##############################################################################
###                                                                        ###
###        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     2002-01-28
_journal_date_accepted     2002-02-07
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2002
_journal_volume     58
_journal_issue      3
_journal_page_first     o285
_journal_page_last     o287
_journal_paper_category     EO
_publ_contact_author
;
    Masood Parvez
    Department of Chemistry
    University of Calgary
    2500 University Drive NW
    Calgary, Alberta, Canada T2N 1N4
;
_publ_contact_author_email     parvez@ucalgary.ca
_publ_contact_author_fax     ' (403)289-9488 '
_publ_contact_author_phone     ' (403)220-5348 '
_publ_section_title
;
Cirsimaritin
;
loop_
    _publ_author_name
    _publ_author_address
    'Chou, Nancy Hieu-Hong'
; Department of Chemistry
The University of Calgary
2500 University Drive NW
Calgary
Alberta
Canada T2N 1N4
;
    'Parvez, Masood'
; Department of Chemistry
The University of Calgary
2500 University Drive NW
Calgary
Alberta
Canada T2N 1N4
;
    'Ali, Muhammad Shaiq'
; HEJ Research Institute of Chemistry
University of Karachi
Karachi 75270
Pakistan
;
    'Ahmed, Shakeel'
; HEJ Research Institute of Chemistry
University of Karachi
Karachi 75270
Pakistan
;
    'Ahmed, Waqar'
; HEJ Research Institute of Chemistry
University of Karachi
Karachi 75270
Pakistan
;
data_I
_chemical_name_systematic     " (5,4'-Dihydroxy-6,7-dimethoxyflavone) "
_chemical_name_common     'Cirsimaritin'
_chemical_formula_moiety     'C17 H14 O6'
_chemical_formula_sum     'C17 H14 O6'
_chemical_formula_iupac     'C17 H14 O6'
_chemical_formula_weight     314.28
_symmetry_cell_setting     Orthorhombic
_symmetry_space_group_name_H-M     'P b c a'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, y, -z-1/2'
    '-x-1/2, y-1/2, z'
    'x, -y-1/2, z-1/2'
_cell_length_a     8.3669(2)
_cell_length_b     13.5769(4)
_cell_length_c     25.2554(9)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     2868.93(15)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     3674
_cell_measurement_theta_min     1.0
_cell_measurement_theta_max     30.0
_cell_measurement_temperature     293(2)
_exptl_crystal_description     'prismatic'
_exptl_crystal_colour     'yellow'
_exptl_crystal_size_max      .25
_exptl_crystal_size_mid      .25
_exptl_crystal_size_min      .13
_exptl_crystal_density_diffrn     1.455
_exptl_crystal_density_meas     'not measured'
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1312
_exptl_absorpt_coefficient_mu      .11
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SORTAV: Blessing, 1995, 1997)'
_exptl_absorpt_correction_T_min      .973
_exptl_absorpt_correction_T_max      .986
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength      .71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Nonius KappaCCD'
_diffrn_measurement_method     ω-2φ
_diffrn_reflns_number     6714
_diffrn_reflns_av_R_equivalents      .036
