##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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 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. The current version number is 2.4.    #
#                                                                            #
# 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                                                              #
#                                                                            #
# 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     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2008-07-09
_journal_date_accepted     2008-07-11
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      8
_journal_page_first     o1523
_journal_page_last     o1524
_journal_paper_category     QO
_journal_coeditor_code     AT2591
_publ_contact_author_name     'Prof. Fun Hoong Kun'
_publ_contact_author_address
;
      X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      MALAYSIA
;
_publ_contact_author_email     hkfun@usm.my
_publ_contact_author_fax     '6 04 6579150'
_publ_contact_author_phone     '6 04 6533652'
_publ_section_title
;
5-Hydroxy-8-nitro-1,4-naphthoquinone
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Daniel Teoh-Chuan Tan' ?
;     School of Chemical Sciences
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'Hasnah Osman'
;
      Additional correspondence author, e-mail: ohasnah@usm.my.
;
;     School of Chemical Sciences
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'Azlina Harun Kamaruddin' ?
;     School of Chemical Engineering,
      Universiti Sains Malaysia,
      Seri Ampangan,
      14300 Nibong Tebal, Penang,
      Malaysia
;
    'Reza Kia' ?
;     X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'Hoong-Kun Fun' ?
;     X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
5-Hydroxy-8-nitro-1,4-naphthoquinone
;
_chemical_name_common
;
;
_chemical_formula_moiety     'C10 H5 N O5'
_chemical_formula_sum     'C10 H5 N O5'
_chemical_formula_iupac     'C10 H5 N O5'
_chemical_formula_weight     219.15
_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     8.6809(2)
_cell_length_b     8.4250(2)
_cell_length_c     12.1845(3)
_cell_angle_alpha     90.00
_cell_angle_beta     93.9460(10)
_cell_angle_gamma     90.00
_cell_volume     889.02(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5257
_cell_measurement_theta_min     2.79
_cell_measurement_theta_max     31.81
_cell_measurement_temperature     100.00(10)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'brown'
_exptl_crystal_size_max     0.35
_exptl_crystal_size_mid     0.14
_exptl_crystal_size_min     0.13
_exptl_crystal_density_diffrn     1.637
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     448
_exptl_absorpt_coefficient_mu     0.135
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min     0.9005
_exptl_absorpt_correction_T_max     0.9824
_exptl_special_details
;
The low-temperature data was collected with the Oxford Cyrosystem Cobra
low-temperature attachment.
;
_diffrn_ambient_temperature     100.00(10)
_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 SMART APEXII CCD area-detector
;
_diffrn_measurement_method     '\f and \w'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     22792
_diffrn_reflns_av_R_equivalents     0.0407
_diffrn_reflns_av_sigmaI/netI     0.0241
_diffrn_reflns_theta_min     2.79
_diffrn_reflns_theta_max     31.81
_diffrn_reflns_theta_full     31.81
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     17
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_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     3028
_reflns_number_gt     2493
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0488
_refine_ls_R_factor_gt     0.0405
_refine_ls_wR_factor_gt     0.1143
_refine_ls_wR_factor_ref     0.1193
_refine_ls_goodness_of_fit_ref     1.109
_refine_ls_restrained_S_all     1.109
_refine_ls_number_reflns     3028
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[\s^2^(Fo^2^)+(0.0671P)^2^+0.1177P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.498
_refine_diff_density_min     -0.225
_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     '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) and 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_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.60929(9) 0.14448(9) 0.47684(6) 0.01684(17) Uani d . 1 . .
    O O2 0.70729(9) 0.29533(9) 0.65117(6) 0.01718(17) Uani d . 1 . .
    O O3 1.13635(9) -0.14728(9) 0.74975(6) 0.01826(17) Uani d . 1 . .
    O O4 0.97394(10) -0.42986(9) 0.67891(6) 0.02146(19) Uani d . 1 . .
    O O5 1.11804(9) -0.37894(9) 0.54429(6) 0.01912(18) Uani d . 1 . .
    N N1 1.01058(10) -0.34927(10) 0.60140(7) 0.01427(18) Uani d . 1 . .
    C C1 0.71200(11) 0.03181(12) 0.50785(8) 0.01280(18) Uani d . 1 . .
    C C2 0.71889(11) -0.10405(12) 0.44177(8) 0.01457(19) Uani d . 1 . .
    C C3 0.81830(11) -0.22605(12) 0.47321(8) 0.01431(19) Uani d . 1 . .
    C C4 0.91370(11) -0.21081(11) 0.56968(8) 0.01219(18) Uani d . 1 . .
    C C5 0.91680(11) -0.07504(11) 0.63367(7) 0.01156(18) Uani d . 1 . .
    C C6 1.03288(11) -0.05166(12) 0.72840(8) 0.01326(19) Uani d . 1 . .
