(2R,3S)-2-Benzyl-3-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranos-yloxy)butanolide.

The title compound, C(25)H(30)O(12), which demonstrates a significant hepatoprotective effect, has comparable geometrical parameters to those of similar compounds. The absolute configuration of the title compound, viz. 2R,3S, was identified from the Flack parameter of 0.05 (17) and the Hooft parameter of 0.04 (6).

Related literature

For the hepatoprotective effect of the title compound, see: Du & Irinon (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the Hooft parameter, see: Hooft et al.(2008 ▶). For details of the preparation, see: Saito et al. (1992 ▶); Kazumasa et al. (2000 ▶); Schmidt (1986 ▶); Corey & Venkateswarlu (1972 ▶); Fernandez et al. (1997 ▶).

Experimental

Crystal data

C25H30O12

M = 522.49

Orthorhombic,

a = 10.6142 (2) Å

b = 11.0984 (2) Å

c = 22.9714 (3) Å

V = 2706.05 (8) Å3

Z = 4

Cu Kα radiation

μ = 0.87 mm−1

T = 153 K

0.15 × 0.15 × 0.10 mm

Data collection

Mac dip 2030b diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.880, T max = 0.918

7246 measured reflections

4102 independent reflections

4015 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.102

S = 1.07

4102 reflections

334 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.22 e Å−3

Absolute structure: Flack (1983 ▶), 1417 Friedel pairs

Flack parameter: 0.05 (17)

Data collection: DENZO (Otwinowski & Minor, 1997 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810006628/vm2019sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810006628/vm2019Isup2.hkl

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

C25H30O12	F(000) = 1104
Mr = 522.49	Dx = 1.282 Mg m−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5304 reflections
a = 10.6142 (2) Å	θ = 4.0–65.7°
b = 11.0984 (2) Å	µ = 0.87 mm−1
c = 22.9714 (3) Å	T = 153 K
V = 2706.05 (8) Å3	Block, white
Z = 4	0.15 × 0.15 × 0.10 mm

Mac dip 2030b diffractometer	4102 independent reflections
Radiation source: rotating anode	4015 reflections with I > 2σ(I)
graphite	Rint = 0.016
Detector resolution: 0 pixels mm-1	θmax = 66.0°, θmin = 4.4°
ω scans	h = −12→9
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −12→12
Tmin = 0.880, Tmax = 0.918	l = −26→26
7246 measured reflections

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)] = 0.036	H-atom parameters constrained
wR(F2) = 0.102	w = 1/[σ2(Fo2) + (0.0654P)2 + 0.5803P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
4102 reflections	Δρmax = 0.34 e Å−3
334 parameters	Δρmin = −0.22 e Å−3
0 restraints	Absolute structure: Flack (1983), 1417 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.05 (17)

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.

