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Volume 69 
Part 7 
Pages o1007-o1008  
July 2013  

Received 13 May 2013
Accepted 27 May 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 292 K
Mean [sigma](C-C) = 0.006 Å
R = 0.053
wR = 0.118
Data-to-parameter ratio = 14.5
Details
Open access

{2-[(1,3-Benzothiazol-2-yl)methoxy]-5-fluorophenyl}(4-chlorophenyl)methanone

aSchool of Pharmacy and Pharmacology, University of KwaZulu-Natal, Durban 4000, South Africa,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, and cSchool of Chemistry and Physics, University of KwaZulu-Natal, Durban 4000, South Africa
Correspondence e-mail: venugopala@ukzn.ac.za, nksusa@gmail.com

The asymmetric unit of the title compound, C21H13ClFNO2S, contains two independent molecules with similar conformations. In the molecules, the thiazole ring is essentially planar [maximum atomic deviations = 0.014 (4) and 0.023 (5) Å] and is oriented with respect to the fluorophenyl ring and chlorophenyl rings at 9.96 (18) and 70.39 (18)° in one molecule and at 7.50 (18) and 68.43 (18)° in the other; the dihedral angles between the fluorophenyl and chlorophenyl rings are 64.9 (2) and 64.6 (2)°, respectively. Intermolecular C-H...O and C-H...F hydrogen bonds stabilize the three-dimensional supramolecular architecture. Weak C-H...[pi] and [pi]-[pi] interactions [centroid-centroid distance = 3.877 (3) Å] lead to a criss-cross molecular packing along the c axis.

Related literature

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

[Scheme 1]

Experimental

Crystal data
  • C21H13ClFNO2S

  • Mr = 397.84

  • Orthorhombic, P n a 21

  • a = 19.7280 (6) Å

  • b = 7.4755 (3) Å

  • c = 24.4847 (7) Å

  • V = 3611.0 (2) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.35 mm-1

  • T = 292 K

  • 0.18 × 0.12 × 0.08 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, Oxfordshire, England.]) Tmin = 0.939, Tmax = 0.972

  • 36561 measured reflections

  • 7100 independent reflections

  • 4182 reflections with I > 2[sigma](I)

  • Rint = 0.076

Refinement
  • R[F2 > 2[sigma](F2)] = 0.053

  • wR(F2) = 0.118

  • S = 0.99

  • 7100 reflections

  • 488 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.])

  • Flack parameter: -0.05 (8), ???? Friedel pairs

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the thiazole rings S1/C1/C6/N1/C7 and S2/C22/C27/N2/C28, respectively.

D-H...A D-H H...A D...A D-H...A
C3-H3...F1i 0.93 2.52 3.091 (6) 120
C5-H5...O2ii 0.93 2.46 3.340 (5) 158
C26-H26...O4iii 0.93 2.51 3.369 (5) 154
C18-H18...Cg1iv 0.93 2.83 3.686 (5) 154
C39-H39...Cg2v 0.93 2.82 3.619 (5) 145
Symmetry codes: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z]; (iii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]; (iv) x, y-1, z; (v) x, y+1, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, 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: XU5707 ).


Acknowledgements

We are grateful to SSCU, IISc, India, 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.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [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 PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, 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, o1007-o1008   [ doi:10.1107/S1600536813014621 ]

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