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

Zhang, F.; Zhong, J.; Han, B.; Yin, D.; Huang, H.

doi:10.1107/S1600536810006628

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o704

doi:10.1107/S1600536810006628

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(2R,3S)-2-Benzyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)butanolide

Feng Zhang,^a Jialiang Zhong,^b Bei Han,^a Dali Yin ^a and Haihong Huang ^a ^*

^aInstitute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, People's Republic of China, and ^bShanghai Institute of Pharmaceutical Industry, Shanghai 200040, People's Republic of China
^*Correspondence e-mail: joyce@imm.ac.cn

(Received 8 February 2010; accepted 21 February 2010; online 27 February 2010)

The title compound, C₂₅H₃₀O₁₂, 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_r = 522.49
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.036
wR(F²) = 0.102
S = 1.07
4102 reflections
334 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −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.

Supporting information

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

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

checkCIF report

Comment top

The title compound was found to have a significant hepatoprotective effect, comparable to the natural product Goodyeroside A (Du & Irinon, 2008). Recently, the compound was successfully crystallized from a petroleum ether/EtOAc mixture, yielding crystals suitable for X-ray analysis.

Fig.1 shows the molecular structure of the title compound with atomic numbering scheme. The bond lengths and angles are in agreement with reported literature values (Table 1) (Allen et al., 1987). The benzene ring (C6—C11) is essentially planar, with r.m.s deviations of 0.0078 (14) Å. The five-membered ring (C1—C4/O2) has an envelope conformation with the C3 atom out of plane and the six-membered ring (C1'-C5'/O4) is in its chair conformation. The dihedral angles between the various rings in the title compound are as follows, where the first atom is used to identify its five- or six- membered ring: C1/C6 112.9 (1)°; C1/C1' 110.1 (1)°; C6/C1' 13.1 (1)°.

In order to determine the absolute configuration of the title compound, the data collection was performed using Cu Kα. The absolute configuration is confirmed by the Flack parameter 0.05 (17) and Hooft parameter 0.04 (6) (Flack, 1983; Hooft et al., 2008).

Related literature top

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 top

To a solution of Ethyl (2R,3S)-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-2- benzyl-4-hydroxybutanoate (1.0 equiv) in 1,4-dioxane (10 ml) was added 4-methylbenzenesulfonic acid (1.0 equiv), then the solution was stirred at room temperature for 2 days. After removal of the solvent in vacuo, the residue was purified by column chromatography. White crystals suitable for X-ray analysis were obtained by slow evaportion of a petroleum ether/EtOAc solution over a period of two weeks (Saito et al., 1992; Kazumasa et al., 2000; Schmidt, 1986; Corey & Venkateswarlu, 1972; Fernandez et al., 1997).

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); 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 (Sheldrick, 2008).

Figures top

Fig. 1. View of the title compound showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

(2R,3S)-2-Benzyl-3-(2,3,4,6-tetra-O-acetyl-β-D- glucopyranosyloxy)butanolide top

Crystal data top

C₂₅H₃₀O₁₂	F(000) = 1104
M_r = 522.49	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0654P)² + 0.5803P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
4102 reflections	Δρ_max = 0.34 e Å⁻³
334 parameters	Δρ_min = −0.22 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1417 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.05 (17)

Crystal data top

C₂₅H₃₀O₁₂	V = 2706.05 (8) Å³
M_r = 522.49	Z = 4
Orthorhombic, P2₁2₁2₁	Cu Kα radiation
a = 10.6142 (2) Å	µ = 0.87 mm⁻¹
b = 11.0984 (2) Å	T = 153 K
c = 22.9714 (3) Å	0.15 × 0.15 × 0.10 mm

Data collection top

Mac dip 2030b diffractometer	4102 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	4015 reflections with I > 2σ(I)
T_min = 0.880, T_max = 0.918	R_int = 0.016
7246 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.102	Δρ_max = 0.34 e Å⁻³
S = 1.07	Δρ_min = −0.22 e Å⁻³
4102 reflections	Absolute structure: Flack (1983), 1417 Friedel pairs
334 parameters	Absolute structure parameter: 0.05 (17)
0 restraints

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₂₅H₃₀O₁₂
M_r	522.49
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	153
a, b, c (Å)	10.6142 (2), 11.0984 (2), 22.9714 (3)
V (Å³)	2706.05 (8)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.87
Crystal size (mm)	0.15 × 0.15 × 0.10

Data collection
Diffractometer	Mac dip 2030b diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.880, 0.918
No. of measured, independent and observed [I > 2σ(I)] reflections	7246, 4102, 4015
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.593

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.102, 1.07
No. of reflections	4102
No. of parameters	334
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.22
Absolute structure	Flack (1983), 1417 Friedel pairs
Absolute structure parameter	0.05 (17)

Computer programs: DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976) and PLATON (Spek, 2009).

Selected geometric parameters (Å, º) top

O1—C1	1.198 (3)	C8—C9	1.379 (5)
O2—C1	1.351 (3)	C9—C10	1.388 (5)
O2—C4	1.451 (3)	C10—C11	1.390 (4)
O4—C1'	1.417 (2)	C1'—C2'	1.512 (3)
O4—C5'	1.424 (2)	C2'—C3'	1.514 (3)
C6—C7	1.386 (3)	C3'—C4'	1.517 (3)
C6—C11	1.396 (3)	C4'—C5'	1.527 (3)
C7—C8	1.387 (3)

O1—C1—O2	121.81 (19)	C9—C10—C11	120.6 (3)
C1—C2—C5	115.21 (17)	O3—C1'—O4	107.78 (15)
O3—C3—C4	109.95 (16)	O4—C1'—C2'	109.14 (14)
C7—C6—C5	120.4 (2)	C3'—C4'—C5'	110.08 (15)
C9—C8—C7	120.9 (3)

Acknowledgements

The authors extend their hearty thanks to Ms Lin Ziyun and Mr Li Peng for their advice and encouragement during the work.

References

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