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Volume 69 
Part 7 
Page o1124  
July 2013  

Received 12 May 2013
Accepted 11 June 2013
Online 19 June 2013

Key indicators
Single-crystal X-ray study
T = 292 K
Mean [sigma](C-C) = 0.003 Å
R = 0.043
wR = 0.109
Data-to-parameter ratio = 14.9
Details
Open access

{2-[(1,3-Benzothiazol-2-yl)methoxy]-5-chlorophenyl}(4-chlorophenyl)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, C21H13Cl2NO2S, the benzothiazole ring makes dihedral angles of 0.94 (1) and 70.65 (5)° with the 4-chlorophenylmethanone unit and the 5-chlorophenyl ring, respectively. The dihedral angle between the 4-chlorophenylmethanone unit and the 5-chlorophenyl ring is 66.20 (5)°. The crystal structure consists of dimeric units generated by C-H...N hydrogen bonds, further linked by C-H...O and C-H...[pi] interactions, leading to a three-dimensional network.

Related literature

For crystal structures of benzothiazole derivatives, see: Venugopala et al. (2012[Venugopala, K. N., Nayak, S. K., Govender, T., Kruger, H. G. & Maguire, G. E. M. (2012). Acta Cryst. E68, o3125.]); Nayak et al. (2013[Nayak, S. K., Venugopala, K. N., Govender, T., Kruger, H. G. & Maguire, G. E. M. (2013). Acta Cryst. E69, o70.]). For background to the applications of benzothiazole derivatives, see: Rana et al. (2007[Rana, A., Siddiqui, N. & Khan, S. A. (2007). Indian 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.]); Kelarev et al. (2003[Kelarev, V. I., Kobrakov, K. I. & Rybina, I. I. (2003). Chem. Heterocycl. Compd, 39, 1267-1306.]); Telvekar et al. (2012[Telvekar, V. N., Bairwa, V. K., Satardekar, K. & Bellubi, A. (2012). Bioorg. Med. Chem. Lett. 22, 649-652.]).

[Scheme 1]

Experimental

Crystal data
  • C21H13Cl2NO2S

  • Mr = 414.29

  • Monoclinic, P 21 /n

  • a = 13.6452 (4) Å

  • b = 7.47005 (19) Å

  • c = 18.7286 (6) Å

  • [beta] = 105.772 (3)°

  • V = 1837.14 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.48 mm-1

  • T = 292 K

  • 0.23 × 0.21 × 0.14 mm

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

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.897, Tmax = 0.935

  • 18937 measured reflections

  • 3602 independent reflections

  • 2544 reflections with I > 2[sigma](I)

  • Rint = 0.047

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.109

  • S = 1.08

  • 3602 reflections

  • 241 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

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

D-H...A D-H H...A D...A D-H...A
C5-H5...O2i 0.93 2.56 3.429 (3) 157
C17-H17...N1ii 0.93 2.62 3.442 (3) 148
C18-H18...Cgiii 0.93 2.83 3.682 (2) 152
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (ii) -x+1, -y+1, -z+1; (iii) x, y-1, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis 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 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: LX2286 ).


Acknowledgements

We are thankful to SSCU, IISc, India for the Oxford Diffraction facility funded under DST-FIST (Level II) and are grateful to the 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.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
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.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [IUCr Journals]
Nayak, S. K., Venugopala, K. N., Govender, T., Kruger, H. G. & Maguire, G. E. M. (2013). Acta Cryst. E69, o70.  [CSD] [CrossRef] [IUCr Journals]
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Oxford Diffraction (2010). 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.  [Web of Science] [CSD] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Telvekar, V. N., Bairwa, V. K., Satardekar, K. & Bellubi, A. (2012). Bioorg. Med. Chem. Lett. 22, 649-652.  [CrossRef] [ChemPort] [PubMed]
Venugopala, K. N., Nayak, S. K., Govender, T., Kruger, H. G. & Maguire, G. E. M. (2012). Acta Cryst. E68, o3125.  [CSD] [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, o1124  [ doi:10.1107/S1600536813016243 ]

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