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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 [sigma](C-C) = 0.002 Å
R = 0.040
wR = 0.128
Data-to-parameter ratio = 30.9
Details
Open access

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

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-H...O hydrogen bond links the acid and water molecules together. In the crystal packing, intermolecular O-H...O and C-H...O 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[Armenise, D., Trapani, G., Arrivo, V. & Morlacchi, F. (1991). Farmaco. 46, 1023-1032.]); Gupta et al. (1993[Gupta, R. R., Dev, P. K., Sharma, M. L., Rajoria, C. M., Gupta, A. & Nyati, M. (1993). Anti-Ca. Drugs. 4, 589-592.]); Fringuelli et al. (2005[Fringuelli, R., Milanese, L. & Schiaffella, F. (2005). Mini-Rev. Med. Chem. 5, 1061-1073(13).]). For medical applications of sulfone derivatives of 4H-benzo(1,4)thiazine, see: Shinji & Koshiro (1995[Shinji, S. & Koshiro, A. (1995). Biol. Pharm. Bull. 18, 586-594.]); Szule et al. (1988[Szule, Z., Mlochow, J. & Palus, J. (1988). J. Prakt. Chem. 330, 1023-1028.]); Culbertson (1991[Culbertson, T. P. (1991). J. Heterocycl. Chem. 28, 1701-1708.]). For a related structure, see: Zhang et al. (2008[Zhang, P., Du, N., Wang, L.-Z. & Li, Y. (2008). Acta Cryst. E64, o746.]). For bond-length data, see: Allen et al. (1987[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.]). For ring puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C10H9NO3S·H2O

  • Mr = 241.26

  • Monoclinic, P 21 /c

  • a = 7.5897 (1) Å

  • b = 9.2208 (2) Å

  • c = 15.6701 (3) Å

  • [beta] = 94.336 (1)°

  • V = 1093.50 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.870, Tmax = 0.969

  • 25955 measured reflections

  • 4859 independent reflections

  • 3833 reflections with I > 2[sigma](I)

  • Rint = 0.036

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.54 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H1O2...O1Wi 0.93 (2) 1.62 (2) 2.5384 (13) 168 (3)
O1W-H2W1...O3ii 0.85 (2) 1.96 (2) 2.7893 (13) 168 (2)
O1W-H1W1...O1 0.90 (2) 1.85 (2) 2.7221 (13) 163.4 (19)
C2-H2A...O1Wiii 0.93 2.51 3.3666 (15) 153
C9-H9A...O2iv 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[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


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.  [PubMed] [ChemPort]
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Culbertson, T. P. (1991). J. Heterocycl. Chem. 28, 1701-1708.  [CrossRef] [ChemPort]
Fringuelli, R., Milanese, L. & Schiaffella, F. (2005). Mini-Rev. Med. Chem. 5, 1061-1073(13).  [CrossRef] [ChemPort]
Gupta, R. R., Dev, P. K., Sharma, M. L., Rajoria, C. M., Gupta, A. & Nyati, M. (1993). Anti-Ca. Drugs. 4, 589-592.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shinji, S. & Koshiro, A. (1995). Biol. Pharm. Bull. 18, 586-594.  [PubMed]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
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.  [CSD] [CrossRef] [details]


Acta Cryst (2009). E65, o2358-o2359   [ doi:10.1107/S1600536809034977 ]

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