#------------------------------------------------------------------------------
#$Date: 2020-06-06 01:26:40 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252948 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/21/2022143.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_2022143
loop_
_publ_author_name
'De Grano, Ruel Valerio Robles'
'Vashchenko, Elena V.'
'Nisar, Madiha'
'Sung, Herman H.-Y.'
'Vashchenko, Valerii V.'
'Williams, Ian D.'
_publ_section_title
;
 Crystal structures of the flavonoid Oroxylin A and the regioisomers
 Negletein and Wogonin
;
_journal_coeditor_code           WP3006
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              490
_journal_page_last               499
_journal_paper_doi               10.1107/S2053229620005550
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C16 H12 O5, 1.25H2 O'
_chemical_formula_moiety         'C16 H12 O5, 1.25(H2 O)'
_chemical_formula_sum            'C16 H14.5 O6.25'
_chemical_formula_weight         306.78
_chemical_name_systematic
;
5,7-Dihydroxy-8-methoxy-2-phenyl-4H-chromen-4-one 1.25-hydrate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.5918(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.39382(9)
_cell_length_b                   18.7848(3)
_cell_length_c                   16.8308(3)
_cell_measurement_reflns_used    4183
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.2480
_cell_measurement_theta_min      3.5260
_cell_volume                     1379.98(4)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2020)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2020)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2020)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device       'Kappa diffractometer'
_diffrn_measurement_device_type
'Rigaku OD SuperNova Dual source diffractometer with an Atlas detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7256
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.496
_diffrn_reflns_theta_min         7.092
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  30
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.970
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2020)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             642
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.265
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         2416
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0439
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0532P)²+0.6430P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1134
_reflns_number_gt                2173
_reflns_number_total             2416
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wp3006sup1.cif
_cod_data_source_block           val3h
_cod_original_cell_volume        1379.98(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C16 H14.50 O6.25'
_cod_database_code               2022143
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.698
_shelx_estimated_absorpt_t_max   0.953
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.5558(2) 0.76190(5) 0.18290(6) 0.0235(3) Uani d 1 . .
O O4 0.2880(3) 0.84255(8) 0.38900(7) 0.0502(4) Uani d 1 . .
O O5 -0.0181(3) 0.72740(9) 0.40586(8) 0.0547(4) Uani d 1 . .
H H5 0.0171 0.7712 0.4110 0.082 Uiso calc 1 . .
O O7 0.0203(4) 0.54743(7) 0.21340(9) 0.0601(5) Uani d 1 . .
H H7 0.0847 0.5393 0.1692 0.090 Uiso calc 1 . .
O O8 0.4021(3) 0.62888(6) 0.12845(6) 0.0360(3) Uani d 1 . .
C C2 0.6428(3) 0.82849(8) 0.20820(9) 0.0257(3) Uani d 1 . .
C C3 0.5591(4) 0.85584(9) 0.27672(10) 0.0324(4) Uani d 1 . .
H H3 0.6278 0.9021 0.2931 0.039 Uiso calc 1 . .
C C4 0.3708(4) 0.81719(9) 0.32510(9) 0.0322(4) Uani d 1 . .
C C5 0.0852(4) 0.70379(10) 0.33789(10) 0.0362(4) Uani d 1 . .
C C6 0.0029(4) 0.63732(11) 0.30907(11) 0.0414(5) Uani d 1 . .
H H6 -0.1235 0.6078 0.3373 0.050 Uiso calc 1 . .
C C7 0.1051(4) 0.61308(9) 0.23829(10) 0.0380(4) Uani d 1 . .
C C8 0.2905(4) 0.65540(8) 0.19546(9) 0.0284(3) Uani d 1 . .
C C9 0.3729(3) 0.72211(8) 0.22582(8) 0.0230(3) Uani d 1 . .
C C10 0.2746(3) 0.74783(9) 0.29687(9) 0.0281(3) Uani d 1 . .
C C17 0.2384(5) 0.65378(9) 0.05454(10) 0.0372(4) Uani d 1 . .
H H17A 0.0199 0.6431 0.0540 0.056 Uiso calc 1 . .
H H17B 0.3177 0.6299 0.0094 0.056 Uiso calc 1 . .
H H17C 0.2665 0.7053 0.0500 0.056 Uiso calc 1 . .
C C11 0.8273(3) 0.86362(8) 0.15237(11) 0.0306(4) Uani d 1 . .
C C12 0.8860(4) 0.82958(9) 0.08227(11) 0.0350(4) Uani d 1 . .
H H12 0.8047 0.7834 0.0706 0.042 Uiso calc 1 . .
