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The solid‐state structures of three push–pull acceptor‐π‐donor (A‐π‐D) systems differing only in the nature of the π‐spacer have been determined. (E)‐1‐Nitro‐4‐[2‐(3,4,5‐trimethoxyphenyl)ethenyl]benzene, C17H17NO5, (I), and its `bridge‐flipped' imine analogues, (E)‐3,4,5‐trimethoxy‐N‐(4‐nitrobenzylidene)aniline, C16H16N2O5, (II), and (E)‐4‐nitro‐N‐(3,4,5‐trimethoxybenzylidene)aniline, C16H16N2O5, (III), display different kinds of supramolecular networks, viz. corrugated planes, a herringbone pattern and a layered structure, respectively, all with zero overall dipole moments. Only (III) crystallizes in a noncentrosymmetric space group (P212121) and is, therefore, a potential material for second‐harmonic generation (SHG).
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Document Type: Research Article

Affiliations: Department of Chemistry, University of Antwerp, Universiteitsplein 1, B-2610 Antwerp, Belgium

Publication date: September 15, 2011

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