Abstract
During crystallization 1,3-cyclohexanedione self assembles into either hydrogen-bonded chains or hexameric rings depending on the solvent conditions. The hexameric rings, called cyclamers, are the subject of this paper. These unusual structures occlude benzene as a guest molecule. The structural and crystal chemical properties of these host-guest compounds are explored here with the use of crystal growth studies, X-ray powder patterns, and thermal analysis. The crystal structure of the benzene cyclamer of 5-methyl-1,3-cyclohexanedione is reported (hexagonal,a =b = 19.19(2)Å,c = 10.545(9)Å,R3,Z = 18,V = 3362(6)Å3; 717 unique reflections,R = 0.062). An analysis of the stereochemical implications of cyclic directionality in these cyclamers is also discussed.
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Alfred P. Sloan Foundation Fellow, 1989–1991.
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Etter, M.C., Parker, D.L., Ruberu, S.R. et al. Solid-state and inclusion properties of hydrogen-bonded 1,3-cyclohexanedione cyclamers. J Incl Phenom Macrocycl Chem 8, 395–407 (1990). https://doi.org/10.1007/BF01041196
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DOI: https://doi.org/10.1007/BF01041196