8-[(3,3-Dimethyl-oxiran-2-yl)methoxy-meth-yl]-11-hydr-oxy-2-isopropenyl-5-methyl-12-oxo-1,2,3,12-tetra-hydro-pyrano[3,2-a]xanthen-1-yl acetate.

The title compound, commonly known as 14-methoxy-tajixanthone-25-acetate, C(28)H(30)O(8), was isolated from Emericella variecolor. The central xanthone core is approximately planar (r.m.s. deviation = 0.084 Å). The dihydro-pyran ring adopts a distorted half-chair conformation. The oxirane plane is oriented at an angle of 63.3 (2)° with respect to the phenol group. An intra-molecular O-H⋯O hydrogen bond forms an S(6) ring. In the crystal, mol-ecules are linked into a two-dimensional network parallel to the ab plane by weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

For general background to 14-methoxy­tajixanthone-25-acetate, see: Bringmann et al. (2003 ▶); Pornpakakul et al. (2006 ▶); Raper & Fennel (1965 ▶). For related structures, see: Fukuyama et al. (1978 ▶); Lee et al. (2005 ▶).

Experimental

Crystal data

C28H30O8

M = 494.54

Monoclinic,

a = 11.3323 (1) Å

b = 8.8199 (2) Å

c = 12.8741 (3) Å

β = 91.765 (1)°

V = 1286.15 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.40 × 0.24 × 0.18 mm

Data collection

Bruker SMART area-detector diffractometer

Absorption correction: none

9335 measured reflections

3840 independent reflections

2691 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.141

S = 1.06

3840 reflections

335 parameters

16 restraints

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 2006 ▶); cell refinement: SAINT-Plus (Bruker, 2006 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809038343/ci2902sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038343/ci2902Isup2.hkl

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

C28H30O8	F(000) = 524
Mr = 494.54	Dx = 1.277 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 9335 reflections
a = 11.3323 (1) Å	θ = 1.6–30.4°
b = 8.8199 (2) Å	µ = 0.09 mm−1
c = 12.8741 (3) Å	T = 293 K
β = 91.765 (1)°	Plate, yellow
V = 1286.15 (4) Å3	0.40 × 0.24 × 0.18 mm
Z = 2

Bruker SMART area-detector diffractometer	2691 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
graphite	θmax = 30.4°, θmin = 1.6°
ω scans	h = −16→15
9335 measured reflections	k = −9→12
3840 independent reflections	l = −18→17

Refinement on F2	16 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.056	w = 1/[σ2(Fo2) + (0.0608P)2 + 0.2544P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.141	(Δ/σ)max = 0.001
S = 1.06	Δρmax = 0.20 e Å−3
3840 reflections	Δρmin = −0.27 e Å−3
335 parameters

