[Open access]

[Contents scheme]

Acta Cryst. (2013). E69, o926
[ doi:10.1107/S1600536813011045 ]

2-Tosyl-2,3,3a,4,9,9a-hexahydro-1H-benzo[f]isoindol-1-one

M. Wu and Y.-M. Hu

Abstract: The title compound, C19H19NO3S, was produced by the self-reaction of N-cinnamyl-N-tosylacrylamide in the presence of palladium(II) acetate via an intramolecular C-C coupling reaction and C-H activation. There are two chiral C atoms in the molecule, but the crystal is a racemic system due to a lack of chiral separation. The five-membered ring is twisted about the methylene-methane bond, and the cyclohexa-1,4-diene ring has a boat conformation. The dihedral angle between the benzene rings is 88.27 (14)°, indicating an almost orthogonal relationship and an approximate L-shape for the molecule. In the crystal, the presence of C-H...[pi] interactions leads to inversion dimers.


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