2,3,4-Tri-O-acetyl-β-d-xylosyl 2,4-dichloro­phenoxy­acetate

Wang, X.; Li, X.; Yin, Y.; Pang, Y.; Yang, Y.

doi:10.1107/S1600536808005837

organic compounds

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ISSN: 2056-9890

Volume 64| Part 4| April 2008| Page o669

doi:10.1107/S1600536808005837

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2,3,4-Tri-O-acetyl-β-D-xylosyl 2,4-dichlorophenoxyacetate

Xiaoming Wang,^a Xinyuan Li,^a Yale Yin,^a Yanjun Pang ^a and Yonghua Yang ^a ^*

^aState Key Laboratory of Pharmaceutical Biotechnology, School of Life Sciences, nanjing University, Hankou Road, Nanjing 210093, People's Republic of China
^*Correspondence e-mail: yangyh@nju.edu.cn

(Received 11 January 2008; accepted 2 March 2008; online 5 March 2008)

In the title compound, C₁₉H₂₀Cl₂O₁₀, the hexopyranosyl ring adopts a chair conformation. The four substituents are in equatorial positions. The molecules arelinked via C—H⋯O contacts along the a axis.

Related literature

For related literature, see: Hamner et al. (1946 ); Chandrasekhar & Pattabhi (1977 ); Dalton (2004 ); Tsorteki et al. (2004 ); Yang et al. (2004 ).

Experimental

Crystal data

C₁₉H₂₀Cl₂O₁₀
M_r = 479.25
Monoclinic, P 2₁
a = 5.6601 (8) Å
b = 23.129 (3) Å
c = 8.7456 (13) Å
β = 104.281 (2)°
V = 1109.5 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 293 (2) K
0.45 × 0.23 × 0.21 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: none
5656 measured reflections
3337 independent reflections
3044 reflections with I > 2σ(I)
R_int = 0.089

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.121
S = 1.03
3337 reflections
284 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.31 e Å⁻³
Absolute structure: Flack (1983 ), 1325 Friedel pairs
Flack parameter: 0.04 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O6ⁱ	0.93	2.41	3.322 (6)	168
C9—H9⋯O10ⁱ	0.98	2.54	3.381 (4)	144
C11—H11⋯O10ⁱ	0.98	2.44	3.296 (4)	146
Symmetry code: (i) x-1, y, z.

Data collection: SMART (Bruker, 2003 ); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808005837/si2071sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808005837/si2071Isup2.hkl

checkCIF report

Comment top

The plant growth regulator 2,4-dichlorophenoxyacetic acid cocrystallized as a guest molecule in Heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin (Tsorteki et al., 2004), and it plays an important role in graining and controlling weeds (Hamner et al., 1946). However, problems such as toxic residues and environmental pollution were protruded increasingly by using amounts of herbicides during the past decades (Dalton, 2004). In order to search for a new herbicide with high efficiency and low toxicity, we obtained the title compound. All bond lengths and angles in the title molecule show normal values. The hexopyranosyl ring adopts a chair conformation (Fig. 1). The three acetyl groups are individually planar and occupy equatorial positions (Yang et al., 2004). The 2,4-dichlorophenoxyacetic acid group shows a similar geometry in 2-Chlorophenoxyacetic acid (Chandrasekhar & Pattabhi, 1977), and it is twisted at the bond of O3—C8—C7—O1, with the torsion angle of 4.3°. The title molecules are linked via intermolecular hydrogen bonding C—H···O contacts along the a axis by translation (Table 1).

Related literature top

For related literature, see: Hamner et al. (1946); Chandrasekhar & Pattabhi (1977); Dalton (2004); Tsorteki et al. (2004); Yang et al. (2004).

Experimental top

The title compound was prepared from α-D-1-bromo-2,3,4-tri-O- acetyl-xylosyl with 2,4-dichlorophenoxyacetic acid in aq NaOH at the benzyltriethylammonium chloride and 4-dimethylaminopyridine in present. Fine block colourless crystals for single-crystal X-ray diffraction were obtained by slow evaporation of an ethyl acetate at room temperature.

