##############################################################################
###                                                                        ###
###        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 2.1.    #
#                                                                            #
# 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/  #
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#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_global
_audit_creation_method     'from SHELXL97 CIF and IUCr SHELXL97-template'
_journal_date_recd_electronic     2006-12-19
_journal_date_accepted     2007-01-29
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      3
_journal_page_first     o1115
_journal_page_last     o1116
_journal_paper_category     EO
_journal_coeditor_code     CS2029
_publ_contact_author_name     'Dr Andrew C. Try'
_publ_contact_author_address
; Department of Chemistry and Biomolecular Sciences,
Building F7B,
Macquarie University,
NSW 2109,
Australia
;
_publ_contact_author_email     andrew.try@mq.edu.au
_publ_contact_author_fax     '612 9850 8313'
_publ_contact_author_phone     '612 9850 8291'
_publ_section_title
;
4-(2-Methoxy-4-nitrophenyl)morpholine-3,5-dione
;
loop_
    _publ_author_name
    _publ_author_address
    'Bhuiyan, M. Delower H.'
; Department of Chemistry and Biomolecular Sciences,
Building F7B,
Macquarie University,
NSW 2109, Australia
;
    'Jensen, Paul'
; Crystal Structure Analysis Facility,
School of Chemistry, F11,
The University of Sydney,
NSW 2006,
Australia
;
    'Turner, Peter'
; Crystal Structure Analysis Facility,
School of Chemistry, F11,
The University of Sydney,
NSW 2006,
Australia
;
    'Try, Andrew C.'
; Department of Chemistry and Biomolecular Sciences,
Building F7B,
Macquarie University,
NSW 2109, Australia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
4-(2-methoxy-4-nitrophenyl)morpholine-3,5-dione
;
_chemical_name_common     ?
_chemical_formula_moiety     'C11 H10 N2 O6'
_chemical_formula_sum     'C11 H10 N2 O6'
_chemical_formula_iupac     'C11 H10 N2 O6'
_chemical_formula_weight     266.21
_chemical_melting_point     486
_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     7.526(2)
_cell_length_b     7.554(2)
_cell_length_c     10.259(3)
_cell_angle_alpha     100.460(4)
_cell_angle_beta     102.539(4)
_cell_angle_gamma     94.732(4)
_cell_volume     555.3(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     863
_cell_measurement_theta_min     3.063
_cell_measurement_theta_max     28.174
_cell_measurement_temperature     150(2)
_exptl_crystal_description     Prism
_exptl_crystal_colour     Yellow
_exptl_crystal_size_max     0.538
_exptl_crystal_size_mid     0.319
_exptl_crystal_size_min     0.287
_exptl_crystal_density_diffrn     1.592
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     276
_exptl_absorpt_coefficient_mu     0.132
_exptl_absorpt_correction_type     Gaussian
_exptl_absorpt_process_details
;
[GAUSSIAN (Coppens et al.,  1965) and XPREP (Siemens,
1995)]
;
_exptl_absorpt_correction_T_min     0.939
_exptl_absorpt_correction_T_max     0.972
_diffrn_ambient_temperature     150(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 SMART 1000 CCD'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     5320
_diffrn_reflns_av_R_equivalents     0.0302
_diffrn_reflns_av_sigmaI/netI     0.0273
_diffrn_reflns_theta_min     2.08
_diffrn_reflns_theta_max     27.10
_diffrn_reflns_theta_full     27.10
_diffrn_measured_fraction_theta_max     0.989
_diffrn_measured_fraction_theta_full     0.989
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_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 > 2sigma(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     2433
_reflns_number_gt     2109
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0369
_refine_ls_R_factor_gt     0.0322
_refine_ls_wR_factor_gt     0.0881
_refine_ls_wR_factor_ref     0.0916
_refine_ls_goodness_of_fit_ref     1.085
_refine_ls_restrained_S_all     1.085
_refine_ls_number_reflns     2433
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
          'calc w=1/[σ²(Fo²)+(0.046P)²+0.1137P] 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     0.271
_refine_diff_density_min     -0.260
_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     'SMART (Siemens, 1995)'
_computing_cell_refinement     'SMART (Siemens, 1995)'
_computing_data_reduction     'SAINT and XPREP (Siemens, 1995)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
;
Xtal3.6 (Hall et al.,  1999),
ORTEPII (Johnson, 1976),
and WinGX (Farrugia, 1999)
;
_computing_publication_material     WinGX
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
    N N1 0.79995(13) -0.32869(13) 0.13488(11) 0.0225(2) Uani d . 1 . .