C C13 1.0614(4) 0.86210(11) 0.02931(13) 0.0453(5) Uani d 1 . .
H H13 1.1004 0.8382 -0.0182 0.054 Uiso calc 1 . .
C C14 1.1796(4) 0.92934(12) 0.04586(15) 0.0524(6) Uani d 1 . .
H H14 1.3020 0.9516 0.0100 0.063 Uiso calc 1 . .
C C15 1.1187(4) 0.96427(11) 0.11507(16) 0.0554(6) Uani d 1 . .
H H15 1.1974 1.0108 0.1259 0.066 Uiso calc 1 . .
C C16 0.9449(4) 0.93205(9) 0.16824(13) 0.0425(5) Uani d 1 . .
H H16 0.9053 0.9563 0.2155 0.051 Uiso calc 1 . .
O O1W 0.2844(10) 0.47744(16) 0.0807(2) 0.0736(11) Uani d 0.5 A -1
H H1WA 0.3395 0.4794 0.0328 0.110 Uiso d 0.5 A -1
H H1WB 0.2718 0.4321 0.0906 0.110 Uiso d 0.5 A -1
O O2W 0.9631(8) 0.48649(13) 0.07684(15) 0.0452(7) Uani d 0.5 B -1
H H2WA 1.0454 0.4953 0.0333 0.068 Uiso d 0.5 B -1
H H2WB 0.7786 0.4720 0.0602 0.068 Uiso d 0.5 B -1
O O3W 0.3848(16) 0.5034(3) -0.0616(4) 0.0568(15) Uani d 0.25 C -1
H H3WA 0.4666 0.4618 -0.0670 0.085 Uiso d 0.25 C -1
H H3WB 0.2256 0.5042 -0.0974 0.085 Uiso d 0.25 C -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'
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 . . 119.93(12) ?
C5 O5 H5 . . 109.5 ?
C7 O7 H7 . . 109.5 ?
C8 O8 C17 . . 113.64(13) ?
O1 C2 C11 . . 111.64(13) ?
C3 C2 O1 . . 121.47(15) ?
C3 C2 C11 . . 126.89(15) ?
C2 C3 H3 . . 119.1 ?
C2 C3 C4 . . 121.78(15) ?
C4 C3 H3 . . 119.1 ?
O4 C4 C3 . . 122.38(17) ?
O4 C4 C10 . . 121.37(17) ?
C3 C4 C10 . . 116.23(14) ?
O5 C5 C6 . . 119.77(17) ?
O5 C5 C10 . . 119.75(18) ?
C6 C5 C10 . . 120.48(16) ?
C5 C6 H6 . . 120.0 ?
C5 C6 C7 . . 120.03(16) ?
C7 C6 H6 . . 120.0 ?
O7 C7 C6 . . 117.47(17) ?
O7 C7 C8 . . 121.31(18) ?
C8 C7 C6 . . 121.22(16) ?
O8 C8 C7 . . 120.11(14) ?
O8 C8 C9 . . 121.87(14) ?
C9 C8 C7 . . 117.88(15) ?
O1 C9 C8 . . 116.44(13) ?
O1 C9 C10 . . 121.37(14) ?
C8 C9 C10 . . 122.19(14) ?
C5 C10 C4 . . 122.63(15) ?
C9 C10 C4 . . 119.18(15) ?
C9 C10 C5 . . 118.18(15) ?
O8 C17 H17A . . 109.5 ?
O8 C17 H17B . . 109.5 ?
O8 C17 H17C . . 109.5 ?
H17A C17 H17B . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C12 C11 C2 . . 120.42(14) ?
C12 C11 C16 . . 118.90(17) ?
C16 C11 C2 . . 120.68(17) ?
C11 C12 H12 . . 119.5 ?
C13 C12 C11 . . 120.91(17) ?
C13 C12 H12 . . 119.5 ?
C12 C13 H13 . . 120.1 ?
C14 C13 C12 . . 119.8(2) ?
C14 C13 H13 . . 120.1 ?
C13 C14 H14 . . 120.1 ?
C13 C14 C15 . . 119.77(19) ?
C15 C14 H14 . . 120.1 ?
C14 C15 H15 . . 119.7 ?
C16 C15 C14 . . 120.69(19) ?
C16 C15 H15 . . 119.7 ?
C11 C16 H16 . . 120.1 ?
C15 C16 C11 . . 119.9(2) ?
C15 C16 H16 . . 120.1 ?
H1WA O1W H1WB . . 104.5 ?
H2WA O2W H2WB . . 104.5 ?
H3WA O3W H3WB . . 104.5 ?
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 . 1.3619(18) ?
