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The title compound, C 30 H 34 N 2 O 9 ( 4 ), is a product of the Michael reaction of aza-crown ether with dimethyl acetyl-enedi-carboxyl-ate modified by an addition of NH 3 (aq.) at 298 K. The aza-14-crown-4-ether ring adopts a bowl conformation. The dihedral angle between the planes of the benzene rings fused to the aza-14-crown-4-ether moiety is 8.65 (5)°. The tetra-hydro-pyridine ring has a boat conformation. The mol-ecular conformation is supported by one N-H⋯O and two C-H⋯O intra-molecular hydrogen bonds. Both heterocyclic and amino N atoms have essentially planar configurations (sums of the bond angles are 359.35 and 358.00°). Compound 4 crystallizes as a racemate consisting of enanti-omeric pairs of the 1 R ,21 S diastereomer. In the crystal, mol-ecules of 4 are connected by N-H⋯O hydrogen bonds, forming chains along [100]. According to the PASS program (computer prediction of biological activities), compound 4 may exhibit anti-allergic (72% probability) and anti-asthmatic (67%) activity, as well as be a membrane permeability inhibitor (65%).

acta crystallographica. section e, crystallographic communications

One-pot synthesis of (1RS,21SR)-diethyl 2-[23-amino-22-ethoxycarbonyl-8,11,14-trioxa-25-azatetracyclo[19.3.1.02,7.015,20]pentacosa-2,4,6,15(20),16,18,22-heptaen-25-yl]but-2-endioate