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Volume 69 
Part 6 
Page o869  
June 2013  

Received 16 April 2013
Accepted 7 May 2013
Online 11 May 2013

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.003 Å
R = 0.046
wR = 0.128
Data-to-parameter ratio = 12.1
Details
Open access

2-(Pyridin-4-yl)-1H-benzimidazole

aDepartment of Chemistry, State University of New York-College at Geneseo, 1 College Circle, Geneseo, NY 14454, USA
Correspondence e-mail: geiger@geneseo.edu

The title compound, C12H9N3, is an unhydrated analogue of the previously reported trihydrate. The molecule is essentially planar, with a 3.62 (11)° angle between the pyridine and benzimidazole planes. In the crystal, N-H...N hydrogen bonds result in chains of molecules parallel to [010], which are additionally linked by weak [pi]-[pi] stacking interactions [centroid-centroid distance = 3.7469 (17) Å], resulting in extended sheets of molecules parallel to (103).

Related literature

For the structure of the trihydrate of the title compound, see: Huang et al. (2004[Huang, X.-C., Zeng, M.-H. & Ng, S. W. (2004). Acta Cryst. E60, o939-o940.])

[Scheme 1]

Experimental

Crystal data
  • C12H9N3

  • Mr = 195.22

  • Monoclinic, P 21 /n

  • a = 6.0602 (14) Å

  • b = 11.610 (3) Å

  • c = 13.892 (4) Å

  • [beta] = 101.838 (8)°

  • V = 956.6 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 200 K

  • 0.50 × 0.20 × 0.20 mm

Data collection
  • Bruker SMART X2S CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2010[Bruker (2010). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.53, Tmax = 0.98

  • 4809 measured reflections

  • 1699 independent reflections

  • 1125 reflections with I > 2[sigma](I)

  • Rint = 0.058

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.128

  • S = 0.96

  • 1699 reflections

  • 140 parameters

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

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...N3i 0.99 (2) 1.96 (2) 2.924 (2) 165 (2)
Symmetry code: (i) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2, SAINT and SADABS. 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.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2430 ).


Acknowledgements

This work was supported by a Congressionally directed grant from the US Department of Education (grant No. P116Z100020) for the X-ray diffractometer.

References

Bruker (2010). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Huang, X.-C., Zeng, M.-H. & Ng, S. W. (2004). Acta Cryst. E60, o939-o940.  [CSD] [CrossRef] [ChemPort] [details]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
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]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o869  [ doi:10.1107/S160053681301252X ]

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