7H-[1,2]Benzothia­zolo[3,2-b]quinazoline 5,5-dioxide

Narayanan, P.; Karthikeyan, S.; Srinivasan, P.C.; Sethusankar, K.

doi:10.1107/S1600536812040871

Volume 68
Part 11
Page o3082
November 2012

Received 10 September 2012
Accepted 28 September 2012
Online 6 October 2012

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.002 Å
R = 0.034
wR = 0.122
Data-to-parameter ratio = 13.5
Details

7H-[1,2]Benzothiazolo[3,2-b]quinazoline 5,5-dioxide

Ponmudisettu Narayanan,^a Subramani Karthikeyan,^a Panayancheri Coleppa Srinivasan ^a and Krishnan Sethusankar ^a ^*

^aDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India
Correspondence e-mail: ksethusankar@yahoo.co.in

In the title compound, C₁₄H₁₀N₂O₂S, the benzothiazole and quinazoline ring systems are essentially planar with maximum deviations of 0.0127 (16) and 0.1588 (15) Å, respectively, and make a dihedral angleof 3.02 (5)°, which shows that the entire molecule is almost planar. The O atoms deviate from the benzothiazole ring system by 1.2231 (14) and -1.1989 (15) Å. The crystal packing features non-classical C-HO hydrogen bonds and is further consolidated by [pi] - [pi] interactions [centroid-centroid distances = 3.7568 (8) and 3.8848 (9) Å].

Related literature

For the uses and biological importance of benzothiazole and quinazoline derivatives, see: Schwartz et al. (1992); Wolfe et al. (1990); Tereshima et al. (1995). For related structures, see: Khan et al. (2012); Grundt et al. (2010).

Experimental

Crystal data

C₁₄H₁₀N₂O₂S
M_r = 270.31
Orthorhombic, P b c a
a = 7.9389 (2) Å
b = 13.1460 (4) Å
c = 22.7952 (7) Å
V = 2379.02 (12) Å³
Z = 8
Mo K radiation
= 0.27 mm^-1
T = 295 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) T_min = 0.922, T_max = 0.947
21710 measured reflections
2328 independent reflections
1981 reflections with I > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.034
wR(F²) = 0.122
S = 1.06
2328 reflections
172 parameters
H-atom parameters constrained
_max = 0.25 e Å^-3
_min = -0.33 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C2-H2O1ⁱ	0.93	2.43	3.275 (2)	150
Symmetry code: (i) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; 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: RK2382 ).

Acknowledgements

The authors thank Dr Babu Varghese, Senior Scientific Officer, SAIF, IIT, Chennai, India, for the data collection. They also thank the University Grant Commission (UGC) for funding the minor project [Ref. No. F. MRP-3640/11 (SERO-UGC)] under which this work has been carried out.

References

Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Grundt, P., Douglas, K. A., Krivogorsky, B. & Nemykin, V. N. (2010). Acta Cryst. E66, o1474-o1475.
Khan, M. H., Khan, I. U., Mughal, S. Y. & Akkurt, M. (2012). Acta Cryst. E68, o507.
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. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Tereshima, K., Shimamura, H., Kawase, A., Tanaka, Y., Tanimura, T., Ishizuka, Y. & Sato, M. (1995). Chem. Pharm. Bull. 45, 2021-2023.
Wolfe, J. F., Rathman, T. L., Sleevi, M. C., Cambell, J. S. A. & Greenwood, T. D. (1990). J. Med. Chem. 33, 161-166.

organic compounds