2,3,4,6-Tetra-O-acetyl-β-d-galacto­pyrano­syl butyrate

Cui, Y.-L.; Xu, M.-H.; Mao, J.-W.; Yu, Y.-P.

doi:10.1107/S1600536811055814

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o320

doi:10.1107/S1600536811055814

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2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl butyrate

Yan-Li Cui,^a ^* Ming-Han Xu,^a Jian-Wei Mao ^b and Yong-Ping Yu ^c

^aDepartment of Chemistry, Zhejiang University, People's Republic of China, ^bDepartment of Biological and Chemical Engineering, Zhejiang University of Science and Technology, People's Republic of China, and ^cCollege of Pharmaceutical Sciences, Zhejiang University, People's Republic of China
^*Correspondence e-mail: zjhzcyl@tom.com

(Received 6 December 2011; accepted 27 December 2011; online 11 January 2012)

The title compound, C₁₈H₂₆O₁₁, was synthesized by a condensation reaction of 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide and butyric acid. The acetoxymethyl and butyrate groups are located on the same side of the pyran ring, showing the β configuration for the D-glycosyl ester; the butyl group adopts an extend conformation, the C—C—C—C torsion angle being 179.1 (7)°. In the crystal, the molecules are linked by weak C—H⋯O hydrogen bonds.

Related literature

For the total synthesis of glycosyl esters, see: Li et al. (1992 ); Smith et al. (1986 ). For the anti-tumor activities of glycosyl esters, see: Feldman et al. (2000 ). For related structures, see: Sambaiah et al. (2001 ); Parkanyi et al. (1987 ); Roslund et al. (2004 ); Liu et al. (2009 ); Kumar et al. (2005). For the synthesis, see: Loganathan & Trivedi (1987 ).

Experimental

Crystal data

C₁₈H₂₆O₁₁
M_r = 418.39
Monoclinic, P 2₁
a = 9.2079 (9) Å
b = 8.5034 (5) Å
c = 14.3199 (12) Å
β = 100.804 (9)°
V = 1101.35 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 294 K
0.38 × 0.32 × 0.25 mm

Data collection

Oxford Diffraction Xcalibur Atlas Gemini Ultra diffractometer
6393 measured reflections
2160 independent reflections
1582 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.147
S = 1.03
2160 reflections
268 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O11ⁱ	0.98	2.47	3.362 (5)	152
C5—H5⋯O11ⁱ	0.98	2.57	3.443 (6)	149
C11—H11B⋯O5ⁱⁱ	0.96	2.49	3.293 (7)	141
C16—H16C⋯O9ⁱⁱⁱ	0.96	2.60	3.441 (7)	147
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+1]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811055814/xu5405sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811055814/xu5405Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811055814/xu5405Isup3.cml

checkCIF report

Comment top

Carbohydrates provide excellent platforms upon which to explore unique features for the drug-discovery process. Numerous natural glycosyl esters such as phyllanthostatin family (Li et al., 1992) and dimeric ellagitannin coriariin A have been total synthetized (Smith et al., 1986). Some of them were proved to possess anti-tumor activities (Feldman et al., 2000). Also the glycosyl esters have long drawn attention as potential glycosyl donors. Several crystal structures of carbohydrate derivatives were reported (Sambaiah et al., 2001; Parkanyi et al., 1987; Roslund et al., 2004; Liu et al., 2009; Kumar et al., 2005). Recently we have synthetized the title compound and report its crystal structure herein.

The molecular structure of the title compound is shown in Fig. 1. In the molecule, the acetoxymethyl and butyrate groups are located on the same side of the pyran ring, showing the β-configuration for the D-glycosyl ester; the butyl group adopts an extend conformation, the C6–C7–C8–C9 torsion angle being 179.1 (7)°. The molecules are linked by weak C—H···O hydrogen bonding in the crystal.

Related literature top

For the total synthesis of glycosyl esters, see: Li et al. (1992); Smith et al. (1986). For the anti-tumor activities of glycosyl esters, see: Feldman et al. (2000). For related structures, see: Sambaiah et al. (2001); Parkanyi et al. (1987); Roslund et al. (2004); Liu et al. (2009); Kumar et al. (2005). For the synthesis, see: Loganathan & Trivedi (1987).

