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Volume 70 
Part 1 
Pages o52-o53  
January 2014  

Received 7 December 2013
Accepted 8 December 2013
Online 14 December 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.037
wR = 0.107
Data-to-parameter ratio = 14.9
Details
Open access

(2E)-2-(1,3-Benzo­thia­zol-2-yl)-3-(di­methyl­amino)­prop-2-ene­nitrile

aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England,bChemistry Department, Faculty of Sccience, Minia University, 61519 El-Minia, Egypt,cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,dSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, CF10 3AT, Wales,eDepartment of Chemistry, Faculty of Science, Sohag University, 82524 Sohag, Egypt, and fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
Correspondence e-mail: shaabankamel@yahoo.com

The mol­ecular conformation of title compound, C12H11N3S, is almost planar [maximum deviation = 0.063 (2) Å]; an intra­molecular C-H...N hydrogen bond is noted. In the crystal, mol­ecules inter­act with each other via [pi]-[pi] stacking inter­actions between thia­zole rings [centroid-centroid distance = 3.7475 (9) Å] and methyl-H...[pi](C6) inter­actions, forming columns along the a axis.

Related literature

For various biological activities (e.g. anti-tumour, anti-inflammatory, anti-viral, etc.) of benzo­thia­zole compounds, see: Selvam et al. (2011[Selvam, T. P., Radhika, P., Janagaraj, S. & Kumar, A. S. (2011). Res. Biotech. 2, 50-57.]); Sanja & Cvetkovic (2011[Sanja, O. & Cvetkovic, D. D. P.-K. (2011). Chem. Ind. Chem. Eng. Q. 17, 9-15.]); Alang et al. (2010[Alang, G., Kaur, G., Kaur, R., Singh, A. & Tiwari, R. (2010). J. Young Pharmacists, 2, 394-398.]); Pal et al. (2011[Pal, N., Kumar, M. & Seth, G. (2011). Eur. J. Chem. 8, 1174-1189.]); Sharma et al. (2010[Sharma, N. K., Priyanka, M. S. & Jha, K. K. (2010). J. Pharm. Res. 3, 969-970.]); El-Shaaer et al. (1997[El-Shaaer, H. M., Abdel-Aziz, S. A., Allimony, H. A., Ali, U. F. & Abdel-Rahman, R. M. (1997). Pharmazie, 52, 285-289.]); Gupta & Raat (2010[Gupta, A. & Raat, S. (2010). J. Curr. Pharm. Res. 3, 13-23.]); Hutchinson et al. (2002[Hutchinson, I., Jennings, S. A., Vishnuvajjala, B. R., Westwell, A. D. & Stevens, M. F. G. (2002). J. Med. Chem. 45, 744-747.]); Gong et al. (2004[Gong, B., Hong, F., Kohm, C., Bonham, L. & Klin, P. (2004). Bioorg. Med. Chem. Lett. 14, 1455-1459.]); Hutchinson et al. (2003[Hutchinson, I., Bradshaw, T. D., Matthew, C. S., Stevens, M. F. G. & Westwell, A. D. (2003). Bioorg. Med. Chem. Lett. 13, 471-474.]); Geronikaki & Theophilidis (1992[Geronikaki, A. & Theophilidis, G. (1992). Eur. J. Med. Chem. 27, 709-716.]); Vicini et al. (1990[Vicini, P., Amoretti, L., Chiavarini, M. & Impicciatore, M. (1990). Il Farmaco, 45, 933-943.]); Das et al. (2003[Das, J. J., Moquin, R. V., Liu, C., Doweyko, A. M., Defex, H. F., Fang, Q., Pang, S., Pitt, S., Shen, D. R., Schieven, G. L., Barrish, J. C. & Wityak, J. (2003). Bioorg. Med. Chem. Lett. 13, 2587-2590.]); Klose et al. (1983[Klose, N., Niedbolla, K., Schwartz, K. & Bottcher, I. (1983). Arch. Pharm. 316, 941-951.]); Satsangi et al. (1983[Satsangi, R. K., Zaidi, S. M. & Misra, V. C. (1983). Pharmazie, 38, 341-342.]).

