##############################################################################
###                                                                        ###
###        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/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2-[2-(2,4-Dinitrophenoxy)ethoxy]-3-methoxybenzaldehyde
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H14 N2 O8'
_chemical_formula_sum     'C16 H14 N2 O8'
_chemical_formula_iupac     'C16 H14 N2 O8'
_chemical_formula_weight     362.29
_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     13.192(2)
_cell_length_b     8.4397(16)
_cell_length_c     14.673(3)
_cell_angle_alpha     90.00
_cell_angle_beta     94.990(3)
_cell_angle_gamma     90.00
_cell_volume     1627.5(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2335
_cell_measurement_theta_min     2.79
_cell_measurement_theta_max     25.36
_cell_measurement_temperature     294(2)
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.32
_exptl_crystal_size_mid     0.24
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.479
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     752
_exptl_absorpt_coefficient_mu     0.121
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.943
_exptl_absorpt_correction_T_max     0.976
_exptl_special_details
;
;
_diffrn_ambient_temperature     294(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 APEX CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     8940
_diffrn_reflns_av_R_equivalents     0.0331
_diffrn_reflns_av_sigmaI/netI     0.0396
_diffrn_reflns_theta_min     1.55
_diffrn_reflns_theta_max     26.42
_diffrn_reflns_theta_full     26.42
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_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     3339
_reflns_number_gt     2001
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0835
_refine_ls_R_factor_gt     0.0426
_refine_ls_wR_factor_gt     0.0997
_refine_ls_wR_factor_ref     0.1191
_refine_ls_goodness_of_fit_ref     1.021
_refine_ls_restrained_S_all     1.021
_refine_ls_number_reflns     3339
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0557P)²+0.1477P] 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     0.216
_refine_diff_density_min     -0.229
_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 (Bruker, 1999)'
_computing_cell_refinement     'SAINT (Bruker, 1999)'
_computing_data_reduction     SAINT
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997a)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997a)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material     SHELXTL
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 0.67715(10) 1.21040(17) 0.09696(9) 0.0556(4) Uani d . 1 . .
    O O2 0.72801(15) 0.8180(2) -0.23092(12) 0.0885(6) Uani d . 1 . .
    O O3 0.79744(9) 1.00787(15) 0.01882(8) 0.0453(4) Uani d . 1 . .
    O O4 0.95083(10) 0.78346(17) 0.05274(8) 0.0497(4) Uani d . 1 . .
    O O5 0.99040(13) 0.7536(3) -0.11816(10) 0.0925(7) Uani d . 1 . .
    O O6 1.08764(14) 0.5625(2) -0.14591(10) 0.0782(5) Uani d . 1 . .
    O O7 1.36279(12) 0.4220(2) 0.06513(12) 0.0770(5) Uani d . 1 . .
    O O8 1.37494(12) 0.5162(2) 0.20253(12) 0.0811(5) Uani d . 1 . .
    N N1 1.05319(13) 0.6550(2) -0.09322(11) 0.0494(4) Uani d . 1 . .
    N N2 1.33005(13) 0.4989(2) 0.12717(14) 0.0558(5) Uani d . 1 . .
    C C1 0.61730(18) 1.3267(3) 0.13857(16) 0.0720(7) Uani d . 1 . .
    H H1A 0.6028 1.4128 0.0967 0.108 Uiso calc R 1 . .
    H H1B 0.6542 1.3656 0.1933 0.108 Uiso calc R 1 . .
    H H1C 0.5546 1.2796 0.1537 0.108 Uiso calc R 1 . .
    C C2 0.63977(14) 1.1512(2) 0.01415(12) 0.0408(5) Uani d . 1 . .
    C C3 0.54728(14) 1.1906(2) -0.03179(14) 0.0498(5) Uani d . 1 . .
    H H3 0.5044 1.2622 -0.0060 0.060 Uiso calc R 1 . .
