1-Ethyl-4-{2-[1-(4-methyl­phen­yl)ethyl­idene]hydrazinyl­idene}-3,4-dihydro-1H-2λ6,1-benzothia­zine-2,2-dione

Shafiq, M.; Tahir, M.N.; Harrison, W.T.A.; Bokhari, T.H.; Safder, M.

doi:10.1107/S1600536813000202

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 (C-C) = 0.004 Å
R = 0.048
wR = 0.139
Data-to-parameter ratio = 15.7
Details

1-Ethyl-4-{2-[1-(4-methylphenyl)ethylidene]hydrazinylidene}-3,4-dihydro-1H-2⁶,1-benzothiazine-2,2-dione

Muhammad Shafiq,^a ^* M. Nawaz Tahir,^b William T. A. Harrison,^c Tanveer Hussain Bokhari ^a and Muhammad Safder ^a

^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-HO 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). For further synthetic details, see: Shafiq et al. (2011b). For a related structure, see: Shafiq et al. (2013).

Experimental

Crystal data

C₁₉H₂₁N₃O₂S
M_r = 355.45
Monoclinic, P 2₁ /n
a = 15.9018 (10) Å
b = 7.3716 (4) Å
c = 16.8376 (10) Å
= 111.644 (3)°
V = 1834.57 (19) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.937, T_max = 0.955
14168 measured reflections
3597 independent reflections
2598 reflections with I > 2(I)
R_int = 0.025

Refinement

R[F² > 2(F²)] = 0.048
wR(F²) = 0.139
S = 1.02
3597 reflections
229 parameters
H-atom parameters constrained
_max = 0.45 e Å^-3
_min = -0.40 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C13-C18 ring.

D-HA	D-H	HA	DA	D-HA
C7-H7AO2ⁱ	0.97	2.50	3.402 (4)	155
C9-H9ACg3ⁱⁱ	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); 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 (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: 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.
Shafiq, M., Khan, I. U., Arshad, M. N. & Siddiqui, W. A. (2011b). Asian J. Chem. 23, 2101-2106.
Shafiq, M., Tahir, M. N., Harrison, W. T. A., Khan, I. U. & Shafique, S. (2013). Acta Cryst. E69, o165.
Shafiq, M., Zia-Ur-Rehman, M., Khan, I. U., Arshad, M. N. & Khan, S. A. (2011a). J. Chilean Chem. Soc. 56, 527-531.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds

1-Ethyl-4-{2-[1-(4-methylphenyl)ethylidene]hydrazinylidene}-3,4-dihydro-1H-26,1-benzothiazine-2,2-dione