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

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ISSN: 2056-9890

{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

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[Liu, F.-W., Liu, H.-M., Yu, K. & Zhang, J.-Y. (2004). Carbohydr. Res. 339, 2651-2656.]); Stutz (1999[Stutz, A. E. (1999). Iminosugars as Glycosidase Inhibitors: Nojirimycin and Beyond. Weinheim: Wiley-VCH.]).

[Scheme 1]

Experimental

Crystal data
  • C14H21Cl3O9·2H2O

  • Mr = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.822, Tmax = 0.931

  • 8741 measured reflections

  • 3705 independent reflections

  • 2973 reflections with I > 2σ(I)

  • Rint = 0.042

Refinement
  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 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[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1569 Friedel pairs

  • Flack parameter: 0.10 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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) [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[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


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.

Refinement top

H atoms were positioned geometrically with O—H = 0.82 (hydroxy), 0.85 (water) and C—H = 0.96 (methyl), 0.97 (methylene) and 0.98 Å (methine), and constrained to ride on their parent atoms with Uiso(H) = xUeq (C), where x = 1.5 for methyl and hydroxyl H atoms and x = 1.2 for the others.

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
[Figure 1] 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
C14H21Cl3O9·2H2OF(000) = 992
Mr = 475.69Dx = 1.497 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 3263 reflections
a = 7.5824 (8) Åθ = 2.5–25.7°
b = 14.2703 (14) ŵ = 0.49 mm1
c = 19.507 (2) ÅT = 298 K
V = 2110.7 (4) Å3Block, colorless
Z = 40.42 × 0.22 × 0.15 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
3705 independent reflections
Radiation source: fine-focus sealed tube2973 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
ϕ and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 89
Tmin = 0.822, Tmax = 0.931k = 169
8741 measured reflectionsl = 2123
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H-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 reflectionsΔρmax = 0.23 e Å3
253 parametersΔρmin = 0.19 e Å3
0 restraintsAbsolute structure: Flack (1983), 1569 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.10 (6)
Crystal data top
C14H21Cl3O9·2H2OV = 2110.7 (4) Å3
Mr = 475.69Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.5824 (8) ŵ = 0.49 mm1
b = 14.2703 (14) ÅT = 298 K
c = 19.507 (2) Å0.42 × 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)
Tmin = 0.822, Tmax = 0.931Rint = 0.042
8741 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.081Δρmax = 0.23 e Å3
S = 1.03Δρmin = 0.19 e Å3
3705 reflectionsAbsolute structure: Flack (1983), 1569 Friedel pairs
253 parametersAbsolute structure parameter: 0.10 (6)
