Research Article: 24-Acetyl-8,11,14-trioxa-24,27-diaza­penta­cyclo­[,26.02,7.015,20]octa­cosa-2,4,6,15(20),16,18-hexaen-28-one

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 [010].

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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 ▶).




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