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Volume 70 
Part 1 
Page o41  
January 2014  

Received 27 November 2013
Accepted 9 December 2013
Online 14 December 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.006 Å
R = 0.064
wR = 0.192
Data-to-parameter ratio = 12.7
Details
Open access

2-(1-Benzo­thio­phen-2-yl)-4H-1,3,4-oxa­diazin-5(6H)-one

aChemical Engineering Department, Nanjing College of Chemical Technology, Nanjing 210048, People's Republic of China, and bCollege of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
Correspondence e-mail: njutshs@126.com

In the title compound, C11H8N2O2S, the oxadiazinone ring is nearly planar [maximum deviation = 0.016 (4) Å], and is approximately coplanar with the benzo­thio­phene ring system [dihedral angle = 3.1 (5)°]. In the crystal, mol­ecules are linked by N-H...O hydrogen bonds, forming chains running along the b-axis direction.

Related literature

For applications of oxadiazin derivatives, see: De Sarro et al. (2005[De Sarro, G., Gitto, R., Russo, E., Ibbadu, G. F., Barreca, M. L., De Luca, L. & Chimirri, A. (2005). Curr. Top. Med. Chem. 5, 31-42.]); Shigeki et al. (2012[Shigeki, H., Koshi, U., Satoshi, N., Koki, K., Koichi, I., Yoshikiko, N., Osamu, T., Takahisa, H. & Masahiro, Y. (2012). J. Med. Chem. 55, 10584-10600.]).

[Scheme 1]

Experimental

Crystal data
  • C11H8N2O2S

  • Mr = 232.25

  • Monoclinic, P 21 /n

  • a = 7.4950 (15) Å

  • b = 6.0350 (12) Å

  • c = 22.412 (5) Å

  • [beta] = 93.08 (3)°

  • V = 1012.3 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.30 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.915, Tmax = 0.970

  • 1999 measured reflections

  • 1848 independent reflections

  • 1167 reflections with I > 2[sigma](I)

  • Rint = 0.064

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.064

  • wR(F2) = 0.192

  • S = 1.00

  • 1848 reflections

  • 145 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.39 e Å-3

  • [Delta][rho]min = -0.39 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O2i 0.86 2.03 2.848 (5) 158
Symmetry code: (i) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{5\over 2}}].

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5757 ).


Acknowledgements

The work was supported by Nanjing College of Chemical Technology, China (NHKY-2013-02).

References

De Sarro, G., Gitto, R., Russo, E., Ibbadu, G. F., Barreca, M. L., De Luca, L. & Chimirri, A. (2005). Curr. Top. Med. Chem. 5, 31-42.  [Web of Science] [PubMed] [ChemPort]
Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Shigeki, H., Koshi, U., Satoshi, N., Koki, K., Koichi, I., Yoshikiko, N., Osamu, T., Takahisa, H. & Masahiro, Y. (2012). J. Med. Chem. 55, 10584-10600.  [Web of Science] [PubMed]


Acta Cryst (2014). E70, o41  [ doi:10.1107/S1600536813033291 ]

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