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Volume 69 
Part 11 
Page o1701  
November 2013  

Received 17 October 2013
Accepted 20 October 2013
Online 26 October 2013

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.002 Å
R = 0.038
wR = 0.093
Data-to-parameter ratio = 20.3
Details
Open access

6-(4-Chloro­phen­yl)-3-methyl­imidazo[2,1-b]thia­zole

aDepartment of Chemistry and Chemical Technology, Togliatti State University, 14 Belorusskaya St, Togliatti 445667, Russian Federation,bDepartment of Organic, Bioorganic and Medicinal Chemistry, Samara State University, 1 Academician Pavlov St, Samara 443011, Russian Federation, and cX-Ray Structural Centre, A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street, B-334, Moscow 119991, Russian Federation
Correspondence e-mail: a.s.bunev@gmail.com

In the title compound, C12H9ClN2S, the imidazo[2,1-b]thia­zole fragment is planar (r.m.s. deviation = 0.003 Å), and the benzene ring is twisted slightly [by 5.65 (6)°] relative to this moiety. In the crystal, mol­ecules are linked by [pi]-[pi] stacking inter­actions into columns along [010]. The mol­ecules within the columns are arranged alternatively by their planar rotation of 180°. Thus, in the columns, there are the two types of [pi]-[pi] stacking inter­actions, namely, (i) between two imidazo[2,1-b]thia­zole fragments [inter­planar distance = 3.351 (2) Å] and (ii) between an imidazo[2,1-b]thia­zole fragment and the phenyl ring [inter­planar distance = 3.410 (5) Å]. There are no short contacts between the columns.

Related literature

For the synthesis and properties of related compounds containing an imidazo[2,1-b]thia­zole moiety, see: Raeymaekers et al. (1966[Raeymaekers, A. H. M., Allewijn, F. T. N., Vandenberk, J., Demoen, P. J. A., van Offenwert, T. T. T. & Janssen, P. A. (1966). J. Med. Chem. 9, 545-551.]); Metaye et al. (1992[Metaye, T., Millet, C., Kraimps, J. L., Saunier, B., Barbier, J. & Begon, F. (1992). Biochem. Pharmacol. 43, 1507-1511.]); Carpenter et al. (2003[Carpenter, A. J., Cooper, J. P., Handlon, A. L., Hertzog, D. L., Hyman, C. E., Guo, Y. C., Speake, J. D. & Witty, D. R. (2003). Patent WO03033476.]); Milne et al. (2007[Milne, J. C., Lambert, P. D., Schenk, S., Carney, D. P., Smith, J. J., Gagne, D. J., Jin, L., Boss, O., Perni, R. B., Vu, C. B., Bemis, J. E., Xie, R., Disch, J. S., Ng, P. Y., Nunes, J. J., Lynch, A. V., Yang, H. Y., Galonek, H., Israelian, K., Choy, W., Iffland, A., Lavu, S., Medvedik, O., Sinclair, D. A., Olefsky, J. M., Jirousek, M. R., Elliott, P. J. & Westphal, C. H. (2007). Nature, 450, 712-716.]); Scribner et al. (2008[Scribner, A., Meitz, S., Fisher, M., Wyvratt, M., Leavitt, P., Liberator, P., Gurnett, A., Brown, C., Mathew, J., Thompson, D., Schmatz, D. & Biftu, T. (2008). Bioorg. Med. Chem. Lett. 18, 5263-5267.]); Chorell et al. (2010[Chorell, E., Pinkner, J. S., Phan, G., Edvinsson, S., Buelens, F., Remaut, H., Waksman, G., Hultgren, S. J. & Almqvist, F. (2010). J. Med. Chem. 53, 5690-5695.]); Guzeldemirci & Kucukbasmaci (2010[Guzeldemirci, N. U. & Kucukbasmaci, O. (2010). Eur. J. Med. Chem. 45, 63-68.]); Budriesi et al. (2011[Budriesi, R., Ioan, P., Leoni, A., Pedemonte, N., Locatelli, A., Micucci, M., Chiarini, A. & Galietta, L. J. V. (2011). J. Med. Chem. 54, 3885-3894.]); Yousefi et al. (2011[Yousefi, B. H., Manook, A., Drzezga, A., von Reutern, B., Schwaiger, M., Wester, H. J. & Henriksen, G. (2011). J. Med. Chem. 54, 949-956.]).

