##############################################################################
#                                                                            #
# 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     2014-02-09
_journal_date_accepted     2014-02-10
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2014
_journal_volume     70
_journal_issue      3
_journal_page_first     o293
_journal_page_last     o293
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536814002955
_journal_coeditor_code     HG5382
_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 6775 '
_publ_section_title
;
4-Nitrophthalamide
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Chin Yee Jan' .
;
Faculty of Science, Universiti Brunei Darussalam, Jalan Tungku Link BE 1410,
Negara Brunei Darussalam
;
    'Norzianah Binti Haji Shamsudin' .
;
Faculty of Science, Universiti Brunei Darussalam, Jalan Tungku Link BE 1410,
Negara Brunei Darussalam
;
    'Ai Ling Tan' .
;
Faculty of Science, Universiti Brunei Darussalam, Jalan Tungku Link BE 1410,
Negara Brunei Darussalam
;
    'David J. Young'
;
Additional correspondence author, e-mail: david.young@ubd.edu.bn.
;
;
Faculty of Science, Universiti Brunei Darussalam, Jalan Tungku Link BE 1410,
Negara Brunei Darussalam
;
    'Ng, Seik Weng' .
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
Chemistry Department, Faculty of Science, King Abdulaziz University,
PO Box 80203 Jeddah, Saudi Arabia
;
    'Tiekink, Edward R. T.' .
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
_publ_section_synopsis     .
data_I
_audit_creation_method     SHELXL-97
_database_code_depnum_ccdc_archive     'CCDC 985960'
_chemical_name_systematic
;
4-Nitrobenzene-1,2-dicarboxamide
;
_chemical_name_common
;
4-Nitrophthalamide
;
_chemical_formula_moiety     'C8 H7 N3 O4'
_chemical_formula_sum     'C8 H7 N3 O4'
_chemical_formula_iupac     'C8 H7 N3 O4'
_chemical_formula_weight     209.17
_chemical_melting_point     ?
_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     7.7425(2)
_cell_length_b     9.6634(2)
_cell_length_c     12.1276(3)
_cell_angle_alpha     90.00
_cell_angle_beta     106.008(3)
_cell_angle_gamma     90.00
_cell_volume     872.19(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4480
_cell_measurement_theta_min     3.7887
_cell_measurement_theta_max     76.1721
_cell_measurement_temperature     100(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.40
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.593
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     432
_exptl_absorpt_coefficient_mu     1.128
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(CrysAlis PRO; Agilent, 2013)'
_exptl_absorpt_correction_T_min     0.66771
_exptl_absorpt_correction_T_max     1.00000
_exptl_special_details
;
;
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_source     'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator     Mirror
_diffrn_measurement_device_type
                  'Agilent SuperNova Dual diffractometer with an Atlas detector'
_diffrn_measurement_method     '\w scan'
_diffrn_detector_area_resol_mean     10.4041
_diffrn_reflns_number     7908
_diffrn_reflns_av_R_equivalents     0.0286
_diffrn_reflns_av_sigmaI/netI     0.0178
_diffrn_reflns_theta_min     5.95
_diffrn_reflns_theta_max     76.37
_diffrn_reflns_theta_full     76.37
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details
;
Refinement of <i>F</i>^2^ against ALL reflections. The weighted <i>R</i>-factor
<i>wR</i> and goodness of fit <i>S</i> are based on <i>F</i>^2^, conventional
<i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for
negative <i>F</i>^2^. The threshold expression of <i>F</i>^2^ >
\s(<i>F</i>^2^) is used only for calculating <i>R</i>-factors(gt) <i>etc</i>.
and is not relevant to the choice of reflections for refinement.
<i>R</i>-factors based on <i>F</i>^2^ are statistically about twice as large
as those based on <i>F</i>, and <i>R</i>- factors based on ALL data will be
even larger.
;
_reflns_number_total     1821
_reflns_number_gt     1748
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0332
_refine_ls_R_factor_gt     0.0320
_refine_ls_wR_factor_gt     0.0886
_refine_ls_wR_factor_ref     0.0901
_refine_ls_goodness_of_fit_ref     1.034
_refine_ls_restrained_S_all     1.034
_refine_ls_number_reflns     1821
_refine_ls_number_parameters     164
_refine_ls_number_restraints     4
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[\s^2^(Fo^2^)+(0.0552P)^2^+0.2944P] where P=(Fo^2^+2Fc^2^)/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     0.325
_refine_diff_density_min     -0.245
_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' 0.0181 0.0091
                         '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' 0.0311 0.0180
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0492 0.0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CrysAlis PRO (Agilent, 2013)'
_computing_cell_refinement     'CrysAlis PRO (Agilent, 2013)'
_computing_data_reduction     'CrysAlis PRO (Agilent, 2013)'
_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 0.61481(11) 0.80745(8) 0.55898(7) 0.0202(2) Uani d . 1 1 . .
