#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/82/2208283.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_2208283
loop_
_publ_author_name
'M. Shaiq Ali'
'Shamsher Ali'
'Shazia Anjum'
'Waqar Ahmad'
_publ_section_title
;
 5-Hydroxy-4',6,7-trimethoxyflavone
;
_journal_coeditor_code           CI2005
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1107
_journal_page_last               o1109
_journal_paper_doi               10.1107/S1600536806005617
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C18 H16 O6'
_chemical_formula_moiety         'C18 H16 O6'
_chemical_formula_sum            'C18 H16 O6'
_chemical_formula_weight         328.31
_chemical_melting_point          468
_chemical_name_common            Salvesigenine
_chemical_name_systematic
;
5-Hydroxy-4',6,7-trimethoxyflavone
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                76.6810(10)
_cell_angle_beta                 85.7570(10)
_cell_angle_gamma                81.3810(10)
_cell_formula_units_Z            2
_cell_length_a                   7.0968(3)
_cell_length_b                   7.4959(3)
_cell_length_c                   14.9563(6)
_cell_measurement_reflns_used    5177
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.06
_cell_measurement_theta_min      2.80
_cell_volume                     764.84(5)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material
'SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0178
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7381
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.80
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.9798
_exptl_absorpt_correction_T_min  0.9372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Slab
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.215
_refine_ls_extinction_coef       0.060(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2677
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0398
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0775P)²+0.12P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1142
_refine_ls_wR_factor_ref         0.1212
_reflns_number_gt                2416
_reflns_number_total             2677
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2005.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2208283
_cod_database_fobs_code          2208283
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.47408(12) 0.77785(12) 0.60606(6) 0.0441(3) Uani d . 1
O O2 1.03835(13) 0.58305(16) 0.63712(7) 0.0647(3) Uani d . 1
O O3 1.00555(13) 0.63232(15) 0.80257(7) 0.0595(3) Uani d . 1
H H3A 1.0579 0.6032 0.7563 0.089 Uiso calc R 1
O O5 0.40744(13) 0.87819(14) 0.91009(6) 0.0564(3) Uani d . 1
O O4 0.77871(14) 0.75576(13) 0.93782(6) 0.0551(3) Uani d . 1
O O4' 0.15454(15) 0.80889(15) 0.22366(7) 0.0630(3) Uani d . 1
C C2 0.58325(18) 0.72571(16) 0.53525(8) 0.0420(3) Uani d . 1
C C3 0.77087(19) 0.66083(19) 0.54392(9) 0.0481(3) Uani d . 1
H H3B 0.8410 0.6264 0.4941 0.058 Uiso calc R 1
C C4 0.86455(18) 0.64371(18) 0.62747(9) 0.0473(3) Uani d . 1
C C5 0.81966(17) 0.69505(17) 0.78745(9) 0.0439(3) Uani d . 1
C C6 0.70248(18) 0.75276(17) 0.85607(8) 0.0445(3) Uani d . 1
C C7 0.50909(18) 0.81853(17) 0.83957(8) 0.0444(3) Uani d . 1
C C8 0.43273(17) 0.82273(17) 0.75613(9) 0.0445(3) Uani d . 1
H H8A 0.3039 0.8625 0.7462 0.053 Uiso calc R 1
C C9 0.55347(17) 0.76620(16) 0.68837(8) 0.0404(3) Uani d . 1
C C10 0.74627(17) 0.70129(16) 0.70113(8) 0.0416(3) Uani d . 1
C C1' 0.47365(18) 0.74826(16) 0.45337(9) 0.0424(3) Uani d . 1
C C2' 0.27932(19) 0.81780(18) 0.45180(9) 0.0477(3) Uani d . 1
H H2'A 0.2177 0.8512 0.5038 0.057 Uiso calc R 1
C C3' 0.1783(2) 0.83728(19) 0.37430(9) 0.0515(3) Uani d . 1
H H3'A 0.0495 0.8845 0.3742 0.062 Uiso calc R 1
C C4' 0.2672(2) 0.78707(17) 0.29612(9) 0.0482(3) Uani d . 1
C C5' 0.4599(2) 0.71748(19) 0.29667(9) 0.0517(3) Uani d . 1
H H5'A 0.5209 0.6837 0.2447 0.062 Uiso calc R 1
C C6' 0.5605(2) 0.69861(18) 0.37454(9) 0.0496(3) Uani d . 1
H H6'A 0.6894 0.6516 0.3743 0.060 Uiso calc R 1
C C11 0.2163(2) 0.9651(2) 0.89408(10) 0.0607(4) Uani d . 1
H H11A 0.1671 1.0180 0.9452 0.091 Uiso calc R 1
H H11B 0.1387 0.8750 0.8873 0.091 Uiso calc R 1
H H11C 0.2143 1.0610 0.8390 0.091 Uiso calc R 1
C C12 0.7428(3) 0.6073(2) 1.01175(10) 0.0726(5) Uani d . 1
H H12A 0.8081 0.6142 1.0646 0.109 Uiso calc R 1
H H12B 0.7878 0.4921 0.9946 0.109 Uiso calc R 1
H H12C 0.6082 0.6150 1.0262 0.109 Uiso calc R 1
C C7' 0.2437(3) 0.7713(2) 0.14028(9) 0.0632(4) Uani d . 1
H H7'A 0.1484 0.7839 0.0961 0.095 Uiso calc R 1
H H7'B 0.3102 0.6474 0.1519 0.095 Uiso calc R 1
H H7'C 0.3325 0.8573 0.1167 0.095 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 0.0033 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'
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 C9 120.22(10) ?
