3-Chloro-4-[2-(4-chloro­benzyl­idene)hydrazinyl­idene]-1-methyl-3,4-dihydro-1H-2λ6,1-benzothia­zine-2,2-dione

Ahmad, S.; Shafiq, M.; Tahir, M.N.; Harrison, W.T.A.; Khan, I.U.

doi:10.1107/S1600536813004443

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 (C-C) = 0.006 Å
R = 0.056
wR = 0.140
Data-to-parameter ratio = 15.2
Details

3-Chloro-4-[2-(4-chlorobenzylidene)hydrazinylidene]-1-methyl-3,4-dihydro-1H-2⁶,1-benzothiazine-2,2-dione

Saeed Ahmad,^a Muhammad Shafiq,^b ^* M. Nawaz Tahir,^c William T. A. Harrison ^d and Islam Ullah Khan ^e

^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-HO 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); Harmata et al. (2006). For the synthesis and biological activity of the title compound and related materials, see: Ahmad et al. (2010a); Shafiq et al. (2011a). For further synthetic details, see: Shafiq et al. (2011b). For related structures, see: Ahmad et al. (2010b); Shafiq et al. (2011c, 2013).

Experimental

Crystal data

C₁₆H₁₃Cl₂N₃O₂S
M_r = 382.25
Monoclinic, P 2₁ /c
a = 12.309 (2) Å
b = 17.189 (3) Å
c = 8.1837 (13) Å
= 101.632 (8)°
V = 1695.9 (5) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.868, T_max = 0.931
13580 measured reflections
3319 independent reflections
1736 reflections with I > 2(I)
R_int = 0.076

Refinement

R[F² > 2(F²)] = 0.056
wR(F²) = 0.140
S = 1.00
3319 reflections
218 parameters
H-atom parameters constrained
_max = 0.42 e Å^-3
_min = -0.33 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C4-H4O2ⁱ	0.93	2.48	3.356 (6)	158
C12-H12O2ⁱⁱ	0.93	2.59	3.419 (5)	149
C13-H13O1ⁱⁱⁱ	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); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); 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

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Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
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Misu, Y. & Togo, H. (2003). Org. Biomol. Chem. 1, 1342-1346.
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