#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/75/2207508.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_2207508
loop_
_publ_author_name
'Jeannie Bee Jan Teh'
'Hoong-Kun Fun'
'Abdul Razak Ibrahim'
'Suchada Chantrapromma'
'Nawong Boonnak'
'Chatchanok Karalai'
_publ_section_title
;
5-Hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one.
Corrigendum
;
_journal_coeditor_code           CI9676
_journal_issue                   12
_journal_name_full               'Acta Crystallographica, Section E'
_journal_page_first              e11
_journal_page_last               e11
_journal_paper_doi               10.1107/S1600536805037840
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C17 H14 O5'
_chemical_formula_moiety         'C17 H14 O5'
_chemical_formula_sum            'C17 H14 O5'
_chemical_formula_weight         298.28
_chemical_melting_point          .447E-305
_chemical_name_common
;
5-hydroxy-7,4'-dimethoxyflavone
;
_chemical_name_systematic
;
5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 106.520(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.9406(4)
_cell_length_b                   3.86190(10)
_cell_length_c                   21.7968(4)
_cell_measurement_reflns_used    3581
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      28.00
_cell_measurement_theta_min      1.95
_cell_volume                     1367.15(9)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and PLATON (Spek, 2003)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1998)'
_diffrn_ambient_temperature      297(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX2 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  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0287
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            17884
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         1.95
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.209
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3283
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0462
_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)+(0.0571P)²+0.2601P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1280
_reflns_number_gt                2207
_reflns_number_total             3283
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci9676.cif
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2207508
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'
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_type_symbol
O1 0.15499(6) 0.9753(3) 0.37516(4) 0.0409(3) Uani d . 1 O
O2 0.25586(7) 0.5256(3) 0.54929(5) 0.0541(4) Uani d . 1 O
O3 0.39800(7) 0.5554(4) 0.52901(5) 0.0560(4) Uani d . 1 O
H3 0.3636 0.5130 0.5479 0.084 Uiso calc R 1 H
O4 0.40678(7) 1.0285(3) 0.32828(5) 0.0538(4) Uani d . 1 O
O5 -0.22834(7) 1.0817(4) 0.28553(5) 0.0533(4) Uani d . 1 O
C1 0.23874(9) 0.9148(4) 0.39514(7) 0.0362(4) Uani d . 1 C
C2 0.28282(10) 1.0058(4) 0.35373(7) 0.0412(4) Uani d . 1 C
H2 0.2573 1.1094 0.3146 0.049 Uiso calc R 1 H
