Abstract
The crystal structure of the title lactone, C20H30O9, a potential precursor of uncommon 11-carbon sugar derivatives, has been determined by single-crystal diffraction methods. The compound crystallizes in the orthorhombic space groupP212121 witha=15.581(3),b=14.047(2),c=9.888(2) Å, andZ=4. The structure was solved by direct methods and refined by full-matrix least-squares toR=0.054. The absolute configuration of the seven stereogenic carbon atoms was deduced as 4R, 5R, 6R, 7R, 8S, 9R, 10R, being (R)-(+)-glyceraldehyde its progenitor. An intramolecular O-H⋯O hydrogen bond is present. Weak interaction C-H⋯O links the molecules in sheets parallel to the (100) plane.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Belletti, D., Cantoni, A., and Pasquinelli, G. (1988). Gestione on line di diffrattometro a cristallo singolo Siemens AED con sistema IBM PS2/30, Centro di Studio per la Strutturistica Diffrattometrica del CNR, Parma, Italy: Internal report 1/88.
Casiraghi, G., Colombo, L., Rassu, G., and Spanu, P. (1990a).J. Org. Chem. 55, 2565.
Casiraghi, G., Colombo, L., Rassu, G., Spanu, P., Gasparri Fava, G., and Ferrari Belicchi, M. (1990b).Tetrahedron 46, 5807.
Casiraghi, G., Colombo, L., Rassu, G., and Spanu, P. (1991a).J. Org. Chem.,56, 2135.
Casiraghi, G., Rassu, G., Gasparri Fava, G., Ferrari Belicchi, M., and Belletti, D. (1991b).J. Cryst. Spec. Res.,21, 261.
Cremer, D., and Pople, J. A. (1975).J. Am. Chem. Soc. 97, 1354.
Danishefsky, S. J., and De Ninno, M. P. (1987).Angew. Chem. Int. Ed. Engl. 26, 15.
Johnson, C. K. (1976).Ortep Fortran Thermal-ellipsoid Program for Crystal Structure Illustrations. ReportOrnl-5138 (Oak Ridge National Laboratory, Oak Ridge, Tenn.).
Kennard, O., Watson, D. G., Allen, F. H., Motherwell, W. D. S., Town, W., and Rogers, J. R. (1975).Chem. Br. 11, 213.
Lehmann, M. S., and Larsen, F. K. (1974).Acta Crystallogr. A 30, 580.
Matijasic, I., Bocelli, G., Ugozzoli, F., and Sgarabotto, P. (1988).Acta Crystallogr. C 44, 159.
Motherwell, W. D. S. (1976).Pluto,A program for plotting molecular and crystal structures (University Chemical Laboratory, Cambridge, England).
Nardelli, M. (1983).Comput. Chem. 7, 95.
Ruzic-Toros, Z., and Leban, I. (1978).Acta Crystallogr. B 34, 1226.
Sheldrick, G. M. (1976).Shelx-76. A program for crystal structure determination (University Chemical Laboratory, Cambridge, England).
Sheldrick, G. M. (1985).Shelx-86. Crystallographic computing 3, Oxford University press.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Fava, G.G., Ferrari, M.B., Casiraghi, G. et al. Crystal and molecular structure of (+)-6,7∶8,9∶10,11-tri-O-isopropylidene-2,3-dideoxy-d-arabino-l-allo-undec-2-enono-1,4-lactone, C20H30O9 . Journal of Crystallographic and Spectroscopic Research 21, 629–633 (1991). https://doi.org/10.1007/BF01161086
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF01161086