#------------------------------------------------------------------------------
#$Date: 2020-06-06 01:26:40 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252948 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/21/2022142.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_2022142
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_absolute_configuration ad
_chemical_formula_iupac          'C16 H12 O5, H2 O'
_chemical_formula_moiety         'C16 H12 O5, H2 O'
_chemical_formula_sum            'C16 H14 O6'
_chemical_formula_weight         302.27
_chemical_name_common            'Wogonin Monohydrate'
_chemical_name_systematic
;
5,7-Dihydroxy-8-methoxy-2-phenyl-4H-chromen-4-one monohydrate
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.64835(6)
_cell_length_b                   16.4123(2)
_cell_length_c                   18.3290(3)
_cell_measurement_reflns_used    3063
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.5080
_cell_measurement_theta_min      5.9180
_cell_volume                     1398.32(3)
_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_detector_area_resol_mean 10.3577
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_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_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0113
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3792
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.477
_diffrn_reflns_theta_min         7.244
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.936
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88381
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2020)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.135
_refine_ls_abs_structure_details
;
Flack x determined using 964 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   0.05(6)
_refine_ls_extinction_coef       0.0038(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2486
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0226
_refine_ls_R_factor_gt           0.0220
_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)+(0.0380P)²+0.1300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0589
_refine_ls_wR_factor_ref         0.0593
_reflns_number_gt                2433
_reflns_number_total             2486
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wp3006sup1.cif
_cod_data_source_block           madiha48cult
_cod_database_code               2022142
_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   0.767
_shelx_estimated_absorpt_t_max   0.872
loop_
_space_group_symop_operation_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'
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 0.5540(2) 0.57179(6) 0.22376(5) 0.0159(2) Uani d 1 . .
C C2 0.6132(3) 0.53999(9) 0.15689(8) 0.0158(3) Uani d 1 . .
C C3 0.4816(3) 0.47174(9) 0.13186(8) 0.0170(3) Uani d 1 . .
H H3 0.5327 0.4508 0.0853 0.020 Uiso calc 1 . .
O O4 0.1384(2) 0.36789(6) 0.15132(6) 0.0203(3) Uani d 1 . .
C C4 0.2671(3) 0.43068(9) 0.17412(8) 0.0163(3) Uani d 1 . .
O O5 -0.1549(2) 0.36529(7) 0.27217(6) 0.0213(3) Uani d 1 . .
H H5 -0.086(6) 0.3513(17) 0.2306(16) 0.056(8) Uiso d 1 . .
C C5 -0.0049(3) 0.43234(9) 0.29236(8) 0.0168(3) Uani d 1 . .
C C6 -0.0574(3) 0.46767(10) 0.35926(8) 0.0178(3) Uani d 1 . .
H H6 -0.1968 0.4448 0.3912 0.021 Uiso calc 1 . .
O O7 0.0424(3) 0.56936(7) 0.44646(6) 0.0212(3) Uani d 1 . .
H H7 0.163(5) 0.6117(15) 0.4551(13) 0.039(6) Uiso d 1 . .
C C7 0.0955(3) 0.53744(9) 0.38004(8) 0.0170(3) Uani d 1 . .
O O8 0.4543(2) 0.63908(6) 0.35711(6) 0.0189(2) Uani d 1 . .
C C8 0.3008(3) 0.57230(9) 0.33407(8) 0.0162(3) Uani d 1 . .
C C9 0.3508(3) 0.53563(9) 0.26700(8) 0.0148(3) Uani d 1 . .
C C10 0.2027(3) 0.46562(9) 0.24440(8) 0.0153(3) Uani d 1 . .
C C11 0.8294(3) 0.58814(9) 0.11764(8) 0.0161(3) Uani d 1 . .
C C12 0.9489(3) 0.65811(10) 0.14900(8) 0.0193(3) Uani d 1 . .
H H12 0.8885 0.6750 0.1962 0.023 Uiso calc 1 . .
C C13 1.1543(3) 0.70295(10) 0.11190(9) 0.0217(3) Uani d 1 . .
H H13 1.2354 0.7501 0.1339 0.026 Uiso calc 1 . .
C C14 1.2420(3) 0.67930(10) 0.04282(9) 0.0217(3) Uani d 1 . .
H H14 1.3842 0.7099 0.0176 0.026 Uiso calc 1 . .
