Acta Cryst. (2014). C70, 210-215 [ doi:10.1107/S2053229613034839 ]
Abstract: 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-HO hydrogen bonds links the molecules of (I) into sheets containing a single type of R66(44) ring, and these sheets are linked into a continuous three-dimensional array by a single - stacking interaction. The molecules of (II) are linked into complex sheets by a combination of N-HO, C-HO and C-H(arene) hydrogen bonds.
Formula: C20H19NO3 and C20H21NO3
Keywords: crystal structure; supramolecular structure; hydrogen bonding.
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