_diffrn_reflns_av_sigmaI/netI      .059
_diffrn_reflns_theta_min     3.2
_diffrn_reflns_theta_max     30.0
_diffrn_reflns_theta_full     30.0
_diffrn_measured_fraction_theta_max      .944
_diffrn_measured_fraction_theta_full      .944
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -18
_diffrn_reflns_limit_k_max     18
_diffrn_reflns_limit_l_min     -35
_diffrn_reflns_limit_l_max     35
_diffrn_standards_decay_%     <0.1
_reflns_number_total     3958
_reflns_number_gt     2594
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all      .086
_refine_ls_R_factor_gt      .048
_refine_ls_wR_factor_gt      .134
_refine_ls_wR_factor_ref      .157
_refine_ls_goodness_of_fit_ref      .98
_refine_ls_restrained_S_all      .98
_refine_ls_number_reflns     3958
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.092P)²+0.124P] 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      .00
_refine_diff_density_max      .22
_refine_diff_density_min      -.19
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef      .004(4)
_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'  .0033  .0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H'  .0000  .0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O'  .0106  .0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'COLLECT (Hooft, 1998)'
_computing_cell_refinement     'HKL DENZO (Otwinowski & Minor, 1997)'
_computing_data_reduction     'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SAPI91 (Fan, 1991)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
                                'TEXSAN (Molecular Structure Corporation, 1994)'
_computing_publication_material     'SHELXL97 (Sheldrick, 1997)'
loop_
    _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
    _atom_site_type_symbol
    O1  .80664(14)  .24686(7)  .80247(4)  .0381(3) Uani d . 1 . . O
    O2 1.02299(16)  .51658(8)  .80368(5)  .0536(4) Uani d . 1 . . O
    O3  .99288(17)  .52501(8)  .70219(5)  .0516(3) Uani d . 1 . . O
    H3 1.0179  .5432  .7320  .077 Uiso calc R 1 . . H
    O4  .88775(12)  .43326(7)  .61005(4)  .0371(3) Uani d . 1 . . O
    O5  .77847(13)  .25240(7)  .61361(4)  .0387(3) Uani d . 1 . . O
    C2  .84898(17)  .29054(11)  .84907(6)  .0349(3) Uani d . 1 . . C
    C3  .9234(2)  .37910(11)  .85047(6)  .0400(4) Uani d . 1 . . C
    H3A  .9534  .4052  .8830  .048 Uiso calc R 1 . . H
    C4  .95727(19)  .43342(11)  .80347(6)  .0382(4) Uani d . 1 . . C
    C5  .92861(18)  .43392(10)  .70475(6)  .0356(4) Uani d . 1 . . C
    C6  .88195(17)  .38706(10)  .65878(6)  .0336(3) Uani d . 1 . . C
    C7  .81601(16)  .29160(10)  .66133(6)  .0320(3) Uani d . 1 . . C
    C8  .79119(18)  .24486(11)  .70964(6)  .0339(3) Uani d . 1 . . C
    H8  .7458  .1824  .7113  .041 Uiso calc R 1 . . H
    C9  .83633(18)  .29435(10)  .75520(6)  .0331(3) Uani d . 1 . . C
    C10  .90838(18)  .38715(10)  .75431(6)  .0342(3) Uani d . 1 . . C
    C11 1.04456(19)  .45254(14)  .58946(8)  .0514(5) Uani d . 1 . . C
    H11A 1.0356  .4849  .5558  .077 Uiso calc R 1 . . H
