Abstract
The crystal structure of 4-cyanocubanecarboxylic acid contains the same syn–anti carboxyl group catemer that is found in other cubane monocarboxylic acids. The cyano groups are arranged according to the type-II geometry, in that they are 21 screw-axis related. Curiously, there is a 5% orientational disorder of the cyano and anti carboxyl groups. The ester of the title acid packs isostructurally with the corresponding chloro and fluoro analogs because of the importance of the C—H...O hydrogen bond patterns. 1,4-Dicyanocubane forms solid solutions with 1,4-dibromocubane, but, interestingly, the crystal structure of the solid solution is distinct from that of either component. The formation of these solid solutions seems to be governed by shape and size factors.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
REFERENCES
Eaton, P. E.; Galoppini, E.; Gilardi, R. J. Amer. Chem. Soc. 1994, 16, 7588.
Irngartinger, H.; Strack, S.; Gredel, F. Liebigs Ann. 1996, 311, 315.
Zhang, M.-X.; Eaton, P. E.; Gilardi, R. Angew. Chem. Intern. Ed. Engl. 2000, 39, 401.
Kuduva, S. S.; Craig, D. C.; Nangia, A.; Desiraju, G. R. J. Amer. Chem. Soc. 1999, 121, 1936.
The type-I and type-II nomenclature is based on the angles θ1 and θ2 in the C—X· ·X—C contact. When θ1 ≅ θ2 the contact is denoted as type-I and when θ1 ≅ 90 and θ2 ≅ 180, it is denoted as type-II. See the following for details: (a) Desiraju, G. R.; Parthasarathy, R. J. Amer. Chem. Soc. 1989, 111, 8725; (b) Pedireddi, V. R.; Reddy, D. S.; Goud, B. G.; Craig, D. C.; Rae, A. D.; Desiraju, G. R. J. Chem. Soc. Perkin Trans. 2 1994, p. 2353; (c) Navon, O.; Bernstein, J.; Khodorkovsky, V. Angew. Chem. Intern. Ed. Eng. 1997, 36, 601.
Desiraju, G. R.; Harlow, R. L. J. Amer. Chem. Soc. 1989, 111, 6757.
Thaimattam, R.; Langley, P. J.; Hulliger, J.; Desiraju, G. R. New J. Chem. 1998, p. 1307.
Kitaigorodskii, A. I. Mixed Crystals; Springer: Berlin, 1984.
Kawai, N. T.; Gilson, D. F. R.; Britten, J. F.; Butler, I. S.; Farrell, P. G. Can. J. Chem., 1992, 70, 910.
Della, E. W.; Head, N. J. J. Org. Chem. 1995, 60, 5303.
Sheldrick, G. M. SHELX97: Program for the Solution and Refinement of Crystal Structures; University of Göttingen: Germany, 1997.
SIR92: Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Polidori, G. J. Appl. Crystallogr. 1994, 27, 435.
RAELS: Rae, A. D. A Comprehensive Constrained Least Squares Refinement Program, University of New South Wales, 1989.
PLATON: Spek, A. L. Bijvoet Center for Biomolecular Research, Vakgroep Kristal en Structure chemie, University of Utrecht.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Kuduva, S.S., Bläser, D., Boese, R. et al. Crystal Structures and Packing of 4-Cyanocubanecarboxylic Acid, Its Methyl Ester, and the Solid Solution of 1,4-Dicyanocubane and 1,4-Dibromocubane. Structural Chemistry 12, 259–266 (2001). https://doi.org/10.1023/A:1016672326189
Issue Date:
DOI: https://doi.org/10.1023/A:1016672326189