    N N2 0.40014(12) 0.23002(12) 0.30811(9) 0.0181(2) Uani d . 1 . .
    O O1 0.93364(12) -0.35848(12) 0.21646(10) 0.0341(2) Uani d . 1 . .
    O O2 0.75368(12) -0.40508(12) 0.01449(9) 0.0298(2) Uani d . 1 . .
    O O3 0.24896(10) -0.02408(10) 0.07797(8) 0.02107(19) Uani d . 1 . .
    O O4 0.27752(11) 0.52558(11) 0.43958(8) 0.0246(2) Uani d . 1 . .
    O O5 0.19626(11) 0.04616(11) 0.37299(9) 0.0265(2) Uani d . 1 . .
    O O6 0.58401(11) 0.41966(11) 0.22981(9) 0.0252(2) Uani d . 1 . .
    C C1 0.68987(15) -0.18997(14) 0.18464(12) 0.0186(2) Uani d . 1 . .
    C C2 0.51785(15) -0.18451(14) 0.10317(11) 0.0181(2) Uani d . 1 . .
    H H2 0.4698 -0.2713 0.0207 0.022 Uiso calc R 1 . .
    C C3 0.41798(14) -0.04716(14) 0.14657(11) 0.0173(2) Uani d . 1 . .
    C C4 0.49643(15) 0.07950(14) 0.26773(11) 0.0177(2) Uani d . 1 . .
    C C5 0.66624(15) 0.06711(15) 0.34738(12) 0.0209(2) Uani d . 1 . .
    H H5 0.7149 0.1529 0.4303 0.025 Uiso calc R 1 . .
    C C6 0.76636(15) -0.07093(15) 0.30651(12) 0.0212(2) Uani d . 1 . .
    H H6 0.8828 -0.0825 0.3606 0.025 Uiso calc R 1 . .
    C C7 0.24866(15) 0.19713(15) 0.36230(11) 0.0199(2) Uani d . 1 . .
    C C8 0.15673(16) 0.36161(16) 0.40643(13) 0.0255(3) Uani d . 1 . .
    H H8A 0.0510 0.3691 0.3319 0.031 Uiso calc R 1 . .
    H H8B 0.1091 0.3463 0.4869 0.031 Uiso calc R 1 . .
    C C9 0.35197(17) 0.55177(15) 0.32763(12) 0.0235(3) Uani d . 1 . .
    H H9A 0.4337 0.6684 0.3533 0.028 Uiso calc R 1 . .
    H H9B 0.2510 0.5591 0.2496 0.028 Uiso calc R 1 . .
    C C10 0.45934(15) 0.39991(15) 0.28422(11) 0.0189(2) Uani d . 1 . .
    C C11 0.15733(16) -0.16597(16) -0.03647(12) 0.0237(3) Uani d . 1 . .
    H H11A 0.2304 -0.1785 -0.1052 0.036 Uiso calc R 1 . .
    H H11B 0.0361 -0.1353 -0.0764 0.036 Uiso calc R 1 . .
