2-(3-Methyl­but-2-en-1-yl)-1,2-benziso­thia­zol-3(2H)-one 1,1-dioxide

Muhammad Nadeem Arshad; M Nawaz Tahir; Islam Ullah Khan; Muhammad Humayun Bilal; Hafiz Mubashar-ur-Rehman

doi:10.1107/S1600536809012021

. 2009 Apr 8;65(Pt 5):o986. doi: 10.1107/S1600536809012021

2-(3-Methylbut-2-en-1-yl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxide

Muhammad Nadeem Arshad ^a, M Nawaz Tahir ^b,^*, Islam Ullah Khan ^a, Muhammad Humayun Bilal ^a, Hafiz Mubashar-ur-Rehman ^a

PMCID: PMC2977681 PMID: 21584024

Abstract

In the title compound, C₁₂H₁₃NO₃S, a saccharin derivative, the dihedral angle between the aromatic and isothiazole rings is 2.91 (12)°. The planar 3,3-dimethylallyl group [maximum deviation = 0.0086 (16) Å] is oriented at dihedral angles of 71.86 (7) and 74.35 (7)° with respect to the aromatic and isothiazole rings, respectively. In the crystal structure, weak intermolecular C—H⋯O interactions link the molecules into chains along the c axis. A weak C—H⋯π interaction is also present.

Related literature

For the biological activity of saccharine derivatives, see: Primofiore et al. (1997 ▶). For related structures, see: Arshad et al. (2008 ▶); Kruszynski & Czestkowski (2001 ▶); Siddiqui et al. (2007 ▶); Yu et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₂H₁₃NO₃S
M _r = 251.29
Orthorhombic,
a = 9.4120 (5) Å
b = 19.4108 (11) Å
c = 6.5261 (4) Å
V = 1192.28 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 296 K
0.32 × 0.24 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.924, T _max = 0.946
7340 measured reflections
2525 independent reflections
2304 reflections with I > 2σ(I)
R _int = 0.019

Refinement

R[F ² > 2σ(F ²)] = 0.029
wR(F ²) = 0.083
S = 1.05
2525 reflections
156 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.20 e Å⁻³
Absolute structure: Flack (1983 ▶), 837 Friedel pairs
Flack parameter: 0.02 (8)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (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: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809012021/hk2656sup1.cif

e-65-0o986-sup1.cif^{(19.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809012021/hk2656Isup2.hkl

e-65-0o986-Isup2.hkl^{(121.5KB, 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⋯O1ⁱ	0.93	2.56	3.391 (2)	149
C8—H8A⋯O2ⁱⁱ	0.97	2.51	3.436 (3)	160
C3—H3⋯Cg1ⁱⁱⁱ	0.93	2.89	3.664 (2)	141

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) . Cg1 is the centroid of the C1–C6 ring.

Acknowledgments

MNA greatfully acknowledges the Higher Education Commission, Islamabad, Pakistan, for providing him with a Scholaship under the Indigenous PhD Program (PIN 042–120607-PS2–183).

supplementary crystallographic information

Comment

The sodium salt of 1,2-benzisothiazole-3(2H)-one-1,1-dioxide is commonly known as saccharine, a sweetener. The derivatives of this compound are biologically active (Primofiore et al., 1997) and used for the syntheses of various biologically active heterocyclic compounds. We report herein the crystal structure of the title compound, (I), as part of our ongoing studies on thiazine related heterocycles (Arshad et al., 2008).

The crystal structures of 3-methylbut-2-enyl)ammonium chloride, (II) (Kruszynski & Czestkowski, 2001), 2-(chloromethyl)-1,2-benzisothiazole-1,1,3(2H) -trione, (III) (Siddiqui et al., 2007) and 2-n-butyl-1,2-benziso- thiazol-3(2H)-one, (IV) (Yu et al., 2008) have been published.

In the molecule of (I) (Fig 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C1-C6) and B (S1/N1/C1/C6/C7) are, of course, planar and they are oriented at a dihedral angle of 2.91 (12)°. So, benzisothiazole ring system is nearly coplanar. The 3,3-dimethylallyl moiety C (C8-C12) is also planar with a maximum deviation of 0.0086 (16) Å for C10 atom, and it is oriented with respect to rings A and B at dihedral angles of A/C = 74.35 (7) and B/C = 71.86 (7) °. Atoms O1, O2 and O3 are 1.2007 (17), -1.2296 (19) and -0.0441 (27) Å away from the ring plane of B, respectively.

In the crystal structure, weak intermolecular C-H···O interactions (Table 1) link the molecules into chains along the c axis, in which they may be effective in the stabilization of the structure. There also exists a weak C—H···π interaction (Table 1).

Experimental

For the preparation of the title compound, sodium salt of saccharine (1 g, 4.88 mmol) was dissolved in dimethylformamide (5 ml) in a round bottom flask (25 ml) equipped with condenser. Then, 3,3-dimethylallyl bromide (0.73 g, 4.88 mmol) was added to the solution and stirred at 353-373 K for 3 h. The progress of the reaction was observed by TLC. At completion of reaction, the mixture was poured on ice, precipitates obtained were filtered, washed with distilled water and dried. The residue was recrystalized in methanol to obtain the suitable crystals of the title compound.