2-(Prop-2-en-yl)-1,2-benzisothia-zol-3(2H)-one 1,1-dioxide.

In the title compound, C(10)H(9)NO(3)S, the benzisothia-zole group is almost planar (with a maximum deviation of 1.61 Å). The crystal structure is stabilized by weak inter-molecular C-H⋯O hydrogen bonds, forming a chain of mol-ecules 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 = 223.24

Triclinic,

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[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.118

S = 1.06

2342 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.26 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H9NO3S	Z = 2
Mr = 223.24	F(000) = 232
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0542P)2 + 0.1101P] where P = (Fo2 + 2Fc2)/3
2342 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .