1-(4-Chloro­phen­yl)-2-[4-hy­droxy-3-(3-meth­oxy­benzo­yl)-1,1-dioxo-2H-1λ6,2-benzothia­zin-2-yl]ethanone

Siddiqui, H.L.; Ahmad, M.; Gul, S.; Ashraf, C.M.; Parvez, M.

doi:10.1107/S160053681201029X

Volume 68
Part 4
Pages o1058-o1059
April 2012

Received 24 February 2012
Accepted 8 March 2012
Online 14 March 2012

Key indicators
Single-crystal X-ray study
T = 123 K
Mean (C-C) = 0.004 Å
R = 0.054
wR = 0.111
Data-to-parameter ratio = 15.8
Details

1-(4-Chlorophenyl)-2-[4-hydroxy-3-(3-methoxybenzoyl)-1,1-dioxo-2H-1⁶,2-benzothiazin-2-yl]ethanone

Hamid Latif Siddiqui,^a ^* Matloob Ahmad,^b Salman Gul,^a Chaudhary Muhammad Ashraf ^a and Masood Parvez ^c

^aInstitute of Chemistry, University of the Punjab, Lahore 54590, Pakistan,^bChemistry Department, Govt. College University, Faisalabad, Pakistan, and ^cDepartment of Chemistry, The University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4
Correspondence e-mail: drhamidlatif@hotmail.com

In the title molecule, C₂₄H₁₈ClNO₆S, the heterocyclic thiazine ring adopts a half-chair conformation with the S and N atoms displaced by 0.406 (5) and 0.444 (5) Å, respectively, on opposite sides of the mean plane formed by the remaining ring atoms. The methoxybenzoyl and the chlorophenyl rings lie roughly parallel to each other, with a dihedral angle between the mean planes of these rings of 8.86 (10)°. The molecular structure is consolidated by intramolecular O-HO and C-HO interactions and the crystal packing is stabilized by intermolecular O-HO and C-HCl hydrogen bonds.

Related literature

For background information on the synthesis of related compounds, see: Siddiqui et al. (2007). For the biological activity of benzothiazine derivatives, see: Turck et al. (1995); Zia-ur-Rehman et al. (2006); Ahmad et al. (2010). For studies of benzothiazines as precursors for azodisperse dyes for polyesters, see: Rajagopal & Seshadri (1990). For a related structure, see: Siddiqui et al. (2008).

Experimental

Crystal data

C₂₄H₁₈ClNO₆S
M_r = 483.90
Triclinic, $[P \overline 1]$
a = 7.2656 (2) Å
b = 11.4237 (4) Å
c = 12.8997 (5) Å
= 97.147 (2)°
= 96.934 (2)°
= 91.166 (2)°
V = 1053.91 (6) Å³
Z = 2
Mo K radiation
= 0.33 mm^-1
T = 123 K
0.20 × 0.12 × 0.02 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1997) T_min = 0.938, T_max = 0.994
8755 measured reflections
4729 independent reflections
3796 reflections with I > 2(I)
R_int = 0.041

Refinement

R[F² > 2(F²)] = 0.054
wR(F²) = 0.111
S = 1.09
4729 reflections
300 parameters
H-atom parameters constrained
_max = 0.40 e Å^-3
_min = -0.46 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O3-H3OO4ⁱ	0.84	2.32	2.926 (3)	129
C3-H3Cl1ⁱⁱ	0.95	2.78	3.711 (3)	167
O3-H3OO4	0.84	1.81	2.546 (3)	145
C24-H24O2	0.95	2.60	3.534 (3)	169
Symmetry codes: (i) -x+1, -y, -z; (ii) x-1, y-1, z.

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); 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); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2395 ).

Acknowledgements

The authors are grateful to the Higher Education Commission, Pakistan, and the Institute of Chemistry, University of the Punjab, Lahore, Pakistan, for financial support.

References

Ahmad, M., Siddiqui, H. L., Zia-ur-Rehman, M. & Parvez, M. (2010). Eur. J. Med. Chem. 45, 698-704.
Blessing, R. H. (1997). J. Appl. Cryst. 30, 421-426.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Hooft, R. (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.
Rajagopal, R. & Seshadri, S. (1990). Dyes Pigm. 13, 93-105.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Siddiqui, W. A., Ahmad, S., Khan, I. U., Siddiqui, H. L. & Weaver, G. W. (2007). Synth. Commun. 37, 767-773.
Siddiqui, W. A., Ahmad, S., Tariq, M. I., Siddiqui, H. L. & Parvez, M. (2008). Acta Cryst. C64, o4-o6.
Turck, D., Busch, U., Heinzel, G., Narjes, H. & Nehmiz, G. (1995). Clin. Drug Invest. 9, 270-276.
Zia-ur-Rehman, M., Choudary, J. A., Ahmad, S. & Siddiqui, H. L. (2006). Chem. Pharm. Bull. 54, 1175-1178.