Crystal structure of (1RS,21SR,22RS,24SR)-28-oxo-24-propyl-8,11,14-trioxa-24,27-diazapentacyclo[19.5.1.122,26.02,7.015,20]octacosa-2,4,6,15(20),16,18-hexaene acetic acid monosolvate

Abstract

The title compound, C26H32N2O4(M)·C2H4O2, (I), is the product of the Petrenko–Kritchenko condensation ofN-propylpiperidinone with 1,5-bis(2-formylphenoxy)-3-oxapentane and ammonium acetate. InM, the aza-14-crown-3-ether ring adopts a bowl conformation, with the configuration of the C—O—C—C —O—C—C—O—C polyether chain beingt–g(−)–t–t–g(+)–t(t=trans, 180°;g=gauche, ±60°). The dihedral angle between the planes of the benzene rings fused to the aza-14-crown-4-ether moiety is 62.75 (5)°. The central piperidinone ring has a boat conformation, whereas the terminal piperidinone ring adopts a chair conformation. The boat conformation of the central piperidinone ring is supported by the bifurcated intramolecular N—H...O hydrogen bond. In the crystal, each solvent molecule is linked to moleculeM viastrong O—H...N hydrogen bonding, forming hydrogen-bonded pairs of molecules, which further interact through weak C—H...O hydrogen bonds, forming layers parallel to theacplane.