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	1.17752 (18)	0.0959 (3)	0.89869 (16)	0.0466 (6)
O2	0.77214 (19)	0.4077 (3)	0.79097 (15)	0.0415 (5)
O3	0.8611 (2)	0.0712 (3)	0.58879 (16)	0.0455 (5)
O4	0.7032 (2)	0.1668 (3)	0.45891 (18)	0.0542 (7)
H4	0.7573	0.1133	0.4816	0.081*
O5	0.6074 (4)	0.7709 (4)	0.6946 (3)	0.0937 (12)
O6	1.0238 (2)	−0.1231 (3)	0.70433 (16)	0.0444 (5)
O7	1.0451 (2)	−0.1637 (3)	0.53268 (18)	0.0592 (7)
O8	0.4404 (3)	0.7222 (4)	0.8668 (3)	0.0780 (9)
C1	1.0770 (3)	0.0262 (4)	0.6941 (2)	0.0365 (6)
H1	1.0648	0.0638	0.6230	0.044*
C2	1.2093 (3)	0.0120 (4)	0.7207 (2)	0.0435 (7)
H2	1.2384	−0.0757	0.6823	0.052*
C3	1.2211 (3)	−0.0264 (5)	0.8359 (2)	0.0483 (8)
H3A	1.1768	−0.1180	0.8496	0.058*
H3B	1.3033	−0.0454	0.8544	0.058*
C4	1.0734 (3)	0.1616 (4)	0.8659 (2)	0.0380 (7)
C5	1.0267 (3)	0.2659 (4)	0.9370 (2)	0.0412 (7)
C6	0.9258 (3)	0.3443 (4)	0.9087 (2)	0.0420 (7)
H6	0.8946	0.4148	0.9540	0.050*
C6A	0.8702 (3)	0.3185 (4)	0.8119 (2)	0.0374 (6)
C7	1.0181 (2)	0.1313 (4)	0.7703 (2)	0.0336 (6)
C7A	0.9106 (3)	0.2103 (4)	0.7430 (2)	0.0341 (6)
C8	0.6238 (3)	0.5019 (4)	0.6755 (2)	0.0415 (7)
C8A	0.7130 (3)	0.3972 (4)	0.6967 (2)	0.0374 (7)
C9	0.5634 (3)	0.4873 (5)	0.5797 (3)	0.0490 (8)
H9	0.5037	0.5563	0.5632	0.059*
C10	0.5881 (3)	0.3753 (5)	0.5083 (3)	0.0502 (9)
H10	0.5442	0.3683	0.4463	0.060*
C11	0.6781 (3)	0.2743 (4)	0.5299 (2)	0.0424 (7)
C11A	0.7432 (3)	0.2835 (4)	0.6255 (2)	0.0370 (6)
C12	0.8409 (3)	0.1797 (4)	0.6476 (2)	0.0364 (7)
C13	0.5943 (3)	0.6298 (4)	0.7483 (3)	0.0468 (8)
H13	0.6479	0.6272	0.8094	0.056*
C14	0.4695 (3)	0.6246 (5)	0.7819 (3)	0.0576 (10)
H14	0.4104	0.6229	0.7246	0.069*
C15	0.4291 (5)	0.5607 (6)	0.8791 (4)	0.0771 (13)
C16	0.3022 (6)	0.5108 (11)	0.8848 (6)	0.133 (3)
H16A	0.2725	0.5372	0.9515	0.200*
H16B	0.2974	0.4030	0.8754	0.200*
H16C	0.2558	0.5604	0.8312	0.200*
C17	0.5144 (7)	0.4907 (11)	0.9560 (5)	0.132 (3)
H17A	0.4787	0.4841	1.0225	0.197*
H17B	0.5843	0.5521	0.9618	0.197*
H17C	0.5351	0.3909	0.9330	0.197*
C18	0.6673 (8)	0.8824 (9)	0.7449 (9)	0.098 (4)	0.694 (16)
H18A	0.6714	0.9699	0.7007	0.147*	0.694 (16)
H18B	0.7458	0.8481	0.7626	0.147*	0.694 (16)
H18C	0.6275	0.9087	0.8071	0.147*	0.694 (16)
C18'	0.7012 (12)	0.841 (2)	0.6681 (17)	0.082 (6)	0.306 (16)
H18D	0.7277	0.8013	0.6036	0.123*	0.306 (16)
H18E	0.7619	0.8284	0.7211	0.123*	0.306 (16)
H18F	0.6840	0.9475	0.6600	0.123*	0.306 (16)
C19	1.0135 (3)	−0.2066 (4)	0.6160 (3)	0.0502 (8)
C20	0.9601 (6)	−0.3577 (6)	0.6382 (4)	0.1004 (19)
H20A	0.9764	−0.3843	0.7095	0.151*
H20B	0.9934	−0.4329	0.5938	0.151*
H20C	0.8763	−0.3531	0.6255	0.151*
C21	1.2826 (3)	0.1480 (5)	0.6893 (3)	0.0517 (9)
C22	1.2410 (4)	0.2625 (6)	0.6336 (4)	0.0888 (16)
H22A	1.2908	0.3415	0.6157	0.107*
H22B	1.1619	0.2644	0.6122	0.107*
C23	1.4093 (4)	0.1446 (8)	0.7237 (4)	0.0872 (15)
H23A	1.4408	0.0450	0.7128	0.131*
H23B	1.4161	0.1695	0.7963	0.131*
H23C	1.4526	0.2171	0.6844	0.131*
C24	1.0876 (3)	0.2921 (5)	1.0420 (2)	0.0574 (10)
H24A	1.1662	0.3290	1.0322	0.086*
H24B	1.0913	0.1984	1.0799	0.086*
H24C	1.0440	0.3655	1.0803	0.086*

