{6-[2,5-Bis(chloro­meth­yl)-3,4-dihydroxy­tetra­hydro­furan-2-yl­oxy]-3-chloro-4,5-dihydr­oxy-3,4,5,6-tetra­hydro-2H-pyran-2-yl}methyl acetate dihydrate

Zhang, J.-Y.; Hou, X.-H.; Wu, X.-F.

doi:10.1107/S1600536809053173

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o167

doi:10.1107/S1600536809053173

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{6-[2,5-Bis(chloromethyl)-3,4-dihydroxytetrahydrofuran-2-yloxy]-3-chloro-4,5-dihydroxy-3,4,5,6-tetrahydro-2H-pyran-2-yl}methyl acetate dihydrate

Jing-Yu Zhang,^a ^* Xue-Hui Hou ^b and Xue-Fen Wu ^a

^aSchool of Pharmacy, Henan University of Traditional Chinese Medicine, Zhengzhou 450008, People's Republic of China, and ^bDepartment of Humanities and Basic Sciences, Zhengzhou College of Animal Husbandry Engineering, Zhengzhou 450011, People's Republic of China
^*Correspondence e-mail: jyzhang2004@126.com

(Received 19 November 2009; accepted 10 December 2009; online 16 December 2009)

The title compound, C₁₄H₂₁Cl₃O₉·2H₂O, is a disaccharide constructed from a galactose and a fructose. In the molecular structure, the tetrahydrofuran five-membered ring and tetrahydropyran six-membered ring assume envelope and chair conformations, respectively. An extensive O—H⋯O hydrogen-bonding network occurs in the crystal structure.

Related literature

For the biological importance of sucrose and its derivatives, see: Liu et al. (2004 ); Stutz (1999 ).

Experimental

Crystal data

C₁₄H₂₁Cl₃O₉·2H₂O
M_r = 475.69
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.5824 (8) Å
b = 14.2703 (14) Å
c = 19.507 (2) Å
V = 2110.7 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.49 mm⁻¹
T = 298 K
0.42 × 0.22 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.822, T_max = 0.931
8741 measured reflections
3705 independent reflections
2973 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.081
S = 1.03
3705 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.19 e Å⁻³
Absolute structure: Flack (1983 ), 1569 Friedel pairs
Flack parameter: 0.10 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O10	0.82	1.94	2.716 (3)	158
O4—H4⋯O7ⁱ	0.82	1.88	2.692 (3)	172
O7—H7⋯O3ⁱⁱ	0.82	1.81	2.610 (3)	165
O8—H8⋯O11	0.82	2.08	2.844 (3)	156
O10—H10C⋯O4ⁱⁱⁱ	0.85	1.98	2.820 (3)	171
O10—H10D⋯O11^iv	0.85	2.13	2.972 (3)	171
O11—H11E⋯O6ⁱⁱ	0.85	2.16	3.011 (3)	176
O11—H11F⋯O9^v	0.85	2.05	2.896 (3)	176
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (ii) x-1, y, z; (iii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (iv) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (v) $[-x+{\script{1\over 2}}, -y+1, z+{\script{1\over 2}}]$ .

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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/S1600536809053173/xu2685sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809053173/xu2685Isup2.hkl

checkCIF report

Comment top

Due to its widespread existence in all photosynthetic plants and its biological importance, sucrose and its derivatives are of interest as potentially useful substrates in the chemical and biological fields (Liu et al., 2004; Stutz, 1999). To develop new applications for sucrose and its derivatives, structural modifications of sucrose have been extensively investigated. As a contribution to the sucrose chemistry, we report here the crystal structure of the title compound.

The molecular structure of title compound is shown in Fig.1. Intermolecular hydrogen bonds link molecules in crystal structure into a three-dimensional structure (Table 1).

Related literature top

For the biological importance of sucrose and its derivatives, see: Liu et al. (2004); Stutz (1999).

Experimental top

The reaction was carried out under nitrogen atmosphere. Sucrose (0.50 mol) and thionyl chloride (2.00 mol) were added to a stirred solution of pyridine (500 ml) and stirred at 418 K for 12 h. The solvent was evaporated under vacuum. 50 ml of water was added to the reside and pH was adjusted to 7 with the saturated NaOH-solution. The mixture was washed with toluene (2*30 ml) and concentrated under vacuum to obtain the title compound as a white solid. Colourless crystals suitable for X-ray analysis were obtained by slow evaporation of a ethyl acetate solution over a period of two weeks.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 the compound, with atom labels and 50% probability displacement ellipsoids.

