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The flavonoid Oroxylin A (6-meth­oxy­chrysin or 5,7-dihydroxy-6-methoxy-2-phenyl-4H-chromen-4-one, C16H12O5) and its regioisomers are of increasing inter­est for a variety of bioactive functions and their pharmaceutical formulation is of importance. Previous difficulties in the separation and mis­identification of Oroxylin A from its regioisomers Wogonin (8-meth­oxy­chrysin or 5,7-dihydroxy-8-methoxy-2-phenyl-4H-chromen-4-one) and Negletein (5,6-dihy­droxy-7-meth­oxy­flavone or 5,6-dihydroxy-7-methoxy-2-phenyl-4H-chromen-4-one) render its full structural and powder X-ray characterization highly desirable. The low-temperature (100 K) crystal structures of Oroxylin A, Negletein and Wogonin sesquihydrate are reported for the first time. Wogonin crystallizes in two related but distinct hydrated forms. These have very similar powder diffractograms, indicating that such issues need to be addressed for its pharma­ceutical formulation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229620005550/wp3006sup1.cif
Contains datablocks val143ccult, val120cult, madiha48cult, val3h, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620005550/wp3006Val143cCuLTsup2.hkl
Contains datablock Val143cCuLT

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620005550/wp3006val143ccultsup6.hkl
Contains datablock val143ccult

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620005550/wp3006Val120CuLTsup3.hkl
Contains datablock Val120CuLT

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620005550/wp3006val120cultsup7.hkl
Contains datablock val120cult

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620005550/wp3006madiha48CuLTsup4.hkl
Contains datablock madiha48CuLT

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620005550/wp3006madiha48cultsup8.hkl
Contains datablock madiha48cult

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620005550/wp3006val3hsup5.hkl
Contains datablock val3h

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229620005550/wp3006sup9.pdf
NMR details of Wogonin sesquihydrate

CCDC references: 1998087; 1998086; 1998085; 1998084

Computing details top

For all structures, data collection: CrysAlis PRO (Rigaku OD, 2020); cell refinement: CrysAlis PRO (Rigaku OD, 2020); data reduction: CrysAlis PRO (Rigaku OD, 2020). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for val143ccult, madiha48cult, val3h; olex2.solve (Bourhis et al., 2015) for val120cult. For all structures, program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

5,7-Dihydroxy-6-methoxy-2-phenyl-4H-chromen-4-one (val143ccult) top
Crystal data top
C16H12O5F(000) = 592
Mr = 284.26Dx = 1.530 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54184 Å
a = 3.8224 (2) ÅCell parameters from 2316 reflections
b = 19.5339 (7) Åθ = 3.5–70.7°
c = 16.5360 (6) ŵ = 0.96 mm1
β = 91.604 (4)°T = 100 K
V = 1234.19 (9) Å3Block, clear light yellow
Z = 40.1 × 0.1 × 0.02 mm
Data collection top
Rigaku OD SuperNova Dual source
diffractometer with an Atlas detector
2231 independent reflections
Radiation source: micro-focus sealed X-ray tube1797 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.032
Detector resolution: 5.1788 pixels mm-1θmax = 67.5°, θmin = 3.5°
ω scansh = 43
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2020)
k = 2223
Tmin = 0.837, Tmax = 1.000l = 1918
6384 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.113 w = 1/[σ2(Fo2) + (0.0549P)2 + 0.331P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
2231 reflectionsΔρmax = 0.19 e Å3
199 parametersΔρmin = 0.19 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. The structures were solved and refined using embedded SHELX programs (Sheldrick, 2008; 2015) or internal options from within the Olex2 suite (Dolomanov et al., 2009; Bourhis et al., 2015).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.0710 (4)0.85831 (6)0.93733 (7)0.0267 (3)
