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 of N-propylpiperidinone with 1,5-bis(2-formylphenoxy)-3-oxapentane and ammonium acetate. In M, 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 being t–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 molecule M via strong 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 the ac plane.

Keywords

• crystal structure
• Petrenko–Kritchenko condensation
• aza-14-crown-3-ether