Crystal structure of 22,24,25-trimethyl-8,11,14-trioxa-25-azatetracyclo[19.3.1.02,7.015,20]pentacosa-2,4,6,15(20),16,18-hexaen-23-one

Abstract

The title compound, C24H29NO4, is the product of a Petrenko–Kritchenko condensation of 1,5-bis(2-formylphenoxy)-3-oxapentane, pentan-3-one and methylammonium acetate in ethanol. The molecule has mirror symmetry. The aza-14-crown-3 ether ring adopts a bowl conformation stabilized by a weak intramolecular C—H...O hydrogen bond. The conformation of the C—O—C—C—O—C—C—O—C polyether chain is t–g+–t–t–g−–t (t = trans, 180°; g = gauche, ±60°). The dihedral angle between the benzene rings fused to the aza-14-crown-4-ether moiety is 72.68 (4)°. The piperidinone ring adopts a chair conformation. The nitrogen atom has a trigonal–pyramidal geometry, the sum of the bond angles being 335.9°. In the crystal, the molecules are linked by weak C—H...O interactions, forming zigzag chains propagating along the [100] direction.

Keywords

• crystal structure
• macroheterocycles
• crown ethers
• stacking interactions