Crystal structure, Hirshfeld surface analysis and DFT calculation of N,N'-(1,4-phenylenebis(methanylylidene))bis(4-fluoroaniline)

Wikorn Punyain

Abstract


In the title Schiff base compound, C20H14F2N2 [systematic name: N,N'-(1,4-phenylenebis(methanylylidene))bis(4-fluoroaniline)] was synthesized by condensation reaction of 1,4-benzenedicarboxaldehyde and 4-fluoroaniline and is found to crystallize in the centrosymmetric monoclinic space group P21/c. The molecular structure of the title compound is not plannar. The dihedral angles between the mean planes of the central benzene ring and the terminal fluorobenzene rings are 51.33 (6) and 52.49 (6)°. In the crystal, the molecules are linked by a combination of types I/II F···F, C–H···F, C–H···N and C–H···π interactions, forming a three-dimensional supramolecular structure. The Hirshfeld surface analysis indicates a high percentage of C···H/H···C (41.1%) contacts in the crystal. The molecular structures are optimized using density functional theory (DFT) at B3LYP/6–311+G(d) level and compared with the experimentally determined in the solid state.  


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