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (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 the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.

2,3,4-Tri-O-acetyl-β-D-xylosyl 2,4-dichlorophenoxyacetate top

Crystal data top

C₁₉H₂₀Cl₂O₁₀	F(000) = 496
M_r = 479.25	D_x = 1.435 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 90 reflections
a = 5.6601 (8) Å	θ = 2.4–25.0°
b = 23.129 (3) Å	µ = 0.35 mm⁻¹
c = 8.7456 (13) Å	T = 293 K
β = 104.281 (2)°	Block, colourless
V = 1109.5 (3) Å³	0.45 × 0.23 × 0.21 mm
Z = 2

Data collection top

Bruker SMART APEX CCD diffractometer	3044 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.089
Graphite monochromator	θ_max = 25.0°, θ_min = 2.4°
Detector resolution: 9.00cm pixels mm^-1	h = −6→5
ω and ϕ scans	k = −27→15
5656 measured reflections	l = −9→10
3337 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)] = 0.046	H-atom parameters constrained
wR(F²) = 0.121	w = 1/[σ²(F_o²) + (0.0733P)² + 0.2029P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3337 reflections	Δρ_max = 0.29 e Å⁻³
284 parameters	Δρ_min = −0.31 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1325 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (8)

Crystal data top

C₁₉H₂₀Cl₂O₁₀	V = 1109.5 (3) Å³
M_r = 479.25	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 5.6601 (8) Å	µ = 0.35 mm⁻¹
b = 23.129 (3) Å	T = 293 K
c = 8.7456 (13) Å	0.45 × 0.23 × 0.21 mm
β = 104.281 (2)°

Data collection top

Bruker SMART APEX CCD diffractometer	3044 reflections with I > 2σ(I)
5656 measured reflections	R_int = 0.089
3337 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	H-atom parameters constrained
wR(F²) = 0.121	Δρ_max = 0.29 e Å⁻³
S = 1.04	Δρ_min = −0.31 e Å⁻³
3337 reflections	Absolute structure: Flack (1983), 1325 Friedel pairs
284 parameters	Absolute structure parameter: 0.04 (8)
1 restraint

