#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/02/2210255.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2210255
loop_
_publ_author_name
'Asker, Erol'
'Akin, Sebahat'
'Hökelek, Tuncer'
_publ_section_title
;
 5,3'-Dihydroxy-3,6,7,4'-tetramethoxyflavone
;
_journal_coeditor_code           HB2123
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4159
_journal_page_last               o4161
_journal_paper_doi               10.1107/S1600536806033630
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C19 H18 O8'
_chemical_formula_moiety         'C19 H18 O8'
_chemical_formula_sum            'C19 H18 O8'
_chemical_formula_weight         374.33
_chemical_name_common
;
5,3'-Dihydroxy-3,6,7,4'-tetramethoxyflavone
;
_chemical_name_systematic
;
5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,6,7-trimethoxychromen-4-one
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.424(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.5353(5)
_cell_length_b                   12.4493(3)
_cell_length_c                   17.6655(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      19.3
_cell_measurement_theta_min      2.15
_cell_volume                     3413.51(15)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1993)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            3463
_diffrn_reflns_theta_full        74.27
_diffrn_reflns_theta_max         74.27
_diffrn_reflns_theta_min         5.01
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.973
_exptl_absorpt_correction_T_max  0.868
_exptl_absorpt_correction_T_min  0.727
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.983
_refine_diff_density_min         -0.709
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3350
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.1267
_refine_ls_R_factor_gt           0.0940
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1338P)²+0.0496P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1891
_refine_ls_wR_factor_ref         0.2155
_reflns_number_gt                2259
_reflns_number_total             3350
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2123.cif
_cod_data_source_block           I
_cod_database_code               2210255
_cod_database_fobs_code          2210255
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
O O1 0.10368(12) 0.55315(14) 0.22741(11) 0.0539(5) Uani d . 1
O O3 0.19321(14) 0.61592(16) 0.41496(10) 0.0579(5) Uani d . 1
O O3' 0.10645(19) 0.16953(18) 0.22228(12) 0.0892(9) Uani d . 1
H H3' 0.1179 0.1082 0.2363 0.134 Uiso calc R 1
O O4 0.17190(15) 0.81631(16) 0.35145(12) 0.0665(6) Uani d . 1
O O4' 0.18957(13) 0.09746(14) 0.34872(11) 0.0618(6) Uani d . 1
O O5 0.13000(15) 0.93629(15) 0.23552(12) 0.0653(6) Uani d . 1
H H5 0.1480 0.9219 0.2786 0.098 Uiso calc R 1
O O6 0.06947(13) 0.94623(15) 0.08816(11) 0.0594(5) Uani d . 1
O O7 0.01526(15) 0.76975(18) 0.01627(11) 0.0675(6) Uani d . 1
C C1' 0.15122(16) 0.4250(2) 0.31602(14) 0.0469(6) Uani d . 1
C C2 0.14133(17) 0.5402(2) 0.29794(15) 0.0481(6) Uani d . 1
C C2' 0.1221(2) 0.3481(2) 0.26378(16) 0.0562(7) Uani d . 1
H H2' 0.0931 0.3703 0.2194 0.067 Uiso calc R 1
C C3 0.16416(18) 0.6276(2) 0.34138(15) 0.0498(6) Uani d . 1
C C3' 0.1350(2) 0.2404(2) 0.27612(15) 0.0552(7) Uani d . 1
C C4 0.15238(18) 0.7355(2) 0.31235(14) 0.0512(7) Uani d . 1
C C4A 0.11771(18) 0.7439(2) 0.23618(15) 0.0491(6) Uani d . 1
C C4' 0.17743(18) 0.2058(2) 0.34243(15) 0.0507(6) Uani d . 1
C C5 0.10608(18) 0.8445(2) 0.19899(17) 0.0531(7) Uani d . 1
C C5' 0.2051(2) 0.2807(3) 0.39475(18) 0.0712(9) Uani d . 1
H H5' 0.2328 0.2581 0.4397 0.085 Uiso calc R 1
C C6 0.07368(18) 0.8500(2) 0.12555(17) 0.0524(7) Uani d . 1
C C6' 0.1926(2) 0.3893(2) 0.38205(18) 0.0689(9) Uani d . 1
H H6' 0.2123 0.4387 0.4183 0.083 Uiso calc R 1
C C7 0.04725(19) 0.7549(2) 0.08729(15) 0.0532(7) Uani d . 1
C C8 0.05691(18) 0.6554(2) 0.12288(16) 0.0533(7) Uani d . 1
H H8 0.0396 0.5924 0.0983 0.064 Uiso calc R 1
C C8A 0.09290(17) 0.65286(19) 0.19558(16) 0.0485(6) Uani d . 1
C C9 0.2811(2) 0.6472(3) 0.4300(2) 0.0712(9) Uani d . 1
H H9A 0.3186 0.5960 0.4077 0.107 Uiso calc R 1
H H9B 0.2929 0.6496 0.4838 0.107 Uiso calc R 1
H H9C 0.2905 0.7169 0.4087 0.107 Uiso calc R 1
C C10 -0.0086(2) 1.0028(2) 0.0993(2) 0.0684(9) Uani d . 1
H H10A -0.0566 0.9595 0.0820 0.103 Uiso calc R 1
H H10B -0.0086 1.0688 0.0712 0.103 Uiso calc R 1
H H10C -0.0132 1.0183 0.1522 0.103 Uiso calc R 1
C C11 -0.0158(2) 0.6789(3) -0.02594(19) 0.0759(10) Uani d . 1
H H11A 0.0297 0.6271 -0.0295 0.114 Uiso calc R 1
H H11B -0.0348 0.7013 -0.0759 0.114 Uiso calc R 1
H H11C -0.0631 0.6471 -0.0008 0.114 Uiso calc R 1
C C12 0.2265(2) 0.0586(3) 0.41885(19) 0.0689(9) Uani d . 1
H H12A 0.2820 0.0908 0.4282 0.103 Uiso calc R 1
H H12B 0.2326 -0.0181 0.4163 0.103 Uiso calc R 1
H H12C 0.1896 0.0768 0.4592 0.103 Uiso calc R 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C2 O1 C8A 121.5(2) n
C3 O3 C9 114.9(2) ?
