Brusatol.

The title compound, C(26)H(32)O(11), is composed of an α,β-unsaturated cyclo-hexa-none ring (A), two cyclo-hexane rings (B and C), a six-membered lactone ring (D) and tetra-hydro-furan ring (E). Ring A exists in a half-chair conformation with a C atom displaced by 0.679 (2) Å from the mean plane through the remaining five atoms. Ring B exists in a normal chair conformation. Both rings C and D exist in a twisted-chair conformation due to the O-atom bridge and the carbonyl group in rings C and D, respectively. Ring E shows an envelope conformation with a C atom displaced by 0.761 (1) Å from the mean plane through the remaining five atoms. The ring junctions are A/B trans, B/C trans, C/D cis and D/E cis. An intra-molecular O-H⋯O hydrogen bond occurs. In the crystal, O-H⋯O hydrogen bonds involving the hy-droxy, lactone and ester groups and C-H⋯O inter-actions are observed.

Related literature

For the isolation of brusatol, see: Sim et al. (1968 ▶); Kim et al. (2004 ▶). For its anti­cancer activity, see: Zhao et al. (2011 ▶) and for its anti­viral activity, see: Yan et al. (2010 ▶). For the enhancement of the efficacy for chemotherapy, see: Ren et al. (2011 ▶). For the crystal structure of bruceine A, see: Feng et al. 2010 ▶. For the absolute configuration of simalikalactone D, see: Moher et al. (1992 ▶).

Experimental

Crystal data

C26H32O11

M = 520.52

Orthorhombic,

a = 6.7162 (1) Å

b = 13.6796 (2) Å

c = 25.9859 (5) Å

V = 2387.45 (7) Å3

Z = 4

Cu Kα radiation

μ = 0.96 mm−1

T = 288 K

0.44 × 0.15 × 0.11 mm

Data collection

Oxford Gemini S Ultra Sapphire CCD diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.748, T max = 1.000

4961 measured reflections

3380 independent reflections

3182 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.085

S = 1.03

3380 reflections

338 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.18 e Å−3

Absolute structure: Flack (1983 ▶), 1167 Friedel pairs

Flack parameter: −0.07 (19)

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: XP in SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812018582/vm2168sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018582/vm2168Isup2.hkl

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

C26H32O11	Dx = 1.448 Mg m−3
Mr = 520.52	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P212121	Cell parameters from 2860 reflections
a = 6.7162 (1) Å	θ = 3.2–62.6°
b = 13.6796 (2) Å	µ = 0.96 mm−1
c = 25.9859 (5) Å	T = 288 K
V = 2387.45 (7) Å3	Needle, colourless
Z = 4	0.44 × 0.15 × 0.11 mm
F(000) = 1104

Oxford Gemini S Ultra Sapphire CCD diffractometer	3380 independent reflections
Radiation source: fine-focus sealed tube	3182 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.020
ω scan	θmax = 62.6°, θmin = 3.2°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	h = −7→6
Tmin = 0.748, Tmax = 1.000	k = −13→15
4961 measured reflections	l = −29→29

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.032	w = 1/[σ2(Fo2) + (0.0463P)2 + 0.5393P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.085	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 0.27 e Å−3
3380 reflections	Δρmin = −0.18 e Å−3
338 parameters	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0070 (4)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1167 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: −0.07 (19)

