##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2009-08-20
_journal_date_accepted     2009-08-24
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      9
_journal_page_first     o2263
_journal_page_last     o2263
_journal_paper_category     QO
_journal_coeditor_code     CV2603
_publ_contact_author_name     'Prof. Soon W. Lee'
_publ_contact_author_address
;
Department of Chemistry (BK21)
Sungkyunkwan University
Natural Science Campus
Suwon 440-746
Republic of Korea
;
_publ_contact_author_email     soonwlee@skku.edu
_publ_contact_author_fax     '82(31)2907075'
_publ_contact_author_phone     '82(31)2907066'
_publ_section_title
;
N,N'-Bis[(E)-4-nitrobenzylidene]-4,4'-oxydianiline
;
loop_
    _publ_author_name
    _publ_author_address
    'Lee, Hee K.'
;
Department of Chemistry (BK21)
Sungkyunkwan University
Natural Science Campus
Suwon 440-746
Republic of Korea
;
    'Lee, Soon W.'
;
Department of Chemistry (BK21)
Sungkyunkwan University
Natural Science Campus
Suwon 440-746
Republic of Korea
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
N,N'-Bis[(E)-4-nitrobenzylidene]-4,4'-oxydianiline
;
_chemical_name_common     ?
_chemical_formula_moiety     'C26 H18 N4 O5'
_chemical_formula_sum     'C26 H18 N4 O5'
_chemical_formula_iupac     'C26 H18 N4 O5'
_chemical_formula_weight     466.44
_chemical_melting_point     ?
_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     8.3322(11)
_cell_length_b     9.0716(16)
_cell_length_c     17.107(2)
_cell_angle_alpha     74.714(9)
_cell_angle_beta     78.885(10)
_cell_angle_gamma     64.643(10)
_cell_volume     1122.4(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     23
_cell_measurement_theta_min     5.19
_cell_measurement_theta_max     12.50
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.52
_exptl_crystal_size_mid     0.32
_exptl_crystal_size_min     0.26
_exptl_crystal_density_diffrn     1.380
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     484
_exptl_absorpt_coefficient_mu     0.098
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     'MoK\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'sealed tube'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device     'Siemens P4'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     4200
_diffrn_reflns_av_R_equivalents     0.0150
_diffrn_reflns_av_sigmaI/netI     0.0272
_diffrn_reflns_theta_min     2.48
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.989
_diffrn_measured_fraction_theta_full     0.989
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -19
_diffrn_reflns_limit_l_max     20
_diffrn_standards_number     3
_diffrn_standards_interval_count     97
_diffrn_standards_interval_time     ?
_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 >
σ(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     3909
_reflns_number_gt     2972
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0571
_refine_ls_R_factor_gt     0.0409
_refine_ls_wR_factor_gt     0.1033
_refine_ls_wR_factor_ref     0.1144
_refine_ls_goodness_of_fit_ref     1.022
_refine_ls_restrained_S_all     1.022
_refine_ls_number_reflns     3909
_refine_ls_number_parameters     389
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0503P)²+0.1958P] 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     0.137
_refine_diff_density_min     -0.193
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0142(18)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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     'XSCANS (Siemens, 1995)'
_computing_cell_refinement     'XSCANS (Siemens, 1995)'
_computing_data_reduction     'XSCANS (Siemens, 1995)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
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 1.7461(2) -1.5786(2) 0.74989(10) 0.1006(6) Uani d . 1 . .
    O O2 1.8293(3) -1.6837(2) 0.64341(12) 0.1072(6) Uani d . 1 . .
    O O3 0.66294(17) -0.41925(15) 0.27173(8) 0.0675(4) Uani d . 1 . .
    O O4 0.8910(2) 0.87019(18) -0.12942(11) 0.0838(5) Uani d . 1 . .
    O O5 0.7292(3) 0.9709(2) -0.02700(11) 0.1184(7) Uani d . 1 . .
    N N1 1.7396(2) -1.5702(2) 0.67832(12) 0.0737(5) Uani d . 1 . .
    N N2 1.2107(2) -0.96099(19) 0.43282(10) 0.0631(4) Uani d . 1 . .
    N N3 0.6330(2) 0.22173(17) 0.13724(9) 0.0556(4) Uani d . 1 . .
