4-Methyl-N-(3-oxo-2,3-dihydro-1,2-benzisothia­zol-2-yl)benzene­sulfonamide

Corrado Rizzoli; Paola Vicini; Matteo Incerti

doi:10.1107/S1600536809003201

. 2009 Jan 31;65(Pt 2):o425–o426. doi: 10.1107/S1600536809003201

4-Methyl-N-(3-oxo-2,3-dihydro-1,2-benzisothiazol-2-yl)benzenesulfonamide

Corrado Rizzoli ^a,^*, Paola Vicini ^b, Matteo Incerti ^b

PMCID: PMC2968308 PMID: 21582013

Abstract

In the title molecule, C₁₄H₁₂N₂O₃S₂, the benzisothiazolone ring system is essentially planar and forms a dihedral angle of 67.37 (6)° with the plane of the benzene ring. In the crystal structure, molecules are linked via intermolecular N—H⋯O and C—H⋯O hydrogen bonds to form chains parallel to the b axis.

Related literature

For the chemical and biological properties of 1,2-benzisothiazol-3(2H)-one derivatives, see: Clerici et al. (2007 ▶); Siegemund et al. (2002 ▶). For 2-amino-1,2-benzisothiazol-3(2H)-one derivatives with antiplatelet/spasmolitic effects, see: Vicini et al. (1997 ▶,2000 ▶). For derivatives with antimicrobial properties, see: Vicini et al. (2002 ▶); Zani et al. (2004 ▶). For the synthesis of the title compound, see: Vicini et al. (2009 ▶). For the crystal structures of related compounds, see: Cavalca et al. (1970 ▶); Ranganathan et al. (2002 ▶); Steinfeld & Kersting (2006 ▶); Kim et al. (1996 ▶); Xu et al. (2006 ▶); Sarma & Mugesh (2007 ▶); Kolberg et al. (1999 ▶).

Experimental

Crystal data

C₁₄H₁₂N₂O₃S₂
M _r = 320.38
Monoclinic,
a = 8.051 (3) Å
b = 7.655 (3) Å
c = 23.910 (10) Å
β = 98.490 (8)°
V = 1457.4 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.38 mm⁻¹
T = 296 (2) K
0.28 × 0.26 × 0.12 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T _min = 0.892, T _max = 0.957
17685 measured reflections
3521 independent reflections
1888 reflections with I > 2σ(I)
R _int = 0.041

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.089
S = 1.01
3521 reflections
194 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and SCHAKAL (Keller, 1997 ▶); software used to prepare material for publication: SHELXL97 and PARST95 (Nardelli, 1995 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809003201/lh2764sup1.cif

e-65-0o425-sup1.cif^{(16.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003201/lh2764Isup2.hkl

e-65-0o425-Isup2.hkl^{(172.7KB, 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
N2—H2⋯O1ⁱ	0.848 (17)	1.948 (17)	2.784 (3)	168.3 (15)
C6—H6⋯O2ⁱⁱ	0.93	2.56	3.492 (3)	175

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

Acknowledgments

Financial support from the Italian MIUR (Ministero dell’Istruzione, dell’Universitá e della Ricerca) is gratefully acknowledged.

supplementary crystallographic information

Comment

Over the past decades a substantial number of 1,2-benzisothiazol-3(2H)-one derivatives have been reported to possess a wide range of biological activities including antimicrobial, antiviral, anticancer, anti-inflammatory, cartilage antidegenerative and other pharmacological activities (Clerici et al., 2007; Siegemund et al., 2002). As part of our program aimed at developing novel biologically active 1,2-benzisothiazol-3(2H)-ones, we have synthesized in the last years 2-amino-1,2-benzisothiazol-3(2H)-one derivatives resulted in the discovery of new compounds active as antiplatelet/spasmolitic agents (Vicini et al., 1997; Vicini et al., 2000) and of compounds endowed with very interesting antimicrobial properties (Vicini et al., 2002; Zani et al., 2004). Recently, in our continuing efforts to find novel effective 2-amino-1,2-benzisothiazol-3(2H)-one derivatives, we have synthesized a series of 2-(phenylsulfonyl)amino-1,2-benzisothiazol-3(2H)-ones which exhibit anti-HIV-1 activity against wild type virus and against viral strains carrying clinically relevant mutations (Vicini et al., 2009). Experimental evidences suggest non classical targets for this novel class of anti-HIV-1 agents. In order to study their binding sites at a molecular level we thought it appropriate to obtain X-ray crystallographic data for a prototype.

The molecule of the title compound (Fig. 1) shows no unusual geometric features, with the S1—N1 (1.7116 (19) Å) and S1—C1 (1.721 (2) Å) bond distances corresponding to those observed in similar structures (Cavalca et al., 1970; Ranganathan et al., 2002; Steinfeld & Kersting, 2006; Kim et al., 1996; Xu et al., 2006; Sarma & Mugesh, 2007). The N1—N2 bond distance (1.364 (2) Å) is just significantly shorter than that observed in 4,5-dimethyl-2-(3-nitrobenzenesulfonylamino)isothiazol-3(2H)-one 1,1-dioxide (1.387 (4) Å; Kolberg et al., 1999). The benzoisothiazole rings system is essentially planar (maximum deviation 0.019 (4) Å for atom C4) and forms a dihedral angle of 67.37 (6)° with the plane of the C8–C13 benzene ring. In the crystal structure (Fig. 2), molecules are linked into chains running parallel to the b axis by intermolecular N—H···O and C—H···O hydrogen bonding interactions (Table 1).

Experimental

The title compound was synthesized as described elsewhere (Vicini et al., 2009). Freshly prepared chlorocarbonylsulfenylchloride (18 mmol) in dried CCl₄ (40 ml) was added dropwise to a stirred, ice-cooled solution of 2-tosylhydrazine (20 mmol) in pyridine (18 ml). After 2 h the reaction mixture was allowed to cool to room temperature and the crude product was filtered, purified by base-acid (Na₂CO₃—HCl) exchange and silica-gel column chromatography (eluent CH₂Cl₂—EtOH 95:5 v/v). Pale yellow single crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution at room temperature.