Weak non-covalent interactions control the relative molecular orientation in the crystals of N-pentafluorobenzyl aniline derivatives

The crystal structures of N-pentafluorobenzyl aniline derivatives are controlled by versatile aromatic–aromatic interactions between the electron deficient and electron rich aromatics; the parent compound (1) possesses an L shape while protonation (2–5) induces a conformational change resulting in a planar arrangement of molecules which pack in layer type structures with different molecular orientations.