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	0.47650 (16)	0.31851 (14)	0.32119 (7)	0.0442 (4)
O2	0.58032 (14)	0.48590 (14)	0.29725 (6)	0.0403 (3)
O3	0.49559 (12)	0.47669 (12)	0.17568 (6)	0.0311 (3)
O4	0.44988 (12)	0.58270 (12)	0.09414 (6)	0.0300 (3)
O5	0.73101 (12)	0.40529 (12)	0.12561 (6)	0.0319 (3)
O6	0.71425 (13)	0.39829 (13)	0.00188 (6)	0.0351 (3)
O7	0.61363 (13)	0.62268 (12)	−0.04400 (6)	0.0325 (3)
O8	0.29897 (12)	0.61966 (13)	−0.00230 (6)	0.0353 (3)
O9	0.64011 (15)	0.22826 (13)	0.14807 (7)	0.0427 (4)
O10	0.89389 (19)	0.49770 (18)	−0.01722 (12)	0.0784 (7)
O11	0.5236 (2)	0.4937 (2)	−0.10623 (7)	0.0675 (6)
O12	0.2865 (2)	0.7043 (2)	−0.09013 (8)	0.0739 (7)
C1	0.4778 (2)	0.41371 (19)	0.29662 (9)	0.0341 (4)
C2	0.37455 (19)	0.47400 (18)	0.26180 (8)	0.0306 (4)
H2A	0.3281	0.5283	0.2891	0.037*
C3	0.45018 (18)	0.55428 (17)	0.22133 (8)	0.0297 (4)
H3A	0.4010	0.6247	0.2064	0.036*
C4	0.5581 (2)	0.59050 (19)	0.26080 (9)	0.0351 (4)
H4A	0.6341	0.6103	0.2377	0.042*
H4B	0.5350	0.6613	0.2847	0.042*
C5	0.2771 (2)	0.38840 (18)	0.23518 (9)	0.0346 (4)
H5A	0.3174	0.3409	0.2038	0.042*
H5B	0.2477	0.3314	0.2654	0.042*
C6	0.16563 (19)	0.45524 (18)	0.21066 (10)	0.0354 (4)
C7	0.0715 (2)	0.4974 (2)	0.24720 (10)	0.0421 (5)
H7A	0.0756	0.4808	0.2877	0.050*
C8	−0.0285 (2)	0.5636 (2)	0.22519 (15)	0.0569 (7)
H8A	−0.0916	0.5928	0.2509	0.068*
C9	−0.0377 (3)	0.5875 (2)	0.16642 (15)	0.0616 (8)
H9A	−0.1064	0.6328	0.1515	0.074*
C10	0.0552 (3)	0.5443 (3)	0.12938 (13)	0.0606 (8)
H10A	0.0493	0.5591	0.0887	0.073*
C11	0.1569 (2)	0.4795 (2)	0.15118 (10)	0.0456 (5)
H11A	0.2207	0.4516	0.1255	0.055*
C1'	0.54911 (18)	0.53583 (18)	0.12866 (8)	0.0294 (4)
H1'A	0.6062	0.6018	0.1421	0.035*
C2'	0.62123 (18)	0.44333 (18)	0.09365 (8)	0.0283 (4)
H2'A	0.5661	0.3723	0.0854	0.034*
C3'	0.66843 (17)	0.49655 (17)	0.03700 (8)	0.0281 (4)
H3'A	0.7380	0.5551	0.0448	0.034*
C4'	0.56170 (18)	0.55880 (17)	0.00501 (8)	0.0288 (4)
H4'A	0.4997	0.4974	−0.0089	0.035*
C5'	0.49602 (18)	0.64833 (18)	0.04534 (8)	0.0299 (4)
H5'A	0.5582	0.7100	0.0589	0.036*
C6'	0.38565 (19)	0.71066 (19)	0.01696 (9)	0.0359 (5)
H6'A	0.3439	0.7650	0.0452	0.043*
H6'B	0.4148	0.7593	−0.0166	0.043*
C7'	0.7291 (2)	0.29459 (19)	0.15016 (9)	0.0351 (4)
C8'	0.8527 (3)	0.2666 (2)	0.17810 (13)	0.0547 (6)
H8'A	0.8493	0.1860	0.1955	0.082*
H8'B	0.8703	0.3262	0.2085	0.082*
H8'C	0.9195	0.2692	0.1487	0.082*
C9'	0.8281 (2)	0.4122 (2)	−0.02386 (12)	0.0516 (6)
C10'	0.8550 (4)	0.3043 (3)	−0.06145 (19)	0.0899 (12)
H10B	0.9370	0.3143	−0.0804	0.135*
H10C	0.7892	0.2967	−0.0912	0.135*
H10D	0.8562	0.2315	−0.0373	0.135*
C11'	0.5904 (2)	0.5778 (2)	−0.09765 (9)	0.0385 (5)
C12'	0.6610 (2)	0.6479 (2)	−0.14304 (10)	0.0464 (5)
H12A	0.6431	0.6142	−0.1816	0.070*
H12B	0.7516	0.6428	−0.1353	0.070*
H12C	0.6343	0.7324	−0.1419	0.070*
C13'	0.26186 (19)	0.6221 (2)	−0.05781 (9)	0.0403 (5)
C14'	0.1842 (2)	0.5152 (3)	−0.07186 (11)	0.0526 (6)
H14A	0.1585	0.5186	−0.1128	0.079*
H14B	0.1091	0.5144	−0.0470	0.079*
H14C	0.2334	0.4419	−0.0650	0.079*

