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

Bolduc, A.; Knipping, É.; Skene, W.G.

doi:10.1107/S1600536812043188

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 (C-C) = 0.002 Å
R = 0.035
wR = 0.102
Data-to-parameter ratio = 14.2
Details

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

Andréanne Bolduc,^a Étienne Knipping ^a and W. G. Skene ^a ^*

^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).

Experimental

Crystal data

C₁₁H₇N₃S
M_r = 213.26
Monoclinic, P 2₁ /c
a = 3.8451 (1) Å
b = 20.8901 (4) Å
c = 12.2725 (2) Å
= 94.952 (1)°
V = 982.10 (4) Å³
Z = 4
Cu K radiation
= 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) T_min = 0.637, T_max = 0.710
13010 measured reflections
1940 independent reflections
1777 reflections with I > 2(I)
R_int = 0.037

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.102
S = 1.08
1940 reflections
137 parameters
H-atom parameters constrained
_max = 0.20 e Å^-3
_min = -0.24 e Å^-3

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: UdMX (Marris, 2004).

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.
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.
Skene, W. G., Dufresne, S., Trefz, T. & Simard, M. (2006). Acta Cryst. E62, o2382-o2384.

organic compounds