Neoaustin: a meroterpene produced by Penicillium sp.

The title meroterpene neoaustin {systematic name: (1'S,2'R,3S,7'R,9'S,11'S,12'R)-11'-hydr-oxy-2,2,2',9',12'-penta-methyl-6',15'-dimethyl-ene-2,6-dihydro-13'-oxaspiro-[pyran-3,5'-tetra-cyclo-[7.5.1.0(1,11).0(2,7)]penta-deca-ne]-6,10',14'-trione}, C(25)H(30)O(6), comprises five rings, three six-membered and two five-membered. The absolute configuration was established based on [α(D)] = +166.91° (c 1.21, CH(2)Cl(2)). In the crystal, the mol-ecules are connected into a supra-molecular helical chain via O-H⋯O hydrogen bonds reinforced by C-H⋯O contacts.

Related literature

For related literature, see: dos Santos & Rodrigues-Fo (2002 ▶, 2003 ▶); Maganhi et al. 2009 ▶. For ring conformation analysis, see: Cremer & Pople (1975 ▶); Iulek & Zukerman-Schpector (1997 ▶).

Experimental

Crystal data

C25H30O6

M = 426.49

Orthorhombic,

a = 11.2152 (4) Å

b = 13.2870 (5) Å

c = 14.3914 (7) Å

V = 2144.55 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 290 K

0.49 × 0.39 × 0.21 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: none

18157 measured reflections

2622 independent reflections

2453 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.106

S = 1.07

2622 reflections

286 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.13 e Å−3

Data collection: APEX2, COSMO and BIS (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PARST (Nardelli, 1995 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809006618/tk2374sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006618/tk2374Isup2.hkl

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

C25H30O6	F(000) = 912
Mr = 426.49	Dx = 1.321 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 33851 reflections
a = 11.2152 (4) Å	θ = 1.0–27.4°
b = 13.2870 (5) Å	µ = 0.09 mm−1
c = 14.3914 (7) Å	T = 290 K
V = 2144.55 (15) Å3	Prism, colorless
Z = 4	0.49 × 0.39 × 0.21 mm

Bruker APEXII CCD area-detector diffractometer	2453 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.048
graphite	θmax = 27.0°, θmin = 3.2°
φ and ω scans	h = −14→14
18157 measured reflections	k = −15→16
2622 independent reflections	l = −17→18

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0607P)2 + 0.3107P] where P = (Fo2 + 2Fc2)/3
2622 reflections	(Δ/σ)max < 0.001
286 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.13 e Å−3

