[Journal logo]

Volume 68 
Part 12 
Pages o3332-o3333  
December 2012  

Received 6 November 2012
Accepted 7 November 2012
Online 10 November 2012

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.003 Å
R = 0.045
wR = 0.106
Data-to-parameter ratio = 18.8
Details
Open access

Diethyl 3,4-dimethylthieno[2,3-b]thiophene-2,5-dicarboxylate

aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,bDepartment of Pure & Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, Scotland,cDepartment of Chemistry, Faculty of Science, Sohag University, 82524 Sohag, Egypt,dChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England,eChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, and fAnalytical Sciences, Manchester Metropolitan University, Manchester M1 5GD, England
Correspondence e-mail: akkurt@erciyes.edu.tr, a.r.Kennedy@strath.ac.uk, G.Miller@mmu.ac.uk

In the title compound, C14H16O4S2, the thieno[2,3-b]thiophene ring systems are planar [maximum deviation = 0.008 (2) Å]. The molecular conformation is stabilized by intramolecular C-H...O hydrogen bonds, while the crystal packing is stabilized by C-H...O, C-H...[pi] and [pi]-[pi] stacking [centroid-centroid distance = 3.6605 (14) Å] interactions, which lead to supramolecular layers in the ab plane.

Related literature

For the use of thienthiophenes as versatile precursors for the synthesis of various heterocycles, see: Mabkhot et al. (2010[Mabkhot, Y. N., Kheder, N. A. & Al-Majid, A. M. (2010). Molecules, 15, 9418-9426.], 2012[Mabkhot, N. Y., Barakat, A., Al-Majid, A. M. & Alshahrani, S. A. (2012). Int. J. Mol. Sci. 13, 2263-2275.]); Litvinov (2005[Litvinov, V. P. (2005). Russ. Chem. Rev. 74, 217-248.]). For their industrial applications, see: Lee & Sotzing (2001[Lee, K. & Sotzing, G. A. (2001). Macromolecules, 34, 5746-5747.]); Heeney et al. (2005[Heeney, M., Bailey, C., Genevicius, K., Shkunov, M., Sparrowe, D., Tierney, S. & McCulloch, U. (2005). J. Am. Chem. Soc. 127, 1078-1079.]); Gather et al. (2008[Gather, M. C., Heeny, M., Zhang, W., Whitehead, K. S., Bradley, D. D. C., McCulloch, I. & Campbell, A. J. (2008). Chem. Commun. 9, 1079-1081.]); He et al. (2009[He, M., Li, J., Sorensen, M. L., Zhang, F., Hancock, R. R., Fong, H. H., Pozdin, V. A., Smilgies, D. & Malliaras, G. G. (2009). J. Am. Chem. Soc. 131, 11930-11938.]). For pharmaceutical values of thieno[2,3-b]thiophenes, see: Jarak et al. (2006[Jarak, I., Kralj, M., Piantanida, I., Suman, L., Zinic, M., Pavelic, K. & Karminski-Zamola, G. (2006). Bioorg. Med. Chem. 14, 2859-2868.]); Egbertson et al. (1999[Egbertson, M. S., Cook, J. J., Hednar, H., Prugh, J. D., Hednar, R. A., Gaul, S. L., Gould, R. J., Hartman, G. D., Homnick, C. F., Holahan, L. M. M., Libby, L. A., Lynch, J. J., Sitko, G. R., Stranieri, M. T. & Vassallo, L. M. (1999). J. Med. Chem. 42, 2409-2421.]). For bond lengths and bond angles in similar compounds, see: Umadevi et al. (2009[Umadevi, M., Sureshbabu, R., Mohanakrishnan, A. K., Chakkaravarthi, G. & Manivannan, V. (2009). Acta Cryst. E65, o2790.]); Gunasekaran et al. (2009[Gunasekaran, B., Sureshbabu, R., Mohanakrishnan, A. K., Chakkaravarthi, G. & Manivannan, V. (2009). Acta Cryst. E65, o2455.]); Wang et al. (2008[Wang, X., Li, Y. & Liu, M.-G. (2008). Acta Cryst. E64, o1180.]). For the synthesis of the title compound, see: Comel & Kirsch (2001a[Comel, A. & Kirsch, G. (2001a). J. Heterocycl. Chem. 38, 1167-1171.],b[Comel, A. & Kirsch, G. (2001b). J. Heterocycl. Chem. 38, 1167-1171.]). For graph-set descriptions of hydrogen-bond ring motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C14H16O4S2

