2-(Prop-2-en­yl)-1,2-benzisothia­zol-3(2H)-one 1,1-dioxide

Arshad, M.N.; Mubashar-ur-Rehman, H.; Zia-ur-Rehman, M.; Khan, I.U.; Shafiq, M.

doi:10.1107/S1600536809016328

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1236

doi:10.1107/S1600536809016328

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2-(Prop-2-enyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxide

Muhammad Nadeem Arshad,^a Hafiz Mubashar-ur-Rehman,^a Muhammad Zia-ur-Rehman,^b Islam Ullah Khan ^a ^* and Muhammad Shafiq ^a

^aDepartment of Chemistry, Government College University, Lahore 54000, Pakistan, and ^bApplied Chemistry Research Centre, PCSIR Laboratories Complex, Ferozpur Road, Lahore 54600, Pakistan
^*Correspondence e-mail: iukhan.gcu@gmail.com

(Received 29 April 2009; accepted 30 April 2009; online 7 May 2009)

In the title compound, C₁₀H₉NO₃S, the benzisothiazole group is almost planar (with a maximum deviation of 1.61 Å). The crystal structure is stabilized by weak intermolecular C—H⋯O hydrogen bonds, forming a chain of molecules along b.

Related literature

For the synthesis of benzothiazine and benzisothiazol derivatives, see: Zia-ur-Rehman, Anwar & Ahmad (2006 ); Zia-ur-Rehman, Anwar, Ahmad & Siddiqui (2006 ); Siddiqui et al. (2007 ) Zia-ur-Rehman et al. (2009 ). For the biological activity of benzisothiazols, see: Kapui et al. (2003 ); Liang et al. (2006 ). For related structures, see: Siddiqui, Ahmad, Siddiqui et al. (2007a ,b ,c ).

Experimental

Crystal data

C₁₀H₉NO₃S
M_r = 223.24
Triclinic, $[P \overline 1]$
a = 7.2169 (8) Å
b = 7.8347 (7) Å
c = 10.3849 (12) Å
α = 105.530 (3)°
β = 91.586 (3)°
γ = 112.047 (3)°
V = 518.95 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 296 K
0.37 × 0.26 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: none
5460 measured reflections
2342 independent reflections
1728 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.118
S = 1.06
2342 reflections
136 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1ⁱ	0.93	2.36	3.216 (3)	153
Symmetry code: (i) x, y-1, z.

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: PLATON (Spek, 2009 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809016328/bt2942sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809016328/bt2942Isup2.hkl

checkCIF report

Comment top

Besides being used as a sweetener, saccharin and its various derivatives are well known for their different type of biological activities e.g., it has been identified as an important molecular component in various classes of 5-HTla antagonists, analgesics and human mast cell tryptase inhibitors (Kapui et al., 2003; Liang et al., 2006). N-alkyl derivatives of saccharin have been successfully transformed to non-steroidal anti-inflammatory drugs e.g., piroxicam and meloxicam.

As part of a research program synthesizing various bioactive benzothiazines (Zia-ur-Rehman et al., 2009; Siddiqui et al., 2007), we have in addition, worked on the synthesis of benzisothiazole derivatives. We herein report the crystal structure of the title compound (Scheme and figure 1). The benzisothiazole moiety is exactly planar. The molecular dimensions are in accord with the corresponding dimensions reported in similar structures (Siddiqui, Ahmad, Siddiqui et al., 2007a; Siddiqui, Ahmad, Siddiqui et al., 2007b; Siddiqui, Ahmad, Siddiqui et al., 2007c). Each molecule is linked to its adjacent one through C—H···O contacts forming a chain of molecules along b (Figure 2).

Related literature top

For the synthesis of benzothiazine and benzisothiazol derivatives, see: Zia-ur-Rehman, Anwar & Ahmad (2006); Zia-ur-Rehman, Anwar, Ahmad & Siddiqui (2006); Siddiqui et al. (2007) Zia-ur-Rehman et al. (2009). For the biological activity of benzisothiazols, see: Kapui et al. (2003); Liang et al. (2006). For related structures, see: Siddiqui, Ahmad, Siddiqui et al. (2007a,b,c).

