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

Praveen, A.S.; Jasinski, J.P.; Krauss, S.T.; Yathirajan, H.S.; Narayana, B.

doi:10.1107/S1600536812049793

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 (C-C) = 0.003 Å
R = 0.036
wR = 0.100
Data-to-parameter ratio = 13.5
Details

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

A.S. Praveen,^a Jerry P. Jasinski,^b ^* Shannon T. Krauss,^b H. S. Yathirajan ^a and B. Narayana ^c

^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). For related structures, see: Banu et al. (2011a,b); Fun et al. (2011a,b). For standard bond lengths, see Allen et al. (1987).

Experimental

Crystal data

C₁₀H₆ClN₃S
M_r = 235.70
Monoclinic, P 2₁ /n
a = 5.43804 (19) Å
b = 12.4222 (4) Å
c = 14.1684 (4) Å
= 100.269 (3)°
V = 941.77 (5) Å³
Z = 4
Cu K radiation
= 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) T_min = 0.691, T_max = 1.000
5495 measured reflections
1846 independent reflections
1650 reflections with I > 2(I))
R_int = 0.046

Refinement

R[F² > 2(F²)] = 0.036
wR(F²) = 0.100
S = 1.06
1846 reflections
137 parameters
H-atom parameters constrained
_max = 0.36 e Å^-3
_min = -0.23 e Å^-3

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006); 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.
Banu, A., Ziaulla, M., Begum, N. S., Lamani, R. S. & Khazi, I. M. (2011b). Acta Cryst. E67, o617-o618.
Fun, H.-K., Hemamalini, M., Prasad, D. J., Nagaraja, G. K. & Anitha, V. V. (2011b). Acta Cryst. E67, o207.
Fun, H.-K., Yeap, C. S., Prasad, D. J., Castelino, P. A. & Anitha, V. V. (2011a). Acta Cryst. E67, o255.
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.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds