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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.

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—Hπ contacts. The chains are bound into layers parallel to (100) by weak inter­molecular C—HO hydrogen bonds. [ABSTRACT FROM AUTHOR]

Six novel phane-structured diazacrowns containing γ-piperidone and pyridine rings were synthesized from podand 2-+,6-bis(2-formylphenoxymethyl)pyridine, with the γ-piperidone moiety having been constructed in the course of its domino condensation with simple ketones and ammonium acetate. The compounds were tested in vitro for antimicrobial and cytotoxic activity against four human cancer cell lines (Hep-G2, RD, MCF-7, Lu-1) and the Vero cell line. X-Ray structure study of one representative compound revealed its rac -1 RS ,23 SR ,24 RS ,26 SR configuration. [ABSTRACT FROM AUTHOR]