(2E)-1-(5-Bromo­thio­phen-2-yl)-3-(2,3,4-trimeth­oxy­phen­yl)prop-2-en-1-one

Sunitha, K.; Devarajegowda, H.C.; Al-eryani, W.F.A.; Prasad, Y.R.; Kumar, A.U.M.

doi:10.1107/S1600536811052202

Volume 68
Part 1
Page o61
January 2012

Received 14 November 2011
Accepted 3 December 2011
Online 10 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.033
wR = 0.082
Data-to-parameter ratio = 14.0
Details

(2E)-1-(5-Bromothiophen-2-yl)-3-(2,3,4-trimethoxyphenyl)prop-2-en-1-one

K. Sunitha,^a H. C. Devarajegowda,^b ^* Waleed Fadl Ali Al-eryani,^b Y. Rajendra Prasad ^c and A. Uma Mahesh Kumar ^a

^aInstitute of Pharmacy, GITAM University, Visakhapatnam 45, Andhrapradesh, India,^bDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India, and ^cDepartment of Pharmaceutical Chemistry, AU College of Pharmacy, Andhra University, Visakhapatnam, Andhrapradesh, India
Correspondence e-mail: devarajegowda@yahoo.com

In the title compound, C₁₆H₁₅BrO₄S, the thiophene ring is not coplanar with the benzene ring; the dihedral angle between the two planes is 11.08 (12)°. The crystal structure is characterized by C-HO interactions. Weak intramolecular C-HO hydrogen bonds also occur.

Related literature

For general background to chalcones, see: Chun et al. (2001); Horng et al. (2003); Lopez et al. (2001); Zubieta et al. (2001); Howard et al. (2004); Petrash (2004); Lu et al. (2010). Mei et al. (2003). For related structures, see: Liang et al. (2011); Alex et al. (1993); Li & Su (1993).

Experimental

Crystal data

C₁₆H₁₅BrO₄S
M_r = 383.25
Monoclinic, P 2₁ /c
a = 8.114 (5) Å
b = 12.775 (5) Å
c = 15.404 (5) Å
= 98.813 (5)°
V = 1577.9 (13) Å³
Z = 4
Mo K radiation
= 2.75 mm^-1
T = 293 K
0.22 × 0.15 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur diffractometer
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.228, T_max = 1.000
16471 measured reflections
2784 independent reflections
2343 reflections with I > 2(I)
R_int = 0.042

Refinement

R[F² > 2(F²)] = 0.033
wR(F²) = 0.082
S = 1.06
2784 reflections
199 parameters
H-atom parameters constrained
_max = 0.33 e Å^-3
_min = -0.59 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C8-H8BO5	0.96	2.23	2.861 (4)	122
C9-H9BO4	0.96	2.38	2.985 (4)	120
C21-H21O6ⁱ	0.93	2.41	3.322 (4)	165
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZJ2039 ).

Acknowledgements

The authors thank Professor T. N. Guru Row, SSCU, IISc, Bangalore, for support of the X-ray data collection. KS thanks the GITAM University, Visakhapatnam, Andhrapradesh, for financial support under a minor reasearch project.

References

Alex, G., Srinivasan, S., Krishnasamy, V., Suresh, R. V., Iyer, R. & Iyer, P. R. (1993). Acta Cryst. C49, 70-72.
Chun, N. L., Hsin, K. H., Horng, H. K., Mei, F. H., Hsien, C. L., Ya, L. C., Mei, I. C., Jaw, J. K., Jih, P. W. & Che, M. T. (2001). Drug Dev Res. 53, 9-14.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
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Horng, H. K., Lo, T. T., Kun, L. Y., Cheng, T. L., Jih, P. W. & Chun, N. L. (2003). Bioorg Med Chem. 1, 105-111.
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Liang, Y.-S., Mu, S., Wang, J.-Y. & Liu, D.-K. (2011). Acta Cryst. E67, o830.
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organic compounds