Crystal structure of N,N'-bis-(2,4-di-fluoro-benzo-yloxy)benzene-1,2:4,5-tetra-carboximide.

Sandra Fusco,Angela Tuzi,Roberto Centore,Antonio Carella

doi:10.1107/s2056989018001226

Abstract

Mol-ecules of the title compound, C24H8F4N2O8, have Ci point-group symmetry in the crystal, as they lie on crystallographic inversion centres (Z' = 1/2). The di-fluoro-phenyl ring is disordered over two orientations; the final refined occupancy factors of the two components of disorder are 0.947 (4) and 0.053 (4). In the crystal, some Car-H⋯F inter-actions are present, which involve the most acidic H atom of the mol-ecule.

Highlights

Molecules of the title compound, C24H8F4N2O8, have Ci point-group symmetry in the crystal, as they lie on crystallographic inversion centres (Z0 = 1/2)
In particular, are a class of heterocyclic compounds well known for their outstanding properties as n-type organic semiconductors
The research on n-type organic semiconductors has shown that electron mobilities and device performances can be improved by extensive replacement of H atoms by fluorine (Facchetti et al, 2003)

Summary

Chemical context

Heterocycles are key compounds in synthetic chemistry. In addition to their applications in drugs, bioactive and tautomeric compounds (D’Errico et al, 2012; Piccialli et al, 2007; Centore et al, 2013), aromatic heterocycles play an important role in modern materials chemistry, because they are used as building blocks of active molecules in many emerging fields of advanced materials, for example, conducting polymers (Heeger, 2010), organic field-effect transistors (Miao, 2014), organic solar cells (Nielsen et al, 2015), liquid crystals (Centore et al, 1996) and nonlinear optically active compounds (Carella et al, 2007; Centore et al, 1999). The research on n-type organic semiconductors has shown that electron mobilities and device performances can be improved by extensive replacement of H atoms by fluorine (Facchetti et al, 2003). Following these issues, we report here the structural investigation of the title compound, N,N0-bis(2,4-difluorobenzoyloxy)benzene-1,2:4,5-tetracarboximide, which is a fluorinated derivative of the simplest aromatic bis(imide). The C6—O3 bond length [1.402 (3) A ] is significantly longer than the mean value for esters of aromatic acids (1.337 A ; Allen et al, 1987). This, in turn, can be due to the presence of the electronegative N atom bonded to O3

Supramolecular features

Database survey

Synthesis and crystallization

Refinement