Abstract
In the title compound, C25H30NO3, a crystallographic mirror plane bisects the molecule. Although it is a positional isomer of 2,4-bis(4-ethoxyphenyl)-7-methyl-3-azabicyclo[3.3.1]nonan-9-one [C25H31NO3, M r = 393.51; Park et al. (2012c ▶). Acta Cryst. E68, o779–780], its molecular weight is 392.50 due to the 50:50 ratio of the methyl group at bridgehead C atoms. However, the title compound exists in the same twin-chair conformation as its 7-methyl isomer. Also, the 4-ethoxyphenyl groups are equatorially oriented on the bicycle as in its isomer. In the title compound, the cyclohexanone ring deviates from an ideal chair (total puckering amplitude Q T = 0.5390 Å) and the piperidone ring is closer to an ideal chair (Q T = 0.6064 Å). These Q T values are very similar to those of its isomer. Even though a center of symmetry passes through the 7-methyl analog, the benzene rings are oriented 26.11 (3)° with respect to each other, whereas the orientation is 53.10 (3)° for the title compound. The title compound exhibits intermolecular N—H⋯O interactions [H⋯A = 2.25 (2) Å, versus 2.26 (2) Å for the analog].
Highlights
In the title compound, C25H30NO3, a crystallographic mirror plane bisects the molecule
The title compound exists in the same twin-chair conformation as its 7-methyl isomer
The 4-ethoxyphenyl groups are equatorially oriented on the bicycle as in its isomer
Summary
C25H30NO3, a crystallographic mirror plane bisects the molecule It is a positional isomer of 2,4-bis(4-ethoxyphenyl)-7-methyl-3-azabicyclo[3.3.1]nonan-9-one [C25H31NO3, Mr = 393.51; Park et al (2012c). The cyclohexanone ring deviates from an ideal chair (total puckering amplitude QT = 0.5390 Å) and the piperidone ring is closer to an ideal chair (QT = 0.6064 Å). These QT values are very similar to those of its isomer. Even though a center of symmetry passes through the 7-methyl analog, the benzene rings are oriented 26.11 (3) with respect to each other, whereas the orientation is 53.10 (3) for the title compound. Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2375)
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