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

Sun, L.; Li, G.; Su, Q.

doi:10.1107/S1600536811052500

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 (C-C) = 0.003 Å
R = 0.041
wR = 0.100
Data-to-parameter ratio = 14.6
Details

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

Lili Sun,^a Guijuan Li ^a ^* and Qing Su ^b

^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-HO interactions form S(6) and S(7) ring motifs. In the crystal, chains along the a axis are formed by C-HO interactions. Adjacent chains are connected into a three-dimensional network by C-HO and O-HO interactions.

Related literature

For details and applications of thiophene-based aldehydes, see: Basu & Das (2011); Guarín et al. (2007); Herbivo et al. (2009); Jain et al. (2010). For hydrogen-bonding motifs, see: Bernstein et al. (1995). For optical applications of formyl thiophene derivatives, see: Raposo & Kirsch (2003); Raposo et al. (2004). For related Schiff base compounds reported by our group, see: Su et al. (2007a,b,c, 2009).

Experimental

Crystal data

C₁₁H₈O₃S₂
M_r = 252.29
Monoclinic, P 2₁ /c
a = 7.6227 (18) Å
b = 10.136 (2) Å
c = 14.272 (3) Å
= 101.998 (4)°
V = 1078.7 (4) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.886, T_max = 0.906
6687 measured reflections
2122 independent reflections
1798 reflections with I > 2(I)
R_int = 0.025

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.100
S = 1.03
2122 reflections
145 parameters
H-atom parameters constrained
_max = 0.31 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C6-H6O2	0.98	2.43	3.101 (3)	125
C11-H11O2	0.93	2.50	3.261 (3)	139
C4-H4O1ⁱ	0.93	2.55	3.377 (3)	149
C9-H9O2ⁱⁱ	0.93	2.57	3.458 (3)	160
C10-H10O3ⁱⁱ	0.93	2.55	3.397 (3)	152
O1-H1O3ⁱⁱⁱ	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); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); 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.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
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.
Herbivo, C., Comel, A., Kirsch, G. & Raposo, M. M. M. (2009). Tetrahedron, 65, 2079-2086.
Jain, P., Ferrence, G. M. & Lash, T. D. (2010). J. Org. Chem. 75, 6563-6573.
Raposo, M. M. M., Fonseca, A. M. C. & Kirsch, G. (2004). Tetrahedron, 60, 4071-4078.
Raposo, M. M. M. & Kirsch, G. (2003). Tetrahedron, 59, 4891-4899.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Su, Q., Gao, W., Wu, Q.-L., Ye, L., Li, G.-H. & Mu, Y. (2007c). Eur. J. Inorg. Chem. pp. 4168-4175.
Su, Q., Wu, Q.-L., Li, G.-H., Gao, W. & Mu, Y. (2007a). Acta Cryst. E63, o2052-o2053.
Su, Q., Wu, Q.-L., Li, G.-H., Liu, X.-M. & Mu, Y. (2007b). Polyhedron, 26, 5053-5060.
Su, Q., Wu, Q.-L., Ye, L. & Mu, Y. (2009). Acta Cryst. E65, o2537.

organic compounds