C3 0.36683(10) 0.9380(5) 0.37218(7) 0.0414(4) Uani d . 1 C
C4 0.40646(10) 0.7874(5) 0.43095(7) 0.0440(4) Uani d . 1 C
H4 0.4628 0.7452 0.4424 0.053 Uiso calc R 1 H
C5 0.36052(10) 0.7022(5) 0.47179(7) 0.0412(4) Uani d . 1 C
C6 0.27504(9) 0.7617(4) 0.45482(6) 0.0362(4) Uani d . 1 C
C7 0.22512(10) 0.6656(4) 0.49571(7) 0.0397(4) Uani d . 1 C
C8 0.13922(10) 0.7345(5) 0.47088(7) 0.0411(4) Uani d . 1 C
H8 0.1045 0.6780 0.4956 0.049 Uiso calc R 1 H
C9 0.10645(9) 0.8792(4) 0.41260(6) 0.0362(4) Uani d . 1 C
C10 0.01916(10) 0.9446(4) 0.38162(6) 0.0355(4) Uani d . 1 C
C11 -0.04119(10) 0.8394(5) 0.40996(7) 0.0424(4) Uani d . 1 C
H11 -0.0249 0.7380 0.4503 0.051 Uiso calc R 1 H
C12 -0.12400(10) 0.8807(5) 0.38018(7) 0.0424(4) Uani d . 1 C
H12 -0.1628 0.8085 0.4002 0.051 Uiso calc R 1 H
C13 -0.14880(10) 1.0311(4) 0.31993(7) 0.0399(4) Uani d . 1 C
C14 -0.08988(10) 1.1419(5) 0.29100(7) 0.0444(4) Uani d . 1 C
H14 -0.1064 1.2448 0.2508 0.053 Uiso calc R 1 H
C15 -0.00750(10) 1.1007(5) 0.32127(7) 0.0411(4) Uani d . 1 C
H15 0.0311 1.1775 0.3014 0.049 Uiso calc R 1 H
C16 0.49030(11) 0.9268(6) 0.33992(9) 0.0601(5) Uani d . 1 C
H16A 0.5094 0.9900 0.3040 0.090 Uiso calc R 1 H
H16B 0.4947 0.6806 0.3460 0.090 Uiso calc R 1 H
H16C 0.5233 1.0410 0.3777 0.090 Uiso calc R 1 H
C17 -0.29207(11) 0.9581(6) 0.31075(9) 0.0553(5) Uani d . 1 C
H17A -0.3447 1.0069 0.2810 0.083 Uiso calc R 1 H
H17B -0.2882 1.0716 0.3507 0.083 Uiso calc R 1 H
H17C -0.2862 0.7127 0.3175 0.083 Uiso calc R 1 H
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
C9 O1 C1 120.35(11) ?
C5 O3 H3 109.5 ?
C3 O4 C16 118.12(14) yes
C13 O5 C17 118.72(13) yes
C2 C1 O1 116.89(13) ?
C2 C1 C6 122.80(14) ?
O1 C1 C6 120.31(13) ?
C1 C2 C3 117.78(14) ?
C1 C2 H2 121.1 ?
C3 C2 H2 121.1 ?
O4 C3 C2 114.83(14) ?
O4 C3 C4 123.09(15) ?
C2 C3 C4 122.08(14) ?
C5 C4 C3 118.71(15) ?
C5 C4 H4 120.6 ?
C3 C4 H4 120.6 ?
O3 C5 C4 119.48(14) ?
O3 C5 C6 119.26(14) ?
C4 C5 C6 121.25(14) ?
C1 C6 C5 117.37(14) ?
C1 C6 C7 120.18(14) ?
C5 C6 C7 122.44(13) ?
O2 C7 C8 122.75(14) ?
O2 C7 C6 121.62(15) ?
C8 C7 C6 115.63(13) ?
C9 C8 C7 122.34(14) ?
C9 C8 H8 118.8 ?
C7 C8 H8 118.8 ?
C8 C9 O1 121.16(14) ?
C8 C9 C10 126.55(14) ?
O1 C9 C10 112.28(12) ?
C11 C10 C15 117.37(15) ?
C11 C10 C9 121.11(13) yes
C15 C10 C9 121.46(14) ?
C12 C11 C10 122.24(14) ?
C12 C11 H11 118.9 ?
C10 C11 H11 118.9 ?
C11 C12 C13 119.23(14) ?
C11 C12 H12 120.4 ?
C13 C12 H12 120.4 ?
O5 C13 C12 124.69(14) ?
O5 C13 C14 115.66(13) ?
C12 C13 C14 119.65(15) ?
C15 C14 C13 120.59(14) ?
C15 C14 H14 119.7 ?
C13 C14 H14 119.7 ?
C14 C15 C10 120.92(14) ?
C14 C15 H15 119.5 ?
C10 C15 H15 119.5 ?
O4 C16 H16A 109.5 ?
O4 C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
O4 C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
O5 C17 H17A 109.5 ?
O5 C17 H17B 109.5 ?
H17A C17 H17B 109.5 ?
O5 C17 H17C 109.5 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C9 1.3645(17) yes
O1 C1 1.3804(18) yes
O2 C7 1.2578(17) yes
O3 C5 1.3526(18) yes
O3 H3 0.82 ?
