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Volume 69 
Part 2 
Page o165  
February 2013  

Received 19 December 2012
Accepted 20 December 2012
Online 4 January 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.007 Å
R = 0.067
wR = 0.201
Data-to-parameter ratio = 13.7
Details
Open access

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

aDepartment of Chemistry, Government College University, Faisalabad 38000, Pakistan,bDepartment of Physics, University of Sargodha, Sargodha, Pakistan,cDepartment of Chemistry, University of Aberdeen, Mston Walk, Aberdeen AB24 3UE, Scotland, and dMaterials Chemistry Laboratory, Department of Chemistry, Government College University, Lahore, Pakistan
Correspondence e-mail: hafizshafique@hotmail.com

In the title compound, C18H16ClN3O2S, the dihedral angle between the aromatic rings is 4.81 (2)° and the alkyl chain takes on an extended conformation [N-C-C-C = 179.2 (4)°]. The conformation of the thiazine ring is an envelope, with the S atom displaced by -0.805 (3) Å from the mean plane of the other five atoms (r.m.s. deviation = 0.046 Å). The Cl atom is an axial conformation and is displaced by 1.761 (4) Å from the thiazine ring plane. In the crystal, inversion dimers linked by pairs of C-H...O interactions generate R22(20) loops and further C-H...O hydrogen bonds link the dimers into (001) sheets. Weak aromatic [pi]-[pi] stacking interactions [centroid-centroid separations = 3.870 (3) and 3.883 (3) Å] are also observed.

Related literature

For the synthesis and biological activity of the title compound and related materials, see: Shafiq et al. (2011a[Shafiq, M., Zia-Ur-Rehman, M., Khan, I. U., Arshad, M. N. & Khan, S. A. (2011a). JJ. 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.]).

[Scheme 1]

Experimental

Crystal data
  • C18H16ClN3O2S

  • Mr = 373.85

  • Monoclinic, P 21 /c

  • a = 7.2262 (5) Å

  • b = 13.5823 (9) Å

  • c = 17.9818 (12) Å

  • [beta] = 97.023 (4)°

  • V = 1751.6 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.35 mm-1

  • T = 296 K

  • 0.32 × 0.20 × 0.18 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 = 0.895, Tmax = 0.939

  • 8051 measured reflections

  • 3107 independent reflections

  • 1808 reflections with I > 2[sigma](I)

  • Rint = 0.043

Refinement
  • R[F2 > 2[sigma](F2)] = 0.067

  • wR(F2) = 0.201

  • S = 1.03

  • 3107 reflections

  • 227 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.97 e Å-3

  • [Delta][rho]min = -0.36 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C12-H12...O2i 0.93 2.51 3.345 (6) 150
C15-H15...O2ii 0.93 2.57 3.464 (6) 161
Symmetry codes: (i) -x, -y+1, -z+1; (ii) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

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 (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: BQ2381 ).


Acknowledgements

MS acknowledges the HEC Pakistan for granting a PhD fellowship.

References

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]
Shafiq, M., Khan, I. U., Arshad, M. N. & Siddiqui, W. A. (2011b). Asian J. Chem. 23, 2101-2106.  [ChemPort]
Shafiq, M., Zia-Ur-Rehman, M., Khan, I. U., Arshad, M. N. & Khan, S. A. (2011a). JJ. Chil. Chem. Soc. 56, 527-531.  [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o165  [ doi:10.1107/S1600536812051513 ]

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