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Volume 69 
Part 1 
Page o73  
January 2013  

Received 16 November 2012
Accepted 26 November 2012
Online 12 December 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.006 Å
R = 0.041
wR = 0.096
Data-to-parameter ratio = 13.8
Details
Open access

1-O-Acetyl-3,4,6-tri-O-benzyl-2-C-bromomethyl-2-deoxy-[alpha]-D-glucopyranose

aResearch Center for Synthesis and Catalysis, Department of Chemistry, University of Johannesburg (APK Campus), PO Box 524, Auckland Park, Johannesburg, 2006, South Africa
Correspondence e-mail: zhphasha@uj.ac.za

In the title compound, C30H33BrO6, the pyranose ring adopts a chair conformation. Two of the O-benzyl phenyl rings lie almost perpendicular to C/C/C/O plane formed by the ring atoms not attached to these O-benzyl phenyl rings, and form dihedral angles of 85.1 (2) and 64.6 (2)°, while the third O-benzyl phenyl ring is twisted so that it makes a dihedral angle 34.9 (2)° to this C/C/C/O plane. This twist is ascribed to the formation of an S(8) loop stabilized by a weak intramolecular C-H...O hydrogen bond.

Related literature

For background to derivatization of cyclopropyl carbohydrates, see: Halton & Harvey (2006[Halton, B. & Harvey, J. (2006). Synlett, pp. 1975-2000.]); Beyer & Madsen (1998[Beyer, J. & Madsen, R. (1998). J. Am. Chem. Soc. 120, 12137-12138.]). For details of the synthesis of the title compound, see: Gammon et al. (2007[Gammon, D. W., Kinfe, H. H., De Vos, D. E., Jacobs, P. A. & Sels, B. F. (2007). J. Carbohydr. Chem. 26, 141-157.]). For ring puckering analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C30H33BrO6

  • Mr = 569.47

  • Orthorhombic, P 21 21 21

  • a = 5.5097 (4) Å

  • b = 19.9357 (11) Å

  • c = 24.4597 (16) Å

  • V = 2686.6 (3) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 2.43 mm-1

  • T = 100 K

  • 0.43 × 0.05 × 0.05 mm

Data collection
  • Bruker APEX DUO 4K-CCD diffractometer

  • Absorption correction: multi-scan (SADABS, Bruker, 2008[Bruker (2008). SADABS and SAINT . Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.613, Tmax = 0.753

  • 51826 measured reflections

  • 4637 independent reflections

  • 4177 reflections with I > 2[sigma](I)

  • Rint = 0.097

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.096

  • S = 1.04

  • 4637 reflections

  • 335 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 1.04 e Å-3

  • [Delta][rho]min = -0.61 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1893 Friedel pairs

  • Flack parameter: -0.01 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C18-H18...O4 0.95 2.85 3.663 (7) 144

Data collection: APEX2 (Bruker, 2011[Bruker (2011). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). SADABS and SAINT . Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT (Bruker, 2008[Bruker (2008). SADABS and SAINT . Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007[Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.]); 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: HG5273 ).


Acknowledgements

Support by the research funds of the University of Johannesburg is gratefully acknowledged.

References

Beyer, J. & Madsen, R. (1998). J. Am. Chem. Soc. 120, 12137-12138.  [ISI] [CrossRef] [ChemPort]
Bruker (2008). SADABS and SAINT . Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2011). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
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]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Gammon, D. W., Kinfe, H. H., De Vos, D. E., Jacobs, P. A. & Sels, B. F. (2007). J. Carbohydr. Chem. 26, 141-157.  [ISI] [CrossRef] [ChemPort]
Halton, B. & Harvey, J. (2006). Synlett, pp. 1975-2000.
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o73  [ doi:10.1107/S1600536812048453 ]

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