O1 C9 . 1.3637(18) ?
O4 C4 . 1.267(2) ?
O5 H5 . 0.8400 ?
O5 C5 . 1.353(2) ?
O7 H7 . 0.8400 ?
O7 C7 . 1.341(2) ?
O8 C8 . 1.374(2) ?
O8 C17 . 1.442(2) ?
C2 C3 . 1.351(2) ?
C2 C11 . 1.467(2) ?
C3 H3 . 0.9500 ?
C3 C4 . 1.425(3) ?
C4 C10 . 1.434(2) ?
C5 C6 . 1.373(3) ?
C5 C10 . 1.409(2) ?
C6 H6 . 0.9500 ?
C6 C7 . 1.397(3) ?
C7 C8 . 1.397(2) ?
C8 C9 . 1.386(2) ?
C9 C10 . 1.403(2) ?
C17 H17A . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 0.9800 ?
C11 C12 . 1.392(3) ?
C11 C16 . 1.400(2) ?
C12 H12 . 0.9500 ?
C12 C13 . 1.385(3) ?
C13 H13 . 0.9500 ?
C13 C14 . 1.382(3) ?
C14 H14 . 0.9500 ?
C14 C15 . 1.389(4) ?
C15 H15 . 0.9500 ?
C15 C16 . 1.381(3) ?
C16 H16 . 0.9500 ?
O1W H1WA . 0.8699 ?
O1W H1WB . 0.8700 ?
O2W H2WA . 0.8691 ?
O2W H2WB . 0.8704 ?
O3W H3WA . 0.8701 ?
O3W H3WB . 0.8699 ?
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 . . . . -1.3(2) ?
O1 C2 C11 C12 . . . . 1.85(19) ?
O1 C2 C11 C16 . . . . -178.69(13) ?
O1 C9 C10 C4 . . . . -0.5(2) ?
O1 C9 C10 C5 . . . . 179.82(12) ?
O4 C4 C10 C5 . . . . -0.2(2) ?
O4 C4 C10 C9 . . . . -179.90(14) ?
O5 C5 C6 C7 . . . . 179.02(15) ?
O5 C5 C10 C4 . . . . 1.5(2) ?
O5 C5 C10 C9 . . . . -178.85(13) ?
O7 C7 C8 O8 . . . . -3.1(2) ?
O7 C7 C8 C9 . . . . -178.83(15) ?
O8 C8 C9 O1 . . . . 3.9(2) ?
O8 C8 C9 C10 . . . . -176.09(13) ?
C2 O1 C9 C8 . . . . 178.99(12) ?
C2 O1 C9 C10 . . . . -1.01(19) ?
C2 C3 C4 O4 . . . . -179.21(14) ?
C2 C3 C4 C10 . . . . -0.2(2) ?
C2 C11 C12 C13 . . . . -179.64(15) ?
C2 C11 C16 C15 . . . . 179.88(15) ?
C3 C2 C11 C12 . . . . -177.62(15) ?
C3 C2 C11 C16 . . . . 1.8(2) ?
C3 C4 C10 C5 . . . . -179.28(14) ?
C3 C4 C10 C9 . . . . 1.0(2) ?
C5 C6 C7 O7 . . . . 179.31(15) ?
C5 C6 C7 C8 . . . . -0.2(3) ?
C6 C5 C10 C4 . . . . -179.03(14) ?
C6 C5 C10 C9 . . . . 0.6(2) ?
C6 C7 C8 O8 . . . . 176.35(14) ?
C6 C7 C8 C9 . . . . 0.6(2) ?
C7 C8 C9 O1 . . . . 179.55(13) ?
C7 C8 C9 C10 . . . . -0.5(2) ?
C8 C9 C10 C4 . . . . 179.52(13) ?
C8 C9 C10 C5 . . . . -0.2(2) ?
C9 O1 C2 C3 . . . . 1.94(19) ?
C9 O1 C2 C11 . . . . -177.57(11) ?
C10 C5 C6 C7 . . . . -0.5(2) ?
C17 O8 C8 C7 . . . . 102.11(17) ?
C17 O8 C8 C9 . . . . -82.35(18) ?
C11 C2 C3 C4 . . . . 178.08(13) ?
C11 C12 C13 C14 . . . . -0.2(3) ?
C12 C11 C16 C15 . . . . -0.7(2) ?
C12 C13 C14 C15 . . . . -0.8(3) ?
C13 C14 C15 C16 . . . . 1.0(3) ?
C14 C15 C16 C11 . . . . -0.3(3) ?
C16 C11 C12 C13 . . . . 0.9(2) ?

_cod_database_fobs_code 2022143
