Abstract
The X-ray crystal structures of 1,4,6,9-tetrathiaspiro[4.4]nonane (4) and 1,5,7,11-tetrathiaspiro[5.5]undecane (3) have been determined. Crystals of4 are tetragonal, space groupI41 cd, with eight molecules in a unit cell of dimensionsa=9.521 (2) andc=19.052(5) Å. Crystals of3 are orthorhombic,Pbca, with eight moleucles in a cell havinga=8.955(3),b=12.356(4), andc=18.425(4) Å. Compound4 was solved from the Patterson map and3 by use ofMultan, and they refined to finalR values of 6.4 and 2.5%, respectively. Compound4 consists of two 1,3-dithiolane rings connected via C(2), both of which appear to be somewhat disordered at room temperature. The uncorrected C-C distance is 1.476 Å and the average S-C distance is 1.786 Å. Compound3 consists of two 1,3-dithiane rings connected at C(2), both in chair conformations. In both compounds there appear to be electronic repulsions between S lone pairs and axial hydrogens of the opposite ring system. Analysis of endocyclic torsion angles in3 indicates that the ring conformations themselves are not significantly altered by the positional shift caused by the repulsion.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Andreeti, G. D., Bocelli, G., Sgarabotto, P., Ugozolli, F., and Grenier-Loustalot, M. F. (1979)Cryst. Struct. Commun. 8, 751.
Blount, J. F., Coffen, D. L., and Wong, F. (1974)J. Org. Chem. 39, 2374.
Brahde, L. B. (1954)Acta Chem. Scand. 8, 1145.
Cromer, D. T., and Mann, J. B. (1968)Acta Cryst. A 24, 321.
D'Amico, J. J. (1972) U.S. Patent No. 3,652,256, Monsanto Co.
D'Amico, J. J., and Campbell, R. H. (1967)J. Org. Chem. 32, 2567.
Depmeier, W., and Jarchow, O. H. (1975)Acta Cryst. B. 31, 939.
DeSimone, R. E., and Glick, M. D. (1976)J. Am. Chem. Soc. 98, 762.
Eliel, E. L., and Allinger, N. L., eds. (1969)Topics in Stereochemistry, Vol. 4 (Wiley, New York), pp. 39–98.
Germain, G., Main, P., and Woolfson, M. M. (1971)Acta Cryst. A 27, 368.
Hauptmann, H., and Maura Campos, M. (1952)J. Am. Chem. Soc. 74, 3179.
Hauptmann, H., and Bobbio, F. O. (1960)Chem. Ber. 93, 2187.
Johnson, T. P., Strongfellow, C. R., Jr., and Gallagher, A. (1962)J. Org. Chem. 27, 4068.
Kalff, H. T., and Romers, C. (1966)Acta Cryst. 20, 490.
Klaska, K.-H., Jarchow, O., Koebernick, W., and Paulsen, H. (1977)Carbohydr. Res. 56, 67.
Klewe, B., and Seip, H. M. (1972)Acta Chem. Scand. 26, 1860.
Korp, J. D., Bernal, I., Watkins, S. F., and Fronczek, F. R. (1982)J. Heterocycl. Chem. 19, 459.
Luss, H. R., and Smith, D. L. (1973)Acta Cryst. B 29, 998.
McPhail, A. T., Onan, K. D., and Koskimies, J. (1976)J. Chem. Soc., Perkin Trans. 2, 1005.
Mercer, M., and Truter, M. R. (1973)J. Chem. Soc., Dalton Trans., 2215.
Pauling, L. (1960)The Nature of the Chemical Bond (Cornell University Press, Ithaca, New York), 3rd edn.
Sheldrick, G. M. (1976)Shelx-76 Programs for Crystal Structure Determination, Cambridge University.
Sletten, J. (1974)Acta Chem. Scand. A 28, 499.
Stewart, R. F., Davidson, E. R., and Simpson, W. T. (1965)J. Chem. Phys. 42, 3175.
Williams, D. R., Coffen, D. L., Garrett, P. E., and Schwartz, R. N. (1968)J. Chem. Soc. B, 1132.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Korp, J.D., Bernal, I. The stereochemistry of organosulfur compounds. XX. The x-ray crystal and molecular structures of two tetrathiaspiroalkanes. Journal of Crystallographic and Spectroscopic Research 15, 201–209 (1985). https://doi.org/10.1007/BF01181807
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF01181807