C110.1867 (5)0.94300 (10)0.84057 (11)0.0282 (4)
C20.0486 (5)0.87404 (10)0.85750 (11)0.0264 (4)
O40.3429 (4)0.72141 (7)0.77398 (7)0.0335 (3)
C120.2584 (5)0.98879 (10)0.90363 (11)0.0304 (4)
H120.22240.97520.95790.036*
O50.4662 (4)0.63786 (7)0.89289 (9)0.0325 (3)
C30.0900 (5)0.82992 (10)0.80206 (11)0.0285 (4)
H30.10390.84310.74680.034*
C130.3821 (6)1.05406 (10)0.88758 (12)0.0334 (4)
H130.43041.08490.93090.040*
O60.4387 (4)0.61621 (7)1.05694 (8)0.0319 (3)
C40.2158 (5)0.76388 (10)0.82508 (11)0.0278 (4)
C140.4353 (6)1.07446 (10)0.80887 (12)0.0340 (4)
H140.51531.11950.79790.041*
C50.3225 (5)0.68599 (10)0.94187 (11)0.0272 (4)
O70.1352 (4)0.70700 (7)1.15476 (8)0.0350 (3)
C150.3709 (6)1.02868 (11)0.74573 (13)0.0382 (5)
H150.41231.04220.69170.046*
C60.3025 (5)0.67443 (10)1.02413 (11)0.0281 (4)
C160.2465 (6)0.96327 (10)0.76126 (12)0.0345 (5)
H160.20220.93230.71780.041*
C70.1492 (5)0.72355 (10)1.07638 (11)0.0284 (4)
C80.0253 (5)0.78535 (9)1.04667 (11)0.0269 (4)
H80.07460.81881.08200.032*
C90.0517 (5)0.79662 (9)0.96438 (11)0.0254 (4)
C100.1960 (5)0.74853 (10)0.90979 (11)0.0266 (4)
C170.2142 (6)0.55817 (10)1.04909 (12)0.0350 (5)
H17A0.15340.55270.99230.053*
H17B0.33510.51701.06740.053*
H17C0.00040.56511.08220.053*
H50.467 (6)0.6517 (12)0.8461 (15)0.025 (5)*
H70.022 (9)0.7401 (18)1.186 (2)0.063 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0373 (7)0.0201 (6)0.0226 (6)0.0005 (5)0.0007 (5)0.0004 (5)
C110.0322 (10)0.0240 (9)0.0283 (9)0.0036 (7)0.0018 (7)0.0003 (7)
C20.0324 (9)0.0238 (9)0.0230 (8)0.0049 (7)0.0004 (7)0.0004 (7)
O40.0507 (9)0.0253 (7)0.0244 (6)0.0008 (6)0.0038 (6)0.0038 (5)
C120.0373 (10)0.0260 (10)0.0279 (9)0.0026 (8)0.0004 (8)0.0008 (7)
O50.0450 (8)0.0252 (7)0.0271 (7)0.0039 (6)0.0036 (6)0.0024 (5)
C30.0394 (11)0.0250 (10)0.0210 (8)0.0030 (8)0.0003 (7)0.0001 (7)
C130.0412 (11)0.0245 (10)0.0343 (10)0.0020 (8)0.0039 (8)0.0031 (8)
O60.0380 (8)0.0235 (7)0.0345 (7)0.0017 (5)0.0044 (6)0.0025 (5)
C40.0336 (10)0.0253 (9)0.0242 (9)0.0039 (7)0.0024 (7)0.0035 (7)
C140.0413 (11)0.0216 (9)0.0391 (11)0.0009 (8)0.0013 (8)0.0036 (8)
C50.0283 (9)0.0232 (9)0.0300 (9)0.0023 (7)0.0004 (7)0.0026 (7)
O70.0510 (9)0.0302 (7)0.0237 (7)0.0048 (6)0.0020 (6)0.0028 (5)
C150.0533 (13)0.0304 (11)0.0307 (10)0.0031 (9)0.0009 (9)0.0068 (8)
C60.0313 (10)0.0225 (9)0.0305 (9)0.0016 (7)0.0029 (7)0.0007 (7)
C160.0502 (12)0.0272 (10)0.0261 (9)0.0006 (8)0.0012 (8)0.0009 (7)
C70.0331 (10)0.0271 (9)0.0249 (9)0.0035 (7)0.0007 (7)0.0003 (7)
C80.0326 (10)0.0223 (9)0.0255 (9)0.0018 (7)0.0020 (7)0.0027 (7)
C90.0292 (9)0.0212 (9)0.0259 (9)0.0037 (7)0.0008 (7)0.0002 (7)
C100.0290 (9)0.0238 (9)0.0268 (9)0.0041 (7)0.0002 (7)0.0012 (7)
C170.0471 (12)0.0223 (10)0.0357 (10)0.0011 (8)0.0027 (9)0.0013 (8)
Geometric parameters (Å, º) top
O1—C21.356 (2)C14—H140.9500
O1—C91.373 (2)C14—C151.391 (3)
C11—C21.476 (3)C5—C61.379 (3)
C11—C121.395 (3)C5—C101.422 (3)
C11—C161.395 (3)O7—C71.335 (2)
C2—C31.355 (3)O7—H70.93 (4)
O4—C41.271 (2)C15—H150.9500
C12—H120.9500C15—C161.390 (3)
C12—C131.388 (3)C6—C71.408 (3)
O5—C51.348 (2)C16—H160.9500
O5—H50.82 (3)C7—C81.392 (3)
C3—H30.9500C8—H80.9500
C3—C41.432 (3)C8—C91.379 (3)
C13—H130.9500C9—C101.405 (3)
C13—C141.382 (3)C17—H17A0.9800
O6—C61.369 (2)C17—H17B0.9800
O6—C171.430 (2)C17—H17C0.9800
C4—C101.432 (3)
C2—O1—C9120.22 (14)C14—C15—H15119.8
C12—C11—C2120.47 (17)C16—C15—C14120.43 (19)
C16—C11—C2120.40 (17)C16—C15—H15119.8
C16—C11—C12119.13 (18)O6—C6—C5121.03 (17)
O1—C2—C11112.22 (15)O6—C6—C7118.64 (16)
C3—C2—O1121.83 (17)C5—C6—C7120.31 (18)
C3—C2—C11125.95 (17)C11—C16—H16120.0
C11—C12—H12119.8C15—C16—C11120.04 (18)
C13—C12—C11120.46 (18)C15—C16—H16120.0
C13—C12—H12119.8O7—C7—C6115.80 (17)
C5—O5—H5109.1 (16)O7—C7—C8123.23 (17)
C2—C3—H3119.3C8—C7—C6120.96 (17)
C2—C3—C4121.40 (17)C7—C8—H8121.0
C4—C3—H3119.3C9—C8—C7118.07 (17)
