9-(4-Hy-droxy-3,5-dimeth-oxy-phen-yl)-3,3,6,6-tetra-methyl-3,4,5,6,7,9-hexa-hydro-1H-xanthene-1,8(2H)-dione.

In the title compound, C(25)H(30)O(6), the two fused cyclo-hexa-none rings have envelope conformations, whereas the central pyran ring is roughly planar [mximum deviation = 0.045 (2) Å]. The pyran and benzene rings are almost perpendicular to each other, making a dihedral angle of 86.32 (2)°. In the crystal, molecules are linked via pairs of O-H⋯O hydrogen bonds, forming inversion dimers.

Related literature

For the synthesis of xanthenes, see: Vang & Stankevich (1960 ▶); Hilderbrand & Weissleder (2007 ▶). For their pharmaceutical properties, see: Lambert et al. (1997 ▶); Poupelin et al. (1978 ▶); Hideo (1981 ▶); Selvanayagam et al. (1996 ▶); Jonathan et al. (1988 ▶). For related structures, see Mehdi et al. (2011 ▶); Odabasoglu et al. (2008 ▶). For the assignment of ring conformations, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C25H30O6

M = 426.49

Triclinic,

a = 9.4268 (9) Å

b = 10.2468 (10) Å

c = 12.6122 (11) Å

α = 84.973 (6)°

β = 70.377 (5)°

γ = 75.676 (6)°

V = 1111.83 (18) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.924, T max = 0.982

20849 measured reflections

5233 independent reflections

2876 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.157

S = 0.98

5233 reflections

288 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812010410/im2356sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010410/im2356Isup5.hkl

Supplementary material file. DOI: 10.1107/S1600536812010410/im2356Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C25H30O6	Z = 2
Mr = 426.49	F(000) = 456
Triclinic, P1	Dx = 1.274 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4268 (9) Å	Cell parameters from 5637 reflections
b = 10.2468 (10) Å	θ = 2.4–27.5°
c = 12.6122 (11) Å	µ = 0.09 mm−1
α = 84.973 (6)°	T = 295 K
β = 70.377 (5)°	Block, colourless
γ = 75.676 (6)°	0.30 × 0.25 × 0.20 mm
V = 1111.83 (18) Å3

Bruker Kappa APEXII CCD diffractometer	5233 independent reflections
Radiation source: fine-focus sealed tube	2876 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
ω and φ scan	θmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −12→12
Tmin = 0.924, Tmax = 0.982	k = −13→13
20849 measured reflections	l = −16→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051	H-atom parameters constrained
wR(F2) = 0.157	w = 1/[σ2(Fo2) + (0.0666P)2 + 0.3374P] where P = (Fo2 + 2Fc2)/3
S = 0.98	(Δ/σ)max < 0.001
5233 reflections	Δρmax = 0.28 e Å−3
288 parameters	Δρmin = −0.21 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.008 (2)

