2-[2-(3-Methoxy­phen­yl)-2-oxoeth­yl]-1,2-benzisothia­zol-3(2H)-one 1,1-dioxide

Salman Gul; Hamid Latif Siddiqui; Matloob Ahmad; Muhammad Azam; Masood Parvez

doi:10.1107/S160053681000543X

. 2010 Feb 13;66(Pt 3):o618. doi: 10.1107/S160053681000543X

2-[2-(3-Methoxyphenyl)-2-oxoethyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxide

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

PMCID: PMC2983639 PMID: 21580376

Abstract

In the title compound, C₁₆H₁₃NO₅S, the benzothiazole unit is essentially planar [maximum deviation = 0.0501 (10) Å for the S atom] and is oriented at a dihedral angle of 67.85 (5)° with respect to the methoxy-substituted benzene ring. The mean plane of the methoxy group is oriented at 14.3 (3)° with respect to the benzene ring to which it is attached. In the crystal structure, weak C—H⋯O hydrogen bonds form macrocyclic rings with R ₂ ²(10) and R ₂ ²(12) motifs.

Related literature

For the use of 1,2-benzisothiazoline-3-one 1,1-dioxide (saccharine) as an intermediate in the preparation of medicinally important molecules, see: Siddiqui et al. (2006 ▶); Zia-ur-Rehman et al. (2005 ▶, 2009 ▶). For the biological activity of saccharine, see: Singh et al. (2007 ▶); Vaccarino et al. (2007 ▶); Kapui et al. (2003 ▶). For related structures, see: Ahmad et al. (2008 ▶, 2009 ▶). For hydrogen-bonding motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₆H₁₃NO₅S
M _r = 331.33
Monoclinic,
a = 8.9824 (3) Å
b = 8.5801 (4) Å
c = 19.5645 (7) Å
β = 97.942 (2)°
V = 1493.37 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 173 K
0.14 × 0.12 × 0.10 mm

Data collection

Nonius diffractometer with Bruker APEXII CCD
Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T _min = 0.967, T _max = 0.976
15084 measured reflections
3399 independent reflections
2897 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.136
S = 1.06
3399 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: HKL 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 datablocks global, I. DOI: 10.1107/S160053681000543X/lh2991sup1.cif

e-66-0o618-sup1.cif^{(18.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053681000543X/lh2991Isup2.hkl

e-66-0o618-Isup2.hkl^{(163.3KB, 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
C5—H5⋯O5ⁱ	0.95	2.53	3.404 (3)	153
C8—H8B⋯O1ⁱⁱ	0.99	2.42	3.318 (3)	150
C8—H8A⋯O2ⁱ	0.99	2.51	3.301 (3)	137

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

Acknowledgments

The authors thank the Higher Education Commission of Pakistan for financial support of this research.

supplementary crystallographic information

Comment

1,2-Benzisothiazoline-3-one 1,1-dioxide (saccharine) is an important starting material for the synthesis of different heterocyclic compounds and plays a role as an intermediate for the preparation of medicinally important molecules (Siddiqui et al., 2006; Zia-ur-Rehman et al., 2009). Various derivatives of saccharin are known to be cyclooxygenase-2 (COX-2) inhibitors (Singh et al., 2007), analgesic (Vaccarino et al., 2007), human leucocyte elastase (HLE) inhibitors (Kapui et al., 2003) etc. In continuation of our research on the synthesis of potential biologically active derivatives of benzothiazines (Ahmad et al., 2008; Ahmad et al., 2009), we herein report the crystal structure of the title compound, N-(3-methoxyphenacyl)saccharin, (I).

The structure of (I) contains discrete molecules separated by normal van der Waals distances (Fig. 1). The benzothiazole moiety (S1/N1/C1–C7) is essentially planar (maximum deviation = 0.0501 (10) Å for atom S1) and lies at an angle 67.85 (5)° with respect to the benzene ring ). The methoxy group is oriented at 14.3 (3)° with respect to the benzene ring (C10–C15). The structure is devoid of any classical hydrogen bonds. However, non-classical hydrogen bonding interactions of the type C—H···O are present in the crystal structure resulting in ten and twelve membered macrocyclic rings in R₂²(10) and R₂²(12) motifs (Bernstein et al., 1995) (Fig. 2 and Table 1).

Experimental

3-Methoxy phenacyl bromide (5.49 g, 0.024 mol) was slowly added to a suspension of sodium saccharine (5 g, 0.024 mol) in dimethylformamide (15 ml) and the mixture was stirred at 383 K for 3.0 hours under anhydrous conditions. On completion of reaction (indicated by tlc), the mixture was poured on crushed ice and the precipitates formed were filtered and washed with an excess of distilled water and cold ethanol respectively. Crystals suitable for diffraction were grown from a solution of (I) in chloroform–methanol (3:1).