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'	0.32891 (19)	0.90837 (15)	0.67021 (13)	0.0371 (4)
C2'	0.45203 (19)	0.93770 (16)	0.71346 (13)	0.0380 (4)
C2	0.74745 (19)	0.93484 (17)	0.92112 (15)	0.0425 (5)
C3'	0.5381 (2)	0.84818 (18)	0.71741 (15)	0.0462 (5)
H3'A	0.5613	0.8301	0.6546	0.055*
H3'B	0.4973	0.7909	0.7444	0.055*
C4'	0.6507 (2)	0.8705 (2)	0.77441 (16)	0.0485 (5)
H4'A	0.6980	0.9201	0.7415	0.058*
H4'B	0.6977	0.8094	0.7788	0.058*
C4	0.5674 (2)	0.82925 (17)	0.93270 (16)	0.0436 (5)
H4	0.5162	0.7834	0.9046	0.052*
C5	0.5873 (2)	0.82231 (18)	1.02291 (17)	0.0493 (5)
H5	0.5532	0.7698	1.0564	0.059*
C5'	0.62593 (18)	0.90991 (16)	0.87378 (14)	0.0378 (4)
C6	0.66206 (19)	0.89585 (17)	1.07096 (15)	0.0431 (5)
C6'	0.53593 (18)	0.99769 (15)	0.86945 (13)	0.0361 (4)
C7'	0.42380 (18)	0.97177 (15)	0.81504 (13)	0.0346 (4)
H7'	0.3896	0.9127	0.8459	0.041*
C8'	0.32623 (19)	1.05317 (15)	0.81811 (14)	0.0375 (4)
H8'A	0.3586	1.1156	0.7940	0.045*
H8'B	0.3035	1.0647	0.8823	0.045*
C9'	0.21293 (19)	1.02470 (16)	0.76119 (14)	0.0385 (4)
C10'	0.18022 (19)	0.91858 (16)	0.79257 (14)	0.0405 (4)
C11'	0.24352 (19)	0.84332 (16)	0.72965 (14)	0.0402 (5)
C12'	0.1604 (2)	0.79507 (18)	0.65534 (17)	0.0523 (6)
H12'	0.1481	0.7246	0.6731	0.063*
C14'	0.3301 (2)	0.85332 (18)	0.57786 (15)	0.0493 (5)
C15'	0.2536 (2)	1.00412 (16)	0.66311 (14)	0.0385 (4)
C16	0.8344 (2)	0.8465 (2)	0.9222 (2)	0.0571 (6)
H16A	0.7958	0.7885	0.9482	0.086*
H16B	0.9027	0.8636	0.9593	0.086*
H16C	0.8596	0.8319	0.8599	0.086*
C17	0.8129 (2)	1.0257 (2)	0.8822 (2)	0.0573 (6)
H17A	0.8738	1.0463	0.9250	0.086*
H17B	0.7575	1.0799	0.8732	0.086*
H17C	0.8487	1.0083	0.8238	0.086*
C18	0.5105 (2)	1.0233 (2)	0.65818 (16)	0.0507 (5)
H18A	0.5192	1.0033	0.5944	0.076*
H18B	0.5875	1.0379	0.6840	0.076*
H18C	0.4613	1.0823	0.6615	0.076*
C19	0.5471 (2)	1.08493 (18)	0.91461 (17)	0.0516 (5)
H19A	0.4854	1.1317	0.9133	0.062*
H19B	0.6166	1.0990	0.9474	0.062*
C20	0.1151 (2)	1.10233 (19)	0.77492 (17)	0.0498 (5)
H20A	0.0473	1.0847	0.7375	0.075*
H20B	0.1439	1.1674	0.7567	0.075*
H20C	0.0922	1.1039	0.8392	0.075*
C21	0.0390 (3)	0.8406 (2)	0.6378 (2)	0.0641 (7)
H21A	−0.0015	0.8026	0.5906	0.096*
H21B	0.0481	0.9090	0.6176	0.096*
H21C	−0.0069	0.8391	0.6941	0.096*
C22	0.2290 (3)	1.05608 (19)	0.58737 (17)	0.0557 (6)
H22A	0.1811	1.1131	0.5910	0.067*
H22B	0.2596	1.0357	0.5303	0.067*
O1	0.72595 (13)	0.95988 (11)	1.02022 (10)	0.0418 (3)
O2	0.66745 (17)	0.90141 (15)	1.15505 (11)	0.0577 (4)
O3	0.11959 (17)	0.89618 (14)	0.85870 (12)	0.0583 (5)
O4	0.30164 (16)	0.76719 (12)	0.78090 (12)	0.0516 (4)
H1O4	0.2520	0.7281	0.8019	0.062*
O5	0.23077 (19)	0.79543 (15)	0.57041 (12)	0.0613 (5)
O6	0.4016 (2)	0.85761 (16)	0.51643 (11)	0.0659 (5)