    N N4 0.7983(2) 0.86027(19) -0.06546(11) 0.0667(4) Uani d . 1 . .
    C C1 1.6151(2) -1.4143(2) 0.63208(11) 0.0561(4) Uani d . 1 . .
    C C2 1.5930(3) -1.4084(3) 0.55334(13) 0.0697(5) Uani d . 1 . .
    C C3 1.4715(3) -1.2638(3) 0.51122(13) 0.0692(5) Uani d . 1 . .
    C C4 1.3747(2) -1.1275(2) 0.54727(11) 0.0567(4) Uani d . 1 . .
    C C5 1.4043(3) -1.1372(3) 0.62583(12) 0.0666(5) Uani d . 1 . .
    C C6 1.5244(3) -1.2814(3) 0.66859(12) 0.0646(5) Uani d . 1 . .
    C C7 1.2366(3) -0.9765(3) 0.50481(13) 0.0640(5) Uani d . 1 . .
    C C8 1.0753(2) -0.8152(2) 0.39338(11) 0.0557(4) Uani d . 1 . .
    C C9 1.0170(3) -0.8290(2) 0.32617(11) 0.0614(5) Uani d . 1 . .
    C C10 0.8827(3) -0.6950(2) 0.28467(12) 0.0603(5) Uani d . 1 . .
    C C11 0.8091(2) -0.5460(2) 0.30985(11) 0.0554(4) Uani d . 1 . .
    C C12 0.8703(3) -0.5267(2) 0.37428(12) 0.0640(5) Uani d . 1 . .
    C C13 1.0025(3) -0.6607(2) 0.41617(13) 0.0650(5) Uani d . 1 . .
    C C14 0.6656(2) -0.2624(2) 0.24132(10) 0.0527(4) Uani d . 1 . .
    C C15 0.5020(2) -0.1291(2) 0.23764(11) 0.0570(4) Uani d . 1 . .
    C C16 0.4942(2) 0.0295(2) 0.20338(11) 0.0560(4) Uani d . 1 . .
    C C17 0.6481(2) 0.0556(2) 0.17089(9) 0.0504(4) Uani d . 1 . .
    C C18 0.8120(2) -0.0792(2) 0.17666(11) 0.0565(4) Uani d . 1 . .
    C C19 0.8211(2) -0.2388(2) 0.21218(11) 0.0569(4) Uani d . 1 . .
    C C20 0.7171(2) 0.2500(2) 0.06917(11) 0.0534(4) Uani d . 1 . .
    C C21 0.7241(2) 0.4137(2) 0.03302(10) 0.0495(4) Uani d . 1 . .
    C C22 0.8183(3) 0.4350(2) -0.04281(11) 0.0580(5) Uani d . 1 . .
    C C23 0.8408(3) 0.5821(2) -0.07591(12) 0.0588(5) Uani d . 1 . .
    C C24 0.7657(2) 0.70731(19) -0.03286(11) 0.0527(4) Uani d . 1 . .
    C C25 0.6657(3) 0.6929(2) 0.04074(11) 0.0606(5) Uani d . 1 . .
    C C26 0.6447(3) 0.5455(2) 0.07374(11) 0.0567(4) Uani d . 1 . .
    H H2 1.657(3) -1.501(3) 0.5313(12) 0.079(6) Uiso d . 1 . .
    H H3 1.454(3) -1.258(3) 0.4561(14) 0.089(7) Uiso d . 1 . .
    H H5 1.332(3) -1.034(3) 0.6515(13) 0.089(7) Uiso d . 1 . .
    H H6 1.542(3) -1.293(2) 0.7242(13) 0.077(6) Uiso d . 1 . .
    H H7 1.167(3) -0.892(3) 0.5362(14) 0.099(8) Uiso d . 1 . .
    H H9 1.073(3) -0.939(2) 0.3098(11) 0.072(6) Uiso d . 1 . .
    H H10 0.839(3) -0.707(2) 0.2398(12) 0.077(6) Uiso d . 1 . .
    H H12 0.822(3) -0.421(3) 0.3907(12) 0.075(6) Uiso d . 1 . .
    H H13 1.044(2) -0.650(2) 0.4595(12) 0.063(5) Uiso d . 1 . .
    H H15 0.397(3) -0.151(2) 0.2596(11) 0.071(6) Uiso d . 1 . .