	U11	U22	U33	U12	U13	U23
O1	0.0555 (9)	0.0361 (8)	0.0410 (8)	0.0107 (7)	−0.0020 (7)	0.0053 (7)
O2	0.0368 (8)	0.0424 (9)	0.0418 (7)	0.0029 (7)	−0.0093 (6)	−0.0006 (7)
O3	0.0359 (7)	0.0277 (7)	0.0297 (6)	−0.0020 (5)	0.0038 (5)	−0.0030 (6)
O4	0.0273 (7)	0.0310 (7)	0.0318 (6)	0.0005 (6)	0.0018 (5)	−0.0016 (6)
O5	0.0276 (7)	0.0281 (7)	0.0401 (7)	−0.0025 (6)	−0.0058 (6)	0.0042 (6)
O6	0.0340 (7)	0.0320 (7)	0.0393 (7)	0.0047 (6)	0.0059 (6)	−0.0049 (6)
O7	0.0321 (7)	0.0342 (7)	0.0313 (6)	−0.0013 (6)	0.0026 (6)	0.0017 (6)
O8	0.0294 (7)	0.0396 (8)	0.0369 (7)	−0.0006 (6)	−0.0016 (6)	0.0059 (6)
O9	0.0455 (9)	0.0308 (8)	0.0518 (8)	−0.0081 (7)	−0.0055 (7)	0.0073 (7)
O10	0.0542 (11)	0.0501 (12)	0.1310 (19)	−0.0041 (10)	0.0518 (12)	−0.0067 (12)
O11	0.0873 (14)	0.0811 (15)	0.0342 (8)	−0.0362 (13)	−0.0059 (8)	−0.0060 (9)
O12	0.0730 (13)	0.0984 (17)	0.0504 (10)	−0.0315 (12)	−0.0147 (9)	0.0310 (11)
C1	0.0384 (11)	0.0333 (11)	0.0305 (9)	0.0050 (9)	0.0005 (8)	−0.0050 (9)
C2	0.0327 (10)	0.0287 (10)	0.0303 (9)	0.0043 (8)	0.0020 (8)	−0.0028 (8)
C3	0.0300 (10)	0.0271 (10)	0.0320 (9)	0.0022 (8)	−0.0005 (8)	−0.0042 (8)
C4	0.0331 (10)	0.0339 (11)	0.0383 (10)	−0.0011 (8)	−0.0029 (8)	−0.0039 (9)
C5	0.0345 (10)	0.0280 (10)	0.0413 (10)	−0.0006 (9)	0.0030 (9)	−0.0007 (9)
C6	0.0317 (10)	0.0280 (10)	0.0464 (11)	−0.0061 (8)	−0.0026 (9)	−0.0024 (9)
C7	0.0312 (10)	0.0416 (12)	0.0534 (12)	−0.0050 (9)	−0.0025 (9)	−0.0091 (11)
C8	0.0311 (12)	0.0459 (14)	0.094 (2)	−0.0005 (10)	−0.0113 (12)	−0.0126 (14)
C9	0.0429 (14)	0.0391 (13)	0.103 (2)	−0.0070 (11)	−0.0301 (15)	0.0106 (15)
C10	0.0598 (17)	0.0572 (16)	0.0650 (16)	−0.0182 (14)	−0.0268 (14)	0.0211 (14)
C11	0.0473 (12)	0.0424 (13)	0.0471 (12)	−0.0111 (11)	−0.0049 (10)	0.0031 (10)
C1'	0.0280 (9)	0.0284 (10)	0.0317 (9)	−0.0053 (8)	−0.0001 (8)	−0.0017 (8)
C2'	0.0234 (9)	0.0271 (10)	0.0342 (9)	−0.0028 (7)	−0.0031 (8)	0.0009 (8)
C3'	0.0251 (9)	0.0255 (9)	0.0337 (9)	−0.0003 (7)	0.0034 (7)	−0.0034 (8)
C4'	0.0273 (9)	0.0280 (10)	0.0310 (9)	−0.0028 (7)	0.0018 (8)	−0.0006 (8)
C5'	0.0277 (10)	0.0282 (10)	0.0338 (9)	−0.0011 (7)	0.0027 (8)	−0.0001 (8)
C6'	0.0309 (10)	0.0329 (11)	0.0439 (11)	0.0045 (9)	0.0021 (9)	0.0018 (9)
C7'	0.0404 (11)	0.0284 (10)	0.0366 (10)	0.0008 (9)	−0.0039 (9)	0.0014 (8)
C8'	0.0558 (15)	0.0383 (13)	0.0701 (15)	−0.0020 (11)	−0.0260 (13)	0.0120 (12)
C9'	0.0476 (13)	0.0386 (13)	0.0686 (15)	0.0099 (11)	0.0254 (12)	0.0046 (12)
C10'	0.087 (2)	0.0606 (18)	0.122 (3)	0.0138 (17)	0.060 (2)	−0.014 (2)
C11'	0.0371 (12)	0.0449 (13)	0.0335 (10)	0.0044 (10)	−0.0032 (9)	−0.0009 (9)
C12'	0.0471 (13)	0.0555 (14)	0.0365 (10)	0.0082 (11)	0.0073 (10)	0.0059 (10)
C13'	0.0272 (10)	0.0571 (14)	0.0367 (10)	0.0039 (9)	−0.0007 (9)	0.0101 (10)
C14'	0.0434 (13)	0.0680 (17)	0.0464 (12)	−0.0034 (12)	−0.0112 (10)	0.0012 (12)

