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Volume 65 
Part 10 
Page o2484  
October 2009  

Received 2 September 2009
Accepted 11 September 2009
Online 19 September 2009


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Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.006 Å
Disorder in main residue
R = 0.073
wR = 0.173
Data-to-parameter ratio = 14.6
Details

Bis(2-thienyl)acetylene

Emily M. Harcourt,a Daniel E. Lynchb and Darren G. Hamiltona*

aDepartment of Chemistry, Mount Holyoke College, South Hadley, MA 01075, USA, and bExilica Limited, The Technocentre, Puma Way, Coventry CV1 2TT, UK
Correspondence e-mail: hamilton@mtholyoke.edu

The planar [maximum deviation 0.0066 (4) Å] symmetrical molecule of the title compound, C10H6S2, lies across a crystallographic inversion centre. The thiophene rings are rotationally disordered about the acetylene bond, with the two pseudo inversion-related S atoms in 0.80:0.20 occupancy sites. The C[triple bond]C bond distance is 1.195 (9) Å.

Related literature

For the preparation of the title compound, related diarylacetylenes and cobalt-containing metallocenes derived from these materials, see: Harrison et al. (1997[Harrison, R. M., Brotin, T., Noll, B. C. & Michl, J. (1997). Organometallics, 16, 3401-3412.]); Harcourt et al. (2008[Harcourt, E. M., Yonis, S. R., Lynch, D. E. & Hamilton, D. G. (2008). Organometallics, 27, 1653-1656.]). For recent synthetic organic uses, see: Yu & Rovis (2006[Yu, R. & Rovis, T. (2006). J. Am. Chem. Soc. 128, 2782-2783.]); Geyer et al. (2008[Geyer, A. M., Wiedner, E. S., Gary, J. B., Gdula, R. L., Kuhlmann, N. C., Johnson, M. J. A., Dunietz, B. D. & Kampf, J. W. (2008). J. Am. Chem. Soc. 130, 8984-8999.]). The metal center employed in an acetylene cyclooligomerization may also remain as an integral component of the product, or products, see: Rausch & Genetti (1970[Rausch, M. D. & Genetti, R. A. (1970). J. Org. Chem.35, 3888-3897.]). For spectroscopic data, see: Mio et al. (2002[Mio, M. J., Kopel, L. C., Braun, J. B., Gadzikwa, T. L., Hull, K. L., Brisbois, R. G., Markworth, C. J. & Grieco, P. A. (2002). Org. Lett. 4, 3199-3202.]).

[Scheme 1]

Experimental

Crystal data

  • C10H6S2

  • Mr = 190.29

  • Orthorhombic, P b c n

  • a = 10.6325 (15) Å

  • b = 10.8713 (15) Å

  • c = 7.5600 (5) Å

  • V = 873.85 (18) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.54 mm-1

  • T = 120 K

  • 0.55 × 0.05 × 0.03 mm
Data collection

  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.755, Tmax = 0.984

  • 3812 measured reflections

  • 849 independent reflections

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

  • Rint = 0.129
Refinement

  • R[F2 > 2[sigma](F2)] = 0.073

  • wR(F2) = 0.173

  • S = 1.08

  • 849 reflections

  • 58 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.41 e Å-3

  • [Delta][rho]min = -0.41 e Å-3

Data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and COLLECT; data reduction: DENZO and COLLECT; 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.]); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2008 ).

Acknowledgements

We thank the Donors of the American Chemical Society Petroleum Research Fund (Award 45312), the Camille and Henry Dreyfus Foundation (Henry Dreyfus Teacher Scholar Award to DGH, 2005-2010) and the EPSRC National Crystallography Service (University of Southampton, UK) for their support of this work.

References

Geyer, A. M., Wiedner, E. S., Gary, J. B., Gdula, R. L., Kuhlmann, N. C., Johnson, M. J. A., Dunietz, B. D. & Kampf, J. W. (2008). J. Am. Chem. Soc. 130, 8984-8999.  [CrossRef] [PubMed] [ChemPort]
Harcourt, E. M., Yonis, S. R., Lynch, D. E. & Hamilton, D. G. (2008). Organometallics, 27, 1653-1656.  [CrossRef] [ChemPort]
Harrison, R. M., Brotin, T., Noll, B. C. & Michl, J. (1997). Organometallics, 16, 3401-3412.  [CrossRef] [ChemPort]
Mio, M. J., Kopel, L. C., Braun, J. B., Gadzikwa, T. L., Hull, K. L., Brisbois, R. G., Markworth, C. J. & Grieco, P. A. (2002). Org. Lett. 4, 3199-3202.  [CrossRef] [PubMed] [ChemPort]
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Rausch, M. D. & Genetti, R. A. (1970). J. Org. Chem.35, 3888-3897.
Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [CrossRef] [details]
Yu, R. & Rovis, T. (2006). J. Am. Chem. Soc. 128, 2782-2783.  [CrossRef] [PubMed] [ChemPort]

Acta Cryst (2009). E65, o2484  [ doi:10.1107/S1600536809036812 ]

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