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
Cl1	0.39611 (18)	0.41178 (5)	0.40852 (13)	0.0708 (3)
Cl2	−0.4306 (3)	0.37317 (8)	−0.0324 (2)	0.1303 (7)
O1	0.2663 (5)	0.31057 (11)	0.5567 (3)	0.0593 (6)
O2	0.1992 (6)	0.16524 (12)	0.6787 (3)	0.0662 (7)
O3	0.3421 (4)	0.20235 (10)	0.4807 (3)	0.0492 (5)
O4	0.6349 (4)	0.13402 (10)	0.5269 (3)	0.0501 (6)
O5	0.1431 (4)	0.15293 (10)	0.1744 (3)	0.0452 (5)
O6	0.2612 (5)	0.22405 (14)	0.0364 (4)	0.0748 (9)
O7	0.4821 (4)	0.08031 (10)	0.0669 (2)	0.0478 (5)
O8	0.1649 (6)	0.01975 (16)	0.0038 (4)	0.0854 (10)
O9	0.7485 (4)	0.00745 (10)	0.2985 (2)	0.0451 (5)
O10	1.1379 (4)	0.01306 (11)	0.4309 (3)	0.0552 (6)
C1	−0.0205 (8)	0.38597 (19)	0.1966 (5)	0.0648 (10)
H1	0.0105	0.4181	0.1406	0.078*
C2	−0.2255 (8)	0.3534 (2)	0.1430 (5)	0.0733 (11)
C3	−0.2759 (8)	0.30616 (19)	0.2235 (6)	0.0724 (11)
H3	−0.4165	0.2846	0.1841	0.087*
C4	−0.1159 (7)	0.29073 (17)	0.3640 (5)	0.0601 (9)
H4	−0.1510	0.2592	0.4207	0.072*
C5	0.0968 (6)	0.32194 (15)	0.4211 (4)	0.0502 (8)
C6	0.1387 (6)	0.36984 (16)	0.3357 (4)	0.0520 (8)
C7	0.2153 (9)	0.26725 (17)	0.6570 (4)	0.0632 (10)
H7A	0.0481	0.2720	0.6641	0.076*
H7B	0.3196	0.2734	0.7617	0.076*
C8	0.2479 (6)	0.20569 (15)	0.6091 (4)	0.0470 (7)
C9	0.3960 (5)	0.14523 (14)	0.4394 (3)	0.0406 (6)
H9	0.2811	0.1173	0.4647	0.049*
C10	0.3903 (5)	0.14345 (14)	0.2641 (3)	0.0396 (6)
H10	0.5002	0.1726	0.2382	0.048*
C11	0.4660 (5)	0.08292 (14)	0.2273 (3)	0.0383 (6)
H11	0.3442	0.0550	0.2435	0.046*
C12	0.7106 (5)	0.06757 (13)	0.3323 (4)	0.0407 (6)
H12	0.8380	0.0917	0.3066	0.049*
C13	0.7069 (6)	0.07587 (15)	0.5044 (4)	0.0462 (7)
H13A	0.5931	0.0489	0.5323	0.055*
H13B	0.8676	0.0684	0.5719	0.055*
C14	0.1046 (6)	0.19246 (16)	0.0576 (4)	0.0479 (8)
C15	−0.1479 (7)	0.1900 (2)	−0.0418 (5)	0.0628 (10)
H15A	−0.2249	0.2269	−0.0404	0.094*
H15B	−0.2378	0.1610	−0.0013	0.094*
H15C	−0.1450	0.1804	−0.1481	0.094*
C16	0.3333 (7)	0.04317 (17)	−0.0295 (4)	0.0543 (9)
C17	0.4131 (10)	0.0352 (2)	−0.1786 (5)	0.0802 (14)
H17A	0.5523	0.0101	−0.1593	0.120*
H17B	0.4557	0.0721	−0.2148	0.120*
H17C	0.2827	0.0184	−0.2575	0.120*
C18	0.9736 (5)	−0.01395 (15)	0.3484 (4)	0.0439 (7)
C19	0.9926 (7)	−0.07338 (17)	0.2889 (5)	0.0620 (9)
H19A	1.0063	−0.0716	0.1818	0.093*
H19B	0.8497	−0.0950	0.2934	0.093*
H19C	1.1343	−0.0920	0.3531	0.093*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0728 (6)	0.0576 (6)	0.0782 (6)	−0.0171 (5)	0.0114 (5)	−0.0004 (5)
Cl2	0.1225 (12)	0.1201 (14)	0.1079 (10)	−0.0217 (10)	−0.0481 (9)	0.0335 (10)
O1	0.0780 (16)	0.0361 (13)	0.0569 (14)	0.0026 (12)	0.0038 (12)	−0.0004 (11)
O2	0.100 (2)	0.0457 (16)	0.0624 (16)	0.0022 (14)	0.0379 (14)	0.0033 (12)
O3	0.0682 (14)	0.0353 (13)	0.0468 (12)	0.0000 (10)	0.0191 (10)	−0.0025 (10)
O4	0.0557 (13)	0.0461 (15)	0.0444 (12)	0.0009 (10)	0.0044 (10)	−0.0115 (10)
O5	0.0425 (11)	0.0481 (14)	0.0462 (12)	−0.0016 (9)	0.0130 (9)	0.0082 (10)
O6	0.0692 (16)	0.076 (2)	0.0702 (17)	−0.0201 (15)	−0.0009 (13)	0.0305 (15)
O7	0.0600 (13)	0.0497 (14)	0.0362 (10)	−0.0045 (11)	0.0170 (9)	−0.0007 (10)
O8	0.090 (2)	0.091 (3)	0.0718 (19)	−0.0339 (19)	0.0142 (16)	−0.0312 (17)
O9	0.0458 (11)	0.0385 (13)	0.0508 (12)	−0.0028 (9)	0.0114 (9)	−0.0053 (10)
O10	0.0480 (12)	0.0565 (16)	0.0585 (14)	−0.0034 (11)	0.0084 (10)	−0.0008 (12)
C1	0.075 (2)	0.057 (2)	0.058 (2)	−0.0028 (19)	0.0095 (17)	0.0090 (18)
C2	0.070 (2)	0.067 (3)	0.071 (2)	0.001 (2)	−0.0058 (19)	0.006 (2)
C3	0.065 (2)	0.050 (2)	0.095 (3)	−0.0128 (18)	0.003 (2)	−0.003 (2)
C4	0.068 (2)	0.037 (2)	0.074 (2)	−0.0035 (16)	0.0142 (18)	0.0021 (17)
C5	0.0619 (19)	0.0340 (18)	0.0543 (18)	0.0064 (15)	0.0134 (15)	−0.0033 (14)
C6	0.0598 (18)	0.0414 (19)	0.0548 (18)	0.0017 (15)	0.0142 (15)	−0.0048 (15)
C7	0.097 (3)	0.041 (2)	0.052 (2)	0.0103 (19)	0.0190 (19)	−0.0014 (17)
C8	0.0599 (18)	0.0381 (19)	0.0414 (15)	0.0056 (14)	0.0095 (14)	0.0016 (14)
C9	0.0506 (16)	0.0316 (16)	0.0395 (15)	−0.0021 (13)	0.0112 (12)	−0.0031 (12)
C10	0.0399 (14)	0.0401 (17)	0.0389 (14)	−0.0072 (12)	0.0099 (11)	0.0027 (13)
C11	0.0443 (14)	0.0404 (17)	0.0331 (13)	−0.0098 (12)	0.0150 (11)	−0.0017 (12)
C12	0.0418 (15)	0.0334 (17)	0.0477 (16)	−0.0036 (13)	0.0125 (12)	−0.0020 (13)
C13	0.0502 (16)	0.0423 (19)	0.0442 (16)	0.0044 (14)	0.0081 (13)	−0.0024 (14)
C14	0.0517 (17)	0.051 (2)	0.0423 (16)	−0.0055 (15)	0.0146 (13)	−0.0017 (14)
C15	0.0564 (19)	0.073 (3)	0.058 (2)	0.0036 (18)	0.0110 (16)	0.0126 (19)
C16	0.069 (2)	0.046 (2)	0.0420 (17)	0.0046 (17)	0.0039 (16)	−0.0052 (15)
C17	0.132 (4)	0.065 (3)	0.044 (2)	0.019 (3)	0.023 (2)	−0.0076 (19)
C18	0.0437 (17)	0.0473 (19)	0.0421 (16)	−0.0012 (14)	0.0136 (13)	0.0055 (13)
C19	0.063 (2)	0.051 (2)	0.071 (2)	0.0030 (17)	0.0147 (17)	−0.0049 (18)