O1—C1	1.198 (3)	C8—H8A	0.9500
O2—C1	1.351 (3)	C9—C10	1.388 (5)
O2—C4	1.451 (3)	C9—H9A	0.9500
O3—C1'	1.386 (2)	C10—C11	1.390 (4)
O3—C3	1.440 (2)	C10—H10A	0.9500
O4—C1'	1.417 (2)	C11—H11A	0.9500
O4—C5'	1.424 (2)	C1'—C2'	1.512 (3)
O5—C7'	1.352 (3)	C1'—H1'A	1.0000
O5—C2'	1.440 (2)	C2'—C3'	1.514 (3)
O6—C9'	1.355 (3)	C2'—H2'A	1.0000
O6—C3'	1.441 (2)	C3'—C4'	1.517 (3)
O7—C11'	1.352 (2)	C3'—H3'A	1.0000
O7—C4'	1.440 (2)	C4'—C5'	1.527 (3)
O8—C13'	1.335 (3)	C4'—H4'A	1.0000
O8—C6'	1.436 (3)	C5'—C6'	1.509 (3)
O9—C7'	1.199 (3)	C5'—H5'A	1.0000
O10—C9'	1.188 (3)	C6'—H6'A	0.9900
O11—C11'	1.189 (3)	C6'—H6'B	0.9900
O12—C13'	1.205 (3)	C7'—C8'	1.493 (3)
C1—C2	1.513 (3)	C8'—H8'A	0.9800
C2—C3	1.517 (3)	C8'—H8'B	0.9800
C2—C5	1.532 (3)	C8'—H8'C	0.9800
C2—H2A	1.0000	C9'—C10'	1.504 (4)
C3—C4	1.515 (3)	C10'—H10B	0.9800
C3—H3A	1.0000	C10'—H10C	0.9800
C4—H4A	0.9900	C10'—H10D	0.9800
C4—H4B	0.9900	C11'—C12'	1.501 (3)
C5—C6	1.506 (3)	C12'—H12A	0.9800
C5—H5A	0.9900	C12'—H12B	0.9800
C5—H5B	0.9900	C12'—H12C	0.9800
C6—C7	1.386 (3)	C13'—C14'	1.480 (4)
C6—C11	1.396 (3)	C14'—H14A	0.9800
C7—C8	1.387 (3)	C14'—H14B	0.9800
C7—H7A	0.9500	C14'—H14C	0.9800
C8—C9	1.379 (5)
C1—O2—C4	109.73 (15)	C1'—C2'—H2'A	109.8
C1'—O3—C3	114.93 (15)	C3'—C2'—H2'A	109.8
C1'—O4—C5'	111.88 (14)	O6—C3'—C2'	107.32 (15)
C7'—O5—C2'	117.84 (15)	O6—C3'—C4'	108.99 (15)
C9'—O6—C3'	117.33 (17)	C2'—C3'—C4'	110.30 (15)
C11'—O7—C4'	117.49 (16)	O6—C3'—H3'A	110.1
C13'—O8—C6'	117.98 (17)	C2'—C3'—H3'A	110.1
O1—C1—O2	121.81 (19)	C4'—C3'—H3'A	110.1
O1—C1—C2	129.1 (2)	O7—C4'—C3'	108.49 (15)
O2—C1—C2	109.08 (17)	O7—C4'—C5'	109.19 (15)
C1—C2—C3	101.56 (16)	C3'—C4'—C5'	110.08 (15)
C1—C2—C5	115.21 (17)	O7—C4'—H4'A	109.7
C3—C2—C5	118.49 (16)	C3'—C4'—H4'A	109.7
C1—C2—H2A	106.9	C5'—C4'—H4'A	109.7
C3—C2—H2A	106.9	O4—C5'—C6'	107.93 (16)