C3' O3' H3' 109.5 ?
C4' O4' C12 117.0(2) ?
C5 O5 H5 109.5 ?
C6 O6 C10 113.0(2) ?
C7 O7 C11 118.9(2) ?
C6' C1' C2' 117.7(3) n
C6' C1' C2 122.4(3) ?
C2' C1' C2 119.8(2) ?
O1 C2 C3 120.6(2) n
O1 C2 C1' 110.5(2) ?
C3 C2 C1' 129.0(2) ?
C3' C2' C1' 121.7(3) n
C3' C2' H2' 119.2 ?
C1' C2' H2' 119.2 ?
O3 C3 C2 121.0(2) ?
O3 C3 C4 117.9(2) ?
C2 C3 C4 120.9(2) n
O3' C3' C2' 118.8(3) ?
O3' C3' C4' 121.2(3) ?
C2' C3' C4' 119.9(3) n
O4 C4 C4A 122.3(2) ?
O4 C4 C3 121.8(2) ?
C4A C4 C3 115.9(2) n
C8A C4A C5 117.0(2) n
C8A C4A C4 120.8(2) n
C5 C4A C4 122.2(2) ?
O4' C4' C5' 125.4(2) ?
O4' C4' C3' 115.7(2) ?
C5' C4' C3' 118.9(2) n
O5 C5 C6 119.3(2) ?
O5 C5 C4A 119.7(3) ?
C6 C5 C4A 121.0(2) n
C4' C5' C6' 121.2(3) n
C4' C5' H5' 119.4 ?
C6' C5' H5' 119.4 ?
O6 C6 C5 120.5(3) ?
O6 C6 C7 119.6(3) ?
C5 C6 C7 119.8(2) n
C1' C6' C5' 120.6(3) n
C1' C6' H6' 119.7 ?
C5' C6' H6' 119.7 ?
O7 C7 C8 124.9(3) ?
O7 C7 C6 114.8(2) ?
C8 C7 C6 120.3(2) n
C8A C8 C7 118.1(3) n
C8A C8 H8 120.9 ?
C7 C8 H8 120.9 ?
O1 C8A C8 116.1(2) ?
O1 C8A C4A 120.1(2) n
C8 C8A C4A 123.8(2) n
O3 C9 H9A 109.5 ?
O3 C9 H9B 109.5 ?
H9A C9 H9B 109.5 ?
O3 C9 H9C 109.5 ?
H9A C9 H9C 109.5 ?
H9B C9 H9C 109.5 ?
O6 C10 H10A 109.5 ?
O6 C10 H10B 109.5 ?
H10A C10 H10B 109.5 ?
O6 C10 H10C 109.5 ?
H10A C10 H10C 109.5 ?
H10B C10 H10C 109.5 ?
O7 C11 H11A 109.5 ?
O7 C11 H11B 109.5 ?
H11A C11 H11B 109.5 ?
O7 C11 H11C 109.5 ?
H11A C11 H11C 109.5 ?
H11B C11 H11C 109.5 ?
O4' C12 H12A 109.5 ?
O4' C12 H12B 109.5 ?
H12A C12 H12B 109.5 ?
O4' C12 H12C 109.5 ?
H12A C12 H12C 109.5 ?
H12B C12 H12C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 1.363(3) n
O1 C8A 1.370(3) n
O3 C3 1.365(3) ?
O3 C9 1.433(4) ?
O3' C3' 1.358(3) ?
O3' H3' 0.8200 ?
O4' C4' 1.366(3) ?
O4' C12 1.428(3) ?
O4 C4 1.250(3) ?
O5 C5 1.356(3) ?
O5 H5 0.8200 ?
O6 C6 1.368(3) ?
O6 C10 1.424(3) ?
O7 C7 1.343(3) ?