Geometric parameters (Å, º) top

Cl1—C6	1.735 (4)	C5—C6	1.389 (5)
Cl2—C2	1.740 (4)	C7—C8	1.508 (5)
O1—C5	1.355 (4)	C7—H7A	0.9700
O1—C7	1.407 (5)	C7—H7B	0.9700
O2—C8	1.185 (4)	C9—C10	1.526 (4)
O3—C8	1.359 (4)	C9—H9	0.9800
O3—C9	1.422 (4)	C10—C11	1.521 (4)
O4—C9	1.404 (4)	C10—H10	0.9800
O4—C13	1.433 (4)	C11—C12	1.503 (4)
O5—C14	1.347 (4)	C11—H11	0.9800
O5—C10	1.442 (4)	C12—C13	1.523 (4)
O6—C14	1.198 (4)	C12—H12	0.9800
O7—C16	1.344 (4)	C13—H13A	0.9700
O7—C11	1.429 (3)	C13—H13B	0.9700
O8—C16	1.193 (5)	C14—C15	1.479 (5)
O9—C18	1.336 (4)	C15—H15A	0.9600
O9—C12	1.448 (4)	C15—H15B	0.9600
O10—C18	1.202 (4)	C15—H15C	0.9600
C1—C2	1.366 (6)	C16—C17	1.493 (5)
C1—C6	1.375 (5)	C17—H17A	0.9600
C1—H1	0.9300	C17—H17B	0.9600
C2—C3	1.367 (6)	C17—H17C	0.9600
C3—C4	1.381 (6)	C18—C19	1.483 (5)
C3—H3	0.9300	C19—H19A	0.9600
C4—C5	1.387 (5)	C19—H19B	0.9600
C4—H4	0.9300	C19—H19C	0.9600

