[2-(2,5-Dichloro­benz­yl)-4-hy­droxy-1,1-dioxo-2H-1,2-benzothia­zin-3-yl](phen­yl)methanone

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

doi:10.1107/S160053681201481X

. 2012 Apr 13;68(Pt 5):o1359. doi: 10.1107/S160053681201481X

[2-(2,5-Dichlorobenzyl)-4-hydroxy-1,1-dioxo-2H-1,2-benzothiazin-3-yl](phenyl)methanone

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

PMCID: PMC3344491 PMID: 22590253

Abstract

In the title molecule, C₂₂H₁₅Cl₂NO₄S, the heterocyclic thiazine ring adopts a half-chair conformation, with the S and N atoms displaced by 0.343 (5) and 0.402 (5) Å, respectively, on opposite sides of the mean plane formed by the remaining ring atoms. The molecular structure is consolidated by an intramolecular O—H⋯O hydrogen bond, which generates an S(?) ring. In the crystal, the molecules are linked by C—H⋯O interactions into [010] chains.

Related literature

For background information on the activity of anti-inflammatory and analgesic oxicams, see: Lombardino et al. (1971 ▶); Soler (1985 ▶); Carty et al. (1993 ▶); Turck et al. (1995 ▶); Blackham & Owen (1975 ▶). For the biological activity of benzothiazine derivatives, see: Zia-ur-Rehman et al. (2005 ▶); Ahmad et al. (2010 ▶). For the syntheses and crystal stuctures of related benzothiazine derivatives, see: Ahmad et al. (2011 ▶); Aslam et al. (2012 ▶).

Experimental

Crystal data

C₂₂H₁₅Cl₂NO₄S
M _r = 460.32
Monoclinic,
a = 12.8172 (5) Å
b = 9.9215 (4) Å
c = 16.7155 (5) Å
β = 110.511 (2)°
V = 1990.89 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.46 mm⁻¹
T = 173 K
0.20 × 0.18 × 0.16 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T _min = 0.913, T _max = 0.930
16108 measured reflections
4592 independent reflections
3598 reflections with I > 2σ(I)
R _int = 0.055

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.118
S = 1.11
4592 reflections
272 parameters
H-atom parameters constrained
Δρ_max = 0.33 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 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681201481X/rk2344sup1.cif

e-68-o1359-sup1.cif^{(21.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201481X/rk2344Isup2.hkl

e-68-o1359-Isup2.hkl^{(220.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681201481X/rk2344Isup3.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
C3—H3⋯O4ⁱ	0.95	2.60	3.310 (4)	132
O3—H3O⋯O4	0.84	1.80	2.539 (3)	146

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Symmetry code: (i) Inline graphic .

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

Oxicam is the most recent class of non-steroidal anti-inflammatory drugs (NSAIDs) and includes molecules that are derived from 1,2-benzothiazine-1,1-dioxide nuclei which are found to be potent anti-inflammatory and analgesic agents, e.g., piroxicam (Lombardino et al., 1971), droxicam (Soler, 1985), ampiroxicam (Carty et al., 1993), meloxicam (Turck et al., 1995) and sudoxicam (Blackham & Owen, 1975), etc. Besides oxicam, a large number of benzothiazine derivatives are found to possess anti-microbial (Zia-ur-Rehman et al., 2005) and anti-oxidant activities (Ahmad et al., 2010). As part of our ongoing research we are interested in the synthesis and characterization of novel benzothiazine derivatives (Aslam et al., 2012; Ahmad et al., 2011). In this paper we report the synthesis, molecular and crystal structure of the title compound.

The bond distances and angles in the title compound (Fig. 1) agree well with the corresponding bond distances and angles reported for structures of closely related compounds (Ahmad et al., 2011; Aslam et al., 2012). The heterocyclic thiazine ring adopts a half chair conformation with atoms N1 and S1 displaced by 0.402 (5)Å and 0.343 (5)Å, respectively, on the opposite sides from the mean plane formed by the remaining ring atoms. The dihedral angle between the mean planes of benzene rings C1-C6 and C17-C22 is 31.17 (7)° while the mean planes of the benzene rings C1-C6 and C10-C15 are oriented at 35.09 (9)° with respect to each other. The molecular structure of the title compound is stabilized by intramolecular interactions O3–H3O···O4, C11–H11···N1 and C16–H16A···O2, etc, while the crystal packing is consolidated by C3–H3···O4ⁱ intermolecular nonclassical hydrogen bonds resulting in chains of molecules lying along the b-axis (Fig. 2 and Table 1). Symmetry code: (i) x, y+1, z.

Experimental

A mixture of 3-benzoyl-4-hydroxy-2H-1,2-benzothiazine 1,1-dioxide (1.0 g, 3.32 mmol), aqueous sodium hydroxide (0.26 g, 6.6 mmol) and 2-(bromomethyl)-1,4-dichlorobenzene (0.80 g, 3.32 mmol) in acetone (10 ml) was subjected to ultrasonic irradiation for 20 minutes at 318 K. The reaction mixture was then acidified to pH = 3 by using dilute hydrochloric acid. The precipitates were filtered, washed with excess of distilled water and dried at room temperature to get chrome yellow powder of the title compound (1.38 g, 90.3%). The crystals suitable for X-ray crystallographic analysis were grown from methanol by slow evaporation at room temperature.