Research Article: 3,5-Bis(4-chloro­benzyl­idene)-1-methyl­piperidin-4-one

Date Published: April 01, 2011

Publisher: International Union of Crystallography

Author(s): Volodymyr V. Nesterov, Sergey S. Sarkisov, Vladimir Shulaev, Vladimir N. Nesterov.


In the title mol­ecule, C20H17Cl2NO, the central heterocyclic ring adopts a flattened boat conformation. The dihedral angles between the planar part of this central heterocyclic ring [maximum deviation = 0.004 (1) Å] and the two almost planar side-chain fragments [maximum deviations = 0.015 (1) and 0.019 (1) Å], that include the aromatic ring and bridging atoms, are 18.1 (1) and 18.0 (1)°. In the crystal, pairs of weak inter­molecular C—H⋯O hydrogen bonds link mol­ecules into inversion dimers that form stacks along the a axis. The structure is further stabilized by weak inter­molecular C—H⋯π inter­actions involving the benzene rings.

Partial Text

For non-linear optical organic compounds with two-photon absorption properties and potential biophotonic materials, see: Nesterov et al. (2003 ▶); Nesterov (2004 ▶); Sarkisov et al. (2005 ▶). For the biological importance of 4-piperidone, see: Jia et al. (1988 ▶, 1989 ▶); Dimmock et al. (2001 ▶). For the synthesis of the title compound, see: Dimmock et al. (2001 ▶). For related structures, see: Nesterov (2004 ▶); Nesterov et al. (2003 ▶, 2007a ▶,b ▶,c ▶, 2008 ▶). For weak hydrogen bonds, see: Desiraju & Steiner (1999 ▶). For the van der Waals radius of the H atom, see: Rowland & Taylor (1996 ▶).




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