Research Article: (R,E)-3-(4-Chloro­phen­yl)-1-phenyl­allyl 4-nitro­benzoate

Date Published: August 01, 2012

Publisher: International Union of Crystallography

Author(s): Konstantin Troshin, Peter Mayer, Herbert Mayr.


The title compound, C22H16ClNO4, adopts a conformation in which the phenyl ring plane forms similar dihedral angles with the nitro­benzoate C6 ring [76.97 (8)°] and the chloro­phenyl group [76.95 (8)°]; the dihedral angle between the chloro­phenyl and nitro­benzoate rings is 66.43 (8)°. In the crystal, π–π stacking is observed between the latter two planes, with a dihedral angle of 1.79 (8)° and a centroid–centroid distance of 3.735 (1) Å. In addition, mol­ecules are linked along [100] by weak C—H⋯O contacts.

Partial Text

For background to the stereochemistry of allylic rearrangements, see: Hughes (1941 ▶); Raber et al. (1974 ▶); Goering et al. (1971 ▶). For details of the synthesis, see: Troshin et al. (2011 ▶); Gao et al. (1987 ▶); Roos & Donovan (1996 ▶). For related structures, see: Cao et al. (2011 ▶); Wang et al. (2009 ▶).




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