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 center dot center dot center dot 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 pi-pi stacking interaction. The molecules of (II) are linked into complex sheets by a combination of N-H center dot center dot center dot O, C-H center dot center dot center dot O and C-H center dot center dot center dot pi(arene) hydrogen bonds.