##############################################################################
###                                                                        ###
###        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 2.1.    #
#                                                                            #
# 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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data_global
_audit_creation_method     'SHELXL-97'
_journal_date_recd_electronic     2007-10-31
_journal_date_accepted     2007-11-21
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      1
_journal_page_first     o71
_journal_page_last     o71
_journal_paper_category     QO
_journal_coeditor_code     RZ2178
_publ_contact_author_name     'Dr. Qian-Jun ZHANG'
_publ_contact_author_address
;
Institute of Applied Chemistry
Guizhou University
Guiyang, 550025,
People's Republic of China
;
_publ_contact_author_email     qianjunzhang@126.com
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
5,7-Dihydroxy-6,4'-dimethoxyflavone
;
loop_
    _publ_author_name
    _publ_author_address
    'Ming-Yue Mou'
;
Research and Development Center of Fine Chemicals of Guizhou University,
Guiyang 550025,
People's Republic of China
;
    'Ke Pi'
;
Research and Development Center of Fine Chemicals of Guizhou University,
Guiyang 550025,
People's Republic of China
;
    'Qi-Long Zhang'
;
Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province,
Guizhou University,
Guiyang 550025,
People's Republic of China
;
    'Yun-Qian Zhang'
;
Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province,
Guizhou University,
Guiyang 550025,
People's Republic of China
;
    'Qian-Jun Zhang'
;
Science College of Guizhou University,
Guiyang 550025,
People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
5,7-Dihydroxy-6,4'-dimethoxyflavone
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H14 O6'
_chemical_formula_sum     'C17 H14 O6'
_chemical_formula_iupac     'C17 H14 O6'
_chemical_formula_weight     314.28
_chemical_melting_point     '224-226\% C'
_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     6.9115(11)
_cell_length_b     7.2583(12)
_cell_length_c     14.649(2)
_cell_angle_alpha     82.739(6)
_cell_angle_beta     88.424(6)
_cell_angle_gamma     76.907(6)
_cell_volume     710.0(2)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     7597
_cell_measurement_theta_min     1.40
_cell_measurement_theta_max     25.00
_cell_measurement_temperature     293(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.18
_exptl_crystal_size_mid     0.12
_exptl_crystal_size_min     0.09
_exptl_crystal_density_diffrn     1.470
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     328
_exptl_absorpt_coefficient_mu     0.112
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     'SADABS (Bruker, 2005)'
_exptl_absorpt_correction_T_min     0.980
_exptl_absorpt_correction_T_max     0.990
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     293(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 APEXII CCD area-detector'
_diffrn_measurement_method     'φ and ω scan'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     7597
_diffrn_reflns_av_R_equivalents     0.0202
_diffrn_reflns_av_sigmaI/netI     0.0218
_diffrn_reflns_theta_min     1.40
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.987
_diffrn_measured_fraction_theta_full     0.987
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_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 > 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     2469
_reflns_number_gt     2095
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0446
_refine_ls_R_factor_gt     0.0379
_refine_ls_wR_factor_gt     0.1051
_refine_ls_wR_factor_ref     0.1102
_refine_ls_goodness_of_fit_ref     1.075
_refine_ls_restrained_S_all     1.075
_refine_ls_number_reflns     2469
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0576P)²+0.1294P] 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     0.199
_refine_diff_density_min     -0.186
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef     0.036(5)
_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'
    '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, 2005)'
_computing_cell_refinement     'SAINT (Bruker, 2005)'
_computing_data_reduction     'SAINT (Bruker, 2005)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material     'WinGX (Farrugia, 1999)'
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
    C C1 -0.3004(3) 0.9240(3) 0.86019(11) 0.0675(5) Uani d . 1 . .
    H H1A -0.3983 0.9715 0.9043 0.101 Uiso calc R 1 . .
    H H1B -0.1984 0.9951 0.8563 0.101 Uiso calc R 1 . .