    C C7 1.02414(12) 0.09636(13) 0.79222(8) 0.0172(2) Uani d . 1 . .
    C C8 0.91880(12) 0.20847(12) 0.76649(8) 0.0168(2) Uani d . 1 . .
    C C9 0.80517(11) 0.19086(12) 0.67159(8) 0.01387(19) Uani d . 1 . .
    C C10 0.81225(11) 0.04769(11) 0.60319(8) 0.01189(18) Uani d . 1 . .
    H H8 0.9139(16) 0.3051(18) 0.8063(12) 0.022(4) Uiso d . 1 . .
    H H2 0.6513(17) -0.1106(19) 0.3752(12) 0.025(4) Uiso d . 1 . .
    H H3 0.8222(16) -0.3231(18) 0.4307(12) 0.020(3) Uiso d . 1 . .
    H H7 1.1034(18) 0.1097(19) 0.8530(13) 0.029(4) Uiso d . 1 . .
    H H1O1 0.620(2) 0.223(2) 0.5255(16) 0.049(5) Uiso d . 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 0.0161(3) 0.0151(4) 0.0187(4) 0.0031(3) -0.0031(3) 0.0017(3)
    O2 0.0197(4) 0.0144(4) 0.0176(3) 0.0040(3) 0.0029(3) 0.0005(3)
    O3 0.0190(4) 0.0170(4) 0.0179(3) 0.0025(3) -0.0051(3) 0.0005(3)
    O4 0.0285(4) 0.0150(4) 0.0210(4) 0.0010(3) 0.0023(3) 0.0054(3)
    O5 0.0161(3) 0.0181(4) 0.0234(4) 0.0026(3) 0.0032(3) -0.0025(3)
    N1 0.0159(4) 0.0110(4) 0.0155(4) -0.0001(3) -0.0015(3) -0.0010(3)
    C1 0.0114(4) 0.0132(4) 0.0136(4) 0.0000(3) -0.0003(3) 0.0021(3)
    C2 0.0142(4) 0.0156(5) 0.0135(4) -0.0011(3) -0.0018(3) -0.0004(3)
    C3 0.0152(4) 0.0138(4) 0.0138(4) -0.0011(3) 0.0000(3) -0.0021(3)
    C4 0.0122(4) 0.0110(4) 0.0133(4) 0.0007(3) 0.0005(3) 0.0008(3)
    C5 0.0120(4) 0.0112(4) 0.0114(4) -0.0010(3) 0.0002(3) -0.0001(3)
    C6 0.0143(4) 0.0130(4) 0.0122(4) -0.0011(3) -0.0012(3) 0.0005(3)
    C7 0.0203(5) 0.0157(5) 0.0150(4) -0.0008(4) -0.0030(3) -0.0026(4)
    C8 0.0204(5) 0.0144(5) 0.0153(4) -0.0006(4) -0.0005(3) -0.0035(3)
    C9 0.0155(4) 0.0123(4) 0.0141(4) -0.0002(3) 0.0031(3) 0.0002(3)
    C10 0.0123(4) 0.0110(4) 0.0124(4) 0.0001(3) 0.0011(3) 0.0004(3)
_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 C1 . 1.3388(11) ?
    O1 H1O1 . 0.89(2) ?
    O2 C9 . 1.2367(12) ?
    O3 C6 . 1.2211(12) ?
    O4 N1 . 1.2229(11) ?
    O5 N1 . 1.2274(11) ?
    N1 C4 . 1.4741(12) ?
    C1 C2 . 1.4031(14) ?
    C1 C10 . 1.4091(13) ?
    C2 C3 . 1.3793(14) ?
    C2 H2 . 0.969(15) ?
    C3 C4 . 1.3964(13) ?
    C3 H3 . 0.970(15) ?
    C4 C5 . 1.3836(13) ?
    C5 C10 . 1.4087(13) ?
    C5 C6 . 1.4921(13) ?
    C6 C7 . 1.4744(14) ?
    C7 C8 . 1.3369(15) ?
    C7 H7 . 0.982(16) ?
    C8 C9 . 1.4748(14) ?
    C8 H8 . 0.950(15) ?
    C9 C10 . 1.4699(13) ?
loop_
    _geom_contact_atom_site_label_1
    _geom_contact_atom_site_label_2
    _geom_contact_distance
    _geom_contact_site_symmetry_1
    _geom_contact_site_symmetry_2
    _geom_contact_publ_flag
    Cg1 Cg2 3.7188(6) . 3_756 y
    Cg1 Cg2 3.8299(6) . 3_756 y
    O2 O5 2.9940(11) . 3_756 y
    O5 O5 3.0367(11) . 3_746 y
    O5 N1 3.0608(11) . 3_746 y
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 O1 H1O1 . . 107.7(12) ?