	U11	U22	U33	U12	U13	U23
O1	0.0437 (12)	0.0556 (15)	0.0402 (11)	0.0145 (11)	−0.0051 (9)	−0.0011 (10)
O2	0.0442 (12)	0.0433 (13)	0.0365 (10)	0.0112 (10)	−0.0044 (9)	−0.0029 (9)
O3	0.0512 (12)	0.0423 (13)	0.0429 (11)	0.0013 (11)	−0.0031 (9)	−0.0102 (10)
O4	0.0515 (13)	0.0636 (17)	0.0469 (12)	−0.0014 (13)	−0.0099 (10)	−0.0169 (12)
O5	0.163 (4)	0.0434 (17)	0.0730 (19)	−0.019 (2)	−0.031 (2)	0.0128 (15)
O6	0.0558 (13)	0.0356 (12)	0.0424 (11)	−0.0041 (11)	0.0086 (9)	−0.0017 (10)
O7	0.0778 (17)	0.0538 (16)	0.0467 (13)	0.0035 (15)	0.0126 (12)	−0.0099 (12)
O8	0.081 (2)	0.0619 (19)	0.091 (2)	0.0141 (17)	0.0095 (17)	−0.0240 (17)
C1	0.0421 (16)	0.0315 (15)	0.0361 (14)	−0.0008 (13)	0.0043 (12)	−0.0003 (12)
C2	0.0423 (16)	0.0416 (18)	0.0471 (16)	0.0062 (15)	0.0071 (13)	−0.0046 (14)
C3	0.0473 (18)	0.051 (2)	0.0468 (17)	0.0155 (17)	0.0012 (14)	0.0001 (16)
C4	0.0396 (15)	0.0394 (17)	0.0348 (14)	0.0059 (14)	−0.0006 (11)	0.0017 (13)
C5	0.0469 (17)	0.0446 (18)	0.0318 (14)	0.0031 (15)	−0.0032 (12)	0.0016 (13)
C6	0.0477 (17)	0.0451 (18)	0.0331 (14)	0.0090 (15)	−0.0003 (12)	−0.0062 (13)
C6A	0.0373 (15)	0.0379 (16)	0.0370 (14)	0.0037 (13)	0.0001 (11)	0.0001 (13)
C7	0.0357 (14)	0.0329 (15)	0.0322 (13)	−0.0003 (13)	0.0020 (11)	0.0001 (12)
C7A	0.0363 (14)	0.0353 (15)	0.0306 (13)	−0.0024 (13)	0.0019 (11)	−0.0001 (11)
C8	0.0411 (16)	0.0392 (18)	0.0439 (16)	−0.0010 (15)	−0.0031 (13)	0.0029 (14)
C8A	0.0343 (15)	0.0400 (16)	0.0378 (15)	−0.0039 (14)	−0.0007 (12)	0.0030 (13)
C9	0.0422 (17)	0.052 (2)	0.0516 (18)	0.0034 (17)	−0.0114 (14)	0.0077 (17)
C10	0.0459 (17)	0.061 (2)	0.0430 (16)	−0.0015 (18)	−0.0148 (13)	−0.0003 (16)
C11	0.0354 (15)	0.052 (2)	0.0400 (15)	−0.0087 (15)	−0.0015 (12)	−0.0021 (15)
C11A	0.0337 (14)	0.0429 (17)	0.0342 (14)	−0.0046 (14)	−0.0007 (11)	0.0027 (13)
C12	0.0361 (14)	0.0367 (17)	0.0363 (14)	−0.0090 (13)	0.0008 (12)	0.0013 (13)
C13	0.0542 (19)	0.0408 (18)	0.0447 (17)	0.0050 (16)	−0.0106 (14)	0.0046 (15)
C14	0.057 (2)	0.056 (2)	0.060 (2)	0.0177 (19)	−0.0058 (16)	−0.0091 (18)
C15	0.085 (3)	0.069 (3)	0.079 (3)	−0.004 (3)	0.024 (2)	−0.012 (2)
C16	0.117 (4)	0.136 (6)	0.151 (5)	−0.031 (4)	0.065 (4)	−0.048 (5)
C17	0.169 (6)	0.134 (6)	0.093 (4)	0.025 (5)	0.026 (4)	0.042 (4)
C18	0.087 (6)	0.063 (5)	0.144 (9)	−0.021 (4)	−0.005 (6)	0.013 (5)
C18'	0.095 (11)	0.060 (9)	0.093 (13)	0.026 (8)	0.020 (9)	−0.002 (9)
C19	0.058 (2)	0.0392 (19)	0.0541 (19)	−0.0021 (17)	0.0097 (16)	−0.0102 (16)
C20	0.152 (5)	0.057 (3)	0.094 (3)	−0.043 (3)	0.033 (3)	−0.022 (3)
C21	0.0450 (18)	0.057 (2)	0.0532 (19)	−0.0070 (18)	0.0084 (14)	−0.0058 (18)
C22	0.073 (3)	0.074 (3)	0.119 (4)	−0.026 (3)	−0.003 (3)	0.035 (3)
C23	0.060 (2)	0.109 (4)	0.093 (3)	−0.022 (3)	−0.001 (2)	0.000 (3)
C24	0.064 (2)	0.070 (3)	0.0380 (16)	0.017 (2)	−0.0119 (15)	−0.0120 (17)