C C15 1.1213(3) 0.61064(10) 0.01052(9) 0.0214(3) Uani d 1 . .
H H15 1.1788 0.5951 -0.0372 0.026 Uiso calc 1 . .
C C16 0.9188(3) 0.56505(10) 0.04729(8) 0.0193(3) Uani d 1 . .
H H16 0.8394 0.5179 0.0250 0.023 Uiso calc 1 . .
C C17 0.3416(4) 0.71412(10) 0.32867(10) 0.0273(4) Uani d 1 . .
H H17A 0.3639 0.7149 0.2755 0.041 Uiso calc 1 . .
H H17B 0.4468 0.7601 0.3500 0.041 Uiso calc 1 . .
H H17C 0.1372 0.7186 0.3411 0.041 Uiso calc 1 . .
O O1W 0.2807(3) 0.70168(7) 0.51350(6) 0.0214(3) Uani d 1 . .
H H1WA 0.430(7) 0.7262(16) 0.5025(16) 0.055(8) Uiso d 1 . .
H H1WB 0.312(5) 0.6794(13) 0.5572(14) 0.037(6) Uiso d 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 . . 119.69(12) ?
O1 C2 C11 . . 111.96(12) ?
C3 C2 O1 . . 122.02(14) ?
C3 C2 C11 . . 126.01(14) ?
C2 C3 H3 . . 119.3 ?
C2 C3 C4 . . 121.34(14) ?
C4 C3 H3 . . 119.3 ?
C3 C4 C10 . . 116.17(14) ?
O4 C4 C3 . . 122.36(14) ?
O4 C4 C10 . . 121.47(14) ?
C5 O5 H5 . . 105.6(19) ?
O5 C5 C6 . . 119.60(14) ?
O5 C5 C10 . . 119.67(13) ?
C6 C5 C10 . . 120.72(14) ?
C5 C6 H6 . . 120.1 ?
C5 C6 C7 . . 119.75(14) ?
C7 C6 H6 . . 120.1 ?
C7 O7 H7 . . 110.1(16) ?
O7 C7 C6 . . 118.06(13) ?
O7 C7 C8 . . 120.73(14) ?
C8 C7 C6 . . 121.20(14) ?
C8 O8 C17 . . 112.52(12) ?
O8 C8 C7 . . 119.77(13) ?
O8 C8 C9 . . 122.06(13) ?
C9 C8 C7 . . 118.12(14) ?
O1 C9 C8 . . 116.14(13) ?
O1 C9 C10 . . 121.54(13) ?
C8 C9 C10 . . 122.32(14) ?
C5 C10 C4 . . 122.89(14) ?
C9 C10 C4 . . 119.22(14) ?
C9 C10 C5 . . 117.89(13) ?
C12 C11 C2 . . 120.83(14) ?
C12 C11 C16 . . 118.70(14) ?
C16 C11 C2 . . 120.47(14) ?
C11 C12 H12 . . 119.7 ?
C13 C12 C11 . . 120.56(14) ?
C13 C12 H12 . . 119.7 ?
C12 C13 H13 . . 119.9 ?
C12 C13 C14 . . 120.20(15) ?
C14 C13 H13 . . 119.9 ?
C13 C14 H14 . . 120.1 ?
C13 C14 C15 . . 119.80(15) ?
C15 C14 H14 . . 120.1 ?
C14 C15 H15 . . 119.8 ?
C16 C15 C14 . . 120.47(15) ?
C16 C15 H15 . . 119.8 ?
C11 C16 H16 . . 119.9 ?
C15 C16 C11 . . 120.25(15) ?
C15 C16 H16 . . 119.9 ?
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 ?
H1WA O1W H1WB . . 106(3) ?
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 . 1.3602(18) ?
O1 C9 . 1.3682(18) ?
C2 C3 . 1.356(2) ?
C2 C11 . 1.467(2) ?
C3 H3 . 0.9500 ?
C3 C4 . 1.431(2) ?
O4 C4 . 1.2626(19) ?
C4 C10 . 1.442(2) ?
O5 H5 . 0.86(3) ?
O5 C5 . 1.3540(19) ?
C5 C6 . 1.378(2) ?
C5 C10 . 1.415(2) ?
C6 H6 . 0.9500 ?
C6 C7 . 1.401(2) ?
O7 H7 . 0.91(3) ?
O7 C7 . 1.3481(18) ?
