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

The title furan bis-(imine) compound, 2,5-bis-[(4-fluoro-phen-yl)imino-meth-yl]furan, C₁₈H₁₂F₂N₂O, was synthesized by condensation of 2,5-furan-dicarboxaldehyde with two equivalents of 4-fluoro-aniline. The mol-ecular structure consists of a central furan ring symmetrically bound to nearly coplanar imino-methyl groups with N-bonded 4-fluoro-phenyl 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 <i>C</i>2/<i>c</i> with the furan ring and imine groups of adjacent mol-ecules participating in C-H⋯N inter-actions 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-fluoro-phenyl rings in C-H⋯F hydrogen bonding and edge-to-face C-H⋯π inter-actions, resulting in a tri-periodic network. The resulting supra-molecular chains formed by C-H⋯F hydrogen bonding extend in a direction parallel to [101].