Received 25 September 2013
The asymmetric unit of the title compound, C8H3BrN2, consists of two molecules. The crystal structure features undulating molecular sheets with the molecules linked by C-HN hydrogen bonds with one N atom acting as a bifurcated acceptor. NBr interactions also occur [NBr = 2.991 (3) and 3.099 (3) Å]. Interlayer association is accomplished by offset face-to-face arene interactions [centroid-centroid distance = 3.768 (4) Å].
For use of aromatic nitrils in organic synthesis and for their industrial applications, see: Fabiani (1999); Ishii et al. (2011); Sandier & Karo (1983). For uses of aromatic nitrils in crystal engineering and the construction of metal-organic frameworks, see: Desiraju & Harlow (1989); Leonard & MacGillivray (2010); Reddy et al. (1993); Tiekink et al. (2010). For the X-ray structure of 1,3,5-tricyanobenzene, see: Reddy et al. (1995). For non-covalant C-HN and NBr interactions as well as arenearene stacking contacts, see: Desiraju & Steiner (1999); Dance (2004); Rowland & Taylor (1996); Steiner (2002). For the preparation of the title compound, see: Doyle & Haseltine (1994).
Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT-NT (Bruker, 2007); data reduction: SAINT-NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZP2009 ).
This work was performed within the Cluster of Excellence "Structure Design of Novel High-Performance Materials via Atomic Design and Defect Engineering (ADDE)" which is supported financially by the European Union (European Regional Development Fund) and by the Ministry of Science and Art of Saxony (SMWK).
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