O1—C4	1.370 (4)	C9—H9	0.93
O1—C3	1.444 (4)	C10—C11	1.376 (5)
O2—C8A	1.372 (4)	C10—H10	0.93
O2—C6A	1.381 (4)	C11—C11A	1.418 (4)
O3—C12	1.246 (4)	C11A—C12	1.458 (4)
O4—C11	1.353 (4)	C13—C14	1.492 (5)
O4—H4	0.82	C13—H13	0.98
O5—C18'	1.287 (11)	C14—C15	1.459 (6)
O5—C18	1.350 (8)	C14—H14	0.98
O5—C13	1.434 (5)	C15—C17	1.496 (9)
O6—C19	1.357 (4)	C15—C16	1.508 (8)
O6—C1	1.456 (4)	C16—H16A	0.96
O7—C19	1.202 (4)	C16—H16B	0.96
O8—C14	1.438 (5)	C16—H16C	0.96
O8—C15	1.439 (6)	C17—H17A	0.96
C1—C7	1.519 (4)	C17—H17B	0.96
C1—C2	1.533 (4)	C17—H17C	0.96
C1—H1	0.98	C18—H18A	0.96
C2—C21	1.520 (5)	C18—H18B	0.96
C2—C3	1.523 (4)	C18—H18C	0.96
C2—H2	0.98	C18'—H18D	0.96
C3—H3A	0.97	C18'—H18E	0.96
C3—H3B	0.97	C18'—H18F	0.96
C4—C7	1.390 (4)	C19—C20	1.495 (6)
C4—C5	1.412 (4)	C20—H20A	0.96
C5—C6	1.376 (4)	C20—H20B	0.96
C5—C24	1.516 (4)	C20—H20C	0.96
C6—C6A	1.398 (4)	C21—C22	1.318 (6)
C6—H6	0.93	C21—C23	1.490 (5)
C6A—C7A	1.389 (4)	C22—H22A	0.93
C7—C7A	1.437 (4)	C22—H22B	0.93
C7A—C12	1.465 (4)	C23—H23A	0.96
C8—C8A	1.390 (5)	C23—H23B	0.96
C8—C9	1.397 (4)	C23—H23C	0.96
C8—C13	1.511 (5)	C24—H24A	0.96
C8A—C11A	1.408 (4)	C24—H24B	0.96
C9—C10	1.384 (5)	C24—H24C	0.96
C4—O1—C3	116.7 (2)	C14—C13—C8	112.8 (3)
C8A—O2—C6A	120.1 (2)	O5—C13—H13	109.7
C11—O4—H4	109.5	C14—C13—H13	109.7
C18'—O5—C18	50.7 (9)	C8—C13—H13	109.7
C18'—O5—C13	130.2 (9)	O8—C14—C15	59.5 (3)
C18—O5—C13	117.3 (5)	O8—C14—C13	116.3 (3)
C19—O6—C1	116.1 (2)	C15—C14—C13	125.9 (4)
C14—O8—C15	61.0 (3)	O8—C14—H14	114.5
O6—C1—C7	107.6 (2)	C15—C14—H14	114.5
O6—C1—C2	108.1 (3)	C13—C14—H14	114.5
C7—C1—C2	110.6 (2)	O8—C15—C14	59.5 (3)
O6—C1—H1	110.1	O8—C15—C17	115.1 (6)
C7—C1—H1	110.1	C14—C15—C17	120.9 (5)
C2—C1—H1	110.1	O8—C15—C16	112.5 (5)
C21—C2—C3	113.7 (3)	C14—C15—C16	118.6 (5)
C21—C2—C1	114.5 (3)	C17—C15—C16	116.5 (6)
C3—C2—C1	106.9 (2)	C15—C16—H16A	109.5
C21—C2—H2	107.1	C15—C16—H16B	109.5
C3—C2—H2	107.1	H16A—C16—H16B	109.5
C1—C2—H2	107.1	C15—C16—H16C	109.5
O1—C3—C2	111.0 (3)	H16A—C16—H16C	109.5
O1—C3—H3A	109.4	H16B—C16—H16C	109.5
C2—C3—H3A	109.4	C15—C17—H17A	109.5
O1—C3—H3B	109.4	C15—C17—H17B	109.5
C2—C3—H3B	109.4	H17A—C17—H17B	109.5
