2-[(E)-3-Phenyl­prop-2-en­yl]-1,2-benzisothia­zol-3(2H)-one 1,1-dioxide

Muhammad Nadeem Arshad; Hafiz Mubashar-ur-Rehman; Muhammad Zia-ur-Rehman; Islam Ullah Khan; Muhammad Shafique

doi:10.1107/S1600536809012999

. 2009 Apr 8;65(Pt 5):o1011. doi: 10.1107/S1600536809012999

2-[(E)-3-Phenylprop-2-enyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxide

Muhammad Nadeem Arshad ^a, Hafiz Mubashar-ur-Rehman ^a, Muhammad Zia-ur-Rehman ^b, Islam Ullah Khan ^a,^*, Muhammad Shafique ^a

PMCID: PMC2977698 PMID: 21583834

Abstract

In the crystal structure of the title compound, C₁₆H₁₃NO₃S, the benzisothiazole group is almost planar (r.m.s. deviation for all non-H atoms excluding the two O atoms bonded to S = 0.009 Å). The dihedral angle between the fused ring and the terminal ring is 13.8 (1)°. In the crystal, molecules are linked through intermolecular C—H⋯O contacts forming a chain of molecules along b.

Related literature

For the synthesis of benzothiazine and benzisothiazol derivatives, see: Zia-ur-Rehman et al. (2006 ▶, 2009 ▶); Siddiqui et al. (2008 ▶). For the biological activity of benzisothiazols, see: Kapui et al. (2003 ▶); Liang et al. (2006 ▶). For related structures, see: Siddiqui et al. (2006 ▶, 2007a ▶,b ▶,c ▶).

Experimental

Crystal data

C₁₆H₁₃NO₃S
M _r = 299.33
Monoclinic,
a = 6.9375 (5) Å
b = 7.1579 (4) Å
c = 29.673 (2) Å
β = 96.160 (4)°
V = 1464.99 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 296 K
0.39 × 0.11 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: none
8250 measured reflections
3606 independent reflections
1722 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.178
S = 0.96
3606 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SMART (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶) and local programs.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809012999/bt2924sup1.cif

e-65-o1011-sup1.cif^{(18.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809012999/bt2924Isup2.hkl

e-65-o1011-Isup2.hkl^{(176.8KB, 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
C2—H2⋯O1ⁱ	0.93	2.29	3.174 (4)	158

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors are grateful to the Higher Education Commission of Pakistan for a grant for the purchase of diffractometer.

supplementary crystallographic information

Comment

Benzisothiazolone-1,1-dioxide and its various derivatives are well known as biologically active compounds e.g., saccharin has been identified as an important molecular component in various classes of 5-HTla antagonists, analgesics and human mast cell tryptase inhibitors (Liang et al., 2006). Few of its derivatives are considered to be the most potent orally active human leucocyte elastase (HLE) inhibitors for the treatment ofchronic obstructive pulmonary disease (COPD), acute respiratory distress syndrome (ARDS), cystic fibrosis, asthma and other inflammatory diseases (Kapui et al., 2003). Its N-alkyl derivatives have been successfully transformed to non-steroidal anti-inflammatory drugs e.g., piroxicam (Zia-ur-Rehman et al., 2006).

In continuation to our research on the synthesis of 1,2-benzothiazine 1,1-dioxide derivatives (Zia-ur-Rehman et al., 2009; Zia-ur-Rehman et al., 2006), we have in addtion, worked on the synthesis of benzisothiazole derivatives (Siddiqui et al., 2006; Siddiqui et al., 2008). Herein, crystal structure of the title compound (I) is described. The benzisothiazole moiety is exactly planar.The molecular dimensions are in accord with the corresponding dimensions reported in similar structures (Siddiqui et al., 2007a-c). Each molecule is linked to its adjacent one through C—H···O contacts forming a chain of molecules along b.

Experimental

A mixture of 2,3-dihydro-1,2-benzisothiazol-3-one-1,1-dioxide (1.83 g, 10.0 mmoles), dimethyl formamide (5.0 ml) and cinnamyl chloride (1.67 g, 10.0 mmoles) was stirred for a period of three hours at 90°C. Contents were cooled to room temperature; poured over crushed ice to get white coloured precipitates which were filtered, washed and dried. Crystallization of the white precipitates (in methanol) afforded suitable crystals for X-ray studies after recrystalization in methanol.