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Volume 69 
Part 4 
Pages o524-o525  
April 2013  

Received 3 February 2013
Accepted 7 February 2013
Online 9 March 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.054
wR = 0.157
Data-to-parameter ratio = 21.3
Details
Open access

4-Hydroxy-6-methyl-3-[3-(thiophen-2-yl)acryloyl]-2H-pyran-2-one

aLaboratoire d'Électrochimie des Matériaux Moléculaires et Complexes, Centre Univeresitaire de B.B.A., Algeria,bEcole Normale Superieure de Constantine, 25000 Constantine, Algeria,cUniversité 20 Aout 1955, 21000 Skikda, Algeria, and dLaboratoire de Chimie Biomimétique des Métaux de Transition, Institut de Chimie, Strasbourg, France
Correspondence e-mail: boufas_sihem@yahoo.fr

The title compound, C13H10O4S, crystallizes with two molecules in the asymmetric unit in which the rings make dihedral angles of 3.9 (1) and 6.0 (1)°; this planarity is due in part to the presence of an intramolecular O-H...O hydrogen bond, which generates an S(6) ring in each molecule. Both molecules represent E isomers with respect to the central C=C bond. In the crystal, molecules are linked by C-H...O interactions into a three-dimensional network.

Related literature

For pharmacological properties of chalcones, see: Wattenberg et al. (1994[Wattenberg, L. W., Coccia, J. B. & Galbraith, A. R. (1994). Cancer Lett. 83, 165-169.]); Dinkova-Kostova et al. (1998[Dinkova-Kostova, A. T., Abeygunawardana, C. & Talalay, P. (1998). J. Med. Chem. 41, 5287-5296.]); Ram et al. (2000[Ram, V. J., Saxena, A. S., Srivastava, S. & Chandra, S. (2000). Bioorg. Med. Chem. Lett. 10, 2159-2161.]); Kidwai et al. (2001[Kidwai, M., Sapra, P., Mishra, P., Saxena, R. K. & Singh, M. (2001). Bioorg. Med. Chem. 9, 217-220.]); Ballesteros et al. (1995[Ballesteros, J. F., Sanz, M. J., Ubeda, A., Miranda, M. A., Iborra, S., Paya, M. & Alcaraz, M. J. (1995). J. Med. Chem. 38, 2794-2797.]). For their non-linear optical properties, see: Fichou et al. (1988[Fichou, D., Watanabe, T., Takenda, T., Miyata, S., Goto, Y. & Nakayama, M. (1988). Jpn J. Appl. Phys. 27, L429-L430.]) and for their importance, see: Tomazela et al. (2000[Tomazela, D. M., Pupo, M. T., Passador, E. A. P., Da Silva, M. F. G. F., Vieira, P. C., Fernandes, J. B., Rodrigues, F. E., Oliva, G. & Pirani, J. R. (2000). Phytochemistry, 55, 643-651.]). For precursors in the synthesis of flavonoids, see: Drexler & Amiridis (2003[Drexler, M. T. & Amiridis, M. D. (2003). J. Catal. 214, 136-145.]). For graph-set notation, 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 standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C13H10O4S

  • Mr = 262.27

  • Triclinic, [P \overline 1]

  • a = 8.0737 (4) Å

  • b = 9.9428 (5) Å

  • c = 15.0887 (8) Å

  • [alpha] = 87.770 (1)°

  • [beta] = 87.779 (3)°

  • [gamma] = 80.678 (4)°

  • V = 1193.70 (11) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.27 mm-1

  • T = 293 K

  • 0.5 × 0.4 × 0.2 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2002[Sheldrick, G. M. (2002). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.875, Tmax = 0.947

  • 25106 measured reflections

  • 6954 independent reflections

  • 5295 reflections with I > 2[sigma](I)

  • Rint = 0.036

Refinement
  • R[F2 > 2[sigma](F2)] = 0.054

  • wR(F2) = 0.157

  • S = 1.06

  • 6954 reflections

  • 326 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.97 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H33...O4 0.82 1.68 2.421 (2) 150
O7-H77...O8 0.82 1.65 2.400 (2) 150
C8-H8...O5 0.93 2.60 3.481 (3) 159
C10-H10...O6 0.93 2.59 3.280 (3) 132
C10-H10...O8i 0.93 2.59 3.288 (3) 132
C13-H13C...O6ii 0.96 2.58 3.507 (3) 164
C23-H23...O4iii 0.93 2.56 3.245 (3) 131
C25-H25...O7iv 0.93 2.38 3.240 (3) 153
C26-H26B...O1v 0.96 2.41 3.338 (3) 163
Symmetry codes: (i) -x+2, -y, -z+1; (ii) -x+1, -y, -z; (iii) -x+1, -y, -z+1; (iv) x-1, y+1, z; (v) -x+2, -y, -z.

Data collection: COLLECT (Nonius, 2002[Nonius (2002). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO-SMN (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.]); data reduction: EVALCCD (Duisenberg et al., 2003[Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229.]); program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); 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 Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PARST (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LD2095 ).


Acknowledgements

This work was supported by Université Farhat Abbes DZ-19000. Sétif, Algeria.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [ISI] [CrossRef] [ChemPort] [details]
Ballesteros, J. F., Sanz, M. J., Ubeda, A., Miranda, M. A., Iborra, S., Paya, M. & Alcaraz, M. J. (1995). J. Med. Chem. 38, 2794-2797.  [CrossRef] [ChemPort] [PubMed] [ISI]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Dinkova-Kostova, A. T., Abeygunawardana, C. & Talalay, P. (1998). J. Med. Chem. 41, 5287-5296.  [ISI] [CrossRef] [ChemPort] [PubMed]
Drexler, M. T. & Amiridis, M. D. (2003). J. Catal. 214, 136-145.  [ISI] [CrossRef] [ChemPort]
Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229.  [ISI] [CrossRef] [ChemPort] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Fichou, D., Watanabe, T., Takenda, T., Miyata, S., Goto, Y. & Nakayama, M. (1988). Jpn J. Appl. Phys. 27, L429-L430.  [CrossRef] [ChemPort]
Kidwai, M., Sapra, P., Mishra, P., Saxena, R. K. & Singh, M. (2001). Bioorg. Med. Chem. 9, 217-220.  [CrossRef] [PubMed] [ChemPort]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [details]
Nonius (2002). 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.
Ram, V. J., Saxena, A. S., Srivastava, S. & Chandra, S. (2000). Bioorg. Med. Chem. Lett. 10, 2159-2161.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2002). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tomazela, D. M., Pupo, M. T., Passador, E. A. P., Da Silva, M. F. G. F., Vieira, P. C., Fernandes, J. B., Rodrigues, F. E., Oliva, G. & Pirani, J. R. (2000). Phytochemistry, 55, 643-651.  [ISI] [CrossRef] [PubMed] [ChemPort]
Wattenberg, L. W., Coccia, J. B. & Galbraith, A. R. (1994). Cancer Lett. 83, 165-169.  [CrossRef] [ChemPort] [PubMed] [ISI]


Acta Cryst (2013). E69, o524-o525   [ doi:10.1107/S1600536813003826 ]

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