(2E)-3-(3,4-Dimeth­oxy­phen­yl)-1-(2,5-dimethyl­thio­phen-3-yl)prop-2-en-1-one

Asiri, A.M.; Khan, S.A.; Tahir, M.N.

doi:10.1107/S1600536810029272

Volume 66
Part 8
Page o2133
August 2010

Received 18 July 2010
Accepted 22 July 2010
Online 31 July 2010

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.036
wR = 0.106
Data-to-parameter ratio = 14.6
Details

(2E)-3-(3,4-Dimethoxyphenyl)-1-(2,5-dimethylthiophen-3-yl)prop-2-en-1-one

Abdullah M. Asiri,^a,^b Salman A. Khan ^b and M. Nawaz Tahir ^c ^*

^aThe Center of Excellence for Advanced Materials Research, King Abdul Aziz University, Jeddah 21589, PO Box 80203, Saudi Arabia,^bDepartment of Chemistry, Faculty of Science, King Abdul Aziz University, Jeddah 21589, PO Box 80203, Saudi Arabia, and ^cDepartment of Physics, University of Sargodha, Sargodha, Pakistan
Correspondence e-mail: dmntahir_uos@yahoo.com

The molecule of the title compound, C₁₇H₁₈O₃S, is essentially planar: the phenyl and thiophene rings form a dihedral angle of 2.79 (10)° and they are inclined to the central propenone unit by 6.20 (15) and 4.78 (15)°, respectively. In the crystal, molecules are connected into dimers via pairs of C-HO interactions, generating R₂²(14) motifs. [pi] - [pi] stacking interactions between the thiophene rings also occur, with a centroid-centroid distance of 3.8062 (12) Å.

Related literature

For background to chalcones, their activity and applications, see: Bandgar et al. (2010); Deng et al. (2007); Liu et al. (2003); Verma et al. (2007). For graph-set notation, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₇H₁₈O₃S
M_r = 302.37
Monoclinic, P 2₁ /n
a = 9.1821 (6) Å
b = 8.3529 (5) Å
c = 20.3443 (13) Å
= 94.624 (4)°
V = 1555.27 (17) Å³
Z = 4
Mo K radiation
= 0.22 mm^-1
T = 296 K
0.30 × 0.24 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.868, T_max = 0.965
11371 measured reflections
2791 independent reflections
2182 reflections with I > 2(I)
R_int = 0.025

Refinement

R[F² > 2(F²)] = 0.036
wR(F²) = 0.106
S = 1.07
2791 reflections
191 parameters
H-atom parameters constrained
_max = 0.15 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C6-H6O3ⁱ	0.93	2.41	3.175 (2)	139
Symmetry code: (i) -x+1, -y, -z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; 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, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2297 ).

Acknowledgements

The authors would like to thank the Chemistry Department, King Abdul Aziz University, Jeddah, Saudi Arabia for providing research facilities and for financial support of this work via grant No. 3-045/430.

References

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Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Deng, J., Sanchez, T., Al-Mawsawi, L. Q., Dayam, R., Yunes, R. A., Garofalo, A., Bolger, M. B. & Neamati, N. (2007). Bioorg. Med. Chem. 15, 4985-5002.
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Verma, A. K., Koul, S., Pannu, A. P. S. & Razdan, T. K. (2007). Tetrahedron, 63, 8715-8722.

organic compounds