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Volume 69 
Part 2 
Page o164  
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) = 0.004 Å
R = 0.037
wR = 0.082
Data-to-parameter ratio = 14.7
Details
Open access

6-Bromo-1-methyl-4-[2-(1-phenylethylidene)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, Meston 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, C17H16BrN3O2S, the dihedral angle between the aromatic rings is 1.24 (15)° and the C=N-N=C torsion angle is 167.7 (3)°. 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 = 0.027 Å). In the crystal, C-H...O interactions link the molecules into C(10) [010] chains. A weak C-H...[pi] interaction is also observed.

Related literature

For the synthesis and biological activity of the title compound and related materials, see: Shafiq, Zia-Ur-Rehman et al. (2011[Shafiq, M., Zia-Ur-Rehman, M., Khan, I. U., Arshad, M. N. & Khan, S. A. (2011). J. Chil. Chem. Soc. 56, 527-531.]). For further synthetic details, see: Shafiq, Khan et al. (2011[Shafiq, M., Khan, I. U., Arshad, M. N. & Siddiqui, W. A. (2011). Asian J. Chem. 23, 2101-2106.]).

[Scheme 1]

Experimental

Crystal data
  • C17H16BrN3O2S

  • Mr = 406.30

  • Monoclinic, P 21 /c

  • a = 16.4369 (13) Å

  • b = 6.5400 (5) Å

  • c = 16.5025 (17) Å

  • [beta] = 104.312 (4)°

  • V = 1718.9 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 2.53 mm-1

  • T = 296 K

  • 0.34 × 0.22 × 0.20 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 = 0.518, Tmax = 0.603

  • 7358 measured reflections

  • 3213 independent reflections

  • 2256 reflections with I > 2[sigma](I)

  • Rint = 0.026

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

  • wR(F2) = 0.082

  • S = 1.02

  • 3213 reflections

  • 219 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.56 e Å-3

  • [Delta][rho]min = -0.51 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1-C6 ring.

D-H...A D-H H...A D...A D-H...A
C2-H2...O2i 0.93 2.49 3.280 (4) 143
C13-H13...Cg2ii 0.93 2.65 3.445 (3) 143
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [x+1, -y+{\script{3\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, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG5314 ).


Acknowledgements

MS acknowledges the support of HEC Pakistan for the PhD fellowship.

References

Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Shafiq, M., Khan, I. U., Arshad, M. N. & Siddiqui, W. A. (2011). Asian J. Chem. 23, 2101-2106.  [ChemPort]
Shafiq, M., Zia-Ur-Rehman, M., Khan, I. U., Arshad, M. N. & Khan, S. A. (2011). 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, o164  [ doi:10.1107/S1600536812051380 ]

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