Experimental top

A solution of butyric acid (48.8 µl, 0.53 mmol), tetrabutylammonium iodide (26.7 mg, 0.07 mmol) and 5% aqueous sodium hydroxide (2 ml, 17.1 mg, 1.35 mmol) in dichloromethane (2 ml) was vigorously stirred at room temperature, then 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide (145.1 mg, 0.35 mmol) was added. The mixture was stirred for 30 h, the two phases (dichloromethane phase and water phase) were then separated. The organic layer was washed with a sodium hydroxide aqueous solution (5%) and water for several times, dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (petroether/EtOAc = 2:1) to afford the title compound (Fig. 2). Single crystals suitable for X-ray data collection were obtained by slow evaporation from an ether solution (Loganathan et al., 1987).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I) with 30% probability displacement ellipsoids.
	Fig. 2. Reaction scheme.

(2S,3R,4S,5S,6R)-3,4,5-triacetoxy- 6-(acetoxymethyl)oxinan-2-yl butyrate top

Crystal data top

C₁₈H₂₆O₁₁	F(000) = 444
M_r = 418.39	D_x = 1.262 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3799 reflections
a = 9.2079 (9) Å	θ = 3.2–26.4°
b = 8.5034 (5) Å	µ = 0.11 mm⁻¹
c = 14.3199 (12) Å	T = 294 K
β = 100.804 (9)°	Block, colorless
V = 1101.35 (16) Å³	0.38 × 0.32 × 0.25 mm
Z = 2

Data collection top

Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer	1582 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.028
Graphite monochromator	θ_max = 25.4°, θ_min = 2.9°
Detector resolution: 10.3592 pixels mm^-1	h = −11→8
ω scans	k = −10→9
6393 measured reflections	l = −16→17
2160 independent 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)] = 0.048	H-atom parameters constrained
wR(F²) = 0.147	w = 1/[σ²(F_o²) + (0.0855P)² + 0.0985P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.002
2160 reflections	Δρ_max = 0.35 e Å⁻³
268 parameters	Δρ_min = −0.21 e Å⁻³
1 restraint	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.022 (6)

Crystal data top

C₁₈H₂₆O₁₁	V = 1101.35 (16) Å³
M_r = 418.39	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 9.2079 (9) Å	µ = 0.11 mm⁻¹
b = 8.5034 (5) Å	T = 294 K
c = 14.3199 (12) Å	0.38 × 0.32 × 0.25 mm
β = 100.804 (9)°

