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A crystal structure determination confirmed that the product from 7-chloroquinilin-4-ylhydrazine and 4-methoxycinnanamic acid had been isolated from MeOCH 2 CH 2 OH solution as [( E )- N′- 7-chloro-4-(4-methoxycinnamolyhydrazinyl)quinoline,  1 . In contrast, recrystallization of the 2-MeO derivative,  2 , from the same solvent, produced a 1 : 1 co-crystalline mixture of two tautomers, namely ( E )- N′- 7-chloro-4-(2-methoxycinnaämolyhydrazinyl)quinoline and 7-chloro-4(1 H)quinolinone 3-(2-methoxycinnamoyl)hydrazone, molecules  A  and  B , respectively. Molecules  1  and  2A  have “ L ”-shapes and, in general, have very similar conformations, which differ from that of  2B , mainly arising from the rotation about the (O)C—N(N) bond within the linker unit between the quinolone and methoxyphenyl rings. In both  1  and  2 , the 3-dimensional supramolecular arrangements involve strong N—H…N, N—H…O, C—H…O and C—H…π hydrogen bonds, while additionally in  2 , there are π…π, C—Cl…π and C—H…Cl intermolecular interactions.

Structures of a co-crystal of tautomers of ( E )-N-7-chloro-4-(2-methoxycinnamolyhydrazinyl)quinoline and a single tautomer of the 4-methoxy analogue