Crystal structures of the flavonoid Oroxylin A and the regioisomers Negletein and Wogonin

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.

Computing details

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)

Crystal data

C16H12O5	F(000) = 592
Mr = 284.26	Dx = 1.530 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
a = 3.8224 (2) Å	Cell parameters from 2316 reflections
b = 19.5339 (7) Å	θ = 3.5–70.7°
c = 16.5360 (6) Å	µ = 0.96 mm^−1
β = 91.604 (4)°	T = 100 K
V = 1234.19 (9) Å^3	Block, clear light yellow
Z = 4	0.1 × 0.1 × 0.02 mm

Data collection

Rigaku OD SuperNova Dual source diffractometer with an Atlas detector	2231 independent reflections
Radiation source: micro-focus sealed X-ray tube	1797 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.032
Detector resolution: 5.1788 pixels mm^-1	θmax = 67.5°, θmin = 3.5°
ω scans	h = −4→3
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2020)	k = −22→23
Tmin = 0.837, Tmax = 1.000	l = −19→18
6384 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.113	w = 1/[σ^2(Fo^2) + (0.0549P)^2 + 0.331P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
2231 reflections	Δρmax = 0.19 e Å^−3
199 parameters	Δρmin = −0.19 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.0710 (4)	0.85831 (6)	0.93733 (7)	0.0267 (3)
C11	0.1867 (5)	0.94300 (10)	0.84057 (11)	0.0282 (4)
C2	0.0486 (5)	0.87404 (10)	0.85750 (11)	0.0264 (4)
O4	−0.3429 (4)	0.72141 (7)	0.77398 (7)	0.0335 (3)
C12	0.2584 (5)	0.98879 (10)	0.90363 (11)	0.0304 (4)
H12	0.2224	0.9752	0.9579	0.036*
O5	−0.4662 (4)	0.63786 (7)	0.89289 (9)	0.0325 (3)
C3	−0.0900 (5)	0.82992 (10)	0.80206 (11)	0.0285 (4)
H3	−0.1039	0.8431	0.7468	0.034*
C13	0.3821 (6)	1.05406 (10)	0.88758 (12)	0.0334 (4)
H13	0.4304	1.0849	0.9309	0.040*
O6	−0.4387 (4)	0.61621 (7)	1.05694 (8)	0.0319 (3)
C4	−0.2158 (5)	0.76388 (10)	0.82508 (11)	0.0278 (4)
C14	0.4353 (6)	1.07446 (10)	0.80887 (12)	0.0340 (4)
H14	0.5153	1.1195	0.7979	0.041*
C5	−0.3225 (5)	0.68599 (10)	0.94187 (11)	0.0272 (4)
O7	−0.1352 (4)	0.70700 (7)	1.15476 (8)	0.0350 (3)
C15	0.3709 (6)	1.02868 (11)	0.74573 (13)	0.0382 (5)
H15	0.4123	1.0422	0.6917	0.046*
C6	−0.3025 (5)	0.67443 (10)	1.02413 (11)	0.0281 (4)
C16	0.2465 (6)	0.96327 (10)	0.76126 (12)	0.0345 (5)
H16	0.2022	0.9323	0.7178	0.041*
C7	−0.1492 (5)	0.72355 (10)	1.07638 (11)	0.0284 (4)
C8	−0.0253 (5)	0.78535 (9)	1.04667 (11)	0.0269 (4)
H8	0.0746	0.8188	1.0820	0.032*
C9	−0.0517 (5)	0.79662 (9)	0.96438 (11)	0.0254 (4)
C10	−0.1960 (5)	0.74853 (10)	0.90979 (11)	0.0266 (4)
C17	−0.2142 (6)	0.55817 (10)	1.04909 (12)	0.0350 (5)
H17A	−0.1534	0.5527	0.9923	0.053*
H17B	−0.3351	0.5170	1.0674	0.053*
H17C	−0.0004	0.5651	1.0822	0.053*
H5	−0.467 (6)	0.6517 (12)	0.8461 (15)	0.025 (5)*
H7	−0.022 (9)	0.7401 (18)	1.186 (2)	0.063 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0373 (7)	0.0201 (6)	0.0226 (6)	−0.0005 (5)	−0.0007 (5)	0.0004 (5)
C11	0.0322 (10)	0.0240 (9)	0.0283 (9)	0.0036 (7)	−0.0018 (7)	−0.0003 (7)
C2	0.0324 (9)	0.0238 (9)	0.0230 (8)	0.0049 (7)	0.0004 (7)	0.0004 (7)
O4	0.0507 (9)	0.0253 (7)	0.0244 (6)	−0.0008 (6)	−0.0038 (6)	−0.0038 (5)
C12	0.0373 (10)	0.0260 (10)	0.0279 (9)	0.0026 (8)	0.0004 (8)	0.0008 (7)
O5	0.0450 (8)	0.0252 (7)	0.0271 (7)	−0.0039 (6)	−0.0036 (6)	−0.0024 (5)
C3	0.0394 (11)	0.0250 (10)	0.0210 (8)	0.0030 (8)	−0.0003 (7)	0.0001 (7)
C13	0.0412 (11)	0.0245 (10)	0.0343 (10)	0.0020 (8)	−0.0039 (8)	−0.0031 (8)
O6	0.0380 (8)	0.0235 (7)	0.0345 (7)	−0.0017 (5)	0.0044 (6)	0.0025 (5)
C4	0.0336 (10)	0.0253 (9)	0.0242 (9)	0.0039 (7)	−0.0024 (7)	−0.0035 (7)
C14	0.0413 (11)	0.0216 (9)	0.0391 (11)	−0.0009 (8)	−0.0013 (8)	0.0036 (8)
C5	0.0283 (9)	0.0232 (9)	0.0300 (9)	0.0023 (7)	−0.0004 (7)	−0.0026 (7)
O7	0.0510 (9)	0.0302 (7)	0.0237 (7)	−0.0048 (6)	−0.0020 (6)	0.0028 (5)
C15	0.0533 (13)	0.0304 (11)	0.0307 (10)	−0.0031 (9)	−0.0009 (9)	0.0068 (8)
C6	0.0313 (10)	0.0225 (9)	0.0305 (9)	0.0016 (7)	0.0029 (7)	0.0007 (7)
C16	0.0502 (12)	0.0272 (10)	0.0261 (9)	−0.0006 (8)	−0.0012 (8)	−0.0009 (7)
C7	0.0331 (10)	0.0271 (9)	0.0249 (9)	0.0035 (7)	0.0007 (7)	0.0003 (7)
C8	0.0326 (10)	0.0223 (9)	0.0255 (9)	0.0018 (7)	−0.0020 (7)	−0.0027 (7)
C9	0.0292 (9)	0.0212 (9)	0.0259 (9)	0.0037 (7)	0.0008 (7)	−0.0002 (7)
C10	0.0290 (9)	0.0238 (9)	0.0268 (9)	0.0041 (7)	0.0002 (7)	−0.0012 (7)
C17	0.0471 (12)	0.0223 (10)	0.0357 (10)	0.0011 (8)	0.0027 (9)	0.0013 (8)

