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Comparison of N ‐(3,4,5‐trimethoxybenzylidene)naphthalen‐1‐amine and its reduction product N ‐(3,4,5‐trimethoxybenzyl)naphthalen‐1‐amine
Author(s) -
Garay Alexander,
Abonía Rodrigo,
Cobo Justo,
Glidewell Christopher
Publication year - 2014
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229613034839
Subject(s) - amine gas treating , chemistry , hydrogen bond , molecule , stacking , crystallography , enantiomer , ring (chemistry) , stereochemistry , crystal structure , organic chemistry
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.