{6-[2,5-Bis(chloromethyl)-3,4-dihydroxytetrahydrofuran-2-yloxy]- 3-chloro-4,5-dihydroxy-3,4,5,6-tetrahydro-2H-pyran-2-yl}methyl acetate dihydrate top

Crystal data top

C₁₄H₂₁Cl₃O₉·2H₂O	F(000) = 992
M_r = 475.69	D_x = 1.497 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3263 reflections
a = 7.5824 (8) Å	θ = 2.5–25.7°
b = 14.2703 (14) Å	µ = 0.49 mm⁻¹
c = 19.507 (2) Å	T = 298 K
V = 2110.7 (4) Å³	Block, colorless
Z = 4	0.42 × 0.22 × 0.15 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3705 independent reflections
Radiation source: fine-focus sealed tube	2973 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→9
T_min = 0.822, T_max = 0.931	k = −16→9
8741 measured reflections	l = −21→23

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) = 0.081	w = 1/[σ²(F_o²) + (0.0283P)² + 0.4654P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
3705 reflections	Δρ_max = 0.23 e Å⁻³
253 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1569 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.10 (6)

Crystal data top

C₁₄H₂₁Cl₃O₉·2H₂O	V = 2110.7 (4) Å³
M_r = 475.69	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.5824 (8) Å	µ = 0.49 mm⁻¹
b = 14.2703 (14) Å	T = 298 K
c = 19.507 (2) Å	0.42 × 0.22 × 0.15 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3705 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2973 reflections with I > 2σ(I)
T_min = 0.822, T_max = 0.931	R_int = 0.042
8741 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.081	Δρ_max = 0.23 e Å⁻³
S = 1.03	Δρ_min = −0.19 e Å⁻³
3705 reflections	Absolute structure: Flack (1983), 1569 Friedel pairs
253 parameters	Absolute structure parameter: 0.10 (6)
0 restraints

