2-[2-(3-Chloro­phen­yl)-2-oxoeth­yl]-4-hy­droxy-3-(3-meth­oxy­benzo­yl)-2H-1λ6,2-benzothia­zine-1,1-dione

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

doi:10.1107/S1600536812009014

. 2012 Mar 7;68(Pt 4):o980–o981. doi: 10.1107/S1600536812009014

2-[2-(3-Chlorophenyl)-2-oxoethyl]-4-hydroxy-3-(3-methoxybenzoyl)-2H-1λ⁶,2-benzothiazine-1,1-dione

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

PMCID: PMC3343952 PMID: 22590033

Abstract

In the title molecule, C₂₄H₁₈ClNO₆S, the heterocyclic thiazine ring adopts a half chair conformation with the S and N atoms displaced by 0.318 (3) and 0.387 (3) Å, respectively, on the opposite sides from the mean plane formed by the remaining ring atoms. The benzene rings of the benzothiazin unit and methoxybenzoyl group are more or less coplanar, the dihedral angle between the mean planes of these rings being 12.37 (10)° while the chlorophenyl ring is inclined at 81.87 (4) and 73.30 (5)°, respectively, to these rings. The molecular structure is consolidated by intramolecular O—H⋯O and C—H⋯N interactions and the crystal packing is stabilized by weak intermolecular C—H⋯O 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 a related structure, see: Siddiqui et al. (2008 ▶).

Experimental

Crystal data

C₂₄H₁₈ClNO₆S
M _r = 483.90
Triclinic,
a = 10.2562 (3) Å
b = 10.9602 (3) Å
c = 11.3861 (4) Å
α = 116.5460 (15)°
β = 105.3216 (13)°
γ = 97.2383 (14)°
V = 1059.17 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 173 K
0.16 × 0.10 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T _min = 0.950, T _max = 0.975
8854 measured reflections
4806 independent reflections
4317 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.102
S = 1.04
4806 reflections
300 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.44 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/S1600536812009014/pk2394sup1.cif

e-68-0o980-sup1.cif^{(30KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812009014/pk2394Isup2.hkl

e-68-0o980-Isup2.hkl^{(230.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812009014/pk2394Isup3.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
C4—H4⋯O5ⁱ	0.95	2.49	3.365 (2)	154
C17—H17A⋯O2ⁱⁱ	0.99	2.26	3.2467 (19)	174
O3—H3O⋯O4	0.84	1.70	2.4528 (18)	148
C11—H11⋯N1	0.95	2.40	2.972 (2)	118

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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. 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 (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 0.387 (3) and 0.318 (3) Å, respectively, on the opposite sides from the mean plane formed by the remaining ring atoms. The benzene rings C1–C6 and C10–C15 are more or less co-planar with a dihedral angle between the mean planes of these rings being 12.37 (10)°; the benzene ring C19–C24 is oriented at 81.87 (4) and 73.30 (5)°, respectively, with respect to these benzene rings. While the molecular structure of the title compound is consolidated by intramolecular interactions: O3–H3O···O4 and C11–H11···N1, the crystal packing is stabilized by weak intermolecular C—H···O 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 3-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 precipitates of the title compound thus formed were collected and washed with ethanol. The crystals suitable for X-ray crystallographic analysis were grown from a solution in methanol.