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	0.2424 (2)	0.1023 (2)	0.33354 (14)	0.0336 (5)
C2	0.1297 (3)	0.0482 (2)	0.30200 (15)	0.0418 (5)
H2A	0.0310	0.0657	0.3621	0.050*
H2B	0.1666	−0.0486	0.2923	0.050*
C3	0.1076 (3)	0.1131 (2)	0.19256 (16)	0.0466 (6)
C4	0.2682 (3)	0.0985 (3)	0.10508 (16)	0.0509 (6)
H4A	0.3068	0.0052	0.0814	0.061*
H4B	0.2577	0.1524	0.0398	0.061*
C5	0.3873 (2)	0.1383 (2)	0.14149 (15)	0.0381 (5)
C6	0.3614 (2)	0.1462 (2)	0.26230 (14)	0.0337 (5)
C7	0.4681 (2)	0.2063 (2)	0.29943 (14)	0.0354 (5)
H7	0.5748	0.1561	0.2636	0.042*
C8	0.4297 (2)	0.1905 (2)	0.42567 (15)	0.0367 (5)
C9	0.5320 (3)	0.2232 (2)	0.47906 (17)	0.0471 (6)
C10	0.4874 (3)	0.2148 (3)	0.60591 (17)	0.0525 (6)
H10A	0.5232	0.2833	0.6315	0.063*
H10B	0.5411	0.1279	0.6263	0.063*
C11	0.3143 (3)	0.2328 (2)	0.66833 (16)	0.0451 (6)
C12	0.2551 (3)	0.1381 (2)	0.61580 (15)	0.0427 (5)
H12A	0.2915	0.0464	0.6383	0.051*
H12B	0.1429	0.1598	0.6446	0.051*
C13	0.3068 (2)	0.1463 (2)	0.49008 (14)	0.0349 (5)
C14	0.0234 (3)	0.2601 (3)	0.2129 (2)	0.0638 (7)
H14A	0.0834	0.3068	0.2375	0.096*
H14B	−0.0758	0.2663	0.2698	0.096*
H14C	0.0094	0.3002	0.1443	0.096*
C15	0.0135 (4)	0.0391 (3)	0.1523 (2)	0.0787 (9)
H15A	−0.0879	0.0488	0.2070	0.118*
H15B	0.0644	−0.0547	0.1429	0.118*
H15C	0.0047	0.0765	0.0817	0.118*
C16	0.2298 (3)	0.3783 (3)	0.6599 (2)	0.0667 (7)
H16A	0.2408	0.4010	0.5825	0.100*
H16B	0.2731	0.4365	0.6893	0.100*
H16C	0.1220	0.3895	0.7026	0.100*
C17	0.2863 (3)	0.1950 (3)	0.79273 (17)	0.0620 (7)
H17A	0.3218	0.2549	0.8271	0.093*
H17B	0.3419	0.1041	0.7987	0.093*
H17C	0.1776	0.2025	0.8303	0.093*
C19	0.4554 (2)	0.3532 (2)	0.26216 (15)	0.0356 (5)
C20	0.5677 (2)	0.3897 (2)	0.16956 (15)	0.0386 (5)
H20	0.6574	0.3259	0.1343	0.046*
C21	0.5475 (2)	0.5199 (2)	0.12944 (15)	0.0395 (5)
C22	0.4165 (2)	0.6183 (2)	0.18321 (16)	0.0401 (5)
C23	0.3081 (2)	0.5825 (2)	0.27940 (16)	0.0401 (5)
C24	0.3262 (2)	0.4511 (2)	0.31724 (15)	0.0402 (5)
H24	0.2510	0.4279	0.3804	0.048*
C25	0.7846 (3)	0.4710 (3)	−0.02256 (19)	0.0637 (7)
H25A	0.8480	0.4413	0.0246	0.096*
H25B	0.8412	0.5123	−0.0894	0.096*
H25C	0.7565	0.3952	−0.0428	0.096*
C26	0.1124 (3)	0.6717 (3)	0.44614 (19)	0.0619 (7)
H26A	0.0458	0.6106	0.4588	0.093*
H26B	0.0524	0.7580	0.4775	0.093*
H26C	0.1899	0.6371	0.4815	0.093*
O1	0.21042 (15)	0.10108 (15)	0.44842 (10)	0.0387 (4)
O2	0.50511 (17)	0.16061 (16)	0.07249 (11)	0.0510 (4)
O3	0.6537 (2)	0.2498 (2)	0.42231 (14)	0.0770 (6)
O4	0.18392 (19)	0.68547 (17)	0.33083 (12)	0.0575 (5)
O5	0.39109 (19)	0.74774 (16)	0.14607 (12)	0.0555 (5)