Data collection top

Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer	1582 reflections with I > 2σ(I)
6393 measured reflections	R_int = 0.028
2160 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	1 restraint
wR(F²) = 0.147	H-atom parameters constrained
S = 1.03	Δρ_max = 0.35 e Å⁻³
2160 reflections	Δρ_min = −0.21 e Å⁻³
268 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
O1	0.1960 (3)	0.9067 (3)	0.2033 (2)	0.0627 (8)
O2	0.2171 (3)	0.8828 (4)	0.3617 (2)	0.0669 (8)
O3	−0.0223 (5)	0.8472 (6)	0.3587 (3)	0.1095 (14)
O4	0.2776 (3)	1.2097 (3)	0.3854 (2)	0.0599 (7)
O5	0.4753 (4)	1.1092 (5)	0.4784 (2)	0.0989 (13)
O6	0.4015 (3)	1.3413 (3)	0.23619 (19)	0.0606 (7)
O7	0.2592 (4)	1.5007 (4)	0.1320 (3)	0.0843 (10)
O8	0.4303 (3)	1.0527 (3)	0.13984 (19)	0.0607 (7)
O9	0.5101 (5)	1.2274 (5)	0.0433 (3)	0.1129 (15)
O10	0.1343 (4)	1.0060 (4)	−0.0433 (2)	0.0778 (9)
O11	0.0730 (4)	0.8056 (4)	−0.1411 (2)	0.0833 (10)
C1	0.1872 (5)	0.9923 (5)	0.2865 (3)	0.0579 (10)
H1	0.0883	1.0375	0.2824	0.069*
C2	0.3038 (4)	1.1195 (5)	0.3053 (3)	0.0516 (9)
H2	0.4030	1.0731	0.3185	0.062*
C3	0.2868 (4)	1.2263 (4)	0.2199 (3)	0.0524 (10)
H3	0.1912	1.2800	0.2127	0.063*
C4	0.2904 (4)	1.1312 (5)	0.1311 (3)	0.0553 (10)
H4	0.2741	1.1999	0.0751	0.066*
C5	0.1711 (5)	1.0062 (5)	0.1214 (3)	0.0592 (10)
H5	0.0749	1.0579	0.1171	0.071*
C6	0.1034 (6)	0.8206 (6)	0.3940 (3)	0.0691 (12)
C7	0.1506 (7)	0.7109 (7)	0.4739 (3)	0.0898 (16)
H7A	0.2396	0.6558	0.4658	0.108*
H7B	0.0737	0.6338	0.4764	0.108*
C8	0.1820 (10)	0.8143 (11)	0.5717 (4)	0.139 (3)
H8A	0.2591	0.8907	0.5683	0.166*
H8B	0.0931	0.8714	0.5779	0.166*
C9	0.2258 (9)	0.7182 (11)	0.6526 (4)	0.135 (3)
H9A	0.3178	0.6677	0.6490	0.202*
H9B	0.1515	0.6398	0.6548	0.202*
H9C	0.2378	0.7817	0.7090	0.202*
C10	0.3699 (5)	1.1938 (6)	0.4686 (3)	0.0640 (11)
C11	0.3271 (7)	1.2933 (7)	0.5437 (3)	0.0857 (15)
H11A	0.2395	1.3516	0.5177	0.129*
H11B	0.4059	1.3650	0.5674	0.129*
H11C	0.3080	1.2280	0.5947	0.129*
C12	0.3736 (6)	1.4773 (5)	0.1855 (4)	0.0698 (12)
C13	0.4984 (7)	1.5887 (8)	0.2062 (5)	0.114 (2)
H13A	0.5798	1.5396	0.2476	0.171*
H13B	0.4683	1.6807	0.2364	0.171*
H13C	0.5283	1.6182	0.1479	0.171*
C14	0.1652 (6)	0.9010 (6)	0.0361 (3)	0.0709 (12)
H14A	0.2590	0.8479	0.0381	0.085*
H14B	0.0878	0.8229	0.0331	0.085*
C15	0.5298 (5)	1.1116 (6)	0.0906 (3)	0.0697 (12)
C16	0.6667 (5)	1.0135 (6)	0.1061 (4)	0.0839 (15)
H16A	0.7105	1.0135	0.1724	0.126*
H16B	0.7356	1.0562	0.0701	0.126*
H16C	0.6420	0.9077	0.0856	0.126*
C17	0.0882 (5)	0.9440 (6)	−0.1293 (3)	0.0653 (12)
C18	0.0590 (7)	1.0649 (8)	−0.2023 (3)	0.0884 (15)
H18A	0.1422	1.1347	−0.1960	0.133*
H18B	−0.0274	1.1233	−0.1950	0.133*
H18C	0.0429	1.0165	−0.2639	0.133*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0752 (19)	0.0537 (15)	0.0613 (17)	−0.0060 (14)	0.0180 (14)	0.0060 (14)
O2	0.0644 (18)	0.0700 (19)	0.0679 (18)	−0.0023 (15)	0.0161 (14)	0.0242 (16)
O3	0.083 (3)	0.128 (4)	0.126 (3)	−0.001 (2)	0.042 (2)	0.034 (3)
O4	0.0617 (17)	0.0651 (17)	0.0542 (15)	0.0114 (14)	0.0146 (12)	0.0022 (14)
O5	0.084 (2)	0.123 (3)	0.082 (2)	0.028 (3)	−0.0029 (19)	−0.015 (2)
O6	0.0665 (18)	0.0549 (16)	0.0591 (15)	−0.0089 (13)	0.0083 (13)	0.0000 (14)
O7	0.088 (2)	0.068 (2)	0.093 (2)	−0.0005 (18)	0.008 (2)	0.0190 (19)
O8	0.0660 (18)	0.0577 (15)	0.0618 (16)	0.0012 (13)	0.0209 (13)	0.0072 (14)
O9	0.110 (3)	0.112 (3)	0.131 (3)	0.010 (3)	0.061 (3)	0.055 (3)
O10	0.106 (2)	0.0663 (19)	0.0575 (17)	−0.0130 (18)	0.0052 (16)	0.0012 (16)
O11	0.086 (2)	0.080 (2)	0.079 (2)	0.0041 (19)	0.0024 (17)	−0.0216 (19)
C1	0.056 (2)	0.061 (2)	0.056 (2)	0.002 (2)	0.0102 (18)	0.009 (2)
C2	0.053 (2)	0.053 (2)	0.049 (2)	0.0056 (18)	0.0099 (16)	0.0022 (18)
C3	0.050 (2)	0.052 (2)	0.054 (2)	0.0009 (18)	0.0065 (17)	0.0065 (18)
C4	0.060 (2)	0.053 (2)	0.052 (2)	0.0007 (19)	0.0090 (17)	0.0099 (19)
C5	0.070 (3)	0.053 (2)	0.054 (2)	−0.006 (2)	0.0084 (19)	0.0048 (19)
C6	0.075 (3)	0.073 (3)	0.063 (3)	−0.003 (3)	0.023 (2)	0.005 (2)
C7	0.103 (4)	0.091 (3)	0.076 (3)	−0.020 (3)	0.018 (3)	0.024 (3)
C8	0.197 (9)	0.135 (6)	0.081 (4)	0.022 (6)	0.016 (5)	0.021 (4)
C9	0.153 (7)	0.160 (8)	0.095 (4)	−0.013 (6)	0.033 (4)	−0.010 (5)
C10	0.063 (3)	0.070 (3)	0.062 (3)	−0.003 (2)	0.018 (2)	0.004 (2)
C11	0.114 (4)	0.087 (3)	0.061 (3)	−0.007 (3)	0.028 (3)	−0.007 (3)
C12	0.082 (3)	0.056 (3)	0.075 (3)	−0.010 (2)	0.023 (3)	0.002 (2)
C13	0.125 (5)	0.087 (4)	0.122 (5)	−0.041 (4)	0.005 (4)	0.014 (4)
C14	0.089 (3)	0.057 (2)	0.064 (3)	−0.008 (2)	0.007 (2)	0.004 (2)
C15	0.078 (3)	0.065 (3)	0.073 (3)	−0.014 (2)	0.030 (2)	−0.003 (3)
C16	0.075 (3)	0.080 (3)	0.106 (4)	0.000 (3)	0.040 (3)	−0.010 (3)
C17	0.059 (3)	0.076 (3)	0.061 (3)	−0.004 (2)	0.012 (2)	−0.006 (2)
C18	0.097 (4)	0.101 (4)	0.066 (3)	0.002 (3)	0.012 (3)	0.005 (3)

