Mol­ecular and crystal structure of 2,5-bis­[(4-fluoro­phen­yl)imino­meth­yl]furan

In the reported crystal structure, the central furan ring lies on a twofold rotation axis in space group C2/c with the furan ring and imine groups of adjacent mol­ecules participating in C—H⋯N inter­actions to give furan-ring-centered hydrogen-bonded chains extending along [010].

The title furan bis­(imine) compound, 2,5-bis­[(4-fluoro­phen­yl)imino­meth­yl]furan, C₁₈H₁₂F₂N₂O, was synthesized by condensation of 2,5-furan­dicarboxaldehyde with two equivalents of 4-fluoro­aniline. The mol­ecular structure consists of a central furan ring symmetrically bound to nearly coplanar imino­methyl groups with N-bonded 4-fluoro­phenyl rings that are significantly tipped out of the plane of the furan ring. In the crystal structure, the furan ring lies on a twofold rotation axis in space group C2/c with the furan ring and imine groups of adjacent mol­ecules participating in C—H⋯N inter­actions to give furan-ring-centered hydrogen-bonded chains extending along [010]. Further cohesion of the crystal structure is achieved by participation of the peripheral 4-fluoro­phenyl rings in C—H⋯F hydrogen bonding and edge-to-face C—H⋯π inter­actions, resulting in a tri-periodic network. The resulting supra­molecular chains formed by C—H⋯F hydrogen bonding extend in a direction parallel to [101].