Received 9 March 2013
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 interactions leads to inversion dimers.
For palladium-catalysed intermolecular and intramolecular reactions, see: Zhao et al. (2012) and for palladium-catalysed coupling reactions, see: Meng et al. (2011); Hu et al. (2011). They have made a wide variety active pharmaceutical ingredients and complex organic molecules economically accessible, see: Hu et al. (2009, 2010). For the physiological activity of benzo[f]isoindol-1-one derivatives, see: Pitchumani & Vijaikumar (2010).
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BV2220 ).
We thank the National Science Foundation of China (project Nos. 21272005 and 21072003) for financial support for this work.
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