[Scheme 1]

Experimental

Crystal data
  • C12H11N3S

  • Mr = 229.31

  • Monoclinic, P 21 /c

  • a = 7.3785 (2) Å

  • b = 20.1801 (4) Å

  • c = 8.2706 (2) Å

  • [beta] = 112.947 (4)°

  • V = 1134.03 (6) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 2.32 mm-1

  • T = 293 K

  • 0.26 × 0.20 × 0.09 mm

Data collection
  • Oxford Diffraction SuperNova (Dual, Cu at zero, Atlas) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2013[Oxford Diffraction (2013). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.584, Tmax = 0.818

  • 4062 measured reflections

  • 2195 independent reflections

  • 1971 reflections with I > 2[sigma](I)

  • Rint = 0.016

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.107

  • S = 1.05

  • 2195 reflections

  • 147 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 ring.

D-H...A D-H H...A D...A D-H...A
C9-H9...N1 0.93 2.44 2.851 (2) 106
C10-H10A...Cg1i 0.96 2.77 3.549 (2) 138
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2013[Oxford Diffraction (2013). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) 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: TK5279 ).


Acknowledgements

We thank Manchester Metropolitan University, Erciyes University and Cardiff University for supporting this study.

References

Alang, G., Kaur, G., Kaur, R., Singh, A. & Tiwari, R. (2010). J. Young Pharmacists, 2, 394-398.  [CrossRef] [ChemPort]
Das, J. J., Moquin, R. V., Liu, C., Doweyko, A. M., Defex, H. F., Fang, Q., Pang, S., Pitt, S., Shen, D. R., Schieven, G. L., Barrish, J. C. & Wityak, J. (2003). Bioorg. Med. Chem. Lett. 13, 2587-2590.  [CrossRef] [PubMed] [ChemPort]
El-Shaaer, H. M., Abdel-Aziz, S. A., Allimony, H. A., Ali, U. F. & Abdel-Rahman, R. M. (1997). Pharmazie, 52, 285-289.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Geronikaki, A. & Theophilidis, G. (1992). Eur. J. Med. Chem. 27, 709-716.  [CrossRef] [ChemPort] [Web of Science]
Gong, B., Hong, F., Kohm, C., Bonham, L. & Klin, P. (2004). Bioorg. Med. Chem. Lett. 14, 1455-1459.  [CrossRef] [PubMed] [ChemPort]
Gupta, A. & Raat, S. (2010). J. Curr. Pharm. Res. 3, 13-23.
Hutchinson, I., Bradshaw, T. D., Matthew, C. S., Stevens, M. F. G. & Westwell, A. D. (2003). Bioorg. Med. Chem. Lett. 13, 471-474.  [CrossRef] [PubMed] [ChemPort]
Hutchinson, I., Jennings, S. A., Vishnuvajjala, B. R., Westwell, A. D. & Stevens, M. F. G. (2002). J. Med. Chem. 45, 744-747.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Klose, N., Niedbolla, K., Schwartz, K. & Bottcher, I. (1983). Arch. Pharm. 316, 941-951.  [CrossRef] [ChemPort]
Oxford Diffraction (2013). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Pal, N., Kumar, M. & Seth, G. (2011). Eur. J. Chem. 8, 1174-1189.  [ChemPort]
Sanja, O. & Cvetkovic, D. D. P.-K. (2011). Chem. Ind. Chem. Eng. Q. 17, 9-15.
Satsangi, R. K., Zaidi, S. M. & Misra, V. C. (1983). Pharmazie, 38, 341-342.  [ChemPort] [PubMed]
Selvam, T. P., Radhika, P., Janagaraj, S. & Kumar, A. S. (2011). Res. Biotech. 2, 50-57.
Sharma, N. K., Priyanka, M. S. & Jha, K. K. (2010). J. Pharm. Res. 3, 969-970.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Vicini, P., Amoretti, L., Chiavarini, M. & Impicciatore, M. (1990). Il Farmaco, 45, 933-943.  [ChemPort] [PubMed]


Acta Cryst (2014). E70, o52-o53   [ doi:10.1107/S1600536813033266 ]

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