C12—C13—H13119.8C9—C8—H8121.0
C14—C13—C12120.33 (18)O1—C9—C8116.44 (16)
C14—C13—H13119.8O1—C9—C10120.62 (16)
C6—O6—C17112.76 (15)C8—C9—C10122.94 (17)
O4—C4—C3122.42 (17)C5—C10—C4122.36 (17)
O4—C4—C10121.50 (18)C9—C10—C4119.83 (17)
C3—C4—C10116.07 (16)C9—C10—C5117.80 (16)
C13—C14—H14120.2O6—C17—H17A109.5
C13—C14—C15119.60 (19)O6—C17—H17B109.5
C15—C14—H14120.2O6—C17—H17C109.5
O5—C5—C6119.28 (17)H17A—C17—H17B109.5
O5—C5—C10120.82 (16)H17A—C17—H17C109.5
C6—C5—C10119.90 (17)H17B—C17—H17C109.5
C7—O7—H7112 (2)
O1—C2—C3—C40.8 (3)C13—C14—C15—C161.4 (3)
O1—C9—C10—C40.0 (3)O6—C6—C7—O73.2 (3)
O1—C9—C10—C5179.20 (16)O6—C6—C7—C8176.22 (17)
C11—C2—C3—C4179.81 (18)C14—C15—C16—C110.3 (3)
C11—C12—C13—C140.1 (3)C5—C6—C7—O7178.60 (18)
C2—O1—C9—C8178.71 (16)C5—C6—C7—C82.0 (3)
C2—O1—C9—C101.2 (3)O7—C7—C8—C9179.61 (18)
C2—C11—C12—C13178.80 (18)C6—C5—C10—C4178.83 (19)
C2—C11—C16—C15178.91 (19)C6—C5—C10—C90.3 (3)
C2—C3—C4—O4179.13 (19)C6—C7—C8—C91.1 (3)
C2—C3—C4—C101.9 (3)C16—C11—C2—O1167.96 (18)
O4—C4—C10—C51.3 (3)C16—C11—C2—C312.6 (3)
O4—C4—C10—C9179.58 (17)C16—C11—C12—C131.1 (3)
C12—C11—C2—O112.2 (3)C7—C8—C9—O1179.58 (16)
C12—C11—C2—C3167.2 (2)C7—C8—C9—C100.3 (3)
C12—C11—C16—C151.0 (3)C8—C9—C10—C4179.82 (18)
C12—C13—C14—C151.3 (3)C8—C9—C10—C50.7 (3)
O5—C5—C6—O62.7 (3)C9—O1—C2—C11178.71 (15)
O5—C5—C6—C7179.13 (17)C9—O1—C2—C30.7 (3)
O5—C5—C10—C40.4 (3)C10—C5—C6—O6176.59 (16)
O5—C5—C10—C9179.55 (17)C10—C5—C6—C71.6 (3)
C3—C4—C10—C5177.72 (17)C17—O6—C6—C579.6 (2)
C3—C4—C10—C91.4 (3)C17—O6—C6—C7102.1 (2)
5,6-Dihydroxy-7-methoxy-2-phenyl-4H-chromen-4-one (val120cult) top
Crystal data top
C16H12O5F(000) = 592
Mr = 284.26Dx = 1.466 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
a = 9.78509 (13) ÅCell parameters from 4050 reflections
b = 15.8032 (2) Åθ = 4.5–72.5°
c = 8.33104 (11) ŵ = 0.92 mm1
β = 91.3453 (11)°T = 100 K
V = 1287.92 (3) Å3Needle, clear whiteish yellow
Z = 40.2 × 0.1 × 0.1 mm
Data collection top
Rigaku OD SuperNova Dual source
diffractometer with an Atlas detector
2329 independent reflections
Radiation source: micro-focus sealed X-ray tube2073 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.017
Detector resolution: 10.3577 pixels mm-1θmax = 68.0°, θmin = 4.5°
ω scansh = 1111
Absorption correction: multi-scan
(CrysAlis PRO: Rigaku OD, 2020)
k = 1518
Tmin = 0.764, Tmax = 1.000l = 99
7020 measured reflections
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.030 w = 1/[σ2(Fo2) + (0.0397P)2 + 0.416P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.079(Δ/σ)max < 0.001
S = 1.00Δρmax = 0.20 e Å3
2329 reflectionsΔρmin = 0.17 e Å3
200 parametersExtinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0018 (3)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. The structures were solved and refined using embedded SHELX programs (Sheldrick, 2008; 2015) or internal options from within the Olex2 suite (Dolomanov et al., 2009; Bourhis et al., 2015).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.35638 (8)0.36946 (5)0.31509 (9)0.0179 (2)
C20.23257 (11)0.40587 (7)0.28256 (13)0.0170 (2)
C30.17172 (11)0.45781 (7)0.38872 (14)0.0194 (3)
H30.08410.48060.36280.023*
O40.18595 (8)0.52927 (5)0.63906 (10)0.0229 (2)
C40.23687 (11)0.47912 (7)0.53970 (13)0.0180 (2)
O50.39369 (9)0.50619 (5)0.82813 (9)0.0214 (2)
H50.309 (2)0.5233 (13)0.782 (2)0.064 (6)*
C50.44147 (12)0.45137 (7)0.71706 (13)0.0174 (2)
O60.63767 (9)0.41813 (6)0.88626 (10)0.0242 (2)
H60.599 (2)0.4507 (12)0.952 (2)0.054 (6)*
C60.56201 (12)0.40888 (7)0.74836 (13)0.0188 (2)
O70.73099 (9)0.31461 (5)0.67570 (10)0.0269 (2)
C70.61241 (11)0.35288 (7)0.63173 (14)0.0197 (3)
C80.54327 (12)0.34008 (7)0.48629 (14)0.0193 (3)
H80.57830.30290.40750.023*
C90.42139 (11)0.38330 (7)0.45978 (13)0.0166 (2)
C100.36711 (11)0.43830 (7)0.57208 (13)0.0168 (2)
C110.18037 (12)0.38185 (7)0.12189 (13)0.0176 (2)
C120.26478 (12)0.33922 (7)0.01501 (14)0.0205 (3)
