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Volume 68 
Part 11 
Page o3138  
November 2012  

Received 9 September 2012
Accepted 8 October 2012
Online 20 October 2012

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Key indicators
Single-crystal X-ray study
T = 113 K
Mean [sigma](C-C) = 0.003 Å
R = 0.048
wR = 0.100
Data-to-parameter ratio = 17.5
Details
Open access

2-(1,3-Benzothiazol-2-ylsulfanyl)-N-(2-methylphenyl)acetamide

Yue Sun,a Xiao-Jun Wangb and Peng-Wu Zhenga*

aSchool of Pharmacy, Jiangxi Science and Technology Normal University, Nanchang 330013, People's Republic of China, and bPolytechnic Institute of Jiangxi Science and Technology Normal University, Nanchang 330013, People's Republic of China
Correspondence e-mail: zhengpw@126.com

In the title molecule, C16H14N2OS2, the benzene ring and the benzo[d]thiazole mean plane form a dihedral angle of 75.5 (1)°. The acetamide group is twisted by 47.7 (1)° from the attached benzene ring. In the crystal, molecules related by translation along the a axis are linked into chains through N-H...O hydrogen bonds.

Related literature

For the crystal structures of similar compounds, see: Gao et al. (2007[Gao, Y., Liang, D., Gao, L.-X., Fang, G.-J. & Wang, W. (2007). Acta Cryst. E63, o4854.]); Zhao et al. (2009[Zhao, B., Wang, H., Li, Q., Gao, Y. & Liang, D. (2009). Acta Cryst. E65, o958.]). For the medical activity of heterocyclic derivatives containing the acetamide group, see: Fallah-Tafti et al. (2011[Fallah-Tafti, A., Foroumadi, A., Tiwari, R., Shirazi, A. N., Hangauer, D. G., Bu, Y., Akbarzadeh, T., Parang, K. & Shafiee, A. (2011). Eur. J. Med. Chem. 46, 4853-4858.]); Shams et al. (2011[Shams, H. Z., Mohareb, R. M., Helal, M. H. & Mahmoud, A. (2011). Molecules, 16, 52-73.])

[Scheme 1]

Experimental

Crystal data

  • C16H14N2OS2

  • Mr = 314.41

  • Monoclinic, P 21 /n

  • a = 4.7957 (8) Å

  • b = 27.496 (4) Å

  • c = 10.9906 (13) Å

  • [beta] = 97.048 (4)°

  • V = 1438.3 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.37 mm-1

  • T = 113 K

  • 0.22 × 0.06 × 0.06 mm
Data collection

  • Rigaku Saturn CCD area-detector diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear. Molecular Structure Corporation, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.923, Tmax = 0.978

  • 14718 measured reflections

  • 3421 independent reflections

  • 2923 reflections with I > 2[sigma](I)

  • Rint = 0.055
Refinement

  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.100

  • S = 1.06

  • 3421 reflections

  • 195 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.33 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1i 0.81 (2) 2.10 (2) 2.906 (2) 168 (2)
Symmetry code: (i) x+1, y, z.

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear. Molecular Structure Corporation, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5340 ).

Acknowledgements

Support from the Science and Technology Project of Jiangxi Provincial Office of Eduction (grant No. GJJ11008) and the Science and Technology Project of Jiangxi Provincial Department of Science and Technology (grant No. 20111BBE50009) is gratefully acknowledged.

References

Fallah-Tafti, A., Foroumadi, A., Tiwari, R., Shirazi, A. N., Hangauer, D. G., Bu, Y., Akbarzadeh, T., Parang, K. & Shafiee, A. (2011). Eur. J. Med. Chem. 46, 4853-4858.  [ISI] [ChemPort] [PubMed]
Gao, Y., Liang, D., Gao, L.-X., Fang, G.-J. & Wang, W. (2007). Acta Cryst. E63, o4854.  [CSD] [CrossRef] [details]
Rigaku/MSC (2005). CrystalClear. Molecular Structure Corporation, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
Shams, H. Z., Mohareb, R. M., Helal, M. H. & Mahmoud, A. (2011). Molecules, 16, 52-73.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Zhao, B., Wang, H., Li, Q., Gao, Y. & Liang, D. (2009). Acta Cryst. E65, o958.  [CSD] [CrossRef] [details]

Acta Cryst (2012). E68, o3138  [ doi:10.1107/S1600536812042109 ]

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