	U11	U22	U33	U12	U13	U23
C1'	0.0436 (10)	0.0378 (9)	0.0299 (8)	−0.0005 (9)	0.0004 (9)	0.0024 (7)
C2'	0.0402 (10)	0.0421 (10)	0.0317 (9)	0.0003 (9)	0.0038 (8)	−0.0007 (8)
C2	0.0336 (10)	0.0503 (12)	0.0435 (11)	0.0003 (9)	0.0020 (9)	0.0028 (9)
C3'	0.0464 (12)	0.0499 (12)	0.0422 (11)	0.0090 (10)	0.0022 (10)	−0.0110 (9)
C4'	0.0429 (11)	0.0544 (12)	0.0482 (12)	0.0104 (10)	0.0038 (10)	−0.0104 (10)
C4	0.0383 (10)	0.0390 (10)	0.0535 (12)	−0.0006 (9)	−0.0035 (10)	0.0038 (9)
C5	0.0471 (12)	0.0477 (12)	0.0531 (12)	−0.0053 (10)	−0.0009 (11)	0.0148 (10)
C5'	0.0334 (9)	0.0408 (10)	0.0393 (10)	0.0018 (8)	0.0004 (8)	0.0023 (8)
C6	0.0386 (10)	0.0461 (11)	0.0445 (11)	0.0052 (9)	−0.0007 (9)	0.0082 (9)
C6'	0.0365 (9)	0.0385 (10)	0.0332 (9)	0.0030 (8)	0.0015 (8)	0.0028 (7)
C7'	0.0360 (9)	0.0357 (9)	0.0320 (9)	0.0027 (8)	0.0024 (7)	0.0013 (7)
C8'	0.0384 (10)	0.0386 (10)	0.0356 (9)	0.0036 (9)	0.0000 (8)	−0.0013 (7)
C9'	0.0373 (10)	0.0412 (10)	0.0369 (9)	0.0012 (8)	−0.0006 (8)	0.0029 (8)
C10'	0.0387 (10)	0.0460 (11)	0.0368 (10)	−0.0025 (9)	−0.0023 (9)	0.0045 (9)
C11'	0.0440 (11)	0.0361 (10)	0.0405 (10)	−0.0009 (9)	−0.0015 (9)	0.0073 (8)
C12'	0.0624 (14)	0.0418 (11)	0.0526 (12)	−0.0092 (11)	−0.0059 (12)	−0.0023 (10)
C14'	0.0629 (14)	0.0479 (12)	0.0372 (10)	0.0058 (11)	−0.0052 (11)	−0.0036 (9)
C15'	0.0431 (10)	0.0366 (10)	0.0358 (9)	−0.0009 (8)	−0.0033 (9)	0.0025 (8)
C16	0.0382 (11)	0.0655 (15)	0.0676 (15)	0.0106 (11)	−0.0022 (12)	−0.0038 (13)
C17	0.0458 (12)	0.0654 (15)	0.0607 (14)	−0.0140 (12)	0.0047 (12)	0.0108 (12)
C18	0.0514 (12)	0.0591 (13)	0.0416 (11)	−0.0083 (11)	0.0096 (11)	0.0053 (10)
C19	0.0544 (13)	0.0462 (12)	0.0543 (12)	0.0071 (11)	−0.0140 (11)	−0.0064 (10)
C20	0.0426 (11)	0.0535 (13)	0.0533 (12)	0.0095 (11)	−0.0022 (11)	0.0008 (10)
C21	0.0595 (15)	0.0670 (16)	0.0657 (16)	−0.0123 (14)	−0.0194 (13)	−0.0019 (13)
C22	0.0767 (17)	0.0485 (12)	0.0418 (11)	0.0053 (12)	−0.0051 (12)	0.0092 (10)
O1	0.0388 (7)	0.0459 (8)	0.0405 (7)	−0.0034 (7)	−0.0043 (6)	0.0034 (6)
O2	0.0596 (10)	0.0723 (11)	0.0413 (8)	0.0051 (10)	0.0001 (8)	0.0080 (8)
O3	0.0566 (10)	0.0651 (11)	0.0531 (9)	−0.0069 (9)	0.0156 (9)	0.0095 (8)
O4	0.0579 (9)	0.0399 (8)	0.0569 (9)	−0.0017 (7)	−0.0022 (8)	0.0156 (7)
O5	0.0738 (12)	0.0619 (10)	0.0482 (9)	−0.0079 (10)	−0.0056 (9)	−0.0151 (8)
O6	0.0809 (13)	0.0804 (13)	0.0363 (8)	0.0021 (11)	0.0085 (9)	−0.0096 (8)