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
O1	0.6704 (3)	0.54720 (14)	0.02225 (7)	0.0561 (6)
O2	0.7863 (3)	0.37039 (16)	−0.00367 (7)	0.0551 (5)
H2A	0.7975	0.4234	−0.0181	0.094 (15)*
O3	0.0404 (3)	0.54519 (13)	0.14364 (6)	0.0441 (5)
H3A	−0.0296	0.5919	0.1516	0.080 (12)*
O4	0.2361 (3)	0.56662 (12)	0.27424 (6)	0.0411 (4)
H4A	0.2887	0.6182	0.2656	0.069 (11)*
O5	−0.2473 (3)	0.51540 (14)	0.30530 (8)	0.0653 (6)
O6	−0.0670 (2)	0.39701 (16)	0.34093 (6)	0.0505 (5)
O7	−0.1327 (2)	0.40828 (12)	0.21639 (6)	0.0342 (4)
O8	0.4711 (2)	0.23809 (11)	0.21922 (6)	0.0349 (4)
O9	0.6417 (3)	0.25571 (13)	0.28957 (6)	0.0424 (4)
O10	0.3429 (2)	0.35608 (10)	0.33806 (5)	0.0281 (3)
O11	0.2397 (3)	0.20076 (11)	0.33187 (6)	0.0389 (4)
C1	0.5140 (4)	0.50092 (16)	0.10202 (8)	0.0332 (5)
H1A	0.4364	0.5605	0.0990	0.040*
H1B	0.6112	0.5104	0.1292	0.040*
C2	0.6203 (4)	0.48223 (18)	0.05223 (9)	0.0377 (6)
C3	0.6762 (4)	0.38148 (18)	0.04044 (9)	0.0370 (6)
C4	0.6333 (4)	0.30630 (17)	0.07122 (8)	0.0333 (5)
C5	0.5044 (3)	0.32145 (15)	0.11842 (8)	0.0273 (5)
H5A	0.5971	0.3306	0.1471	0.033*
C6	0.3745 (4)	0.23359 (15)	0.13322 (8)	0.0311 (5)
H6A	0.2654	0.2271	0.1090	0.037*
H6B	0.4532	0.1742	0.1319	0.037*
C7	0.2931 (3)	0.24785 (15)	0.18675 (8)	0.0276 (5)
H7A	0.2018	0.1940	0.1946	0.033*
C8	0.1859 (3)	0.34436 (15)	0.19626 (8)	0.0237 (5)
C9	0.2988 (3)	0.43333 (15)	0.17275 (8)	0.0247 (5)
H9A	0.4203	0.4388	0.1934	0.030*
C10	0.3752 (3)	0.41578 (15)	0.11664 (8)	0.0256 (5)
C11	0.1883 (4)	0.53042 (16)	0.18209 (8)	0.0309 (5)
H11A	0.2859	0.5833	0.1788	0.037*
C12	0.0966 (3)	0.53777 (15)	0.23619 (8)	0.0293 (5)
H12A	−0.0104	0.5864	0.2352	0.035*
C13	0.0083 (3)	0.44045 (16)	0.25471 (8)	0.0293 (5)
C14	0.1578 (3)	0.35654 (15)	0.25474 (8)	0.0236 (4)
H14A	0.0874	0.2983	0.2671	0.028*
C15	0.3574 (3)	0.35998 (15)	0.28264 (7)	0.0250 (4)
H15A	0.4201	0.4225	0.2738	0.030*
C16	0.4981 (4)	0.27969 (16)	0.26507 (8)	0.0299 (5)
C18	0.7205 (4)	0.2074 (2)	0.06165 (10)	0.0464 (7)
H18A	0.7984	0.2089	0.0307	0.070*
H18B	0.6152	0.1605	0.0580	0.070*
H18C	0.8038	0.1893	0.0901	0.070*
C19	0.2138 (4)	0.40703 (18)	0.07452 (8)	0.0340 (5)
H19A	0.2763	0.3965	0.0418	0.051*
H19B	0.1371	0.4662	0.0734	0.051*
H19C	0.1278	0.3530	0.0823	0.051*
C20	−0.0349 (3)	0.34250 (16)	0.18165 (8)	0.0302 (5)
H20A	−0.0530	0.3637	0.1463	0.036*
H20B	−0.0884	0.2770	0.1852	0.036*
C21	−0.1136 (4)	0.45655 (17)	0.30335 (9)	0.0355 (6)
C22	−0.1880 (5)	0.4031 (3)	0.38682 (10)	0.0779 (11)
H22A	−0.1412	0.3565	0.4117	0.117*
H22B	−0.3240	0.3889	0.3783	0.117*
H22C	−0.1790	0.4677	0.4010	0.117*
C1'	0.2828 (3)	0.27079 (16)	0.35871 (8)	0.0308 (5)
C2'	0.2793 (4)	0.26745 (17)	0.41472 (8)	0.0365 (6)
H2'A	0.2646	0.2051	0.4284	0.044*
C3'	0.2934 (4)	0.33837 (18)	0.44969 (9)	0.0384 (6)
C4'	0.3105 (5)	0.44546 (19)	0.43916 (10)	0.0527 (7)
H4'A	0.3144	0.4562	0.4027	0.079*
H4'B	0.4305	0.4701	0.4545	0.079*
H4'C	0.1977	0.4788	0.4536	0.079*
C5'	0.2881 (5)	0.3129 (2)	0.50613 (9)	0.0623 (9)
H5'A	0.2802	0.2432	0.5100	0.093*
H5'B	0.1739	0.3427	0.5218	0.093*
H5'C	0.4070	0.3365	0.5225	0.093*