C7 C8 . 1.396(2) ?
O8 C8 . 1.3743(19) ?
O8 C17 . 1.4363(19) ?
C8 C9 . 1.388(2) ?
C9 C10 . 1.402(2) ?
C11 C12 . 1.399(2) ?
C11 C16 . 1.407(2) ?
C12 H12 . 0.9500 ?
C12 C13 . 1.384(2) ?
C13 H13 . 0.9500 ?
C13 C14 . 1.386(2) ?
C14 H14 . 0.9500 ?
C14 C15 . 1.391(2) ?
C15 H15 . 0.9500 ?
C15 C16 . 1.378(2) ?
C16 H16 . 0.9500 ?
C17 H17A . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 0.9800 ?
O1W H1WA . 0.83(3) ?
O1W H1WB . 0.89(3) ?
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
O5 H5 O4 . 0.86(3) 1.81(3) 2.6013(15) 153(3)
O7 H7 O8 . 0.91(3) 2.29(2) 2.7673(16) 112.2(19)
O7 H7 O1W . 0.91(3) 1.90(2) 2.7301(16) 151(2)
O1W H1WA O1W 3_566 0.83(3) 2.04(3) 2.8570(13) 172(3)
O1W H1WB O4 2_565 0.89(3) 1.91(3) 2.7976(15) 178(2)
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 . . . . 1.6(2) ?
O1 C2 C11 C12 . . . . -0.35(19) ?
O1 C2 C11 C16 . . . . -179.84(13) ?
O1 C9 C10 C4 . . . . 0.3(2) ?
O1 C9 C10 C5 . . . . -179.72(13) ?
C2 O1 C9 C8 . . . . -179.33(12) ?
C2 O1 C9 C10 . . . . 0.6(2) ?
C2 C3 C4 O4 . . . . 178.77(14) ?
C2 C3 C4 C10 . . . . -0.5(2) ?
C2 C11 C12 C13 . . . . 179.52(14) ?
C2 C11 C16 C15 . . . . 179.78(14) ?
C3 C2 C11 C12 . . . . 179.48(15) ?
C3 C2 C11 C16 . . . . 0.0(2) ?
C3 C4 C10 C5 . . . . 179.68(13) ?
C3 C4 C10 C9 . . . . -0.37(19) ?
O4 C4 C10 C5 . . . . 0.4(2) ?
O4 C4 C10 C9 . . . . -179.69(14) ?
O5 C5 C6 C7 . . . . -179.45(13) ?
O5 C5 C10 C4 . . . . -0.8(2) ?
O5 C5 C10 C9 . . . . 179.26(13) ?
C5 C6 C7 O7 . . . . -178.71(14) ?
C5 C6 C7 C8 . . . . 0.2(2) ?
C6 C5 C10 C4 . . . . 179.55(13) ?
C6 C5 C10 C9 . . . . -0.4(2) ?
C6 C7 C8 O8 . . . . -177.74(13) ?
C6 C7 C8 C9 . . . . -0.3(2) ?
O7 C7 C8 O8 . . . . 1.1(2) ?
O7 C7 C8 C9 . . . . 178.54(13) ?
C7 C8 C9 O1 . . . . -179.93(12) ?
C7 C8 C9 C10 . . . . 0.1(2) ?
O8 C8 C9 O1 . . . . -2.6(2) ?
O8 C8 C9 C10 . . . . 177.47(13) ?
C8 C9 C10 C4 . . . . -179.70(14) ?
C8 C9 C10 C5 . . . . 0.2(2) ?
C9 O1 C2 C3 . . . . -1.6(2) ?
C9 O1 C2 C11 . . . . 178.23(12) ?
C10 C5 C6 C7 . . . . 0.2(2) ?
C11 C2 C3 C4 . . . . -178.24(13) ?
C11 C12 C13 C14 . . . . 0.6(2) ?
C12 C11 C16 C15 . . . . 0.3(2) ?
C12 C13 C14 C15 . . . . 0.5(2) ?
C13 C14 C15 C16 . . . . -1.2(2) ?
C14 C15 C16 C11 . . . . 0.8(2) ?
C16 C11 C12 C13 . . . . -1.0(2) ?
C17 O8 C8 C7 . . . . -99.41(17) ?
C17 O8 C8 C9 . . . . 83.26(17) ?

_cod_database_fobs_code 2022142