H120.35530.32420.04750.025*
C130.21661 (13)0.31889 (7)0.13807 (14)0.0229 (3)
H130.27410.28970.20980.027*
C140.08494 (13)0.34091 (8)0.18687 (14)0.0237 (3)
H140.05290.32760.29240.028*
C150.00004 (12)0.38244 (7)0.08137 (14)0.0226 (3)
H150.09060.39700.11440.027*
C160.04708 (12)0.40260 (7)0.07203 (14)0.0197 (3)
H160.01160.43080.14390.024*
C170.79121 (14)0.25907 (9)0.56115 (18)0.0372 (4)
H17A0.87350.23310.60890.056*
H17B0.81570.29140.46570.056*
H17C0.72560.21470.53060.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0157 (4)0.0207 (4)0.0171 (4)0.0019 (3)0.0052 (3)0.0025 (3)
C20.0144 (5)0.0175 (6)0.0190 (6)0.0009 (4)0.0035 (4)0.0027 (4)
C30.0151 (5)0.0232 (6)0.0195 (6)0.0016 (4)0.0038 (4)0.0014 (4)
O40.0199 (4)0.0288 (5)0.0198 (4)0.0054 (3)0.0023 (3)0.0048 (3)
C40.0167 (5)0.0197 (6)0.0177 (6)0.0001 (4)0.0003 (4)0.0011 (4)
O50.0206 (4)0.0270 (5)0.0163 (4)0.0054 (3)0.0041 (3)0.0052 (3)
C50.0186 (6)0.0177 (5)0.0157 (5)0.0006 (4)0.0008 (4)0.0006 (4)
O60.0244 (5)0.0295 (5)0.0181 (4)0.0082 (4)0.0097 (3)0.0062 (4)
C60.0198 (6)0.0201 (6)0.0163 (5)0.0003 (4)0.0056 (4)0.0007 (4)
O70.0241 (5)0.0287 (5)0.0272 (5)0.0123 (4)0.0128 (4)0.0103 (4)
C70.0167 (6)0.0186 (6)0.0235 (6)0.0027 (4)0.0054 (4)0.0003 (4)
C80.0191 (6)0.0190 (6)0.0196 (6)0.0019 (4)0.0029 (4)0.0039 (4)
C90.0168 (5)0.0177 (5)0.0152 (5)0.0026 (4)0.0042 (4)0.0001 (4)
C100.0159 (5)0.0170 (5)0.0173 (5)0.0010 (4)0.0020 (4)0.0015 (4)
C110.0197 (6)0.0154 (5)0.0175 (6)0.0033 (4)0.0040 (4)0.0028 (4)
C120.0213 (6)0.0193 (6)0.0208 (6)0.0004 (4)0.0038 (4)0.0014 (4)
C130.0299 (7)0.0202 (6)0.0185 (6)0.0015 (5)0.0012 (5)0.0006 (4)
C140.0313 (7)0.0220 (6)0.0175 (6)0.0080 (5)0.0080 (5)0.0021 (4)
C150.0212 (6)0.0226 (6)0.0237 (6)0.0043 (5)0.0074 (5)0.0054 (5)
C160.0188 (6)0.0198 (6)0.0203 (6)0.0028 (4)0.0033 (4)0.0019 (4)
C170.0297 (7)0.0383 (8)0.0429 (8)0.0179 (6)0.0170 (6)0.0226 (6)
Geometric parameters (Å, º) top
O1—C21.3626 (13)O7—C71.3514 (14)
O1—C91.3674 (13)O7—C171.4334 (15)
C2—C31.3547 (16)C7—C81.3885 (16)
C2—C111.4713 (15)C8—C91.3876 (16)
C3—C41.4367 (16)C9—C101.3914 (16)
O4—C41.2573 (14)C11—C121.4012 (16)
C4—C101.4480 (15)C11—C161.3984 (16)
O5—C51.3586 (14)C12—C131.3869 (17)
C5—C61.3768 (16)C13—C141.3863 (18)
C5—C101.4105 (16)C14—C151.3889 (18)
O6—C61.3599 (13)C15—C161.3856 (16)
C6—C71.4118 (16)
C2—O1—C9120.06 (9)C8—C7—C6121.40 (10)
O1—C2—C11111.10 (9)C9—C8—C7117.80 (10)
C3—C2—O1121.90 (10)O1—C9—C8116.22 (10)
C3—C2—C11126.99 (10)O1—C9—C10121.04 (10)
C2—C3—C4121.38 (10)C8—C9—C10122.73 (10)
C3—C4—C10115.42 (10)C5—C10—C4121.89 (10)
O4—C4—C3123.33 (10)C9—C10—C4120.08 (10)
O4—C4—C10121.25 (10)C9—C10—C5118.02 (10)
O5—C5—C6119.27 (10)C12—C11—C2120.33 (10)
O5—C5—C10119.85 (10)C16—C11—C2120.74 (10)
C6—C5—C10120.88 (10)C16—C11—C12118.92 (10)
C5—C6—C7119.13 (10)C13—C12—C11120.20 (11)
O6—C6—C5123.68 (10)C14—C13—C12120.33 (11)
O6—C6—C7117.18 (10)C13—C14—C15119.94 (11)
C7—O7—C17117.21 (9)C16—C15—C14120.08 (11)
O7—C7—C6113.92 (10)C15—C16—C11120.52 (11)
O7—C7—C8124.68 (10)
O1—C2—C3—C41.84 (17)O6—C6—C7—O70.79 (15)
O1—C2—C11—C1210.02 (14)O6—C6—C7—C8179.17 (10)
O1—C2—C11—C16171.33 (10)C6—C5—C10—C4176.98 (10)
O1—C9—C10—C42.72 (16)C6—C5—C10—C91.99 (16)
O1—C9—C10—C5178.30 (10)C6—C7—C8—C90.92 (17)
C2—O1—C9—C8176.54 (9)O7—C7—C8—C9179.13 (11)
C2—O1—C9—C103.85 (15)C7—C8—C9—O1179.74 (10)
C2—C3—C4—O4177.53 (11)C7—C8—C9—C100.13 (17)
C2—C3—C4—C102.79 (16)C8—C9—C10—C4177.69 (10)
C2—C11—C12—C13178.07 (10)C8—C9—C10—C51.29 (17)
C2—C11—C16—C15177.74 (10)C9—O1—C2—C31.57 (16)
C3—C2—C11—C12169.12 (11)C9—O1—C2—C11179.25 (9)
C3—C2—C11—C169.54 (18)C10—C5—C6—O6179.38 (10)
C3—C4—C10—C5178.39 (10)C10—C5—C6—C71.25 (17)
C3—C4—C10—C90.55 (16)C11—C2—C3—C4177.21 (11)
O4—C4—C10—C51.29 (17)C11—C12—C13—C140.33 (17)
O4—C4—C10—C9179.76 (10)C12—C11—C16—C150.93 (17)
O5—C5—C6—O60.27 (17)C12—C13—C14—C150.95 (18)
O5—C5—C6—C7179.10 (10)C13—C14—C15—C160.62 (18)
O5—C5—C10—C42.67 (17)C14—C15—C16—C110.32 (17)