C5—O1—C7	118.3 (3)	O7—C11—C12	108.5 (2)
C8—O3—C9	114.5 (2)	O7—C11—C10	109.6 (2)
C9—O4—C13	111.5 (2)	C12—C11—C10	110.7 (2)
C14—O5—C10	118.0 (2)	O7—C11—H11	109.3
C16—O7—C11	117.4 (3)	C12—C11—H11	109.3
C18—O9—C12	117.8 (2)	C10—C11—H11	109.3
C2—C1—C6	118.0 (4)	O9—C12—C11	105.2 (2)
C2—C1—H1	121.0	O9—C12—C13	111.2 (2)
C6—C1—H1	121.0	C11—C12—C13	109.8 (2)
C1—C2—C3	122.1 (4)	O9—C12—H12	110.2
C1—C2—Cl2	118.9 (4)	C11—C12—H12	110.2
C3—C2—Cl2	119.1 (3)	C13—C12—H12	110.2
C2—C3—C4	119.4 (4)	O4—C13—C12	109.1 (3)
C2—C3—H3	120.3	O4—C13—H13A	109.9
C4—C3—H3	120.3	C12—C13—H13A	109.9
C3—C4—C5	120.4 (4)	O4—C13—H13B	109.9
C3—C4—H4	119.8	C12—C13—H13B	109.9
C5—C4—H4	119.8	H13A—C13—H13B	108.3
O1—C5—C4	125.3 (3)	O6—C14—O5	122.9 (3)
O1—C5—C6	116.6 (3)	O6—C14—C15	125.2 (3)
C4—C5—C6	118.0 (3)	O5—C14—C15	111.8 (3)
C1—C6—C5	122.1 (3)	C14—C15—H15A	109.5
C1—C6—Cl1	118.7 (3)	C14—C15—H15B	109.5
C5—C6—Cl1	119.2 (3)	H15A—C15—H15B	109.5
O1—C7—C8	116.2 (3)	C14—C15—H15C	109.5
O1—C7—H7A	108.2	H15A—C15—H15C	109.5
C8—C7—H7A	108.2	H15B—C15—H15C	109.5
O1—C7—H7B	108.2	O8—C16—O7	123.5 (3)
C8—C7—H7B	108.2	O8—C16—C17	126.1 (4)
H7A—C7—H7B	107.4	O7—C16—C17	110.4 (4)
O2—C8—O3	124.6 (3)	C16—C17—H17A	109.5
O2—C8—C7	122.9 (3)	C16—C17—H17B	109.5
O3—C8—C7	112.5 (3)	H17A—C17—H17B	109.5
O4—C9—O3	105.7 (2)	C16—C17—H17C	109.5
O4—C9—C10	108.8 (2)	H17A—C17—H17C	109.5
O3—C9—C10	109.1 (2)	H17B—C17—H17C	109.5
O4—C9—H9	111.0	O10—C18—O9	122.5 (3)
O3—C9—H9	111.0	O10—C18—C19	125.5 (3)
C10—C9—H9	111.0	O9—C18—C19	112.0 (3)
O5—C10—C11	108.1 (2)	C18—C19—H19A	109.5
O5—C10—C9	108.6 (2)	C18—C19—H19B	109.5
C11—C10—C9	107.4 (2)	H19A—C19—H19B	109.5
O5—C10—H10	110.8	C18—C19—H19C	109.5
C11—C10—H10	110.8	H19A—C19—H19C	109.5
C9—C10—H10	110.8	H19B—C19—H19C	109.5