Geometric parameters (Å, º) top

O1—C1	1.412 (5)	C7—C8	1.634 (9)
O1—C5	1.429 (5)	C7—H7A	0.9700
O2—C6	1.331 (5)	C7—H7B	0.9700
O2—C1	1.412 (5)	C8—C9	1.413 (9)
O3—C6	1.195 (6)	C8—H8A	0.9700
O4—C10	1.334 (5)	C8—H8B	0.9700
O4—C2	1.437 (5)	C9—H9A	0.9600
O5—C10	1.195 (6)	C9—H9B	0.9600
O6—C12	1.363 (5)	C9—H9C	0.9600
O6—C3	1.426 (5)	C10—C11	1.478 (7)
O7—C12	1.197 (6)	C11—H11A	0.9600
O8—C15	1.353 (5)	C11—H11B	0.9600
O8—C4	1.435 (5)	C11—H11C	0.9600
O9—C15	1.190 (6)	C12—C13	1.476 (7)
O10—C17	1.334 (5)	C13—H13A	0.9600
O10—C14	1.432 (5)	C13—H13B	0.9600
O11—C17	1.193 (6)	C13—H13C	0.9600
C1—C2	1.513 (6)	C14—H14A	0.9700
C1—H1	0.9800	C14—H14B	0.9700
C2—C3	1.507 (5)	C15—C16	1.492 (7)
C2—H2	0.9800	C16—H16A	0.9600
C3—C4	1.513 (6)	C16—H16B	0.9600
C3—H3	0.9800	C16—H16C	0.9600
C4—C5	1.516 (6)	C17—C18	1.454 (7)
C4—H4	0.9800	C18—H18A	0.9600
C5—C14	1.506 (6)	C18—H18B	0.9600
C5—H5	0.9800	C18—H18C	0.9600
C6—C7	1.477 (7)