C5—C2—H2A	106.9	O4—C5'—C4'	107.57 (15)
O3—C3—C4	109.95 (16)	C6'—C5'—C4'	112.99 (16)
O3—C3—C2	105.78 (15)	O4—C5'—H5'A	109.4
C4—C3—C2	100.91 (16)	C6'—C5'—H5'A	109.4
O3—C3—H3A	113.1	C4'—C5'—H5'A	109.4
C4—C3—H3A	113.1	O8—C6'—C5'	107.95 (16)
C2—C3—H3A	113.1	O8—C6'—H6'A	110.1
O2—C4—C3	104.82 (16)	C5'—C6'—H6'A	110.1
O2—C4—H4A	110.8	O8—C6'—H6'B	110.1
C3—C4—H4A	110.8	C5'—C6'—H6'B	110.1
O2—C4—H4B	110.8	H6'A—C6'—H6'B	108.4
C3—C4—H4B	110.8	O9—C7'—O5	123.58 (19)
H4A—C4—H4B	108.9	O9—C7'—C8'	125.6 (2)
C6—C5—C2	111.99 (16)	O5—C7'—C8'	110.83 (18)
C6—C5—H5A	109.2	C7'—C8'—H8'A	109.5
C2—C5—H5A	109.2	C7'—C8'—H8'B	109.5
C6—C5—H5B	109.2	H8'A—C8'—H8'B	109.5
C2—C5—H5B	109.2	C7'—C8'—H8'C	109.5
H5A—C5—H5B	107.9	H8'A—C8'—H8'C	109.5
C7—C6—C11	118.7 (2)	H8'B—C8'—H8'C	109.5
C7—C6—C5	120.4 (2)	O10—C9'—O6	124.0 (2)
C11—C6—C5	120.9 (2)	O10—C9'—C10'	126.8 (2)
C8—C7—C6	120.6 (2)	O6—C9'—C10'	109.2 (2)
C8—C7—H7A	119.7	C9'—C10'—H10B	109.5
C6—C7—H7A	119.7	C9'—C10'—H10C	109.5
C9—C8—C7	120.9 (3)	H10B—C10'—H10C	109.5
C9—C8—H8A	119.6	C9'—C10'—H10D	109.5
C7—C8—H8A	119.6	H10B—C10'—H10D	109.5
C8—C9—C10	118.9 (2)	H10C—C10'—H10D	109.5
C8—C9—H9A	120.5	O11—C11'—O7	123.3 (2)
C10—C9—H9A	120.5	O11—C11'—C12'	126.1 (2)
C9—C10—C11	120.6 (3)	O7—C11'—C12'	110.57 (19)
C9—C10—H10A	119.7	C11'—C12'—H12A	109.5
C11—C10—H10A	119.7	C11'—C12'—H12B	109.5
C10—C11—C6	120.3 (3)	H12A—C12'—H12B	109.5
C10—C11—H11A	119.9	C11'—C12'—H12C	109.5
C6—C11—H11A	119.9	H12A—C12'—H12C	109.5
O3—C1'—O4	107.78 (15)	H12B—C12'—H12C	109.5
O3—C1'—C2'	107.49 (16)	O12—C13'—O8	122.7 (2)
O4—C1'—C2'	109.14 (14)	O12—C13'—C14'	126.4 (2)
O3—C1'—H1'A	110.8	O8—C13'—C14'	110.89 (19)
O4—C1'—H1'A	110.8	C13'—C14'—H14A	109.5
C2'—C1'—H1'A	110.8	C13'—C14'—H14B	109.5
O5—C2'—C1'	109.72 (15)	H14A—C14'—H14B	109.5