Geometric parameters (Å, º)

O1—C2	1.356 (2)	C14—H14	0.9500
O1—C9	1.373 (2)	C14—C15	1.391 (3)
C11—C2	1.476 (3)	C5—C6	1.379 (3)
C11—C12	1.395 (3)	C5—C10	1.422 (3)
C11—C16	1.395 (3)	O7—C7	1.335 (2)
C2—C3	1.355 (3)	O7—H7	0.93 (4)
O4—C4	1.271 (2)	C15—H15	0.9500
C12—H12	0.9500	C15—C16	1.390 (3)
C12—C13	1.388 (3)	C6—C7	1.408 (3)
O5—C5	1.348 (2)	C16—H16	0.9500
O5—H5	0.82 (3)	C7—C8	1.392 (3)
C3—H3	0.9500	C8—H8	0.9500
C3—C4	1.432 (3)	C8—C9	1.379 (3)
C13—H13	0.9500	C9—C10	1.405 (3)
C13—C14	1.382 (3)	C17—H17A	0.9800
O6—C6	1.369 (2)	C17—H17B	0.9800
O6—C17	1.430 (2)	C17—H17C	0.9800
C4—C10	1.432 (3)
C2—O1—C9	120.22 (14)	C14—C15—H15	119.8
C12—C11—C2	120.47 (17)	C16—C15—C14	120.43 (19)
C16—C11—C2	120.40 (17)	C16—C15—H15	119.8
C16—C11—C12	119.13 (18)	O6—C6—C5	121.03 (17)
O1—C2—C11	112.22 (15)	O6—C6—C7	118.64 (16)
C3—C2—O1	121.83 (17)	C5—C6—C7	120.31 (18)
C3—C2—C11	125.95 (17)	C11—C16—H16	120.0
C11—C12—H12	119.8	C15—C16—C11	120.04 (18)
C13—C12—C11	120.46 (18)	C15—C16—H16	120.0
C13—C12—H12	119.8	O7—C7—C6	115.80 (17)
C5—O5—H5	109.1 (16)	O7—C7—C8	123.23 (17)
C2—C3—H3	119.3	C8—C7—C6	120.96 (17)
C2—C3—C4	121.40 (17)	C7—C8—H8	121.0
C4—C3—H3	119.3	C9—C8—C7	118.07 (17)
C12—C13—H13	119.8	C9—C8—H8	121.0
C14—C13—C12	120.33 (18)	O1—C9—C8	116.44 (16)
C14—C13—H13	119.8	O1—C9—C10	120.62 (16)
C6—O6—C17	112.76 (15)	C8—C9—C10	122.94 (17)
O4—C4—C3	122.42 (17)	C5—C10—C4	122.36 (17)
O4—C4—C10	121.50 (18)	C9—C10—C4	119.83 (17)
C3—C4—C10	116.07 (16)	C9—C10—C5	117.80 (16)
C13—C14—H14	120.2	O6—C17—H17A	109.5
C13—C14—C15	119.60 (19)	O6—C17—H17B	109.5
C15—C14—H14	120.2	O6—C17—H17C	109.5
O5—C5—C6	119.28 (17)	H17A—C17—H17B	109.5
O5—C5—C10	120.82 (16)	H17A—C17—H17C	109.5
C6—C5—C10	119.90 (17)	H17B—C17—H17C	109.5
C7—O7—H7	112 (2)
O1—C2—C3—C4	−0.8 (3)	C13—C14—C15—C16	1.4 (3)
O1—C9—C10—C4	0.0 (3)	O6—C6—C7—O7	3.2 (3)
O1—C9—C10—C5	−179.20 (16)	O6—C6—C7—C8	−176.22 (17)
C11—C2—C3—C4	179.81 (18)	C14—C15—C16—C11	−0.3 (3)
C11—C12—C13—C14	0.1 (3)	C5—C6—C7—O7	−178.60 (18)
C2—O1—C9—C8	−178.71 (16)	C5—C6—C7—C8	2.0 (3)
C2—O1—C9—C10	1.2 (3)	O7—C7—C8—C9	179.61 (18)
C2—C11—C12—C13	−178.80 (18)	C6—C5—C10—C4	−178.83 (19)
C2—C11—C16—C15	178.91 (19)	C6—C5—C10—C9	0.3 (3)
C2—C3—C4—O4	−179.13 (19)	C6—C7—C8—C9	−1.1 (3)
C2—C3—C4—C10	1.9 (3)	C16—C11—C2—O1	167.96 (18)
O4—C4—C10—C5	−1.3 (3)	C16—C11—C2—C3	−12.6 (3)
O4—C4—C10—C9	179.58 (17)	C16—C11—C12—C13	1.1 (3)
C12—C11—C2—O1	−12.2 (3)	C7—C8—C9—O1	179.58 (16)
C12—C11—C2—C3	167.2 (2)	C7—C8—C9—C10	−0.3 (3)
C12—C11—C16—C15	−1.0 (3)	C8—C9—C10—C4	179.82 (18)
C12—C13—C14—C15	−1.3 (3)	C8—C9—C10—C5	0.7 (3)
O5—C5—C6—O6	−2.7 (3)	C9—O1—C2—C11	178.71 (15)
O5—C5—C6—C7	179.13 (17)	C9—O1—C2—C3	−0.7 (3)
O5—C5—C10—C4	0.4 (3)	C10—C5—C6—O6	176.59 (16)
O5—C5—C10—C9	179.55 (17)	C10—C5—C6—C7	−1.6 (3)
C3—C4—C10—C5	177.72 (17)	C17—O6—C6—C5	79.6 (2)
C3—C4—C10—C9	−1.4 (3)	C17—O6—C6—C7	−102.1 (2)

5,6-Dihydroxy-7-methoxy-2-phenyl-4H-chromen-4-one (val120cult)