C1'—C14'	1.517 (3)	C9'—C20	1.519 (3)
C1'—C15'	1.530 (3)	C9'—C10'	1.525 (3)
C1'—C11'	1.548 (3)	C10'—O3	1.207 (3)
C1'—C2'	1.564 (3)	C10'—C11'	1.524 (3)
C2'—C3'	1.533 (3)	C11'—O4	1.411 (3)
C2'—C18	1.535 (3)	C11'—C12'	1.557 (3)
C2'—C7'	1.563 (3)	C12'—O5	1.455 (3)
C2—O1	1.484 (3)	C12'—C21	1.511 (4)
C2—C17	1.520 (3)	C12'—H12'	0.9800
C2—C16	1.526 (3)	C14'—O6	1.195 (3)
C2—C5'	1.559 (3)	C14'—O5	1.358 (3)
C3'—C4'	1.534 (3)	C15'—C22	1.319 (3)
C3'—H3'A	0.9700	C16—H16A	0.9600
C3'—H3'B	0.9700	C16—H16B	0.9600
C4'—C5'	1.548 (3)	C16—H16C	0.9600
C4'—H4'A	0.9700	C17—H17A	0.9600
C4'—H4'B	0.9700	C17—H17B	0.9600
C4—C5	1.321 (3)	C17—H17C	0.9600
C4—C5'	1.516 (3)	C18—H18A	0.9600
C4—H4	0.9300	C18—H18B	0.9600
C5—C6	1.461 (3)	C18—H18C	0.9600
C5—H5	0.9300	C19—H19A	0.9300
C5'—C6'	1.544 (3)	C19—H19B	0.9300
C6—O2	1.214 (3)	C20—H20A	0.9600
C6—O1	1.331 (3)	C20—H20B	0.9600
C6'—C19	1.335 (3)	C20—H20C	0.9600
C6'—C7'	1.521 (3)	C21—H21A	0.9600
C7'—C8'	1.539 (3)	C21—H21B	0.9600
C7'—H7'	0.9800	C21—H21C	0.9600
C8'—C9'	1.558 (3)	C22—H22A	0.9300
C8'—H8'A	0.9700	C22—H22B	0.9300
C8'—H8'B	0.9700	O4—H1O4	0.8200
C9'—C15'	1.508 (3)
C14'—C1'—C15'	110.33 (17)	C15'—C9'—C8'	106.81 (17)
C14'—C1'—C11'	102.75 (18)	C20—C9'—C8'	110.84 (17)
C15'—C1'—C11'	99.19 (16)	C10'—C9'—C8'	105.36 (16)
C14'—C1'—C2'	117.43 (19)	O3—C10'—C11'	124.7 (2)
C15'—C1'—C2'	107.85 (16)	O3—C10'—C9'	126.7 (2)
C11'—C1'—C2'	117.74 (16)	C11'—C10'—C9'	108.57 (16)
C3'—C2'—C18	108.96 (18)	O4—C11'—C10'	112.01 (17)
C3'—C2'—C7'	108.52 (16)	O4—C11'—C1'	113.78 (18)
C18—C2'—C7'	110.90 (17)	C10'—C11'—C1'	104.48 (16)
C3'—C2'—C1'	112.18 (17)	O4—C11'—C12'	109.90 (18)
C18—C2'—C1'	110.82 (17)	C10'—C11'—C12'	113.54 (18)
C7'—C2'—C1'	105.40 (16)	C1'—C11'—C12'	102.76 (17)
O1—C2—C17	104.74 (19)	O5—C12'—C21	110.3 (2)
O1—C2—C16	105.43 (18)	O5—C12'—C11'	104.53 (18)
C17—C2—C16	107.8 (2)	C21—C12'—C11'	119.3 (2)
O1—C2—C5'	108.99 (16)	O5—C12'—H12'	107.4
C17—C2—C5'	115.45 (19)	C21—C12'—H12'	107.4
C16—C2—C5'	113.58 (19)	C11'—C12'—H12'	107.4
C2'—C3'—C4'	112.83 (18)	O6—C14'—O5	121.3 (2)
C2'—C3'—H3'A	109.0	O6—C14'—C1'	129.2 (2)
C4'—C3'—H3'A	109.0	O5—C14'—C1'	109.5 (2)
C2'—C3'—H3'B	109.0	C22—C15'—C9'	127.9 (2)
C4'—C3'—H3'B	109.0	C22—C15'—C1'	127.3 (2)
H3'A—C3'—H3'B	107.8	C9'—C15'—C1'	104.78 (16)
C3'—C4'—C5'	114.33 (18)	C2—C16—H16A	109.5
C3'—C4'—H4'A	108.7	C2—C16—H16B	109.5
