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Volume 69 
Part 6 
Page o984  
June 2013  

Received 12 May 2013
Accepted 21 May 2013
Online 31 May 2013

Key indicators
Single-crystal X-ray study
T = 292 K
Mean [sigma](C-C) = 0.007 Å
R = 0.054
wR = 0.120
Data-to-parameter ratio = 15.0
Details
Open access

{2-[(1,3-Benzothiazol-2-yl)methoxy]-5-bromophenyl}(phenyl)methanone

aDepartment of Biotechnology and Food Technology, Durban University of Technology, Durban 4001, South Africa, and bEquipe Chimie du Solide et Matériaux, UMR 6226 Institut des Sciences, Université de Rennes 1, Campus de Beaulieu, Avenue du Général Leclerc, 35042 Rennes Cedex, France
Correspondence e-mail: katharigattav@dut.ac.za, nksusa@gmail.com

In the title compound, C21H14BrNO2S, the dihedral angle between the planes of the benzothiazole and phenylmethanone groups is 63.4 (2)°. In the crystal, pairs of C-H...N hydrogen bonds link the molecules to form inversion dimers, which are further linked by C-H...O interactions into chains along the c axis. C-H...[pi] and [pi]-[pi] interactions [centroid-centroid distance = 3.863 (1) Å] further stabilize the molecular assembly.

Related literature

For background to the applications of benzothiazole derivatives, see: Kelarev et al. (2003[Kelarev, V. I., Kobrakov, K. I. & Rybina, I. I. (2003). Chem. Heterocycl. Compd, 39, 1267-1306.]); Rana et al. (2007[Rana, A., Siddiqui, N. & Khan, S. A. (2007). Indian J. Pharm. Sci. 69, 10-17.]); Telvekar et al. (2012[Telvekar, V. N., Bairwa, V. K., Satardekar, K. & Bellubi, A. (2012). Bioorg. Med. Chem. Lett. 22, 148-155.]); Saeed et al. (2010[Saeed, S., Rashid, N., Jones, P. G., Ali, M. & Hussain, R. (2010). Eur. J. Med. Chem. 45, 1323-1331.]).

[Scheme 1]

Experimental

Crystal data
  • C21H14BrNO2S

  • Mr = 424.30

  • Monoclinic, P 21 /n

  • a = 15.1475 (6) Å

  • b = 7.6501 (3) Å

  • c = 15.8339 (6) Å

  • [beta] = 102.105 (3)°

  • V = 1794.03 (12) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 2.42 mm-1

  • T = 292 K

  • 0.23 × 0.21 × 0.18 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 = 0.606, Tmax = 0.670

  • 19116 measured reflections

  • 3525 independent reflections

  • 1971 reflections with I > 2[sigma](I)

  • Rint = 0.088

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

  • wR(F2) = 0.120

  • S = 0.98

  • 3525 reflections

  • 235 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.32 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the S1/C1/C6/N1/C7 ring.

D-H...A D-H H...A D...A D-H...A
C21-H21...N1i 0.93 2.55 3.398 (6) 152
C5-H5...O2ii 0.93 2.61 3.505 (6) 161
C20-H20...Cg1iii 0.93 2.68 3.459 (4) 142
Symmetry codes: (i) -x, -y+1, -z; (ii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (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: FF2107 ).


Acknowledgements

We are thankful to SSCU, IISc, India for the Oxford Diffraction facility funded under DST-FIST (Level II) and Durban University of Technology for facilities. KNV thanks the NRF South Africa for a DST/NRF Innovation Postdoctoral Fellowship.

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]
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Rana, A., Siddiqui, N. & Khan, S. A. (2007). Indian 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] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Telvekar, V. N., Bairwa, V. K., Satardekar, K. & Bellubi, A. (2012). Bioorg. Med. Chem. Lett. 22, 148-155.


Acta Cryst (2013). E69, o984  [ doi:10.1107/S1600536813014086 ]

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