The title compound, C25H18N4, crystallizes in the centrosymmetric ortho­rhom­bic space group Pbca, with eight mol­ecules in the unit cell. The main feature noticeable in the structure is the impact of the tri­cyano­vinyl (TCV) group in forcing partial planarity of the portion of the mol­ecule carrying the TCV group and directing the mol­ecular packing in the solid state, resulting in the formation of π-stacks of dimers within the unit cell. Short π–π stack closest atom-to-atom distances of 3.444 (15) Å are observed. Such motif patterns are favorable as they are thought to be conducive for better charge transport in organic semiconductors, which results in enhanced device performance. Intra­molecular charge transfer is evident from the shortening in the observed experimental bond lengths. The nitro­gen atoms (of the cyano groups) are involved in extensive short contacts, primarily through C—H⋯NC inter­actions with distances of 2.637 (17) Å.

2024

E80,

12

Nov. 30, 2024

https://journals.iucr.org/e/issues/2024/03/00/nx2005/index.html