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Volume 69 
Part 9 
Page o1367  
September 2013  

Received 3 July 2013
Accepted 28 July 2013
Online 3 August 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.005 Å
R = 0.035
wR = 0.085
Data-to-parameter ratio = 16.5
Details
Open access

(E)-2-Bromomethyl-3-(o-tolyl)acrylonitrile

aDepartment of Physics, Velammal Institute of Technology, Panchetty, Chennai 601 204, India,bDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India,cDepartment of Organic Chemistry, University of Madras, Guindy campus, Chennai 600 025, India,dDepartment of Physics & Nano Technology, SRM University, SRM Nagar, Kattankulathur, Kancheepuram Dist, Chennai 603 203 Tamil Nadu, India, and eDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
Correspondence e-mail: phdguna@gmail.com, crystallography2010@gmail.com

The title compound C11H10BrN, has an E conformation at the C=C bond of the acrylonitrile unit. The vinyl group makes a dihedral angle of 44.53 (12)° with the benzene ring. In the crystal, weak C-H...[pi] interactions involving the benzene ring are observed.

Related literature

For the biological activity of cyanoacrylates, see: Zhang et al. (2009[Zhang, D., Zhang, X. & Guo, L. (2009). Acta Cryst. E65, o90.]); Obniska et al. (2005[Obniska, J., Jurczyk, S., Zejc, A., Kaminski, K., Tatarczynska, E. & Stachowicz, K. (2005). Pharmacol. Rep. 57, 170-175.]); For related structures, see: Ye et al. (2009[Ye, Y., Shen, W.-L. & Wei, X.-W. (2009). Acta Cryst. E65, o2636.]); Suresh et al. (2012[Suresh, G., Sabari, V., Srinivasan, J., Mannickam, B. & Aravindhan, S. (2012). Acta Cryst. E68, o570.]).

[Scheme 1]

Experimental

Crystal data
  • C11H10BrN

  • Mr = 236.11

  • Monoclinic, P 21 /n

  • a = 7.5473 (8) Å

  • b = 11.7362 (10) Å

  • c = 11.5228 (11) Å

  • [beta] = 96.436 (3)°

  • V = 1014.22 (17) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 4.00 mm-1

  • T = 295 K

  • 0.20 × 0.20 × 0.15 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.]) Tmin = 0.435, Tmax = 0.535

  • 8718 measured reflections

  • 1960 independent reflections

  • 1261 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.085

  • S = 1.00

  • 1960 reflections

  • 119 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.46 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 ring

D-H...A D-H H...A D...A D-H...A
C7-H7...Cg1i 0.93 2.97 3.654 (7) 131
C11-H11B...Cg1ii 0.96 2.86 3.699 (1) 146
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+2, -y, -z+1.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2587 ).


References

Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Obniska, J., Jurczyk, S., Zejc, A., Kaminski, K., Tatarczynska, E. & Stachowicz, K. (2005). Pharmacol. Rep. 57, 170-175.  [PubMed] [ChemPort]
Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Suresh, G., Sabari, V., Srinivasan, J., Mannickam, B. & Aravindhan, S. (2012). Acta Cryst. E68, o570.  [CSD] [CrossRef] [details]
Ye, Y., Shen, W.-L. & Wei, X.-W. (2009). Acta Cryst. E65, o2636.  [CSD] [CrossRef] [details]
Zhang, D., Zhang, X. & Guo, L. (2009). Acta Cryst. E65, o90.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o1367  [ doi:10.1107/S1600536813021041 ]

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