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Crystal structures, NMR and IR spectra and EI-MS +  of 2-hydroxyacetophenone arylhydrazones, 2-HOC 6 H 4 C(Me) = NNHC 6 H 4 Y ( 1 : Y = 2-O 2 N, 3-O 2 N, 4-O 2 N, 4-Me, 4-MeO, H and 4-I) are reported. Two polymorphs of ( 1 : Y = 2-O 2 N), triclinic and orthorhombic forms, have been identified. While strong intramolecular O–H · · · N(H) hydrogen bonds and layers of molecules are found for all solid  1 , supramolecular arrangements of individual members are various and are derived from different combinations of intermolecular interactions, which include C–H · · · O(H), C–H · · · O(NO), N–H · · · O(H), N–H · · · O(NO) and C–H · · · π hydrogen bonds, as well as π · · · π stacking interactions. Intermolecular N–H · · · O hydrogen-bonds involving the phenolic OH group are present in ( 1 : Y = H, 4-O 2 N, 4-Me, 4-MeO and 4-I), but are absent in  ortho- and  tri -( 1 : Y = 2-O 2 N) and ( 1 : Y = 3-O 2 N). Instead,  ortho -( 1 : Y = 2-O 2 N) exhibits intermolecular C–H · · · O(H) hydrogen bonds, while no intermolecular hydrogen bonds involving the OH group occur in either  triclinic -( 1 : Y = 2-O 2 N) or ( 1 : Y = 3-O 2 N). EI + -MS revealed the presence of oligomeric species, such as (nM + M′) + , where n is up to 4, and M′ = H, Na or K.

zeitschrift für kristallographie

2-Hydroxyacetophenone arylhydrazones. Supramolecular arrangements based on C–H · · · O(H), CH · · · O(NO), N–H · · · O(H), N–H · · · O(NO), C–H · · · π or π · · · π interactions