C5'—C4'—H4'A	108.7	H16A—C16—H16B	109.5
C3'—C4'—H4'B	108.7	C2—C16—H16C	109.5
C5'—C4'—H4'B	108.7	H16A—C16—H16C	109.5
H4'A—C4'—H4'B	107.6	H16B—C16—H16C	109.5
C5—C4—C5'	121.8 (2)	C2—C17—H17A	109.5
C5—C4—H4	119.1	C2—C17—H17B	109.5
C5'—C4—H4	119.1	H17A—C17—H17B	109.5
C4—C5—C6	121.0 (2)	C2—C17—H17C	109.5
C4—C5—H5	119.5	H17A—C17—H17C	109.5
C6—C5—H5	119.5	H17B—C17—H17C	109.5
C4—C5'—C6'	105.89 (16)	C2'—C18—H18A	109.5
C4—C5'—C4'	110.80 (19)	C2'—C18—H18B	109.5
C6'—C5'—C4'	109.60 (16)	H18A—C18—H18B	109.5
C4—C5'—C2	106.50 (17)	C2'—C18—H18C	109.5
C6'—C5'—C2	115.38 (18)	H18A—C18—H18C	109.5
C4'—C5'—C2	108.59 (17)	H18B—C18—H18C	109.5
O2—C6—O1	118.8 (2)	C6'—C19—H19A	120.0
O2—C6—C5	122.7 (2)	C6'—C19—H19B	120.0
O1—C6—C5	118.5 (2)	H19A—C19—H19B	120.0
C19—C6'—C7'	121.66 (19)	C9'—C20—H20A	109.5
C19—C6'—C5'	125.1 (2)	C9'—C20—H20B	109.5
C7'—C6'—C5'	112.97 (16)	H20A—C20—H20B	109.5
C6'—C7'—C8'	114.45 (16)	C9'—C20—H20C	109.5
C6'—C7'—C2'	112.31 (16)	H20A—C20—H20C	109.5
C8'—C7'—C2'	111.99 (15)	H20B—C20—H20C	109.5
C6'—C7'—H7'	105.8	C12'—C21—H21A	109.5
C8'—C7'—H7'	105.8	C12'—C21—H21B	109.5
C2'—C7'—H7'	105.8	H21A—C21—H21B	109.5
C7'—C8'—C9'	113.20 (16)	C12'—C21—H21C	109.5
C7'—C8'—H8'A	108.9	H21A—C21—H21C	109.5
C9'—C8'—H8'A	108.9	H21B—C21—H21C	109.5
C7'—C8'—H8'B	108.9	C15'—C22—H22A	120.0
C9'—C8'—H8'B	108.9	C15'—C22—H22B	120.0
H8'A—C8'—H8'B	107.8	H22A—C22—H22B	120.0
C15'—C9'—C20	117.60 (18)	C6—O1—C2	118.14 (18)
C15'—C9'—C10'	100.50 (17)	C11'—O4—H1O4	109.5
C20—C9'—C10'	114.55 (18)	C14'—O5—C12'	112.37 (17)
C14'—C1'—C2'—C3'	−50.6 (2)	C20—C9'—C10'—O3	−36.0 (3)
C15'—C1'—C2'—C3'	−175.97 (16)	C8'—C9'—C10'—O3	86.1 (3)
C11'—C1'—C2'—C3'	73.0 (2)	C15'—C9'—C10'—C11'	20.4 (2)
C14'—C1'—C2'—C18	71.4 (2)	C20—C9'—C10'—C11'	147.45 (18)
C15'—C1'—C2'—C18	−53.9 (2)	C8'—C9'—C10'—C11'	−90.46 (18)
C11'—C1'—C2'—C18	−164.97 (19)	O3—C10'—C11'—O4	−44.7 (3)
C14'—C1'—C2'—C7'	−168.55 (17)	C9'—C10'—C11'—O4	131.88 (18)
C15'—C1'—C2'—C7'	66.12 (19)	O3—C10'—C11'—C1'	−168.3 (2)
C11'—C1'—C2'—C7'	−44.9 (2)	C9'—C10'—C11'—C1'	8.3 (2)
C18—C2'—C3'—C4'	66.8 (2)	O3—C10'—C11'—C12'	80.5 (3)
C7'—C2'—C3'—C4'	−54.1 (2)	C9'—C10'—C11'—C12'	−102.9 (2)
C1'—C2'—C3'—C4'	−170.11 (17)	C14'—C1'—C11'—O4	91.2 (2)
C2'—C3'—C4'—C5'	53.4 (3)	C15'—C1'—C11'—O4	−155.36 (17)
C5'—C4—C5—C6	3.3 (4)	C2'—C1'—C11'—O4	−39.5 (3)
C5—C4—C5'—C6'	−94.1 (3)	C14'—C1'—C11'—C10'	−146.31 (17)
