##############################################################################
#                                                                            #
# 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_general
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2014-01-10
_journal_date_accepted     2014-01-10
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2014
_journal_volume     70
_journal_issue      2
_journal_page_first     o158
_journal_page_last     o159
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536814000609
_journal_coeditor_code     HG5375
_publ_contact_author_name     ' Edward RT Tiekink '
_publ_contact_author_address
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
_publ_contact_author_email
;
edward.tiekink@gmail.com
;
_publ_contact_author_fax     ' +60 3 7967 4193 '
_publ_contact_author_phone     ' +60 3 7967 4204 '
_publ_section_title
;
2-(2-Amino-4-nitrophenyl)-7-nitro-4H-3,1-benzoxazin-4-one
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Tiekink, Edward R. T.' .
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
    'Wardell, James L. '
;
Additional correspondence author, e-mail: j.wardell@abdn.ac.uk.
;
;
Fundação Oswaldo Cruz, Instituto de Tecnologia em
Fármacos--Farmanguinhos, R. Sizenando Nabuco, 100, Manguinhos 21041-250,
Rio de Janeiro,
RJ, Brazil
Chemistry Department, University of Aberdeen, Old Aberdeen AB24 3UE,
Scotland
;
data_I
_audit_creation_method     SHELXL-97
_database_code_depnum_ccdc_archive     'CCDC 980846'
_chemical_name_systematic
;
2-(2-Amino-4-nitrophenyl)-7-nitro-4H-3,1-benzoxazin-4-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H8 N4 O6'
_chemical_formula_sum     'C14 H8 N4 O6'
_chemical_formula_iupac     'C14 H8 N4 O6'
_chemical_formula_weight     328.24
_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     7.0229(3)
_cell_length_b     8.6148(3)
_cell_length_c     21.5662(15)
_cell_angle_alpha     90.00
_cell_angle_beta     90.029(6)
_cell_angle_gamma     90.00
_cell_volume     1304.77(12)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     14670
_cell_measurement_theta_min     3.0
_cell_measurement_theta_max     27.5
_cell_measurement_temperature     100(2)
_exptl_crystal_description     'plate'
_exptl_crystal_colour     'yellow'
_exptl_crystal_size_max     0.13
_exptl_crystal_size_mid     0.08
_exptl_crystal_size_min     0.03
_exptl_crystal_density_diffrn     1.671
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     672
_exptl_absorpt_coefficient_mu     0.135
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
                                 '(CrystalClear-SM Expert; Rigaku, 2012)'
_exptl_absorpt_correction_T_min     0.831
_exptl_absorpt_correction_T_max     1.000
_exptl_special_details
;
;
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     'Graphite'
_diffrn_measurement_device_type
;
Rigaku R-AXIS conversion
;
_diffrn_measurement_device
;
Crystal Goniometer
;
_diffrn_measurement_method     'profile data from ω-scans'
_diffrn_detector_area_resol_mean     10.0000
_diffrn_reflns_number     16840
_diffrn_reflns_av_R_equivalents     0.0257
_diffrn_reflns_av_sigmaI/netI     0.0181
_diffrn_reflns_theta_min     3.03
_diffrn_reflns_theta_max     27.48
_diffrn_reflns_theta_full     27.48
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -28
_diffrn_reflns_limit_l_max     28
_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 >
2σ(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     2983
_reflns_number_gt     2513
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0396
_refine_ls_R_factor_gt     0.0339
_refine_ls_wR_factor_gt     0.0984
_refine_ls_wR_factor_ref     0.1011
_refine_ls_goodness_of_fit_ref     1.121
_refine_ls_restrained_S_all     1.120
_refine_ls_number_reflns     2983
_refine_ls_number_parameters     223
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0557P)²+0.2657P] 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     0.378
_refine_diff_density_min     -0.206
_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     'CrystalClear-SM Expert (Rigaku, 2012)'
_computing_cell_refinement     'CrystalClear-SM Expert (Rigaku, 2012)'
_computing_data_reduction     'CrystalClear-SM Expert (Rigaku, 2012)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
          'ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material     'publCIF (Westrip, 2010)'
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
    O O1 0.31373(16) 0.12873(11) -0.24884(4) 0.0331(3) Uani d . 1 1 . .