H5	0.4487	0.7521	0.0813	0.073 (9)*
O6	0.64868 (18)	0.56614 (16)	0.03654 (12)	0.0530 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0421 (11)	0.0337 (13)	0.0199 (9)	−0.0064 (9)	−0.0053 (8)	0.0003 (7)
C2	0.0538 (13)	0.0461 (15)	0.0271 (10)	−0.0215 (11)	−0.0090 (9)	0.0029 (9)
C3	0.0586 (14)	0.0583 (17)	0.0297 (11)	−0.0259 (13)	−0.0163 (10)	0.0083 (9)
C4	0.0692 (15)	0.0593 (17)	0.0239 (10)	−0.0193 (13)	−0.0115 (10)	−0.0005 (9)
C5	0.0487 (12)	0.0331 (13)	0.0237 (9)	−0.0060 (10)	−0.0028 (9)	−0.0005 (8)
C6	0.0393 (11)	0.0327 (12)	0.0232 (9)	−0.0061 (9)	−0.0047 (8)	0.0018 (7)
C7	0.0339 (10)	0.0413 (13)	0.0235 (9)	−0.0062 (9)	−0.0024 (8)	0.0024 (8)
C8	0.0402 (11)	0.0398 (14)	0.0252 (9)	−0.0066 (10)	−0.0068 (8)	0.0025 (8)
C9	0.0458 (13)	0.0583 (17)	0.0372 (11)	−0.0162 (12)	−0.0113 (10)	0.0029 (10)
C10	0.0585 (14)	0.0681 (18)	0.0382 (12)	−0.0219 (13)	−0.0209 (11)	0.0044 (10)
C11	0.0577 (14)	0.0515 (16)	0.0275 (10)	−0.0153 (12)	−0.0139 (9)	0.0006 (9)
C12	0.0507 (13)	0.0514 (15)	0.0238 (9)	−0.0152 (11)	−0.0083 (9)	0.0050 (9)
C13	0.0396 (11)	0.0395 (13)	0.0230 (9)	−0.0082 (9)	−0.0081 (8)	0.0028 (8)
C14	0.0564 (15)	0.067 (2)	0.0646 (16)	−0.0124 (14)	−0.0213 (13)	0.0180 (13)
C15	0.103 (2)	0.117 (3)	0.0458 (14)	−0.067 (2)	−0.0367 (15)	0.0168 (14)
C16	0.0893 (19)	0.054 (2)	0.0497 (14)	−0.0081 (15)	−0.0184 (13)	−0.0075 (12)
C17	0.0836 (18)	0.080 (2)	0.0302 (11)	−0.0318 (16)	−0.0193 (12)	0.0020 (11)
C19	0.0387 (11)	0.0428 (14)	0.0248 (9)	−0.0140 (10)	−0.0070 (8)	0.0025 (8)
C20	0.0378 (11)	0.0470 (15)	0.0287 (10)	−0.0140 (10)	−0.0055 (8)	0.0012 (9)
C21	0.0462 (12)	0.0481 (15)	0.0247 (10)	−0.0206 (11)	−0.0064 (9)	0.0047 (9)
C22	0.0519 (13)	0.0386 (14)	0.0315 (10)	−0.0147 (11)	−0.0140 (9)	0.0054 (9)
C23	0.0441 (12)	0.0416 (15)	0.0308 (10)	−0.0077 (10)	−0.0088 (9)	−0.0005 (9)
C24	0.0423 (12)	0.0449 (15)	0.0264 (10)	−0.0136 (10)	−0.0009 (8)	0.0045 (8)
C25	0.0559 (15)	0.077 (2)	0.0435 (13)	−0.0255 (14)	0.0073 (11)	0.0093 (12)
C26	0.0513 (14)	0.066 (2)	0.0489 (14)	0.0000 (13)	0.0002 (11)	−0.0063 (12)
O1	0.0433 (8)	0.0533 (10)	0.0188 (6)	−0.0185 (7)	−0.0048 (6)	0.0037 (6)
O2	0.0561 (9)	0.0598 (12)	0.0250 (7)	−0.0165 (8)	0.0044 (7)	0.0004 (6)
O3	0.0588 (11)	0.1335 (19)	0.0502 (10)	−0.0510 (12)	−0.0144 (9)	0.0094 (10)
O4	0.0634 (10)	0.0447 (11)	0.0443 (9)	0.0036 (8)	−0.0047 (8)	0.0056 (7)
O5	0.0733 (11)	0.0444 (11)	0.0366 (9)	−0.0133 (9)	−0.0053 (8)	0.0110 (7)
O6	0.0582 (10)	0.0533 (11)	0.0370 (8)	−0.0234 (8)	0.0034 (7)	0.0084 (7)