C5—C4—C5'—C4'	147.1 (2)	C15'—C1'—C11'—C10'	−32.90 (19)
C5—C4—C5'—C2	29.2 (3)	C2'—C1'—C11'—C10'	83.0 (2)
C3'—C4'—C5'—C4	66.5 (2)	C14'—C1'—C11'—C12'	−27.5 (2)
C3'—C4'—C5'—C6'	−50.0 (3)	C15'—C1'—C11'—C12'	85.88 (19)
C3'—C4'—C5'—C2	−176.87 (19)	C2'—C1'—C11'—C12'	−158.27 (17)
O1—C2—C5'—C4	−53.3 (2)	O4—C11'—C12'—O5	−96.7 (2)
C17—C2—C5'—C4	−170.8 (2)	C10'—C11'—C12'—O5	137.02 (18)
C16—C2—C5'—C4	63.9 (2)	C1'—C11'—C12'—O5	24.8 (2)
O1—C2—C5'—C6'	63.9 (2)	O4—C11'—C12'—C21	139.5 (2)
C17—C2—C5'—C6'	−53.6 (3)	C10'—C11'—C12'—C21	13.2 (3)
C16—C2—C5'—C6'	−178.92 (18)	C1'—C11'—C12'—C21	−99.0 (2)
O1—C2—C5'—C4'	−172.67 (17)	C15'—C1'—C14'—O6	94.9 (3)
C17—C2—C5'—C4'	69.8 (3)	C11'—C1'—C14'—O6	−160.1 (3)
C16—C2—C5'—C4'	−55.5 (2)	C2'—C1'—C14'—O6	−29.2 (4)
C4—C5—C6—O2	168.2 (2)	C15'—C1'—C14'—O5	−83.3 (2)
C4—C5—C6—O1	−11.2 (3)	C11'—C1'—C14'—O5	21.7 (2)
C4—C5'—C6'—C19	106.6 (2)	C2'—C1'—C14'—O5	152.63 (18)
C4'—C5'—C6'—C19	−133.8 (2)	C20—C9'—C15'—C22	11.9 (4)
C2—C5'—C6'—C19	−10.9 (3)	C10'—C9'—C15'—C22	136.9 (3)
C4—C5'—C6'—C7'	−67.6 (2)	C8'—C9'—C15'—C22	−113.4 (3)
C4'—C5'—C6'—C7'	51.9 (2)	C20—C9'—C15'—C1'	−167.42 (19)
C2—C5'—C6'—C7'	174.84 (16)	C10'—C9'—C15'—C1'	−42.4 (2)
C19—C6'—C7'—C8'	−0.8 (3)	C8'—C9'—C15'—C1'	67.3 (2)
C5'—C6'—C7'—C8'	173.68 (16)	C14'—C1'—C15'—C22	−24.3 (3)
C19—C6'—C7'—C2'	128.4 (2)	C11'—C1'—C15'—C22	−131.7 (3)
C5'—C6'—C7'—C2'	−57.2 (2)	C2'—C1'—C15'—C22	105.1 (3)
C3'—C2'—C7'—C6'	56.4 (2)	C14'—C1'—C15'—C9'	154.94 (19)
C18—C2'—C7'—C6'	−63.2 (2)	C11'—C1'—C15'—C9'	47.58 (19)
C1'—C2'—C7'—C6'	176.80 (16)	C2'—C1'—C15'—C9'	−75.61 (19)
C3'—C2'—C7'—C8'	−173.15 (17)	O2—C6—O1—C2	162.3 (2)
C18—C2'—C7'—C8'	67.2 (2)	C5—C6—O1—C2	−18.3 (3)
C1'—C2'—C7'—C8'	−52.8 (2)	C17—C2—O1—C6	175.49 (19)
C6'—C7'—C8'—C9'	179.61 (16)	C16—C2—O1—C6	−70.9 (2)
C2'—C7'—C8'—C9'	50.3 (2)	C5'—C2—O1—C6	51.4 (2)
C7'—C8'—C9'—C15'	−56.7 (2)	O6—C14'—O5—C12'	175.7 (2)
C7'—C8'—C9'—C20	174.05 (17)	C1'—C14'—O5—C12'	−6.0 (3)
C7'—C8'—C9'—C10'	49.6 (2)	C21—C12'—O5—C14'	117.0 (2)
C15'—C9'—C10'—O3	−163.1 (2)	C11'—C12'—O5—C14'	−12.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H1O4···O2i	0.82	2.06	2.852 (3)	162
C5—H5···O3ii	0.93	2.63	3.386 (3)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H1O4⋯O2i	0.82	2.06	2.852 (3)	162
C5—H5⋯O3ii	0.93	2.63	3.386 (3)	139

Symmetry codes: (i) ; (ii) .