Date Published: June 01, 2011
Publisher: International Union of Crystallography
Author(s): P. Parthiban, V. Ramkumar, Dong Ho Park, Yeon Tae Jeong.
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.
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 ▶).