    H H1C -0.2428 0.7918 0.8791 0.101 Uiso calc R 1 . .
    C C2 -0.2756(2) 0.8843(2) 0.70068(10) 0.0444(4) Uani d . 1 . .
    C C3 -0.0702(2) 0.8314(2) 0.70196(10) 0.0476(4) Uani d . 1 . .
    H H3 -0.0005 0.8308 0.7555 0.057 Uiso calc R 1 . .
    C C4 0.0309(2) 0.7793(2) 0.62275(10) 0.0441(4) Uani d . 1 . .
    H H4 0.1689 0.7443 0.6237 0.053 Uiso calc R 1 . .
    C C5 -0.0691(2) 0.77829(18) 0.54212(9) 0.0361(3) Uani d . 1 . .
    C C6 -0.2764(2) 0.8273(2) 0.54371(10) 0.0443(4) Uani d . 1 . .
    H H6 -0.3473 0.8244 0.4911 0.053 Uiso calc R 1 . .
    C C7 -0.3773(2) 0.8797(2) 0.62189(11) 0.0494(4) Uani d . 1 . .
    H H7 -0.5154 0.9123 0.6215 0.059 Uiso calc R 1 . .
    C C8 0.0387(2) 0.72640(18) 0.45786(9) 0.0353(3) Uani d . 1 . .
    C C9 0.2359(2) 0.6569(2) 0.44969(10) 0.0416(4) Uani d . 1 . .
    H H9 0.3163 0.6392 0.5014 0.050 Uiso calc R 1 . .
    C C10 0.3248(2) 0.6095(2) 0.36394(10) 0.0398(3) Uani d . 1 . .
    C C11 0.18831(19) 0.63688(18) 0.28746(9) 0.0351(3) Uani d . 1 . .
    C C12 -0.0140(2) 0.71097(19) 0.30008(9) 0.0349(3) Uani d . 1 . .
    C C13 -0.1511(2) 0.7425(2) 0.22975(10) 0.0412(4) Uani d . 1 . .
    H H13 -0.2849 0.7941 0.2395 0.049 Uiso calc R 1 . .
    C C14 -0.0826(2) 0.6948(2) 0.14458(10) 0.0400(4) Uani d . 1 . .
    C C15 0.1185(2) 0.6180(2) 0.12867(9) 0.0392(4) Uani d . 1 . .
    C C16 0.2539(2) 0.5884(2) 0.19985(10) 0.0381(3) Uani d . 1 . .
    C C17 0.2732(3) 0.7014(3) -0.01218(11) 0.0595(5) Uani d . 1 . .
    H H17A 0.3096 0.6582 -0.0709 0.089 Uiso calc R 1 . .
    H H17B 0.3904 0.7090 0.0195 0.089 Uiso calc R 1 . .
    H H17C 0.1849 0.8250 -0.0211 0.089 Uiso calc R 1 . .
    O O1 -0.39076(18) 0.94398(18) 0.77344(8) 0.0630(4) Uani d . 1 . .
    O O2 0.50778(15) 0.54639(17) 0.35414(7) 0.0547(3) Uani d . 1 . .
    O O3 0.44741(15) 0.51494(17) 0.18454(7) 0.0531(3) Uani d . 1 . .
    H H3A 0.5105 0.5051 0.2322 0.080 Uiso calc R 1 . .
    O O4 0.17552(15) 0.56933(15) 0.04163(7) 0.0475(3) Uani d . 1 . .
    O O5 -0.21639(15) 0.72526(17) 0.07437(7) 0.0550(3) Uani d . 1 . .
    H H5 -0.1587 0.6919 0.0275 0.083 Uiso calc R 1 . .
    O O6 -0.08666(13) 0.75600(14) 0.38456(6) 0.0384(3) Uani d . 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
    C1 O1 . 1.408(2) ?
    C1 H1A . 0.9600 ?
    C1 H1B . 0.9600 ?
    C1 H1C . 0.9600 ?