    H H11C 0.1431 -0.2807 -0.0057 0.036 Uiso calc R 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
    N1 0.0186(5) 0.0171(5) 0.0328(6) 0.0037(4) 0.0082(4) 0.0048(4)
    N2 0.0183(5) 0.0157(4) 0.0199(5) 0.0030(3) 0.0058(4) 0.0006(4)
    O1 0.0209(4) 0.0292(5) 0.0479(6) 0.0111(4) 0.0002(4) 0.0032(4)
    O2 0.0336(5) 0.0256(5) 0.0309(5) 0.0110(4) 0.0112(4) 0.0004(4)
    O3 0.0184(4) 0.0197(4) 0.0218(4) 0.0061(3) 0.0005(3) -0.0008(3)
    O4 0.0289(4) 0.0211(4) 0.0233(4) 0.0046(3) 0.0096(3) -0.0016(3)
    O5 0.0243(4) 0.0240(4) 0.0317(5) -0.0003(3) 0.0100(4) 0.0049(4)
    O6 0.0279(4) 0.0217(4) 0.0294(5) 0.0041(3) 0.0133(4) 0.0056(3)
    C1 0.0181(5) 0.0139(5) 0.0262(6) 0.0042(4) 0.0086(4) 0.0052(4)
    C2 0.0194(5) 0.0152(5) 0.0194(5) 0.0018(4) 0.0053(4) 0.0023(4)
    C3 0.0169(5) 0.0165(5) 0.0196(5) 0.0025(4) 0.0048(4) 0.0055(4)
    C4 0.0187(5) 0.0147(5) 0.0210(5) 0.0027(4) 0.0078(4) 0.0034(4)
    C5 0.0209(5) 0.0186(5) 0.0206(6) 0.0001(4) 0.0032(4) 0.0005(4)
    C6 0.0165(5) 0.0216(5) 0.0250(6) 0.0029(4) 0.0029(4) 0.0059(5)
    C7 0.0171(5) 0.0233(6) 0.0172(5) 0.0014(4) 0.0027(4) 0.0011(4)
    C8 0.0223(6) 0.0254(6) 0.0296(6) 0.0048(5) 0.0102(5) 0.0018(5)
    C9 0.0283(6) 0.0193(6) 0.0242(6) 0.0065(5) 0.0086(5) 0.0035(5)
    C10 0.0213(5) 0.0169(5) 0.0167(5) 0.0019(4) 0.0027(4) 0.0015(4)
    C11 0.0192(5) 0.0231(6) 0.0240(6) 0.0046(4) -0.0003(4) -0.0023(5)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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 O2 . 1.2251(14) ?
    N1 O1 . 1.2262(14) ?
    N1 C1 . 1.4756(14) ?
    N2 C7 . 1.3961(14) ?
    N2 C10 . 1.4046(14) ?
    N2 C4 . 1.4440(13) ?
    O3 C3 . 1.3551(13) ?
    O3 C11 . 1.4396(14) ?
    O4 C8 . 1.4154(15) ?
    O4 C9 . 1.4198(15) ?
    O5 C7 . 1.2075(14) ?
    O6 C10 . 1.2037(14) ?
    C1 C6 . 1.3774(16) ?
    C1 C2 . 1.3885(16) ?
    C2 C3 . 1.3949(15) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.4019(15) ?
    C4 C5 . 1.3798(16) ?
    C5 C6 . 1.3925(16) ?
    C5 H5 . 0.9500 ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.5169(16) ?
    C8 H8A . 0.9900 ?
    C8 H8B . 0.9900 ?
    C9 C10 . 1.5136(15) ?
    C9 H9A . 0.9900 ?
    C9 H9B . 0.9900 ?
    C11 H11A . 0.9800 ?
    C11 H11B . 0.9800 ?
    C11 H11C . 0.9800 ?
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 . . 124.11(10) ?
    O2 N1 C1 . . 118.09(9) ?
    O1 N1 C1 . . 117.79(10) ?
    C7 N2 C10 . . 123.71(9) ?
    C7 N2 C4 . . 118.44(9) ?
    C10 N2 C4 . . 117.77(9) ?
    C3 O3 C11 . . 116.97(8) ?
    C8 O4 C9 . . 111.09(9) ?
    C6 C1 C2 . . 124.24(10) ?
    C6 C1 N1 . . 118.03(10) ?
    C2 C1 N1 . . 117.69(10) ?
    C1 C2 C3 . . 117.69(10) ?
    C1 C2 H2 . . 121.2 ?
    C3 C2 H2 . . 121.2 ?
    O3 C3 C2 . . 124.48(10) ?
    O3 C3 C4 . . 116.60(9) ?