	U11	U22	U33	U12	U13	U23
O1	0.0727 (14)	0.0511 (11)	0.0444 (10)	−0.0068 (11)	0.0227 (11)	0.0081 (9)
O2	0.0584 (12)	0.0674 (13)	0.0396 (10)	−0.0005 (11)	0.0244 (9)	−0.0064 (10)
O3	0.0530 (11)	0.0436 (10)	0.0356 (9)	0.0246 (9)	−0.0004 (8)	0.0049 (7)
O4	0.0518 (10)	0.0336 (9)	0.0378 (9)	−0.0135 (9)	0.0035 (8)	−0.0034 (7)
O5	0.0682 (14)	0.0472 (11)	0.0805 (14)	0.0163 (11)	0.0418 (12)	0.0069 (10)
O6	0.0322 (9)	0.0896 (14)	0.0296 (8)	0.0093 (10)	0.0090 (8)	0.0096 (9)
O7	0.0231 (7)	0.0424 (9)	0.0372 (8)	0.0033 (7)	−0.0018 (7)	−0.0045 (7)
O8	0.0376 (9)	0.0365 (8)	0.0308 (8)	0.0146 (8)	−0.0027 (8)	−0.0025 (7)
O9	0.0359 (9)	0.0523 (10)	0.0388 (9)	0.0117 (8)	−0.0061 (8)	0.0073 (8)
O10	0.0336 (8)	0.0287 (8)	0.0219 (7)	−0.0042 (7)	−0.0026 (7)	0.0022 (6)
O11	0.0555 (11)	0.0297 (8)	0.0314 (8)	−0.0101 (8)	−0.0033 (8)	−0.0006 (7)
C1	0.0356 (12)	0.0338 (12)	0.0301 (11)	−0.0011 (11)	0.0055 (10)	−0.0005 (9)
C2	0.0378 (13)	0.0440 (14)	0.0311 (12)	−0.0058 (12)	0.0058 (11)	0.0008 (11)
C3	0.0319 (12)	0.0496 (15)	0.0295 (11)	0.0001 (11)	0.0092 (10)	−0.0069 (11)
C4	0.0285 (11)	0.0406 (13)	0.0307 (11)	0.0020 (11)	−0.0014 (11)	−0.0105 (11)
C5	0.0256 (11)	0.0306 (11)	0.0259 (10)	0.0027 (10)	−0.0019 (10)	−0.0041 (9)
C6	0.0355 (12)	0.0257 (11)	0.0321 (11)	0.0020 (11)	0.0011 (11)	−0.0056 (9)
C7	0.0275 (11)	0.0249 (10)	0.0303 (11)	−0.0003 (9)	−0.0016 (10)	−0.0014 (9)
C8	0.0234 (11)	0.0241 (11)	0.0235 (10)	−0.0005 (9)	0.0000 (9)	−0.0037 (8)
C9	0.0257 (10)	0.0254 (10)	0.0230 (10)	−0.0007 (9)	−0.0004 (9)	−0.0014 (8)
C10	0.0239 (10)	0.0283 (11)	0.0248 (11)	0.0021 (10)	0.0012 (9)	−0.0004 (9)
C11	0.0362 (12)	0.0241 (10)	0.0323 (11)	0.0037 (10)	0.0055 (10)	0.0037 (9)
C12	0.0328 (12)	0.0235 (11)	0.0316 (11)	0.0052 (10)	0.0058 (10)	0.0007 (9)
C13	0.0266 (10)	0.0305 (12)	0.0307 (11)	−0.0006 (10)	0.0038 (10)	−0.0009 (9)
C14	0.0246 (10)	0.0229 (10)	0.0234 (10)	−0.0025 (9)	0.0009 (9)	0.0010 (8)
C15	0.0271 (10)	0.0270 (10)	0.0209 (9)	−0.0019 (9)	−0.0010 (9)	0.0042 (9)
C16	0.0308 (12)	0.0301 (12)	0.0289 (11)	0.0009 (10)	0.0015 (10)	0.0068 (9)
C18	0.0416 (14)	0.0490 (15)	0.0487 (15)	0.0056 (13)	0.0082 (13)	−0.0169 (12)
C19	0.0337 (12)	0.0423 (13)	0.0260 (11)	0.0037 (12)	−0.0039 (10)	−0.0007 (10)
C20	0.0257 (11)	0.0352 (12)	0.0299 (11)	−0.0013 (10)	−0.0024 (10)	−0.0015 (9)
C21	0.0325 (12)	0.0319 (12)	0.0421 (13)	−0.0048 (11)	0.0101 (11)	−0.0058 (11)
C22	0.0446 (17)	0.157 (4)	0.0324 (15)	0.009 (2)	0.0143 (13)	0.0076 (19)
C1'	0.0333 (12)	0.0300 (12)	0.0291 (11)	−0.0013 (11)	0.0003 (10)	0.0034 (10)
C2'	0.0463 (14)	0.0349 (12)	0.0284 (11)	0.0027 (12)	−0.0004 (11)	0.0069 (10)
C3'	0.0368 (13)	0.0484 (14)	0.0299 (12)	0.0042 (12)	−0.0002 (11)	−0.0020 (11)
C4'	0.0618 (18)	0.0455 (15)	0.0508 (16)	−0.0112 (15)	0.0082 (15)	−0.0182 (13)
C5'	0.081 (2)	0.077 (2)	0.0292 (13)	0.019 (2)	−0.0019 (15)	−0.0030 (14)