Experimental top

A mixture of 2,3-dihydro-1,2-benzisothiazol-3-one-1,1-dioxide (1.83 g, 10.0 mmoles), dimethyl formamide (5.0 ml) and allyl bromide (1.20 g, 10.0 mmoles) was stirred for a period of one hour at 90°C. Contents were cooled to room temperature; poured over crushed ice to get white coloured precipitates which were filtered, washed and dried. Crystallization of the white precipitate in methanol afforded suitable crystals for X-ray studies.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2006); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids at the 50% probability level.
	Fig. 2. Perspective view of the crystal packing showing hydrogen-bonded interactions (dashed lines). H atoms not involved in hydrogen bonding have been omitted for clarity.

2-(Prop-2-enyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxide top

Crystal data top

C₁₀H₉NO₃S	Z = 2
M_r = 223.24	F(000) = 232
Triclinic, P1	D_x = 1.429 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2169 (8) Å	Cell parameters from 2362 reflections
b = 7.8347 (7) Å	θ = 3.1–27.3°
c = 10.3849 (12) Å	µ = 0.30 mm⁻¹
α = 105.530 (3)°	T = 296 K
β = 91.586 (3)°	Needles, colourless
γ = 112.047 (3)°	0.37 × 0.26 × 0.18 mm
V = 518.95 (10) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	1728 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.022
Graphite monochromator	θ_max = 27.5°, θ_min = 2.9°
ϕ and ω scans	h = −9→9
5460 measured reflections	k = −10→6
2342 independent reflections	l = −11→13

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0542P)² + 0.1101P] where P = (F_o² + 2F_c²)/3
2342 reflections	(Δ/σ)_max < 0.001
136 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₀H₉NO₃S	γ = 112.047 (3)°
M_r = 223.24	V = 518.95 (10) Å³
Triclinic, P1	Z = 2
a = 7.2169 (8) Å	Mo Kα radiation
b = 7.8347 (7) Å	µ = 0.30 mm⁻¹
c = 10.3849 (12) Å	T = 296 K
α = 105.530 (3)°	0.37 × 0.26 × 0.18 mm
β = 91.586 (3)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	1728 reflections with I > 2σ(I)
5460 measured reflections	R_int = 0.022
2342 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.118	H-atom parameters constrained
S = 1.06	Δρ_max = 0.26 e Å⁻³
2342 reflections	Δρ_min = −0.26 e Å⁻³
136 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.39784 (8)	0.35030 (7)	0.26041 (5)	0.0536 (2)
O1	0.2640 (2)	0.6659 (2)	0.09710 (17)	0.0646 (4)
O2	0.6073 (2)	0.3953 (2)	0.29080 (18)	0.0759 (5)
O3	0.2677 (3)	0.2648 (2)	0.34679 (16)	0.0726 (5)
N1	0.3652 (3)	0.5452 (2)	0.25013 (17)	0.0515 (4)
C1	0.3079 (3)	0.2289 (3)	0.0897 (2)	0.0450 (4)
C2	0.2602 (3)	0.3453 (3)	0.0270 (2)	0.0431 (4)
C3	0.1889 (3)	0.2789 (3)	−0.1090 (2)	0.0533 (5)
H3	0.1557	0.3555	−0.1521	0.064*
C4	0.1684 (3)	0.0951 (3)	−0.1791 (2)	0.0635 (6)
H4	0.1223	0.0479	−0.2713	0.076*
C5	0.2147 (3)	−0.0205 (3)	−0.1155 (3)	0.0645 (6)
H5	0.1983	−0.1442	−0.1656	0.077*
C6	0.2844 (3)	0.0433 (3)	0.0204 (2)	0.0572 (6)
H6	0.3145	−0.0347	0.0636	0.069*
C7	0.2931 (3)	0.5357 (3)	0.1224 (2)	0.0463 (5)
C8	0.4052 (4)	0.7114 (3)	0.3697 (2)	0.0642 (6)
H8A	0.4591	0.8293	0.3443	0.077*
H8B	0.5060	0.7163	0.4359	0.077*
C9	0.2176 (5)	0.6993 (4)	0.4312 (3)	0.0823 (8)
H9	0.1606	0.5989	0.4683	0.099*
C10	0.1299 (5)	0.8116 (5)	0.4373 (3)	0.0945 (9)
H10A	0.1814	0.9141	0.4015	0.113*
H10B	0.0134	0.7926	0.4777	0.113*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0584 (3)	0.0538 (3)	0.0598 (4)	0.0253 (2)	0.0088 (2)	0.0306 (3)
O1	0.0772 (10)	0.0506 (8)	0.0818 (11)	0.0342 (7)	0.0108 (8)	0.0319 (8)
O2	0.0616 (10)	0.0850 (11)	0.0897 (12)	0.0328 (8)	−0.0054 (9)	0.0362 (10)
O3	0.0904 (12)	0.0726 (10)	0.0647 (10)	0.0278 (9)	0.0214 (9)	0.0418 (9)
N1	0.0612 (10)	0.0455 (9)	0.0537 (10)	0.0248 (8)	0.0095 (8)	0.0187 (8)
C1	0.0420 (10)	0.0435 (9)	0.0588 (12)	0.0201 (8)	0.0149 (9)	0.0249 (9)
C2	0.0391 (10)	0.0428 (9)	0.0554 (11)	0.0178 (8)	0.0139 (8)	0.0243 (9)
C3	0.0468 (11)	0.0607 (12)	0.0572 (13)	0.0207 (9)	0.0085 (9)	0.0262 (10)
C4	0.0540 (13)	0.0652 (14)	0.0616 (14)	0.0180 (11)	0.0098 (11)	0.0117 (11)
C5	0.0568 (13)	0.0470 (12)	0.0819 (17)	0.0195 (10)	0.0182 (12)	0.0080 (11)
C6	0.0514 (12)	0.0468 (11)	0.0845 (17)	0.0249 (9)	0.0194 (11)	0.0285 (11)
C7	0.0452 (10)	0.0429 (10)	0.0600 (12)	0.0198 (8)	0.0134 (9)	0.0259 (9)
C8	0.0702 (15)	0.0559 (12)	0.0604 (14)	0.0234 (11)	0.0031 (11)	0.0108 (11)
C9	0.111 (2)	0.0722 (16)	0.0749 (18)	0.0451 (16)	0.0323 (16)	0.0258 (14)
C10	0.109 (2)	0.098 (2)	0.0787 (19)	0.0495 (19)	0.0176 (17)	0.0177 (17)

