Preparation of donor–acceptor substituted fluorostilbenes and crystal chemistry of fluorinated (E)-4-(4-halogeno-styryl)-benzonitriles

The syntheses and crystal structures of a series of fluoro-substituted halogeno (Cl, Br, I)-cyano-stilbenes containing donor and acceptor groups (D-π-A) are reported. These molecules show a tendency to form antiparallel chain-like structures and herringbone packing, crystallising predominantly in a centric space group. However, second harmonic generation measurements bear evidence for orientational disorder leading to partial polar order below the ordinary X-ray structure determination limit. Some co-crystals are isostructural with their components. The non-fluoro as well as the halogeno-fluoro substituted components of co-crystals seem to impose their crystal structure on the complementary fluoro- or cyano–fluoro substituted components. Co-crystallization enhanced the deviation from centrosymmetry.