O1—C2	1.229 (3)	C9—C11	1.541 (3)
O2—C3	1.372 (3)	C9—C10	1.564 (3)
O2—H2A	0.8200	C9—H9A	0.9800
O3—C11	1.423 (3)	C10—C19	1.545 (3)
O3—H3A	0.8200	C11—C12	1.538 (3)
O4—C12	1.418 (3)	C11—H11A	0.9800
O4—H4A	0.8200	C12—C13	1.535 (3)
O5—C21	1.207 (3)	C12—H12A	0.9800
O6—C21	1.310 (3)	C13—C21	1.522 (3)
O6—C22	1.445 (3)	C13—C14	1.525 (3)
O7—C20	1.434 (3)	C14—C15	1.525 (3)
O7—C13	1.443 (3)	C14—H14A	0.9800
O8—C16	1.333 (3)	C15—C16	1.519 (3)
O8—C7	1.469 (3)	C15—H15A	0.9800
O9—C16	1.201 (3)	C18—H18A	0.9600
O10—C1'	1.346 (3)	C18—H18B	0.9600
O10—C15	1.444 (2)	C18—H18C	0.9600
O11—C1'	1.220 (3)	C19—H19A	0.9600
C1—C2	1.500 (3)	C19—H19B	0.9600
C1—C10	1.539 (3)	C19—H19C	0.9600
C1—H1A	0.9700	C20—H20A	0.9700
C1—H1B	0.9700	C20—H20B	0.9700
C2—C3	1.461 (3)	C22—H22A	0.9600
C3—C4	1.334 (3)	C22—H22B	0.9600
C4—C18	1.495 (3)	C22—H22C	0.9600
C4—C5	1.516 (3)	C1'—C2'	1.456 (3)
C5—C6	1.534 (3)	C2'—C3'	1.333 (3)
C5—C10	1.556 (3)	C2'—H2'A	0.9300
C5—H5A	0.9800	C3'—C4'	1.495 (4)
C6—C7	1.507 (3)	C3'—C5'	1.508 (3)
C6—H6A	0.9700	C4'—H4'A	0.9600
C6—H6B	0.9700	C4'—H4'B	0.9600
C7—C8	1.524 (3)	C4'—H4'C	0.9600
C7—H7A	0.9800	C5'—H5'A	0.9600
C8—C20	1.531 (3)	C5'—H5'B	0.9600
C8—C14	1.540 (3)	C5'—H5'C	0.9600
C8—C9	1.559 (3)
C3—O2—H2A	109.5	O7—C13—C21	105.32 (18)
C11—O3—H3A	109.5	O7—C13—C14	101.70 (16)
C12—O4—H4A	109.5	C21—C13—C14	117.56 (19)
C21—O6—C22	116.4 (2)	O7—C13—C12	107.57 (17)
C20—O7—C13	108.99 (16)	C21—C13—C12	110.05 (18)
C16—O8—C7	125.83 (17)	C14—C13—C12	113.48 (18)
C1'—O10—C15	116.72 (16)	C15—C14—C13	123.77 (18)
C2—C1—C10	111.86 (18)	C15—C14—C8	111.37 (17)
C2—C1—H1A	109.2	C13—C14—C8	99.31 (16)
C10—C1—H1A	109.2	C15—C14—H14A	107.1
C2—C1—H1B	109.2	C13—C14—H14A	107.1
C10—C1—H1B	109.2	C8—C14—H14A	107.1
H1A—C1—H1B	107.9	O10—C15—C16	108.35 (16)
O1—C2—C3	118.6 (2)	O10—C15—C14	114.43 (17)