    C C4 0.51833(15) 1.1235(3) -0.11632(14) 0.0535(6) Uani d . 1 . .
    H H4 0.4559 1.1503 -0.1467 0.064 Uiso calc R 1 . .
    C C5 0.58014(16) 1.0189(3) -0.15547(14) 0.0521(5) Uani d . 1 . .
    H H5 0.5594 0.9740 -0.2119 0.062 Uiso calc R 1 . .
    C C6 0.67461(15) 0.9791(2) -0.11092(13) 0.0435(5) Uani d . 1 . .
    C C7 0.74439(18) 0.8730(3) -0.15521(16) 0.0603(6) Uani d . 1 . .
    H H7 0.8055 0.8465 -0.1223 0.072 Uiso calc R 1 . .
    C C8 0.70374(13) 1.0442(2) -0.02559(12) 0.0396(4) Uani d . 1 . .
    C C9 0.79220(14) 0.8866(2) 0.08677(13) 0.0473(5) Uani d . 1 . .
    H H9A 0.7606 0.7923 0.0593 0.057 Uiso calc R 1 . .
    H H9B 0.7516 0.9229 0.1347 0.057 Uiso calc R 1 . .
    C C10 0.89774(14) 0.8497(3) 0.12602(12) 0.0488(5) Uani d . 1 . .
    H H10A 0.9315 0.9452 0.1495 0.059 Uiso calc R 1 . .
    H H10B 0.8962 0.7741 0.1757 0.059 Uiso calc R 1 . .
    C C11 1.04373(14) 0.7227(2) 0.07304(12) 0.0408(5) Uani d . 1 . .
    C C12 1.09375(13) 0.6501(2) 0.00302(11) 0.0376(4) Uani d . 1 . .
    C C13 1.18546(14) 0.5743(2) 0.02144(13) 0.0424(5) Uani d . 1 . .
    H H13 1.2164 0.5231 -0.0250 0.051 Uiso calc R 1 . .
    C C14 1.23068(14) 0.5751(2) 0.10910(13) 0.0429(5) Uani d . 1 . .
    C C15 1.18634(15) 0.6496(2) 0.17898(13) 0.0485(5) Uani d . 1 . .
    H H15 1.2189 0.6513 0.2378 0.058 Uiso calc R 1 . .
    C C16 1.09369(15) 0.7212(3) 0.16090(13) 0.0504(5) Uani d . 1 . .
    H H16 1.0632 0.7700 0.2084 0.061 Uiso calc R 1 . .
_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
    O1 C2 . 1.366(2) ?
    O1 C1 . 1.429(2) ?
    O2 C7 . 1.206(3) ?
    O3 C8 . 1.381(2) ?
    O3 C9 . 1.435(2) ?
    O4 C11 . 1.338(2) ?
    O4 C10 . 1.446(2) ?
    O5 N1 . 1.208(2) ?
    O6 N1 . 1.214(2) ?
    O7 N2 . 1.227(2) ?
    O8 N2 . 1.217(2) ?
    N1 C12 . 1.466(2) ?
    N2 C14 . 1.463(3) ?
    C1 H1A . 0.9600 ?
    C1 H1B . 0.9600 ?
    C1 H1C . 0.9600 ?
    C2 C3 . 1.382(3) ?
    C2 C8 . 1.398(3) ?
    C3 C4 . 1.387(3) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.362(3) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.397(3) ?
    C5 H5 . 0.9300 ?
    C6 C8 . 1.390(3) ?
    C6 C7 . 1.475(3) ?
    C7 H7 . 0.9300 ?
    C9 C10 . 1.493(3) ?
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C10 H10A . 0.9700 ?
    C10 H10B . 0.9700 ?
    C11 C16 . 1.396(2) ?
    C11 C12 . 1.409(2) ?
    C12 C13 . 1.375(3) ?
    C13 C14 . 1.370(3) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.376(3) ?
    C15 C16 . 1.368(3) ?
    C15 H15 . 0.9300 ?
