2-(2-Nitro­phen­yl)-1,3-benzothia­zole

Vijayakumar, S.; Murugavel, S.; Selvakumar, R.; Bakthadoss, M.

doi:10.1107/S1600536812029844

Volume 68
Part 8
Page o2362
August 2012

Received 25 June 2012
Accepted 30 June 2012
Online 7 July 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R = 0.039
wR = 0.113
Data-to-parameter ratio = 20.0
Details

2-(2-Nitrophenyl)-1,3-benzothiazole

S. Vijayakumar,^a S. Murugavel,^b ^* R. Selvakumar ^c and M. Bakthadoss ^c ⁺

^aDepartment of Physics, Sri Balaji Chokkalingam Engineering College, Arni, Thiruvannamalai 632 317, India,^bDepartment of Physics, Thanthai Periyar Government Institute of Technology, Vellore 632 002, India, and ^cDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
Correspondence e-mail: smurugavel27@gmail.com

In the title compound, C₁₃H₈N₂O₂S, the essentially planar benzothiazole system [maximum deviation = -0.012 (1) Å for the S atom] is oriented at a dihedral angle of 48.3 (1)° with respect to the benzene ring. The nitro group is substantially twisted from the plane of its attached benzene ring [dihedral angle = 52.0 (1)°]. The crystal packing features C-HO hydrogen bonds, which generate C(6) helical chains propagating along [010]. Weak C-H [pi] interactions also occur in the crystal.

Related literature

For the pharmacological activity of benzothiazole derivatives, see: Repic et al. (2001); Schwartz et al. (1992). For related structures, see: Lakshmanan et al. (2011); Zhang et al. (2008).

Experimental

Crystal data

C₁₃H₈N₂O₂S
M_r = 256.27
Monoclinic, P 2₁ /c
a = 7.6092 (2) Å
b = 12.7854 (3) Å
c = 11.9938 (3) Å
= 90.556 (2)°
V = 1166.78 (5) Å³
Z = 4
Mo K radiation
= 0.27 mm^-1
T = 293 K
0.24 × 0.22 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.937, T_max = 0.958
14037 measured reflections
3258 independent reflections
2559 reflections with I > 2(I)
R_int = 0.027

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.113
S = 1.05
3258 reflections
163 parameters
H-atom parameters constrained
_max = 0.24 e Å^-3
_min = -0.32 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the S1/N1/C1/C2/C7 thiazole ring, the C2-C7 benzene ring and the C8-C13 benzene ring, respectively.

D-HA	D-H	HA	DA	D-HA
C11-H11O1ⁱ	0.93	2.51	3.236 (2)	135
C9-H9Cg1ⁱⁱ	0.93	2.92	3.468 (2)	119
C10-H10Cg2ⁱⁱ	0.93	2.90	3.536 (2)	127
C3-H3Cg3ⁱⁱⁱ	0.93	2.99	3.673 (2)	132
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) -x, -y, -z+1; (iii) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia (1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6879 ).

Acknowledgements

SM thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help with the data collection.

References

Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Lakshmanan, D., Raj, R. M., Selvakumar, R., Bakthadoss, M. & Murugavel, S. (2011). Acta Cryst. E67, o2259.
Repic, O., Prasad, K. & Lee, G. T. (2001). Org. Process Res. Dev. 5, 519-527.
Schwartz, A., Madan, P. B., Mohacsi, E., O-Brien, J. P., Todaro, L. J. & Coffen, D. L. (1992). J. Org. Chem. 57, 851-856.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Zhang, Y., Su, Z.-H., Wang, Q.-Z. & Teng, L. (2008). Acta Cryst. E64, o2065.

organic compounds