C1' C6' 1.382(4) n
C1' C2' 1.392(4) n
C1' C2 1.475(4) n
C2 C3 1.370(4) n
C2' C3' 1.372(4) n
C2' H2' 0.9300 ?
C4 C3 1.447(4) n
C4' C5' 1.369(4) n
C4' C3' 1.388(4) n
C4A C8A 1.387(4) n
C4A C5 1.423(3) n
C4A C4 1.432(4) n
C5 C6 1.373(4) n
C5' C6' 1.383(4) n
C5' H5' 0.9300 ?
C6' H6' 0.9300 ?
C7 C6 1.415(4) n
C8 C8A 1.379(4) n
C8 C7 1.395(4) n
C8 H8 0.9300 ?
C9 H9A 0.9600 ?
C9 H9B 0.9600 ?
C9 H9C 0.9600 ?
C10 H10A 0.9600 ?
C10 H10B 0.9600 ?
C10 H10C 0.9600 ?
C11 O7 1.427(4) ?
C11 H11A 0.9600 ?
C11 H11B 0.9600 ?
C11 H11C 0.9600 ?
C12 H12A 0.9600 ?
C12 H12B 0.9600 ?
C12 H12C 0.9600 ?
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
O5 H5 O4 . 0.82 1.87 2.596(3) 148 yes
O3' H3' O4' . 0.82 2.24 2.687(3) 115 yes
O3' H3' O5 1_545 0.82 2.15 2.935(3) 161 yes
O5 H5 O4' 1_565 0.82 2.58 2.954(3) 109 yes
C10 H10b O7 5_575 0.96 2.54 3.491(4) 173 yes
C12 H12b O4 1_545 0.96 2.52 3.339(4) 143 yes
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
_geom_torsion_publ_flag
C2 O1 C8A C8 177.7(2) ?
C2 O1 C8A C4A -2.3(4) ?
C8A O1 C2 C3 4.6(4) ?
C8A O1 C2 C1' -175.5(2) ?
C9 O3 C3 C2 114.7(3) yes
C9 O3 C3 C4 -69.7(3) ?
C12 O4' C4' C5' 6.6(4) yes
C12 O4' C4' C3' -174.9(3) ?
C10 O6 C6 C5 -88.3(3) yes
C10 O6 C6 C7 94.0(3) ?
C11 O7 C7 C8 3.4(5) yes
C11 O7 C7 C6 -177.9(3) ?
C2' C1' C6' C5' 0.7(5) ?
C2 C1' C6' C5' -176.1(3) ?
C6' C1' C2 O1 175.7(3) ?
C2' C1' C2 O1 -1.0(4) ?
C6' C1' C2 C3 -4.4(5) ?
C2' C1' C2 C3 178.9(3) ?
C6' C1' C2' C3' -1.2(5) ?
C2 C1' C2' C3' 175.7(3) ?
O1 C2 C3 O3 172.8(2) ?
C1' C2 C3 O3 -7.1(5) ?
O1 C2 C3 C4 -2.7(4) ?
C1' C2 C3 C4 177.4(3) ?
C1' C2' C3' O3' -178.7(3) ?
C1' C2' C3' C4' 0.6(5) ?
O4 C4 C3 O3 3.5(4) ?
C4A C4 C3 O3 -176.9(2) ?
O4 C4 C3 C2 179.2(3) ?
C4A C4 C3 C2 -1.3(4) ?
O4' C4' C5' C6' 177.5(3) ?
C3' C4' C5' C6' -1.0(5) ?
O4' C4' C3' O3' 1.2(4) ?
C5' C4' C3' O3' 179.8(3) ?
O4' C4' C3' C2' -178.1(3) ?
C5' C4' C3' C2' 0.5(5) ?
C8A C4A C5 O5 -179.3(3) ?
C4 C4A C5 O5 1.4(4) ?
C8A C4A C5 C6 -1.6(4) ?
C4 C4A C5 C6 179.2(3) ?
C8A C4A C4 O4 -176.9(3) ?
C5 C4A C4 O4 2.3(4) ?
C8A C4A C4 C3 3.5(4) ?
C5 C4A C4 C3 -177.2(3) ?
C5 C4A C8A O1 178.9(2) ?
C4 C4A C8A O1 -1.9(4) ?
C5 C4A C8A C8 -1.1(4) ?
C4 C4A C8A C8 178.2(3) ?
O5 C5 C6 O6 3.2(4) ?
C4A C5 C6 O6 -174.5(2) ?
O5 C5 C6 C7 -179.0(2) ?
C4A C5 C6 C7 3.3(4) ?
C4' C5' C6' C1' 0.4(6) ?
O7 C7 C6 O6 -3.3(4) ?
C8 C7 C6 O6 175.4(3) ?
O7 C7 C6 C5 178.9(2) ?
C8 C7 C6 C5 -2.4(5) ?
C7 C8 C8A O1 -178.0(2) ?
C7 C8 C8A C4A 2.0(4) ?
C8A C8 C7 O7 178.4(3) ?
C8A C8 C7 C6 -0.2(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4474632