O1—C2—C1	123.6 (2)	C16—C15—C14	112.44 (17)
C3—C2—C1	117.6 (2)	O10—C15—H15A	107.1
C4—C3—O2	122.1 (2)	C16—C15—H15A	107.1
C4—C3—C2	123.1 (2)	C14—C15—H15A	107.1
O2—C3—C2	114.7 (2)	O9—C16—O8	117.8 (2)
C3—C4—C18	120.9 (2)	O9—C16—C15	122.5 (2)
C3—C4—C5	120.2 (2)	O8—C16—C15	119.52 (18)
C18—C4—C5	118.8 (2)	C4—C18—H18A	109.5
C4—C5—C6	114.88 (17)	C4—C18—H18B	109.5
C4—C5—C10	114.09 (17)	H18A—C18—H18B	109.5
C6—C5—C10	109.88 (17)	C4—C18—H18C	109.5
C4—C5—H5A	105.7	H18A—C18—H18C	109.5
C6—C5—H5A	105.7	H18B—C18—H18C	109.5
C10—C5—H5A	105.7	C10—C19—H19A	109.5
C7—C6—C5	109.64 (17)	C10—C19—H19B	109.5
C7—C6—H6A	109.7	H19A—C19—H19B	109.5
C5—C6—H6A	109.7	C10—C19—H19C	109.5
C7—C6—H6B	109.7	H19A—C19—H19C	109.5
C5—C6—H6B	109.7	H19B—C19—H19C	109.5
H6A—C6—H6B	108.2	O7—C20—C8	106.08 (17)
O8—C7—C6	102.92 (17)	O7—C20—H20A	110.5
O8—C7—C8	111.71 (16)	C8—C20—H20A	110.5
C6—C7—C8	115.66 (18)	O7—C20—H20B	110.5
O8—C7—H7A	108.8	C8—C20—H20B	110.5
C6—C7—H7A	108.8	H20A—C20—H20B	108.7
C8—C7—H7A	108.8	O5—C21—O6	124.2 (2)
C7—C8—C20	113.77 (18)	O5—C21—C13	122.1 (2)
C7—C8—C14	108.16 (17)	O6—C21—C13	113.6 (2)
C20—C8—C14	97.32 (17)	O6—C22—H22A	109.5
C7—C8—C9	112.53 (17)	O6—C22—H22B	109.5
C20—C8—C9	112.77 (17)	H22A—C22—H22B	109.5
C14—C8—C9	111.21 (16)	O6—C22—H22C	109.5
C11—C9—C8	112.15 (17)	H22A—C22—H22C	109.5
C11—C9—C10	115.92 (17)	H22B—C22—H22C	109.5
C8—C9—C10	113.89 (16)	O11—C1'—O10	121.61 (19)
C11—C9—H9A	104.5	O11—C1'—C2'	122.9 (2)
C8—C9—H9A	104.5	O10—C1'—C2'	115.5 (2)
C10—C9—H9A	104.5	C3'—C2'—C1'	131.1 (2)
C1—C10—C19	107.97 (17)	C3'—C2'—H2'A	114.4
C1—C10—C5	107.28 (17)	C1'—C2'—H2'A	114.4
C19—C10—C5	110.36 (17)	C2'—C3'—C4'	126.4 (2)
C1—C10—C9	108.21 (17)	C2'—C3'—C5'	119.6 (2)
C19—C10—C9	116.26 (18)	C4'—C3'—C5'	114.0 (2)
C5—C10—C9	106.41 (16)	C3'—C4'—H4'A	109.5
O3—C11—C12	110.70 (18)	C3'—C4'—H4'B	109.5
