9-(4-Hy­droxy-3,5-dimeth­oxy­phen­yl)-3,3,6,6-tetra­methyl-3,4,5,6,7,9-hexa­hydro-1H-xanthene-1,8(2H)-dione

In the title compound, C₂₅H₃₀O₆, the two fused cyclo­hexa­none 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.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.051
• wR factor = 0.157
• Data-to-parameter ratio = 18.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......      0.950

Alert level C
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          2
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600        149
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600        123

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT007_ALERT_5_G Note: Number of Unrefined D-H Atoms ............          1
PLAT793_ALERT_4_G The Model has Chirality at C7      (Verify) ....          S

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

---

S1. Comment

Xanthene is the parent compound of a number of naturally occurring substances and some synthetic dyes. Xanthene derivatives are used as dyes (Hilderbrand & Weissleder, 2007) and they possess biological properties like antibacterial, antiviral, anti-inflammatory (Jonathan et al., 1988) activities and are therefore used in medicine. Ehretianone, a quinonoid xanthene was reported to possess antisnake venom activity (Selvanayagam et al., 1996; Lambert et al., 1997; Poupelin et al., 1978; Hideo, 1981).

In the title compound (I), the cyclohexenone rings C1–C6 and C8–C13 both adopt an envelope conformation. In contrast, the pyran ring (O1/C1/C6/C8/C13) is almost planar with a slight deviation of C7 (0.99 Å) from the (C8/C13/O1/C1/C6) plane. The pyran ring and phenyl ring are almost perpendicular to one another making a dihedral angle of 86.32 (2)°. The bond lengths and angles are consistent with the reported structure (Odabasoglu et al., 2008; Mehdi et al., 2011). In the crystal structure, a relatively short intermolecular O5—H5···O2 hydrogen bond leads to the observation of centrosymmetrical 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).

S2. Experimental

The title compound was prepared in two stages (Vang & Stankevich, 1960). In the first stage, a mixture of 4-hydroxy-3,5-dimethoxybenzaldehyde (0.5 g, 8 m mol), 5,5-dimethylcyclohexane-1,3-dione (1.15 g, 1.6 mmol) and 10 ml of ethanol was heated to 70°C for about 10 minutes. The reaction mixture was allowed to cool to room temperature and the resulting solid intermediate 2,2'-((4-hydroxy-3,5-dimethoxyphenyl)methylene)bis(3-hydroxy-5,5-dimethylcyclohex-2-enone) was filtered and dried. In the second stage, about 0.5 g of this intermediate were dissolved in 25 ml of ethanol. The content was refluxed together with 15 drops of concentrated hydrochloric acid for 30 minutes with the reaction being monitored by TLC. After completion of the reaction, the reaction mixture was poured into crushed ice and stirred well. The solid separated was filtered, dried and then recrystallized from ethanol to yield colourless crystals of t he title compound (m.p. 490–492 K; yield: 85%).

S3. Refinement

All hydrogen atoms of the title compound were identified from the difference electron map and subsequently treated as riding atoms with distances of d(C–H) = 0.96 Å (for CH₃) with U_iso(H) = 1.5 U_eq(C), d(C–H) = 0.97 Å (for CH₂) with U_iso(H) = 1.2 U_eq(C), d(C–H) = 0.98 Å (for CH) with U_iso(H) = 1.5 U_eq(C) and d(C–H) = 0.93 Å (for aromatic CH) with U_iso(H) = 1.2 U_eq(C). The hydroxyl hydrogen atom was also identified from the difference electron map and was allowed to ride on the parent O atom with d(O–H) = 0.82 Å and U_iso(H) = 1.5 U_eq(O).

Computing details

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 (Sheldrick, 2008).

Figures

	Fig. 1. : Molecular structure of (I), showing displacement ellipsoids at the 30% probability level.
	Fig. 2. : Packing diagram for (I) showing the formation of O—H···O hydrogen bonds between the molecules in the unit cell.

9-(4-Hydroxy-3,5-dimethoxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9- hexahydro-1H-xanthene-1,8(2H)-dione

Crystal data

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) Å^3

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.051	H-atom parameters constrained
wR(F^2) = 0.157	w = 1/[σ^2(Fo^2) + (0.0666P)^2 + 0.3374P] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.008 (2)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O2^i	0.82	2.02	2.762 (2)	151

Symmetry code: (i) −x+1, −y+1, −z.