Date Published: June 01, 2011
Publisher: International Union of Crystallography
Author(s): Volodymyr V. Nesterov, Sergey S. Sarkisov, Vladimir Shulaev, Vladimir N. Nesterov.
The title compound, C26H21Cl2NO, crystallizes with two symmetry-independent molecules (A and B) in the asymmetric unit. In both molecules, the central heterocyclic ring adopts a sofa conformation. The dihedral angles between the planar part of this central heterocyclic ring [maximum deviations of 0.011 (1) and 0.036 (1) Å in molecules A and B, respectively] and the two almost planar [maximum deviations of 0.020 (1) and 0.008 (1) Å in A and 0.007 (1) and 0.011 (1) in B] side-chain fragments that include the aromatic ring and bridging atoms are 20.1 (1) and 31.2 (1)° in molecule A, and 26.4 (1) and 19.6 (1)° in molecule B. The dihedral angles between the planar part of the heterocyclic ring and the benzyl substituent are 79.7 (1) and 53.2 (1)° in molecules A and B, respectively. In the crystal, weak intermolecular C—H⋯O hydrogen bonds link the two independent molecules into dimers.
For non-linear optical organic compounds with two-photon absorption properties and potential biophotonic materials, see: Nesterov et al. (2003 ▶, 2007 ▶); Sarkisov et al. (2005 ▶). For the biological importance of 4-piperidone, see: Jia et al. (1988 ▶); Dimmock et al. (2001 ▶). For the synthesis of the title compound, see: Dimmock et al. (2001 ▶). For related structures, see: Nesterov et al. (2003 ▶, 2007 ▶, 2011 ▶). For details concerning weak hydrogen bonds, see: Desiraju & Steiner (1999 ▶). For van der Waals radii, see: Rowland & Taylor (1996 ▶).