Crystal data

C16H12O5	F(000) = 592
Mr = 284.26	Dx = 1.466 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 9.78509 (13) Å	Cell parameters from 4050 reflections
b = 15.8032 (2) Å	θ = 4.5–72.5°
c = 8.33104 (11) Å	µ = 0.92 mm^−1
β = 91.3453 (11)°	T = 100 K
V = 1287.92 (3) Å^3	Needle, clear whiteish yellow
Z = 4	0.2 × 0.1 × 0.1 mm

Data collection

Rigaku OD SuperNova Dual source diffractometer with an Atlas detector	2329 independent reflections
Radiation source: micro-focus sealed X-ray tube	2073 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.017
Detector resolution: 10.3577 pixels mm^-1	θmax = 68.0°, θmin = 4.5°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO: Rigaku OD, 2020)	k = −15→18
Tmin = 0.764, Tmax = 1.000	l = −9→9
7020 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.030	w = 1/[σ^2(Fo^2) + (0.0397P)^2 + 0.416P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.079	(Δ/σ)max < 0.001
S = 1.00	Δρmax = 0.20 e Å^−3
2329 reflections	Δρmin = −0.17 e Å^−3
200 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0018 (3)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.35638 (8)	0.36946 (5)	0.31509 (9)	0.0179 (2)
C2	0.23257 (11)	0.40587 (7)	0.28256 (13)	0.0170 (2)
C3	0.17172 (11)	0.45781 (7)	0.38872 (14)	0.0194 (3)
H3	0.0841	0.4806	0.3628	0.023*
O4	0.18595 (8)	0.52927 (5)	0.63906 (10)	0.0229 (2)
C4	0.23687 (11)	0.47912 (7)	0.53970 (13)	0.0180 (2)
O5	0.39369 (9)	0.50619 (5)	0.82813 (9)	0.0214 (2)
H5	0.309 (2)	0.5233 (13)	0.782 (2)	0.064 (6)*
C5	0.44147 (12)	0.45137 (7)	0.71706 (13)	0.0174 (2)
O6	0.63767 (9)	0.41813 (6)	0.88626 (10)	0.0242 (2)
H6	0.599 (2)	0.4507 (12)	0.952 (2)	0.054 (6)*
C6	0.56201 (12)	0.40888 (7)	0.74836 (13)	0.0188 (2)
O7	0.73099 (9)	0.31461 (5)	0.67570 (10)	0.0269 (2)
C7	0.61241 (11)	0.35288 (7)	0.63173 (14)	0.0197 (3)
C8	0.54327 (12)	0.34008 (7)	0.48629 (14)	0.0193 (3)
H8	0.5783	0.3029	0.4075	0.023*
C9	0.42139 (11)	0.38330 (7)	0.45978 (13)	0.0166 (2)
C10	0.36711 (11)	0.43830 (7)	0.57208 (13)	0.0168 (2)
C11	0.18037 (12)	0.38185 (7)	0.12189 (13)	0.0176 (2)
C12	0.26478 (12)	0.33922 (7)	0.01501 (14)	0.0205 (3)
H12	0.3553	0.3242	0.0475	0.025*
C13	0.21661 (13)	0.31889 (7)	−0.13807 (14)	0.0229 (3)
H13	0.2741	0.2897	−0.2098	0.027*
C14	0.08494 (13)	0.34091 (8)	−0.18687 (14)	0.0237 (3)
H14	0.0529	0.3276	−0.2924	0.028*
C15	−0.00004 (12)	0.38244 (7)	−0.08137 (14)	0.0226 (3)
H15	−0.0906	0.3970	−0.1144	0.027*
C16	0.04708 (12)	0.40260 (7)	0.07203 (14)	0.0197 (3)
H16	−0.0116	0.4308	0.1439	0.024*
C17	0.79121 (14)	0.25907 (9)	0.56115 (18)	0.0372 (4)
H17A	0.8735	0.2331	0.6089	0.056*
H17B	0.8157	0.2914	0.4657	0.056*
H17C	0.7256	0.2147	0.5306	0.056*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0157 (4)	0.0207 (4)	0.0171 (4)	0.0019 (3)	−0.0052 (3)	−0.0025 (3)
C2	0.0144 (5)	0.0175 (6)	0.0190 (6)	−0.0009 (4)	−0.0035 (4)	0.0027 (4)
C3	0.0151 (5)	0.0232 (6)	0.0195 (6)	0.0016 (4)	−0.0038 (4)	0.0014 (4)
O4	0.0199 (4)	0.0288 (5)	0.0198 (4)	0.0054 (3)	−0.0023 (3)	−0.0048 (3)
C4	0.0167 (5)	0.0197 (6)	0.0177 (6)	0.0001 (4)	−0.0003 (4)	0.0011 (4)
O5	0.0206 (4)	0.0270 (5)	0.0163 (4)	0.0054 (3)	−0.0041 (3)	−0.0052 (3)
C5	0.0186 (6)	0.0177 (5)	0.0157 (5)	−0.0006 (4)	−0.0008 (4)	−0.0006 (4)
O6	0.0244 (5)	0.0295 (5)	0.0181 (4)	0.0082 (4)	−0.0097 (3)	−0.0062 (4)
C6	0.0198 (6)	0.0201 (6)	0.0163 (5)	−0.0003 (4)	−0.0056 (4)	−0.0007 (4)
O7	0.0241 (5)	0.0287 (5)	0.0272 (5)	0.0123 (4)	−0.0128 (4)	−0.0103 (4)
C7	0.0167 (6)	0.0186 (6)	0.0235 (6)	0.0027 (4)	−0.0054 (4)	−0.0003 (4)
C8	0.0191 (6)	0.0190 (6)	0.0196 (6)	0.0019 (4)	−0.0029 (4)	−0.0039 (4)
C9	0.0168 (5)	0.0177 (5)	0.0152 (5)	−0.0026 (4)	−0.0042 (4)	0.0001 (4)
C10	0.0159 (5)	0.0170 (5)	0.0173 (5)	−0.0010 (4)	−0.0020 (4)	0.0015 (4)
C11	0.0197 (6)	0.0154 (5)	0.0175 (6)	−0.0033 (4)	−0.0040 (4)	0.0028 (4)
C12	0.0213 (6)	0.0193 (6)	0.0208 (6)	0.0004 (4)	−0.0038 (4)	0.0014 (4)
C13	0.0299 (7)	0.0202 (6)	0.0185 (6)	−0.0015 (5)	−0.0012 (5)	−0.0006 (4)
C14	0.0313 (7)	0.0220 (6)	0.0175 (6)	−0.0080 (5)	−0.0080 (5)	0.0021 (4)
C15	0.0212 (6)	0.0226 (6)	0.0237 (6)	−0.0043 (5)	−0.0074 (5)	0.0054 (5)
C16	0.0188 (6)	0.0198 (6)	0.0203 (6)	−0.0028 (4)	−0.0033 (4)	0.0019 (4)
C17	0.0297 (7)	0.0383 (8)	0.0429 (8)	0.0179 (6)	−0.0170 (6)	−0.0226 (6)

