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Volume 69 
Part 2 
Page o157  
February 2013  

Received 26 November 2012
Accepted 20 December 2012
Online 4 January 2013

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Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.008 Å
R = 0.058
wR = 0.151
Data-to-parameter ratio = 9.3
Details
Open access

Isopropyl 2,3,4,6-tetra-O-acetyl-[beta]-D-glucopyranoside

Bettina Mönch,a Franziska Emmerling,a* Werner Kraus,a Roland Beckera and Irene Nehlsa

aBAM Federal Institute for Materials Research and Testing, Department of Analytical Chemistry, Reference Materials, Richard-Willstätter-Strasse 11, D-12489 Berlin, Germany
Correspondence e-mail: franziska.emmerling@bam.de

The title compound, C17H26O10, was formed by a Koenigs-Knorr reaction of 2,3,4,6-tetra-O-acetyl-[alpha]-D-glucopyranosyl bromide and propan-2-ol. The central ring adopts a chair conformation. The crystal does not contain any significant intermolecular interactions.

Related literature

Metabolites of alcohol are important markers for previous alcohol consumption, see: Joya et al. (2012[Joya, X., Friguls, B., Papaseit, E., Martínez, S. E., Manich, A., Garcia-Algar, O., Pacifici, R. & Pichini, S. (2012). J. Pharm. Biomed. Anal. 69, 209-222.]); Helander et al. (2012[Helander, A., Péter, O. & Zheng, Y. (2012). Alcohol Alcohol. 47, 552-557.]). For investigation of the short-chain alkyl alcohol content in alcoholic beverages, see: Lachenmeier & Musshoff (2004[Lachenmeier, D. W. & Musshoff, F. (2004). Rechtsmedizin, 14, 454-462.]). For the relevance of short-chain alkyl alcohol glucuronides as alcohol markers, see; Sticht & Käferstein (1999[Sticht, G. & Käferstein, H. (1999). Rechtsmedizin, 9, 184-189.]). For related synthesis, see: Baer & Abbas (1979[Baer, H. H. & Abbas, S. A. (1979). Carbohydr. Res. 77, 117-129.]).

[Scheme 1]

Experimental

Crystal data

  • C17H26O10

  • Mr = 390.38

  • Monoclinic, P 21

  • a = 9.4225 (12) Å

  • b = 9.9313 (12) Å

  • c = 11.3641 (15) Å

  • [beta] = 98.482 (9)°

  • V = 1051.8 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 296 K

  • 0.28 × 0.12 × 0.11 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.221, Tmax = 0.364

  • 11225 measured reflections

  • 2274 independent reflections

  • 1411 reflections with I > 2[sigma](I)

  • Rint = 0.107
Refinement

  • R[F2 > 2[sigma](F2)] = 0.058

  • wR(F2) = 0.151

  • S = 1.07

  • 2274 reflections

  • 244 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.13 e Å-3

Data collection: APEX2 (Bruker, 2001[Bruker (2001). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.]); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6870 ).

References

Baer, H. H. & Abbas, S. A. (1979). Carbohydr. Res. 77, 117-129.  [CrossRef] [ChemPort] [ISI]
Bruker (2001). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
Helander, A., Péter, O. & Zheng, Y. (2012). Alcohol Alcohol. 47, 552-557.  [CrossRef] [ChemPort] [PubMed]
Joya, X., Friguls, B., Papaseit, E., Martínez, S. E., Manich, A., Garcia-Algar, O., Pacifici, R. & Pichini, S. (2012). J. Pharm. Biomed. Anal. 69, 209-222.  [ISI] [CrossRef] [ChemPort] [PubMed]
Lachenmeier, D. W. & Musshoff, F. (2004). Rechtsmedizin, 14, 454-462.  [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sticht, G. & Käferstein, H. (1999). Rechtsmedizin, 9, 184-189.  [CrossRef]

Acta Cryst (2013). E69, o157  [ doi:10.1107/S1600536812051483 ]

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