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

	x	y	z	U_iso*/U_eq
Cl1	1.02954 (11)	0.51019 (6)	0.41375 (4)	0.0512 (2)
Cl2	0.69677 (15)	0.68921 (6)	0.81804 (4)	0.0696 (3)
Cl3	0.80356 (16)	0.31574 (7)	0.75058 (6)	0.0844 (4)
O1	0.8271 (2)	0.49683 (12)	0.55568 (8)	0.0347 (4)
O2	0.7716 (2)	0.62834 (12)	0.62281 (8)	0.0310 (4)
O3	1.1081 (2)	0.69493 (13)	0.60293 (9)	0.0364 (5)
H3	1.0327	0.7349	0.6101	0.055*
O4	1.1037 (3)	0.70723 (12)	0.45730 (9)	0.0397 (5)
H4	1.0639	0.7447	0.4295	0.060*
O5	0.5109 (3)	0.42018 (15)	0.50144 (11)	0.0549 (6)
O6	0.7424 (2)	0.52803 (11)	0.71868 (9)	0.0329 (4)
O7	0.4430 (3)	0.67403 (16)	0.62983 (11)	0.0534 (6)
H7	0.3350	0.6751	0.6278	0.080*
O8	0.2886 (3)	0.47783 (15)	0.67508 (11)	0.0536 (6)
H8	0.2590	0.4845	0.7152	0.080*
O9	0.3805 (4)	0.35928 (18)	0.41001 (13)	0.0728 (8)
O10	0.9171 (3)	0.85590 (14)	0.60537 (13)	0.0619 (7)
H10C	0.8167	0.8417	0.5890	0.074*
H10D	0.9044	0.9015	0.6329	0.074*
O11	0.0863 (3)	0.51355 (17)	0.79506 (11)	0.0628 (6)
H11E	−0.0125	0.5198	0.7750	0.075*
H11F	0.0905	0.5519	0.8283	0.075*
C1	0.9025 (4)	0.56650 (18)	0.59817 (13)	0.0304 (6)
H1	0.9602	0.5361	0.6373	0.036*
C2	1.0379 (4)	0.62448 (18)	0.55956 (13)	0.0299 (6)
H2	1.1350	0.5825	0.5471	0.036*
C3	0.9628 (4)	0.66439 (18)	0.49342 (13)	0.0309 (6)
H3A	0.8761	0.7127	0.5051	0.037*
C4	0.8711 (4)	0.58870 (19)	0.45181 (13)	0.0339 (7)
H4A	0.8051	0.6191	0.4148	0.041*
C5	0.7409 (4)	0.53505 (18)	0.49644 (14)	0.0346 (6)
H5	0.6492	0.5786	0.5119	0.042*
C6	0.6536 (4)	0.4552 (2)	0.45939 (16)	0.0471 (8)
H6A	0.6081	0.4765	0.4156	0.056*
H6B	0.7385	0.4057	0.4509	0.056*
C7	0.6951 (4)	0.61492 (17)	0.68933 (13)	0.0295 (6)
C8	0.4961 (4)	0.61162 (19)	0.68120 (14)	0.0352 (7)
H8A	0.4398	0.6288	0.7247	0.042*
C9	0.4633 (4)	0.5094 (2)	0.66658 (14)	0.0369 (7)
H9	0.4991	0.4967	0.6192	0.044*
C10	0.5962 (4)	0.46240 (19)	0.71439 (15)	0.0370 (7)
H10	0.5433	0.4546	0.7599	0.044*
C11	0.6622 (5)	0.3694 (2)	0.68905 (17)	0.0497 (8)
H11A	0.7261	0.3782	0.6465	0.060*
H11B	0.5627	0.3285	0.6799	0.060*
C12	0.7704 (5)	0.6936 (2)	0.73225 (13)	0.0437 (8)
H12A	0.7364	0.7532	0.7123	0.052*
H12B	0.8981	0.6899	0.7315	0.052*
C13	0.3859 (5)	0.3717 (2)	0.47033 (19)	0.0516 (9)
C14	0.2524 (5)	0.3352 (3)	0.52023 (19)	0.0766 (12)
H14A	0.3003	0.2821	0.5441	0.115*
H14B	0.1479	0.3166	0.4960	0.115*
H14C	0.2233	0.3834	0.5526	0.115*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0524 (5)	0.0546 (5)	0.0466 (4)	−0.0006 (4)	0.0119 (4)	−0.0130 (4)
Cl2	0.1087 (9)	0.0690 (5)	0.0311 (4)	0.0230 (6)	−0.0028 (5)	−0.0049 (4)
Cl3	0.0934 (9)	0.0619 (6)	0.0980 (8)	0.0202 (6)	−0.0228 (7)	0.0209 (6)
O1	0.0398 (11)	0.0339 (9)	0.0304 (10)	−0.0023 (9)	−0.0014 (9)	0.0024 (8)
O2	0.0281 (10)	0.0377 (10)	0.0273 (10)	0.0053 (9)	0.0027 (8)	0.0068 (8)
O3	0.0258 (10)	0.0402 (11)	0.0431 (11)	0.0001 (9)	−0.0042 (9)	−0.0064 (9)
O4	0.0352 (11)	0.0427 (11)	0.0413 (11)	−0.0018 (10)	0.0055 (10)	0.0128 (10)
O5	0.0577 (15)	0.0651 (14)	0.0419 (12)	−0.0286 (13)	−0.0010 (12)	−0.0018 (11)
O6	0.0326 (11)	0.0340 (10)	0.0321 (10)	−0.0010 (9)	−0.0045 (9)	0.0071 (8)
O7	0.0249 (12)	0.0672 (15)	0.0679 (15)	0.0043 (11)	−0.0037 (10)	0.0382 (12)
O8	0.0330 (12)	0.0719 (15)	0.0560 (13)	−0.0154 (12)	−0.0016 (10)	0.0056 (12)
O9	0.0735 (19)	0.0873 (18)	0.0577 (16)	−0.0277 (15)	−0.0058 (15)	−0.0145 (15)
O10	0.0496 (15)	0.0453 (13)	0.0908 (18)	0.0043 (11)	−0.0205 (14)	−0.0132 (12)
O11	0.0531 (14)	0.0871 (17)	0.0482 (13)	0.0025 (14)	−0.0063 (11)	−0.0002 (13)
C1	0.0294 (15)	0.0322 (14)	0.0295 (15)	0.0043 (13)	−0.0043 (12)	0.0033 (12)
C2	0.0246 (14)	0.0304 (14)	0.0347 (14)	0.0014 (13)	−0.0021 (12)	−0.0005 (12)
C3	0.0260 (15)	0.0334 (14)	0.0333 (14)	−0.0017 (13)	0.0038 (13)	0.0034 (12)
C4	0.0344 (17)	0.0385 (15)	0.0290 (15)	0.0000 (13)	−0.0031 (13)	0.0020 (12)
C5	0.0333 (16)	0.0392 (15)	0.0314 (14)	−0.0043 (13)	−0.0031 (13)	−0.0014 (12)
C6	0.047 (2)	0.0521 (18)	0.0420 (17)	−0.0170 (16)	0.0015 (16)	−0.0037 (15)
C7	0.0314 (16)	0.0309 (14)	0.0263 (14)	0.0012 (13)	−0.0005 (12)	0.0079 (11)
C8	0.0299 (17)	0.0417 (16)	0.0341 (15)	0.0059 (14)	0.0030 (13)	0.0066 (13)
C9	0.0303 (15)	0.0476 (17)	0.0329 (15)	−0.0062 (15)	0.0003 (12)	0.0065 (13)
C10	0.0321 (16)	0.0425 (17)	0.0362 (16)	−0.0065 (14)	0.0006 (14)	0.0095 (14)
C11	0.052 (2)	0.0373 (17)	0.060 (2)	−0.0049 (16)	−0.0078 (17)	0.0065 (16)
C12	0.057 (2)	0.0391 (16)	0.0346 (16)	−0.0028 (16)	−0.0043 (15)	0.0023 (13)
C13	0.053 (2)	0.0424 (18)	0.059 (2)	−0.0080 (17)	−0.0037 (19)	0.0036 (18)
C14	0.072 (3)	0.084 (3)	0.074 (3)	−0.040 (2)	−0.008 (2)	0.019 (2)

