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The title compound is the product of the Chichibabin domino reaction of 1,8-bis­(2-acetyl­phen­oxy)-3,6-dioxa­octane with 4-methyl­benzaldehyde and ammonium acetate in acetic acid. It is of inter­est with respect to its potential anti­cancer activity. The compound has a bowl-like conformation comprising a fused tetra­cyclic system containing a 4-aryl­pyridine fragment, two benzene rings and an aza-17-crown-5 ether moiety.

Macrocyclic 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 obtained by a Petrenko–Kritchenko condensation of 1,5-bis­(2-formyl­phen­oxy)-3-oxa­pentane, pentan-3-one and methyl­ammonium acetate has been studied by X-ray structural analysis.

The title compound, C21H23NO4S, obtained by alkaline treatment of 1,5-bis(1-phenoxy)-3-azapentane at moderate heating, is a N-tosylated secondary vinylamine. An intramolecular S=O...H—C hydrogen bond generates a 13-membered ring. The benzalacetone moiety adopts a trans conformation with respect to the C=C double bond, which is slightly longer than usual due to the conjugation with a neighbouring acetyl group. Theoretical predictions of potential biological activities were performed, suggesting that the title compound can inhibit gluconate 2-dehydrogenase (85% probability), as well as to act as a mucomembranous protector (73%).