    O O2 0.46051(15) -0.04287(11) -0.19338(5) 0.0346(3) Uani d . 1 1 . .
    O O3 0.31958(12) 0.37682(9) 0.06796(4) 0.01839(19) Uani d . 1 1 . .
    O O4 0.33686(15) 0.36166(10) 0.17002(4) 0.0293(2) Uani d . 1 1 . .
    O O5 0.01987(14) 1.12855(10) 0.07508(4) 0.0255(2) Uani d . 1 1 . .
    O O6 -0.00939(15) 1.12189(10) 0.17491(4) 0.0305(2) Uani d . 1 1 . .
    N N1 0.37678(15) 0.08006(12) -0.19950(5) 0.0217(2) Uani d . 1 1 . .
    N N2 0.19120(16) 0.56949(12) -0.11084(5) 0.0200(2) Uani d D 1 1 . .
    H H1N 0.175(2) 0.6344(14) -0.0794(5) 0.024 Uiso d D 1 1 . .
    H H2N 0.176(2) 0.5998(16) -0.1498(5) 0.024 Uiso d D 1 1 . .
    N N3 0.21171(14) 0.59740(11) 0.01426(4) 0.0160(2) Uani d . 1 1 . .
    N N4 0.03554(15) 1.06317(12) 0.12548(4) 0.0193(2) Uani d . 1 1 . .
    C C1 0.34836(16) 0.17765(13) -0.14391(5) 0.0174(2) Uani d . 1 1 . .
    C C2 0.28728(16) 0.32695(13) -0.15271(5) 0.0169(2) Uani d . 1 1 . .
    H H2 0.2653 0.3648 -0.1935 0.020 Uiso calc R 1 1 . .
    C C3 0.25693(16) 0.42466(13) -0.10088(5) 0.0154(2) Uani d . 1 1 . .
    C C4 0.29441(16) 0.36214(13) -0.04081(5) 0.0156(2) Uani d . 1 1 . .
    C C5 0.35508(16) 0.20706(13) -0.03512(5) 0.0182(2) Uani d . 1 1 . .
    H H5 0.3774 0.1660 0.0051 0.022 Uiso calc R 1 1 . .
    C C6 0.38315(16) 0.11279(13) -0.08591(5) 0.0185(2) Uani d . 1 1 . .
    H H6 0.4243 0.0083 -0.0815 0.022 Uiso calc R 1 1 . .
    C C7 0.27046(16) 0.45587(13) 0.01513(5) 0.0155(2) Uani d . 1 1 . .
    C C8 0.29892(17) 0.44138(14) 0.12669(5) 0.0192(2) Uani d . 1 1 . .
    C C9 0.23325(16) 0.60264(13) 0.12738(5) 0.0165(2) Uani d . 1 1 . .
    C C10 0.19409(16) 0.67456(13) 0.07059(5) 0.0154(2) Uani d . 1 1 . .
    C C11 0.13195(16) 0.82896(13) 0.06998(5) 0.0162(2) Uani d . 1 1 . .
    H H11 0.1066 0.8811 0.0321 0.019 Uiso calc R 1 1 . .
    C C12 0.10881(16) 0.90273(13) 0.12612(5) 0.0163(2) Uani d . 1 1 . .
    C C13 0.14479(17) 0.83313(14) 0.18319(5) 0.0181(2) Uani d . 1 1 . .
    H H13 0.1260 0.8882 0.2208 0.022 Uiso calc R 1 1 . .
    C C14 0.20854(17) 0.68167(14) 0.18338(5) 0.0186(2) Uani d . 1 1 . .
    H H14 0.2356 0.6312 0.2215 0.022 Uiso calc R 1 1 . .
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell s.u.'s are taken into
account individually in the estimation of s.u.'s in distances, angles and
torsion angles; correlations between s.u.'s in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'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 N1 . 1.2263(14) ?
