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

Hamid Latif Siddiqui; Matloob Ahmad; Salman Gul; Chaudhary Muhammad Ashraf; Masood Parvez

doi:10.1107/S160053681201029X

. 2012 Mar 14;68(Pt 4):o1058–o1059. doi: 10.1107/S160053681201029X

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

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

PMCID: PMC3344017 PMID: 22589926

Abstract

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—H⋯O and C—H⋯O interactions and the crystal packing is stabilized by intermolecular O—H⋯O and C—H⋯Cl 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,
a = 7.2656 (2) Å
b = 11.4237 (4) Å
c = 12.8997 (5) Å
α = 97.147 (2)°
β = 96.934 (2)°
γ = 91.166 (2)°
V = 1053.91 (6) Å³
Z = 2
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.041

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.111
S = 1.09
4729 reflections
300 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.46 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/S160053681201029X/pk2395sup1.cif

e-68-o1058-sup1.cif^{(27KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201029X/pk2395Isup2.hkl

e-68-o1058-Isup2.hkl^{(226.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681201029X/pk2395Isup3.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
O3—H3O⋯O4ⁱ	0.84	2.32	2.926 (3)	129
C3—H3⋯Cl1ⁱⁱ	0.95	2.78	3.711 (3)	167
O3—H3O⋯O4	0.84	1.81	2.546 (3)	145
C24—H24⋯O2	0.95	2.60	3.534 (3)	169

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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

Derivatives of benzothiazine have been studied for a broad range of biological activities. They are found to possess analgesic (Turck et al., 1995), antimicrobial (Zia-ur-Rehman et al., 2006) and antioxidant activities (Ahmad et al., 2010), etc. A few benzothiazines have also been studied as precursors for azodisperse dyes for polyesters (Rajagopal & Seshadri 1990). In continuation of our research on the synthesis of biologically active benzothiazine derivatives (Siddiqui et al., 2007; Ahmad et al., 2010), we herein 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 the S1 and N1 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 distance between the centroids of these rings is 3.828 (14) Å. The molecular structure of the title compound is consolidated by intramolecular interactions O3–H3O···O4 and C24—H24···O2 and the crystal packing is stabilized by intermolecular O3—H3O···O4 and C3—H3···Cl1 hydrogen bonds (Fig. 2 and Table 1).

Experimental

A mixture of (4-hydroxy-1,1-dioxido-2H-1,2-benzothiazin-3-yl)(3-methoxyphenyl) methanone (5.0 g, 0.015 mol), K₂CO₃ (2.07 g, 0.015 mol) and 4-chlorophenacyl bromide (3.50 g, 0.015 mol) in acetonitrile (30 ml) was refluxed for 3 h. The contents of the flask were poured on ice cold HCl (5%, 30 ml). The precipitate of the title compound thus formed was collected and washed with ethanol. Crystals suitable for X-ray crystallographic analysis were grown from a solution in methanol.