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, C 20 H 19 NO 3 , (I), and its reduction product N ‐(3,4,5‐trimethoxybenzyl)naphthalen‐1‐amine, C 20 H 21 NO 3 , (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.