Abstract
The lattice type crystalline inclusion compound of 1,1′-binaphthyl-2,2′-dicarboxylic acid (BNDA) with acetylacetone (AcAc) 1∶1 has been investigated by single crystal X-ray diffraction. AcAc is present as the enolic tautomer, stabilized by a notably short intramolecular hydrogen bond. This H-bond closes a six-membered ring with delocalization of the system of conjugated double bonds. In the crystal the AcAc molecules are incorporated into channels, delimited by bulky binaphyl moieties, in a hydrogen-bonded framework of BNDA, and they do not show any disorder. The strictly stoichiometric host:guest ratio seems to be enforced by packing forces only.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Atwood, J.L.; Davies, J.E.D.; MacNicol, D.D. (Eds.)Inclusion Compounds, Vols. 1–3; Academic Press: London, 1984; Vols. 4 and 5; Oxford university press: Oxford 1991.
Desiraju, G.R.Crystal Engineering, Materials Science Monographs, vol. 54; Elsevier: Amsterdam, 1989.
Weber, E.J. Mol. Graphics. 1989,7, 12.
Weber, E.; Czugler, M.Molecular Inclusion and Molecular Recognition—Clathrates-II, Topics in Current Chemistry; Weber, E., Ed.; Springer-Verlag: Berlin Heidelberg 1988; Vol. 149, p 45.
Weber, E.Inclusion Compounds; Atwood, J.L.; Davies, J.E.D.; MacNicol, D.D., Eds.; Oxford University Press: Oxford 1991; Vol. 4, p 188.
Weber, E.; Csöregh, I.; Stensland, B.; Czugler, M.J. Am. Chem. Soc. 1984,106, 3297.
Csöregh, I.; Czugler, M.; Weber, E.; Ahrendt J.J. Incl. Phenom. 1990,8, 309.
Czugler, M.; Ángyán, J.G.; Náray-Szabó, G.; Weber, E.J. Am. Chem. Soc. 1986,108, 1275.
Czugler, M.; Weber, E.J. Incl. Phenom. 1991,10, 355.
Bertolasi, V.; Gilli, P.; Ferretti, V.; Gilli, G.J. Am. Chem. Soc. 1991,113, 4917.
Sheldrick, G.M.SHELXS86. Program for the Solution of Crystal Structures; University of Göttingen: Germany, 1986.
Sheldrick, G.M.SHELX76. Program for Crystal Structure Determination; University of Cambridge, England, 1976.
Hamilton, W.C.; Ibers, J.A.Hydrogen Bonding in Solids; W.A. Bendjamin, Inc.: New York,1968; p. 15.
Csöregh, I.; Czugler, M.; Weber, E.; Sjögren, A.; Cserzö, M.J. Chem. Soc. Perkin Trans. 2,1986, 507.
Olovsson, I.; Jönsson, P.-G.The Hydrogen Bond—Recent Developments in Theory and Experiments, Vol. II; North-Holland: Amsterdam, 1976, p. 395.
Csöregh, I.; Czugler, M.; Törnroos, K.W.; Weber, E.; Ahrendt, J.J. Chem. Soc. Perkin Trans. 2,1989, 1491.
Taylor, R.; Kennard, O.J. Am. Chem. Soc. 1982,104, 5063.
Lowrey, A.H.; George, G.; D'Antonio, P.; Karle, J.J. Am. Chem. Soc. 1971,93, 6399.
Camerman, A.; Mastropaulo, D.; Camerman, N.J. Am. Chem. Soc. 1985,105, 1584.
Iijima, K.; Ohnogi, A.; Shibata, S.J. Mol. Struct. 1987,156, 111.
Gilli, G.; Bellucci, F.; Ferretti, V.; Bertolasi, V.J. Am. Chem. Soc. 1989,111, 1023.
Leiserowitz, L.Acta Crystallogr. 1976,B32, 775.
Weber, E.Molecular Inclusion and Molecular Recognition—Clathrates I, Topics in Current Chemistry; Weber, E., Ed.; Springer-Verlag: Berlin-Heidelberg, 1987; Vol. 140, p 1.
Motherwell, S.; Clegg, B.PLUTO, Program for Plotting Molecular and Crystal Structures; University of Cambridge: England, 1978.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Gallardo, O., Csöregh, I. & Weber, E. Crystal and molecular structure of the inclusion compound between 1,1′-binaphthyl-2,2′-dicarboxylic acid and acetylacetone (1∶1). J Chem Crystallogr 25, 769–776 (1995). https://doi.org/10.1007/BF01670334
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF01670334