Date Published: August 01, 2012
Publisher: International Union of Crystallography
Author(s): Truong Hong Hieu, Le Tuan Anh, Anatoly T. Soldatenkov, Nadezhda M. Kolyadina, Victor N. Khrustalev.
The title compound, C31H34N2O9, is a product of the Michael addition of the cyclic secondary amine subunit of the (bispidino)aza-14-crown-4 ether to dimethyl acetylenedicarboxylate. The molecule comprises a tricyclic system containing the aza-14-crown-3 ether macrocycle and two six-membered piperidinone rings. The aza-14-crown-3-ether ring adopts a bowl conformation with a dihedral angle between the planes of the fused benzene rings of 51.14 (5)°. The central piperidone ring has a boat conformation, whereas the terminal piperidone ring adopts a chair conformation. The dimethyl ethylenedicarboxylate fragment has a cis configuration with a dihedral angle of 56.56 (7)° between the two carboxylate groups. The crystal packing is stabilized by weak C—H⋯O hydrogen bonds.
For general background, see: Hiraoka (1982 ▶); Pedersen (1988 ▶); Schwan & Warkentin (1988 ▶); Gokel & Murillo (1996 ▶); Bradshaw & Izatt (1997 ▶). For related compounds, see: Levov et al. (2006 ▶, 2008 ▶); Komarova et al. (2008 ▶); Anh et al. (2008 ▶); Anh, Hieu, Soldatenkov, Kolyadina & Khrustalev (2012a ▶,b ▶); Anh, Hieu, Soldatenkov, Soldatova & Khrustalev (2012 ▶); Hieu et al. (2011 ▶); Khieu et al. (2011 ▶); Sokol et al. (2011 ▶).