Geometric parameters (Å, º)

O1—C2	1.3626 (13)	O7—C7	1.3514 (14)
O1—C9	1.3674 (13)	O7—C17	1.4334 (15)
C2—C3	1.3547 (16)	C7—C8	1.3885 (16)
C2—C11	1.4713 (15)	C8—C9	1.3876 (16)
C3—C4	1.4367 (16)	C9—C10	1.3914 (16)
O4—C4	1.2573 (14)	C11—C12	1.4012 (16)
C4—C10	1.4480 (15)	C11—C16	1.3984 (16)
O5—C5	1.3586 (14)	C12—C13	1.3869 (17)
C5—C6	1.3768 (16)	C13—C14	1.3863 (18)
C5—C10	1.4105 (16)	C14—C15	1.3889 (18)
O6—C6	1.3599 (13)	C15—C16	1.3856 (16)
C6—C7	1.4118 (16)
C2—O1—C9	120.06 (9)	C8—C7—C6	121.40 (10)
O1—C2—C11	111.10 (9)	C9—C8—C7	117.80 (10)
C3—C2—O1	121.90 (10)	O1—C9—C8	116.22 (10)
C3—C2—C11	126.99 (10)	O1—C9—C10	121.04 (10)
C2—C3—C4	121.38 (10)	C8—C9—C10	122.73 (10)
C3—C4—C10	115.42 (10)	C5—C10—C4	121.89 (10)
O4—C4—C3	123.33 (10)	C9—C10—C4	120.08 (10)
O4—C4—C10	121.25 (10)	C9—C10—C5	118.02 (10)
O5—C5—C6	119.27 (10)	C12—C11—C2	120.33 (10)
O5—C5—C10	119.85 (10)	C16—C11—C2	120.74 (10)
C6—C5—C10	120.88 (10)	C16—C11—C12	118.92 (10)
C5—C6—C7	119.13 (10)	C13—C12—C11	120.20 (11)
O6—C6—C5	123.68 (10)	C14—C13—C12	120.33 (11)
O6—C6—C7	117.18 (10)	C13—C14—C15	119.94 (11)
C7—O7—C17	117.21 (9)	C16—C15—C14	120.08 (11)
O7—C7—C6	113.92 (10)	C15—C16—C11	120.52 (11)
O7—C7—C8	124.68 (10)
O1—C2—C3—C4	1.84 (17)	O6—C6—C7—O7	0.79 (15)
O1—C2—C11—C12	−10.02 (14)	O6—C6—C7—C8	−179.17 (10)
O1—C2—C11—C16	171.33 (10)	C6—C5—C10—C4	176.98 (10)
O1—C9—C10—C4	2.72 (16)	C6—C5—C10—C9	−1.99 (16)
O1—C9—C10—C5	−178.30 (10)	C6—C7—C8—C9	−0.92 (17)
C2—O1—C9—C8	176.54 (9)	O7—C7—C8—C9	179.13 (11)
C2—O1—C9—C10	−3.85 (15)	C7—C8—C9—O1	179.74 (10)
C2—C3—C4—O4	177.53 (11)	C7—C8—C9—C10	0.13 (17)
C2—C3—C4—C10	−2.79 (16)	C8—C9—C10—C4	−177.69 (10)
C2—C11—C12—C13	−178.07 (10)	C8—C9—C10—C5	1.29 (17)
C2—C11—C16—C15	177.74 (10)	C9—O1—C2—C3	1.57 (16)
C3—C2—C11—C12	169.12 (11)	C9—O1—C2—C11	−179.25 (9)
C3—C2—C11—C16	−9.54 (18)	C10—C5—C6—O6	−179.38 (10)
C3—C4—C10—C5	−178.39 (10)	C10—C5—C6—C7	1.25 (17)
C3—C4—C10—C9	0.55 (16)	C11—C2—C3—C4	−177.21 (11)
O4—C4—C10—C5	1.29 (17)	C11—C12—C13—C14	0.33 (17)
O4—C4—C10—C9	−179.76 (10)	C12—C11—C16—C15	−0.93 (17)
O5—C5—C6—O6	0.27 (17)	C12—C13—C14—C15	−0.95 (18)
O5—C5—C6—C7	−179.10 (10)	C13—C14—C15—C16	0.62 (18)
O5—C5—C10—C4	−2.67 (17)	C14—C15—C16—C11	0.32 (17)
O5—C5—C10—C9	178.36 (10)	C16—C11—C12—C13	0.60 (17)
C5—C6—C7—O7	−179.80 (10)	C17—O7—C7—C6	−177.82 (11)
C5—C6—C7—C8	0.24 (18)	C17—O7—C7—C8	2.14 (18)

5,7-Dihydroxy-8-methoxy-2-phenyl-4H-chromen-4-one monohydrate (madiha48cult)

Crystal data

C16H12O5·H2O	Dx = 1.436 Mg m^−3
Mr = 302.27	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P212121	Cell parameters from 3063 reflections
a = 4.64835 (6) Å	θ = 5.9–75.5°
b = 16.4123 (2) Å	µ = 0.94 mm^−1
c = 18.3290 (3) Å	T = 100 K
V = 1398.32 (3) Å^3	Block, yellow
Z = 4	0.3 × 0.3 × 0.15 mm
F(000) = 632

Data collection

Rigaku OD SuperNova Dual source diffractometer with an Atlas detector	2486 independent reflections
Radiation source: micro-focus sealed X-ray tube	2433 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.011
Detector resolution: 10.3577 pixels mm^-1	θmax = 67.5°, θmin = 7.2°
ω scans	h = −3→5
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2020)	k = −19→13
Tmin = 0.884, Tmax = 1.000	l = −21→21
3792 measured reflections

