(2-Bromo­phen­yl)(4-hy­droxy-1,1-dioxo-2H-1,2-benzothia­zin-3-yl)methanone

Nazia Sattar; Hamid Latif Siddiqui; Waseeq Ahmad Siddiqui; Muhammad Akram; Masood Parvez

doi:10.1107/S1600536812013281

. 2012 Mar 31;68(Pt 4):o1247. doi: 10.1107/S1600536812013281

(2-Bromophenyl)(4-hydroxy-1,1-dioxo-2H-1,2-benzothiazin-3-yl)methanone

Nazia Sattar ^a, Hamid Latif Siddiqui ^a,^*, Waseeq Ahmad Siddiqui ^b, Muhammad Akram ^c, Masood Parvez ^d

PMCID: PMC3344176 PMID: 22606179

Abstract

In the title molecule, C₁₅H₁₀BrNO₄S, the heterocyclic thiazine ring adopts a half-chair conformation, with the S and N atoms displaced by 0.554 (7) and 0.198 (8) Å, respectively, on opposite sides of the mean plane formed by the remaining ring atoms. The molecular structure is consolidated by intramolecular O—H⋯O interactions and the crystal packing features N—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For the first synthesis of benzothiazine, see: Braun (1923 ▶). For background information on the synthesis of related compounds, see: Siddiqui et al. (2007 ▶). For the biological activity of 1,2-benzothiazine derivatives, see: Lombardino & Wiseman (1972 ▶); Gupta et al. (1993 ▶, 2002 ▶); Zia-ur-Rehman et al. (2006 ▶); Ahmad et al. (2010 ▶). For related structures, see: Siddiqui et al. (2008 ▶).

Experimental

Crystal data

C₁₅H₁₀BrNO₄S
M _r = 380.21
Monoclinic,
a = 12.0433 (4) Å
b = 8.5491 (3) Å
c = 14.7841 (5) Å
β = 106.3950 (19)°
V = 1460.27 (9) Å³
Z = 4
Mo Kα radiation
μ = 2.98 mm⁻¹
T = 173 K
0.14 × 0.12 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T _min = 0.681, T _max = 0.797
6205 measured reflections
3339 independent reflections
2528 reflections with I > 2σ(I)
R _int = 0.043

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.106
S = 1.10
3339 reflections
203 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.61 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 datablock(s) global, I. DOI: 10.1107/S1600536812013281/aa2054sup1.cif

e-68-o1247-sup1.cif^{(18.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013281/aa2054Isup2.hkl

e-68-o1247-Isup2.hkl^{(160.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812013281/aa2054Isup3.cml

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
N1—H1N⋯O4ⁱ	0.81 (5)	2.08 (5)	2.861 (4)	160 (4)
C13—H13⋯O2ⁱⁱ	0.95	2.59	3.305 (5)	132
O3—H3O⋯O4	0.84	1.80	2.530 (4)	145

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

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

supplementary crystallographic information

Comment

Since the time first benzothiazine was synthesized (Braun, 1923), thousands of its derivatives have been prepared to determine their pharmacological and other commercial uses. Among nine isomers, the 1,2-benzothiazine 1,1-dioxide nuclei possess dynamic structural features and exhibit a wide range of biological activities, e.g., anti-inflammatory (Lombardino & Wiseman, 1972), analgesic (Gupta et al., 2002), anticancer (Gupta et al., 1993) and antibacterial (Zia-ur-Rehman et al., 2006). In continuation of our research on the synthesis of biologically active benzothiazine derivatives (Siddiqui et al., 2007; Ahmad et al., 2010) herein, we report the synthesis and crystal structure of the title compound.

The bond distances and angles in the title compound (Fig. 1) agree very well with the corresponding bond distances and angles reported in closely related compounds (Siddiqui et al., 2008). The heterocyclic thiazine ring adopts a half chair conformation with atoms N1 and S1 displaced by 0.198 (8) and 0.554 (7) Å, respectively, on the opposite sides from the mean plane formed by the remaining ring atoms. The molecular structure is stabilized by intramolecular hydrogen bonds O3–H3O···O4 and the crystal packing is consolidated by N1—H1N···O4 and C13—H13···O2 intermolecular hydrogen bonds (Fig. 2 and Table 1).

Experimental

A mixture of 2-[2-(o-bromophenyl)-2oxoethyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (1.8 g, 4.7 mmol) and sodium methoxide (1.9 g, 34.8 mmol) in freshly dried methanol (20 ml) was subjected to reflux for 30 minutes. The reaction was quenched with ice-cold water and acidified to pH = 3 with dilute HCl. The precipitate was filtered, washed with water and ethanol (25 ml, each) to get yellow powder of the title compound (1.3 g, 72%). The crystals suitable for X-ray crystallographic analysis were grown from a mixture of solvents chloroform and methanol (1:2) by slow evaporation at room temperature (m.p. 432–434 K).