(IUCr) Methyl 4-acetoxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

Volume 64
Part 3
Page o594
March 2008

Received 12 December 2007
Accepted 7 February 2008
Online 15 February 2008

Key indicators
Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.004 Å
R = 0.051
wR = 0.146
Data-to-parameter ratio = 15.7
Details

Methyl 4-acetoxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

Matloob Ahmad,^a Hamid Latif Siddiqui,^a ^* Saeed Ahmad,^b Muhammad Irfan Ashiq ^a and Graham John Tizzard ^c

^aInstitute of Chemistry, University of the Punjab, Lahore 54600, Pakistan,^bDepartment of Chemistry, University of Science and Technology, Bannu, Pakistan, and ^cSchool of Chemistry, University of Southampton, England
Correspondence e-mail: drhamidlatif@yahoo.com

In the title compound, C₁₃H₁₃NO₆S, the thiazine ring adopts a distorted half-chair conformation. Each molecule is linked to its neighbour through intermolecular C-HO hydrogen bonds.

Related literature

For related literature, see: Fabiola et al. (1998); Golic & Leban (1987); Kojic-Prodic & Ruzic-Toros (1982); Rajagopal & Seshadri (1990); Reck et al. (1988); Rehman et al. (2005, 2006); Turck et al. (1996).

Experimental

Crystal data

C₁₃H₁₃NO₆S
M_r = 311.30
Monoclinic, P 2₁ /c
a = 6.8917 (5) Å
b = 24.1814 (17) Å
c = 8.2861 (5) Å
= 97.876 (4)°
V = 1367.86 (16) Å³
Z = 4
Mo K radiation
= 0.26 mm^-1
T = 120 (2) K
0.40 × 0.20 × 0.20 mm

Data collection

Bruker Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007) T_min = 0.902, T_max = 0.949
12265 measured reflections
3032 independent reflections
2183 reflections with I > 2(I)
R_int = 0.057

Refinement

R[F² > 2(F²)] = 0.050
wR(F²) = 0.145
S = 1.03
3032 reflections
193 parameters
H-atom parameters constrained
_max = 0.36 e Å^-3
_min = -0.55 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C13-H13AO4ⁱ	0.98	2.48	3.387 (3)	153
C5-H5O1ⁱ	0.95	2.48	3.349 (3)	151
Symmetry code: (i) x, y, z-1.

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CAMERON (Pearce & Watkin, 1993); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KP2156 ).

Acknowledgements

The authors acknowledge financial support from the Higher Education Commission of Pakistan and the University of the Punjab, Lahore.

References

Fabiola, G. F., Pattabhi, V., Manjunatha, S. G., Rao, G. V. & Nagarajan, K. (1998). Acta Cryst. C54, 2001-2003.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Golic, L. & Leban, I. (1987). Acta Cryst. C43, 280-282.
Kojic-Prodic, B. & Ruzic-Toros, Z. (1982). Acta Cryst. B38, 2948-2951.
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Pearce, L. J. & Watkin, D. J. (1993). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.
Rajagopal, R. & Seshadri, S. (1990). Dyes Pigments, 13, 93-99.
Reck, G., Dietz, G., Laban, G., Gunter, W., Bannier, G. & Hohne, E. (1988). Pharmazie, 43, 477-481.
Rehman, M. Z., Choudary, J. A. & Ahmad, S. (2005). Bull. Korean Chem. Soc. 26, 1171-1175.
Rehman, M. Z., Choudary, J. A., Ahmad, S. & Siddiqui, H. L. (2006). Chem. Pharm. Bull. 54, 1175-1178.
Sheldrick, G. M. (2007). SADABS. Version 2007/2. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Turck, D., Busch, U., Heinzel, G., Narjes, H. & Nehmiz, G. (1996). Clin. Pharm. 36, 79-84.

organic compounds