[Journal logo]

Volume 69 
Part 4 
Page o531  
April 2013  

Received 3 March 2013
Accepted 7 March 2013
Online 13 March 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
R = 0.032
wR = 0.070
Data-to-parameter ratio = 20.5
Details
Open access

3-Bromo-7-methoxy-2-phenylimidazo[2,1-b][1,3]benzothiazole

aDepartment of Chemistry and Chemical Technology, Togliatti State University, 14 Belorusskaya Street, Togliatti 445667, Russian Federation,bDepartment of Bioorganic and Medicinal Chemistry, Samara State University, 1 Academika Pavlova Street, 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 molecule, C16H11BrN2OS, the central imidazo[2,1-b][1,3]benzothiazole tricycle is essentially planar (r.m.s. deviation = 0.021 Å). The terminal phenyl ring is twisted at 36.18 (5)° from the mean plane of the tricycle. In the crystal, pairs of eak C-H...O hydrogen bonds link molecules into centrosymmetric dimers, which are further packed into stacks along the a axis.

Related literature

For applications of imidazo[2,1-b][1,3]benzothiazoles, see: Mase et al. (1988[Mase, T., Arima, H., Tomioka, K., Yamada, T. & Murase, K. (1988). Eur. J. Med. Chem. 23, 335-339.]); Ager et al. (1988[Ager, I. R., Barnes, A. C., Danswan, G. W., Hairsine, P. W., Kay, D. P., Kennewell, P. D., Matharu, S. S., Miller, P. & Robson, P. (1988). J. Med. Chem. 31, 1098-1115.]); Barchéchath et al. (2005[Barchéchath, S. D., Tawatao, R. I., Corr, V., Carson, D. I. & Cottam, H. B. (2005). J. Med. Chem. 48, 6409-6422.]); Kumbhare et al. (2011[Kumbhare, R. M., Kumar, K. V., Ramaiah, M. J., Dadmal, T., Pushpavalli, S. N., Mukhopadhyay, D., Divya, B., Devi, T. A., Kosurkar, U. & Pal-Bhadra, M. (2011). Eur. J. Med. Chem. 46, 4258-4266.]); Yousefi et al. (2011[Yousefi, B. H., Drzezga, F., Reutern, B., Manook, A., Schwaiger, H. M., Wester, H. J. & Henriksen, G. (2011). ACS Med. Chem. Lett. 2, 673-677.]); Chandak et al. (2013[Chandak, N., Bhardwaj, J. K., Sharma, R. K. & Sharma, P. K. (2013). Eur. J. Med. Chem. 59, 203-208.]). For the crystal structures of related compounds, see: Landreau et al. (2002[Landreau, C., Deniaud, D., Evain, M., Reliquet, A. & Meslin, J.-C. (2002). J. Chem. Soc. Perkin Trans. 1, pp. 741-745.]); Adib et al. (2008[Adib, M., Sheibani, E., Zhu, L.-G. & Bijanzadeh, H. R. (2008). Synlett, pp. 2941-2944.]); Fun, Asik et al. (2011[Fun, H.-K., Asik, S. I. J., Himaja, M., Munirajasekhar, D. & Sarojini, B. K. (2011). Acta Cryst. E67, o2810.]); Fun, Hemamalini et al. (2011[Fun, H.-K., Hemamalini, M., Umesha, K., Sarojini, B. K. & Narayana, B. (2011). Acta Cryst. E67, o3265-o3266.]).

[Scheme 1]

Experimental

Crystal data
  • C16H11BrN2OS

  • Mr = 359.24

  • Monoclinic, P 21 /n

  • a = 3.8346 (4) Å

  • b = 9.4848 (11) Å

  • c = 37.236 (4) Å

  • [beta] = 91.810 (2)°

  • V = 1353.6 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 3.19 mm-1

  • T = 100 K

  • 0.35 × 0.15 × 0.15 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.402, Tmax = 0.646

  • 17224 measured reflections

  • 3924 independent reflections

  • 3578 reflections with I > 2[sigma](I)

  • Rint = 0.041

Refinement
  • R[F2 > 2[sigma](F2)] = 0.032

  • wR(F2) = 0.070

  • S = 1.00

  • 3924 reflections

  • 191 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.59 e Å-3

  • [Delta][rho]min = -0.95 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C8-H8...O1i 0.95 2.56 3.465 (3) 158
Symmetry code: (i) -x+2, -y, -z+2.

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: CV5391 ).


Acknowledgements

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

References

Adib, M., Sheibani, E., Zhu, L.-G. & Bijanzadeh, H. R. (2008). Synlett, pp. 2941-2944.  [ISI] [CSD] [CrossRef]
Ager, I. R., Barnes, A. C., Danswan, G. W., Hairsine, P. W., Kay, D. P., Kennewell, P. D., Matharu, S. S., Miller, P. & Robson, P. (1988). J. Med. Chem. 31, 1098-1115.  [CrossRef] [ChemPort] [PubMed] [ISI]
Barchéchath, S. D., Tawatao, R. I., Corr, V., Carson, D. I. & Cottam, H. B. (2005). J. Med. Chem. 48, 6409-6422.  [ISI] [PubMed]
Bruker (2001). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Chandak, N., Bhardwaj, J. K., Sharma, R. K. & Sharma, P. K. (2013). Eur. J. Med. Chem. 59, 203-208.  [CrossRef] [ChemPort] [PubMed]
Fun, H.-K., Asik, S. I. J., Himaja, M., Munirajasekhar, D. & Sarojini, B. K. (2011). Acta Cryst. E67, o2810.  [CSD] [CrossRef] [details]
Fun, H.-K., Hemamalini, M., Umesha, K., Sarojini, B. K. & Narayana, B. (2011). Acta Cryst. E67, o3265-o3266.  [CSD] [CrossRef] [details]
Kumbhare, R. M., Kumar, K. V., Ramaiah, M. J., Dadmal, T., Pushpavalli, S. N., Mukhopadhyay, D., Divya, B., Devi, T. A., Kosurkar, U. & Pal-Bhadra, M. (2011). Eur. J. Med. Chem. 46, 4258-4266.  [ISI] [CrossRef] [ChemPort] [PubMed]
Landreau, C., Deniaud, D., Evain, M., Reliquet, A. & Meslin, J.-C. (2002). J. Chem. Soc. Perkin Trans. 1, pp. 741-745.  [CSD] [CrossRef]
Mase, T., Arima, H., Tomioka, K., Yamada, T. & Murase, K. (1988). Eur. J. Med. Chem. 23, 335-339.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Yousefi, B. H., Drzezga, F., Reutern, B., Manook, A., Schwaiger, H. M., Wester, H. J. & Henriksen, G. (2011). ACS Med. Chem. Lett. 2, 673-677.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o531  [ doi:10.1107/S1600536813006582 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.