O3—C11—C9	110.37 (17)	H4'A—C4'—H4'B	109.5
C12—C11—C9	113.15 (17)	C3'—C4'—H4'C	109.5
O3—C11—H11A	107.5	H4'A—C4'—H4'C	109.5
C12—C11—H11A	107.5	H4'B—C4'—H4'C	109.5
C9—C11—H11A	107.5	C3'—C5'—H5'A	109.5
O4—C12—C13	106.15 (17)	C3'—C5'—H5'B	109.5
O4—C12—C11	113.04 (18)	H5'A—C5'—H5'B	109.5
C13—C12—C11	112.62 (17)	C3'—C5'—H5'C	109.5
O4—C12—H12A	108.3	H5'A—C5'—H5'C	109.5
C13—C12—H12A	108.3	H5'B—C5'—H5'C	109.5
C11—C12—H12A	108.3
C10—C1—C2—O1	149.1 (2)	O3—C11—C12—C13	85.9 (2)
C10—C1—C2—C3	−34.3 (3)	C9—C11—C12—C13	−38.6 (3)
O1—C2—C3—C4	178.2 (2)	C20—O7—C13—C21	−148.07 (18)
C1—C2—C3—C4	1.5 (4)	C20—O7—C13—C14	−24.9 (2)
O1—C2—C3—O2	1.5 (4)	C20—O7—C13—C12	94.6 (2)
C1—C2—C3—O2	−175.2 (2)	O4—C12—C13—O7	−179.23 (16)
O2—C3—C4—C18	6.0 (4)	C11—C12—C13—O7	−55.0 (2)
C2—C3—C4—C18	−170.5 (2)	O4—C12—C13—C21	66.5 (2)
O2—C3—C4—C5	−177.6 (2)	C11—C12—C13—C21	−169.28 (19)
C2—C3—C4—C5	6.0 (4)	O4—C12—C13—C14	−67.5 (2)
C3—C4—C5—C6	148.1 (2)	C11—C12—C13—C14	56.6 (2)
C18—C4—C5—C6	−35.4 (3)	O7—C13—C14—C15	170.06 (18)
C3—C4—C5—C10	19.9 (3)	C21—C13—C14—C15	−75.6 (3)
C18—C4—C5—C10	−163.6 (2)	C12—C13—C14—C15	54.8 (3)
C4—C5—C6—C7	166.34 (18)	O7—C13—C14—C8	46.42 (19)
C10—C5—C6—C7	−63.4 (2)	C21—C13—C14—C8	160.78 (19)
C16—O8—C7—C6	152.39 (19)	C12—C13—C14—C8	−68.8 (2)
C16—O8—C7—C8	27.7 (3)	C7—C8—C14—C15	61.3 (2)
C5—C6—C7—O8	−69.4 (2)	C20—C8—C14—C15	179.31 (17)
C5—C6—C7—C8	52.7 (3)	C9—C8—C14—C15	−62.8 (2)
O8—C7—C8—C20	−156.51 (17)	C7—C8—C14—C13	−166.73 (17)
C6—C7—C8—C20	86.2 (2)	C20—C8—C14—C13	−48.70 (19)
O8—C7—C8—C14	−49.6 (2)	C9—C8—C14—C13	69.2 (2)
C6—C7—C8—C14	−166.86 (19)	C1'—O10—C15—C16	−57.0 (2)
O8—C7—C8—C9	73.7 (2)	C1'—O10—C15—C14	69.3 (2)
C6—C7—C8—C9	−43.6 (2)	C13—C14—C15—O10	71.0 (3)
C7—C8—C9—C11	179.43 (18)	C8—C14—C15—O10	−170.89 (16)
C20—C8—C9—C11	49.1 (2)	C13—C14—C15—C16	−164.80 (18)