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.038P)^2 + 0.130P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.022	(Δ/σ)max < 0.001
wR(F^2) = 0.059	Δρmax = 0.14 e Å^−3
S = 1.03	Δρmin = −0.13 e Å^−3
2486 reflections	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
217 parameters	Extinction coefficient: 0.0038 (5)
0 restraints	Absolute structure: Flack x determined using 964 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Hydrogen site location: mixed	Absolute structure parameter: 0.05 (6)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.5540 (2)	0.57179 (6)	0.22376 (5)	0.0159 (2)
C2	0.6132 (3)	0.53999 (9)	0.15689 (8)	0.0158 (3)
C3	0.4816 (3)	0.47174 (9)	0.13186 (8)	0.0170 (3)
H3	0.5327	0.4508	0.0853	0.020*
O4	0.1384 (2)	0.36789 (6)	0.15132 (6)	0.0203 (3)
C4	0.2671 (3)	0.43068 (9)	0.17412 (8)	0.0163 (3)
O5	−0.1549 (2)	0.36529 (7)	0.27217 (6)	0.0213 (3)
H5	−0.086 (6)	0.3513 (17)	0.2306 (16)	0.056 (8)*
C5	−0.0049 (3)	0.43234 (9)	0.29236 (8)	0.0168 (3)
C6	−0.0574 (3)	0.46767 (10)	0.35926 (8)	0.0178 (3)
H6	−0.1968	0.4448	0.3912	0.021*
O7	0.0424 (3)	0.56936 (7)	0.44646 (6)	0.0212 (3)
H7	0.163 (5)	0.6117 (15)	0.4551 (13)	0.039 (6)*
C7	0.0955 (3)	0.53744 (9)	0.38004 (8)	0.0170 (3)
O8	0.4543 (2)	0.63908 (6)	0.35711 (6)	0.0189 (2)
C8	0.3008 (3)	0.57230 (9)	0.33407 (8)	0.0162 (3)
C9	0.3508 (3)	0.53563 (9)	0.26700 (8)	0.0148 (3)
C10	0.2027 (3)	0.46562 (9)	0.24440 (8)	0.0153 (3)
C11	0.8294 (3)	0.58814 (9)	0.11764 (8)	0.0161 (3)
C12	0.9489 (3)	0.65811 (10)	0.14900 (8)	0.0193 (3)
H12	0.8885	0.6750	0.1962	0.023*
C13	1.1543 (3)	0.70295 (10)	0.11190 (9)	0.0217 (3)
H13	1.2354	0.7501	0.1339	0.026*
C14	1.2420 (3)	0.67930 (10)	0.04282 (9)	0.0217 (3)
H14	1.3842	0.7099	0.0176	0.026*
C15	1.1213 (3)	0.61064 (10)	0.01052 (9)	0.0214 (3)
H15	1.1788	0.5951	−0.0372	0.026*
C16	0.9188 (3)	0.56505 (10)	0.04729 (8)	0.0193 (3)
H16	0.8394	0.5179	0.0250	0.023*
C17	0.3416 (4)	0.71412 (10)	0.32867 (10)	0.0273 (4)
H17A	0.3639	0.7149	0.2755	0.041*
H17B	0.4468	0.7601	0.3500	0.041*
H17C	0.1372	0.7186	0.3411	0.041*
O1W	0.2807 (3)	0.70168 (7)	0.51350 (6)	0.0214 (3)
H1WA	0.430 (7)	0.7262 (16)	0.5025 (16)	0.055 (8)*
H1WB	0.312 (5)	0.6794 (13)	0.5572 (14)	0.037 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0176 (5)	0.0176 (5)	0.0125 (5)	−0.0004 (4)	0.0014 (4)	−0.0007 (4)
C2	0.0152 (7)	0.0197 (7)	0.0127 (7)	0.0042 (6)	−0.0022 (6)	−0.0008 (6)
C3	0.0183 (7)	0.0190 (7)	0.0136 (7)	0.0022 (6)	−0.0003 (6)	−0.0009 (5)
O4	0.0248 (5)	0.0173 (5)	0.0186 (5)	−0.0019 (5)	0.0007 (4)	−0.0034 (4)
C4	0.0176 (7)	0.0148 (7)	0.0164 (7)	0.0045 (6)	−0.0029 (6)	0.0005 (6)
O5	0.0273 (6)	0.0184 (5)	0.0182 (6)	−0.0055 (5)	0.0020 (5)	−0.0009 (4)
C5	0.0187 (7)	0.0143 (7)	0.0174 (7)	0.0021 (6)	−0.0024 (6)	0.0016 (6)
C6	0.0190 (6)	0.0196 (7)	0.0148 (7)	0.0003 (6)	0.0014 (6)	0.0032 (5)
O7	0.0279 (6)	0.0227 (6)	0.0129 (5)	−0.0025 (5)	0.0040 (4)	−0.0021 (4)
C7	0.0204 (7)	0.0180 (7)	0.0126 (7)	0.0038 (6)	−0.0008 (6)	0.0010 (6)
O8	0.0232 (5)	0.0170 (5)	0.0167 (5)	−0.0013 (5)	−0.0025 (4)	−0.0015 (4)
C8	0.0189 (7)	0.0145 (7)	0.0152 (7)	0.0024 (6)	−0.0015 (6)	0.0009 (6)
C9	0.0144 (7)	0.0151 (7)	0.0149 (7)	0.0020 (6)	−0.0008 (6)	0.0035 (5)
C10	0.0172 (7)	0.0153 (7)	0.0134 (7)	0.0039 (6)	−0.0013 (6)	0.0014 (5)
C11	0.0142 (6)	0.0181 (7)	0.0158 (7)	0.0039 (5)	−0.0021 (6)	0.0016 (6)
C12	0.0207 (7)	0.0219 (7)	0.0151 (7)	0.0013 (6)	0.0005 (6)	−0.0005 (6)
C13	0.0215 (7)	0.0202 (7)	0.0235 (8)	−0.0015 (6)	−0.0016 (7)	0.0004 (6)
C14	0.0185 (7)	0.0243 (8)	0.0224 (8)	0.0020 (6)	0.0029 (6)	0.0064 (6)
C15	0.0222 (8)	0.0256 (7)	0.0163 (7)	0.0049 (6)	0.0037 (6)	0.0006 (6)
C16	0.0190 (7)	0.0216 (7)	0.0172 (7)	0.0022 (6)	0.0002 (6)	−0.0003 (6)
C17	0.0395 (10)	0.0160 (8)	0.0265 (9)	−0.0011 (7)	−0.0059 (8)	0.0001 (6)
O1W	0.0249 (6)	0.0235 (6)	0.0157 (6)	−0.0014 (5)	−0.0010 (5)	0.0025 (5)

Geometric parameters (Å, º)