    C16 H16 . 0.9300 ?
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
    C2 O1 C1 . . 117.46(16) ?
    C8 O3 C9 . . 113.02(14) ?
    C11 O4 C10 . . 118.44(14) ?
    O5 N1 O6 . . 122.31(18) ?
    O5 N1 C12 . . 119.61(17) ?
    O6 N1 C12 . . 118.01(17) ?
    O8 N2 O7 . . 124.25(18) ?
    O8 N2 C14 . . 118.00(19) ?
    O7 N2 C14 . . 117.75(18) ?
    O1 C1 H1A . . 109.5 ?
    O1 C1 H1B . . 109.5 ?
    H1A C1 H1B . . 109.5 ?
    O1 C1 H1C . . 109.5 ?
    H1A C1 H1C . . 109.5 ?
    H1B C1 H1C . . 109.5 ?
    O1 C2 C3 . . 125.52(18) ?
    O1 C2 C8 . . 115.04(16) ?
    C3 C2 C8 . . 119.43(18) ?
    C2 C3 C4 . . 120.05(19) ?
    C2 C3 H3 . . 120.0 ?
    C4 C3 H3 . . 120.0 ?
    C5 C4 C3 . . 120.9(2) ?
    C5 C4 H4 . . 119.6 ?
    C3 C4 H4 . . 119.6 ?
    C4 C5 C6 . . 120.06(19) ?
    C4 C5 H5 . . 120.0 ?
    C6 C5 H5 . . 120.0 ?
    C8 C6 C5 . . 119.46(18) ?
    C8 C6 C7 . . 120.16(19) ?
    C5 C6 C7 . . 120.36(19) ?
    O2 C7 C6 . . 124.8(2) ?
    O2 C7 H7 . . 117.6 ?
    C6 C7 H7 . . 117.6 ?
    O3 C8 C6 . . 120.22(17) ?
    O3 C8 C2 . . 119.65(16) ?
    C6 C8 C2 . . 120.09(17) ?
    O3 C9 C10 . . 108.52(16) ?
    O3 C9 H9A . . 110.0 ?
    C10 C9 H9A . . 110.0 ?
    O3 C9 H9B . . 110.0 ?
    C10 C9 H9B . . 110.0 ?
    H9A C9 H9B . . 108.4 ?
    O4 C10 C9 . . 106.84(15) ?
    O4 C10 H10A . . 110.4 ?
    C9 C10 H10A . . 110.4 ?
    O4 C10 H10B . . 110.4 ?
    C9 C10 H10B . . 110.4 ?
    H10A C10 H10B . . 108.6 ?
    O4 C11 C16 . . 123.97(17) ?
    O4 C11 C12 . . 118.84(16) ?
    C16 C11 C12 . . 117.14(17) ?
    C13 C12 C11 . . 121.27(16) ?
    C13 C12 N1 . . 116.33(16) ?
    C11 C12 N1 . . 122.37(16) ?
    C14 C13 C12 . . 119.09(17) ?
    C14 C13 H13 . . 120.5 ?
    C12 C13 H13 . . 120.5 ?
    C13 C14 C15 . . 121.56(18) ?
    C13 C14 N2 . . 118.55(18) ?
    C15 C14 N2 . . 119.86(18) ?
    C16 C15 C14 . . 119.19(18) ?
    C16 C15 H15 . . 120.4 ?
    C14 C15 H15 . . 120.4 ?
    C15 C16 C11 . . 121.67(18) ?
    C15 C16 H16 . . 119.2 ?
    C11 C16 H16 . . 119.2 ?
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
    C1 O1 C2 C3 . . . . -2.1(3) ?
    C1 O1 C2 C8 . . . . 176.82(18) ?
    O1 C2 C3 C4 . . . . 179.23(18) ?
    C8 C2 C3 C4 . . . . 0.4(3) ?
    C2 C3 C4 C5 . . . . -0.3(3) ?
    C3 C4 C5 C6 . . . . -0.7(3) ?