C5 O3 H3A 109.5 ?
C7 O5 C11 117.62(10) y
C6 O4 C12 114.58(10) y
C4' O4' C7' 117.55(12) y
C3 C2 O1 121.44(12) ?
C3 C2 C1' 126.34(12) ?
O1 C2 C1' 112.23(11) ?
C2 C3 C4 121.89(12) ?
C2 C3 H3B 119.1 ?
C4 C3 H3B 119.1 ?
O2 C4 C3 122.93(12) ?
O2 C4 C10 121.46(12) ?
C3 C4 C10 115.61(11) ?
O3 C5 C6 119.85(11) ?
O3 C5 C10 119.72(12) ?
C6 C5 C10 120.43(12) ?
O4 C6 C5 119.61(11) ?
O4 C6 C7 120.83(12) ?
C5 C6 C7 119.45(11) ?
O5 C7 C8 123.77(12) ?
O5 C7 C6 114.96(11) ?
C8 C7 C6 121.26(12) ?
C9 C8 C7 118.08(11) ?
C9 C8 H8A 121.0 ?
C7 C8 H8A 121.0 ?
O1 C9 C8 116.34(11) ?
O1 C9 C10 120.88(11) ?
C8 C9 C10 122.78(12) ?
C9 C10 C5 117.98(12) ?
C9 C10 C4 119.96(12) ?
C5 C10 C4 122.06(12) ?
C6' C1' C2' 117.94(12) ?
C6' C1' C2 120.47(12) ?
C2' C1' C2 121.59(11) ?
C3' C2' C1' 120.78(12) ?
C3' C2' H2'A 119.6 ?
C1' C2' H2'A 119.6 ?
C2' C3' C4' 120.57(13) ?
C2' C3' H3'A 119.7 ?
C4' C3' H3'A 119.7 ?
O4' C4' C5' 124.58(12) ?
O4' C4' C3' 116.08(12) ?
C5' C4' C3' 119.33(12) ?
C6' C5' C4' 119.84(12) ?
C6' C5' H5'A 120.1 ?
C4' C5' H5'A 120.1 ?
C5' C6' C1' 121.54(13) ?
C5' C6' H6'A 119.2 ?
C1' C6' H6'A 119.2 ?
O5 C11 H11A 109.5 ?
O5 C11 H11B 109.5 ?
H11A C11 H11B 109.5 ?
O5 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 ?
O4' C7' H7'A 109.5 ?
O4' C7' H7'B 109.5 ?
H7'A C7' H7'B 109.5 ?
O4' C7' H7'C 109.5 ?
H7'A C7' H7'C 109.5 ?
H7'B C7' H7'C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 1.3613(15) y
O1 C9 1.3707(15) y
O2 C4 1.2558(15) y
O3 C5 1.3498(15) y
O3 H3A 0.82 ?
O5 C7 1.3567(15) y
O5 C11 1.4262(17) y
O4 C6 1.3792(14) y
O4 C12 1.4149(18) y
O4' C4' 1.3594(16) y
O4' C7' 1.4236(18) y
C2 C3 1.3523(18) y
C2 C1' 1.4627(18) ?
