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Volume 69 
Part 10 
Page o1512  
October 2013  

Received 16 May 2013
Accepted 9 August 2013
Online 7 September 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.007 Å
Disorder in main residue
R = 0.046
wR = 0.130
Data-to-parameter ratio = 15.2
Details
Open access

1,2:5,6-Di-O-isopropylidene-3-C-methyl-[alpha]-D-allofuranose

aDepartamento de Química Orgânica, Instituto de Química, Universidade Federal Fluminense, Niterói - RJ, CEP 24020-150, Brazil, and bDepartamento de Química Inorgânica, Instituto de Química, Universidade Federal Fluminense, Niterói - RJ, CEP 24020-150, Brazil
Correspondence e-mail: fernand@vm.uff.br

The title carbohydrate, C13H22O6, is a derivative of D-glycose, in which the furanosidic and isopropylidene rings are in twisted conformations. The mean plane of the furanosidic ring makes a dihedral angle of 70.32 (18)° with the mean plane of the fused isopropylidene ring. The methyl groups in the other isopropylidene ring are disordered over two sets of sites, with an occupancy ratio of 0.74 (6):0.26 (6). In the crystal, molecules are linked by O-H...O hydrogen bonds into chains with graph-set notation C(5) along [100]. Weak C-H...O interactions also occur.

Related literature

For background information on this class of compound, see: Bio et al. (2004[Bio, M. M., Xu, F., Waters, M., Williams, J. M., Savary, K. A., Cowden, C. J., Yang, C., Buck, E., Song, Z. J., Tschaen, D., Volante, R. P., Reamer, R. A. & Grabowski, E. J. J. (2004). J. Org. Chem. 69, 6257-6266.]); Canuto et al. (2007[Canuto, C. V. B. S., Gomes, C. R. B., Marques, I. P., Faro, L. V., Santos, F. C., Frugulhetti, I. C. P. P., Souza, T. M. L., Cunha, A. C., Romeiro, G. A., Ferreira, V. F. & Souza, M. C. B. V. (2007). Lett. Drug. Des. Discov. 4, 404-409.]); Mane et al. (2008[Mane, R. S., Kumar, K. S. A. & Dhavale, D. D. (2008). J. Org. Chem. 73, 3284-3287.]); Yoneda et al. (2011[Yoneda, J. D., Velloso, M. H. R., Leal, K. Z., Azeredo, R. B. V., Sugiura, M., Albuquerque, M. G., Santos, F. C., Souza, M. C. B. V., Cunha, A. C., Seidl, P. R., Alencastro, R. B. & Ferreira, V. F. (2011). J. Mol. Struct. 985, 1-4.]). For details of ring-puckering calculations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). Graph-set notation for the description of hydrogen-bonding motifs is given by Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 35, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C13H22O6

  • Mr = 274.3

  • Triclinic, P 1

  • a = 5.503 (4) Å

  • b = 8.113 (1) Å

  • c = 9.122 (2) Å

  • [alpha] = 99.65 (2)°

  • [beta] = 103.69 (3)°

  • [gamma] = 98.86 (2)°

  • V = 382.0 (3) Å3

  • Z = 1

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.14 × 0.11 × 0.08 mm

Data collection
  • Nonius KappaCCD diffractometer

  • 9589 measured reflections

  • 2758 independent reflections

  • 2107 reflections with I > 2[sigma](I)

  • Rint = 0.043

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.130

  • S = 1.04

  • 2758 reflections

  • 181 parameters

  • 8 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

  • Absolute structure: Flack x calculated using 872 quotients [(I+) - (I-)]/[(I+) + (I-)] (Parsons & Flack, 2004[Parsons, S. & Flack, H. (2004). Acta Cryst. A60, s61.]). There is insufficient information present to define handedness

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H3...O4i 0.82 2.28 3.022 (4) 152
C1-H1...O2ii 0.98 2.58 3.218 (5) 123
C2-H2...O6iii 0.98 2.54 3.504 (5) 167
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z; (iii) x, y, z+1.

Data collection: COLLECT (Nonius, 2004[Nonius (2004). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DIRAX/LSQ (Duisenberg, 1992[Duisenberg, A. J. M. (1992). J. Appl. Cryst. 25, 92-96.]); data reduction: EVALCCD (Duisenberg et al., 2003[Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2013[Sheldrick, G. M. (2013). SHELXL2013. University of Göttingen, Germany.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2484 ).


Acknowledgements

This work was supported by the Brazilian agencies FAPERJ, CAPES and CNPq, and by the X-ray diffraction laboratory LDRX-UFF for the data collection.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 35, 1555-1573.  [CrossRef] [Web of Science]
Bio, M. M., Xu, F., Waters, M., Williams, J. M., Savary, K. A., Cowden, C. J., Yang, C., Buck, E., Song, Z. J., Tschaen, D., Volante, R. P., Reamer, R. A. & Grabowski, E. J. J. (2004). J. Org. Chem. 69, 6257-6266.  [CrossRef] [PubMed] [ChemPort]
Canuto, C. V. B. S., Gomes, C. R. B., Marques, I. P., Faro, L. V., Santos, F. C., Frugulhetti, I. C. P. P., Souza, T. M. L., Cunha, A. C., Romeiro, G. A., Ferreira, V. F. & Souza, M. C. B. V. (2007). Lett. Drug. Des. Discov. 4, 404-409.  [ChemPort]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Duisenberg, A. J. M. (1992). J. Appl. Cryst. 25, 92-96.  [CrossRef] [ChemPort] [Web of Science] [IUCr Journals]
Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Mane, R. S., Kumar, K. S. A. & Dhavale, D. D. (2008). J. Org. Chem. 73, 3284-3287.  [CrossRef] [PubMed] [ChemPort]
Nonius (2004). COLLECT. Nonius BV, Delft, The Netherlands.
Parsons, S. & Flack, H. (2004). Acta Cryst. A60, s61.  [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2013). SHELXL2013. University of Göttingen, Germany.
Yoneda, J. D., Velloso, M. H. R., Leal, K. Z., Azeredo, R. B. V., Sugiura, M., Albuquerque, M. G., Santos, F. C., Souza, M. C. B. V., Cunha, A. C., Seidl, P. R., Alencastro, R. B. & Ferreira, V. F. (2011). J. Mol. Struct. 985, 1-4.  [Web of Science] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1512  [ doi:10.1107/S1600536813022447 ]

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