O4 C3 1.3652(19) yes
O4 C16 1.420(2) yes
O5 C13 1.3570(18) yes
O5 C17 1.426(2) yes
C1 C2 1.371(2) ?
C1 C6 1.402(2) ?
C2 C3 1.389(2) ?
C2 H2 0.93 ?
C3 C4 1.393(2) ?
C4 C5 1.379(2) ?
C4 H4 0.93 ?
C5 C6 1.408(2) ?
C6 C7 1.441(2) ?
C7 C8 1.426(2) ?
C8 C9 1.354(2) yes
C8 H8 0.93 ?
C9 C10 1.462(2) ?
C10 C11 1.397(2) ?
C10 C15 1.400(2) ?
C11 C12 1.377(2) ?
C11 H11 0.93 ?
C12 C13 1.387(2) ?
C12 H12 0.93 ?
C13 C14 1.391(2) ?
C14 C15 1.373(2) ?
C14 H14 0.93 ?
C15 H15 0.93 ?
C16 H16A 0.96 ?
C16 H16B 0.96 ?
C16 H16C 0.96 ?
C17 H17A 0.96 ?
C17 H17B 0.96 ?
C17 H17C 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 H3 O2 1_555 0.82 1.83 2.571(2) 149 y
C4 H4 O3 3_666 0.93 2.54 3.441(2) 163 y
C12 H12 O2 3_566 0.93 2.52 3.430(2) 167 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 C1 C2 177.38(14) ?
C9 O1 C1 C6 -1.6(2) ?
O1 C1 C2 C3 -178.23(14) ?
C6 C1 C2 C3 0.7(3) ?
C16 O4 C3 C2 -171.93(16) yes
C16 O4 C3 C4 7.7(3) yes
C1 C2 C3 O4 178.75(15) ?
C1 C2 C3 C4 -0.9(3) ?
O4 C3 C4 C5 -179.36(16) ?
C2 C3 C4 C5 0.3(3) ?
C3 C4 C5 O3 179.93(16) ?
C3 C4 C5 C6 0.6(3) ?
C2 C1 C6 C5 0.1(2) ?
O1 C1 C6 C5 179.00(14) ?
C2 C1 C6 C7 -178.76(16) ?
O1 C1 C6 C7 0.1(2) ?
O3 C5 C6 C1 179.90(15) ?
C4 C5 C6 C1 -0.8(3) ?
O3 C5 C6 C7 -1.3(3) ?
C4 C5 C6 C7 178.07(15) ?
C1 C6 C7 O2 179.49(15) ?
C5 C6 C7 O2 0.7(3) ?
C1 C6 C7 C8 0.5(2) ?
C5 C6 C7 C8 -178.31(15) ?
O2 C7 C8 C9 -178.69(16) ?
C6 C7 C8 C9 0.3(2) ?
C7 C8 C9 O1 -1.7(3) ?
C7 C8 C9 C10 176.83(16) ?
C1 O1 C9 C8 2.4(2) ?
C1 O1 C9 C10 -176.37(13) ?
C8 C9 C10 C11 -3.7(3) ?
O1 C9 C10 C11 174.93(14) ?
C8 C9 C10 C15 179.17(16) ?
O1 C9 C10 C15 -2.2(2) ?
C15 C10 C11 C12 0.9(3) ?
C9 C10 C11 C12 -176.32(15) ?
C10 C11 C12 C13 0.1(3) ?
C17 O5 C13 C12 -3.3(3) yes
C17 O5 C13 C14 176.77(16) yes
C11 C12 C13 O5 179.16(16) ?
C11 C12 C13 C14 -0.9(3) ?
O5 C13 C14 C15 -179.42(15) ?
C12 C13 C14 C15 0.6(3) ?
C13 C14 C15 C10 0.4(3) ?
C11 C10 C15 C14 -1.1(2) ?
C9 C10 C15 C14 176.05(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4444920