O1—C2	1.3602 (18)	C8—C9	1.388 (2)
O1—C9	1.3682 (18)	C9—C10	1.402 (2)
C2—C3	1.356 (2)	C11—C12	1.399 (2)
C2—C11	1.467 (2)	C11—C16	1.407 (2)
C3—H3	0.9500	C12—H12	0.9500
C3—C4	1.431 (2)	C12—C13	1.384 (2)
O4—C4	1.2626 (19)	C13—H13	0.9500
C4—C10	1.442 (2)	C13—C14	1.386 (2)
O5—H5	0.86 (3)	C14—H14	0.9500
O5—C5	1.3540 (19)	C14—C15	1.391 (2)
C5—C6	1.378 (2)	C15—H15	0.9500
C5—C10	1.415 (2)	C15—C16	1.378 (2)
C6—H6	0.9500	C16—H16	0.9500
C6—C7	1.401 (2)	C17—H17A	0.9800
O7—H7	0.91 (3)	C17—H17B	0.9800
O7—C7	1.3481 (18)	C17—H17C	0.9800
C7—C8	1.396 (2)	O1W—H1WA	0.83 (3)
O8—C8	1.3743 (19)	O1W—H1WB	0.89 (3)
O8—C17	1.4363 (19)
C2—O1—C9	119.69 (12)	C5—C10—C4	122.89 (14)
O1—C2—C11	111.96 (12)	C9—C10—C4	119.22 (14)
C3—C2—O1	122.02 (14)	C9—C10—C5	117.89 (13)
C3—C2—C11	126.01 (14)	C12—C11—C2	120.83 (14)
C2—C3—H3	119.3	C12—C11—C16	118.70 (14)
C2—C3—C4	121.34 (14)	C16—C11—C2	120.47 (14)
C4—C3—H3	119.3	C11—C12—H12	119.7
C3—C4—C10	116.17 (14)	C13—C12—C11	120.56 (14)
O4—C4—C3	122.36 (14)	C13—C12—H12	119.7
O4—C4—C10	121.47 (14)	C12—C13—H13	119.9
C5—O5—H5	105.6 (19)	C12—C13—C14	120.20 (15)
O5—C5—C6	119.60 (14)	C14—C13—H13	119.9
O5—C5—C10	119.67 (13)	C13—C14—H14	120.1
C6—C5—C10	120.72 (14)	C13—C14—C15	119.80 (15)
C5—C6—H6	120.1	C15—C14—H14	120.1
C5—C6—C7	119.75 (14)	C14—C15—H15	119.8
C7—C6—H6	120.1	C16—C15—C14	120.47 (15)
C7—O7—H7	110.1 (16)	C16—C15—H15	119.8
O7—C7—C6	118.06 (13)	C11—C16—H16	119.9
O7—C7—C8	120.73 (14)	C15—C16—C11	120.25 (15)
C8—C7—C6	121.20 (14)	C15—C16—H16	119.9
C8—O8—C17	112.52 (12)	O8—C17—H17A	109.5
O8—C8—C7	119.77 (13)	O8—C17—H17B	109.5
O8—C8—C9	122.06 (13)	O8—C17—H17C	109.5
C9—C8—C7	118.12 (14)	H17A—C17—H17B	109.5
O1—C9—C8	116.14 (13)	H17A—C17—H17C	109.5
O1—C9—C10	121.54 (13)	H17B—C17—H17C	109.5
C8—C9—C10	122.32 (14)	H1WA—O1W—H1WB	106 (3)
O1—C2—C3—C4	1.6 (2)	C6—C5—C10—C9	−0.4 (2)
O1—C2—C11—C12	−0.35 (19)	C6—C7—C8—O8	−177.74 (13)
O1—C2—C11—C16	−179.84 (13)	C6—C7—C8—C9	−0.3 (2)
O1—C9—C10—C4	0.3 (2)	O7—C7—C8—O8	1.1 (2)
O1—C9—C10—C5	−179.72 (13)	O7—C7—C8—C9	178.54 (13)
C2—O1—C9—C8	−179.33 (12)	C7—C8—C9—O1	−179.93 (12)
C2—O1—C9—C10	0.6 (2)	C7—C8—C9—C10	0.1 (2)
C2—C3—C4—O4	178.77 (14)	O8—C8—C9—O1	−2.6 (2)
C2—C3—C4—C10	−0.5 (2)	O8—C8—C9—C10	177.47 (13)
C2—C11—C12—C13	179.52 (14)	C8—C9—C10—C4	−179.70 (14)
C2—C11—C16—C15	179.78 (14)	C8—C9—C10—C5	0.2 (2)
C3—C2—C11—C12	179.48 (15)	C9—O1—C2—C3	−1.6 (2)
C3—C2—C11—C16	0.0 (2)	C9—O1—C2—C11	178.23 (12)
C3—C4—C10—C5	179.68 (13)	C10—C5—C6—C7	0.2 (2)
C3—C4—C10—C9	−0.37 (19)	C11—C2—C3—C4	−178.24 (13)
O4—C4—C10—C5	0.4 (2)	C11—C12—C13—C14	0.6 (2)
O4—C4—C10—C9	−179.69 (14)	C12—C11—C16—C15	0.3 (2)
O5—C5—C6—C7	−179.45 (13)	C12—C13—C14—C15	0.5 (2)
O5—C5—C10—C4	−0.8 (2)	C13—C14—C15—C16	−1.2 (2)
O5—C5—C10—C9	179.26 (13)	C14—C15—C16—C11	0.8 (2)
C5—C6—C7—O7	−178.71 (14)	C16—C11—C12—C13	−1.0 (2)
C5—C6—C7—C8	0.2 (2)	C17—O8—C8—C7	−99.41 (17)
C6—C5—C10—C4	179.55 (13)	C17—O8—C8—C9	83.26 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
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^i	0.83 (3)	2.04 (3)	2.8570 (13)	172 (3)
O1W—H1WB···O4^ii	0.89 (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)

Crystal data

C16H12O5·1.25H2O	F(000) = 642
Mr = 306.78	Dx = 1.477 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
a = 4.39382 (9) Å	Cell parameters from 4183 reflections
b = 18.7848 (3) Å	θ = 3.5–74.3°
c = 16.8308 (3) Å	µ = 0.97 mm^−1
β = 96.5918 (19)°	T = 100 K
V = 1379.98 (5) Å^3	Plate, yellow
Z = 4	0.4 × 0.08 × 0.05 mm