    O2 N1 . 1.2185(14) ?
    O3 C7 . 1.3712(13) ?
    O3 C8 . 1.3910(13) ?
    O4 C8 . 1.1897(14) ?
    O5 N4 . 1.2291(13) ?
    O6 N4 . 1.2215(13) ?
    N1 C1 . 1.4780(14) ?
    N2 C3 . 1.3476(15) ?
    N2 H1N . 0.886(9) ?
    N2 H2N . 0.886(9) ?
    N3 C7 . 1.2873(15) ?
    N3 C10 . 1.3904(14) ?
    N4 C12 . 1.4749(15) ?
    C1 C2 . 1.3690(16) ?
    C1 C6 . 1.3913(16) ?
    C2 C3 . 1.4156(15) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.4273(15) ?
    C4 C5 . 1.4076(16) ?
    C4 C7 . 1.4615(15) ?
    C5 C6 . 1.3779(16) ?
    C5 H5 . 0.9500 ?
    C6 H6 . 0.9500 ?
    C8 C9 . 1.4639(16) ?
    C9 C14 . 1.3972(15) ?
    C9 C10 . 1.3997(15) ?
    C10 C11 . 1.3999(16) ?
    C11 C12 . 1.3771(15) ?
    C11 H11 . 0.9500 ?
    C12 C13 . 1.3921(16) ?
    C13 C14 . 1.3795(17) ?
    C13 H13 . 0.9500 ?
    C14 H14 . 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
    C7 O3 C8 . . 122.12(9) ?
    O2 N1 O1 . . 124.42(10) ?
    O2 N1 C1 . . 118.16(10) ?
    O1 N1 C1 . . 117.42(10) ?
    C3 N2 H1N . . 120.5(10) ?
    C3 N2 H2N . . 117.6(10) ?
    H1N N2 H2N . . 121.6(14) ?
    C7 N3 C10 . . 117.96(9) ?
    O6 N4 O5 . . 123.98(10) ?
    O6 N4 C12 . . 118.05(9) ?
    O5 N4 C12 . . 117.95(9) ?
    C2 C1 C6 . . 123.84(10) ?
    C2 C1 N1 . . 117.67(10) ?
    C6 C1 N1 . . 118.49(10) ?
    C1 C2 C3 . . 119.76(10) ?
    C1 C2 H2 . . 120.1 ?
    C3 C2 H2 . . 120.1 ?
    N2 C3 C2 . . 118.45(10) ?
    N2 C3 C4 . . 123.86(10) ?
    C2 C3 C4 . . 117.68(10) ?
    C5 C4 C3 . . 119.54(10) ?
    C5 C4 C7 . . 119.16(10) ?
    C3 C4 C7 . . 121.30(10) ?
    C6 C5 C4 . . 122.24(10) ?
    C6 C5 H5 . . 118.9 ?
    C4 C5 H5 . . 118.9 ?
    C5 C6 C1 . . 116.93(10) ?
    C5 C6 H6 . . 121.5 ?
    C1 C6 H6 . . 121.5 ?
    N3 C7 O3 . . 124.26(10) ?
    N3 C7 C4 . . 123.25(10) ?
    O3 C7 C4 . . 112.49(9) ?
    O4 C8 O3 . . 117.45(11) ?
    O4 C8 C9 . . 127.60(11) ?
    O3 C8 C9 . . 114.95(9) ?
    C14 C9 C10 . . 121.07(10) ?
    C14 C9 C8 . . 120.70(10) ?
    C10 C9 C8 . . 118.22(10) ?
    N3 C10 C9 . . 122.37(10) ?
    N3 C10 C11 . . 118.28(10) ?
    C9 C10 C11 . . 119.34(10) ?
    C12 C11 C10 . . 117.84(10) ?
    C12 C11 H11 . . 121.1 ?
    C10 C11 H11 . . 121.1 ?
    C11 C12 C13 . . 123.86(11) ?
    C11 C12 N4 . . 117.75(10) ?
    C13 C12 N4 . . 118.36(10) ?
    C14 C13 C12 . . 117.96(10) ?