0 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl11.02954 (11)0.51019 (6)0.41375 (4)0.0512 (2)
Cl20.69677 (15)0.68921 (6)0.81804 (4)0.0696 (3)
Cl30.80356 (16)0.31574 (7)0.75058 (6)0.0844 (4)
O10.8271 (2)0.49683 (12)0.55568 (8)0.0347 (4)
O20.7716 (2)0.62834 (12)0.62281 (8)0.0310 (4)
O31.1081 (2)0.69493 (13)0.60293 (9)0.0364 (5)
H31.03270.73490.61010.055*
O41.1037 (3)0.70723 (12)0.45730 (9)0.0397 (5)
H41.06390.74470.42950.060*
O50.5109 (3)0.42018 (15)0.50144 (11)0.0549 (6)
O60.7424 (2)0.52803 (11)0.71868 (9)0.0329 (4)
O70.4430 (3)0.67403 (16)0.62983 (11)0.0534 (6)
H70.33500.67510.62780.080*
O80.2886 (3)0.47783 (15)0.67508 (11)0.0536 (6)
H80.25900.48450.71520.080*
O90.3805 (4)0.35928 (18)0.41001 (13)0.0728 (8)
O100.9171 (3)0.85590 (14)0.60537 (13)0.0619 (7)
H10C0.81670.84170.58900.074*
H10D0.90440.90150.63290.074*
O110.0863 (3)0.51355 (17)0.79506 (11)0.0628 (6)
H11E0.01250.51980.77500.075*
H11F0.09050.55190.82830.075*
C10.9025 (4)0.56650 (18)0.59817 (13)0.0304 (6)
H10.96020.53610.63730.036*
C21.0379 (4)0.62448 (18)0.55956 (13)0.0299 (6)
H21.13500.58250.54710.036*
C30.9628 (4)0.66439 (18)0.49342 (13)0.0309 (6)
H3A0.87610.71270.50510.037*
C40.8711 (4)0.58870 (19)0.45181 (13)0.0339 (7)
H4A0.80510.61910.41480.041*
C50.7409 (4)0.53505 (18)0.49644 (14)0.0346 (6)
H50.64920.57860.51190.042*
C60.6536 (4)0.4552 (2)0.45939 (16)0.0471 (8)
H6A0.60810.47650.41560.056*
H6B0.73850.40570.45090.056*
C70.6951 (4)0.61492 (17)0.68933 (13)0.0295 (6)
C80.4961 (4)0.61162 (19)0.68120 (14)0.0352 (7)
H8A0.43980.62880.72470.042*
C90.4633 (4)0.5094 (2)0.66658 (14)0.0369 (7)
H90.49910.49670.61920.044*
C100.5962 (4)0.46240 (19)0.71439 (15)0.0370 (7)
H100.54330.45460.75990.044*
C110.6622 (5)0.3694 (2)0.68905 (17)0.0497 (8)
H11A0.72610.37820.64650.060*
H11B0.56270.32850.67990.060*
C120.7704 (5)0.6936 (2)0.73225 (13)0.0437 (8)
H12A0.73640.75320.71230.052*
H12B0.89810.68990.73150.052*
C130.3859 (5)0.3717 (2)0.47033 (19)0.0516 (9)
C140.2524 (5)0.3352 (3)0.52023 (19)0.0766 (12)
H14A0.30030.28210.54410.115*
H14B0.14790.31660.49600.115*
H14C0.22330.38340.55260.115*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0524 (5)0.0546 (5)0.0466 (4)0.0006 (4)0.0119 (4)0.0130 (4)
Cl20.1087 (9)0.0690 (5)0.0311 (4)0.0230 (6)0.0028 (5)0.0049 (4)
Cl30.0934 (9)0.0619 (6)0.0980 (8)0.0202 (6)0.0228 (7)0.0209 (6)
O10.0398 (11)0.0339 (9)0.0304 (10)0.0023 (9)0.0014 (9)0.0024 (8)
O20.0281 (10)0.0377 (10)0.0273 (10)0.0053 (9)0.0027 (8)0.0068 (8)
O30.0258 (10)0.0402 (11)0.0431 (11)0.0001 (9)0.0042 (9)0.0064 (9)
O40.0352 (11)0.0427 (11)0.0413 (11)0.0018 (10)0.0055 (10)0.0128 (10)
O50.0577 (15)0.0651 (14)0.0419 (12)0.0286 (13)0.0010 (12)0.0018 (11)
O60.0326 (11)0.0340 (10)0.0321 (10)0.0010 (9)0.0045 (9)0.0071 (8)
O70.0249 (12)0.0672 (15)0.0679 (15)0.0043 (11)0.0037 (10)0.0382 (12)
O80.0330 (12)0.0719 (15)0.0560 (13)0.0154 (12)0.0016 (10)0.0056 (12)
O90.0735 (19)0.0873 (18)0.0577 (16)0.0277 (15)0.0058 (15)0.0145 (15)
O100.0496 (15)0.0453 (13)0.0908 (18)0.0043 (11)0.0205 (14)0.0132 (12)
O110.0531 (14)0.0871 (17)0.0482 (13)0.0025 (14)0.0063 (11)0.0002 (13)
