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Volume 69 
Part 5 
Page o672  
May 2013  

Received 27 March 2013
Accepted 2 April 2013
Online 10 April 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.004 Å
R = 0.032
wR = 0.100
Data-to-parameter ratio = 15.4
Details
Open access

1-(10-Bromoanthracen-9-yl)-1H-imidazole

aNational Changhua University of Education, Department of Chemistry, Changhua, 50058, Taiwan
Correspondence e-mail: leehm@cc.ncue.edu.tw

In the title molecule, C17H11BrN2, the planes of the anthracene ring system [maximum deviation from the mean plane = 0.036 (3) Å] and the imidazole ring form a dihedral angle of 85.14 (14)°. In the crystal, weak C-H...N and C-H...Br hydrogen bonds link the molecules into double chains propagating along [01-1]. In addition, [pi]-[pi] stacking interactions between pairs of benzene rings are observed, with centroid-centroid distances of 3.7968 (17) and 3.8496 (16) Å.

Related literature

For the preparation of the title compound, see: Lee et al. (2011[Lee, H.-J., Cheng, P.-Y., Chen, C.-Y., Shen, J.-S., Nandi, D. & Lee, H. M. (2011). CrystEngComm, 13, 4814-4816.]). For the structure of a related compound, see: Boyer et al. (1993[Boyer, G., Claramunt, R. M., Elguero, J., Fathalla, M., Foces-Foces, C., Jaime, C. & LIamas-Saiz, A. L. (1993). J. Chem. Soc. Perkin Trans. 2, pp. 757-766.]).

[Scheme 1]

Experimental

Crystal data
  • C17H11BrN2

  • Mr = 323.19

  • Triclinic, [P \overline 1]

  • a = 8.1832 (2) Å

  • b = 8.8473 (2) Å

  • c = 9.5814 (2) Å

  • [alpha] = 75.355 (1)°

  • [beta] = 81.624 (1)°

  • [gamma] = 77.134 (1)°

  • V = 651.36 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 3.15 mm-1

  • T = 150 K

  • 0.35 × 0.26 × 0.07 mm

Data collection
  • Bruker SMART APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.]) Tmin = 0.406, Tmax = 0.822

  • 6236 measured reflections

  • 2846 independent reflections

  • 2562 reflections with I > 2[sigma]

  • Rint = 0.017

Refinement
  • R[F2 > 2[sigma](F2)] = 0.032

  • wR(F2) = 0.100

  • S = 1.11

  • 2846 reflections

  • 185 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.54 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3...Br1i 0.95 2.86 3.687 (3) 147
C3-H3...N2ii 0.95 2.58 3.393 (4) 144
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x+1, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5602 ).


Acknowledgements

We thank the National Science Council of Taiwan for financial support of this work.

References

Boyer, G., Claramunt, R. M., Elguero, J., Fathalla, M., Foces-Foces, C., Jaime, C. & LIamas-Saiz, A. L. (1993). J. Chem. Soc. Perkin Trans. 2, pp. 757-766.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Lee, H.-J., Cheng, P.-Y., Chen, C.-Y., Shen, J.-S., Nandi, D. & Lee, H. M. (2011). CrystEngComm, 13, 4814-4816.  [ISI] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o672  [ doi:10.1107/S160053681300891X ]

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