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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 [sigma](C-C) = 0.004 Å
R = 0.033
wR = 0.082
Data-to-parameter ratio = 14.0
Details
Open access

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

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-H...O interactions. Weak intramolecular C-H...O hydrogen bonds also occur.

Related literature

For general background to chalcones, see: Chun et al. (2001[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.]); Horng et al. (2003[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.]); Lopez et al. (2001[Lopez, S. N., Castelli, M. V., Zacchino, S. A., Dominguez, J. N., Lobo, G., Charris, C. J., Cortés, J. C., Ribas, J. C., Devia, C., Rodríguez, A. M. & Enriz, R. D. (2001). Bioorg. Med. Chem. 9, 1999-2013.]); Zubieta et al. (2001[Zubieta, C., He, X. Z., Dixon, R. A. & Noel, J. P. (2001). Nat. Struct. Biol. 8, 271-279.]); Howard et al. (2004[Howard, E. I., Sanishvili, R., Cachau, R. E., Mitschler, A., Chevrier, B., Barth, P., Lamour, V., Van Zandt, M., Sibley, E., Bon, C., Moras, D., Schneider, T. R., Joachimiak, A. & Podjarny, A. (2004). Proteins, 55, 792-804.]); Petrash (2004[Petrash, J. M. (2004). Cell. Mol. Life Sci. 61, 737-749.]); Lu et al. (2010[Lu, Y., Wang, Y. & Zhu, W. (2010). Phys. Chem. Chem. Phys. 12 4543-4551.]). Mei et al. (2003[Mei, L., Prapon, W., Simon, L. C., Agnes, L. C. T. & Mei, L. G. (2003). Bioorg. Med. Chem. 11, 2729-2738.]). For related structures, see: Liang et al. (2011)[Liang, Y.-S., Mu, S., Wang, J.-Y. & Liu, D.-K. (2011). Acta Cryst. E67, o830.]; Alex et al. (1993[Alex, G., Srinivasan, S., Krishnasamy, V., Suresh, R. V., Iyer, R. & Iyer, P. R. (1993). Acta Cryst. C49, 70-72.]); Li & Su (1993[Li, Z. & Su, G. (1993). Acta Cryst. C49, 1075-1077.]).

[Scheme 1]

Experimental

Crystal data
  • C16H15BrO4S

  • Mr = 383.25

  • Monoclinic, P 21 /c

  • a = 8.114 (5) Å

  • b = 12.775 (5) Å

  • c = 15.404 (5) Å

  • [beta] = 98.813 (5)°

  • V = 1577.9 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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.]) Tmin = 0.228, Tmax = 1.000

  • 16471 measured reflections

  • 2784 independent reflections

  • 2343 reflections with I > 2[sigma](I)

  • Rint = 0.042

Refinement
  • R[F2 > 2[sigma](F2)] = 0.033

  • wR(F2) = 0.082

  • S = 1.06

  • 2784 reflections

  • 199 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.33 e Å-3

  • [Delta][rho]min = -0.59 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C8-H8B...O5 0.96 2.23 2.861 (4) 122
C9-H9B...O4 0.96 2.38 2.985 (4) 120
C21-H21...O6i 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[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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and CAMERON (Watkin et al., 1993[Watkin, D. J., Pearce, L. & Prout, C. K. (1993). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).


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.  [CrossRef] [details]
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.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
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.
Howard, E. I., Sanishvili, R., Cachau, R. E., Mitschler, A., Chevrier, B., Barth, P., Lamour, V., Van Zandt, M., Sibley, E., Bon, C., Moras, D., Schneider, T. R., Joachimiak, A. & Podjarny, A. (2004). Proteins, 55, 792-804.  [CrossRef] [PubMed] [ChemPort]
Li, Z. & Su, G. (1993). Acta Cryst. C49, 1075-1077.  [CrossRef] [details]
Liang, Y.-S., Mu, S., Wang, J.-Y. & Liu, D.-K. (2011). Acta Cryst. E67, o830.  [CSD] [CrossRef] [details]
Lopez, S. N., Castelli, M. V., Zacchino, S. A., Dominguez, J. N., Lobo, G., Charris, C. J., Cortés, J. C., Ribas, J. C., Devia, C., Rodríguez, A. M. & Enriz, R. D. (2001). Bioorg. Med. Chem. 9, 1999-2013.  [PubMed] [ChemPort]
Lu, Y., Wang, Y. & Zhu, W. (2010). Phys. Chem. Chem. Phys. 12 4543-4551.  [ISI] [CrossRef] [ChemPort] [PubMed]
Mei, L., Prapon, W., Simon, L. C., Agnes, L. C. T. & Mei, L. G. (2003). Bioorg. Med. Chem. 11, 2729-2738.  [PubMed]
Oxford Diffraction (2010). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England.
Petrash, J. M. (2004). Cell. Mol. Life Sci. 61, 737-749.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Watkin, D. J., Pearce, L. & Prout, C. K. (1993). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.
Zubieta, C., He, X. Z., Dixon, R. A. & Noel, J. P. (2001). Nat. Struct. Biol. 8, 271-279.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2012). E68, o61  [ doi:10.1107/S1600536811052202 ]

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