C1—C6	1.330 (2)	C14—H14A	0.9600
C1—O1	1.377 (2)	C14—H14B	0.9600
C1—C2	1.486 (3)	C14—H14C	0.9600
C2—C3	1.534 (3)	C15—H15A	0.9600
C2—H2A	0.9700	C15—H15B	0.9600
C2—H2B	0.9700	C15—H15C	0.9600
C3—C14	1.518 (3)	C16—H16A	0.9600
C3—C15	1.524 (3)	C16—H16B	0.9600
C3—C4	1.525 (3)	C16—H16C	0.9600
C4—C5	1.498 (3)	C17—H17A	0.9600
C4—H4A	0.9700	C17—H17B	0.9600
C4—H4B	0.9700	C17—H17C	0.9600
C5—O2	1.218 (2)	C19—C20	1.383 (2)
C5—C6	1.466 (2)	C19—C24	1.386 (3)
C6—C7	1.511 (3)	C20—C21	1.376 (3)
C7—C8	1.513 (2)	C20—H20	0.9300
C7—C19	1.525 (3)	C21—O6	1.373 (2)
C7—H7	0.9800	C21—C22	1.394 (3)
C8—C13	1.331 (3)	C22—O5	1.358 (2)
C8—C9	1.460 (3)	C22—C23	1.388 (3)
C9—O3	1.213 (2)	C23—C24	1.378 (3)
C9—C10	1.512 (3)	C23—O4	1.379 (3)
C10—C11	1.527 (3)	C24—H24	0.9300
C10—H10A	0.9700	C25—O6	1.419 (3)
C10—H10B	0.9700	C25—H25A	0.9600
C11—C16	1.520 (3)	C25—H25B	0.9600
C11—C12	1.523 (3)	C25—H25C	0.9600
C11—C17	1.532 (3)	C26—O4	1.394 (3)
C12—C13	1.495 (2)	C26—H26A	0.9600
C12—H12A	0.9700	C26—H26B	0.9600
C12—H12B	0.9700	C26—H26C	0.9600
C13—O1	1.374 (2)	O5—H5	0.8200
C6—C1—O1	122.65 (17)	O1—C13—C12	110.98 (15)
C6—C1—C2	125.82 (16)	C3—C14—H14A	109.5
O1—C1—C2	111.53 (15)	C3—C14—H14B	109.5
C1—C2—C3	111.07 (16)	H14A—C14—H14B	109.5
C1—C2—H2A	109.4	C3—C14—H14C	109.5
C3—C2—H2A	109.4	H14A—C14—H14C	109.5
C1—C2—H2B	109.4	H14B—C14—H14C	109.5
C3—C2—H2B	109.4	C3—C15—H15A	109.5
H2A—C2—H2B	108.0	C3—C15—H15B	109.5
C14—C3—C15	109.6 (2)	H15A—C15—H15B	109.5
C14—C3—C4	111.30 (18)	C3—C15—H15C	109.5
C15—C3—C4	109.35 (19)	H15A—C15—H15C	109.5
C14—C3—C2	109.76 (18)	H15B—C15—H15C	109.5
C15—C3—C2	109.56 (18)	C11—C16—H16A	109.5
C4—C3—C2	107.25 (18)	C11—C16—H16B	109.5
C5—C4—C3	116.38 (16)	H16A—C16—H16B	109.5
C5—C4—H4A	108.2	C11—C16—H16C	109.5
C3—C4—H4A	108.2	H16A—C16—H16C	109.5
C5—C4—H4B	108.2	H16B—C16—H16C	109.5
C3—C4—H4B	108.2	C11—C17—H17A	109.5
H4A—C4—H4B	107.3	C11—C17—H17B	109.5
O2—C5—C6	120.52 (19)	H17A—C17—H17B	109.5
O2—C5—C4	120.89 (17)	C11—C17—H17C	109.5
C6—C5—C4	118.57 (17)	H17A—C17—H17C	109.5
C1—C6—C5	117.83 (18)	H17B—C17—H17C	109.5
C1—C6—C7	123.52 (16)	C20—C19—C24	119.02 (19)
C5—C6—C7	118.64 (16)	C20—C19—C7	120.75 (18)
C6—C7—C8	109.05 (15)	C24—C19—C7	120.14 (16)
C6—C7—C19	110.37 (15)	C21—C20—C19	120.34 (19)
C8—C7—C19	112.14 (16)	C21—C20—H20	119.8
C6—C7—H7	108.4	C19—C20—H20	119.8
C8—C7—H7	108.4	O6—C21—C20	125.29 (19)
C19—C7—H7	108.4	O6—C21—C22	113.83 (19)
C13—C8—C9	118.53 (17)	C20—C21—C22	120.88 (18)
C13—C8—C7	122.46 (18)	O5—C22—C23	118.68 (19)
C9—C8—C7	119.01 (17)	O5—C22—C21	122.90 (18)
O3—C9—C8	120.50 (19)	C23—C22—C21	118.42 (19)
O3—C9—C10	120.9 (2)	C24—C23—O4	123.88 (18)
C8—C9—C10	118.48 (18)	C24—C23—C22	120.51 (19)
C9—C10—C11	115.06 (18)	O4—C23—C22	115.60 (19)
