Date Published: July 01, 2012
Publisher: International Union of Crystallography
Author(s): Le Tuan Anh, Truong Hong Hieu, Anatoly T. Soldatenkov, Nadezhda M. Kolyadina, Victor N. Khrustalev.
The title compound, C25H28N2O5, is a product of the Petrenko–Kritchenko condensation of N-acetylpiperidone with 1,5-bis(2-formylphenoxy)-3-oxapentane and ammonium acetate. The molecule comprises a fused pentacyclic system containing an aza-14-crown-3-ether macrocycle, two piperidone and two benzene rings. The aza-14-crown-3-ether ring adopts a bowl conformation. The dihedral angle between the benzene rings fused to the aza-14-crown-4-ether unit is 70.18 (4)°. The central piperidone ring has a boat conformation, whereas the terminal piperidone ring adopts a chair conformation. The conformation of the central piperidone ring is determined by two intramolecular N—H⋯O hydrogen bonds. In the crystal, molecules are linked by weak C—H⋯O interactions into chains along .
For general background to the design, synthesis and applications of macrocyclic ligands for coordination and supramolecular chemistry, see: Hiraoka (1978 ▶); Pedersen (1988 ▶); Gokel & Murillo (1996 ▶); Bradshaw & Izatt (1997 ▶). For related compounds, see: Levov et al. (2006 ▶, 2008 ▶); Komarova et al. (2008 ▶); Anh et al. (2008 ▶, 2012a ▶,b ▶); Hieu et al. (2011 ▶); Khieu et al. (2011 ▶); Sokol et al. (2011 ▶).