    O O2 0.54207(13) 0.79742(9) 0.37347(8) 0.0266(2) Uani d . 1 1 . .
    O O3 1.04596(10) 0.17952(8) 0.51619(7) 0.0160(2) Uani d . 1 1 . .
    O O4 0.91323(12) 0.23508(8) 0.72189(7) 0.0192(2) Uani d . 1 1 . .
    N N1 0.60572(12) 0.74606(10) 0.46837(8) 0.0177(2) Uani d . 1 1 . .
    N N2 0.76591(13) 0.09066(10) 0.45344(8) 0.0171(2) Uani d D 1 1 . .
    H H21 0.6511(13) 0.1037(17) 0.4443(14) 0.025(4) Uiso d D 1 1 . .
    H H22 0.809(2) 0.0070(11) 0.4535(14) 0.025(4) Uiso d D 1 1 . .
    N N3 1.04060(14) 0.44255(10) 0.77908(8) 0.0182(2) Uani d D 1 1 . .
    H H31 1.096(2) 0.4063(17) 0.8462(10) 0.027(4) Uiso d D 1 1 . .
    H H32 1.050(2) 0.5306(10) 0.7667(13) 0.025(4) Uiso d D 1 1 . .
    C C1 0.67444(14) 0.60364(11) 0.47498(10) 0.0154(2) Uani d . 1 1 . .
    C C2 0.63660(14) 0.52513(12) 0.37619(10) 0.0171(2) Uani d . 1 1 . .
    H H2 0.566(2) 0.5640(18) 0.3011(14) 0.030(4) Uiso d . 1 1 . .
    C C3 0.70007(15) 0.38986(12) 0.38425(10) 0.0164(2) Uani d . 1 1 . .
    H H3 0.677(2) 0.3367(15) 0.3164(13) 0.018(3) Uiso d . 1 1 . .
    C C4 0.80132(14) 0.33683(11) 0.48911(9) 0.0141(2) Uani d . 1 1 . .
    C C5 0.83839(14) 0.41940(11) 0.58825(9) 0.0137(2) Uani d . 1 1 . .
    C C6 0.77318(15) 0.55445(11) 0.58101(10) 0.0150(2) Uani d . 1 1 . .
    H H6 0.795(2) 0.6102(16) 0.6473(13) 0.019(3) Uiso d . 1 1 . .
    C C7 0.88135(15) 0.19421(11) 0.49017(9) 0.0137(2) Uani d . 1 1 . .
    C C8 0.93594(14) 0.35831(11) 0.70270(9) 0.0146(2) Uani d . 1 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    O1 0.0180(4) 0.0139(4) 0.0287(5) 0.0015(3) 0.0063(3) -0.0027(3)
    O2 0.0284(5) 0.0171(4) 0.0269(5) 0.0051(3) -0.0047(4) 0.0061(3)
    O3 0.0152(4) 0.0130(4) 0.0202(4) 0.0004(3) 0.0053(3) -0.0006(3)
    O4 0.0283(4) 0.0105(4) 0.0193(4) 0.0000(3) 0.0076(3) 0.0020(3)
    N1 0.0128(4) 0.0128(5) 0.0258(5) -0.0002(3) 0.0024(4) 0.0013(4)
    N2 0.0153(5) 0.0111(5) 0.0246(5) 0.0009(4) 0.0049(4) -0.0017(4)
    N3 0.0265(5) 0.0115(5) 0.0147(5) -0.0005(4) 0.0021(4) 0.0017(3)
    C1 0.0135(5) 0.0105(5) 0.0221(6) 0.0003(4) 0.0050(4) 0.0024(4)
    C2 0.0148(5) 0.0169(5) 0.0187(5) 0.0003(4) 0.0032(4) 0.0029(4)
    C3 0.0170(5) 0.0149(5) 0.0170(5) -0.0009(4) 0.0045(4) -0.0012(4)
    C4 0.0136(5) 0.0109(5) 0.0185(5) -0.0012(4) 0.0057(4) 0.0003(4)
    C5 0.0138(5) 0.0113(5) 0.0167(5) -0.0008(4) 0.0053(4) 0.0012(4)
    C6 0.0157(5) 0.0118(5) 0.0180(5) -0.0017(4) 0.0058(4) -0.0011(4)
    C7 0.0177(5) 0.0118(5) 0.0124(5) 0.0002(4) 0.0055(4) -0.0002(4)
    C8 0.0177(5) 0.0112(5) 0.0161(5) 0.0018(4) 0.0069(4) -0.0002(4)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 N1 . 1.2336(13) ?
    O2 N1 . 1.2252(13) ?
    O3 C7 . 1.2338(14) ?
    O4 C8 . 1.2351(14) ?
    N1 C1 . 1.4698(14) ?