    H11B 1.1010  .3915  .5852  .077 Uiso calc R 1 . . H
    H11C 1.1019  .4941  .6137  .077 Uiso calc R 1 . . H
    C12  .72652(19)  .15138(11)  .61253(6)  .0402(4) Uani d . 1 . . C
    H12A  .7038  .1324  .5767  .060 Uiso calc R 1 . . H
    H12B  .6318  .1444  .6336  .060 Uiso calc R 1 . . H
    H12C  .8093  .1100  .6265  .060 Uiso calc R 1 . . H
    O4'  .66934(13)  .07247(9) 1.02896(4)  .0458(3) Uani d . 1 . . O
    H4'  .7316  .0822 1.0535  .069 Uiso calc R 1 . . H
    C1'  .80245(17)  .23266(11)  .89568(6)  .0342(3) Uani d . 1 . . C
    C2'  .87905(19)  .24867(12)  .94417(6)  .0406(4) Uani d . 1 . . C
    H2'  .9605  .2951  .9463  .049 Uiso calc R 1 . . H
    C3'  .83574(18)  .19664(12)  .98898(6)  .0414(4) Uani d . 1 . . C
    H3'  .8881  .2081 1.0209  .050 Uiso calc R 1 . . H
    C4'  .71426(17)  .12738(10)  .98637(6)  .0343(3) Uani d . 1 . . C
    C5'  .63504(17)  .11167(12)  .93868(6)  .0379(4) Uani d . 1 . . C
    H5'  .5518  .0664  .9370  .045 Uiso calc R 1 . . H
    C6'  .67942(17)  .16312(11)  .89360(6)  .0370(4) Uani d . 1 . . C
    H6'  .6270  .1513  .8618  .044 Uiso calc R 1 . . H
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 . 1.3645(16) y
    O1 C9 . 1.3794(16) y
    O2 C4 . 1.2559(19) y
    O3 C5 . 1.3502(17) y
    O3 H3 .  .8200 n
    O4 C6 . 1.3821(17) y
    O4 C11 . 1.4353(19) y
    O5 C7 . 1.3544(16) y
    O5 C12 . 1.4390(17) y
    C2 C3 . 1.355(2) n
    C2 C1' . 1.468(2) n
    C3 C4 . 1.426(2) n
    C3 H3A .  .9300 n
    C4 C10 . 1.450(2) n
    C5 C6 . 1.380(2) n
    C5 C10 . 1.414(2) n
    C6 C7 . 1.410(2) n
    C7 C8 . 1.3908(19) n
    C8 C9 . 1.3850(19) n
    C8 H8 .  .9300 n
    C9 C10 . 1.397(2) n
    C11 H11A .  .9600 n
    C11 H11B .  .9600 n
    C11 H11C .  .9600 n
    C12 H12A .  .9600 n
    C12 H12B .  .9600 n
    C12 H12C .  .9600 n
    O4' C4' . 1.3617(17) y
    O4' H4' .  .8200 n
    C1' C6' . 1.398(2) n
    C1' C2' . 1.399(2) n
    C2' C3' . 1.383(2) n
    C2' H2' .  .9300 n
    C3' C4' . 1.386(2) n
    C3' H3' .  .9300 n
    C4' C5' . 1.391(2) n
    C5' C6' . 1.386(2) n
    C5' H5' .  .9300 n
    C6' H6' .  .9300 n
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 C9 . . 119.77(11) y
    C5 O3 H3 . . 109.5 n
    C6 O4 C11 . . 115.94(12) y
    C7 O5 C12 . . 117.49(12) y
    C3 C2 O1 . . 121.85(13) n
    C3 C2 C1' . . 125.18(14) n
    O1 C2 C1' . . 112.96(13) n
    C2 C3 C4 . . 121.91(14) n
    C2 C3 H3A . . 119.0 n
    C4 C3 H3A . . 119.0 n
    O2 C4 C3 . . 123.25(14) n
    O2 C4 C10 . . 121.10(14) n
    C3 C4 C10 . . 115.64(13) n
    O3 C5 C6 . . 119.64(13) n
    O3 C5 C10 . . 120.09(13) n
    C6 C5 C10 . . 120.26(13) n
    C5 C6 O4 . . 122.00(12) n
    C5 C6 C7 . . 119.72(13) n
    O4 C6 C7 . . 118.14(12) n
    O5 C7 C8 . . 124.52(13) n
    O5 C7 C6 . . 114.28(12) n
    C8 C7 C6 . . 121.19(13) n
    C9 C8 C7 . . 117.83(13) n
    C9 C8 H8 . . 121.1 n
    C7 C8 H8 . . 121.1 n
    O1 C9 C8 . . 116.31(12) n
    O1 C9 C10 . . 120.88(12) n
    C8 C9 C10 . . 122.81(13) n
    C9 C10 C5 . . 118.10(13) n
