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Volume 69 
Part 9 
Pages o1449-o1450  
September 2013  

Received 1 August 2013
Accepted 12 August 2013
Online 17 August 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
R = 0.016
wR = 0.043
Data-to-parameter ratio = 25.0
Details
Open access

Methyl 6-deoxy-6-iodo-2,3-O-isopropylidene-[alpha]-D-mannopyranoside

aDepartment of Chemistry, Çankiri Karatekin University, TR-18100, Çankiri, Turkey,bUniversität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany,cDepartment of Physics, Sakarya University, 54187 Esentepe, Sakarya, Turkey, and dDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
Correspondence e-mail: merzifon@hacettepe.edu.tr

In the title compound, C10H17IO5, the six-membered tetrahydropyran ring and the five-membered 1,3-dioxolane ring adopt sofa and envelope conformations, respectively. In the crystal, O-H...O and C-H...O hydrogen bonds link the molecules into layers nearly parallel to the bc plane.

Related literature

For carbohydrates which are important for the preparation of unsaturated aldehydes, see: Kleban et al. (2000[Kleban, M., Kautz, U., Greul, J. N., Hilgers, P., Kugler, R. D., Dong, H.-Q. & Jäger, V. (2000). Synthesis, pp. 1027-1033.]); Dransfield et al. (1999[Dransfield, P. J., Moutel, S., Shipman, M. & Sik, V. (1999). J. Chem. Soc. Perkin Trans. 1, pp. 3349-3335.]); Greul et al. (2001[Greul, J. N., Kleban, M., Schneider, B., Picasso, S. & Jäger, V. (2001). ChemBioChem, pp. 368-370.]). For conversions of unsaturated aldehydes to oximes, nitrones and nitrile oxides, see: Dransfield et al. (1999[Dransfield, P. J., Moutel, S., Shipman, M. & Sik, V. (1999). J. Chem. Soc. Perkin Trans. 1, pp. 3349-3335.]); Bernet & Vasella (1979[Bernet, B. & Vasella, A. (1979). Helv. Chim. Acta, 62, 2401-2410.]); Greul et al. (2001[Greul, J. N., Kleban, M., Schneider, B., Picasso, S. & Jäger, V. (2001). ChemBioChem, pp. 368-370.]); Gallos et al. (1999[Gallos, J. K., Koumbis, A. E., Xiraphaki, V. P., Dellios, C. C. & Coutouli-Argyropoulou, E. (1999). Tetrahedron, 55, 15167-15180.]); Kleban et al. (2001[Kleban, M., Hilgers, P., Greul, J. N., Kugler, R. D., Li, J., Picasso, S., Vogel, P. & Jäger, V. (2001). Chembiochem, pp. 365-368.]). For the methods reported in the literature for the preparation of the title compound, see: Garegg & Samuelsson (1980[Garegg, P. J. & Samuelsson, B. (1980). J. Chem. Soc. Perkin Trans. 1, pp. 2866-2869.]); Bundle et al. (1988[Bundle, D. R., Gerken, M. & Peters, T. (1988). Carbohydr. Res. 174, 239-251.]); Ichikawa et al. (2004[Ichikawa, Y., Matsukawa, Y., Nishiyama, T. & Isobe, M. (2004). Eur. J. Org. Chem. pp. 586-591.]). For the synthesis of methyl 2,3-O-isopropylidene-[alpha]-D-mannopyranoside, see: Evans & Parrish (1977[Evans, M. E. & Parrish, F. W. (1977). Carbohydr. Res. 54, 105-114.]); Isobe et al. (1981[Isobe, M., Ichikawa, Y., Kitamura, M. & Goto, T. (1981). Chem. Lett. pp. 457-460.]). For ring-puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C10H17IO5

  • Mr = 344.14

  • Monoclinic, P 21

  • a = 8.3121 (8) Å

  • b = 10.3911 (10) Å

  • c = 8.3128 (8) Å

  • [beta] = 118.639 (3)°

  • V = 630.15 (11) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 2.55 mm-1

  • T = 100 K

  • 0.99 × 0.58 × 0.44 mm

Data collection
  • Bruker Kappa APEXII DUO diffractometer

  • Absorption correction: numerical (Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.187, Tmax = 0.401

  • 13656 measured reflections

  • 3827 independent reflections

  • 3803 reflections with I > 2[sigma](I)

  • Rint = 0.027

  • Standard reflections: 0

Refinement
  • R[F2 > 2[sigma](F2)] = 0.016

  • wR(F2) = 0.043

  • S = 1.24

  • 3827 reflections

  • 153 parameters

  • 3 restraints

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

  • [Delta][rho]max = 0.86 e Å-3

  • [Delta][rho]min = -0.82 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1811 Friedel pairs

  • Absolute structure parameter: 0.003 (12)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2A...O3i 0.82 (3) 2.03 (3) 2.807 (2) 157 (3)
C10-H10C...O2ii 0.98 2.51 3.390 (3) 149
Symmetry codes: (i) [-x+2, y-{\script{1\over 2}}, -z+2]; (ii) x, y, z+1.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. 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: 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.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5727 ).


Acknowledgements

The authors are indebted to the Research Fund of Çankiri Karatekin University (grant No. BAP:2011/06) for financial support, and thank Professor V. Jäger of Stuttgart University, Germany, for helpful discussions.

References

Bernet, B. & Vasella, A. (1979). Helv. Chim. Acta, 62, 2401-2410.
Blessing, R. H. (1995). Acta Cryst. A51, 33-38.  [CrossRef] [details]
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bundle, D. R., Gerken, M. & Peters, T. (1988). Carbohydr. Res. 174, 239-251.  [CrossRef] [ChemPort] [PubMed] [ISI]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Dransfield, P. J., Moutel, S., Shipman, M. & Sik, V. (1999). J. Chem. Soc. Perkin Trans. 1, pp. 3349-3335.  [CrossRef]
Evans, M. E. & Parrish, F. W. (1977). Carbohydr. Res. 54, 105-114.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Gallos, J. K., Koumbis, A. E., Xiraphaki, V. P., Dellios, C. C. & Coutouli-Argyropoulou, E. (1999). Tetrahedron, 55, 15167-15180.  [ISI] [CrossRef] [ChemPort]
Garegg, P. J. & Samuelsson, B. (1980). J. Chem. Soc. Perkin Trans. 1, pp. 2866-2869.  [CrossRef]
Greul, J. N., Kleban, M., Schneider, B., Picasso, S. & Jäger, V. (2001). ChemBioChem, pp. 368-370.  [CrossRef]
Ichikawa, Y., Matsukawa, Y., Nishiyama, T. & Isobe, M. (2004). Eur. J. Org. Chem. pp. 586-591.  [CrossRef]
Isobe, M., Ichikawa, Y., Kitamura, M. & Goto, T. (1981). Chem. Lett. pp. 457-460.  [CrossRef] [ISI]
Kleban, M., Hilgers, P., Greul, J. N., Kugler, R. D., Li, J., Picasso, S., Vogel, P. & Jäger, V. (2001). Chembiochem, pp. 365-368.  [CrossRef]
Kleban, M., Kautz, U., Greul, J. N., Hilgers, P., Kugler, R. D., Dong, H.-Q. & Jäger, V. (2000). Synthesis, pp. 1027-1033.  [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1449-o1450   [ doi:10.1107/S1600536813022629 ]

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