2-(Benzo[d]thia­zol-2-ylsulfon­yl)-1-(4-bromo­phen­yl)ethanone

Loghmani-Khouzani, H.; Hajiheidari, D.; Robinson, W.T.; Kia, R.

doi:10.1107/S1600536809053112

Volume 66
Part 1
Page o209
January 2010

Received 9 December 2009
Accepted 10 December 2009
Online 19 December 2009

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.004 Å
R = 0.036
wR = 0.089
Data-to-parameter ratio = 12.9
Details

2-(Benzo[d]thiazol-2-ylsulfonyl)-1-(4-bromophenyl)ethanone

Hossein Loghmani-Khouzani,^a ^* Dariush Hajiheidari,^a Ward T. Robinson ^b and Reza Kia ^c ⁺

^aChemistry Department, University of Isfahan, Isfahan, 81746-73441, Iran,^bUniversity of Malaya, Department of Chemistry, 50603, Kuala Lumpur, Malaysia, and ^cDepartment of Chemistry, Science and Research Campus, Islamic Azad University, Poonak, Tehran, Iran
Correspondence e-mail: loghmani_h@yahoo.com

In the title molecule, C₁₅H₁₀BrNO₃S₂, the dihedral angle between the benzothiazole ring system and the benzene ring is 67.57 (12)°. The crystal structure is stabilized by weak intermolecular C-HO interactions. In addition, there is an intermolecular BrC [3.379 (3) Å] contact which is shorter than the sum of the van der Waals radii of these atoms.

Related literature

For bond-length data, see Allen et al. (1987). For the applications of related compounds in organic synthesis, see: Marco et al. (1995); Fuju et al. (1988); Ni et al. (2006); Grossert et al. (1984); Oishi et al. (1988); Antane et al. (2004). For the biological activity of related compounds see, Padmavathi et al. (2008). For related structures see: Loghmani-Khouzani et al. (2008, 2009a,b); Munoz et al. (2005); Suryakiran et al. (2007).

Experimental

Crystal data

C₁₅H₁₀BrNO₃S₂
M_r = 396.27
Monoclinic, P 2₁ /n
a = 5.6695 (10) Å
b = 24.489 (4) Å
c = 10.7042 (19) Å
= 94.178 (3)°
V = 1482.2 (5) Å³
Z = 4
Mo K radiation
= 3.07 mm^-1
T = 296 K
0.42 × 0.30 × 0.05 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.363, T_max = 0.864
6602 measured reflections
2564 independent reflections
2140 reflections with I > 2(I)
R_int = 0.038

Refinement

R[F² > 2(F²)] = 0.036
wR(F²) = 0.089
S = 1.03
2564 reflections
199 parameters
H-atom parameters constrained
_max = 0.65 e Å^-3
_min = -0.84 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C4-H4AO2ⁱ	0.93	2.56	3.420 (4)	154
C8-H8AO1ⁱⁱ	0.97	2.37	3.289 (3)	158
C8-H8BO1ⁱⁱⁱ	0.97	2.50	3.241 (4)	133
C14-H14AO2^iv	0.93	2.56	3.226 (4)	128
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x, -y+1, -z; (iii) x+1, y, z; (iv) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2971 ).

Acknowledgements

We thank the University of Isfahan and the University of Malaya for supporting this work.

References

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.
Antane, S., Bernotas, R., Li, Y., David, M. R. & Yan, Y. (2004). Synth. Commun. 34, 2443-2449.
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Fuju, M., Nakamura, K., Mekata, H., Oka, S. & Ohno, A. (1988). Bull. Chem. Soc. Jpn, 61, 495-500.
Grossert, J. S., Dubey, P. K., Gill, G. H., Cameron, T. S. & Gardner, P. A. (1984). Can. J. Chem. 62, 798-807.
Loghmani-Khouzani, H., Hajiheidari, D., Robinson, W. T., Abdul Rahman, N. & Kia, R. (2009a). Acta Cryst. E65, o2287.
Loghmani-Khouzani, H., Hajiheidari, D., Robinson, W. T., Abdul Rahman, N. & Kia, R. (2009b). Acta Cryst. E65, o2441.
Loghmani-Khouzani, H., Poorheravi, M. R., Sadeghi, M. M., Caggiano, L. & Jackson, R. F. W. (2008). Tetrahedron, 64, 7419-7425.
Marco, J. L., Fernandez, I., Khira, N., Fernandez, P. & Romero, A. J. (1995). J. Org. Chem. 60, 6678-6679.
Munoz, L., Rosa, E., Pilar Bosch, M. & Guerrero, A. (2005). Tetrahedron Lett. 46, 311-313.
Ni, C., Li, Y. & Hu, J. (2006). J. Org. Chem. 71, 6829-6833.
Oishi, Y., Watanabe, T., Kusa, K., Kazama, M. & Koniya, K. (1988). Jpn Patent 1988 JP63 243 067, 212359.
Padmavathi, V., Thriveni, T., Sudhakar Reddy, G. & Deepti, D. (2008). Eur. J. Med. Chem. 43, 917-924.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Suryakiran, N., Prabhakar, P., Reddy, T. S., Mahesh, K. C., Rajesh, K. & Venkateswarlu, Y. (2007). Tetrahedron Lett. 48, 877-881.

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