Synthesis by deamination reaction and crystal structure at 120 K of (16 Z,19 E)-18-oxo- N -(pyridin-2-yl)-6,7,9,10-tetra­hydro-18 H -dibenzo[ h, o ][1,4,7]trioxa­cyclo­hexa­decine-17-carboxamide

The title compound, C 27 H 24 N 2 O 5, is a product of the deamination reaction from aza-14-crown-4 ether containing the γ-piperidone subunit. The title mol­ecule contains a 16-membered macrocycle with the conformation 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 31.11 (14)°. The cavity size inside the macrocycle is 4.72 Å. The macrocycle is significantly flattened as a result of the extended conjugated system. Steric repulsion between the pyridyl­carboxamide fragment and the benzene ring results in a slight deviation of macrocycle from planarity. The structure also features intra­molecular hydrogen bonding, which results in a deviation of the angle between the planes of amide and pyridyl groups from planarity: this angle is 16.32 (18)°. In the crystal, the mol­ecules are linked into infinite zigzag chains via inter­molecular C - H⋯π contacts. The chains are bound into layers parallel to (100) by weak inter­molecular C - H⋯O hydrogen bonds. © 2020 International Union of Crystallography. All rights reserved.