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  • Title: Imino Diels-Alder adducts. XII. Two pyrano[3,2-c]quinolines.
    Author: Ravikumar K, Sridhar B, Mahesh M, Reddy VV.
    Journal: Acta Crystallogr C; 2006 Sep; 62(Pt 9):o574-6. PubMed ID: 16954646.
    Abstract:
    The crystal structures of pyranoquinolines 9-fluoro-5-phenyl-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinoline, C18H18FNO, and 9-methyl-5-phenyl-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinoline, C19H21NO, are isomorphous. In both structures, the pyran ring is exo to the six-membered N-heterocyclic ring formed in the cycloaddition step. The torsion angles across the phenyl linkage for the two structures are -91.2 (1) and -88.3 (2) degrees. The striking feature in both crystal packings is that they do not contain the expected conventional hydrogen bonds, in spite of the presence of good hydrogen-bonding functionalities. Possible C-H...pi interactions are, however, observed.
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