H3A—C3—H3B	108.0	C15—C17—H17C	109.5
O1—C4—C7	123.5 (3)	H17A—C17—H17C	109.5
O1—C4—C5	114.3 (2)	H17B—C17—H17C	109.5
C7—C4—C5	122.2 (3)	O5—C18—H18A	109.5
C6—C5—C4	118.7 (3)	O5—C18—H18B	109.5
C6—C5—C24	120.8 (3)	H18A—C18—H18B	109.5
C4—C5—C24	120.5 (3)	O5—C18—H18C	109.5
C5—C6—C6A	120.2 (3)	H18A—C18—H18C	109.5
C5—C6—H6	119.9	H18B—C18—H18C	109.5
C6A—C6—H6	119.9	O5—C18'—H18D	109.5
O2—C6A—C7A	123.1 (3)	O5—C18'—H18E	109.5
O2—C6A—C6	114.7 (3)	H18D—C18'—H18E	109.5
C7A—C6A—C6	122.1 (3)	O5—C18'—H18F	109.5
C4—C7—C7A	118.6 (3)	H18D—C18'—H18F	109.5
C4—C7—C1	119.6 (3)	H18E—C18'—H18F	109.5
C7A—C7—C1	121.6 (2)	O7—C19—O6	123.8 (3)
C6A—C7A—C7	118.1 (3)	O7—C19—C20	125.7 (4)
C6A—C7A—C12	118.7 (3)	O6—C19—C20	110.4 (3)
C7—C7A—C12	123.1 (3)	C19—C20—H20A	109.5
C8A—C8—C9	116.4 (3)	C19—C20—H20B	109.5
C8A—C8—C13	123.3 (3)	H20A—C20—H20B	109.5
C9—C8—C13	120.3 (3)	C19—C20—H20C	109.5
O2—C8A—C8	117.5 (3)	H20A—C20—H20C	109.5
O2—C8A—C11A	120.2 (3)	H20B—C20—H20C	109.5
C8—C8A—C11A	122.4 (3)	C22—C21—C23	120.2 (4)
C10—C9—C8	123.3 (3)	C22—C21—C2	124.1 (3)
C10—C9—H9	118.4	C23—C21—C2	115.7 (4)
C8—C9—H9	118.4	C21—C22—H22A	120.0
C11—C10—C9	119.5 (3)	C21—C22—H22B	120.0
C11—C10—H10	120.3	H22A—C22—H22B	120.0
C9—C10—H10	120.3	C21—C23—H23A	109.5
O4—C11—C10	119.2 (3)	C21—C23—H23B	109.5
O4—C11—C11A	120.8 (3)	H23A—C23—H23B	109.5
C10—C11—C11A	120.0 (3)	C21—C23—H23C	109.5
C8A—C11A—C11	118.4 (3)	H23A—C23—H23C	109.5
C8A—C11A—C12	121.2 (2)	H23B—C23—H23C	109.5
C11—C11A—C12	120.4 (3)	C5—C24—H24A	109.5
O3—C12—C11A	121.1 (3)	C5—C24—H24B	109.5
O3—C12—C7A	123.1 (3)	H24A—C24—H24B	109.5
C11A—C12—C7A	115.8 (3)	C5—C24—H24C	109.5
O5—C13—C14	106.2 (3)	H24A—C24—H24C	109.5
O5—C13—C8	108.7 (3)	H24B—C24—H24C	109.5
C19—O6—C1—C7	146.2 (3)	C8—C9—C10—C11	−1.7 (6)
C19—O6—C1—C2	−94.3 (3)	C9—C10—C11—O4	−178.8 (3)
O6—C1—C2—C21	166.1 (3)	C9—C10—C11—C11A	1.3 (5)
C7—C1—C2—C21	−76.3 (3)	O2—C8A—C11A—C11	178.6 (3)
O6—C1—C2—C3	−67.0 (3)	C8—C8A—C11A—C11	−1.5 (4)
C7—C1—C2—C3	50.6 (3)	O2—C8A—C11A—C12	−3.0 (4)
C4—O1—C3—C2	43.6 (4)	C8—C8A—C11A—C12	177.0 (3)
C21—C2—C3—O1	63.2 (4)	O4—C11—C11A—C8A	−179.7 (3)
