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

Abstract

The title compound, C27H24N2O5, 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.

Keywords

• deamination reaction
• aza-crown ether
• dibenzo-16-crown-3
• crystal structure
• γ-piperidone
• hydrogen bonds
• c—h...π contacts