O5—C5—C10—C9178.36 (10)C16—C11—C12—C130.60 (17)
C5—C6—C7—O7179.80 (10)C17—O7—C7—C6177.82 (11)
C5—C6—C7—C80.24 (18)C17—O7—C7—C82.14 (18)
5,7-Dihydroxy-8-methoxy-2-phenyl-4H-chromen-4-one monohydrate (madiha48cult) top
Crystal data top
C16H12O5·H2ODx = 1.436 Mg m3
Mr = 302.27Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P212121Cell parameters from 3063 reflections
a = 4.64835 (6) Åθ = 5.9–75.5°
b = 16.4123 (2) ŵ = 0.94 mm1
c = 18.3290 (3) ÅT = 100 K
V = 1398.32 (3) Å3Block, yellow
Z = 40.3 × 0.3 × 0.15 mm
F(000) = 632
Data collection top
Rigaku OD SuperNova Dual source
diffractometer with an Atlas detector
2486 independent reflections
Radiation source: micro-focus sealed X-ray tube2433 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.011
Detector resolution: 10.3577 pixels mm-1θmax = 67.5°, θmin = 7.2°
ω scansh = 35
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2020)
k = 1913
Tmin = 0.884, Tmax = 1.000l = 2121
3792 measured reflections
Refinement top
Refinement on F2H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.038P)2 + 0.130P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.022(Δ/σ)max < 0.001
wR(F2) = 0.059Δρmax = 0.14 e Å3
S = 1.03Δρmin = 0.13 e Å3
2486 reflectionsExtinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
217 parametersExtinction coefficient: 0.0038 (5)
0 restraintsAbsolute structure: Flack x determined using 964 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Hydrogen site location: mixedAbsolute structure parameter: 0.05 (6)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. The structures were solved and refined using embedded SHELX programs (Sheldrick, 2008; 2015) or internal options from within the Olex2 suite (Dolomanov et al., 2009; Bourhis et al., 2015).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.5540 (2)0.57179 (6)0.22376 (5)0.0159 (2)
C20.6132 (3)0.53999 (9)0.15689 (8)0.0158 (3)
C30.4816 (3)0.47174 (9)0.13186 (8)0.0170 (3)
H30.53270.45080.08530.020*
O40.1384 (2)0.36789 (6)0.15132 (6)0.0203 (3)
C40.2671 (3)0.43068 (9)0.17412 (8)0.0163 (3)
O50.1549 (2)0.36529 (7)0.27217 (6)0.0213 (3)
H50.086 (6)0.3513 (17)0.2306 (16)0.056 (8)*
C50.0049 (3)0.43234 (9)0.29236 (8)0.0168 (3)
C60.0574 (3)0.46767 (10)0.35926 (8)0.0178 (3)
H60.19680.44480.39120.021*
O70.0424 (3)0.56936 (7)0.44646 (6)0.0212 (3)
H70.163 (5)0.6117 (15)0.4551 (13)0.039 (6)*
C70.0955 (3)0.53744 (9)0.38004 (8)0.0170 (3)
O80.4543 (2)0.63908 (6)0.35711 (6)0.0189 (2)
C80.3008 (3)0.57230 (9)0.33407 (8)0.0162 (3)
C90.3508 (3)0.53563 (9)0.26700 (8)0.0148 (3)
C100.2027 (3)0.46562 (9)0.24440 (8)0.0153 (3)
C110.8294 (3)0.58814 (9)0.11764 (8)0.0161 (3)
C120.9489 (3)0.65811 (10)0.14900 (8)0.0193 (3)
H120.88850.67500.19620.023*
C131.1543 (3)0.70295 (10)0.11190 (9)0.0217 (3)
H131.23540.75010.13390.026*
C141.2420 (3)0.67930 (10)0.04282 (9)0.0217 (3)
H141.38420.70990.01760.026*
C151.1213 (3)0.61064 (10)0.01052 (9)0.0214 (3)
H151.17880.59510.03720.026*
C160.9188 (3)0.56505 (10)0.04729 (8)0.0193 (3)
H160.83940.51790.02500.023*
C170.3416 (4)0.71412 (10)0.32867 (10)0.0273 (4)
H17A0.36390.71490.27550.041*
H17B0.44680.76010.35000.041*
H17C0.13720.71860.34110.041*
O1W0.2807 (3)0.70168 (7)0.51350 (6)0.0214 (3)
H1WA0.430 (7)0.7262 (16)0.5025 (16)0.055 (8)*
H1WB0.312 (5)0.6794 (13)0.5572 (14)0.037 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0176 (5)0.0176 (5)0.0125 (5)0.0004 (4)0.0014 (4)0.0007 (4)
C20.0152 (7)0.0197 (7)0.0127 (7)0.0042 (6)0.0022 (6)0.0008 (6)
C30.0183 (7)0.0190 (7)0.0136 (7)0.0022 (6)0.0003 (6)0.0009 (5)
O40.0248 (5)0.0173 (5)0.0186 (5)0.0019 (5)0.0007 (4)0.0034 (4)
C40.0176 (7)0.0148 (7)0.0164 (7)0.0045 (6)0.0029 (6)0.0005 (6)
O50.0273 (6)0.0184 (5)0.0182 (6)0.0055 (5)0.0020 (5)0.0009 (4)
C50.0187 (7)0.0143 (7)0.0174 (7)0.0021 (6)0.0024 (6)0.0016 (6)
C60.0190 (6)0.0196 (7)0.0148 (7)0.0003 (6)0.0014 (6)0.0032 (5)
O70.0279 (6)0.0227 (6)0.0129 (5)0.0025 (5)0.0040 (4)0.0021 (4)