Geometric parameters (Å, º) top

Cl1—C4	1.802 (3)	C2—C3	1.521 (3)
Cl2—C12	1.765 (3)	C2—H2	0.9800
Cl3—C11	1.782 (3)	C3—C4	1.519 (4)
O1—C1	1.415 (3)	C3—H3A	0.9800
O1—C5	1.436 (3)	C4—C5	1.523 (4)
O2—C1	1.412 (3)	C4—H4A	0.9800
O2—C7	1.434 (3)	C5—C6	1.503 (4)
O3—C2	1.418 (3)	C5—H5	0.9800
O3—H3	0.8200	C6—H6A	0.9700
O4—C3	1.418 (3)	C6—H6B	0.9700
O4—H4	0.8200	C7—C12	1.512 (4)
O5—C13	1.321 (4)	C7—C8	1.518 (4)
O5—C6	1.447 (4)	C8—C9	1.507 (4)
O6—C7	1.412 (3)	C8—H8A	0.9800
O6—C10	1.454 (3)	C9—C10	1.528 (4)
O7—C8	1.400 (3)	C9—H9	0.9800
O7—H7	0.8200	C10—C11	1.502 (4)
O8—C9	1.409 (3)	C10—H10	0.9800
O8—H8	0.8200	C11—H11A	0.9700
O9—C13	1.191 (4)	C11—H11B	0.9700
O10—H10C	0.8500	C12—H12A	0.9700
O10—H10D	0.8500	C12—H12B	0.9700
O11—H11E	0.8500	C13—C14	1.498 (5)
O11—H11F	0.8500	C14—H14A	0.9600
C1—C2	1.518 (4)	C14—H14B	0.9600
C1—H1	0.9800	C14—H14C	0.9600

