Research Article: Dimethyl 2-[23-oxo-22,24-diphenyl-8,11,14-trioxa-25-aza­tetra­cyclo­[,7.015,20]penta­cosa-2,4,6,15(20),16,18-hexaen-25-yl]but-2-enedioate

Date Published: May 01, 2012

Publisher: International Union of Crystallography

Author(s): Le Tuan Anh, Truong Hong Hieu, Anatoly T. Soldatenkov, Svetlana A. Soldatova, Victor N. Khrustalev.


The title compound, C39H37NO8, is a product of the Michael addition of the cyclic secondary amine subunit of aza-14-crown-4 ether to dimethyl acetyl­enedicarboxyl­ate. The piperidinone ring exhibits a distorted chair conformation and the dimethyl acetyl­enedicarboxyl­ate fragment has a cis configuration with a dihedral angle of 56.61 (5)° between the two carboxyl­ate groups. The crystal packing is stabilized by the weak C—H⋯O hydrogen bonds.

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For general background to the design, synthesis, chemical properties and applications of macrocyclic ligands in coordination chemistry, see: Hiraoka (1978 ▶); Pedersen (1988 ▶); Schwan & Warkentin (1988 ▶); Gokel & Murillo (1996 ▶); Bradshaw & Izatt (1997 ▶). For related compounds, see: Levov et al. (2006 ▶, 2008 ▶); Anh et al. (2008 ▶); Hieu et al. (2011 ▶); Khieu et al. (2011 ▶).