2-(2H-1,3-Benzodioxol-5-yl)-1,3-benzo­thia­zole

Lakshmanan, D.; Murugavel, S.; Selvakumar, R.; Bakthadoss, M.

doi:10.1107/S1600536812008914

Volume 68
Part 4
Page o961
April 2012

Received 13 February 2012
Accepted 28 February 2012
Online 3 March 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R = 0.039
wR = 0.105
Data-to-parameter ratio = 19.2
Details

2-(2H-1,3-Benzodioxol-5-yl)-1,3-benzothiazole

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

^aDepartment of Physics, C. Abdul Hakeem College of Engineering & Technology, Melvisharam, Vellore 632 509, 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, C₁₄H₉O₂S, the benzothiazole unit is oriented at a dihedral angle of 7.1 (1)° with respect to the benzodioxole unit. The dioxole ring adopts flattened envelope conformation with the methylene C atom at the flap. The crystal packing is stabilized by [pi] - [pi] interactions [centroid-centroid distances = 3.705 (1) and 3.752 (1) Å], C-H [pi] interactions and a short SS contact of 3.485 (1) Å.

Related literature

For background to the applications of benzothiazoles in the chemical industry, see: Bradshaw et al. (2002); Delmas et al. (2002); Hutchinson et al. (2002). For the pharmacological activity of benzothiazole derivatives, see: Repic et al. (2001); Schwartz et al. (1992). For ring puckering analysis, see: Cremer & Pople (1975). For related structures, see: Baryala et al. (2010); Zhang et al. (2008).

Experimental

Crystal data

C₁₄H₉NO₂S
M_r = 255.28
Orthorhombic, P b c a
a = 6.3356 (2) Å
b = 16.3222 (5) Å
c = 22.0471 (7) Å
V = 2279.91 (12) Å³
Z = 8
Mo K radiation
= 0.28 mm^-1
T = 293 K
0.25 × 0.23 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.934, T_max = 0.952
15338 measured reflections
3135 independent reflections
2243 reflections with I > 2(I)
R_int = 0.027

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.105
S = 1.02
3135 reflections
163 parameters
H-atom parameters constrained
_max = 0.29 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the dioxole ring and Cg2 is the centroid of the C2-C7 benzene ring.

D-HA	D-H	HA	DA	D-HA
C5-H5Cg1ⁱ	0.93	2.79	3.624 (2)	150
C14-H14BCg2ⁱⁱ	0.97	2.84	3.580 (2)	134
Symmetry codes: (i) $[x, -y-{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x-1, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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: GK2459 ).

Acknowledgements

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

References

Baryala, Y., Zerzouf, A., Salem, M., Essassi, E. M. & El Ammari, L. (2010). Acta Cryst. E66, o857.
Bradshaw, T. D., Chua, M. S., Browne, H. L., Trapani, V., Sausville, E. A. & Stevens, M. F. G. (2002). Br. J. Cancer, 86, 1348-1354.
Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Delmas, F., Di Giorgio, C., Robin, M., Azas, N., Gasquet, M., Detang, C., Costa, M., Timon-David, P. & Galy, J.-P. (2002). Antimicrob. Agents Chemother. 46, 2588-2594.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Hutchinson, I., Jennings, S. A., Vishnuvajjala, B. R., Westwell, A. D. & Stevens, M. F. G. (2002). J. Med. Chem. 45, 744-747.
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