C1—O1—C5	112.87 (19)	O6—C7—O2	112.4 (2)
C1—O2—C7	120.57 (18)	O6—C7—C12	109.4 (2)
C2—O3—H3	109.5	O2—C7—C12	104.4 (2)
C3—O4—H4	109.5	O6—C7—C8	105.5 (2)
C13—O5—C6	117.2 (2)	O2—C7—C8	108.2 (2)
C7—O6—C10	110.44 (19)	C12—C7—C8	117.1 (2)
C8—O7—H7	109.5	O7—C8—C9	115.7 (2)
C9—O8—H8	109.5	O7—C8—C7	109.9 (2)
H10C—O10—H10D	108.6	C9—C8—C7	102.3 (2)
H11E—O11—H11F	108.5	O7—C8—H8A	109.5
O2—C1—O1	110.8 (2)	C9—C8—H8A	109.5
O2—C1—C2	107.7 (2)	C7—C8—H8A	109.5
O1—C1—C2	111.4 (2)	O8—C9—C8	116.2 (2)
O2—C1—H1	109.0	O8—C9—C10	114.1 (2)
O1—C1—H1	109.0	C8—C9—C10	101.6 (2)
C2—C1—H1	109.0	O8—C9—H9	108.2
O3—C2—C1	110.1 (2)	C8—C9—H9	108.2
O3—C2—C3	112.4 (2)	C10—C9—H9	108.2
C1—C2—C3	111.8 (2)	O6—C10—C11	109.5 (2)
O3—C2—H2	107.4	O6—C10—C9	104.8 (2)
C1—C2—H2	107.4	C11—C10—C9	114.0 (2)
C3—C2—H2	107.4	O6—C10—H10	109.5
O4—C3—C4	112.7 (2)	C11—C10—H10	109.5
O4—C3—C2	107.5 (2)	C9—C10—H10	109.5
C4—C3—C2	111.0 (2)	C10—C11—Cl3	111.0 (2)
O4—C3—H3A	108.5	C10—C11—H11A	109.4
C4—C3—H3A	108.5	Cl3—C11—H11A	109.4
C2—C3—H3A	108.5	C10—C11—H11B	109.4
C3—C4—C5	110.4 (2)	Cl3—C11—H11B	109.4
C3—C4—Cl1	110.9 (2)	H11A—C11—H11B	108.0
C5—C4—Cl1	110.81 (19)	C7—C12—Cl2	112.3 (2)
C3—C4—H4A	108.2	C7—C12—H12A	109.1
C5—C4—H4A	108.2	Cl2—C12—H12A	109.1
Cl1—C4—H4A	108.2	C7—C12—H12B	109.1
O1—C5—C6	107.4 (2)	Cl2—C12—H12B	109.1
O1—C5—C4	110.8 (2)	H12A—C12—H12B	107.9
C6—C5—C4	113.1 (2)	O9—C13—O5	123.8 (3)
O1—C5—H5	108.5	O9—C13—C14	124.6 (3)
C6—C5—H5	108.5	O5—C13—C14	111.6 (3)
C4—C5—H5	108.5	C13—C14—H14A	109.5
O5—C6—C5	108.6 (2)	C13—C14—H14B	109.5
O5—C6—H6A	110.0	H14A—C14—H14B	109.5
C5—C6—H6A	110.0	C13—C14—H14C	109.5
O5—C6—H6B	110.0	H14A—C14—H14C	109.5
C5—C6—H6B	110.0	H14B—C14—H14C	109.5
H6A—C6—H6B	108.4

C7—O2—C1—O1	96.6 (2)	C10—O6—C7—C8	13.7 (3)
C7—O2—C1—C2	−141.3 (2)	C1—O2—C7—O6	−10.3 (3)
C5—O1—C1—O2	60.7 (3)	C1—O2—C7—C12	108.2 (3)
C5—O1—C1—C2	−59.1 (3)	C1—O2—C7—C8	−126.4 (2)
O2—C1—C2—O3	57.0 (3)	O6—C7—C8—O7	−156.5 (2)
O1—C1—C2—O3	178.7 (2)	O2—C7—C8—O7	−36.0 (3)
O2—C1—C2—C3	−68.7 (3)	C12—C7—C8—O7	81.6 (3)
O1—C1—C2—C3	52.9 (3)	O6—C7—C8—C9	−33.1 (3)
O3—C2—C3—O4	62.5 (3)	O2—C7—C8—C9	87.4 (2)
C1—C2—C3—O4	−173.0 (2)	C12—C7—C8—C9	−155.0 (2)
O3—C2—C3—C4	−173.8 (2)	O7—C8—C9—O8	−77.6 (3)
C1—C2—C3—C4	−49.3 (3)	C7—C8—C9—O8	163.0 (2)
O4—C3—C4—C5	171.3 (2)	O7—C8—C9—C10	158.0 (2)
C2—C3—C4—C5	50.6 (3)	C7—C8—C9—C10	38.6 (3)
O4—C3—C4—Cl1	48.1 (3)	C7—O6—C10—C11	133.7 (2)
C2—C3—C4—Cl1	−72.6 (2)	C7—O6—C10—C9	11.0 (3)
C1—O1—C5—C6	−175.1 (2)	O8—C9—C10—O6	−156.9 (2)
C1—O1—C5—C4	60.9 (3)	C8—C9—C10—O6	−31.1 (3)
C3—C4—C5—O1	−55.8 (3)	O8—C9—C10—C11	83.4 (3)
Cl1—C4—C5—O1	67.5 (2)	C8—C9—C10—C11	−150.8 (2)
C3—C4—C5—C6	−176.5 (2)	O6—C10—C11—Cl3	67.2 (3)
Cl1—C4—C5—C6	−53.2 (3)	C9—C10—C11—Cl3	−175.7 (2)
C13—O5—C6—C5	159.2 (3)	O6—C7—C12—Cl2	−58.1 (3)
O1—C5—C6—O5	67.8 (3)	O2—C7—C12—Cl2	−178.66 (18)
C4—C5—C6—O5	−169.6 (2)	C8—C7—C12—Cl2	61.8 (3)
C10—O6—C7—O2	−104.0 (2)	C6—O5—C13—O9	−3.6 (5)
C10—O6—C7—C12	140.5 (2)	C6—O5—C13—C14	176.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O10	0.82	1.94	2.716 (3)	158
O4—H4···O7ⁱ	0.82	1.88	2.692 (3)	172
O7—H7···O3ⁱⁱ	0.82	1.81	2.610 (3)	165
O8—H8···O11	0.82	2.08	2.844 (3)	156
O10—H10C···O4ⁱⁱⁱ	0.85	1.98	2.820 (3)	171
O10—H10D···O11^iv	0.85	2.13	2.972 (3)	171
O11—H11E···O6ⁱⁱ	0.85	2.16	3.011 (3)	176
O11—H11F···O9^v	0.85	2.05	2.896 (3)	176

