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

Arshad, M.N.; Tahir, M.N.; Khan, I.U.; Bilal, M.H.; Mubashar-ur-Rehman, H.

doi:10.1107/S1600536809012021

Volume 65
Part 5
Page o986
May 2009

Received 28 March 2009
Accepted 31 March 2009
Online 8 April 2009

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.029
wR = 0.083
Data-to-parameter ratio = 16.2
Details

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 and Hafiz Mubashar-ur-Rehman ^a

^aDepartment of Chemistry, Government College University, Lahore, Pakistan, and ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan
Correspondence e-mail: dmntahir_uos@yahoo.com

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-HO interactions link the molecules into chains along the c axis. A weak C-H [pi] 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, P n a 2₁
a = 9.4120 (5) Å
b = 19.4108 (11) Å
c = 6.5261 (4) Å
V = 1192.28 (12) Å³
Z = 4
Mo K radiation
= 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 > 2(I)
R_int = 0.019

Refinement

R[F² > 2(F²)] = 0.029
wR(F²) = 0.083
S = 1.05
2525 reflections
156 parameters
1 restraint
H-atom parameters constrained
_max = 0.28 e Å^-3
_min = -0.20 e Å^-3
Absolute structure: Flack (1983), 837 Friedel pairs
Flack parameter: 0.02 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C5-H5O1ⁱ	0.93	2.56	3.391 (2)	149
C8-H8AO2ⁱⁱ	0.97	2.51	3.436 (3)	160
C3-H3Cg1ⁱⁱⁱ	0.93	2.89	3.664 (2)	141
Symmetry codes: (i) $[-x+1, -y+1, z+{\script{1\over 2}}]$ ; (ii) x, y, z-1; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ . Cg1 is the centroid of the C1-C6 ring.

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 data and figures for this paper are available from the IUCr electronic archives (Reference: HK2656 ).

Acknowledgements

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).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Arshad, M. N., Tahir, M. N., Khan, I. U., Shafiq, M. & Siddiqui, W. A. (2008). Acta Cryst. E64, o2045.
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Kruszynski, R. & Czestkowski, W. (2001). Acta Cryst. E57, o516-o518.
Primofiore, G., Da Settimo, F., La Motta, C., Simorini, F., Minutolo, A. & Boldrini, E. (1997). Farmaco, 52, 583-588.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Siddiqui, W. A., Ahmad, S., Khan, I. U., Siddiqui, H. L. & Parvez, M. (2007). Acta Cryst. E63, o4116.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Yu, G.-P., Xu, Z.-J., Xu, L.-Z. & Aisa, H. A. (2008). Acta Cryst. E64, o805.

organic compounds