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Volume 68 
Part 11 
Page o3125  
November 2012  

Received 21 August 2012
Accepted 6 October 2012
Online 13 October 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.006 Å
R = 0.059
wR = 0.200
Data-to-parameter ratio = 13.6
Details
Open access

(2-(Benzo[d]thiazol-2yl-methoxy)-5-chlorophenyl)(phenyl)methanone

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

In the title compound, C21H14ClNO2S, the dihedral angle between the benzothiazole and diphenyl methanone groups is 68.6 (2)°. The crystal structure consists of dimeric units generated by C-H...N bonds, further linked by C-H...O bonds and C-H...[pi] and [pi]-[pi] interactions [centroid-centroiddistance = 3.856 (2) Å], which lead to a criss-cross assembly parallel to (001).

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.]); 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
  • C21H14ClNO2S

  • Mr = 379.84

  • Orthorhombic, P b c a

  • a = 7.4598 (3) Å

  • b = 19.3131 (8) Å

  • c = 24.4002 (9) Å

  • V = 3515.4 (2) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.35 mm-1

  • T = 173 K

  • 0.22 × 0.16 × 0.03 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) Tmin = 0.927, Tmax = 0.990

  • 52834 measured reflections

  • 3206 independent reflections

  • 2576 reflections with I > 2[sigma](I)

  • Rint = 0.063

Refinement
  • R[F2 > 2[sigma](F2)] = 0.059

  • wR(F2) = 0.200

  • S = 1.30

  • 3206 reflections

  • 235 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.66 e Å-3

  • [Delta][rho]min = -0.33 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
C17-H17...N1i 0.95 2.56 3.432 (5) 153
C5-H5...O2ii 0.95 2.59 3.478 (5) 155
C18-H18...Cg1iii 0.95 2.62 3.433 (5) 144
Symmetry codes: (i) -x+1, -y, -z+1; (ii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]; (iii) x+1, y, z.

Data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO-SMN; 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, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) 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: BG2479 ).


Acknowledgements

The authors wish to thank the University of KwaZulu-Natal, South Africa, for facilities and Dr Hong Su, Department of Chemistry, University of Cape Town, for the data collection.

References

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
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]
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
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.


Acta Cryst (2012). E68, o3125  [ doi:10.1107/S1600536812041888 ]

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