Methyl 3-hydr­oxy-4-oxo-3,4-dihydro-2H-1,2-benzothia­zine-3-carboxyl­ate 1,1-dioxide monohydrate

Arshad, M.N.; Tahir, M.N.; Khan, I.U.; Shafiq, M.; Siddiqui, W.A.

doi:10.1107/S1600536808030948

Volume 64
Part 10
Page o2045
October 2008

Received 21 September 2008
Accepted 25 September 2008
Online 30 September 2008

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.004 Å
R = 0.047
wR = 0.122
Data-to-parameter ratio = 16.3
Details

Methyl 3-hydroxy-4-oxo-3,4-dihydro-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide monohydrate

Muhammad Nadeem Arshad,^a M. Nawaz Tahir,^b ^* Islam Ullah Khan,^a Muhammad Shafiq ^a and Waseeq Ahmad Siddiqui ^c

^aDepartment of Chemistry, Government College University, Lahore, Pakistan,^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan, and ^cDepartment of Chemistry, University of Sargodha, Sargodha, Pakistan
Correspondence e-mail: dmntahir_uos@yahoo.com

In the molecule of the title compound, C₁₀H₉NO₆S·H₂O, the benzothiazine ring adopts an envelope conformation. An intramolecular N-HO hydrogen bond results in the formation of a nonplanar five-membered ring which has a twisted conformation. In the crystal structure, intermolecular N-HO, O-HO and C-HO hydrogen bonds link the molecules to form a three-dimensional network. There is a [pi] - [pi] contact between the benzene rings [centroid-centroid distance = 3.972 (2) Å].

Related literature

For general background, see: Shafiq, Khan et al. (2008); Shafiq, Tahir et al. (2008); Tahir et al. (2008). For related literature, see: Antsyshkina et al. (2003); Allen (2002). For bond-length data, see: Allen et al. (1987). For ring puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

C₁₀H₉NO₆S·H₂O
M_r = 289.26
Orthorhombic, P b c a
a = 7.7504 (5) Å
b = 14.5638 (9) Å
c = 21.0615 (14) Å
V = 2377.3 (3) Å³
Z = 8
Mo K radiation
= 0.30 mm^-1
T = 296 (2) K
0.24 × 0.18 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.934, T_max = 0.958
14889 measured reflections
2998 independent reflections
1895 reflections with I > 2(I)
R_int = 0.065

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.122
S = 1.01
2998 reflections
184 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.40 e Å^-3
_min = -0.32 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O6	0.78 (3)	2.43 (3)	2.744 (3)	106 (2)
N1-H1O7ⁱ	0.78 (3)	2.29 (3)	3.032 (3)	162 (3)
O4-H4OO7ⁱⁱ	0.84 (3)	1.94 (3)	2.773 (3)	175 (2)
O7-H71O3ⁱⁱⁱ	0.83 (3)	2.45 (3)	3.107 (3)	137 (3)
O7-H71O5^iv	0.83 (3)	2.45 (3)	3.028 (3)	128 (3)
O7-H72O2	0.83 (4)	2.21 (4)	3.027 (3)	167 (3)
C5-H5O4^iv	0.9300	2.4800	3.374 (3)	162.00
C10-H10AO4ⁱ	0.9600	2.3100	2.994 (3)	128.00
Symmetry codes: (i) x-1, y, z; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (iii) -x+1, -y, -z; (iv) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007); 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, 2003); 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: HK2537 ).

Acknowledgements

Muhammad Nadeem Arshad gratefully acknowledges the Higher Education Commission, Islamabad, Pakistan, for providing him with a scholarship under the Indigenous PhD Program (PIN 042-120607-PS2-183).

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.
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.
Antsyshkina, A. S., Sadikov, G. G., Korshunov, O. Yu., Anpilova, E. L., Bicherov, A. S., Sergienko, V. S., Uflyand, I. E. & Garnovskii, A. D. (2003). Russ. J. Coord. Chem. 29, 724-731.
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Shafiq, M., Khan, I. U., Tahir, M. N. & Siddiqui, W. A. (2008). Acta Cryst. E64, o558.
Shafiq, M., Tahir, M. N., Khan, I. U., Ahmad, S. & Siddiqui, W. A. (2008). Acta Cryst. E64, o1270.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
Tahir, M. N., Shafiq, M., Khan, I. U., Siddiqui, W. A. & Arshad, M. N. (2008). Acta Cryst. E64, o557.

organic compounds