The title compound, C27H24N2O5, is a product of the deamination reaction from aza-14-crown-4 ether containing the γ-piperidone subunit. The title mol-ecule 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 pyridyl-carboxamide fragment and the benzene ring results in a slight deviation of macrocycle from planarity. The structure also features intra-molecular 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 mol-ecules are linked into infinite zigzag chains via inter-molecular C-H⋯π contacts. The chains are bound into layers parallel to (100) by weak inter-molecular C-H⋯O hydrogen bonds.
Keywords: C—H⋯π contacts; aza-crown ether; crystal structure; deamination reaction; dibenzo-16-crown-3; hydrogen bonds; γ-piperidone.
© Wodajo et al. 2020.