(4-Hydr­oxy-1,1-dioxo-2H-1,2-benzothia­zin-3-yl)(3-methoxy­phen­yl)methanone

Salman Gul; Hamid Latif Siddiqui; Matloob Ahmad; Masood Parvez

doi:10.1107/S1600536810011827

. 2010 Apr 2;66(Pt 5):o1021. doi: 10.1107/S1600536810011827

(4-Hydroxy-1,1-dioxo-2H-1,2-benzothiazin-3-yl)(3-methoxyphenyl)methanone

Salman Gul ^a, Hamid Latif Siddiqui ^a,^*, Matloob Ahmad ^b, Masood Parvez ^c

PMCID: PMC2979156 PMID: 21579085

Abstract

In the title compoud, C₁₆H₁₃NO₅S, the heterocyclic thiazine ring adopts a twist boat conformation with the S and N atoms displaced by 0.339 (5) and 0.322 (4) Å, respectively, on opposite sides of the mean plane formed by the remaining ring atoms. An intramolecular O—H⋯O interaction is present, forming a five-membered ring. The crystal structure is stabilized by intermolecular N—H⋯O hydrogen bonds, which result in chains along the b axis.

Related literature

For the biological activity of 1,2-benzothiazine derivatives, see: Ikeda et al. (1992 ▶); Ahmad et al. (2010 ▶); Lombardino et al. (1971 ▶, 1973 ▶); Zia-ur-Rehman et al. (2006 ▶); Siddiqui et al. (2007 ▶). For comparison bond lengths, see: Allen et al. (1987 ▶). For related structures, see: Siddiqui et al. (2008 ▶).

Experimental

Crystal data

C₁₆H₁₃NO₅S
M _r = 331.33
Monoclinic,
a = 8.1866 (3) Å
b = 7.2431 (3) Å
c = 25.2452 (9) Å
β = 95.5869 (18)°
V = 1489.84 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 295 K
0.16 × 0.12 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T _min = 0.962, T _max = 0.976
5610 measured reflections
3399 independent reflections
2795 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.056
wR(F ²) = 0.147
S = 1.09
3399 reflections
215 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.38 e Å⁻³

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 Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810011827/fl2296sup1.cif

e-66-o1021-sup1.cif^{(18.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011827/fl2296Isup2.hkl

e-66-o1021-Isup2.hkl^{(163.3KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O4	0.92 (3)	1.70 (3)	2.534 (2)	148 (3)
N1—H1N⋯O4ⁱ	0.84 (3)	2.13 (3)	2.886 (3)	151 (3)

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Symmetry code: (i) Inline graphic .

Acknowledgments

HLS is grateful to the Institute of Chemistry, University of the Punjab, for financial support.

supplementary crystallographic information

Comment

Benzothiazine dioxide derivatives have been extensively explored in the past few decades since their very first derivatives were found to be potent anti-inflammatory and analgesic agents (Lombardino et al., 1971). Benzothiazines derivatives are now known to be anti-allergy (Ikeda et al., 1992), anti-inflammatory (Lombardino et al., 1973), bactericidal (Zia-ur-Rehman et al., 2006), etc. In continuation of our research on benzothiazine compounds (Ahmad et al., 2010, Siddiqui et al., 2007), we report the synthesis and crystal structure of the title compound (I) in this paper (Fig. 1).

Bond distances (Allen et al., 1987) and angles are as expected and agree with the corresponding bond distances and angles reported in closely related compounds (Siddiqui et al., 2008). The heterocyclic thiazine ring adopts a twist boat conformation with atoms S1 and N1 displaced by 0.339 (5) and 0.322 (4) Å , respectively, on the opposite sides from the mean plane formed by the remaining ring atoms.

The structure is stabilized by N—H···O type intermolecular hydrogen bonds which result in one dimensional chains of molecules extended along the b-axis; intramolecular interactions O3—H3O···O4 are also present resulting in five membered rings (Table 1 and Fig. 2).

Experimental

2-[2-(3-Methoxyphenyl)-2-oxoethyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (5.0 g, 15.1 mmoles) was added to a solution of sodium metal (2.4 g) in dry methanol (50 ml). The mixture was subjected to reflux for half an hour. The contents of the flask were cooled to room temperature and then they were poured on ice cold HCl (50 ml, 5%). Light yellow precipitates of the title compound formed which were filtered off and washed with excess distilled water. Crystals suitable for XRD were grown in chloroform and methanol mixture (4:1). Yield = 3.7 g, 74%; m.p. = 425-427 K.