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Volume 69 
Part 9 
Page o1399  
September 2013  

Received 24 June 2013
Accepted 5 August 2013
Online 10 August 2013

Key indicators
Single-crystal X-ray study
T = 291 K
Mean [sigma](C-C) = 0.003 Å
R = 0.037
wR = 0.099
Data-to-parameter ratio = 13.0
Details
Open access

1,2:1',2'-Di-O-isopropylidenedifuranose-C12 higher carbon sugar

aNew Drug Reseach & Development Center, Zhengzhou Univresity, Zhengzhou 450001, People's Republic of China
Correspondence e-mail: zqr409@163.com

In the title compound, C18H28O8, the five-membered ring with one O atom attached to the ethyl substituent has a twisted conformation about the C-O bond. The adjacent cis-fused ring with two O atoms also has a twisted conformation about one of the C-O bonds. The dihedral angle between these rings (all atoms) is 59.05 (12)°. The five-membered ring linked to the ethynyl susbtituent is twisted about a C-C bond; the cis-fused adjacent ring is twisted about a C-O bond [dihedral angle between the rings (all atoms) = 71.78 (12)°]. Two intramolecular O-H...O hydrogen bonds occur. In the crystal, molecules are linked by O-H...O hydrogen bonds, generating [001] chains.

Related literature

For further synthetic details, see: Meyer & Jochims (1969[Meyer, R. & Jochims (1969). Chem. Ber. 102, 4199-4206.]). For background to higher-carbon sugars, see: Iwasa et al. (1978[Iwasa, T., Kusuka, T. & Suetomi, K. (1978). J. Antibiot. 31, 511-518.]); Harada et al. (1981[Harada, S., Mizuta, E. & Kishi, T. (1981). Tetrahedron, 37, 1317-1327.]); Liu et al. (2006[Liu, H.-M., Liu, F.-W., Song, X.-P. & Zhang, J.-Y. (2006). Tetrahedron, 17, 3230-3236.]).

[Scheme 1]

Experimental

Crystal data
  • C18H28O8

  • Mr = 372.40

  • Orthorhombic, P 21 21 2

  • a = 21.5802 (6) Å

  • b = 15.3758 (4) Å

  • c = 5.73626 (14) Å

  • V = 1903.37 (8) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.86 mm-1

  • T = 291 K

  • 0.28 × 0.25 × 0.25 mm

Data collection
  • Agilent Xcalibur (Eos, Gemini) diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996)[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.] Tmin = 0.796, Tmax = 0.815

  • 7406 measured reflections

  • 3407 independent reflections

  • 3079 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.099

  • S = 1.05

  • 3407 reflections

  • 262 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.14 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3'-H3'...O4'i 0.79 (3) 2.36 (3) 3.038 (2) 144 (2)
O3'-H3'...O2' 0.79 (3) 2.22 (3) 2.685 (2) 119 (2)
O3-H3...O2 0.82 (4) 2.11 (3) 2.647 (2) 122 (3)
Symmetry code: (i) x, y, z+1.

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7100 ).


Acknowledgements

We gratefully acknowledge the financial support of the National Natural Science Foundation of China (grant No. 81172937).

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
Harada, S., Mizuta, E. & Kishi, T. (1981). Tetrahedron, 37, 1317-1327.  [CrossRef] [ChemPort] [ISI]
Iwasa, T., Kusuka, T. & Suetomi, K. (1978). J. Antibiot. 31, 511-518.  [CrossRef] [ChemPort] [PubMed]
Liu, H.-M., Liu, F.-W., Song, X.-P. & Zhang, J.-Y. (2006). Tetrahedron, 17, 3230-3236.  [ChemPort]
Meyer, R. & Jochims (1969). Chem. Ber. 102, 4199-4206.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1399  [ doi:10.1107/S1600536813021776 ]

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