C14—C8—C9—C11	−59.0 (2)	C8—C14—C15—C16	−46.7 (2)
C7—C8—C9—C10	45.3 (2)	C7—O8—C16—O9	171.5 (2)
C20—C8—C9—C10	−85.0 (2)	C7—O8—C16—C15	−13.0 (3)
C14—C8—C9—C10	166.82 (17)	O10—C15—C16—O9	−35.3 (3)
C2—C1—C10—C19	−62.7 (2)	C14—C15—C16—O9	−162.7 (2)
C2—C1—C10—C5	56.3 (2)	O10—C15—C16—O8	149.45 (18)
C2—C1—C10—C9	170.74 (19)	C14—C15—C16—O8	22.0 (3)
C4—C5—C10—C1	−49.7 (2)	C13—O7—C20—C8	−6.9 (2)
C6—C5—C10—C1	179.60 (17)	C7—C8—C20—O7	148.59 (17)
C4—C5—C10—C19	67.7 (2)	C14—C8—C20—O7	35.0 (2)
C6—C5—C10—C19	−63.0 (2)	C9—C8—C20—O7	−81.7 (2)
C4—C5—C10—C9	−165.37 (18)	C22—O6—C21—O5	0.9 (4)
C6—C5—C10—C9	64.0 (2)	C22—O6—C21—C13	−175.2 (2)
C11—C9—C10—C1	57.6 (2)	O7—C13—C21—O5	−61.0 (3)
C8—C9—C10—C1	−170.06 (18)	C14—C13—C21—O5	−173.3 (2)
C11—C9—C10—C19	−64.1 (3)	C12—C13—C21—O5	54.7 (3)
C8—C9—C10—C19	68.3 (2)	O7—C13—C21—O6	115.2 (2)
C11—C9—C10—C5	172.60 (18)	C14—C13—C21—O6	2.8 (3)
C8—C9—C10—C5	−55.0 (2)	C12—C13—C21—O6	−129.1 (2)
C8—C9—C11—O3	−84.4 (2)	C15—O10—C1'—O11	−1.1 (3)
C10—C9—C11—O3	48.7 (2)	C15—O10—C1'—C2'	177.03 (19)
C8—C9—C11—C12	40.2 (2)	O11—C1'—C2'—C3'	−169.2 (3)
C10—C9—C11—C12	173.40 (18)	O10—C1'—C2'—C3'	12.7 (4)
O3—C11—C12—O4	−153.84 (17)	C1'—C2'—C3'—C4'	2.3 (5)
C9—C11—C12—O4	81.7 (2)	C1'—C2'—C3'—C5'	−179.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1	0.82	2.17	2.629 (3)	116
O3—H3A···O11i	0.82	2.09	2.911 (2)	173
O4—H4A···O9ii	0.82	2.41	3.180 (2)	157
O4—H4A···O8ii	0.82	2.33	3.066 (2)	149
C11—H11A···O9ii	0.98	2.54	3.368 (4)	142
C5′—H5′B···O1iii	0.96	2.76	3.650 (3)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O1	0.82	2.17	2.629 (3)	116
O3—H3A⋯O11i	0.82	2.09	2.911 (2)	173
O4—H4A⋯O9ii	0.82	2.41	3.180 (2)	157
O4—H4A⋯O8ii	0.82	2.33	3.066 (2)	149
C11—H11A⋯O9ii	0.98	2.54	3.368 (4)	142
C5′—H5′B⋯O1iii	0.96	2.76	3.650 (3)	155

Symmetry codes: (i) ; (ii) ; (iii) .