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Volume 70 
Part 5 
Page o614  
May 2014  

Received 22 April 2014
Accepted 23 April 2014
Online 26 April 2014

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.046
wR = 0.124
Data-to-parameter ratio = 17.1
Details
Open access

(2Z)-2-Benzyl­idene-4-(prop-2-yn-1-yl)-2H-1,4-benzo­thia­zin-3(4H)-one

aLaboratoire de Chimie Organique Hétérocyclique URAC 21, Pôle de Compétence Pharmacochimie, Av. Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V-Agdal, Rabat, Morocco,bLaboratoire de Chimie Organique et Etudes Physicochimiques, ENS Takaddoum, Rabat, Morocco, and cLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
Correspondence e-mail: nk_sebbar@yahoo.fr

The mol­ecule of the title compound, C18H13NOS, is build up from two fused six-membered rings, with the heterocyclic component linked to a benzyl­idene group and to a prop-2-yn-1-yl chain. The six-membered heterocycle adopts a distorted screw-boat conformation. The prop-2-yn-1-yl chain is almost perpendicular to the mean plane through benzo­thia­zine as indicated by the C-N-C-C torsion angle of 86.5 (2)°. The dihedral angle between the benzene rings is 47.53 (12)°. There are no specific inter­molecular inter­actions in the crystal packing.

Related literature

For the pharmacological activity of benzo­thia­zine derivatives, see: Aotsuka et al. (1994[Aotsuka, T., Hosono, H., Kurihara, T., Nakamura, Y., Matsui, T. & Kobayashi, F. (1994). Chem. Pharm. Bull. 42, 1264-1271.]); Fujimura et al. (1996[Fujimura, K., Ota, A. & Kawashima, Y. (1996). Chem. Pharm. Bull. 44, 542-546.]); Rathore & Kumar (2006[Rathore, B. S. & Kumar, M. (2006). Bioorg. Med. Chem. 14, 5678-5682.]); Fringuelli et al. (1998[Fringuelli, R., Schiaffella, F., Bistoni, F., Pitzurra, L. & Vecchiarelli, A. (1998). Bioorg. Med. Chem. 6, 103-108.]). For related structures, see: Sebbar et al. (2014a[Sebbar, N. K., Zerzouf, A., Essassi, E. M., Saadi, M. & El Ammari, L. (2014a). Acta Cryst. E70, o160-o161.],b[Sebbar, N. K., Zerzouf, A., Essassi, E. M., Saadi, M. & El Ammari, L. (2014b). Acta Cryst. E70, o116.]); Zerzouf et al. (2001[Zerzouf, A., Salem, M., Essassi, E. M. & Pierrot, M. (2001). Acta Cryst. E57, o498-o499.]). For conformation analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C18H13NOS

  • Mr = 291.35

  • Orthorhombic, P b c a

  • a = 9.0254 (13) Å

  • b = 7.7388 (12) Å

  • c = 42.488 (7) Å

  • V = 2967.6 (8) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.22 mm-1

  • T = 296 K

  • 0.42 × 0.36 × 0.31 mm

Data collection
  • Bruker X8 APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.579, Tmax = 0.746

  • 14350 measured reflections

  • 3248 independent reflections

  • 2227 reflections with I > 2[sigma](I)

  • Rint = 0.038

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.124

  • S = 1.02

  • 3248 reflections

  • 190 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2009[Bruker (2009). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supporting information for this paper is available from the IUCr electronic archives (Reference: TK5310 ).


Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.

References

Aotsuka, T., Hosono, H., Kurihara, T., Nakamura, Y., Matsui, T. & Kobayashi, F. (1994). Chem. Pharm. Bull. 42, 1264-1271.  [CrossRef] [ChemPort] [PubMed]
Bruker (2009). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Fringuelli, R., Schiaffella, F., Bistoni, F., Pitzurra, L. & Vecchiarelli, A. (1998). Bioorg. Med. Chem. 6, 103-108.  [CrossRef] [ChemPort] [PubMed]
Fujimura, K., Ota, A. & Kawashima, Y. (1996). Chem. Pharm. Bull. 44, 542-546.  [CrossRef] [ChemPort] [PubMed]
Rathore, B. S. & Kumar, M. (2006). Bioorg. Med. Chem. 14, 5678-5682.  [CrossRef] [PubMed] [ChemPort]
Sebbar, N. K., Zerzouf, A., Essassi, E. M., Saadi, M. & El Ammari, L. (2014a). Acta Cryst. E70, o160-o161.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Sebbar, N. K., Zerzouf, A., Essassi, E. M., Saadi, M. & El Ammari, L. (2014b). Acta Cryst. E70, o116.  [CSD] [CrossRef] [IUCr Journals]
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]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Zerzouf, A., Salem, M., Essassi, E. M. & Pierrot, M. (2001). Acta Cryst. E57, o498-o499.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2014). E70, o614  [ doi:10.1107/S1600536814009179 ]

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