    N2 C7 . 1.3338(14) ?
    N2 H21 . 0.874(9) ?
    N2 H22 . 0.875(9) ?
    N3 C8 . 1.3280(15) ?
    N3 H31 . 0.881(9) ?
    N3 H32 . 0.870(9) ?
    C1 C2 . 1.3796(16) ?
    C1 C6 . 1.3862(15) ?
    C2 C3 . 1.3904(16) ?
    C2 H2 . 0.997(16) ?
    C3 C4 . 1.3945(15) ?
    C3 H3 . 0.945(15) ?
    C4 C5 . 1.4050(15) ?
    C4 C7 . 1.5097(14) ?
    C5 C6 . 1.3934(15) ?
    C5 C8 . 1.5058(14) ?
    C6 H6 . 0.943(16) ?
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
    O2 N1 O1 . . 123.47(10) ?
    O2 N1 C1 . . 118.45(10) ?
    O1 N1 C1 . . 118.09(9) ?
    C7 N2 H21 . . 119.9(11) ?
    C7 N2 H22 . . 118.1(11) ?
    H21 N2 H22 . . 120.6(15) ?
    C8 N3 H31 . . 116.6(11) ?
    C8 N3 H32 . . 122.9(10) ?
    H31 N3 H32 . . 120.4(15) ?
    C2 C1 C6 . . 123.21(10) ?
    C2 C1 N1 . . 118.72(10) ?
    C6 C1 N1 . . 118.06(10) ?
    C1 C2 C3 . . 118.01(10) ?
    C1 C2 H2 . . 121.2(10) ?
    C3 C2 H2 . . 120.8(10) ?
    C2 C3 C4 . . 120.57(10) ?
    C2 C3 H3 . . 118.2(9) ?
    C4 C3 H3 . . 121.1(9) ?
    C3 C4 C5 . . 120.16(10) ?
    C3 C4 C7 . . 118.00(9) ?
    C5 C4 C7 . . 121.64(9) ?
    C6 C5 C4 . . 119.54(10) ?
    C6 C5 C8 . . 120.41(10) ?
    C4 C5 C8 . . 119.89(9) ?
    C1 C6 C5 . . 118.50(10) ?
    C1 C6 H6 . . 121.1(9) ?
    C5 C6 H6 . . 120.4(9) ?
    O3 C7 N2 . . 123.29(10) ?
    O3 C7 C4 . . 119.99(9) ?
    N2 C7 C4 . . 116.51(9) ?
    O4 C8 N3 . . 123.42(10) ?
    O4 C8 C5 . . 119.37(10) ?
    N3 C8 C5 . . 117.20(9) ?
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 . . . . -11.31(15) ?
    O1 N1 C1 C2 . . . . 168.48(10) ?
    O2 N1 C1 C6 . . . . 169.25(10) ?
    O1 N1 C1 C6 . . . . -10.96(15) ?
    C6 C1 C2 C3 . . . . 0.44(17) ?
    N1 C1 C2 C3 . . . . -178.96(10) ?
    C1 C2 C3 C4 . . . . -1.02(16) ?
    C2 C3 C4 C5 . . . . 0.79(16) ?
    C2 C3 C4 C7 . . . . -174.21(10) ?
    C3 C4 C5 C6 . . . . 0.05(16) ?
    C7 C4 C5 C6 . . . . 174.86(9) ?
    C3 C4 C5 C8 . . . . 175.47(10) ?
    C7 C4 C5 C8 . . . . -9.71(15) ?
    C2 C1 C6 C5 . . . . 0.37(17) ?
    N1 C1 C6 C5 . . . . 179.78(9) ?
    C4 C5 C6 C1 . . . . -0.61(16) ?
    C8 C5 C6 C1 . . . . -176.01(10) ?
    C3 C4 C7 O3 . . . . 114.92(12) ?
    C5 C4 C7 O3 . . . . -60.00(14) ?
    C3 C4 C7 N2 . . . . -60.02(13) ?
    C5 C4 C7 N2 . . . . 125.05(11) ?
    C6 C5 C8 O4 . . . . 142.80(11) ?
    C4 C5 C8 O4 . . . . -32.58(15) ?
    C6 C5 C8 N3 . . . . -35.96(14) ?
    C4 C5 C8 N3 . . . . 148.66(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 H21 O1 3_666 0.874(9) 2.221(10) 3.0718(13) 164.4(15)
    N2 H22 O3 3_756 0.875(9) 2.101(10) 2.9628(12) 168.1(15)
    N3 H31 O1 2_746 0.881(9) 2.415(13) 3.1288(13) 138.4(14)
    N3 H31 O3 4_566 0.881(9) 2.351(13) 3.0979(12) 142.6(14)
    N3 H32 O4 2_756 0.870(9) 1.996(10) 2.8498(13) 166.6(15)