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

Akkurt, M.; Kennedy, A.R.; Younes, S.H.H.; Mohamed, S.K.; Miller, G.J.

doi:10.1107/S160053681204593X

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 (C-C) = 0.003 Å
R = 0.045
wR = 0.106
Data-to-parameter ratio = 18.8
Details

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

Mehmet Akkurt,^a ^* Alan R. Kennedy,^b ^* Sabry H. H. Younes,^c Shaaban K. Mohamed ^d,^e and Gary J. Miller ^f ^*

^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-HO hydrogen bonds, while the crystal packing is stabilized by C-HO, 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, 2012); Litvinov (2005). For their industrial applications, see: Lee & Sotzing (2001); Heeney et al. (2005); Gather et al. (2008); He et al. (2009). For pharmaceutical values of thieno[2,3-b]thiophenes, see: Jarak et al. (2006); Egbertson et al. (1999). For bond lengths and bond angles in similar compounds, see: Umadevi et al. (2009); Gunasekaran et al. (2009); Wang et al. (2008). For the synthesis of the title compound, see: Comel & Kirsch (2001a,b). For graph-set descriptions of hydrogen-bond ring motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₄H₁₆O₄S₂
M_r = 312.39
Triclinic, $[P \overline 1]$
a = 7.3497 (3) Å
b = 8.4720 (4) Å
c = 12.8629 (5) Å
= 102.770 (3)°
= 99.545 (3)°
= 107.779 (4)°
V = 719.96 (6) Å³
Z = 2
Mo K radiation
= 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 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.966, T_max = 1.000
6901 measured reflections
3486 independent reflections
2661 reflections with I > 2(I)
R_int = 0.025

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.106
S = 1.04
3486 reflections
185 parameters
H-atom parameters constrained
_max = 0.53 e Å^-3
_min = -0.34 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

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

D-HA	D-H	HA	DA	D-HA
C7-H7AO1	0.98	2.22	2.980 (3)	133
C8-H8AO3	0.98	2.23	2.909 (3)	125
C11-H11AO4ⁱ	0.98	2.53	3.471 (3)	161
C8-H8CCg2ⁱⁱ	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012) 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

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organic compounds