Research Article: (2S,5S,6R)-5-(4-Methyl­phen­yl)-3-phenyl-4,8-dioxa-3-aza­tricyclo­[,6]trideca-1(13),9,11-triene-6-carbonitrile

Date Published: February 01, 2012

Publisher: International Union of Crystallography

Author(s): K. Swaminathan, K. Sethusankar, J. Srinivasan, M. Bakthadoss.


In the title compound, C24H20N2O2, the six-membered pyran ring adopts a half-chair conformation with one C atom deviating from the mean plane of the remaining ring atoms by 0.654 (6) Å. The five-membered isoxazole ring adopts an N-envelope conformation with the N atom displaced by 0.742 (5) Å from the mean plane formed by the remaining ring atoms. The carbonitrile side chain is almost linear, with a C—C—N angle of 178.6 (5)°. The crystal packing is stabilized by inter­molecular C—H⋯N inter­actions, through bifurcated acceptor hydrogen bonds formed between the carbonitrile N atom and two alternate C atoms in the unsubstituted benzene ring. The mol­ecular structure and crystal packing are further stabilized by intra­molecular and inter­molecular C—H⋯π inter­actions.

Partial Text

For uses of benzopyran and isoxazolidine derivatives, see: Green et al. (1982 ▶); Kashiwada et al. (2001 ▶); Mullen et al. (1988 ▶). For a related structure, see: Swaminathan et al. (2011 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For synthetic details, see: Bakthadoss & Murugan (2010 ▶).