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Volume 69 
Part 3 
Page o360  
March 2013  

Received 12 January 2013
Accepted 19 January 2013
Online 9 February 2013

Key indicators
Single-crystal X-ray study
T = 273 K
Mean [sigma](C-C) = 0.006 Å
R = 0.076
wR = 0.208
Data-to-parameter ratio = 14.0
Details
Open access

5-Chloro-2-(4-methoxyphenyl)-1,3-benzothiazole

aH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
Correspondence e-mail: dr.sammer.yousuf@gmail.com

In the title compound, C14H10ClNOS, the dihedral angle between the benzothiazole ring system and the methoxy-substituted benzene ring is 8.76 (16)°. In the crystal, molecules are stacked in columns along the c axis and no significant intermolecular interactions are observed.

Related literature

For the biological activity of benzothiazole compounds, see: Chohan et al. (2003[Chohan, Z. H., Pervez, H., Scozzafava, A. & Supuran, C. T. (2003). J. Chem. Soc. Pak. 25, 308-313.]); Khan et al. (2011[Khan, K. M., Rahim, F., Halim, S. A., Taha, M., Khan, M., Perveen, S., Zaheer-ul-Haq, Mesaik, M. A. & Choudhary, M. I., (2011). Bioorg. Med. Chem. 19, 4286-4294.]); Hutchinson et al. (2002[Hutchinson, I., Jennings, S. A., Vishnuvajjala, B. R., Wetsell, A. D. & Stevens, M. F. G. (2002). J. Med. Chem. 45, 744-747.]); Burger & Sawhney (1968[Burger, A. & Sawhney, S. N. (1968). J. Med. Chem. 11, 270-273.]); Palmer et al. (1971[Palmer, P. J., Trigg, R. B. & Warrington, J. V. (1971). J. Med. Chem. 14, 248-251.]). For related structures, see: Yousuf et al. (2012a[Yousuf, S., Shah, S., Ambreen, N., Khan, K. M. & Ahmad, S. (2012a). Acta Cryst. E68, o2877.],b[Yousuf, S., Shah, S., Ambreen, N., Khan, K. M. & Ahmad, S. (2012b). Acta Cryst. E68, o3057.]).

[Scheme 1]

Experimental

Crystal data
  • C14H10ClNOS

  • Mr = 275.74

  • Orthorhombic, P b c n

  • a = 29.0274 (16) Å

  • b = 14.5512 (8) Å

  • c = 5.8686 (3) Å

  • V = 2478.8 (2) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.46 mm-1

  • T = 273 K

  • 0.37 × 0.22 × 0.10 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.848, Tmax = 0.955

  • 13397 measured reflections

  • 2299 independent reflections

  • 1965 reflections with I > 2[sigma](I)

  • Rint = 0.052

Refinement
  • R[F2 > 2[sigma](F2)] = 0.076

  • wR(F2) = 0.208

  • S = 1.15

  • 2299 reflections

  • 164 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.63 e Å-3

  • [Delta][rho]min = -0.37 e Å-3

Data collection: SMART (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1996[Nardelli, M. (1996). J. Appl. Cryst. 29, 296-300.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5237 ).


Acknowledgements

The authors are thankful to the OPCW, Netherland, and the Higher Education Commission (HEC) Pakistan (project No. 1910) for their financial support.

References

Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Burger, A. & Sawhney, S. N. (1968). J. Med. Chem. 11, 270-273.  [CrossRef] [PubMed] [ISI]
Chohan, Z. H., Pervez, H., Scozzafava, A. & Supuran, C. T. (2003). J. Chem. Soc. Pak. 25, 308-313.  [ChemPort]
Hutchinson, I., Jennings, S. A., Vishnuvajjala, B. R., Wetsell, A. D. & Stevens, M. F. G. (2002). J. Med. Chem. 45, 744-747.  [ISI] [CrossRef] [PubMed] [ChemPort]
Khan, K. M., Rahim, F., Halim, S. A., Taha, M., Khan, M., Perveen, S., Zaheer-ul-Haq, Mesaik, M. A. & Choudhary, M. I., (2011). Bioorg. Med. Chem. 19, 4286-4294.
Nardelli, M. (1996). J. Appl. Cryst. 29, 296-300.  [CrossRef] [ChemPort] [ISI] [details]
Palmer, P. J., Trigg, R. B. & Warrington, J. V. (1971). J. Med. Chem. 14, 248-251.  [CrossRef] [ChemPort] [PubMed] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Yousuf, S., Shah, S., Ambreen, N., Khan, K. M. & Ahmad, S. (2012a). Acta Cryst. E68, o2877.  [CSD] [CrossRef] [details]
Yousuf, S., Shah, S., Ambreen, N., Khan, K. M. & Ahmad, S. (2012b). Acta Cryst. E68, o3057.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o360  [ doi:10.1107/S1600536813001955 ]

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