Symmetry codes: (i) x+1/2, −y+3/2, −z+1; (ii) x−1, y, z; (iii) x−1/2, −y+3/2, −z+1; (iv) −x+1, y+1/2, −z+3/2; (v) −x+1/2, −y+1, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₂₁Cl₃O₉·2H₂O
M_r	475.69
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	7.5824 (8), 14.2703 (14), 19.507 (2)
V (Å³)	2110.7 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.49
Crystal size (mm)	0.42 × 0.22 × 0.15

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.822, 0.931
No. of measured, independent and observed [I > 2σ(I)] reflections	8741, 3705, 2973
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.081, 1.03
No. of reflections	3705
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.19
Absolute structure	Flack (1983), 1569 Friedel pairs
Absolute structure parameter	0.10 (6)

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O10	0.82	1.94	2.716 (3)	157.9
O4—H4···O7ⁱ	0.82	1.88	2.692 (3)	172.3
O7—H7···O3ⁱⁱ	0.82	1.81	2.610 (3)	164.8
O8—H8···O11	0.82	2.08	2.844 (3)	155.8
O10—H10C···O4ⁱⁱⁱ	0.85	1.98	2.820 (3)	170.8
O10—H10D···O11^iv	0.85	2.13	2.972 (3)	171.4
O11—H11E···O6ⁱⁱ	0.85	2.16	3.011 (3)	175.9
O11—H11F···O9^v	0.85	2.05	2.896 (3)	175.6

Symmetry codes: (i) x+1/2, −y+3/2, −z+1; (ii) x−1, y, z; (iii) x−1/2, −y+3/2, −z+1; (iv) −x+1, y+1/2, −z+3/2; (v) −x+1/2, −y+1, z+1/2.

Acknowledgements

We gratefully acknowledge financial support from the National Natural Science Foundation of China (No. 20572103).

References

Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Liu, F.-W., Liu, H.-M., Yu, K. & Zhang, J.-Y. (2004). Carbohydr. Res. 339, 2651–2656. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Stutz, A. E. (1999). Iminosugars as Glycosidase Inhibitors: Nojirimycin and Beyond. Weinheim: Wiley–VCH. Google Scholar

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Volume 66| Part 1| January 2010| Page o167

doi:10.1107/S1600536809053173

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

{6-[2,5-Bis(chloro­meth­yl)-3,4-di­hydroxy­tetra­hydro­furan-2-yl­­oxy]-3-chloro-4,5-dihydr­­oxy-3,4,5,6-tetra­hydro-2H-pyran-2-yl}methyl acetate dihydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

{6-[2,5-Bis(chloromethyl)-3,4-dihydroxytetrahydrofuran-2-yloxy]-3-chloro-4,5-dihydroxy-3,4,5,6-tetrahydro-2H-pyran-2-yl}methyl acetate dihydrate