8 ?
    C12 C13 C14 . . 119.81(14) ?
    C12 C13 C16 . . 118.98(14) ?
    C14 C13 C16 . . 121.12(13) ?
    C9 C14 C13 . . 120.74(13) ?
    C9 C14 H14 . . 119.6 ?
    C13 C14 H14 . . 119.6 ?
    O3 C15 O4 . . 123.24(14) ?
    O3 C15 C9 . . 123.34(13) ?
    O4 C15 C9 . . 113.40(12) ?
    O7 C16 O8 . . 123.72(15) ?
    O7 C16 C13 . . 123.92(15) ?
    O8 C16 C13 . . 112.33(13) ?
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
    C8 N1 C1 O1 . . . . 177.60(13) ?
    C8 N1 C1 C2 . . . . -3.47(19) ?
    C3 N2 C2 O2 . . . . 177.86(13) ?
    C3 N2 C2 C1 . . . . -1.7(2) ?
    O1 C1 C2 O2 . . . . 3.7(2) ?
    N1 C1 C2 O2 . . . . -175.29(13) ?
    O1 C1 C2 N2 . . . . -176.70(13) ?
    N1 C1 C2 N2 . . . . 4.33(18) ?
    C2 N2 C3 C8 . . . . -1.9(2) ?
    C2 N2 C3 C4 . . . . 178.47(14) ?
    C8 C3 C4 C5 . . . . 0.4(2) ?
    N2 C3 C4 C5 . . . . 180.00(14) ?
    C3 C4 C5 C6 . . . . -1.9(3) ?
    C4 C5 C6 C7 . . . . 1.4(3) ?
    C5 C6 C7 C8 . . . . 0.5(2) ?
    C4 C3 C8 C7 . . . . 1.5(2) ?
    N2 C3 C8 C7 . . . . -178.08(12) ?
    C4 C3 C8 N1 . . . . -177.39(13) ?
    N2 C3 C8 N1 . . . . 3.02(19) ?
    C6 C7 C8 C3 . . . . -2.0(2) ?
    C6 C7 C8 N1 . . . . 176.89(13) ?
    C1 N1 C8 C3 . . . . -0.2(2) ?
    C1 N1 C8 C7 . . . . -179.10(13) ?
    C14 C9 C10 C11 . . . . 0.2(2) ?
    C15 C9 C10 C11 . . . . 178.18(12) ?
    C9 C10 C11 C12 . . . . -0.3(2) ?
    C9 C10 C11 N3 . . . . -178.69(12) ?
    O5 N3 C11 C12 . . . . -178.32(14) ?
    O6 N3 C11 C12 . . . . 1.3(2) ?
    O5 N3 C11 C10 . . . . 0.1(2) ?
    O6 N3 C11 C10 . . . . 179.69(14) ?
    C10 C11 C12 C13 . . . . 0.1(2) ?
    N3 C11 C12 C13 . . . . 178.43(13) ?
    C11 C12 C13 C14 . . . . 0.2(2) ?
    C11 C12 C13 C16 . . . . -176.43(13) ?
    C10 C9 C14 C13 . . . . 0.1(2) ?
    C15 C9 C14 C13 . . . . -177.81(12) ?
    C12 C13 C14 C9 . . . . -0.3(2) ?
    C16 C13 C14 C9 . . . . 176.26(13) ?
    C14 C9 C15 O3 . . . . 174.98(14) ?
    C10 C9 C15 O3 . . . . -2.9(2) ?
    C14 C9 C15 O4 . . . . -3.3(2) ?
    C10 C9 C15 O4 . . . . 178.79(12) ?
    C12 C13 C16 O7 . . . . 4.3(2) ?
    C14 C13 C16 O7 . . . . -172.28(16) ?
    C12 C13 C16 O8 . . . . -177.21(14) ?
    C14 C13 C16 O8 . . . . 6.2(2) ?
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
    N2 H2 O6 2_765 0.86 2.40 2.9632(18) 123.2
    N2 H2 O9 1_655 0.86 2.33 3.0071(17) 135.9
    N1 H1 O1 2_656 0.86 2.02 2.8723(17) 173.2
    O9 H9B O2 2_666 0.86 1.89 2.7456(15) 170.5
    O8 H8 O3 1_565 0.82 1.86 2.6381(17) 159.1
    O9 H9A O1 . 0.86 1.97 2.8220(15) 168.3
    O4 H4A O9 . 0.82 1.78 2.5962(15) 173.0
