2-(2-Oxo-2-phenyl­ethyl)-1,2-benziso­thia­zol-3(2H)-one 1,1-dioxide

Matloob Ahmad; Hamid Latif Siddiqui; Muhammad Azam; Iftikhar Hussain Bukhari; Masood Parvez

doi:10.1107/S1600536810005404

. 2010 Feb 13;66(Pt 3):o616. doi: 10.1107/S1600536810005404

2-(2-Oxo-2-phenylethyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxide

Matloob Ahmad ^a, Hamid Latif Siddiqui ^a,^*, Muhammad Azam ^b, Iftikhar Hussain Bukhari ^c, Masood Parvez ^d

PMCID: PMC2983549 PMID: 21580374

Abstract

In the title compound, C₁₅H₁₁NO₄S, the benzothiazole unit is essentially planar [maximum deviation = 0.0644 (14) Å for the N atom] and forms a dihedral angle 54.43 (6)° with the phenyl ring. In the crystal structure, weak bifurcated C—H⋯O hydrogen bonds involving the carbonyl O atoms as acceptors result in R ₂ ²(7) ring 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

C₁₅H₁₁NO₄S
M _r = 301.31
Monoclinic,
a = 8.0730 (2) Å
b = 9.1270 (3) Å
c = 18.0143 (6) Å
β = 95.4616 (18)°
V = 1321.31 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 173 K
0.18 × 0.14 × 0.10 mm

Data collection

Nonius diffractometer with Bruker APEXII CCD
Absorption correction: multi-scan (SORTAV;Blessing, 1997 ▶) T _min = 0.955, T _max = 0.974
15562 measured reflections
3016 independent reflections
2554 reflections with (I) > 2.0 σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.115
S = 1.09
3016 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Data collection: COLLECT (Hooft, 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/S1600536810005404/lh2990sup1.cif

e-66-0o616-sup1.cif^{(18.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810005404/lh2990Isup2.hkl

e-66-0o616-Isup2.hkl^{(145KB, 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
C8—H8A⋯O1ⁱ	0.99	2.41	3.318 (3)	153
C15—H15⋯O1ⁱ	0.95	2.47	3.417 (3)	178

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Symmetry code: (i) Inline graphic .

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-phenacylsaccharin, (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 = 0.0644 (14) Å for N1-atom) and lies at an angle 54.43 (6) ° with respect to the phenyl 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 involving O1 and H-atoms bonded to C8 and C15 resulting in a seven membered ring in R₂²(7) motif (Bernstein et al., 1995) (Fig. 2 and Table 1).

Experimental

Phenacyl bromide (4.85 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 hours under anhydrous conditions. On completion of reaction (as indicated by tlc), the mixture was poured on crushed ice and the precipitates formed were filtered and washed with excess of distilled water and cold ethanol respectively. The crystals of N-phenacylsaccharin suitable for XRD were grown from a solution of chloroform-methanol (3:1).