    O4 N1 O5 . . 124.96(9) ?
    O4 N1 C4 . . 117.90(8) ?
    O5 N1 C4 . . 117.04(8) ?
    O1 C1 C2 . . 118.06(8) ?
    O1 C1 C10 . . 121.79(9) ?
    C2 C1 C10 . . 120.15(9) ?
    C3 C2 C1 . . 119.94(9) ?
    C3 C2 H2 . . 121.4(9) ?
    C1 C2 H2 . . 118.6(9) ?
    C2 C3 C4 . . 119.26(9) ?
    C2 C3 H3 . . 121.6(9) ?
    C4 C3 H3 . . 119.1(9) ?
    C5 C4 C3 . . 122.53(9) ?
    C5 C4 N1 . . 121.19(8) ?
    C3 C4 N1 . . 116.27(8) ?
    C4 C5 C10 . . 118.10(8) ?
    C4 C5 C6 . . 122.07(8) ?
    C10 C5 C6 . . 119.72(8) ?
    O3 C6 C7 . . 120.63(9) ?
    O3 C6 C5 . . 121.69(9) ?
    C7 C6 C5 . . 117.58(8) ?
    C8 C7 C6 . . 122.22(9) ?
    C8 C7 H7 . . 121.9(10) ?
    C6 C7 H7 . . 115.8(9) ?
    C7 C8 C9 . . 121.51(9) ?
    C7 C8 H8 . . 122.7(9) ?
    C9 C8 H8 . . 115.8(9) ?
    O2 C9 C10 . . 121.66(9) ?
    O2 C9 C8 . . 119.96(9) ?
    C10 C9 C8 . . 118.38(9) ?
    C5 C10 C1 . . 119.86(9) ?
    C5 C10 C9 . . 120.27(8) ?
    C1 C10 C9 . . 119.86(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
    O1 C1 C2 C3 . . . . -177.19(9) ?
    C10 C1 C2 C3 . . . . 3.41(15) ?
    C1 C2 C3 C4 . . . . -1.45(15) ?
    C2 C3 C4 C5 . . . . -2.37(15) ?
    C2 C3 C4 N1 . . . . 176.71(9) ?
    O4 N1 C4 C5 . . . . 72.88(12) ?
    O5 N1 C4 C5 . . . . -110.47(10) ?
    O4 N1 C4 C3 . . . . -106.21(10) ?
    O5 N1 C4 C3 . . . . 70.44(11) ?
    C3 C4 C5 C10 . . . . 4.07(14) ?
    N1 C4 C5 C10 . . . . -174.97(8) ?
    C3 C4 C5 C6 . . . . -172.05(9) ?
    N1 C4 C5 C6 . . . . 8.92(14) ?
    C4 C5 C6 O3 . . . . 4.45(15) ?
    C10 C5 C6 O3 . . . . -171.60(9) ?
    C4 C5 C6 C7 . . . . -179.01(9) ?
    C10 C5 C6 C7 . . . . 4.94(13) ?
    O3 C6 C7 C8 . . . . 175.40(10) ?
    C5 C6 C7 C8 . . . . -1.17(15) ?
    C6 C7 C8 C9 . . . . -0.45(16) ?
    C7 C8 C9 O2 . . . . 178.62(10) ?
    C7 C8 C9 C10 . . . . -1.51(15) ?
    C4 C5 C10 C1 . . . . -2.00(14) ?
    C6 C5 C10 C1 . . . . 174.21(8) ?
    C4 C5 C10 C9 . . . . 176.79(8) ?
    C6 C5 C10 C9 . . . . -7.00(14) ?
    O1 C1 C10 C5 . . . . 178.97(9) ?
    C2 C1 C10 C5 . . . . -1.65(14) ?
    O1 C1 C10 C9 . . . . 0.17(14) ?
    C2 C1 C10 C9 . . . . 179.56(9) ?
    O2 C9 C10 C5 . . . . -174.82(9) ?
    C8 C9 C10 C5 . . . . 5.31(14) ?
    O2 C9 C10 C1 . . . . 3.97(15) ?
    C8 C9 C10 C1 . . . . -175.90(9) ?
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
    O1 H1O1 O2 . 0.889(18) 1.769(19) 2.5695(10) 148.5(16) y
    C2 H2 O3 4_555 0.969(15) 2.547(16) 3.1853(12) 123.4(12) y
    C3 H3 O5 3_746 0.970(15) 2.577(15) 3.3827(13) 140.6(11) y
    C7 H7 O1 4_666 0.982(16) 2.561(16) 3.1851(13) 121.4(12) y
    C8 H8 Cg1 2_656 0.950(15) 2.976(14) 3.6548(11) 129.5(11) y