Garay Alexander, Abonía Rodrigo, Cobo Justo, Glidewell Christopher
Departamento de Química, Universidad de Valle, AA 25360 Cali, Colombia.
Departamento de Química Inorgánica y Orgánica, Universidad de Jaén, 23071 Jaén, Spain.
Acta Crystallogr C Struct Chem. 2014 Feb;70(Pt 2):210-5. doi: 10.1107/S2053229613034839. Epub 2014 Jan 11.
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.