    C14 C13 H13 . . 121.0 ?
    C12 C13 H13 . . 121.0 ?
    C13 C14 C9 . . 119.92(10) ?
    C13 C14 H14 . . 120.0 ?
    C9 C14 H14 . . 120.0 ?
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
    O2 N1 C1 C2 . . . . 167.94(11) ?
    O1 N1 C1 C2 . . . . -12.17(16) ?
    O2 N1 C1 C6 . . . . -12.66(16) ?
    O1 N1 C1 C6 . . . . 167.23(11) ?
    C6 C1 C2 C3 . . . . 0.27(18) ?
    N1 C1 C2 C3 . . . . 179.63(10) ?
    C1 C2 C3 N2 . . . . -177.99(11) ?
    C1 C2 C3 C4 . . . . 0.75(16) ?
    N2 C3 C4 C5 . . . . 177.25(11) ?
    C2 C3 C4 C5 . . . . -1.41(16) ?
    N2 C3 C4 C7 . . . . -2.54(18) ?
    C2 C3 C4 C7 . . . . 178.79(10) ?
    C3 C4 C5 C6 . . . . 1.12(17) ?
    C7 C4 C5 C6 . . . . -179.08(11) ?
    C4 C5 C6 C1 . . . . -0.12(17) ?
    C2 C1 C6 C5 . . . . -0.60(18) ?
    N1 C1 C6 C5 . . . . -179.96(10) ?
    C10 N3 C7 O3 . . . . -1.02(16) ?
    C10 N3 C7 C4 . . . . 179.81(10) ?
    C8 O3 C7 N3 . . . . 3.96(17) ?
    C8 O3 C7 C4 . . . . -176.79(9) ?
    C5 C4 C7 N3 . . . . -178.47(11) ?
    C3 C4 C7 N3 . . . . 1.33(18) ?
    C5 C4 C7 O3 . . . . 2.27(15) ?
    C3 C4 C7 O3 . . . . -177.93(10) ?
    C7 O3 C8 O4 . . . . 176.57(11) ?
    C7 O3 C8 C9 . . . . -3.88(15) ?
    O4 C8 C9 C14 . . . . 0.2(2) ?
    O3 C8 C9 C14 . . . . -179.33(10) ?
    O4 C8 C9 C10 . . . . -179.16(13) ?
    O3 C8 C9 C10 . . . . 1.35(15) ?
    C7 N3 C10 C9 . . . . -1.60(16) ?
    C7 N3 C10 C11 . . . . 179.43(10) ?
    C14 C9 C10 N3 . . . . -177.98(10) ?
    C8 C9 C10 N3 . . . . 1.34(17) ?
    C14 C9 C10 C11 . . . . 0.98(17) ?
    C8 C9 C10 C11 . . . . -179.70(10) ?
    N3 C10 C11 C12 . . . . 177.86(10) ?
    C9 C10 C11 C12 . . . . -1.14(16) ?
    C10 C11 C12 C13 . . . . 0.46(18) ?
    C10 C11 C12 N4 . . . . -177.45(10) ?
    O6 N4 C12 C11 . . . . 170.38(11) ?
    O5 N4 C12 C11 . . . . -8.20(15) ?
    O6 N4 C12 C13 . . . . -7.64(16) ?
    O5 N4 C12 C13 . . . . 173.77(11) ?
    C11 C12 C13 C14 . . . . 0.44(18) ?
    N4 C12 C13 C14 . . . . 178.34(10) ?
    C12 C13 C14 C9 . . . . -0.62(17) ?
    C10 C9 C14 C13 . . . . -0.07(18) ?
    C8 C9 C14 C13 . . . . -179.38(11) ?
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 H1N N3 . 0.886(11) 2.061(11) 2.7124(14) 129.5(10)
    N2 H2N O1 2_554 0.886(11) 2.201(11) 3.0691(14) 166.1(12)
    C11 H11 O5 3_575 0.95 2.48 3.3248(14) 149
    C13 H13 O4 2_555 0.95 2.38 3.1778(14) 141
