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Volume 69 
Part 6 
Page o916  
June 2013  

Received 14 March 2013
Accepted 14 May 2013
Online 18 May 2013

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.007 Å
R = 0.059
wR = 0.156
Data-to-parameter ratio = 14.8
Details
Open access

Thiophene-2-carbaldehyde azine

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 asymmetric unit of the title compound, C10H8N2S2, is composed of two independent half-molecules, each residing on a center of symmetry. In the crystal, weak C-H...[pi] interactions join the two symmetry-independent molecules together into interlinked chains parallel to [011]. The crystal structure was refined as a two-component pseudo-merohedral twin using the twin law 001 0-10 100. The refined domain fractions are 0.516 (3) and 0.484 (3).

Related literature

For the structure of pyridine-4-carbaldehyde, see: Shanmuga Sundara Raj et al. (2000[Shanmuga Sundara Raj, S., Fun, H.-K., Zhang, J., Xiong, R.-G. & You, X.-Z. (2000). Acta Cryst. C56, e274-e275.]) and for the structure of (E)-1-diphenylmethylidene-2-[(1H-indol-3-yl)methylidene]hydrazine, see: Archana et al. (2010[Archana, R., Anbazhagan, R., Sankaran, K. R., Thiruvalluvar, A. & Butcher, R. J. (2010). Acta Cryst. E66, o1586.]).

[Scheme 1]

Experimental

Crystal data
  • C10H8N2S2

  • Mr = 220.30

  • Monoclinic, P 21 /n

  • a = 9.681 (2) Å

  • b = 11.399 (3) Å

  • c = 9.694 (2) Å

  • [beta] = 100.850 (9)°

  • V = 1050.6 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.47 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 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.69, Tmax = 0.91

  • 7000 measured reflections

  • 1890 independent reflections

  • 1349 reflections with I > 2[sigma](I)

  • Rint = 0.073

Refinement
  • R[F2 > 2[sigma](F2)] = 0.059

  • wR(F2) = 0.156

  • S = 0.99

  • 1890 reflections

  • 128 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.61 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
C1-H1...C8 0.95 2.77 3.683 (7) 161
C1-H1...C9 0.95 2.85 3.576 (7) 134
C8-H8...C4i 0.95 2.77 3.663 (7) 156
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). 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.]) 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: ZP2003 ).


Acknowledgements

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

References

Archana, R., Anbazhagan, R., Sankaran, K. R., Thiruvalluvar, A. & Butcher, R. J. (2010). Acta Cryst. E66, o1586.  [CSD] [CrossRef] [details]
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
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]
Shanmuga Sundara Raj, S., Fun, H.-K., Zhang, J., Xiong, R.-G. & You, X.-Z. (2000). Acta Cryst. C56, e274-e275.  [CSD] [CrossRef] [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, o916  [ doi:10.1107/S1600536813013275 ]

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