Supramolecular architectures in the crystal structures of six chromone derivatives: Hirshfeld surface and energy framework analyses.

Abstract

The synthesis and characterization of six novel chromone hydrazide derivatives are described, namely, (E)-2,4-dichloro-N'-[(4-oxo-4H-chromen-3-yl)methylidene]benzohydrazide monohydrate, C₁₇H₁₀Cl₂N₂O₃·H₂O, (I), (E)-4-chloro-N'-[(4-oxo-4H-chromen-3-yl)methylidene]benzohydrazide hemihydrate, C₁₇H₁₁ClN₂O₃·0.5H₂O, (II), (E)-2-methoxy-N'-[(4-oxo-4H-chromen-3-yl)methylidene]benzohydrazide monohydrate, C₁₈H₁₄N₂O₄·H₂O, (III), tert-butyl (E)-2-[(4-oxo-4H-chromen-3-yl)methylidene]hydrazine-1-carboxylate, C₁₅H₁₆N₂O₄, (IV), tert-butyl (E)-2-[(2-amino-4-oxo-4H-chromen-3-yl)methylidene]hydrazine-1-carboxylate, C₁₅H₁₇N₃O₄, (V), and (E)-N'-[(4-oxo-4H-chromen-3-yl)methylidene]acetohydrazide, C₁₂H₁₀N₂O₃, (VI). Compounds (I)-(III) crystallize as hydrates, with water molecules playing a significant role in the hydrogen-bonding networks. The studied compounds exhibit diverse supramolecular architectures driven by various types of hydrogen bonds (N-H...O, O-H...O and O-H...N), weak C-H...O contacts and aromatic π-π stacking interactions. Energy frameworks, illustrating the distribution of the total energy and dispersive energy contributions, predominantly reveal di-periodic patterns that reflect the layered crystal structures. However, in compounds (I) and (III), tri-periodic motifs appear, primarily influenced by dispersive interactions.