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

The molecules of the 7-chloroquinoline-4-hydrazones of the variously substituted benzaldehydes, 5 , of general formula C 16 H 11 ClN 3 X 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).