{6-[2,5-Bis(chloro-meth-yl)-3,4-dihydroxy-tetra-hydro-furan-2-yl-oxy]-3-chloro-4,5-dihydr-oxy-3,4,5,6-tetra-hydro-2H-pyran-2-yl}methyl acetate dihydrate.

The title compound, C(14)H(21)Cl(3)O(9)·2H(2)O, is a disaccharide constructed from a galactose and a fructose. In the mol-ecular structure, the tetra-hydro-furan five-membered ring and tetra-hydro-pyran 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 = 475.69

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.081

S = 1.03

3705 reflections

253 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: Flack (1983 ▶), 1569 Friedel pairs

Flack parameter: 0.10 (6)

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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809053173/xu2685sup1.cif

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

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

C14H21Cl3O9·2H2O	F(000) = 992
Mr = 475.69	Dx = 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

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

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(Fo2) + (0.0283P)2 + 0.4654P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
3705 reflections	Δρmax = 0.23 e Å−3
253 parameters	Δρmin = −0.19 e Å−3
0 restraints	Absolute structure: Flack (1983), 1569 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.10 (6)

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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···O11iv	0.85	2.13	2.972 (3)	171
O11—H11E···O6ii	0.85	2.16	3.011 (3)	176
O11—H11F···O9v	0.85	2.05	2.896 (3)	176

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⋯O11iv	0.85	2.13	2.972 (3)	171
O11—H11E⋯O6ii	0.85	2.16	3.011 (3)	176
O11—H11F⋯O9v	0.85	2.05	2.896 (3)	176

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .