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Volume 69 
Part 1 
Page o66  
January 2013  

Received 25 November 2012
Accepted 4 December 2012
Online 12 December 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.036
wR = 0.100
Data-to-parameter ratio = 13.5
Details
Open access

6-(3-Chlorophenyl)imidazo[2,1-b][1,3,4]thiadiazole

aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India,bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India
Correspondence e-mail: jjasinski@keene.edu

In the title compound, C10H8ClN3S, the dihedral angle between the mean planes of the benzene and imidazo[2,1-b][1,3,4]thiadiazole rings is 6.0 (9)°. In the crystal, molecules are assembled by the formation of centrosymmetric dimers by [pi]-stacking of the thiadiazole and benzene rings of neighboring molecules [centroid-centroid distance = 3.6938 (11) Å] along [010].

Related literature

For related imidazothiadiazole derivatives and their pharmacological potential, see: Palagiano et al. (1995[Palagiano, F., Arenare, L., Laraschi, E., de Caprariis, P., Abignente, E., Amico, M. D., Filippelli, W. & Rossi, F. (1995). Eur. J. Med. Chem. 30, 901-910.]). For related structures, see: Banu et al. (2011a[Banu, A., Begum, N. S., Lamani, R. S. & Khazi, I. M. (2011a). Acta Cryst. E67, o779.],b[Banu, A., Ziaulla, M., Begum, N. S., Lamani, R. S. & Khazi, I. M. (2011b). Acta Cryst. E67, o617-o618.]); Fun et al. (2011a[Fun, H.-K., Yeap, C. S., Prasad, D. J., Castelino, P. A. & Anitha, V. V. (2011a). Acta Cryst. E67, o255.],b[Fun, H.-K., Hemamalini, M., Prasad, D. J., Nagaraja, G. K. & Anitha, V. V. (2011b). Acta Cryst. E67, o207.]). For standard bond lengths, see Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C10H6ClN3S

  • Mr = 235.70

  • Monoclinic, P 21 /n

  • a = 5.43804 (19) Å

  • b = 12.4222 (4) Å

  • c = 14.1684 (4) Å

  • [beta] = 100.269 (3)°

  • V = 941.77 (5) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 5.37 mm-1

  • T = 173 K

  • 0.26 × 0.12 × 0.06 mm

Data collection
  • Agilent Xcalibur (Eos, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED Agilent Technologies, Yarnton, England.]) Tmin = 0.691, Tmax = 1.000

  • 5495 measured reflections

  • 1846 independent reflections

  • 1650 reflections with I > 2[sigma](I))

  • Rint = 0.046

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.100

  • S = 1.06

  • 1846 reflections

  • 137 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.36 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED Agilent Technologies, 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2414 ).


Acknowledgements

ASP thanks the UOM for research facilities. JPJ acknowledges the NSF-MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO and CrysAlis RED Agilent Technologies, Yarnton, England.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Banu, A., Begum, N. S., Lamani, R. S. & Khazi, I. M. (2011a). Acta Cryst. E67, o779.  [CSD] [CrossRef] [details]
Banu, A., Ziaulla, M., Begum, N. S., Lamani, R. S. & Khazi, I. M. (2011b). Acta Cryst. E67, o617-o618.  [CrossRef] [details]
Fun, H.-K., Hemamalini, M., Prasad, D. J., Nagaraja, G. K. & Anitha, V. V. (2011b). Acta Cryst. E67, o207.  [CrossRef] [details]
Fun, H.-K., Yeap, C. S., Prasad, D. J., Castelino, P. A. & Anitha, V. V. (2011a). Acta Cryst. E67, o255.  [CSD] [CrossRef] [details]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Palagiano, F., Arenare, L., Laraschi, E., de Caprariis, P., Abignente, E., Amico, M. D., Filippelli, W. & Rossi, F. (1995). Eur. J. Med. Chem. 30, 901-910.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o66  [ doi:10.1107/S1600536812049793 ]

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