Geometric parameters (Å, º) top

S1—O2	1.4220 (16)	C4—C5	1.379 (3)
S1—O3	1.4253 (15)	C4—H4	0.9300
S1—N1	1.6596 (16)	C5—C6	1.374 (3)
S1—C1	1.743 (2)	C5—H5	0.9300
O1—C7	1.206 (2)	C6—H6	0.9300
N1—C7	1.385 (3)	C8—C9	1.495 (3)
N1—C8	1.467 (3)	C8—H8A	0.9700
C1—C6	1.382 (3)	C8—H8B	0.9700
C1—C2	1.384 (2)	C9—C10	1.253 (4)
C2—C3	1.376 (3)	C9—H9	0.9300
C2—C7	1.481 (3)	C10—H10A	0.9300
C3—C4	1.378 (3)	C10—H10B	0.9300
C3—H3	0.9300

O2—S1—O3	117.16 (10)	C6—C5—C4	121.4 (2)
O2—S1—N1	109.80 (9)	C6—C5—H5	119.3
O3—S1—N1	109.80 (9)	C4—C5—H5	119.3
O2—S1—C1	111.86 (10)	C5—C6—C1	116.9 (2)
O3—S1—C1	112.76 (9)	C5—C6—H6	121.5
N1—S1—C1	92.73 (8)	C1—C6—H6	121.5
C7—N1—C8	123.33 (17)	O1—C7—N1	123.46 (19)
C7—N1—S1	115.04 (13)	O1—C7—C2	127.23 (19)
C8—N1—S1	121.60 (14)	N1—C7—C2	109.31 (15)
C6—C1—C2	122.1 (2)	N1—C8—C9	111.41 (19)
C6—C1—S1	127.33 (16)	N1—C8—H8A	109.3
C2—C1—S1	110.60 (14)	C9—C8—H8A	109.3
C3—C2—C1	120.34 (18)	N1—C8—H8B	109.3
C3—C2—C7	127.38 (17)	C9—C8—H8B	109.3
C1—C2—C7	112.27 (17)	H8A—C8—H8B	108.0
C2—C3—C4	117.8 (2)	C10—C9—C8	126.1 (3)
C2—C3—H3	121.1	C10—C9—H9	116.9
C4—C3—H3	121.1	C8—C9—H9	116.9
C3—C4—C5	121.5 (2)	C9—C10—H10A	120.0
C3—C4—H4	119.3	C9—C10—H10B	120.0
C5—C4—H4	119.3	H10A—C10—H10B	120.0