    C4 C5 C6 C8 . . . . 1.5(3) ?
    C4 C5 C6 C7 . . . . -176.54(18) ?
    C8 C6 C7 O2 . . . . -175.8(2) ?
    C5 C6 C7 O2 . . . . 2.2(3) ?
    C9 O3 C8 C6 . . . . -98.76(19) ?
    C9 O3 C8 C2 . . . . 83.6(2) ?
    C5 C6 C8 O3 . . . . -179.09(16) ?
    C7 C6 C8 O3 . . . . -1.0(3) ?
    C5 C6 C8 C2 . . . . -1.4(3) ?
    C7 C6 C8 C2 . . . . 176.65(17) ?
    O1 C2 C8 O3 . . . . -0.8(2) ?
    C3 C2 C8 O3 . . . . 178.16(16) ?
    O1 C2 C8 C6 . . . . -178.49(16) ?
    C3 C2 C8 C6 . . . . 0.5(3) ?
    C8 O3 C9 C10 . . . . 176.44(16) ?
    C11 O4 C10 C9 . . . . -172.07(17) ?
    O3 C9 C10 O4 . . . . -64.6(2) ?
    C10 O4 C11 C16 . . . . -1.0(3) ?
    C10 O4 C11 C12 . . . . 176.56(17) ?
    O4 C11 C12 C13 . . . . -174.57(17) ?
    C16 C11 C12 C13 . . . . 3.2(3) ?
    O4 C11 C12 N1 . . . . 7.3(3) ?
    C16 C11 C12 N1 . . . . -174.94(17) ?
    O5 N1 C12 C13 . . . . -159.4(2) ?
    O6 N1 C12 C13 . . . . 17.6(3) ?
    O5 N1 C12 C11 . . . . 18.8(3) ?
    O6 N1 C12 C11 . . . . -164.20(19) ?
    C11 C12 C13 C14 . . . . -2.6(3) ?
    N1 C12 C13 C14 . . . . 175.59(16) ?
    C12 C13 C14 C15 . . . . 0.1(3) ?
    C12 C13 C14 N2 . . . . -177.82(17) ?
    O8 N2 C14 C13 . . . . 171.53(19) ?
    O7 N2 C14 C13 . . . . -8.3(3) ?
    O8 N2 C14 C15 . . . . -6.5(3) ?
    O7 N2 C14 C15 . . . . 173.72(19) ?
    C13 C14 C15 C16 . . . . 1.7(3) ?
    N2 C14 C15 C16 . . . . 179.60(18) ?
    C14 C15 C16 C11 . . . . -1.0(3) ?
    O4 C11 C16 C15 . . . . 176.29(19) ?
    C12 C11 C16 C15 . . . . -1.3(3) ?
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
    C16 H16 O6 4_576 0.93 2.56 3.378(3) 147 yes
data_global
_journal_date_recd_electronic     2006-10-16
_journal_date_accepted     2006-10-31
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue     12
_journal_page_first     o5404
_journal_page_last     o5405
_journal_paper_category     EO
_journal_coeditor_code     AT2142
_publ_contact_author_name     'Chun-Hua Diao'
_publ_contact_author_address
;
'College of Sciences
Tianjin University of Science and Technology
Tianjin 300222
P. R. China'
;
_publ_contact_author_email     diao_chunhua@163.com
_publ_contact_author_fax     '086(022)23001002'
_publ_contact_author_phone     '086(022)60270087'
_publ_section_title
;
2-[2-(2,4-Dinitrophenoxy)ethoxy]-3-methoxybenzaldehyde
;
loop_
    _publ_author_name
    _publ_author_address
    "Diao, Chun-Hua"
;
College of Sciences
Tianjin University of Science and Technology
Tianjin 300222
People's Republic of China
;
    "Yu, Ming"
;
College of Sciences
Tianjin University of Science and Technology
Tianjin 300222
People's Republic of China
;
