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Volume 64 
Part 8 
Page o1628  
August 2008  

Received 19 July 2008
Accepted 23 July 2008
Online 31 July 2008

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.003 Å
R = 0.046
wR = 0.108
Data-to-parameter ratio = 16.1
Details
Open access

(2Z,3Z)-3,4-Dihydro-2H-1,4-benzothiazine-2,3-dione dioxime dihydrate

aDepartment of Chemistry, Faculty of Science, Lorestan University, Khorramabad, Iran, and bDepartment of Chemistry, Islamic Azad University, Shahr-e-Rey Branch, Tehran, Iran
Correspondence e-mail: alikakanejadifard@yahoo.com

In the molecule of the title compound, C8H11N3O4S, the thiazine ring adopts an envelope conformation. In the crystal structure, intermolecular N-H...O, O-H...O and O-H...N hydrogen bonds link the molecules.

Related literature

For related literature, see: Kakanejadifard, Niknam et al. (2007[Kakanejadifard, A., Niknam, E., Ranjbar, B. & Naderi-Manesh, H. (2007). Synth. Commun. 37, 2753-2756.]); Kakanejadifard, Saniei et al. (2007[Kakanejadifard, A., Saniei, A., Delfani, F., Farnia, M. & Najafi, G. R. (2007). J. Heterocycl. Chem. 44, 717-718.]); Kakanejadifard & Niknam (2006[Kakanejadifard, A. & Niknam, E. (2006). Pol. J. Chem. 80, 1645-1649.]); Kakanejadifard & Amani (2008[Kakanejadifard, A. & Amani, V. (2008). Acta Cryst. E64, o1512.]). For general background, see: Jones et al. (1961[Jones, M. E. B., Thornton, D. A. & Webb, R. F. (1961). Makromol. Chem. 49, 62-66.]); Schrauzer & Kohnle (1964[Schrauzer, G. N. & Kohnle, J. (1964). Chem. Ber. 97, 3056-3063.]); Yari et al. (2006[Yari, A., Azizi, S. & Kakanejadifard, A. (2006). Sens. Actuators B, 119, 167-173.]); Hashemi et al. (2006[Hashemi, P., Rahmani, Z., Kakanejadifard, A. & Niknam, E. (2006). Anal. Sci. 21, 1297-1301.]); Ghiasvand et al. (2004[Ghiasvand, A. R., Ghaderi, R. & Kakanejadifard, A. (2004). Talanta, 62, 287-292.], 2005[Ghiasvand, A. R., Shadabi, S., Kakanejadifard, A. & Khajehkolaki, A. (2005). Bull. Korean Chem. Soc. 26, 781-785.]); Kakanejadifard, Niknam & Zabardasti (2007[Kakanejadifard, A., Niknam, E. & Zabardasti, A. (2007). J. Coord. Chem. 60, 677-681.]); Gok & Kantekin (1997[Gok, Y. & Kantekin, H. (1997). Polyhedron, 16, 2413-2420.]); Hughes (1981[Hughes, M. N. (1981). The Inorganic Chemistry of Biological Processes. New York: Wiley.]).

[Scheme 1]

Experimental

Crystal data
  • C8H7N3O2S·2H2O

  • Mr = 245.26

  • Orthorhombic, P b c a

  • a = 9.1636 (18) Å

  • b = 9.8195 (18) Å

  • c = 24.165 (4) Å

  • V = 2174.4 (7) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.30 mm-1

  • T = 120 (2) K

  • 0.5 × 0.5 × 0.1 mm

Data collection
  • Bruker SMART 1000 CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1998[Sheldrick, G. M. (1998). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.859, Tmax = 0.974

  • 15018 measured reflections

  • 2337 independent reflections

  • 1482 reflections with I > 2[sigma](I)

  • Rint = 0.082

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.107

  • S = 1.02

  • 2337 reflections

  • 145 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.43 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1W-H1WA...N11i 0.85 2.11 2.931 (2) 162
O1W-H1WA...N13i 0.85 2.62 3.225 (2) 129
O1W-H1WB...O2Wi 0.85 2.00 2.845 (2) 171
O2W-H2WA...N13ii 0.85 2.02 2.853 (3) 168
N4-H4...O14 0.87 2.08 2.493 (2) 108
O2W-H2WB...O1W 0.85 1.94 2.780 (2) 171
O12-H12...O2Wiii 0.82 1.89 2.699 (2) 171
O14-H14...O1W 0.82 1.85 2.673 (2) 179
Symmetry codes: (i) [x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]; (ii) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z].

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 1998[Bruker (1998). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2502 ).


Acknowledgements

The authors acknowledge the Research Grant Council of Lorestan University for financial support.

References

Bruker (1998). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Ghiasvand, A. R., Ghaderi, R. & Kakanejadifard, A. (2004). Talanta, 62, 287-292.  [ISI] [CrossRef] [PubMed] [ChemPort]
Ghiasvand, A. R., Shadabi, S., Kakanejadifard, A. & Khajehkolaki, A. (2005). Bull. Korean Chem. Soc. 26, 781-785.  [ChemPort]
Gok, Y. & Kantekin, H. (1997). Polyhedron, 16, 2413-2420.  [CrossRef] [ChemPort]
Hashemi, P., Rahmani, Z., Kakanejadifard, A. & Niknam, E. (2006). Anal. Sci. 21, 1297-1301.  [CrossRef]
Hughes, M. N. (1981). The Inorganic Chemistry of Biological Processes. New York: Wiley.
Jones, M. E. B., Thornton, D. A. & Webb, R. F. (1961). Makromol. Chem. 49, 62-66.  [CrossRef] [ChemPort]
Kakanejadifard, A. & Amani, V. (2008). Acta Cryst. E64, o1512.  [CSD] [CrossRef] [details]
Kakanejadifard, A. & Niknam, E. (2006). Pol. J. Chem. 80, 1645-1649.  [ChemPort]
Kakanejadifard, A., Niknam, E., Ranjbar, B. & Naderi-Manesh, H. (2007). Synth. Commun. 37, 2753-2756.  [ISI] [CrossRef] [ChemPort]
Kakanejadifard, A., Niknam, E. & Zabardasti, A. (2007). J. Coord. Chem. 60, 677-681.  [CrossRef] [ChemPort]
Kakanejadifard, A., Saniei, A., Delfani, F., Farnia, M. & Najafi, G. R. (2007). J. Heterocycl. Chem. 44, 717-718.  [ChemPort]
Schrauzer, G. N. & Kohnle, J. (1964). Chem. Ber. 97, 3056-3063.  [CrossRef] [ChemPort]
Sheldrick, G. M. (1998). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Yari, A., Azizi, S. & Kakanejadifard, A. (2006). Sens. Actuators B, 119, 167-173.  [CrossRef]


Acta Cryst (2008). E64, o1628  [ doi:10.1107/S1600536808023301 ]

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