C70.0204 (7)0.0180 (7)0.0126 (7)0.0038 (6)0.0008 (6)0.0010 (6)
O80.0232 (5)0.0170 (5)0.0167 (5)0.0013 (5)0.0025 (4)0.0015 (4)
C80.0189 (7)0.0145 (7)0.0152 (7)0.0024 (6)0.0015 (6)0.0009 (6)
C90.0144 (7)0.0151 (7)0.0149 (7)0.0020 (6)0.0008 (6)0.0035 (5)
C100.0172 (7)0.0153 (7)0.0134 (7)0.0039 (6)0.0013 (6)0.0014 (5)
C110.0142 (6)0.0181 (7)0.0158 (7)0.0039 (5)0.0021 (6)0.0016 (6)
C120.0207 (7)0.0219 (7)0.0151 (7)0.0013 (6)0.0005 (6)0.0005 (6)
C130.0215 (7)0.0202 (7)0.0235 (8)0.0015 (6)0.0016 (7)0.0004 (6)
C140.0185 (7)0.0243 (8)0.0224 (8)0.0020 (6)0.0029 (6)0.0064 (6)
C150.0222 (8)0.0256 (7)0.0163 (7)0.0049 (6)0.0037 (6)0.0006 (6)
C160.0190 (7)0.0216 (7)0.0172 (7)0.0022 (6)0.0002 (6)0.0003 (6)
C170.0395 (10)0.0160 (8)0.0265 (9)0.0011 (7)0.0059 (8)0.0001 (6)
O1W0.0249 (6)0.0235 (6)0.0157 (6)0.0014 (5)0.0010 (5)0.0025 (5)
Geometric parameters (Å, º) top
O1—C21.3602 (18)C8—C91.388 (2)
O1—C91.3682 (18)C9—C101.402 (2)
C2—C31.356 (2)C11—C121.399 (2)
C2—C111.467 (2)C11—C161.407 (2)
C3—H30.9500C12—H120.9500
C3—C41.431 (2)C12—C131.384 (2)
O4—C41.2626 (19)C13—H130.9500
C4—C101.442 (2)C13—C141.386 (2)
O5—H50.86 (3)C14—H140.9500
O5—C51.3540 (19)C14—C151.391 (2)
C5—C61.378 (2)C15—H150.9500
C5—C101.415 (2)C15—C161.378 (2)
C6—H60.9500C16—H160.9500
C6—C71.401 (2)C17—H17A0.9800
O7—H70.91 (3)C17—H17B0.9800
O7—C71.3481 (18)C17—H17C0.9800
C7—C81.396 (2)O1W—H1WA0.83 (3)
O8—C81.3743 (19)O1W—H1WB0.89 (3)
O8—C171.4363 (19)
C2—O1—C9119.69 (12)C5—C10—C4122.89 (14)
O1—C2—C11111.96 (12)C9—C10—C4119.22 (14)
C3—C2—O1122.02 (14)C9—C10—C5117.89 (13)
C3—C2—C11126.01 (14)C12—C11—C2120.83 (14)
C2—C3—H3119.3C12—C11—C16118.70 (14)
C2—C3—C4121.34 (14)C16—C11—C2120.47 (14)
C4—C3—H3119.3C11—C12—H12119.7
C3—C4—C10116.17 (14)C13—C12—C11120.56 (14)
O4—C4—C3122.36 (14)C13—C12—H12119.7
O4—C4—C10121.47 (14)C12—C13—H13119.9
C5—O5—H5105.6 (19)C12—C13—C14120.20 (15)
O5—C5—C6119.60 (14)C14—C13—H13119.9
O5—C5—C10119.67 (13)C13—C14—H14120.1
C6—C5—C10120.72 (14)C13—C14—C15119.80 (15)
C5—C6—H6120.1C15—C14—H14120.1
C5—C6—C7119.75 (14)C14—C15—H15119.8
C7—C6—H6120.1C16—C15—C14120.47 (15)
C7—O7—H7110.1 (16)C16—C15—H15119.8
O7—C7—C6118.06 (13)C11—C16—H16119.9
O7—C7—C8120.73 (14)C15—C16—C11120.25 (15)
C8—C7—C6121.20 (14)C15—C16—H16119.9
C8—O8—C17112.52 (12)O8—C17—H17A109.5
O8—C8—C7119.77 (13)O8—C17—H17B109.5
O8—C8—C9122.06 (13)O8—C17—H17C109.5
C9—C8—C7118.12 (14)H17A—C17—H17B109.5
O1—C9—C8116.14 (13)H17A—C17—H17C109.5
O1—C9—C10121.54 (13)H17B—C17—H17C109.5
C8—C9—C10122.32 (14)H1WA—O1W—H1WB106 (3)
O1—C2—C3—C41.6 (2)C6—C5—C10—C90.4 (2)
O1—C2—C11—C120.35 (19)C6—C7—C8—O8177.74 (13)
O1—C2—C11—C16179.84 (13)C6—C7—C8—C90.3 (2)
O1—C9—C10—C40.3 (2)O7—C7—C8—O81.1 (2)
O1—C9—C10—C5179.72 (13)O7—C7—C8—C9178.54 (13)
C2—O1—C9—C8179.33 (12)C7—C8—C9—O1179.93 (12)
C2—O1—C9—C100.6 (2)C7—C8—C9—C100.1 (2)
C2—C3—C4—O4178.77 (14)O8—C8—C9—O12.6 (2)
C2—C3—C4—C100.5 (2)O8—C8—C9—C10177.47 (13)
C2—C11—C12—C13179.52 (14)C8—C9—C10—C4179.70 (14)
C2—C11—C16—C15179.78 (14)C8—C9—C10—C50.2 (2)
C3—C2—C11—C12179.48 (15)C9—O1—C2—C31.6 (2)
C3—C2—C11—C160.0 (2)C9—O1—C2—C11178.23 (12)
C3—C4—C10—C5179.68 (13)C10—C5—C6—C70.2 (2)
C3—C4—C10—C90.37 (19)C11—C2—C3—C4178.24 (13)
O4—C4—C10—C50.4 (2)C11—C12—C13—C140.6 (2)
O4—C4—C10—C9179.69 (14)C12—C11—C16—C150.3 (2)
O5—C5—C6—C7179.45 (13)C12—C13—C14—C150.5 (2)
O5—C5—C10—C40.8 (2)C13—C14—C15—C161.2 (2)
O5—C5—C10—C9179.26 (13)C14—C15—C16—C110.8 (2)
C5—C6—C7—O7178.71 (14)C16—C11—C12—C131.0 (2)
C5—C6—C7—C80.2 (2)C17—O8—C8—C799.41 (17)
C6—C5—C10—C4179.55 (13)C17—O8—C8—C983.26 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5···O40.86 (3)1.81 (3)2.6013 (15)153 (3)
O7—H7···O80.91 (3)2.29 (2)2.7673 (16)112.2 (19)
O7—H7···O1W0.91 (3)1.90 (2)2.7301 (16)151 (2)
O1W—H1WA···O1Wi0.83 (3)2.04 (3)2.8570 (13)172 (3)
O1W—H1WB···O4ii0.89 (3)1.91 (3)2.7976 (15)178 (2)
Symmetry codes: (i) x+1/2, y+3/2, z+1; (ii) x+1/2, y+1, z+1/2.
