Structures of arylaldehyde 7-chloroquinoline-4-hydrazones:supramolecular arrangements derived from N H•••N, C H••• X ( X = N, O, or π) and π•••π interactions

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Abstract

The molecules of the 7-chloroquinoline-4-hydrazones of the variously substituted benzaldehydes, 5, of general formula C₁₆H₁₁ClN₃X with X = H, o-F, m-F or m-MeO corresponding to compounds (5: X = H), (5: X = o-F), (5: X = m-F)and(5: X = m-MeO), respectively, are formally rather similar. Compounds (5: X = H) and(5: X = o-F) are isostructural but otherwise the molecular packing and intermolecular interactions show unexpectedly wide variation throughout the series. In all 5 hydrogen-bonds link the essentially planar molecules edge to edge to form chains. Combination of intermolecular hydrogen-bonds and π···π interactions creates three-dimensional connectivity in (5: X = H), (5: X = o-F) and, utilising the methoxy oxygen atom as acceptor for a C—H···O hydrogen-bond, (5: X = m-MeO). Significant connectivity is no more than two-dimensional in layers of molecules in (5: X = m-F).

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Keywords: X-ray diffraction; Single crystal structure analysis; 7-chloroquinoline-4-hydrazone; pi…pi interactions; Hydrogen bonds Document Type: Research Article DOI: http://dx.doi.org/10.1524/zkri.2010.1291 Publication date: 1 de Agosto de 2010