4-Hydrazinyl­idene-1-methyl-3H-2λ6,1-benzothia­zine-2,2-dione

Shafiq, M.; Khan, I.U.; Zia-ur-Rehman, M.; Arshad, M.N.; Asiri, A.M.

doi:10.1107/S1600536811027577

Volume 67
Part 8
Page o2038
August 2011

Received 26 June 2011
Accepted 9 July 2011
Online 16 July 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.002 Å
R = 0.036
wR = 0.111
Data-to-parameter ratio = 17.0
Details

4-Hydrazinylidene-1-methyl-3H-2⁶,1-benzothiazine-2,2-dione

Muhammad Shafiq,^a Islam Ullah Khan,^a Muhammad Zia-ur-Rehman,^b Muhammad Nadeem Arshad ^c ^*⁺ and Abdullah M. Asiri ^d

^aMaterials Chemistry Laboratory, Department of Chemistry, GC University, Lahore 54000, Pakistan,^bApplied Chemistry Research Center, PCSIR Laboratories Complex, Ferozpur Road, Lahore 54600, Pakistan,^cX-ray Diffraction and Physical Laboratory, Department of Physics, School of Physical Sciences, University of the Punjab, Quaid-e-Azam Campus, Lahore 54590, Pakistan, and ^dThe Center of Excellence for Advanced Materials Research, King Abdul Aziz University, Jeddah, PO Box 80203, Saudi Arabia
Correspondence e-mail: mnachemist@hotmail.com

In the title compound, C₉H₁₁N₃O₂S, the thiazine ring adopts a half-chair conformation. In the crystal structure N-HN hydrogen bonds connect two molecules into a centrosymmetric dimer, forming an R₂²(6) ring motif. These dimers are further connected into chains by N-HO and C-HO hydrogen bonds.

Related literature

For the synthesis of the title compound, see: Shafiq et al. (2011b). For information on 1,2 and 2,1-benzothiazine, see: Shafiq et al. (2011a); Arshad et al. (2011). For related structures, see: Tahir et al. (2008); Khan et al. (2010); Shafiq et al. (2009); Arshad et al. (2009). For graph-set notation of hydrogen bonds, see: Bernstein et al. (1995).

Experimental

Crystal data

C₉H₁₁N₃O₂S
M_r = 225.27
Monoclinic, P 2₁ /n
a = 6.6643 (2) Å
b = 9.6834 (3) Å
c = 15.5890 (5) Å
= 97.699 (1)°
V = 996.94 (5) Å³
Z = 4
Mo K radiation
= 0.31 mm^-1
T = 296 K
0.41 × 0.22 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007) T_min = 0.884, T_max = 0.947
8966 measured reflections
2426 independent reflections
2114 reflections with I > 2(I)
R_int = 0.020

Refinement

R[F² > 2(F²)] = 0.036
wR(F²) = 0.111
S = 0.93
2426 reflections
143 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.30 e Å^-3
_min = -0.29 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H1NO1ⁱ	0.86 (2)	2.46 (2)	3.221 (2)	147.7 (17)
N3-H2NN2ⁱⁱ	0.790 (19)	2.376 (19)	3.094 (2)	151.8 (19)
C8-H8AO1ⁱ	0.97	2.59	3.4178 (19)	144
Symmetry codes: (i) $[-x+{\script{5\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+3, -y, -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 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5565 ).

Acknowledgements

The authors acknowledge the Higher Education Commission of Pakistan for providing a grant for the project to strengthen the Materials Chemistry Laboratory at GC University Lahore, Pakistan.

References

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