Research Article: 2,4-Bis(2-eth­oxy­phen­yl)-7-methyl-3-aza­bicyclo­[3.3.1]nonan-9-one

Date Published: June 01, 2011

Publisher: International Union of Crystallography

Author(s): P. Parthiban, V. Ramkumar, Dong Ho Park, Yeon Tae Jeong.

http://doi.org/10.1107/S1600536811018472

Abstract

The crystal structure of the title compound, C25H31NO3, exists in a twin-chair conformation with an equatorial orientation of the ortho-eth­oxy­phenyl groups. According to Cremer and Pople [Cremer & Pople (1975 ▶), J. Am. Chem. Soc. 97, 1354–1358], both the piperidone and cyclo­hexa­none rings are significantly puckered with total puckering amplitutdes QT of 0.5889 (18) and 0.554 (2) Å, respectively. The ortho-eth­oxy­phenyl groups are located on either side of the secondary amino group and make a dihedral angle of 12.41 (4)° with respect to each other. The methyl group on the cyclo­hexa­none part occupies an exocyclic equatorial disposition. The crystal packing is stabilized by weak van der Waals inter­actions.

Partial Text

For the synthesis and biological activity of 3-aza­bicyclo­[3.3.1]nonan-9-ones, see: Jeyaraman & Avila (1981 ▶); Barker et al. (2005 ▶); Parthiban et al. (2009a ▶, 2010b ▶,c ▶, 2011 ▶). For related structures, see: Parthiban et al. (2009b ▶,c ▶, 2010a ▶,c ▶); Cox et al. (1985 ▶); Smith-Verdier et al. (1983 ▶); Padegimas & Kovacic (1972 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Source:

http://doi.org/10.1107/S1600536811018472