Data collection

Rigaku OD SuperNova Dual source diffractometer with an Atlas detector	Rint = 0.019
ω scans	θmax = 67.5°, θmin = 7.1°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2020)	h = −3→5
Tmin = 0.818, Tmax = 1.000	k = −21→22
7256 measured reflections	l = −20→20
2416 independent reflections	3 standard reflections every 30 min
2173 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.044	H-atom parameters constrained
wR(F^2) = 0.113	w = 1/[σ^2(Fo^2) + (0.0532P)^2 + 0.643P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
2416 reflections	Δρmax = 0.29 e Å^−3
223 parameters	Δρmin = −0.26 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.5558 (2)	0.76190 (5)	0.18290 (6)	0.0235 (3)
O4	0.2880 (3)	0.84255 (8)	0.38900 (7)	0.0502 (4)
O5	−0.0181 (3)	0.72740 (9)	0.40586 (8)	0.0547 (4)
H5	0.0171	0.7712	0.4110	0.082*
O7	0.0203 (4)	0.54743 (7)	0.21340 (9)	0.0601 (5)
H7	0.0847	0.5393	0.1692	0.090*
O8	0.4021 (3)	0.62888 (6)	0.12845 (6)	0.0360 (3)
C2	0.6428 (3)	0.82849 (8)	0.20820 (9)	0.0257 (3)
C3	0.5591 (4)	0.85584 (9)	0.27672 (10)	0.0324 (4)
H3	0.6278	0.9021	0.2931	0.039*
C4	0.3708 (4)	0.81719 (9)	0.32510 (9)	0.0322 (4)
C5	0.0852 (4)	0.70379 (10)	0.33789 (10)	0.0362 (4)
C6	0.0029 (4)	0.63732 (11)	0.30907 (11)	0.0414 (5)
H6	−0.1235	0.6078	0.3373	0.050*
C7	0.1051 (4)	0.61308 (9)	0.23829 (10)	0.0380 (4)
C8	0.2905 (4)	0.65540 (8)	0.19546 (9)	0.0284 (3)
C9	0.3729 (3)	0.72211 (8)	0.22582 (8)	0.0230 (3)
C10	0.2746 (3)	0.74783 (9)	0.29687 (9)	0.0281 (3)
C17	0.2384 (5)	0.65378 (9)	0.05454 (10)	0.0372 (4)
H17A	0.0199	0.6431	0.0540	0.056*
H17B	0.3177	0.6299	0.0094	0.056*
H17C	0.2665	0.7053	0.0500	0.056*
C11	0.8273 (3)	0.86362 (8)	0.15237 (11)	0.0306 (4)
C12	0.8860 (4)	0.82958 (9)	0.08227 (11)	0.0350 (4)
H12	0.8047	0.7834	0.0706	0.042*
C13	1.0614 (4)	0.86210 (11)	0.02931 (13)	0.0453 (5)
H13	1.1004	0.8382	−0.0182	0.054*
C14	1.1796 (4)	0.92934 (12)	0.04586 (15)	0.0524 (6)
H14	1.3020	0.9516	0.0100	0.063*
C15	1.1187 (4)	0.96427 (11)	0.11507 (16)	0.0554 (6)
H15	1.1974	1.0108	0.1259	0.066*
C16	0.9449 (4)	0.93205 (9)	0.16824 (13)	0.0425 (5)
H16	0.9053	0.9563	0.2155	0.051*
O1W	0.2844 (10)	0.47744 (16)	0.0807 (2)	0.0736 (11)	0.5
H1WA	0.3395	0.4794	0.0328	0.110*	0.5
H1WB	0.2718	0.4321	0.0906	0.110*	0.5
O2W	0.9631 (8)	0.48649 (13)	0.07684 (15)	0.0452 (7)	0.5
H2WA	1.0454	0.4953	0.0333	0.068*	0.5
H2WB	0.7786	0.4720	0.0602	0.068*	0.5
O3W	0.3848 (16)	0.5034 (3)	−0.0616 (4)	0.0568 (15)	0.25
H3WA	0.4666	0.4618	−0.0670	0.085*	0.25
H3WB	0.2256	0.5042	−0.0974	0.085*	0.25

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0265 (5)	0.0189 (5)	0.0249 (5)	0.0014 (4)	0.0026 (4)	−0.0038 (4)
O4	0.0599 (8)	0.0635 (9)	0.0253 (6)	0.0337 (7)	−0.0040 (5)	−0.0164 (6)
O5	0.0568 (8)	0.0797 (10)	0.0310 (7)	0.0364 (8)	0.0201 (6)	0.0209 (7)
O7	0.0895 (12)	0.0323 (7)	0.0521 (9)	−0.0260 (7)	−0.0197 (8)	0.0205 (6)
O8	0.0628 (8)	0.0210 (5)	0.0225 (6)	0.0056 (5)	−0.0031 (5)	−0.0018 (4)
C2	0.0205 (7)	0.0195 (7)	0.0347 (8)	0.0045 (5)	−0.0068 (6)	−0.0034 (6)
C3	0.0313 (8)	0.0263 (8)	0.0366 (9)	0.0090 (6)	−0.0088 (6)	−0.0120 (6)
C4	0.0320 (8)	0.0401 (9)	0.0224 (7)	0.0180 (7)	−0.0060 (6)	−0.0083 (6)
C5	0.0306 (8)	0.0525 (11)	0.0257 (8)	0.0168 (7)	0.0038 (6)	0.0146 (7)
C6	0.0338 (9)	0.0520 (11)	0.0383 (10)	0.0034 (8)	0.0028 (7)	0.0253 (8)
C7	0.0432 (9)	0.0317 (9)	0.0353 (9)	−0.0054 (7)	−0.0120 (7)	0.0146 (7)
C8	0.0381 (8)	0.0234 (7)	0.0219 (7)	0.0003 (6)	−0.0039 (6)	0.0029 (6)
C9	0.0237 (7)	0.0239 (7)	0.0204 (7)	0.0032 (5)	−0.0013 (5)	0.0020 (6)
C10	0.0256 (7)	0.0372 (8)	0.0203 (7)	0.0117 (6)	−0.0023 (6)	0.0013 (6)
C17	0.0613 (11)	0.0260 (8)	0.0226 (8)	−0.0032 (7)	−0.0022 (7)	0.0023 (6)
C11	0.0190 (7)	0.0250 (8)	0.0454 (9)	0.0036 (6)	−0.0064 (6)	0.0043 (7)
C12	0.0252 (8)	0.0330 (9)	0.0473 (10)	0.0007 (6)	0.0055 (7)	0.0049 (7)
C13	0.0276 (8)	0.0525 (11)	0.0565 (12)	0.0022 (8)	0.0074 (8)	0.0178 (9)
C14	0.0252 (8)	0.0527 (12)	0.0767 (15)	−0.0059 (8)	−0.0053 (9)	0.0348 (11)
C15	0.0375 (10)	0.0358 (10)	0.0860 (17)	−0.0124 (8)	−0.0219 (10)	0.0247 (11)
C16	0.0352 (9)	0.0259 (8)	0.0617 (12)	−0.0033 (7)	−0.0148 (8)	0.0066 (8)
O1W	0.134 (4)	0.0287 (15)	0.062 (2)	−0.0152 (18)	0.027 (2)	−0.0054 (13)
O2W	0.084 (2)	0.0237 (12)	0.0266 (12)	−0.0049 (12)	−0.0021 (12)	−0.0031 (9)
O3W	0.062 (4)	0.042 (3)	0.069 (4)	0.010 (3)	0.015 (3)	−0.010 (3)

