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Volume 69 
Part 2 
Page o200  
February 2013  

Received 27 December 2012
Accepted 3 January 2013
Online 9 January 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.048
wR = 0.139
Data-to-parameter ratio = 15.7
Details
Open access

1-Ethyl-4-{2-[1-(4-methylphenyl)ethylidene]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, and cDepartment of Chemistry, University of Aberdeen, Mston Walk, Aberdeen AB24 3UE, Scotland
Correspondence e-mail: hafizshafique@hotmail.com

In the title compound, C19H21N3O2S, the dihedral angle between the aromatic rings is 6.7 (2)° and the C=N-N=C torsion angle is 178.0 (2)°. The conformation of the thiazine ring is an envelope, with the S atom displaced by 0.802 (2) Å from the mean plane of the other five atoms (r.m.s. deviation = 0.022 Å). In the crystal, molecules are linked by C-H...O interactions, generating C(5) chains propagating in [010]. 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 et al. (2011a[Shafiq, M., Zia-Ur-Rehman, M., Khan, I. U., Arshad, M. N. & Khan, S. A. (2011a). J. Chilean 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 a related structure, see: Shafiq et al. (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
  • C19H21N3O2S

  • Mr = 355.45

  • Monoclinic, P 21 /n

  • a = 15.9018 (10) Å

  • b = 7.3716 (4) Å

  • c = 16.8376 (10) Å

  • [beta] = 111.644 (3)°

  • V = 1834.57 (19) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.19 mm-1

  • T = 296 K

  • 0.34 × 0.26 × 0.24 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 = 0.937, Tmax = 0.955

  • 14168 measured reflections

  • 3597 independent reflections

  • 2598 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.139

  • S = 1.02

  • 3597 reflections

  • 229 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.45 e Å-3

  • [Delta][rho]min = -0.40 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C13-C18 ring.

D-H...A D-H H...A D...A D-H...A
C7-H7A...O2i 0.97 2.50 3.402 (4) 155
C9-H9A...Cg3ii 0.97 2.67 3.613 (2) 165
Symmetry codes: (i) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) x, y-1, 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 (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: LD2091 ).


Acknowledgements

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

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., 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. Chilean Chem. Soc. 56, 527-531.  [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o200  [ doi:10.1107/S1600536813000202 ]

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