    H H16 0.381(3) 0.125(2) 0.2019(11) 0.071(6) Uiso d . 1 . .
    H H18 0.923(3) -0.061(2) 0.1556(11) 0.063(5) Uiso d . 1 . .
    H H19 0.934(3) -0.331(2) 0.2162(11) 0.064(5) Uiso d . 1 . .
    H H20 0.784(3) 0.161(2) 0.0355(11) 0.066(5) Uiso d . 1 . .
    H H22 0.876(3) 0.342(2) -0.0724(11) 0.071(6) Uiso d . 1 . .
    H H23 0.904(3) 0.597(2) -0.1244(12) 0.075(6) Uiso d . 1 . .
    H H25 0.616(3) 0.777(2) 0.0689(12) 0.071(6) Uiso d . 1 . .
    H H26 0.577(3) 0.528(2) 0.1242(12) 0.069(6) Uiso d . 1 . .
_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 . 1.217(2) ?
    O2 N1 . 1.211(2) ?
    O3 C14 . 1.388(2) ?
    O3 C11 . 1.394(2) ?
    O4 N4 . 1.218(2) ?
    O5 N4 . 1.216(2) ?
    N1 C1 . 1.474(2) ?
    N2 C7 . 1.252(3) ?
    N2 C8 . 1.422(2) ?
    N3 C20 . 1.262(2) ?
    N3 C17 . 1.424(2) ?
    N4 C24 . 1.472(2) ?
    C1 C6 . 1.360(3) ?
    C1 C2 . 1.378(3) ?
    C2 C3 . 1.382(3) ?
    C2 H2 . 0.92(2) ?
    C3 C4 . 1.384(3) ?
    C3 H3 . 0.97(2) ?
    C4 C5 . 1.386(3) ?
    C4 C7 . 1.475(3) ?
    C5 C6 . 1.380(3) ?
    C5 H5 . 1.03(2) ?
    C6 H6 . 0.96(2) ?
    C7 H7 . 0.96(2) ?
    C8 C9 . 1.385(3) ?
    C8 C13 . 1.397(3) ?
    C9 C10 . 1.386(3) ?
    C9 H9 . 0.99(2) ?
    C10 C11 . 1.373(3) ?
    C10 H10 . 0.96(2) ?
    C11 C12 . 1.379(3) ?
    C12 C13 . 1.379(3) ?
    C12 H12 . 0.97(2) ?
    C13 H13 . 0.920(19) ?
    C14 C19 . 1.380(2) ?
    C14 C15 . 1.381(2) ?
    C15 C16 . 1.381(2) ?
    C15 H15 . 0.97(2) ?
    C16 C17 . 1.387(2) ?
    C16 H16 . 0.97(2) ?
    C17 C18 . 1.389(2) ?
    C18 C19 . 1.389(2) ?
    C18 H18 . 0.990(19) ?
    C19 H19 . 0.956(19) ?
    C20 C21 . 1.472(2) ?
    C20 H20 . 1.016(19) ?
    C21 C26 . 1.392(2) ?
    C21 C22 . 1.393(2) ?
    C22 C23 . 1.383(3) ?
    C22 H22 . 0.99(2) ?
    C23 C24 . 1.371(3) ?
    C23 H23 . 0.90(2) ?
    C24 C25 . 1.378(3) ?
    C25 C26 . 1.378(3) ?
    C25 H25 . 0.92(2) ?
    C26 H26 . 0.953(19) ?
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
    C14 O3 C11 . . 118.85(13) ?
    O2 N1 O1 . . 123.39(19) ?
    O2 N1 C1 . . 118.48(19) ?
    O1 N1 C1 . . 118.1(2) ?
    C7 N2 C8 . . 120.80(18) ?
    C20 N3 C17 . . 118.44(15) ?
    O5 N4 O4 . . 123.56(17) ?
    O5 N4 C24 . . 117.74(18) ?
    O4 N4 C24 . . 118.69(16) ?
    C6 C1 C2 . . 122.07(18) ?
    C6 C1 N1 . . 119.08(18) ?
    C2 C1 N1 . . 118.85(19) ?
    C1 C2 C3 . . 118.6(2) ?
    C1 C2 H2 . . 119.0(13) ?