Geometric parameters (Å, º)

O1—C2	1.3619 (18)	C17—H17A	0.9800
O1—C9	1.3637 (18)	C17—H17B	0.9800
O4—C4	1.267 (2)	C17—H17C	0.9800
O5—H5	0.8400	C11—C12	1.392 (3)
O5—C5	1.353 (2)	C11—C16	1.400 (2)
O7—H7	0.8400	C12—H12	0.9500
O7—C7	1.341 (2)	C12—C13	1.385 (3)
O8—C8	1.374 (2)	C13—H13	0.9500
O8—C17	1.442 (2)	C13—C14	1.382 (3)
C2—C3	1.351 (2)	C14—H14	0.9500
C2—C11	1.467 (2)	C14—C15	1.389 (4)
C3—H3	0.9500	C15—H15	0.9500
C3—C4	1.425 (3)	C15—C16	1.381 (3)
C4—C10	1.434 (2)	C16—H16	0.9500
C5—C6	1.373 (3)	O1W—H1WA	0.8699
C5—C10	1.409 (2)	O1W—H1WB	0.8700
C6—H6	0.9500	O2W—H2WA	0.8691
C6—C7	1.397 (3)	O2W—H2WB	0.8704
C7—C8	1.397 (2)	O3W—H3WA	0.8701
C8—C9	1.386 (2)	O3W—H3WB	0.8699
C9—C10	1.403 (2)
C2—O1—C9	119.93 (12)	C9—C10—C4	119.18 (15)
C5—O5—H5	109.5	C9—C10—C5	118.18 (15)
C7—O7—H7	109.5	O8—C17—H17A	109.5
C8—O8—C17	113.64 (13)	O8—C17—H17B	109.5
O1—C2—C11	111.64 (13)	O8—C17—H17C	109.5
C3—C2—O1	121.47 (15)	H17A—C17—H17B	109.5
C3—C2—C11	126.89 (15)	H17A—C17—H17C	109.5
C2—C3—H3	119.1	H17B—C17—H17C	109.5
C2—C3—C4	121.78 (15)	C12—C11—C2	120.42 (14)
C4—C3—H3	119.1	C12—C11—C16	118.90 (17)
O4—C4—C3	122.38 (17)	C16—C11—C2	120.68 (17)
O4—C4—C10	121.37 (17)	C11—C12—H12	119.5
C3—C4—C10	116.23 (14)	C13—C12—C11	120.91 (17)
O5—C5—C6	119.77 (17)	C13—C12—H12	119.5
O5—C5—C10	119.75 (18)	C12—C13—H13	120.1
C6—C5—C10	120.48 (16)	C14—C13—C12	119.8 (2)
C5—C6—H6	120.0	C14—C13—H13	120.1
C5—C6—C7	120.03 (16)	C13—C14—H14	120.1
C7—C6—H6	120.0	C13—C14—C15	119.77 (19)
O7—C7—C6	117.47 (17)	C15—C14—H14	120.1
O7—C7—C8	121.31 (18)	C14—C15—H15	119.7
C8—C7—C6	121.22 (16)	C16—C15—C14	120.69 (19)
O8—C8—C7	120.11 (14)	C16—C15—H15	119.7
O8—C8—C9	121.87 (14)	C11—C16—H16	120.1
C9—C8—C7	117.88 (15)	C15—C16—C11	119.9 (2)
O1—C9—C8	116.44 (13)	C15—C16—H16	120.1
O1—C9—C10	121.37 (14)	H1WA—O1W—H1WB	104.5
C8—C9—C10	122.19 (14)	H2WA—O2W—H2WB	104.5
C5—C10—C4	122.63 (15)	H3WA—O3W—H3WB	104.5
O1—C2—C3—C4	−1.3 (2)	C3—C4—C10—C9	1.0 (2)
O1—C2—C11—C12	1.85 (19)	C5—C6—C7—O7	179.31 (15)
O1—C2—C11—C16	−178.69 (13)	C5—C6—C7—C8	−0.2 (3)
O1—C9—C10—C4	−0.5 (2)	C6—C5—C10—C4	−179.03 (14)
O1—C9—C10—C5	179.82 (12)	C6—C5—C10—C9	0.6 (2)
O4—C4—C10—C5	−0.2 (2)	C6—C7—C8—O8	176.35 (14)
O4—C4—C10—C9	−179.90 (14)	C6—C7—C8—C9	0.6 (2)
O5—C5—C6—C7	179.02 (15)	C7—C8—C9—O1	179.55 (13)
O5—C5—C10—C4	1.5 (2)	C7—C8—C9—C10	−0.5 (2)
O5—C5—C10—C9	−178.85 (13)	C8—C9—C10—C4	179.52 (13)
O7—C7—C8—O8	−3.1 (2)	C8—C9—C10—C5	−0.2 (2)
O7—C7—C8—C9	−178.83 (15)	C9—O1—C2—C3	1.94 (19)
O8—C8—C9—O1	3.9 (2)	C9—O1—C2—C11	−177.57 (11)
O8—C8—C9—C10	−176.09 (13)	C10—C5—C6—C7	−0.5 (2)
C2—O1—C9—C8	178.99 (12)	C17—O8—C8—C7	102.11 (17)
C2—O1—C9—C10	−1.01 (19)	C17—O8—C8—C9	−82.35 (18)
C2—C3—C4—O4	−179.21 (14)	C11—C2—C3—C4	178.08 (13)
C2—C3—C4—C10	−0.2 (2)	C11—C12—C13—C14	−0.2 (3)
C2—C11—C12—C13	−179.64 (15)	C12—C11—C16—C15	−0.7 (2)
C2—C11—C16—C15	179.88 (15)	C12—C13—C14—C15	−0.8 (3)
C3—C2—C11—C12	−177.62 (15)	C13—C14—C15—C16	1.0 (3)
C3—C2—C11—C16	1.8 (2)	C14—C15—C16—C11	−0.3 (3)
C3—C4—C10—C5	−179.28 (14)	C16—C11—C12—C13	0.9 (2)