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Volume 68 
Part 12 
Page o3262  
December 2012  

Received 18 September 2012
Accepted 16 October 2012
Online 3 November 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.035
wR = 0.102
Data-to-parameter ratio = 14.2
Details
Open access

2-[(E)-(Pyridin-2-ylmethylidene)amino]thiophene-3-carbonitrile

aDepartment of Chemistry, Université de Montréall, CP 6128, succ. Centre-ville, Montréal, Qc, Canada
Correspondence e-mail: w.skene@umontreal.ca

In the title compound, C11H7N3S, the thiophene and pyridine rings are coplanar, forming a dihedral angle of 3.89 (7)°. The conformation about the C=N bond [1.2795 (18) Å] is E. In the crystal, translationally related molecules along the a axis form weak [pi]-[pi] interactions [centroid-centroid distance = 3.8451 (8) Å] between the thiophene rings.

Related literature

For a related structure, see: Skene et al. (2006[Skene, W. G., Dufresne, S., Trefz, T. & Simard, M. (2006). Acta Cryst. E62, o2382-o2384.]).

[Scheme 1]

Experimental

Crystal data
  • C11H7N3S

  • Mr = 213.26

  • Monoclinic, P 21 /c

  • a = 3.8451 (1) Å

  • b = 20.8901 (4) Å

  • c = 12.2725 (2) Å

  • [beta] = 94.952 (1)°

  • V = 982.10 (4) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 2.64 mm-1

  • T = 296 K

  • 0.18 × 0.14 × 0.13 mm

Data collection
  • Bruker SMART 6000 diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.637, Tmax = 0.710

  • 13010 measured reflections

  • 1940 independent reflections

  • 1777 reflections with I > 2[sigma](I)

  • Rint = 0.037

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

  • wR(F2) = 0.102

  • S = 1.08

  • 1940 reflections

  • 137 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). 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: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: UdMX (Marris, 2004[Marris, T. (2004). UdMX. Université de Montréal, Montréal, Québec, Canada.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LX2267 ).


Acknowledgements

The authors acknowledge financial support from the Natural Sciences and Engineering Research Council Canada (NSERC), the Centre for Self-Assembled Chemical Structures, and the Canada Foundation for Innovation. AB thanks both NSERC and the Université de Montréal for graduate scholarships.

References

Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Marris, T. (2004). UdMX. Université de Montréal, Montréal, Québec, Canada.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Skene, W. G., Dufresne, S., Trefz, T. & Simard, M. (2006). Acta Cryst. E62, o2382-o2384.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o3262  [ doi:10.1107/S1600536812043188 ]

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