    C2 O1 . 1.3678(18) ?
    C2 C7 . 1.376(2) ?
    C2 C3 . 1.384(2) ?
    C3 C4 . 1.387(2) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.387(2) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.396(2) ?
    C5 C8 . 1.470(2) ?
    C6 C7 . 1.374(2) ?
    C6 H6 . 0.9300 ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.349(2) ?
    C8 O6 . 1.3632(16) ?
    C9 C10 . 1.430(2) ?
    C9 H9 . 0.9300 ?
    C10 O2 . 1.2545(17) ?
    C10 C11 . 1.4498(19) ?
    C11 C12 . 1.3959(19) ?
    C11 C16 . 1.409(2) ?
    C12 O6 . 1.3727(16) ?
    C12 C13 . 1.3812(19) ?
    C13 C14 . 1.379(2) ?
    C13 H13 . 0.9300 ?
    C14 O5 . 1.3651(17) ?
    C14 C15 . 1.400(2) ?
    C15 C16 . 1.384(2) ?
    C15 O4 . 1.3890(16) ?
    C16 O3 . 1.3471(17) ?
    C17 O4 . 1.4383(19) ?
    C17 H17A . 0.9600 ?
    C17 H17B . 0.9600 ?
    C17 H17C . 0.9600 ?
    O3 H3A . 0.8200 ?
    O5 H5 . 0.8200 ?
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
    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 C7 . . 115.54(14) ?
    O1 C2 C3 . . 124.67(14) ?
    C7 C2 C3 . . 119.78(14) ?
    C2 C3 C4 . . 119.42(14) ?
    C2 C3 H3 . . 120.3 ?
    C4 C3 H3 . . 120.3 ?
    C5 C4 C3 . . 121.51(14) ?
    C5 C4 H4 . . 119.2 ?
    C3 C4 H4 . . 119.2 ?
    C4 C5 C6 . . 117.71(13) ?
    C4 C5 C8 . . 121.32(13) ?
    C6 C5 C8 . . 120.97(12) ?
    C7 C6 C5 . . 121.01(14) ?
    C7 C6 H6 . . 119.5 ?
    C5 C6 H6 . . 119.5 ?
    C6 C7 C2 . . 120.53(15) ?
    C6 C7 H7 . . 119.7 ?
    C2 C7 H7 . . 119.7 ?
    C9 C8 O6 . . 121.73(13) ?
    C9 C8 C5 . . 126.79(13) ?
    O6 C8 C5 . . 111.48(11) ?
    C8 C9 C10 . . 121.96(13) ?
    C8 C9 H9 . . 119.0 ?
    C10 C9 H9 . . 119.0 ?
    O2 C10 C9 . . 123.33(13) ?
    O2 C10 C11 . . 121.21(13) ?
    C9 C10 C11 . . 115.46(12) ?
    C12 C11 C16 . . 118.45(12) ?
    C12 C11 C10 . . 119.87(12) ?
    C16 C11 C10 . . 121.68(13) ?
    O6 C12 C13 . . 116.48(12) ?
    O6 C12 C11 . . 120.89(12) ?
    C13 C12 C11 . . 122.63(13) ?
    C14 C13 C12 . . 117.67(13) ?
    C14 C13 H13 . . 121.2 ?
    C12 C13 H13 . . 121.2 ?
    O5 C14 C13 . . 118.33(13) ?
    O5 C14 C15 . . 119.79(13) ?
    C13 C14 C15 . . 121.87(13) ?
    C16 C15 O4 . . 121.77(13) ?
    C16 C15 C14 . . 119.65(13) ?
    O4 C15 C14 . . 118.56(12) ?
    O3 C16 C15 . . 119.67(13) ?
    O3 C16 C11 . . 120.61(13) ?
    C15 C16 C11 . . 119.71(13) ?
    O4 C17 H17A . . 109.5 ?
    O4 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    O4 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
    C2 O1 C1 . . 118.62(14) ?