C9—C10—H10A	108.5	C23—C24—C19	120.71 (18)
C11—C10—H10A	108.5	C23—C24—H24	119.6
C9—C10—H10B	108.5	C19—C24—H24	119.6
C11—C10—H10B	108.5	O6—C25—H25A	109.5
H10A—C10—H10B	107.5	O6—C25—H25B	109.5
C16—C11—C12	110.94 (19)	H25A—C25—H25B	109.5
C16—C11—C10	110.21 (19)	O6—C25—H25C	109.5
C12—C11—C10	107.87 (18)	H25A—C25—H25C	109.5
C16—C11—C17	108.95 (19)	H25B—C25—H25C	109.5
C12—C11—C17	108.65 (18)	O4—C26—H26A	109.5
C10—C11—C17	110.20 (19)	O4—C26—H26B	109.5
C13—C12—C11	112.93 (17)	H26A—C26—H26B	109.5
C13—C12—H12A	109.0	O4—C26—H26C	109.5
C11—C12—H12A	109.0	H26A—C26—H26C	109.5
C13—C12—H12B	109.0	H26B—C26—H26C	109.5
C11—C12—H12B	109.0	C13—O1—C1	118.10 (14)
H12A—C12—H12B	107.8	C23—O4—C26	116.45 (17)
C8—C13—O1	123.71 (16)	C22—O5—H5	109.5
C8—C13—C12	125.31 (18)	C21—O6—C25	116.86 (18)
C6—C1—C2—C3	−30.4 (3)	C10—C11—C12—C13	−48.2 (2)
O1—C1—C2—C3	150.19 (18)	C17—C11—C12—C13	−167.64 (19)
C1—C2—C3—C14	−69.1 (2)	C9—C8—C13—O1	−173.90 (19)
C1—C2—C3—C15	170.5 (2)	C7—C8—C13—O1	5.3 (3)
C1—C2—C3—C4	51.9 (2)	C9—C8—C13—C12	5.7 (3)
C14—C3—C4—C5	71.9 (2)	C7—C8—C13—C12	−175.1 (2)
C15—C3—C4—C5	−166.9 (2)	C11—C12—C13—C8	22.5 (3)
C2—C3—C4—C5	−48.2 (3)	C11—C12—C13—O1	−157.83 (18)
C3—C4—C5—O2	−162.6 (2)	C6—C7—C19—C20	−102.2 (2)
C3—C4—C5—C6	19.2 (3)	C8—C7—C19—C20	136.03 (18)
O1—C1—C6—C5	177.92 (18)	C6—C7—C19—C24	74.3 (2)
C2—C1—C6—C5	−1.4 (3)	C8—C7—C19—C24	−47.5 (2)
O1—C1—C6—C7	−3.6 (3)	C24—C19—C20—C21	−3.3 (3)
C2—C1—C6—C7	177.01 (19)	C7—C19—C20—C21	173.18 (18)
O2—C5—C6—C1	−170.53 (19)	C19—C20—C21—O6	−177.93 (18)
C4—C5—C6—C1	7.7 (3)	C19—C20—C21—C22	2.2 (3)
O2—C5—C6—C7	11.0 (3)	O6—C21—C22—O5	0.7 (3)
C4—C5—C6—C7	−170.83 (19)	C20—C21—C22—O5	−179.44 (18)
C1—C6—C7—C8	7.4 (3)	O6—C21—C22—C23	−178.83 (17)
C5—C6—C7—C8	−174.20 (17)	C20—C21—C22—C23	1.1 (3)
C1—C6—C7—C19	−116.2 (2)	O5—C22—C23—C24	177.31 (19)
C5—C6—C7—C19	62.2 (2)	C21—C22—C23—C24	−3.2 (3)
C6—C7—C8—C13	−8.1 (3)	O5—C22—C23—O4	−1.7 (3)
C19—C7—C8—C13	114.5 (2)	C21—C22—C23—O4	177.83 (18)
C6—C7—C8—C9	171.07 (18)	O4—C23—C24—C19	−179.03 (18)
C19—C7—C8—C9	−66.4 (2)	C22—C23—C24—C19	2.1 (3)
C13—C8—C9—O3	172.1 (2)	C20—C19—C24—C23	1.2 (3)
C7—C8—C9—O3	−7.1 (3)	C7—C19—C24—C23	−175.31 (18)
C13—C8—C9—C10	−4.4 (3)	C8—C13—O1—C1	−0.4 (3)
C7—C8—C9—C10	176.45 (19)	C12—C13—O1—C1	179.94 (16)
O3—C9—C10—C11	158.3 (2)	C6—C1—O1—C13	−0.5 (3)
C8—C9—C10—C11	−25.3 (3)	C2—C1—O1—C13	178.95 (17)
C9—C10—C11—C16	−70.9 (3)	C24—C23—O4—C26	27.8 (3)
C9—C10—C11—C12	50.4 (3)	C22—C23—O4—C26	−153.2 (2)
C9—C10—C11—C17	168.8 (2)	C20—C21—O6—C25	0.3 (3)
C16—C11—C12—C13	72.6 (2)	C22—C21—O6—C25	−179.86 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O2i	0.82	2.02	2.762 (2)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O2i	0.82	2.02	2.762 (2)	151

Symmetry code: (i) .