[Scheme 1]

Experimental

Crystal data
  • C12H9ClN2S

  • Mr = 248.73

  • Triclinic, [P \overline 1]

  • a = 7.0624 (5) Å

  • b = 7.7132 (5) Å

  • c = 10.3460 (7) Å

  • [alpha] = 93.353 (1)°

  • [beta] = 90.107 (1)°

  • [gamma] = 98.832 (1)°

  • V = 555.92 (7) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.50 mm-1

  • T = 120 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2003[Bruker (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.864, Tmax = 0.906

  • 6927 measured reflections

  • 2963 independent reflections

  • 2306 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.093

  • S = 1.05

  • 2963 reflections

  • 146 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.38 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2417 ).


Acknowledgements

The authors are grateful to the Ministry of Education and Science of the Russian Federation (State program No. 3.1168.2011).

References

Bruker (2001). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Budriesi, R., Ioan, P., Leoni, A., Pedemonte, N., Locatelli, A., Micucci, M., Chiarini, A. & Galietta, L. J. V. (2011). J. Med. Chem. 54, 3885-3894.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Carpenter, A. J., Cooper, J. P., Handlon, A. L., Hertzog, D. L., Hyman, C. E., Guo, Y. C., Speake, J. D. & Witty, D. R. (2003). Patent WO03033476.
Chorell, E., Pinkner, J. S., Phan, G., Edvinsson, S., Buelens, F., Remaut, H., Waksman, G., Hultgren, S. J. & Almqvist, F. (2010). J. Med. Chem. 53, 5690-5695.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Guzeldemirci, N. U. & Kucukbasmaci, O. (2010). Eur. J. Med. Chem. 45, 63-68.  [Web of Science] [PubMed] [ChemPort]
Metaye, T., Millet, C., Kraimps, J. L., Saunier, B., Barbier, J. & Begon, F. (1992). Biochem. Pharmacol. 43, 1507-1511.  [CrossRef] [PubMed] [ChemPort] [Web of Science]
Milne, J. C., Lambert, P. D., Schenk, S., Carney, D. P., Smith, J. J., Gagne, D. J., Jin, L., Boss, O., Perni, R. B., Vu, C. B., Bemis, J. E., Xie, R., Disch, J. S., Ng, P. Y., Nunes, J. J., Lynch, A. V., Yang, H. Y., Galonek, H., Israelian, K., Choy, W., Iffland, A., Lavu, S., Medvedik, O., Sinclair, D. A., Olefsky, J. M., Jirousek, M. R., Elliott, P. J. & Westphal, C. H. (2007). Nature, 450, 712-716.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Raeymaekers, A. H. M., Allewijn, F. T. N., Vandenberk, J., Demoen, P. J. A., van Offenwert, T. T. T. & Janssen, P. A. (1966). J. Med. Chem. 9, 545-551.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
Scribner, A., Meitz, S., Fisher, M., Wyvratt, M., Leavitt, P., Liberator, P., Gurnett, A., Brown, C., Mathew, J., Thompson, D., Schmatz, D. & Biftu, T. (2008). Bioorg. Med. Chem. Lett. 18, 5263-5267.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Yousefi, B. H., Manook, A., Drzezga, A., von Reutern, B., Schwaiger, M., Wester, H. J. & Henriksen, G. (2011). J. Med. Chem. 54, 949-956.  [Web of Science] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o1701  [ doi:10.1107/S1600536813028833 ]

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