#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/05/2230593.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2230593
loop_
_publ_author_name
'Wang, Ming-Feng'
_publ_section_title
;
 1,4-Dihydroquinoxaline-2,3-dione--5-nitroisophthalic acid--water
 (1/1/1)
;
_journal_coeditor_code           CV5099
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1581
_journal_paper_doi               10.1107/S1600536811020873
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C8 H6 N2 O2 , C8 H5 N O6 , H2 O'
_chemical_formula_moiety         'C8 H6 N2 O2, C8 H5 N O6, H2 O'
_chemical_formula_sum            'C16 H13 N3 O9'
_chemical_formula_weight         391.29
_chemical_name_systematic
;
1,4-Dihydroquinoxaline-2,3-dione--5-nitroisophthalic acid--water (1/1/1)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                93.938(4)
_cell_angle_beta                 95.619(4)
_cell_angle_gamma                95.793(4)
_cell_formula_units_Z            2
_cell_length_a                   7.245(2)
_cell_length_b                   8.686(3)
_cell_length_c                   13.142(4)
_cell_measurement_reflns_used    2442
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.18
_cell_measurement_theta_min      2.36
_cell_volume                     816.3(4)
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4482
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.56
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.9868
_exptl_absorpt_correction_T_min  0.9739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.193
_refine_ls_extinction_coef       0.040(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         2857
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0333
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0491P)²+0.1990P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0950
_reflns_number_gt                2441
_reflns_number_total             2857
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv5099.cif
_cod_data_source_block           I
_cod_database_code               2230593
_cod_database_fobs_code          2230593
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 . .
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'
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_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_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
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) ?