    C3 C2 H2 . . 122.4(13) ?
    C2 C3 C4 . . 120.64(19) ?
    C2 C3 H3 . . 119.7(13) ?
    C4 C3 H3 . . 119.6(13) ?
    C3 C4 C5 . . 118.88(18) ?
    C3 C4 C7 . . 121.08(18) ?
    C5 C4 C7 . . 119.99(19) ?
    C6 C5 C4 . . 120.9(2) ?
    C6 C5 H5 . . 121.3(12) ?
    C4 C5 H5 . . 117.8(12) ?
    C1 C6 C5 . . 118.84(19) ?
    C1 C6 H6 . . 118.9(12) ?
    C5 C6 H6 . . 122.2(12) ?
    N2 C7 C4 . . 121.7(2) ?
    N2 C7 H7 . . 122.5(14) ?
    C4 C7 H7 . . 115.8(14) ?
    C9 C8 C13 . . 118.62(17) ?
    C9 C8 N2 . . 116.51(17) ?
    C13 C8 N2 . . 124.84(17) ?
    C8 C9 C10 . . 120.91(19) ?
    C8 C9 H9 . . 117.4(11) ?
    C10 C9 H9 . . 121.7(11) ?
    C11 C10 C9 . . 119.33(19) ?
    C11 C10 H10 . . 120.1(12) ?
    C9 C10 H10 . . 120.6(12) ?
    C10 C11 C12 . . 120.95(17) ?
    C10 C11 O3 . . 117.62(17) ?
    C12 C11 O3 . . 121.29(17) ?
    C11 C12 C13 . . 119.60(19) ?
    C11 C12 H12 . . 121.1(12) ?
    C13 C12 H12 . . 119.3(12) ?
    C12 C13 C8 . . 120.5(2) ?
    C12 C13 H13 . . 120.5(12) ?
    C8 C13 H13 . . 119.0(12) ?
    C19 C14 C15 . . 120.83(16) ?
    C19 C14 O3 . . 122.74(16) ?
    C15 C14 O3 . . 116.35(15) ?
    C14 C15 C16 . . 119.40(17) ?
    C14 C15 H15 . . 118.0(11) ?
    C16 C15 H15 . . 122.6(11) ?
    C15 C16 C17 . . 120.79(17) ?
    C15 C16 H16 . . 120.6(12) ?
    C17 C16 H16 . . 118.6(12) ?
    C16 C17 C18 . . 119.11(15) ?
    C16 C17 N3 . . 118.57(15) ?
    C18 C17 N3 . . 122.20(16) ?
    C17 C18 C19 . . 120.35(17) ?
    C17 C18 H18 . . 119.4(10) ?
    C19 C18 H18 . . 120.2(10) ?
    C14 C19 C18 . . 119.44(17) ?
    C14 C19 H19 . . 120.4(11) ?
    C18 C19 H19 . . 120.2(11) ?
    N3 C20 C21 . . 122.54(17) ?
    N3 C20 H20 . . 122.0(10) ?
    C21 C20 H20 . . 115.4(10) ?
    C26 C21 C22 . . 119.25(16) ?
    C26 C21 C20 . . 121.80(16) ?
    C22 C21 C20 . . 118.91(16) ?
    C23 C22 C21 . . 120.78(17) ?
    C23 C22 H22 . . 119.2(11) ?
    C21 C22 H22 . . 120.0(11) ?
    C24 C23 C22 . . 118.32(18) ?
    C24 C23 H23 . . 119.8(13) ?
    C22 C23 H23 . . 121.9(13) ?
    C23 C24 C25 . . 122.38(16) ?
    C23 C24 N4 . . 118.52(17) ?
    C25 C24 N4 . . 119.07(16) ?
    C24 C25 C26 . . 119.05(17) ?
    C24 C25 H25 . . 121.6(12) ?
    C26 C25 H25 . . 119.3(12) ?
    C25 C26 C21 . . 120.13(18) ?
    C25 C26 H26 . . 123.1(12) ?
    C21 C26 H26 . . 116.8(12) ?
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
    C19 H19 O1 2_836 0.956(19) 2.57(2) 3.375(2) 142.4(14)
    C20 H20 O5 1_545 1.016(19) 2.48(2) 3.323(2) 139.7(14)