O2—S1—N1—C7	112.66 (16)	C7—C2—C3—C4	−179.51 (17)
O3—S1—N1—C7	−117.16 (15)	C2—C3—C4—C5	0.9 (3)
C1—S1—N1—C7	−1.76 (15)	C3—C4—C5—C6	−0.4 (3)
O2—S1—N1—C8	−69.00 (18)	C4—C5—C6—C1	−0.6 (3)
O3—S1—N1—C8	61.18 (18)	C2—C1—C6—C5	1.2 (3)
C1—S1—N1—C8	176.58 (16)	S1—C1—C6—C5	−178.53 (15)
O2—S1—C1—C6	69.07 (19)	C8—N1—C7—O1	2.9 (3)
O3—S1—C1—C6	−65.5 (2)	S1—N1—C7—O1	−178.81 (15)
N1—S1—C1—C6	−178.31 (17)	C8—N1—C7—C2	−177.24 (16)
O2—S1—C1—C2	−110.65 (14)	S1—N1—C7—C2	1.1 (2)
O3—S1—C1—C2	114.77 (14)	C3—C2—C7—O1	−0.5 (3)
N1—S1—C1—C2	1.96 (14)	C1—C2—C7—O1	−179.66 (19)
C6—C1—C2—C3	−0.7 (3)	C3—C2—C7—N1	179.65 (18)
S1—C1—C2—C3	179.07 (14)	C1—C2—C7—N1	0.5 (2)
C6—C1—C2—C7	178.58 (16)	C7—N1—C8—C9	84.2 (3)
S1—C1—C2—C7	−1.68 (19)	S1—N1—C8—C9	−94.0 (2)
C1—C2—C3—C4	−0.4 (3)	N1—C8—C9—C10	−114.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1ⁱ	0.93	2.36	3.216 (3)	153

Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₀H₉NO₃S
M_r	223.24
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.2169 (8), 7.8347 (7), 10.3849 (12)
α, β, γ (°)	105.530 (3), 91.586 (3), 112.047 (3)
V (Å³)	518.95 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.37 × 0.26 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5460, 2342, 1728
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.118, 1.06
No. of reflections	2342
No. of parameters	136
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.26

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and Mercury (Macrae et al., 2006), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1ⁱ	0.9300	2.3600	3.216 (3)	153.00

Symmetry code: (i) x, y−1, z.

Acknowledgements

The authors are grateful to the Higher Education Commission of Pakistan for financial support to purchase the diffractometer. MNA acknowledges the Higher Education Commission, Pakistan, for providing a PhD Scholarship under PIN 042-120607-PS2–183.

References

Bruker (2007). APEX2, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kapui, Z., Varga, M., Urban-Szabo, K., Mikus, E., Szabo, T., Szeredi, J., Finance, O. & Aranyi, P. (2003). J. Pharmacol. Exp. Ther. 305, 1–9. Web of Science CrossRef PubMed Google Scholar
Liang, X., Hong, S., Ying, L., Suhong, Z. & Mark, L. T. (2006). Tetrahedron, 62, 7902–7910. Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siddiqui, W. A., Ahmad, S., Khan, I. U. & Siddiqui, H. L. (2007). Synth. Commun. 37, 767–773. Web of Science CrossRef CAS Google Scholar
Siddiqui, W. A., Ahmad, S., Siddiqui, H. L., Tariq, M. I. & Parvez, M. (2007a). Acta Cryst. E63, o4001. Web of Science CSD CrossRef IUCr Journals Google Scholar
Siddiqui, W. A., Ahmad, S., Siddiqui, H. L., Tariq, M. I. & Parvez, M. (2007b). Acta Cryst. E63, o4117. Web of Science CSD CrossRef IUCr Journals Google Scholar
Siddiqui, W. A., Ahmad, S., Siddiqui, H. L., Tariq, M. I. & Parvez, M. (2007c). Acta Cryst. E63, o4585. Web of Science CSD CrossRef IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zia-ur-Rehman, M., Anwar, J. & Ahmad, S. (2006). Bull. Korean Chem. Soc. 26, 1771–1775. Google Scholar
Zia-ur-Rehman, M., Anwar, J., Ahmad, S. & Siddiqui, H. L. (2006). Chem. Pharm. Bull. 54, 1175–1178. Web of Science PubMed CAS Google Scholar
Zia-ur-Rehman, M., Choudary, J. A., Elsegood, M. R. J., Siddiqui, H. L. & Khan, K. M. (2009). Eur. J. Med. Chem. 44, 1311–1316. Web of Science PubMed CAS Google Scholar