C1—C2—C3—O1	−64.2 (4)	C10—C11—C11A—C8A	0.2 (5)
C3—O1—C4—C7	−9.1 (4)	O4—C11—C11A—C12	1.8 (4)
C3—O1—C4—C5	171.8 (3)	C10—C11—C11A—C12	−178.3 (3)
O1—C4—C5—C6	176.3 (3)	C8A—C11A—C12—O3	173.7 (3)
C7—C4—C5—C6	−2.8 (5)	C11—C11A—C12—O3	−7.9 (4)
O1—C4—C5—C24	−2.9 (5)	C8A—C11A—C12—C7A	−5.3 (4)
C7—C4—C5—C24	178.0 (3)	C11—C11A—C12—C7A	173.2 (3)
C4—C5—C6—C6A	1.1 (5)	C6A—C7A—C12—O3	−169.7 (3)
C24—C5—C6—C6A	−179.7 (3)	C7—C7A—C12—O3	8.9 (5)
C8A—O2—C6A—C7A	−3.2 (4)	C6A—C7A—C12—C11A	9.2 (4)
C8A—O2—C6A—C6	177.3 (3)	C7—C7A—C12—C11A	−172.2 (3)
C5—C6—C6A—O2	−177.9 (3)	C18'—O5—C13—C14	165.3 (14)
C5—C6—C6A—C7A	2.6 (5)	C18—O5—C13—C14	105.2 (7)
O1—C4—C7—C7A	−178.3 (3)	C18'—O5—C13—C8	−73.1 (14)
C5—C4—C7—C7A	0.7 (5)	C18—O5—C13—C8	−133.2 (6)
O1—C4—C7—C1	−3.2 (5)	C8A—C8—C13—O5	121.2 (4)
C5—C4—C7—C1	175.8 (3)	C9—C8—C13—O5	−56.5 (4)
O6—C1—C7—C4	98.4 (3)	C8A—C8—C13—C14	−121.2 (3)
C2—C1—C7—C4	−19.5 (4)	C9—C8—C13—C14	61.1 (4)
O6—C1—C7—C7A	−86.6 (3)	C15—O8—C14—C13	−117.9 (4)
C2—C1—C7—C7A	155.5 (3)	O5—C13—C14—O8	−73.3 (4)
O2—C6A—C7A—C7	175.9 (3)	C8—C13—C14—O8	167.7 (3)
C6—C6A—C7A—C7	−4.6 (4)	O5—C13—C14—C15	−143.4 (4)
O2—C6A—C7A—C12	−5.4 (4)	C8—C13—C14—C15	97.6 (5)
C6—C6A—C7A—C12	174.1 (3)	C14—O8—C15—C17	112.5 (5)
C4—C7—C7A—C6A	2.9 (4)	C14—O8—C15—C16	−111.0 (5)
C1—C7—C7A—C6A	−172.1 (3)	C13—C14—C15—O8	102.1 (5)
C4—C7—C7A—C12	−175.7 (3)	O8—C14—C15—C17	−102.7 (6)
C1—C7—C7A—C12	9.3 (4)	C13—C14—C15—C17	−0.6 (8)
C6A—O2—C8A—C8	−172.6 (3)	O8—C14—C15—C16	100.6 (6)
C6A—O2—C8A—C11A	7.4 (4)	C13—C14—C15—C16	−157.3 (5)
C9—C8—C8A—O2	−178.9 (3)	C1—O6—C19—O7	−0.2 (5)
C13—C8—C8A—O2	3.3 (5)	C1—O6—C19—C20	178.8 (4)
C9—C8—C8A—C11A	1.1 (5)	C3—C2—C21—C22	−130.7 (4)
C13—C8—C8A—C11A	−176.6 (3)	C1—C2—C21—C22	−7.3 (6)
C8A—C8—C9—C10	0.4 (5)	C3—C2—C21—C23	50.6 (4)
C13—C8—C9—C10	178.3 (3)	C1—C2—C21—C23	173.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3	0.82	1.82	2.554 (3)	148
C3—H3B···O8i	0.97	2.57	3.345 (5)	137
C9—H9···O4ii	0.93	2.55	3.434 (4)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O3	0.82	1.82	2.554 (3)	148
C3—H3B⋯O8i	0.97	2.57	3.345 (5)	137
C9—H9⋯O4ii	0.93	2.55	3.434 (4)	160

Symmetry codes: (i) ; (ii) .