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.
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 ▶).