2,2'-{2-[(E)-3-Phenylprop-2-enyl]-2,3-dihydro-1H-isoindol-1,3-diylidene}dimalononitrile, a π-deficient system for π...π (1:1) stacking investigations

Abstract

The title compound, C₂₃H₁₃N₅, derived from cinnamyl alcohol and 2,2'-(isoindolin-1,3-diylidene)bispropanedinitrile, is a heterocyclic TCNQ analogue of interest as an electron-deficient component in charge-transfer complexes. A small perturbation of the four C-C≡N angles from linearity is observed, which are in the range 173.41 (18)-176.3 (2)°; the C≡N bond lengths are in the range 1.144 (2)-1.146 (2) Å. The terminal phenyl group is oriented at an angle of 77.17 (6)° to the C₄N ring and the C=C bond is short, 1.319 (2) Å. There are no classical hydrogen bonds, although intramolecular C-H...N and intermolecular C-H...π(arene) interactions influence the crystal-structure packing.