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

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

doi:10.1107/S1600536812051513

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 (C-C) = 0.007 Å
R = 0.067
wR = 0.201
Data-to-parameter ratio = 13.7
Details

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

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

^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-HO interactions generate R₂²(20) loops and further C-HO 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). For further synthetic details, see: Shafiq et al. (2011b).

Experimental

Crystal data

C₁₈H₁₆ClN₃O₂S
M_r = 373.85
Monoclinic, P 2₁ /c
a = 7.2262 (5) Å
b = 13.5823 (9) Å
c = 17.9818 (12) Å
= 97.023 (4)°
V = 1751.6 (2) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.895, T_max = 0.939
8051 measured reflections
3107 independent reflections
1808 reflections with I > 2(I)
R_int = 0.043

Refinement

R[F² > 2(F²)] = 0.067
wR(F²) = 0.201
S = 1.03
3107 reflections
227 parameters
H-atom parameters constrained
_max = 0.97 e Å^-3
_min = -0.36 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C12-H12O2ⁱ	0.93	2.51	3.345 (6)	150
C15-H15O2ⁱⁱ	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); 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: 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.
Shafiq, M., Khan, I. U., Arshad, M. N. & Siddiqui, W. A. (2011b). Asian J. Chem. 23, 2101-2106.
Shafiq, M., Zia-Ur-Rehman, M., Khan, I. U., Arshad, M. N. & Khan, S. A. (2011a). JJ. Chil. Chem. Soc. 56, 527-531.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds

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