    C2 C3 C4 . . 118.91(10) ?
    C5 C4 C3 . . 121.61(10) ?
    C5 C4 N2 . . 119.05(10) ?
    C3 C4 N2 . . 119.30(9) ?
    C4 C5 C6 . . 120.11(10) ?
    C4 C5 H5 . . 119.9 ?
    C6 C5 H5 . . 119.9 ?
    C1 C6 C5 . . 117.36(10) ?
    C1 C6 H6 . . 121.3 ?
    C5 C6 H6 . . 121.3 ?
    O5 C7 N2 . . 121.20(10) ?
    O5 C7 C8 . . 122.90(10) ?
    N2 C7 C8 . . 115.90(10) ?
    O4 C8 C7 . . 112.59(9) ?
    O4 C8 H8A . . 109.1 ?
    C7 C8 H8A . . 109.1 ?
    O4 C8 H8B . . 109.1 ?
    C7 C8 H8B . . 109.1 ?
    H8A C8 H8B . . 107.8 ?
    O4 C9 C10 . . 112.13(9) ?
    O4 C9 H9A . . 109.2 ?
    C10 C9 H9A . . 109.2 ?
    O4 C9 H9B . . 109.2 ?
    C10 C9 H9B . . 109.2 ?
    H9A C9 H9B . . 107.9 ?
    O6 C10 N2 . . 121.45(10) ?
    O6 C10 C9 . . 123.25(10) ?
    N2 C10 C9 . . 115.27(9) ?
    O3 C11 H11A . . 109.5 ?
    O3 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    O3 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
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 C6 . . . . -162.82(10) ?
    O1 N1 C1 C6 . . . . 16.23(15) ?
    O2 N1 C1 C2 . . . . 15.20(15) ?
    O1 N1 C1 C2 . . . . -165.75(10) ?
    C6 C1 C2 C3 . . . . 1.33(17) ?
    N1 C1 C2 C3 . . . . -176.56(9) ?
    C11 O3 C3 C2 . . . . 9.19(15) ?
    C11 O3 C3 C4 . . . . -172.13(10) ?
    C1 C2 C3 O3 . . . . 179.80(10) ?
    C1 C2 C3 C4 . . . . 1.15(15) ?
    O3 C3 C4 C5 . . . . 178.63(10) ?
    C2 C3 C4 C5 . . . . -2.62(16) ?
    O3 C3 C4 N2 . . . . -3.40(15) ?
    C2 C3 C4 N2 . . . . 175.35(9) ?
    C7 N2 C4 C5 . . . . -106.57(12) ?
    C10 N2 C4 C5 . . . . 76.49(14) ?
    C7 N2 C4 C3 . . . . 75.41(13) ?
    C10 N2 C4 C3 . . . . -101.53(12) ?
    C3 C4 C5 C6 . . . . 1.63(17) ?
    N2 C4 C5 C6 . . . . -176.34(10) ?
    C2 C1 C6 C5 . . . . -2.31(17) ?
    N1 C1 C6 C5 . . . . 175.57(10) ?
    C4 C5 C6 C1 . . . . 0.79(17) ?
    C10 N2 C7 O5 . . . . 175.29(10) ?
    C4 N2 C7 O5 . . . . -1.45(16) ?
    C10 N2 C7 C8 . . . . -4.92(15) ?
    C4 N2 C7 C8 . . . . 178.34(9) ?
    C9 O4 C8 C7 . . . . 57.74(13) ?
    O5 C7 C8 O4 . . . . 154.73(11) ?
    N2 C7 C8 O4 . . . . -25.06(14) ?
    C8 O4 C9 C10 . . . . -60.01(12) ?
    C7 N2 C10 O6 . . . . -175.51(10) ?
    C4 N2 C10 O6 . . . . 1.26(16) ?
    C7 N2 C10 C9 . . . . 2.73(15) ?
    C4 N2 C10 C9 . . . . 179.49(9) ?
    O4 C9 C10 O6 . . . . -152.49(11) ?
    O4 C9 C10 N2 . . . . 29.32(13) ?
