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Volume 69 
Part 3 
Pages o422-o423  
March 2013  

Received 27 December 2012
Accepted 14 February 2013
Online 23 February 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.006 Å
R = 0.056
wR = 0.140
Data-to-parameter ratio = 15.2
Details
Open access

3-Chloro-4-[2-(4-chlorobenzylidene)hydrazinylidene]-1-methyl-3,4-dihydro-1H-2[lambda]6,1-benzothiazine-2,2-dione

aDepartment of Chemistry, Gomal University, Dera Ismail Khan, NWFP, Pakistan,bDepartment of Chemistry, Government College University, Faisalabad 38000, Pakistan,cDepartment of Physics, University of Sargodha, Sargodha, Pakistan,dDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland, and eMaterials Chemistry Laboratory, Department of Chemistry, Government College University, Lahore, Pakistan
Correspondence e-mail: hafizshafique@hotmail.com

In the title compound, C16H13Cl2N3O2S, the dihedral angle between the aromatic rings is 6.62 (2)° and the C=N-N=C torsion angle is 176.2 (4)°. The thiazine ring shows an envelope conformation, with the S atom displaced by 0.633 (6) Å from the mean plane of the other five atoms (r.m.s. deviation = 0.037 Å). The Cl atom is an an axial conformation and is displaced by 2.015 (6) Å from the thiazine ring plane. In the crystal, molecules are linked by C-H...O interactions, generating a three-dimensional network. Very weak aromatic [pi]-[pi] stacking interactions [centroid-centroid separations = 3.928 (2) Å] are also observed.

Related literature

For background to benzothiazines, see: Misu & Togo (2003[Misu, Y. & Togo, H. (2003). Org. Biomol. Chem. 1, 1342-1346.]); Harmata et al. (2006[Harmata, M., Calkins, N. L., Baughman, R. G. & Barnes, C. L. (2006). J. Org. Chem. 71, 3650-3652.]). For the synthesis and biological activity of the title compound and related materials, see: Ahmad et al. (2010a[Ahmad, M., Siddiqui, H. L., Zia-ur-Rehman, M. & Parvez, M. (2010a). Eur. J. Med. Chem. 45, 698-704.]); Shafiq et al. (2011a[Shafiq, M., Zia-Ur-Rehman, M., Khan, I. U., Arshad, M. N. & Khan, S. A. (2011a). J. Chil. Chem. Soc. 56, 527-531.]). For further synthetic details, see: Shafiq et al. (2011b[Shafiq, M., Khan, I. U., Arshad, M. N. & Siddiqui, W. A. (2011b). Asian J. Chem. 23, 2101-2106.]). For related structures, see: Ahmad et al. (2010b[Ahmad, M., Siddiqui, H. L., Ahmad, S., Parvez, M. & Tizzard, G. J. (2010b). J. Chem. Crystallogr. 40, 1188-1194.]); Shafiq et al. (2011c[Shafiq, M., Khan, I. U., Zia-ur-Rehman, M., Arshad, M. N. & Asiri, A. M. (2011c). Acta Cryst. E67, o2038.], 2013[Shafiq, M., Tahir, M. N., Harrison, W. T. A., Khan, I. U. & Shafique, S. (2013). Acta Cryst. E69, o165.]).

[Scheme 1]

Experimental

Crystal data
  • C16H13Cl2N3O2S

  • Mr = 382.25

  • Monoclinic, P 21 /c

  • a = 12.309 (2) Å

  • b = 17.189 (3) Å

  • c = 8.1837 (13) Å

  • [beta] = 101.632 (8)°

  • V = 1695.9 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.52 mm-1

  • T = 296 K

  • 0.28 × 0.16 × 0.14 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.868, Tmax = 0.931

  • 13580 measured reflections

  • 3319 independent reflections

  • 1736 reflections with I > 2[sigma](I)

  • Rint = 0.076

Refinement
  • R[F2 > 2[sigma](F2)] = 0.056

  • wR(F2) = 0.140

  • S = 1.00

  • 3319 reflections

  • 218 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.42 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
C4-H4...O2i 0.93 2.48 3.356 (6) 158
C12-H12...O2ii 0.93 2.59 3.419 (5) 149
C13-H13...O1iii 0.93 2.50 3.293 (5) 143
Symmetry codes: (i) x, y, z+1; (ii) -x+1, -y, -z; (iii) x+1, y, z.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). 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 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2417 ).


Acknowledgements

MS acknowledges the HEC Pakistan for providing a PhD fellowship and the UOS, Sargodha, for X-ray diffraction facility.

References

Ahmad, M., Siddiqui, H. L., Ahmad, S., Parvez, M. & Tizzard, G. J. (2010b). J. Chem. Crystallogr. 40, 1188-1194.  [ISI] [CSD] [CrossRef] [ChemPort]
Ahmad, M., Siddiqui, H. L., Zia-ur-Rehman, M. & Parvez, M. (2010a). Eur. J. Med. Chem. 45, 698-704.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Harmata, M., Calkins, N. L., Baughman, R. G. & Barnes, C. L. (2006). J. Org. Chem. 71, 3650-3652.  [CrossRef] [PubMed] [ChemPort]
Misu, Y. & Togo, H. (2003). Org. Biomol. Chem. 1, 1342-1346.  [CrossRef] [PubMed] [ChemPort]
Shafiq, M., Khan, I. U., Arshad, M. N. & Siddiqui, W. A. (2011b). Asian J. Chem. 23, 2101-2106.  [ChemPort]
Shafiq, M., Khan, I. U., Zia-ur-Rehman, M., Arshad, M. N. & Asiri, A. M. (2011c). Acta Cryst. E67, o2038.  [CSD] [CrossRef] [details]
Shafiq, M., Tahir, M. N., Harrison, W. T. A., Khan, I. U. & Shafique, S. (2013). Acta Cryst. E69, o165.  [CrossRef] [details]
Shafiq, M., Zia-Ur-Rehman, M., Khan, I. U., Arshad, M. N. & Khan, S. A. (2011a). J. Chil. Chem. Soc. 56, 527-531.  [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o422-o423   [ doi:10.1107/S1600536813004443 ]

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