Received 29 October 2012
In the title compound, C10H6F2N4, the Car-N bonds are slightly shortened with respect to a standard aniline C-N bond [1.3580 (16) and 1.3618 (16) versus 1.39 Å], thus indicating some - conjgation with the electron-acceptor CN groups. The molecule, except for two C atom of the ethylene bridge, is nearly planar, the largest deviation of the other non-H atoms from the mean plane being 0.309 (2) Å. The N-C-C-N torsion angle involving the ethylene bridge is 50.23 (18)°. In the crystal, molecules are connected by pairs of N-HN hydrogen bonds into chains along [21-1].
For general background to the synthesis and use of tetrafluoroterephthalonitrile and its derivatives, see: Meazza et al. (2007). For reference structural data on tetrafluoroterephthalic acid, see: Orthaber et al. (2010). For standard bond lengths, see: Allen et al. (1987). For hydrogen bonding graph-set descriptors, see: Etter (1990).
Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and DIAMOND (Brandenburg, 2005); software used to prepare material for publication: SHELXTL.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: YK2078 ).
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Brandenburg, K. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.
Meazza, G., Bettarini, F. & Fornara, L. (2007). WO Patent No. 2007101587.
Orthaber, A., Seidel, C., Belaj, F., Albering, J. H., Pietschnig, R. & Ruschewitz, U. (2010). Inorg. Chem. 49, 9350-9357.
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.