    C16 O3 H3A . . 109.5 ?
    C15 O4 C17 . . 114.00(11) ?
    C14 O5 H5 . . 109.5 ?
    C8 O6 C12 . . 120.07(11) ?
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 C2 C3 C4 . . . . -177.85(14) ?
    C7 C2 C3 C4 . . . . 1.7(2) ?
    C2 C3 C4 C5 . . . . -0.2(2) ?
    C3 C4 C5 C6 . . . . -1.5(2) ?
    C3 C4 C5 C8 . . . . 178.85(13) ?
    C4 C5 C6 C7 . . . . 1.7(2) ?
    C8 C5 C6 C7 . . . . -178.62(13) ?
    C5 C6 C7 C2 . . . . -0.2(2) ?
    O1 C2 C7 C6 . . . . 178.11(14) ?
    C3 C2 C7 C6 . . . . -1.5(2) ?
    C4 C5 C8 C9 . . . . 7.4(2) ?
    C6 C5 C8 C9 . . . . -172.29(14) ?
    C4 C5 C8 O6 . . . . -172.95(12) ?
    C6 C5 C8 O6 . . . . 7.41(19) ?
    O6 C8 C9 C10 . . . . -0.2(2) ?
    C5 C8 C9 C10 . . . . 179.42(13) ?
    C8 C9 C10 O2 . . . . 179.30(14) ?
    C8 C9 C10 C11 . . . . -1.5(2) ?
    O2 C10 C11 C12 . . . . -178.72(13) ?
    C9 C10 C11 C12 . . . . 2.0(2) ?
    O2 C10 C11 C16 . . . . 2.0(2) ?
    C9 C10 C11 C16 . . . . -177.22(12) ?
    C16 C11 C12 O6 . . . . 178.30(12) ?
    C10 C11 C12 O6 . . . . -1.0(2) ?
    C16 C11 C12 C13 . . . . -1.5(2) ?
    C10 C11 C12 C13 . . . . 179.21(13) ?
    O6 C12 C13 C14 . . . . -178.69(12) ?
    C11 C12 C13 C14 . . . . 1.1(2) ?
    C12 C13 C14 O5 . . . . -179.95(12) ?
    C12 C13 C14 C15 . . . . -0.4(2) ?
    O5 C14 C15 C16 . . . . 179.62(13) ?
    C13 C14 C15 C16 . . . . 0.1(2) ?
    O5 C14 C15 O4 . . . . -1.9(2) ?
    C13 C14 C15 O4 . . . . 178.50(13) ?
    O4 C15 C16 O3 . . . . 1.8(2) ?
    C14 C15 C16 O3 . . . . -179.86(13) ?
    O4 C15 C16 C11 . . . . -178.83(12) ?
    C14 C15 C16 C11 . . . . -0.4(2) ?
    C12 C11 C16 O3 . . . . -179.45(12) ?
    C10 C11 C16 O3 . . . . -0.2(2) ?
    C12 C11 C16 C15 . . . . 1.1(2) ?
    C10 C11 C16 C15 . . . . -179.60(12) ?
    C7 C2 O1 C1 . . . . 170.14(15) ?
    C3 C2 O1 C1 . . . . -10.3(2) ?
    C16 C15 O4 C17 . . . . -77.04(18) ?
    C14 C15 O4 C17 . . . . 104.56(16) ?
    C9 C8 O6 C12 . . . . 1.4(2) ?
    C5 C8 O6 C12 . . . . -178.27(11) ?
    C13 C12 O6 C8 . . . . 179.03(12) ?
    C11 C12 O6 C8 . . . . -0.80(19) ?
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
    O3 H3A O2 . 0.82 1.85 2.5774(15) 147.6
    O5 H5 O4 . 0.82 2.28 2.7431(15) 115.9
    O5 H5 O4 2_565 0.82 2.29 2.8562(15) 127.0
    C1 H1B Cg3 2_578 0.96 2.93 3.799(2) 150
