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Volume 68 
Part 1 
Page o182  
January 2012  

Received 14 November 2011
Accepted 6 December 2011
Online 21 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.041
wR = 0.100
Data-to-parameter ratio = 14.6
Details
Open access

3-[(2-Formylthiophen-3-yl)(hydroxy)methyl]thiophene-2-carbaldehyde

aSchool of Chemical Engineering, Changchun University of Technology, Changchun 130012, People's Republic of China, and bSchool of Chemistry, Jilin University, Changchun 130012, People's Republic of China
Correspondence e-mail: liguijuan@mail.ccut.edu.cn

In the title compound, C11H8O3S2, the dihedral angle between the mean planes of the two thiophene rings is 65.10 (10)°. Intramolecular C-H...O interactions form S(6) and S(7) ring motifs. In the crystal, chains along the a axis are formed by C-H...O interactions. Adjacent chains are connected into a three-dimensional network by C-H...O and O-H...O interactions.

Related literature

For details and applications of thiophene-based aldehydes, see: Basu & Das (2011[Basu, A. & Das, G. (2011). Inorg. Chim. Acta, 372, 394-399.]); Guarín et al. (2007[Guarín, S. A. P., Bourgeaux, M., Dufresne, S. & Skene, W. G. (2007). J. Org. Chem. 72, 2631-2643.]); Herbivo et al. (2009[Herbivo, C., Comel, A., Kirsch, G. & Raposo, M. M. M. (2009). Tetrahedron, 65, 2079-2086.]); Jain et al. (2010[Jain, P., Ferrence, G. M. & Lash, T. D. (2010). J. Org. Chem. 75, 6563-6573.]). For hydrogen-bonding 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.]). For optical applications of formyl thiophene derivatives, see: Raposo & Kirsch (2003[Raposo, M. M. M. & Kirsch, G. (2003). Tetrahedron, 59, 4891-4899.]); Raposo et al. (2004[Raposo, M. M. M., Fonseca, A. M. C. & Kirsch, G. (2004). Tetrahedron, 60, 4071-4078.]). For related Schiff base compounds reported by our group, see: Su et al. (2007a[Su, Q., Wu, Q.-L., Li, G.-H., Gao, W. & Mu, Y. (2007a). Acta Cryst. E63, o2052-o2053.],b[Su, Q., Wu, Q.-L., Li, G.-H., Liu, X.-M. & Mu, Y. (2007b). Polyhedron, 26, 5053-5060.],c[Su, Q., Gao, W., Wu, Q.-L., Ye, L., Li, G.-H. & Mu, Y. (2007c). Eur. J. Inorg. Chem. pp. 4168-4175.], 2009[Su, Q., Wu, Q.-L., Ye, L. & Mu, Y. (2009). Acta Cryst. E65, o2537.]).

[Scheme 1]

Experimental

Crystal data
  • C11H8O3S2

  • Mr = 252.29

  • Monoclinic, P 21 /c

  • a = 7.6227 (18) Å

  • b = 10.136 (2) Å

  • c = 14.272 (3) Å

  • [beta] = 101.998 (4)°

  • V = 1078.7 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.48 mm-1

  • T = 293 K

  • 0.26 × 0.24 × 0.21 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.886, Tmax = 0.906

  • 6687 measured reflections

  • 2122 independent reflections

  • 1798 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.100

  • S = 1.03

  • 2122 reflections

  • 145 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C6-H6...O2 0.98 2.43 3.101 (3) 125
C11-H11...O2 0.93 2.50 3.261 (3) 139
C4-H4...O1i 0.93 2.55 3.377 (3) 149
C9-H9...O2ii 0.93 2.57 3.458 (3) 160
C10-H10...O3ii 0.93 2.55 3.397 (3) 152
O1-H1...O3iii 0.82 2.03 2.825 (2) 162
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) x+1, y, z; (iii) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). SMART 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: MW2040 ).


References

Basu, A. & Das, G. (2011). Inorg. Chim. Acta, 372, 394-399.  [CSD] [CrossRef] [ChemPort]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Guarín, S. A. P., Bourgeaux, M., Dufresne, S. & Skene, W. G. (2007). J. Org. Chem. 72, 2631-2643.  [PubMed]
Herbivo, C., Comel, A., Kirsch, G. & Raposo, M. M. M. (2009). Tetrahedron, 65, 2079-2086.  [CrossRef] [ChemPort]
Jain, P., Ferrence, G. M. & Lash, T. D. (2010). J. Org. Chem. 75, 6563-6573.  [CSD] [CrossRef] [ChemPort] [PubMed]
Raposo, M. M. M., Fonseca, A. M. C. & Kirsch, G. (2004). Tetrahedron, 60, 4071-4078.  [CrossRef] [ChemPort]
Raposo, M. M. M. & Kirsch, G. (2003). Tetrahedron, 59, 4891-4899.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Su, Q., Gao, W., Wu, Q.-L., Ye, L., Li, G.-H. & Mu, Y. (2007c). Eur. J. Inorg. Chem. pp. 4168-4175.  [CSD] [CrossRef]
Su, Q., Wu, Q.-L., Li, G.-H., Gao, W. & Mu, Y. (2007a). Acta Cryst. E63, o2052-o2053.  [CSD] [CrossRef] [details]
Su, Q., Wu, Q.-L., Li, G.-H., Liu, X.-M. & Mu, Y. (2007b). Polyhedron, 26, 5053-5060.  [CSD] [CrossRef] [ChemPort]
Su, Q., Wu, Q.-L., Ye, L. & Mu, Y. (2009). Acta Cryst. E65, o2537.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o182  [ doi:10.1107/S1600536811052500 ]

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