5,7-Dihydroxy-8-methoxy-2-phenyl-4H-chromen-4-one 1.25-hydrate (val3h) top
Crystal data top
C16H12O5·1.25H2OF(000) = 642
Mr = 306.78Dx = 1.477 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54184 Å
a = 4.39382 (9) ÅCell parameters from 4183 reflections
b = 18.7848 (3) Åθ = 3.5–74.3°
c = 16.8308 (3) ŵ = 0.97 mm1
β = 96.5918 (19)°T = 100 K
V = 1379.98 (5) Å3Plate, yellow
Z = 40.4 × 0.08 × 0.05 mm
Data collection top
Rigaku OD SuperNova Dual source
diffractometer with an Atlas detector
Rint = 0.019
ω scansθmax = 67.5°, θmin = 7.1°
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2020)
h = 35
Tmin = 0.818, Tmax = 1.000k = 2122
7256 measured reflectionsl = 2020
2416 independent reflections3 standard reflections every 30 min
2173 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.113 w = 1/[σ2(Fo2) + (0.0532P)2 + 0.643P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
2416 reflectionsΔρmax = 0.29 e Å3
223 parametersΔρmin = 0.26 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. The structures were solved and refined using embedded SHELX programs (Sheldrick, 2008; 2015) or internal options from within the Olex2 suite (Dolomanov et al., 2009; Bourhis et al., 2015).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.5558 (2)0.76190 (5)0.18290 (6)0.0235 (3)
O40.2880 (3)0.84255 (8)0.38900 (7)0.0502 (4)
O50.0181 (3)0.72740 (9)0.40586 (8)0.0547 (4)
H50.01710.77120.41100.082*
O70.0203 (4)0.54743 (7)0.21340 (9)0.0601 (5)
H70.08470.53930.16920.090*
O80.4021 (3)0.62888 (6)0.12845 (6)0.0360 (3)
C20.6428 (3)0.82849 (8)0.20820 (9)0.0257 (3)
C30.5591 (4)0.85584 (9)0.27672 (10)0.0324 (4)
H30.62780.90210.29310.039*
C40.3708 (4)0.81719 (9)0.32510 (9)0.0322 (4)
C50.0852 (4)0.70379 (10)0.33789 (10)0.0362 (4)
C60.0029 (4)0.63732 (11)0.30907 (11)0.0414 (5)
H60.12350.60780.33730.050*
C70.1051 (4)0.61308 (9)0.23829 (10)0.0380 (4)
C80.2905 (4)0.65540 (8)0.19546 (9)0.0284 (3)
C90.3729 (3)0.72211 (8)0.22582 (8)0.0230 (3)
C100.2746 (3)0.74783 (9)0.29687 (9)0.0281 (3)
C170.2384 (5)0.65378 (9)0.05454 (10)0.0372 (4)
H17A0.01990.64310.05400.056*
H17B0.31770.62990.00940.056*
H17C0.26650.70530.05000.056*
C110.8273 (3)0.86362 (8)0.15237 (11)0.0306 (4)
C120.8860 (4)0.82958 (9)0.08227 (11)0.0350 (4)
H120.80470.78340.07060.042*
C131.0614 (4)0.86210 (11)0.02931 (13)0.0453 (5)
H131.10040.83820.01820.054*
C141.1796 (4)0.92934 (12)0.04586 (15)0.0524 (6)
H141.30200.95160.01000.063*
C151.1187 (4)0.96427 (11)0.11507 (16)0.0554 (6)
H151.19741.01080.12590.066*
C160.9449 (4)0.93205 (9)0.16824 (13)0.0425 (5)
H160.90530.95630.21550.051*
O1W0.2844 (10)0.47744 (16)0.0807 (2)0.0736 (11)0.5
H1WA0.33950.47940.03280.110*0.5
H1WB0.27180.43210.09060.110*0.5
O2W0.9631 (8)0.48649 (13)0.07684 (15)0.0452 (7)0.5
H2WA1.04540.49530.03330.068*0.5
H2WB0.77860.47200.06020.068*0.5
O3W0.3848 (16)0.5034 (3)0.0616 (4)0.0568 (15)0.25
H3WA0.46660.46180.06700.085*0.25
H3WB0.22560.50420.09740.085*0.25
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0265 (5)0.0189 (5)0.0249 (5)0.0014 (4)0.0026 (4)0.0038 (4)
O40.0599 (8)0.0635 (9)0.0253 (6)0.0337 (7)0.0040 (5)0.0164 (6)
O50.0568 (8)0.0797 (10)0.0310 (7)0.0364 (8)0.0201 (6)0.0209 (7)
O70.0895 (12)0.0323 (7)0.0521 (9)0.0260 (7)0.0197 (8)0.0205 (6)
O80.0628 (8)0.0210 (5)0.0225 (6)0.0056 (5)0.0031 (5)0.0018 (4)
C20.0205 (7)0.0195 (7)0.0347 (8)0.0045 (5)0.0068 (6)0.0034 (6)
C30.0313 (8)0.0263 (8)0.0366 (9)0.0090 (6)0.0088 (6)0.0120 (6)
C40.0320 (8)0.0401 (9)0.0224 (7)0.0180 (7)0.0060 (6)0.0083 (6)
C50.0306 (8)0.0525 (11)0.0257 (8)0.0168 (7)0.0038 (6)0.0146 (7)
C60.0338 (9)0.0520 (11)0.0383 (10)0.0034 (8)0.0028 (7)0.0253 (8)
C70.0432 (9)0.0317 (9)0.0353 (9)0.0054 (7)0.0120 (7)0.0146 (7)
C80.0381 (8)0.0234 (7)0.0219 (7)0.0003 (6)0.0039 (6)0.0029 (6)
C90.0237 (7)0.0239 (7)0.0204 (7)0.0032 (5)0.0013 (5)0.0020 (6)
C100.0256 (7)0.0372 (8)0.0203 (7)0.0117 (6)0.0023 (6)0.0013 (6)
C170.0613 (11)0.0260 (8)0.0226 (8)0.0032 (7)0.0022 (7)0.0023 (6)
C110.0190 (7)0.0250 (8)0.0454 (9)0.0036 (6)0.0064 (6)0.0043 (7)
