3-{[5-(4-Bromo­phen­yl)imidazo[2,1-b][1,3,4]thia­diazol-2-yl]meth­yl}-1,2-benzoxazole

Banu, A.; Ziaulla, M.; Begum, N.S.; Lamani, R.S.; Khazi, I.M.

doi:10.1107/S1600536810052232

Volume 67
Part 1
Page o154
January 2011

Received 15 November 2010
Accepted 13 December 2010
Online 18 December 2010

Key indicators
Single-crystal X-ray study
T = 423 K
Mean (C-C) = 0.006 Å
R = 0.052
wR = 0.142
Data-to-parameter ratio = 15.2
Details

3-{[5-(4-Bromophenyl)imidazo[2,1-b][1,3,4]thiadiazol-2-yl]methyl}-1,2-benzoxazole

Afshan Banu,^a Mohamed Ziaulla,^a Noor Shahina Begum,^a ^* Ravi S. Lamani ^b and I. M. Khazi ^b

^aDepartment of Studies in Chemistry, Bangalore University, Bangalore 560 001, India, and ^bDepartment of Chemistry, Karnatak University, Dharwad 580 003, India
Correspondence e-mail: noorsb@rediffmail.com

In the title compound, C₁₈H₁₁BrN₄OS, the imidazothiadiazole and benzisoxazole rings are individually planar with maximum deviations of 0.025 (3) 0.015 (4) Å, respectively, and are inclined at an angle of 23.51 (7)° with respect to each other. The planes of the imidazothiadiazole and bromophenyl rings are inclined at an angle of 27.34 (3)°. In the crystal, intermolecular C-HN interactions result in chains of molecules along the b and c axes. Moreover, C-HO interactions result in centrosymmetric head-to-head dimers with R₂²(24) graph-set motifs. The molecular packing is further stabilized by [pi] - [pi] stacking interactions between the imidazole rings with a shortest centroid-centroid distance of 3.492 (3) Å. In addition, C-H [pi] interactions are observed in the crystal structure.

Related literature

For the biological activity of benzisoxazole derivatives, see: Priya et al. (2005). For the preparation of the title compound, see: Lamani et al. (2009). For a related structure, see: Sun & Zhang (2009). For graph-set notation, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₈H₁₁BrN₄OS
M_r = 411.28
Monoclinic, C 2/c
a = 38.985 (17) Å
b = 5.764 (3) Å
c = 14.925 (6) Å
= 109.191 (13)°
V = 3167 (2) Å³
Z = 8
Mo K radiation
= 2.74 mm^-1
T = 423 K
0.18 × 0.16 × 0.16 mm

Data collection

Bruker SMART APEX CCD detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998) T_min = 0.638, T_max = 0.668
8879 measured reflections
3432 independent reflections
2534 reflections with I > 2(I)
R_int = 0.081

Refinement

R[F² > 2(F²)] = 0.052
wR(F²) = 0.142
S = 1.02
3432 reflections
226 parameters
H-atom parameters constrained
_max = 1.10 e Å^-3
_min = -1.02 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 and Cg5 are the centroids of the C1-C6 and C13-C18 rings, respectively.

D-HA	D-H	HA	DA	D-HA
C2-H2O1ⁱ	0.93	2.38	3.219 (6)	150
C8-H8N1ⁱⁱ	0.93	2.60	3.469 (6)	156
C11-H11BN1ⁱⁱⁱ	0.97	2.48	3.358 (6)	150
C4-H4Cg5ⁱⁱⁱ	0.93	2.96	3.554 (5)	123
C18-H18Cg4ⁱⁱⁱ	0.93	2.83	3.496 (5)	130
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) x, y+1, z; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1996); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2359 ).

Acknowledgements

NSB is thankful to the University Grants Commission (UGC), India, for financial assistance and the Department of Science and Technology, (DST), India, for the data collection facility under the IRHPA-DST program.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker Axs Inc., Madison, Wisconcin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Lamani, R. S., Shetty, N. S., Ravindra, R. & Khazi, I. A. M. (2009). Eur. J. Med. Chem. 44, 2828-2833.
Priya, B. S., Basappa., Swamy, S. N., Rangappa, K. S. (2005). Bioorg. Med. Chem. 13, 2623-2628.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sun, Y. & Zhang, H.-H. (2009). Acta Cryst. E65, o1647.
Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.

organic compounds