C1—O1—C5	111.2 (3)	H8A—C8—H8B	108.0
C6—O2—C1	118.3 (3)	C8—C9—H9A	109.5
C10—O4—C2	119.0 (3)	C8—C9—H9B	109.5
C12—O6—C3	115.7 (3)	H9A—C9—H9B	109.5
C15—O8—C4	117.8 (3)	C8—C9—H9C	109.5
C17—O10—C14	118.0 (4)	H9A—C9—H9C	109.5
O2—C1—O1	105.7 (3)	H9B—C9—H9C	109.5
O2—C1—C2	107.8 (3)	O5—C10—O4	122.2 (4)
O1—C1—C2	111.6 (3)	O5—C10—C11	125.5 (4)
O2—C1—H1	110.6	O4—C10—C11	112.3 (4)
O1—C1—H1	110.6	C10—C11—H11A	109.5
C2—C1—H1	110.6	C10—C11—H11B	109.5
O4—C2—C3	108.6 (3)	H11A—C11—H11B	109.5
O4—C2—C1	107.7 (3)	C10—C11—H11C	109.5
C3—C2—C1	108.9 (3)	H11A—C11—H11C	109.5
O4—C2—H2	110.5	H11B—C11—H11C	109.5
C3—C2—H2	110.5	O7—C12—O6	122.5 (4)
C1—C2—H2	110.5	O7—C12—C13	125.5 (5)
O6—C3—C2	108.6 (3)	O6—C12—C13	112.0 (4)
O6—C3—C4	111.8 (3)	C12—C13—H13A	109.5
C2—C3—C4	110.2 (3)	C12—C13—H13B	109.5
O6—C3—H3	108.7	H13A—C13—H13B	109.5
C2—C3—H3	108.7	C12—C13—H13C	109.5
C4—C3—H3	108.7	H13A—C13—H13C	109.5
O8—C4—C3	109.6 (3)	H13B—C13—H13C	109.5
O8—C4—C5	107.7 (3)	O10—C14—C5	104.2 (3)
C3—C4—C5	108.8 (3)	O10—C14—H14A	110.9
O8—C4—H4	110.2	C5—C14—H14A	110.9
C3—C4—H4	110.2	O10—C14—H14B	110.9
C5—C4—H4	110.2	C5—C14—H14B	110.9
O1—C5—C14	106.8 (3)	H14A—C14—H14B	108.9
O1—C5—C4	109.7 (3)	O9—C15—O8	123.8 (5)
C14—C5—C4	113.9 (4)	O9—C15—C16	125.6 (5)
O1—C5—H5	108.8	O8—C15—C16	110.6 (4)
C14—C5—H5	108.8	C15—C16—H16A	109.5
C4—C5—H5	108.8	C15—C16—H16B	109.5
O3—C6—O2	122.7 (4)	H16A—C16—H16B	109.5
O3—C6—C7	124.6 (5)	C15—C16—H16C	109.5
O2—C6—C7	112.6 (5)	H16A—C16—H16C	109.5
C6—C7—C8	107.7 (5)	H16B—C16—H16C	109.5
C6—C7—H7A	110.2	O11—C17—O10	121.9 (5)
C8—C7—H7A	110.2	O11—C17—C18	126.5 (5)
C6—C7—H7B	110.2	O10—C17—C18	111.6 (4)
C8—C7—H7B	110.2	C17—C18—H18A	109.5
H7A—C7—H7B	108.5	C17—C18—H18B	109.5
C9—C8—C7	111.6 (7)	H18A—C18—H18B	109.5
C9—C8—H8A	109.3	C17—C18—H18C	109.5
C7—C8—H8A	109.3	H18A—C18—H18C	109.5
C9—C8—H8B	109.3	H18B—C18—H18C	109.5
C7—C8—H8B	109.3

C6—O2—C1—O1	−99.1 (4)	C1—O1—C5—C14	−173.6 (3)
C6—O2—C1—C2	141.5 (4)	C1—O1—C5—C4	62.5 (4)
C5—O1—C1—O2	−178.6 (3)	O8—C4—C5—O1	59.6 (4)
C5—O1—C1—C2	−61.7 (4)	C3—C4—C5—O1	−59.2 (4)
C10—O4—C2—C3	−134.7 (4)	O8—C4—C5—C14	−60.1 (4)
C10—O4—C2—C1	107.5 (4)	C3—C4—C5—C14	−178.9 (3)
O2—C1—C2—O4	−69.9 (4)	C1—O2—C6—O3	4.1 (7)
O1—C1—C2—O4	174.5 (3)	C1—O2—C6—C7	−178.8 (4)
O2—C1—C2—C3	172.6 (3)	O3—C6—C7—C8	−96.6 (7)
O1—C1—C2—C3	57.0 (4)	O2—C6—C7—C8	86.3 (6)
C12—O6—C3—C2	−156.7 (3)	C6—C7—C8—C9	179.1 (7)
C12—O6—C3—C4	81.5 (4)	C2—O4—C10—O5	1.4 (7)
O4—C2—C3—O6	65.8 (4)	C2—O4—C10—C11	−179.6 (4)
C1—C2—C3—O6	−177.2 (3)	C3—O6—C12—O7	1.4 (6)
O4—C2—C3—C4	−171.4 (3)	C3—O6—C12—C13	−179.5 (5)
C1—C2—C3—C4	−54.4 (4)	C17—O10—C14—C5	−164.4 (4)
C15—O8—C4—C3	−104.4 (4)	O1—C5—C14—O10	177.8 (3)
C15—O8—C4—C5	137.4 (4)	C4—C5—C14—O10	−60.9 (5)
O6—C3—C4—O8	59.4 (4)	C4—O8—C15—O9	2.7 (7)
C2—C3—C4—O8	−61.5 (4)	C4—O8—C15—C16	−178.6 (4)
O6—C3—C4—C5	177.0 (3)	C14—O10—C17—O11	−0.2 (7)
C2—C3—C4—C5	56.1 (4)	C14—O10—C17—C18	179.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O11ⁱ	0.98	2.47	3.362 (5)	152
C5—H5···O11ⁱ	0.98	2.57	3.443 (6)	149
C11—H11B···O5ⁱⁱ	0.96	2.49	3.293 (7)	141
C16—H16C···O9ⁱⁱⁱ	0.96	2.60	3.441 (7)	147

Symmetry codes: (i) −x, y+1/2, −z; (ii) −x+1, y+1/2, −z+1; (iii) −x+1, y−1/2, −z.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₆O₁₁
M_r	418.39
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	294
a, b, c (Å)	9.2079 (9), 8.5034 (5), 14.3199 (12)
β (°)	100.804 (9)
V (Å³)	1101.35 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.38 × 0.32 × 0.25

Data collection
Diffractometer	Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6393, 2160, 1582
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.147, 1.03
No. of reflections	2160
No. of parameters	268
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.21

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O11ⁱ	0.98	2.47	3.362 (5)	152
C5—H5···O11ⁱ	0.98	2.57	3.443 (6)	149
C11—H11B···O5ⁱⁱ	0.96	2.49	3.293 (7)	141
C16—H16C···O9ⁱⁱⁱ	0.96	2.60	3.441 (7)	147

Symmetry codes: (i) −x, y+1/2, −z; (ii) −x+1, y+1/2, −z+1; (iii) −x+1, y−1/2, −z.

Acknowledgements

The work was supported financially by the National Natural Science Foundation of China (No. 30870553) and the Key International S&T Cooperation Project, China (No. 2010DFA34370).

References

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