  • Mr = 312.39

  • Triclinic, [P \overline 1]

  • a = 7.3497 (3) Å

  • b = 8.4720 (4) Å

  • c = 12.8629 (5) Å

  • [alpha] = 102.770 (3)°

  • [beta] = 99.545 (3)°

  • [gamma] = 107.779 (4)°

  • V = 719.96 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.38 mm-1

  • T = 123 K

  • 0.30 × 0.08 × 0.06 mm

Data collection
  • Oxford Diffraction Xcalibur Eos diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.966, Tmax = 1.000

  • 6901 measured reflections

  • 3486 independent reflections

  • 2661 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.106

  • S = 1.04

  • 3486 reflections

  • 185 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.53 e Å-3

  • [Delta][rho]min = -0.34 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the S2/C1-C4 ring.

D-H...A D-H H...A D...A D-H...A
C7-H7A...O1 0.98 2.22 2.980 (3) 133
C8-H8A...O3 0.98 2.23 2.909 (3) 125
C11-H11A...O4i 0.98 2.53 3.471 (3) 161
C8-H8C...Cg2ii 0.98 2.74 3.578 (3) 144
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5168 ).


Acknowledgements

SHHY thanks Sohag University for facilitating this collaborative project with Manchester Metropolitan University. Our gratitude is extended to Erciyes University and the University of Strathclyde for supporting this study.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Comel, A. & Kirsch, G. (2001a). J. Heterocycl. Chem. 38, 1167-1171.  [ChemPort]
Comel, A. & Kirsch, G. (2001b). J. Heterocycl. Chem. 38, 1167-1171.  [ChemPort]
Egbertson, M. S., Cook, J. J., Hednar, H., Prugh, J. D., Hednar, R. A., Gaul, S. L., Gould, R. J., Hartman, G. D., Homnick, C. F., Holahan, L. M. M., Libby, L. A., Lynch, J. J., Sitko, G. R., Stranieri, M. T. & Vassallo, L. M. (1999). J. Med. Chem. 42, 2409-2421.  [ISI] [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Gather, M. C., Heeny, M., Zhang, W., Whitehead, K. S., Bradley, D. D. C., McCulloch, I. & Campbell, A. J. (2008). Chem. Commun. 9, 1079-1081.  [CrossRef]
Gunasekaran, B., Sureshbabu, R., Mohanakrishnan, A. K., Chakkaravarthi, G. & Manivannan, V. (2009). Acta Cryst. E65, o2455.  [CSD] [CrossRef] [details]
He, M., Li, J., Sorensen, M. L., Zhang, F., Hancock, R. R., Fong, H. H., Pozdin, V. A., Smilgies, D. & Malliaras, G. G. (2009). J. Am. Chem. Soc. 131, 11930-11938.  [ISI] [CrossRef] [PubMed] [ChemPort]
Heeney, M., Bailey, C., Genevicius, K., Shkunov, M., Sparrowe, D., Tierney, S. & McCulloch, U. (2005). J. Am. Chem. Soc. 127, 1078-1079.  [ISI] [CrossRef] [PubMed] [ChemPort]
Jarak, I., Kralj, M., Piantanida, I., Suman, L., Zinic, M., Pavelic, K. & Karminski-Zamola, G. (2006). Bioorg. Med. Chem. 14, 2859-2868.  [CrossRef] [PubMed] [ChemPort]
Lee, K. & Sotzing, G. A. (2001). Macromolecules, 34, 5746-5747.  [ISI] [CrossRef] [ChemPort]
Litvinov, V. P. (2005). Russ. Chem. Rev. 74, 217-248.  [CrossRef] [ChemPort]
Mabkhot, N. Y., Barakat, A., Al-Majid, A. M. & Alshahrani, S. A. (2012). Int. J. Mol. Sci. 13, 2263-2275.  [CrossRef] [ChemPort] [PubMed]
Mabkhot, Y. N., Kheder, N. A. & Al-Majid, A. M. (2010). Molecules, 15, 9418-9426.  [CrossRef] [ChemPort] [PubMed]
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Umadevi, M., Sureshbabu, R., Mohanakrishnan, A. K., Chakkaravarthi, G. & Manivannan, V. (2009). Acta Cryst. E65, o2790.  [CrossRef] [details]
Wang, X., Li, Y. & Liu, M.-G. (2008). Acta Cryst. E64, o1180.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o3332-o3333   [ doi:10.1107/S160053681204593X ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.