Crystal structure of N,N′-bis[(pyridin-4-yl)methyl]naphthalene diimide

Abstract

In the centrosymmetric title compound, C26H16N4O4 {systematic name: 6,13-bis[(pyridin-4-yl)methyl]-6,13-diazatetracyclo[6.6.2.04,16011,15]hexadeca-1,3,8,10,15-pantaene-5,7,12,14-tetrone}, the central ring system is essentially planar [maximum deviation = 0.0234 (8) Å] and approximately perpendicular to the terminal pyridine ring [dihedral angle = 84.38 (3)°]. The molecules displays a trans conformation with the (pyridin-4-yl)methyl groups on both sides of the central naphthalene diimide plane. In the crystal, molecules are linked by π–π stacking between parallel pyridine rings [centroid–centroid distances = 3.7014 (8) and 3.8553 (8) Å] and weak C—H...O hydrogen bonds, forming a three-dimensional supramolecular architecture.

Keywords

• crystal structure
• naphthalene diimide
• transistors
• organic supramolecular solids
• hydrogen bonding
• π–π stacking