2-(3-Oxo-3,4-dihydro-2H-1,4-benzo­thia­zin-4-yl)acetic acid monohydrate

Fun, H.-K.; Loh, W.-S.; Janardhana, G.; Khader, A.M.A.; Kalluraya, B.

doi:10.1107/S1600536809034977

Volume 65
Part 10
Pages o2358-o2359
October 2009

Received 29 August 2009
Accepted 31 August 2009
Online 5 September 2009

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.040
wR = 0.128
Data-to-parameter ratio = 30.9
Details

2-(3-Oxo-3,4-dihydro-2H-1,4-benzothiazin-4-yl)acetic acid monohydrate

Hoong-Kun Fun,^a ^*⁺ Wan-Sin Loh,^a G. Janardhana,^b A. M. A. Khader ^b and B. Kalluraya ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangothri, Mangalore 574 199, India
Correspondence e-mail: hkfun@usm.my

In the title compound, C₁₀H₉NO₃S·H₂O, the thiomorpholine ring exists in a conformation intermediate between twist-boat and half-chair. An intermolecular O-HO hydrogen bond links the acid and water molecules together. In the crystal packing, intermolecular O-HO and C-HO hydrogen bonds link the molecules into a three-dimensional network.

Related literature

For the biological activity of 4H-benzo(1,4)thiazine, see: Armenise et al. (1991); Gupta et al. (1993); Fringuelli et al. (2005). For medical applications of sulfone derivatives of 4H-benzo(1,4)thiazine, see: Shinji & Koshiro (1995); Szule et al. (1988); Culbertson (1991). For a related structure, see: Zhang et al. (2008). For bond-length data, see: Allen et al. (1987). For ring puckering parameters, see: Cremer & Pople (1975). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

C₁₀H₉NO₃S·H₂O
M_r = 241.26
Monoclinic, P 2₁ /c
a = 7.5897 (1) Å
b = 9.2208 (2) Å
c = 15.6701 (3) Å
= 94.336 (1)°
V = 1093.50 (3) Å³
Z = 4
Mo K radiation
= 0.29 mm^-1
T = 100 K
0.49 × 0.34 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.870, T_max = 0.969
25955 measured reflections
4859 independent reflections
3833 reflections with I > 2(I)
R_int = 0.036

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.128
S = 0.83
4859 reflections
157 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.54 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H1O2O1Wⁱ	0.93 (2)	1.62 (2)	2.5384 (13)	168 (3)
O1W-H2W1O3ⁱⁱ	0.85 (2)	1.96 (2)	2.7893 (13)	168 (2)
O1W-H1W1O1	0.90 (2)	1.85 (2)	2.7221 (13)	163.4 (19)
C2-H2AO1Wⁱⁱⁱ	0.93	2.51	3.3666 (15)	153
C9-H9AO2^iv	0.97	2.58	3.4429 (14)	149
Symmetry codes: (i) x+1, y, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x, y-1, z; (iv) -x+2, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; 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 and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2641 ).

Acknowledgements

HKF thanks Universiti Sains Malaysia (USM) for the Research University Golden Goose Grant (No. 1001/PFIZIK/811012). WSL thanks the Malaysian government and USM for the award of the post of Assistant Research Officer under the Research University Golden Goose Grant (No. 1001/PFIZIK/811012).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Armenise, D., Trapani, G., Arrivo, V. & Morlacchi, F. (1991). Farmaco. 46, 1023-1032.
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Culbertson, T. P. (1991). J. Heterocycl. Chem. 28, 1701-1708.
Fringuelli, R., Milanese, L. & Schiaffella, F. (2005). Mini-Rev. Med. Chem. 5, 1061-1073(13).
Gupta, R. R., Dev, P. K., Sharma, M. L., Rajoria, C. M., Gupta, A. & Nyati, M. (1993). Anti-Ca. Drugs. 4, 589-592.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shinji, S. & Koshiro, A. (1995). Biol. Pharm. Bull. 18, 586-594.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Szule, Z., Mlochow, J. & Palus, J. (1988). J. Prakt. Chem. 330, 1023-1028.
Zhang, P., Du, N., Wang, L.-Z. & Li, Y. (2008). Acta Cryst. E64, o746.

organic compounds