C10.0294 (15)0.0322 (14)0.0295 (15)0.0043 (13)0.0043 (12)0.0033 (12)
C20.0246 (14)0.0304 (14)0.0347 (14)0.0014 (13)0.0021 (12)0.0005 (12)
C30.0260 (15)0.0334 (14)0.0333 (14)0.0017 (13)0.0038 (13)0.0034 (12)
C40.0344 (17)0.0385 (15)0.0290 (15)0.0000 (13)0.0031 (13)0.0020 (12)
C50.0333 (16)0.0392 (15)0.0314 (14)0.0043 (13)0.0031 (13)0.0014 (12)
C60.047 (2)0.0521 (18)0.0420 (17)0.0170 (16)0.0015 (16)0.0037 (15)
C70.0314 (16)0.0309 (14)0.0263 (14)0.0012 (13)0.0005 (12)0.0079 (11)
C80.0299 (17)0.0417 (16)0.0341 (15)0.0059 (14)0.0030 (13)0.0066 (13)
C90.0303 (15)0.0476 (17)0.0329 (15)0.0062 (15)0.0003 (12)0.0065 (13)
C100.0321 (16)0.0425 (17)0.0362 (16)0.0065 (14)0.0006 (14)0.0095 (14)
C110.052 (2)0.0373 (17)0.060 (2)0.0049 (16)0.0078 (17)0.0065 (16)
C120.057 (2)0.0391 (16)0.0346 (16)0.0028 (16)0.0043 (15)0.0023 (13)
C130.053 (2)0.0424 (18)0.059 (2)0.0080 (17)0.0037 (19)0.0036 (18)
C140.072 (3)0.084 (3)0.074 (3)0.040 (2)0.008 (2)0.019 (2)
Geometric parameters (Å, º) top
Cl1—C41.802 (3)C2—C31.521 (3)
Cl2—C121.765 (3)C2—H20.9800
Cl3—C111.782 (3)C3—C41.519 (4)
O1—C11.415 (3)C3—H3A0.9800
O1—C51.436 (3)C4—C51.523 (4)
O2—C11.412 (3)C4—H4A0.9800
O2—C71.434 (3)C5—C61.503 (4)
O3—C21.418 (3)C5—H50.9800
O3—H30.8200C6—H6A0.9700
O4—C31.418 (3)C6—H6B0.9700
O4—H40.8200C7—C121.512 (4)
O5—C131.321 (4)C7—C81.518 (4)
O5—C61.447 (4)C8—C91.507 (4)
O6—C71.412 (3)C8—H8A0.9800
O6—C101.454 (3)C9—C101.528 (4)
O7—C81.400 (3)C9—H90.9800
O7—H70.8200C10—C111.502 (4)
O8—C91.409 (3)C10—H100.9800
O8—H80.8200C11—H11A0.9700
O9—C131.191 (4)C11—H11B0.9700
O10—H10C0.8500C12—H12A0.9700
O10—H10D0.8500C12—H12B0.9700
O11—H11E0.8500C13—C141.498 (5)
O11—H11F0.8500C14—H14A0.9600
C1—C21.518 (4)C14—H14B0.9600
C1—H10.9800C14—H14C0.9600
C1—O1—C5112.87 (19)O6—C7—O2112.4 (2)
C1—O2—C7120.57 (18)O6—C7—C12109.4 (2)
C2—O3—H3109.5O2—C7—C12104.4 (2)
C3—O4—H4109.5O6—C7—C8105.5 (2)
C13—O5—C6117.2 (2)O2—C7—C8108.2 (2)
C7—O6—C10110.44 (19)C12—C7—C8117.1 (2)
C8—O7—H7109.5O7—C8—C9115.7 (2)
C9—O8—H8109.5O7—C8—C7109.9 (2)
H10C—O10—H10D108.6C9—C8—C7102.3 (2)
H11E—O11—H11F108.5O7—C8—H8A109.5
O2—C1—O1110.8 (2)C9—C8—H8A109.5
O2—C1—C2107.7 (2)C7—C8—H8A109.5
O1—C1—C2111.4 (2)O8—C9—C8116.2 (2)
O2—C1—H1109.0O8—C9—C10114.1 (2)
O1—C1—H1109.0C8—C9—C10101.6 (2)
C2—C1—H1109.0O8—C9—H9108.2
O3—C2—C1110.1 (2)C8—C9—H9108.2
O3—C2—C3112.4 (2)C10—C9—H9108.2
C1—C2—C3111.8 (2)O6—C10—C11109.5 (2)
O3—C2—H2107.4O6—C10—C9104.8 (2)
C1—C2—H2107.4C11—C10—C9114.0 (2)
C3—C2—H2107.4O6—C10—H10109.5
O4—C3—C4112.7 (2)C11—C10—H10109.5
O4—C3—C2107.5 (2)C9—C10—H10109.5
C4—C3—C2111.0 (2)C10—C11—Cl3111.0 (2)
O4—C3—H3A108.5C10—C11—H11A109.4
C4—C3—H3A108.5Cl3—C11—H11A109.4
C2—C3—H3A108.5C10—C11—H11B109.4
C3—C4—C5110.4 (2)Cl3—C11—H11B109.4
C3—C4—Cl1110.9 (2)H11A—C11—H11B108.0
C5—C4—Cl1110.81 (19)C7—C12—Cl2112.3 (2)
C3—C4—H4A108.2C7—C12—H12A109.1
C5—C4—H4A108.2Cl2—C12—H12A109.1
Cl1—C4—H4A108.2C7—C12—H12B109.1
O1—C5—C6107.4 (2)Cl2—C12—H12B109.1
O1—C5—C4110.8 (2)H12A—C12—H12B107.9
C6—C5—C4113.1 (2)O9—C13—O5123.8 (3)
O1—C5—H5108.5O9—C13—C14124.6 (3)