O5—C2'—C3'	106.54 (15)	C13'—C14'—H14C	109.5
C1'—C2'—C3'	111.08 (16)	H14A—C14'—H14C	109.5
O5—C2'—H2'A	109.8	H14B—C14'—H14C	109.5
C4—O2—C1—O1	176.02 (19)	O3—C1'—C2'—O5	−70.08 (18)
C4—O2—C1—C2	−4.4 (2)	O4—C1'—C2'—O5	173.29 (14)
O1—C1—C2—C3	−154.5 (2)	O3—C1'—C2'—C3'	172.38 (15)
O2—C1—C2—C3	25.89 (19)	O4—C1'—C2'—C3'	55.8 (2)
O1—C1—C2—C5	−25.2 (3)	C9'—O6—C3'—C2'	−132.97 (19)
O2—C1—C2—C5	155.26 (16)	C9'—O6—C3'—C4'	107.6 (2)
C1'—O3—C3—C4	−82.37 (19)	O5—C2'—C3'—O6	71.25 (18)
C1'—O3—C3—C2	169.45 (14)	C1'—C2'—C3'—O6	−169.29 (14)
C1—C2—C3—O3	79.21 (17)	O5—C2'—C3'—C4'	−170.14 (15)
C5—C2—C3—O3	−48.1 (2)	C1'—C2'—C3'—C4'	−50.7 (2)
C1—C2—C3—C4	−35.34 (18)	C11'—O7—C4'—C3'	108.25 (18)
C5—C2—C3—C4	−162.61 (17)	C11'—O7—C4'—C5'	−131.76 (18)
C1—O2—C4—C3	−19.3 (2)	O6—C3'—C4'—O7	−70.62 (18)
O3—C3—C4—O2	−77.30 (19)	C2'—C3'—C4'—O7	171.80 (15)
C2—C3—C4—O2	34.09 (19)	O6—C3'—C4'—C5'	169.95 (14)
C1—C2—C5—C6	169.70 (17)	C2'—C3'—C4'—C5'	52.4 (2)
C3—C2—C5—C6	−69.8 (2)	C1'—O4—C5'—C6'	−171.17 (16)
C2—C5—C6—C7	−78.9 (2)	C1'—O4—C5'—C4'	66.61 (18)
C2—C5—C6—C11	98.9 (2)	O7—C4'—C5'—O4	−177.99 (14)
C11—C6—C7—C8	−0.8 (3)	C3'—C4'—C5'—O4	−58.99 (19)
C5—C6—C7—C8	177.1 (2)	O7—C4'—C5'—C6'	63.0 (2)
C6—C7—C8—C9	0.9 (4)	C3'—C4'—C5'—C6'	−178.01 (16)
C7—C8—C9—C10	−0.1 (4)	C13'—O8—C6'—C5'	−127.09 (18)
C8—C9—C10—C11	−1.0 (4)	O4—C5'—C6'—O8	−61.5 (2)
C9—C10—C11—C6	1.1 (4)	C4'—C5'—C6'—O8	57.4 (2)
C7—C6—C11—C10	−0.3 (3)	C2'—O5—C7'—O9	−2.1 (3)
C5—C6—C11—C10	−178.1 (2)	C2'—O5—C7'—C8'	176.30 (19)
C3—O3—C1'—O4	−77.32 (18)	C3'—O6—C9'—O10	3.2 (4)
C3—O3—C1'—C2'	165.16 (15)	C3'—O6—C9'—C10'	−176.3 (2)
C5'—O4—C1'—O3	178.36 (14)	C4'—O7—C11'—O11	4.8 (3)
C5'—O4—C1'—C2'	−65.20 (19)	C4'—O7—C11'—C12'	−174.66 (18)
C7'—O5—C2'—C1'	106.05 (19)	C6'—O8—C13'—O12	−8.6 (3)
C7'—O5—C2'—C3'	−133.61 (17)	C6'—O8—C13'—C14'	173.88 (18)