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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 [sigma](C-C) = 0.002 Å
R = 0.034
wR = 0.122
Data-to-parameter ratio = 13.5
Details
Open access

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

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-H...O 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[Schwartz, A., Madan, P. B., Mohacsi, E., O-Brien, J. P., Todaro, L. J. & Coffen, D. L. (1992). J. Org. Chem. 57, 851-856.]); Wolfe et al. (1990[Wolfe, J. F., Rathman, T. L., Sleevi, M. C., Cambell, J. S. A. & Greenwood, T. D. (1990). J. Med. Chem. 33, 161-166.]); Tereshima et al. (1995[Tereshima, K., Shimamura, H., Kawase, A., Tanaka, Y., Tanimura, T., Ishizuka, Y. & Sato, M. (1995). Chem. Pharm. Bull. 45, 2021-2023.]). For related structures, see: Khan et al. (2012[Khan, M. H., Khan, I. U., Mughal, S. Y. & Akkurt, M. (2012). Acta Cryst. E68, o507.]); Grundt et al. (2010[Grundt, P., Douglas, K. A., Krivogorsky, B. & Nemykin, V. N. (2010). Acta Cryst. E66, o1474-o1475.]).

[Scheme 1]

Experimental

Crystal data
  • C14H10N2O2S

  • Mr = 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[alpha] radiation

  • [mu] = 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[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.922, Tmax = 0.947

  • 21710 measured reflections

  • 2328 independent reflections

  • 1981 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.122

  • S = 1.06

  • 2328 reflections

  • 172 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.33 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2...O1i 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[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


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.  [CrossRef] [details]
Grundt, P., Douglas, K. A., Krivogorsky, B. & Nemykin, V. N. (2010). Acta Cryst. E66, o1474-o1475.  [CSD] [CrossRef] [details]
Khan, M. H., Khan, I. U., Mughal, S. Y. & Akkurt, M. (2012). Acta Cryst. E68, o507.  [CSD] [CrossRef] [details]
Schwartz, A., Madan, P. B., Mohacsi, E., O-Brien, J. P., Todaro, L. J. & Coffen, D. L. (1992). J. Org. Chem. 57, 851-856.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
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.  [CrossRef] [ChemPort] [PubMed] [ISI]


Acta Cryst (2012). E68, o3082  [ doi:10.1107/S1600536812040871 ]

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