C6—C1—C2—C3	0.4 (7)	O4—C9—C10—O5	178.0 (2)
C6—C1—C2—Cl2	179.7 (3)	O3—C9—C10—O5	−67.1 (3)
C1—C2—C3—C4	0.3 (7)	O4—C9—C10—C11	61.2 (3)
Cl2—C2—C3—C4	−179.0 (4)	O3—C9—C10—C11	176.1 (2)
C2—C3—C4—C5	−1.6 (7)	C16—O7—C11—C12	120.4 (3)
C7—O1—C5—C4	−6.4 (5)	C16—O7—C11—C10	−118.6 (3)
C7—O1—C5—C6	171.7 (3)	O5—C10—C11—O7	67.4 (3)
C3—C4—C5—O1	−179.8 (4)	C9—C10—C11—O7	−175.5 (2)
C3—C4—C5—C6	2.1 (5)	O5—C10—C11—C12	−172.9 (2)
C2—C1—C6—C5	0.2 (6)	C9—C10—C11—C12	−55.9 (3)
C2—C1—C6—Cl1	−178.3 (3)	C18—O9—C12—C11	165.2 (2)
O1—C5—C6—C1	−179.7 (3)	C18—O9—C12—C13	−76.0 (3)
C4—C5—C6—C1	−1.4 (5)	O7—C11—C12—O9	−66.0 (3)
O1—C5—C6—Cl1	−1.2 (4)	C10—C11—C12—O9	173.7 (2)
C4—C5—C6—Cl1	177.0 (3)	O7—C11—C12—C13	174.3 (2)
C5—O1—C7—C8	78.3 (4)	C10—C11—C12—C13	54.0 (3)
C9—O3—C8—O2	−4.1 (5)	C9—O4—C13—C12	63.7 (3)
C9—O3—C8—C7	174.8 (3)	O9—C12—C13—O4	−171.9 (2)
O1—C7—C8—O2	−176.0 (4)	C11—C12—C13—O4	−55.8 (3)
O1—C7—C8—O3	5.0 (5)	C10—O5—C14—O6	−8.1 (5)
C13—O4—C9—O3	176.0 (2)	C10—O5—C14—C15	169.6 (3)
C13—O4—C9—C10	−66.9 (3)	C11—O7—C16—O8	12.6 (5)
C8—O3—C9—O4	−87.9 (3)	C11—O7—C16—C17	−166.3 (3)
C8—O3—C9—C10	155.2 (3)	C12—O9—C18—O10	6.7 (4)
C14—O5—C10—C11	−112.4 (3)	C12—O9—C18—C19	−172.9 (3)
C14—O5—C10—C9	131.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O6ⁱ	0.93	2.41	3.322 (6)	168
C9—H9···O10ⁱ	0.98	2.54	3.381 (4)	144
C11—H11···O10ⁱ	0.98	2.44	3.296 (4)	146

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₀Cl₂O₁₀
M_r	479.25
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	5.6601 (8), 23.129 (3), 8.7456 (13)
β (°)	104.281 (2)
V (Å³)	1109.5 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.45 × 0.23 × 0.21

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5656, 3337, 3044
R_int	0.089
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.121, 1.04
No. of reflections	3337
No. of parameters	284
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.31
Absolute structure	Flack (1983), 1325 Friedel pairs
Absolute structure parameter	0.04 (8)

Computer programs: SMART (Bruker, 2003), SAINT-Plus (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O6ⁱ	0.93	2.41	3.322 (6)	168
C9—H9···O10ⁱ	0.98	2.54	3.381 (4)	144
C11—H11···O10ⁱ	0.98	2.44	3.296 (4)	146

Symmetry code: (i) x−1, y, z.

Acknowledgements

We are grateful to the National Natural Science Foundation of China (No. 30701041), the Postdoctoral Science Foundation of China (No. 20060400917) and Jiangsu Postdoctoral Science Foundation of China (No. 0602002B).

References

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