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Volume 69 
Part 12 
Pages o1732-o1733  
December 2013  

Received 25 September 2013
Accepted 21 October 2013
Online 6 November 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.031
wR = 0.078
Data-to-parameter ratio = 21.1
Details
Open access

5-Bromo­benzene-1,3-dicarbo­nitrile

aInstitut für Organische Chemie, TU Bergakademie Freiberg, Leipziger Strasse 29, D-09596 Freiberg/Sachsen, Germany
Correspondence e-mail: edwin.weber@chemie-tu.freiberg.de

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-H...N hydrogen bonds with one N atom acting as a bifurcated acceptor. N...Br inter­actions also occur [N...Br = 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].

Related literature

For use of aromatic nitrils in organic synthesis and for their industrial applications, see: Fabiani (1999[Fabiani, M. E. (1999). Drug News Perspect. 12, 207-214.]); Ishii et al. (2011[Ishii, G., Moriyama, K. & Togo, H. (2011). Tetrahedron Lett. 52, 2404-2406.]); Sandier & Karo (1983[Sandier, S. R. & Karo, W. (1983). In Organic Functional Group Preparations. Academic Press: San Diego.]). For uses of aromatic nitrils in crystal engineering and the construction of metal-organic frameworks, see: Desiraju & Harlow (1989[Desiraju, G. R. & Harlow, R. L. (1989). J. Am. Chem. Soc. 111, 6757-6764.]); Leonard & MacGillivray (2010[Leonard, R. & MacGillivray, R. (2010). Editors. Metal-Organic Frameworks. Wiley: Hoboken.]); Reddy et al. (1993[Reddy, D. S., Pannerselvam, K., Pilati, T. & Desiraju, G. R. (1993). J. Chem. Soc. Chem. Commun. pp. 661-662.]); Tiekink et al. (2010[Tiekink, E. R. T., Vittal, J. J. & Zaworotko, M. J. (2010). Editors. Organic Crystal Engineering. Wiley: Chichester.]). For the X-ray structure of 1,3,5-tri­cyano­benzene, see: Reddy et al. (1995[Reddy, D. S., Panneerselvam, K., Desiraju, G. R., Carrell, H. L. & Carrell, C. J. (1995). Acta Cryst. C51, 2352-2354.]). For non-covalant C-H...N and N...Br inter­actions as well as arene...arene stacking contacts, see: Desiraju & Steiner (1999[Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond, pp. 29-123. Oxford University Press.]); Dance (2004[Dance, I. (2004). Encyclopedia of Supramolecular Chemistry, pp. 1076-1092. New York: Dekker.]); Rowland & Taylor (1996[Rowland, R. S. & Taylor, R. (1996). J. Phys. Chem. 100, 7384-7391.]); Steiner (2002[Steiner, T. (2002). Angew. Chem. Int Ed. 114, 50-80.]). For the preparation of the title compound, see: Doyle & Haseltine (1994[Doyle, T. & Haseltine, J. (1994). J. Heterocycl. Chem. 31, 1417-1420.]).

[Scheme 1]

Experimental

Crystal data
  • C8H3BrN2

  • Mr = 207.03

  • Monoclinic, P 21 /c

  • a = 13.3019 (4) Å

  • b = 15.7762 (5) Å

  • c = 7.4265 (2) Å

  • [beta] = 93.719 (2)°

  • V = 1555.19 (8) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 5.21 mm-1

  • T = 173 K

  • 0.45 × 0.43 × 0.08 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.203, Tmax = 0.681

  • 16811 measured reflections

  • 4198 independent reflections

  • 3436 reflections with I > 2[sigma](I)

  • Rint = 0.039

Refinement
  • R[F2 > 2[sigma](F2)] = 0.031

  • wR(F2) = 0.078

  • S = 1.05

  • 4198 reflections

  • 199 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.60 e Å-3

  • [Delta][rho]min = -0.58 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C4A-H4A...N2i 0.95 2.69 3.388 (3) 130
C4-H4...N2Ai 0.95 2.61 3.444 (3) 147
C6A-H6A...N1Aii 0.95 2.67 3.563 (3) 157
C2-H2...N1iii 0.95 2.69 3.624 (3) 168
C2A-H2A...N1iii 0.95 2.72 3.435 (3) 133
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-NT (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZP2009 ).


Acknowledgements

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).

References

Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Dance, I. (2004). Encyclopedia of Supramolecular Chemistry, pp. 1076-1092. New York: Dekker.
Desiraju, G. R. & Harlow, R. L. (1989). J. Am. Chem. Soc. 111, 6757-6764.  [CSD] [CrossRef] [ChemPort] [Web of Science]
Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond, pp. 29-123. Oxford University Press.
Doyle, T. & Haseltine, J. (1994). J. Heterocycl. Chem. 31, 1417-1420.  [CrossRef] [ChemPort]
Fabiani, M. E. (1999). Drug News Perspect. 12, 207-214.  [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Ishii, G., Moriyama, K. & Togo, H. (2011). Tetrahedron Lett. 52, 2404-2406.  [Web of Science] [CrossRef] [ChemPort]
Leonard, R. & MacGillivray, R. (2010). Editors. Metal-Organic Frameworks. Wiley: Hoboken.
Reddy, D. S., Panneerselvam, K., Desiraju, G. R., Carrell, H. L. & Carrell, C. J. (1995). Acta Cryst. C51, 2352-2354.  [CSD] [CrossRef] [IUCr Journals]
Reddy, D. S., Pannerselvam, K., Pilati, T. & Desiraju, G. R. (1993). J. Chem. Soc. Chem. Commun. pp. 661-662.  [CrossRef] [Web of Science]
Rowland, R. S. & Taylor, R. (1996). J. Phys. Chem. 100, 7384-7391.  [CrossRef] [ChemPort] [Web of Science]
Sandier, S. R. & Karo, W. (1983). In Organic Functional Group Preparations. Academic Press: San Diego.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Steiner, T. (2002). Angew. Chem. Int Ed. 114, 50-80.
Tiekink, E. R. T., Vittal, J. J. & Zaworotko, M. J. (2010). Editors. Organic Crystal Engineering. Wiley: Chichester.


Acta Cryst (2013). E69, o1732-o1733   [ doi:10.1107/S1600536813028857 ]

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