6-Bromo-1-methyl-4-[2-(1-phenyl­ethyl­idene)hydrazinyl­idene]-3,4-dihydro-1H-2λ6,1-benzothia­zine-2,2-dione

Shafiq, M.; Tahir, M.N.; Harrison, W.T.A.; Bukhari, I.H.; Khan, I.U.

doi:10.1107/S1600536812051380

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 (C-C) = 0.004 Å
R = 0.037
wR = 0.082
Data-to-parameter ratio = 14.7
Details

6-Bromo-1-methyl-4-[2-(1-phenylethylidene)hydrazinylidene]-3,4-dihydro-1H-2⁶,1-benzothiazine-2,2-dione

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

^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-HO 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). For further synthetic details, see: Shafiq, Khan et al. (2011).

Experimental

Crystal data

C₁₇H₁₆BrN₃O₂S
M_r = 406.30
Monoclinic, P 2₁ /c
a = 16.4369 (13) Å
b = 6.5400 (5) Å
c = 16.5025 (17) Å
= 104.312 (4)°
V = 1718.9 (3) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.518, T_max = 0.603
7358 measured reflections
3213 independent reflections
2256 reflections with I > 2(I)
R_int = 0.026

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.082
S = 1.02
3213 reflections
219 parameters
H-atom parameters constrained
_max = 0.56 e Å^-3
_min = -0.51 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1-C6 ring.

D-HA	D-H	HA	DA	D-HA
C2-H2O2ⁱ	0.93	2.49	3.280 (4)	143
C13-H13Cg2ⁱⁱ	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); 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, 1997); 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.
Shafiq, M., Khan, I. U., Arshad, M. N. & Siddiqui, W. A. (2011). Asian J. Chem. 23, 2101-2106.
Shafiq, M., Zia-Ur-Rehman, M., Khan, I. U., Arshad, M. N. & Khan, S. A. (2011). J. Chil. Chem. Soc. 56, 527-531.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds

6-Bromo-1-methyl-4-[2-(1-phenylethylidene)hydrazinylidene]-3,4-dihydro-1H-26,1-benzothiazine-2,2-dione