    C9 C10 C4 . . 119.91(13) n
    C5 C10 C4 . . 121.99(13) n
    O4 C11 H11A . . 109.5 n
    O4 C11 H11B . . 109.5 n
    H11A C11 H11B . . 109.5 n
    O4 C11 H11C . . 109.5 n
    H11A C11 H11C . . 109.5 n
    H11B C11 H11C . . 109.5 n
    O5 C12 H12A . . 109.5 n
    O5 C12 H12B . . 109.5 n
    H12A C12 H12B . . 109.5 n
    O5 C12 H12C . . 109.5 n
    H12A C12 H12C . . 109.5 n
    H12B C12 H12C . . 109.5 n
    C4' O4' H4' . . 109.5 n
    C6' C1' C2' . . 118.38(14) n
    C6' C1' C2 . . 121.78(14) n
    C2' C1' C2 . . 119.82(14) n
    C3' C2' C1' . . 121.13(14) n
    C3' C2' H2' . . 119.4 n
    C1' C2' H2' . . 119.4 n
    C2' C3' C4' . . 119.98(14) n
    C2' C3' H3' . . 120.0 n
    C4' C3' H3' . . 120.0 n
    O4' C4' C3' . . 122.42(14) n
    O4' C4' C5' . . 117.93(13) n
    C3' C4' C5' . . 119.65(14) n
    C6' C5' C4' . . 120.40(14) n
    C6' C5' H5' . . 119.8 n
    C4' C5' H5' . . 119.8 n
    C5' C6' C1' . . 120.44(14) n
    C5' C6' H6' . . 119.8 n
    C1' C6' H6' . . 119.8 n
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
    C9 O1 C2 C3 . . . . -1.6(2) n
    C9 O1 C2 C1' . . . . 177.30(11) n
    O1 C2 C3 C4 . . . . 2.1(2) n
    C1' C2 C3 C4 . . . . -176.59(14) n
    C2 C3 C4 O2 . . . . 178.40(16) n
    C2 C3 C4 C10 . . . .  -.7(2) n
    O3 C5 C6 O4 . . . . -4.9(2) n
    C10 C5 C6 O4 . . . . 174.69(13) n
    O3 C5 C6 C7 . . . . 179.48(14) n
    C10 C5 C6 C7 . . . .  -.9(2) n
    C11 O4 C6 C5 . . . . 69.29(19) n
    C11 O4 C6 C7 . . . . -115.04(15) n
    C12 O5 C7 C8 . . . . -7.4(2) n
    C12 O5 C7 C6 . . . . 173.57(13) n
    C5 C6 C7 O5 . . . . -178.47(13) n
    O4 C6 C7 O5 . . . . 5.75(19) n
    C5 C6 C7 C8 . . . . 2.5(2) n
    O4 C6 C7 C8 . . . . -173.27(13) n
    O5 C7 C8 C9 . . . . 179.81(13) n
    C6 C7 C8 C9 . . . . -1.3(2) n
    C2 O1 C9 C8 . . . . 179.43(12) n
    C2 O1 C9 C10 . . . .  -.5(2) n
    C7 C8 C9 O1 . . . . 178.54(12) n
    C7 C8 C9 C10 . . . . -1.6(2) n
    O1 C9 C10 C5 . . . . -177.04(13) n
    C8 C9 C10 C5 . . . . 3.1(2) n
    O1 C9 C10 C4 . . . . 1.8(2) n
    C8 C9 C10 C4 . . . . -178.03(14) n
    O3 C5 C10 C9 . . . . 177.83(14) n
    C6 C5 C10 C9 . . . . -1.8(2) n
    O3 C5 C10 C4 . . . . -1.0(2) n
    C6 C5 C10 C4 . . . . 179.37(13) n
    O2 C4 C10 C9 . . . . 179.64(15) n
    C3 C4 C10 C9 . . . . -1.3(2) n
    O2 C4 C10 C5 . . . . -1.5(2) n
    C3 C4 C10 C5 . . . . 177.57(13) n
    C3 C2 C1' C6' . . . . 156.21(16) n
    O1 C2 C1' C6' . . . . -22.6(2) n
    C3 C2 C1' C2' . . . . -21.9(2) n
    O1 C2 C1' C2' . . . . 159.30(13) n
    C6' C1' C2' C3' . . . .  .6(2) n
    C2 C1' C2' C3' . . . . 178.76(14) n
    C1' C2' C3' C4' . . . .  -.2(2) n
    C2' C3' C4' O4' . . . . 178.44(14) n
    C2' C3' C4' C5' . . . .  -.9(2) n
    O4' C4' C5' C6' . . . . -177.83(13) n
    C3' C4' C5' C6' . . . . 1.5(2) n
    C4' C5' C6' C1' . . . . -1.1(2) n
    C2' C1' C6' C5' . . . .  .1(2) n
    C2 C1' C6' C5' . . . . -178.08(13) n
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
    O4' H4' O4 8_566  .82 1.95 2.7459(15) 164
    O3 H3 O2 .  .82 1.85 2.5780(16) 148
