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

Kakanejadifard, A.; Amani, V.

doi:10.1107/S1600536808023301

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 (C-C) = 0.003 Å
R = 0.046
wR = 0.108
Data-to-parameter ratio = 16.1
Details

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

Ali Kakanejadifard ^a ^* and Vahid Amani ^b

^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-HO, O-HO and O-HN hydrogen bonds link the molecules.

Related literature

For related literature, see: Kakanejadifard, Niknam et al. (2007); Kakanejadifard, Saniei et al. (2007); Kakanejadifard & Niknam (2006); Kakanejadifard & Amani (2008). For general background, see: Jones et al. (1961); Schrauzer & Kohnle (1964); Yari et al. (2006); Hashemi et al. (2006); Ghiasvand et al. (2004, 2005); Kakanejadifard, Niknam & Zabardasti (2007); Gok & Kantekin (1997); Hughes (1981).

Experimental

Crystal data

C₈H₇N₃O₂S·2H₂O
M_r = 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 radiation
= 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) T_min = 0.859, T_max = 0.974
15018 measured reflections
2337 independent reflections
1482 reflections with I > 2(I)
R_int = 0.082

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.107
S = 1.02
2337 reflections
145 parameters
H-atom parameters constrained
_max = 0.43 e Å^-3
_min = -0.25 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1W-H1WAN11ⁱ	0.85	2.11	2.931 (2)	162
O1W-H1WAN13ⁱ	0.85	2.62	3.225 (2)	129
O1W-H1WBO2Wⁱ	0.85	2.00	2.845 (2)	171
O2W-H2WAN13ⁱⁱ	0.85	2.02	2.853 (3)	168
N4-H4O14	0.87	2.08	2.493 (2)	108
O2W-H2WBO1W	0.85	1.94	2.780 (2)	171
O12-H12O2Wⁱⁱⁱ	0.82	1.89	2.699 (2)	171
O14-H14O1W	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); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); 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

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