C120.0252 (8)0.0330 (9)0.0473 (10)0.0007 (6)0.0055 (7)0.0049 (7)
C130.0276 (8)0.0525 (11)0.0565 (12)0.0022 (8)0.0074 (8)0.0178 (9)
C140.0252 (8)0.0527 (12)0.0767 (15)0.0059 (8)0.0053 (9)0.0348 (11)
C150.0375 (10)0.0358 (10)0.0860 (17)0.0124 (8)0.0219 (10)0.0247 (11)
C160.0352 (9)0.0259 (8)0.0617 (12)0.0033 (7)0.0148 (8)0.0066 (8)
O1W0.134 (4)0.0287 (15)0.062 (2)0.0152 (18)0.027 (2)0.0054 (13)
O2W0.084 (2)0.0237 (12)0.0266 (12)0.0049 (12)0.0021 (12)0.0031 (9)
O3W0.062 (4)0.042 (3)0.069 (4)0.010 (3)0.015 (3)0.010 (3)
Geometric parameters (Å, º) top
O1—C21.3619 (18)C17—H17A0.9800
O1—C91.3637 (18)C17—H17B0.9800
O4—C41.267 (2)C17—H17C0.9800
O5—H50.8400C11—C121.392 (3)
O5—C51.353 (2)C11—C161.400 (2)
O7—H70.8400C12—H120.9500
O7—C71.341 (2)C12—C131.385 (3)
O8—C81.374 (2)C13—H130.9500
O8—C171.442 (2)C13—C141.382 (3)
C2—C31.351 (2)C14—H140.9500
C2—C111.467 (2)C14—C151.389 (4)
C3—H30.9500C15—H150.9500
C3—C41.425 (3)C15—C161.381 (3)
C4—C101.434 (2)C16—H160.9500
C5—C61.373 (3)O1W—H1WA0.8699
C5—C101.409 (2)O1W—H1WB0.8700
C6—H60.9500O2W—H2WA0.8691
C6—C71.397 (3)O2W—H2WB0.8704
C7—C81.397 (2)O3W—H3WA0.8701
C8—C91.386 (2)O3W—H3WB0.8699
C9—C101.403 (2)
C2—O1—C9119.93 (12)C9—C10—C4119.18 (15)
C5—O5—H5109.5C9—C10—C5118.18 (15)
C7—O7—H7109.5O8—C17—H17A109.5
C8—O8—C17113.64 (13)O8—C17—H17B109.5
O1—C2—C11111.64 (13)O8—C17—H17C109.5
C3—C2—O1121.47 (15)H17A—C17—H17B109.5
C3—C2—C11126.89 (15)H17A—C17—H17C109.5
C2—C3—H3119.1H17B—C17—H17C109.5
C2—C3—C4121.78 (15)C12—C11—C2120.42 (14)
C4—C3—H3119.1C12—C11—C16118.90 (17)
O4—C4—C3122.38 (17)C16—C11—C2120.68 (17)
O4—C4—C10121.37 (17)C11—C12—H12119.5
C3—C4—C10116.23 (14)C13—C12—C11120.91 (17)
O5—C5—C6119.77 (17)C13—C12—H12119.5
O5—C5—C10119.75 (18)C12—C13—H13120.1
C6—C5—C10120.48 (16)C14—C13—C12119.8 (2)
C5—C6—H6120.0C14—C13—H13120.1
C5—C6—C7120.03 (16)C13—C14—H14120.1
C7—C6—H6120.0C13—C14—C15119.77 (19)
O7—C7—C6117.47 (17)C15—C14—H14120.1
O7—C7—C8121.31 (18)C14—C15—H15119.7
C8—C7—C6121.22 (16)C16—C15—C14120.69 (19)
O8—C8—C7120.11 (14)C16—C15—H15119.7
O8—C8—C9121.87 (14)C11—C16—H16120.1
C9—C8—C7117.88 (15)C15—C16—C11119.9 (2)
O1—C9—C8116.44 (13)C15—C16—H16120.1
O1—C9—C10121.37 (14)H1WA—O1W—H1WB104.5
C8—C9—C10122.19 (14)H2WA—O2W—H2WB104.5
C5—C10—C4122.63 (15)H3WA—O3W—H3WB104.5
O1—C2—C3—C41.3 (2)C3—C4—C10—C91.0 (2)
O1—C2—C11—C121.85 (19)C5—C6—C7—O7179.31 (15)
O1—C2—C11—C16178.69 (13)C5—C6—C7—C80.2 (3)
O1—C9—C10—C40.5 (2)C6—C5—C10—C4179.03 (14)
O1—C9—C10—C5179.82 (12)C6—C5—C10—C90.6 (2)
O4—C4—C10—C50.2 (2)C6—C7—C8—O8176.35 (14)
O4—C4—C10—C9179.90 (14)C6—C7—C8—C90.6 (2)
O5—C5—C6—C7179.02 (15)C7—C8—C9—O1179.55 (13)
O5—C5—C10—C41.5 (2)C7—C8—C9—C100.5 (2)
O5—C5—C10—C9178.85 (13)C8—C9—C10—C4179.52 (13)
O7—C7—C8—O83.1 (2)C8—C9—C10—C50.2 (2)
O7—C7—C8—C9178.83 (15)C9—O1—C2—C31.94 (19)
O8—C8—C9—O13.9 (2)C9—O1—C2—C11177.57 (11)
O8—C8—C9—C10176.09 (13)C10—C5—C6—C70.5 (2)
C2—O1—C9—C8178.99 (12)C17—O8—C8—C7102.11 (17)
C2—O1—C9—C101.01 (19)C17—O8—C8—C982.35 (18)
C2—C3—C4—O4179.21 (14)C11—C2—C3—C4178.08 (13)
C2—C3—C4—C100.2 (2)C11—C12—C13—C140.2 (3)
C2—C11—C12—C13179.64 (15)C12—C11—C16—C150.7 (2)
C2—C11—C16—C15179.88 (15)C12—C13—C14—C150.8 (3)
C3—C2—C11—C12177.62 (15)C13—C14—C15—C161.0 (3)
C3—C2—C11—C161.8 (2)C14—C15—C16—C110.3 (3)
C3—C4—C10—C5179.28 (14)C16—C11—C12—C130.9 (2)
Geometry of the flavone rings in 13 top
Bond123a
O1—C21.356 (2)1.3625 (13)1.3602 (18)
O1—C91.373 (2)1.3674 (13)1.3682 (18)
C4—O41.271 (2)1.2573 (14)1.2626 (19)
C5—O51.348 (2)1.3586 (14)1.3540 (19)
C6—O61.369 (2)1.3599 (13)-
C7—O71.335 (2)1.3514 (14)1.3481 (18)
C8—O8--1.3743 (19)
O—C171.430 (2)1.4334 (15)1.4363 (19)
C2—C111.476 (3)1.4713 (15)1.467 (2)
C2—C31.355 (3)1.3547 (16)1.356 (2)
C3—C41.432 (3)1.4367 (16)1.431 (2)
C4—C101.432 (3)1.4480 (15)1.442 (2)
C5—C101.422 (3)1.4105 (16)1.415 (2)
C5—C61.379 (3)1.3768 (16)1.378 (2)
C6–C71.408 (3)1.4118 (16)1.401 (2)
C7—C81.392 (3)1.3885 (16)1.396 (2)
C8—C91.379 (3)1.3876 (16)1.388 (2)
C9–C101.405 (3)1.3914 (16)1.402 (2)
 

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