C3 C4 1.4294(18) ?
C3 H3B 0.93 ?
C4 C10 1.4417(18) ?
C5 C6 1.3793(18) ?
C5 C10 1.4157(18) ?
C6 C7 1.4067(18) ?
C7 C8 1.3889(17) ?
C8 C9 1.3789(18) ?
C8 H8A 0.93 ?
C9 C10 1.3934(17) ?
C1' C6' 1.3909(18) ?
C1' C2' 1.3993(18) ?
C2' C3' 1.3755(18) ?
C2' H2'A 0.93 ?
C3' C4' 1.3889(19) ?
C3' H3'A 0.93 ?
C4' C5' 1.388(2) ?
C5' C6' 1.3795(19) ?
C5' H5'A 0.93 ?
C6' H6'A 0.93 ?
C11 H11A 0.96 ?
C11 H11B 0.96 ?
C11 H11C 0.96 ?
C12 H12A 0.96 ?
C12 H12B 0.96 ?
C12 H12C 0.96 ?
C7' H7'A 0.96 ?
C7' H7'B 0.96 ?
C7' H7'C 0.96 ?
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
O3 H3A O2 1_555 0.82 1.84 2.5737(15) 148 y
C2' H2'A O1 1_555 0.93 2.38 2.7116(16) 101 y
C6' H6'A O2 2_766 0.93 2.43 3.2996(18) 155 y
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
C9 O1 C2 C3 0.29(18) ?
C9 O1 C2 C1' -179.93(9) ?
O1 C2 C3 C4 -0.1(2) ?
C1' C2 C3 C4 -179.82(11) ?
C2 C3 C4 O2 179.67(12) ?
C2 C3 C4 C10 -0.4(2) ?
C12 O4 C6 C5 -102.97(15) ?
C12 O4 C6 C7 80.99(16) y
O3 C5 C6 O4 3.68(18) ?
C10 C5 C6 O4 -176.28(10) ?
O3 C5 C6 C7 179.78(11) ?
C10 C5 C6 C7 -0.18(19) ?
C11 O5 C7 C8 -5.84(19) y
C11 O5 C7 C6 173.28(12) ?
O4 C6 C7 O5 -1.67(17) ?
C5 C6 C7 O5 -177.72(11) ?
O4 C6 C7 C8 177.48(10) ?
C5 C6 C7 C8 1.43(19) ?
O5 C7 C8 C9 176.95(11) ?
C6 C7 C8 C9 -2.12(19) ?
C2 O1 C9 C8 179.70(10) ?
C2 O1 C9 C10 0.04(18) ?
C7 C8 C9 O1 -178.01(10) ?
C7 C8 C9 C10 1.64(19) ?
O1 C9 C10 C5 179.20(10) ?
C8 C9 C10 C5 -0.44(19) ?
O1 C9 C10 C4 -0.58(18) ?
C8 C9 C10 C4 179.79(11) ?
O3 C5 C10 C9 179.73(10) ?
C6 C5 C10 C9 -0.31(18) ?
O3 C5 C10 C4 -0.50(19) ?
C6 C5 C10 C4 179.46(11) ?
O2 C4 C10 C9 -179.35(12) ?
C3 C4 C10 C9 0.75(18) ?
O2 C4 C10 C5 0.9(2) ?
C3 C4 C10 C5 -179.02(10) ?
C3 C2 C1' C6' 1.0(2) ?
O1 C2 C1' C6' -178.75(10) ?
C3 C2 C1' C2' -179.71(12) ?
O1 C2 C1' C2' 0.52(17) ?
C6' C1' C2' C3' -0.42(19) ?
C2 C1' C2' C3' -179.71(11) ?
C1' C2' C3' C4' 0.4(2) ?
C7' O4' C4' C5' -5.1(2) y
C7' O4' C4' C3' 175.63(11) ?
C2' C3' C4' O4' 179.00(11) ?
C2' C3' C4' C5' -0.3(2) ?
O4' C4' C5' C6' -179.07(12) ?
C3' C4' C5' C6' 0.1(2) ?
C4' C5' C6' C1' -0.2(2) ?
C2' C1' C6' C5' 0.3(2) ?
C2 C1' C6' C5' 179.59(11) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 141666
2 PubChem 161271