C6—C5—H5108.5O5—C13—C14111.6 (3)
C4—C5—H5108.5C13—C14—H14A109.5
O5—C6—C5108.6 (2)C13—C14—H14B109.5
O5—C6—H6A110.0H14A—C14—H14B109.5
C5—C6—H6A110.0C13—C14—H14C109.5
O5—C6—H6B110.0H14A—C14—H14C109.5
C5—C6—H6B110.0H14B—C14—H14C109.5
H6A—C6—H6B108.4
C7—O2—C1—O196.6 (2)C10—O6—C7—C813.7 (3)
C7—O2—C1—C2141.3 (2)C1—O2—C7—O610.3 (3)
C5—O1—C1—O260.7 (3)C1—O2—C7—C12108.2 (3)
C5—O1—C1—C259.1 (3)C1—O2—C7—C8126.4 (2)
O2—C1—C2—O357.0 (3)O6—C7—C8—O7156.5 (2)
O1—C1—C2—O3178.7 (2)O2—C7—C8—O736.0 (3)
O2—C1—C2—C368.7 (3)C12—C7—C8—O781.6 (3)
O1—C1—C2—C352.9 (3)O6—C7—C8—C933.1 (3)
O3—C2—C3—O462.5 (3)O2—C7—C8—C987.4 (2)
C1—C2—C3—O4173.0 (2)C12—C7—C8—C9155.0 (2)
O3—C2—C3—C4173.8 (2)O7—C8—C9—O877.6 (3)
C1—C2—C3—C449.3 (3)C7—C8—C9—O8163.0 (2)
O4—C3—C4—C5171.3 (2)O7—C8—C9—C10158.0 (2)
C2—C3—C4—C550.6 (3)C7—C8—C9—C1038.6 (3)
O4—C3—C4—Cl148.1 (3)C7—O6—C10—C11133.7 (2)
C2—C3—C4—Cl172.6 (2)C7—O6—C10—C911.0 (3)
C1—O1—C5—C6175.1 (2)O8—C9—C10—O6156.9 (2)
C1—O1—C5—C460.9 (3)C8—C9—C10—O631.1 (3)
C3—C4—C5—O155.8 (3)O8—C9—C10—C1183.4 (3)
Cl1—C4—C5—O167.5 (2)C8—C9—C10—C11150.8 (2)
C3—C4—C5—C6176.5 (2)O6—C10—C11—Cl367.2 (3)
Cl1—C4—C5—C653.2 (3)C9—C10—C11—Cl3175.7 (2)
C13—O5—C6—C5159.2 (3)O6—C7—C12—Cl258.1 (3)
O1—C5—C6—O567.8 (3)O2—C7—C12—Cl2178.66 (18)
C4—C5—C6—O5169.6 (2)C8—C7—C12—Cl261.8 (3)
C10—O6—C7—O2104.0 (2)C6—O5—C13—O93.6 (5)
C10—O6—C7—C12140.5 (2)C6—O5—C13—C14176.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O100.821.942.716 (3)158
O4—H4···O7i0.821.882.692 (3)172
O7—H7···O3ii0.821.812.610 (3)165
O8—H8···O110.822.082.844 (3)156
O10—H10C···O4iii0.851.982.820 (3)171
O10—H10D···O11iv0.852.132.972 (3)171
O11—H11E···O6ii0.852.163.011 (3)176
O11—H11F···O9v0.852.052.896 (3)176
Symmetry codes: (i) x+1/2, y+3/2, z+1; (ii) x1, y, z; (iii) x1/2, 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 formulaC14H21Cl3O9·2H2O
Mr475.69
Crystal system, space groupOrthorhombic, P212121
Temperature (K)298
a, b, c (Å)7.5824 (8), 14.2703 (14), 19.507 (2)
V3)2110.7 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.49
Crystal size (mm)0.42 × 0.22 × 0.15
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.822, 0.931
No. of measured, independent and
observed [I > 2σ(I)] reflections
8741, 3705, 2973
Rint0.042
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.081, 1.03
No. of reflections3705
No. of parameters253
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.23, 0.19
Absolute structureFlack (1983), 1569 Friedel pairs
Absolute structure parameter0.10 (6)

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O100.821.942.716 (3)157.9
O4—H4···O7i0.821.882.692 (3)172.3
O7—H7···O3ii0.821.812.610 (3)164.8
O8—H8···O110.822.082.844 (3)155.8
O10—H10C···O4iii0.851.982.820 (3)170.8
O10—H10D···O11iv0.852.132.972 (3)171.4
O11—H11E···O6ii0.852.163.011 (3)175.9
O11—H11F···O9v0.852.052.896 (3)175.6
Symmetry codes: (i) x+1/2, y+3/2, z+1; (ii) x1, y, z; (iii) x1/2, 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

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

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