Comparison of N-(3,4,5-trimethoxybenzylidene)naphthalen-1-amine and its reduction product N-(3,4,5-trimethoxybenzyl)naphthalen-1-amine.

The molecules in (E)-N-(3,4,5-trimethoxybenzylidene)naphthalen-1-amine, C20H19NO3, (I), and its reduction product N-(3,4,5-trimethoxybenzyl)naphthalen-1-amine, C20H21NO3, (II), are both conformationally chiral, but (I) crystallizes in a centrosymmetric space group, while (II) crystallizes with just one conformational enantiomer in each crystal. A combination of two C-H···O hydrogen bonds links the molecules of (I) into sheets containing a single type of R(6)(6)(44) ring, and these sheets are linked into a continuous three-dimensional array by a single π-π stacking interaction. The molecules of (II) are linked into complex sheets by a combination of N-H···O, C-H···O and C-H···π(arene) hydrogen bonds.