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Volume 69 
Part 1 
Page o70  
January 2013  

Received 21 November 2012
Accepted 4 December 2012
Online 12 December 2012

Key indicators
Single-crystal X-ray study
T = 292 K
Mean [sigma](C-C) = 0.004 Å
R = 0.044
wR = 0.096
Data-to-parameter ratio = 14.9
Details
Open access

[2-(1,3-Benzothiazol-2-ylmethoxy)-5-bromophenyl](4-chlorophenyl)methanone

aCenter for Nano Science and Technology@Polimi, Istituto Italiano di Tecnologia, Via Pascoli 70/3-20133 Milan, Italy,bSchool of Pharmacy and Pharmacology, University of Kwazulu-Natal, Durban 4000, South Africa, and cSchool of Chemistry and Physics, University of KwaZulu-Natal, Durban 4000, South Africa
Correspondence e-mail: nksusa@gmail.com, venugopala@ukzn.ac.za

In the title compound, C21H13BrClNO2S, the dihedral angle between the planes of the benzothiazole and chlorophenylmethanone groups is 71.34 (6)°. In the crystal, weak C-H...N hydrogen bonds lead to dimer formation, whereas Br...Cl short contacts [3.4966 (11) Å] form infinite chains along the a-axis direction. Further, the C-H...O, C-H...[pi] and [pi]-[pi] [centroid-centroid distance = 3.865 (2) Å] interactions stabilize the three-dimensional network.

Related literature

For background to the applications of benzothiazole derivatives, see: Rana et al. (2007[Rana, A., Siddiqui, N. & Khan, S. A. (2007). J. Pharm. Sci. 69, 10-17.]); Saeed et al. (2010[Saeed, S., Rashid, N., Jones, P. G., Ali, M. & Hussain, R. (2010). Eur. J. Med. Chem. 45, 1323-1331.]); Telvekar et al. (2012[Telvekar, V. N., Bairwa, V. K., Satardekar, K. & Bellubi, A. (2012). Bioorg. Med. Chem. Lett. 22, 148-155.]); Venugopala et al. (2012[Venugopala, K. N., Nayak, S. K., Govender, T., Kruger, H. G. & Maguire, G. E. M. (2012). Acta Cryst. E68, o3125.]). For their biological activity, see: Kelarev et al. (2003[Kelarev, V. I., Kobrakov, K. I. & Rybina, I. I. (2003). Chem. Heterocycl. Compd, 39, 1267-1306.]). For types of interactions involving halogens, see: Nayak et al. (2011[Nayak, S. K., Reddy, M. K., Guru Row, T. N. & Chopra, D. (2011). Cryst. Growth Des. 11, 1578-1596.]).

[Scheme 1]

Experimental

Crystal data
  • C21H13BrClNO2S

  • Mr = 458.74

  • Monoclinic, P 21 /n

  • a = 13.7746 (3) Å

  • b = 7.4918 (2) Å

  • c = 18.7016 (7) Å

  • [beta] = 106.013 (3)°

  • V = 1855.05 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 2.49 mm-1

  • T = 292 K

  • 0.21 × 0.19 × 0.06 mm

Data collection
  • Oxford Diffraction Xcalibur (Eos, Nova) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.623, Tmax = 0.865

  • 19324 measured reflections

  • 3645 independent reflections

  • 2451 reflections with I > 2[sigma](I)

  • Rint = 0.054

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.096

  • S = 1.07

  • 3645 reflections

  • 244 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.45 e Å-3

  • [Delta][rho]min = -0.43 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the thiazole ring.

D-H...A D-H H...A D...A D-H...A
C5-H5...O2i 0.93 2.58 3.446 (4) 156
C17-H17...N1ii 0.93 2.61 3.434 (4) 147
C18-H18...Cg1iii 0.93 2.82 3.666 (3) 151
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) -x+1, -y, -z; (iii) x, y-1, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 for Windows (Farrugia, 2012)[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.] and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) 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: GO2078 ).


Acknowledgements

We are thankful to the SSCU, IISc, for the Oxford Diffraction facility funded under DST-FIST (Level II) and the University of KwaZulu-Natal, South Africa, for facilities.

References

Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Kelarev, V. I., Kobrakov, K. I. & Rybina, I. I. (2003). Chem. Heterocycl. Compd, 39, 1267-1306.  [CrossRef] [ChemPort]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [details]
Nayak, S. K., Reddy, M. K., Guru Row, T. N. & Chopra, D. (2011). Cryst. Growth Des. 11, 1578-1596.  [CSD] [CrossRef] [ChemPort]
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Rana, A., Siddiqui, N. & Khan, S. A. (2007). J. Pharm. Sci. 69, 10-17.  [ChemPort]
Saeed, S., Rashid, N., Jones, P. G., Ali, M. & Hussain, R. (2010). Eur. J. Med. Chem. 45, 1323-1331.  [ISI] [CSD] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Telvekar, V. N., Bairwa, V. K., Satardekar, K. & Bellubi, A. (2012). Bioorg. Med. Chem. Lett. 22, 148-155.
Venugopala, K. N., Nayak, S. K., Govender, T., Kruger, H. G. & Maguire, G. E. M. (2012). Acta Cryst. E68, o3125.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o70  [ doi:10.1107/S1600536812049756 ]

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