2-[(Methyl-sulfan-yl)meth-yl]-1,2-benz-isothia-zol-3(2H)-one 1,1-dioxide.

In the title mol-ecule, C(9)H(9)NO(3)S(2), the essentially planar benzisothia-zole ring system and the C-S-C atoms of the methyl-sulfanyl side chain form an angle of 64.45 (7)°. The structure is devoid of any classical hydrogen bonding. However, weak non-classical inter- and intra-molecular hydrogen bonds of the type C-H⋯O are present.

Related literature

For related literature, see: Bernstein et al. (1994 ▶); Masashi et al. (1999 ▶); Nagasawa et al. (1995 ▶); Siddiqui et al. (2007a ▶,b ▶, 2008a ▶,b ▶); Xu et al. (2006 ▶); Liang (2006 ▶).

Experimental

Crystal data

C9H9NO3S2

M = 243.29

Monoclinic,

a = 7.550 (3) Å

b = 17.332 (8) Å

c = 9.455 (3) Å

β = 124.26 (2)°

V = 1022.6 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.51 mm−1

T = 173 (2) K

0.18 × 0.16 × 0.06 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.915, T max = 0.970

3975 measured reflections

2322 independent reflections

2004 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.094

S = 1.05

2322 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.45 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808028109/lh2683sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808028109/lh2683Isup2.hkl

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

C9H9NO3S2	F(000) = 504
Mr = 243.29	Dx = 1.580 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2322 reflections
a = 7.550 (3) Å	θ = 4.0–27.5°
b = 17.332 (8) Å	µ = 0.51 mm−1
c = 9.455 (3) Å	T = 173 K
β = 124.26 (2)°	Plate, colourless
V = 1022.6 (7) Å3	0.18 × 0.16 × 0.06 mm
Z = 4

Nonius KappaCCD diffractometer	2322 independent reflections
Radiation source: fine-focus sealed tube	2004 reflections with I > 2σ(I)
graphite	Rint = 0.024
ω and φ scans	θmax = 27.5°, θmin = 4.0°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −9→9
Tmin = 0.915, Tmax = 0.970	k = −22→19
3975 measured reflections	l = −12→12

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.048P)2 + 0.474P] where P = (Fo2 + 2Fc2)/3
2322 reflections	(Δ/σ)max = 0.001
136 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.45 e Å−3

Experimental. m.p. 405–406 K; IR (KBr, νmax, cm-1): CO 1731 (s), SO2 1332 and 1177; 1H-NMR (400 MHz, DMSO-d6) δ: 2.28 (s, 3H, CH3), 4.90 (s, 2H, CH2), 7.98–8.07 (m, 3H, aromatic), 8.13–8.34 (m, 1H, aromatic); 13C-NMR (100 MHz, DMSO-d6) δ: 158.3, 136.7, 135.9, 135.3, 125.9, 125.1, 121.6, 42.6, 15.5 LRMS (ES+): m/z: 244 [M]+ (63.5%).

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	1.06232 (7)	0.08010 (3)	0.35109 (5)	0.02244 (14)
S2	1.41986 (7)	0.24291 (3)	0.32581 (6)	0.02667 (14)
O1	0.9265 (2)	0.19480 (7)	−0.03395 (16)	0.0267 (3)
O2	0.9634 (2)	0.10390 (9)	0.43595 (17)	0.0340 (3)
O3	1.2696 (2)	0.04531 (9)	0.45436 (16)	0.0328 (3)
N1	1.0689 (2)	0.15451 (9)	0.24102 (18)	0.0235 (3)
C1	0.8872 (3)	0.02719 (10)	0.1645 (2)	0.0197 (3)
C2	0.8048 (3)	−0.04560 (11)	0.1537 (2)	0.0244 (4)
H2	0.8436	−0.0741	0.2530	0.029*
C3	0.6623 (3)	−0.07501 (10)	−0.0102 (2)	0.0255 (4)
H3	0.6023	−0.1248	−0.0231	0.031*
C4	0.6060 (3)	−0.03308 (11)	−0.1554 (2)	0.0249 (4)
H4	0.5069	−0.0543	−0.2655	0.030*
C5	0.6929 (3)	0.03959 (11)	−0.1413 (2)	0.0224 (4)
H5	0.6559	0.0680	−0.2404	0.027*
C6	0.8348 (3)	0.06950 (10)	0.0209 (2)	0.0192 (3)
C7	0.9421 (3)	0.14577 (10)	0.0633 (2)	0.0202 (3)
C8	1.1816 (3)	0.22693 (11)	0.3227 (2)	0.0253 (4)
H8A	1.2215	0.2273	0.4420	0.030*
H8B	1.0817	0.2704	0.2618	0.030*
C9	1.6129 (3)	0.18644 (12)	0.5098 (2)	0.0320 (4)
H9A	1.7529	0.1899	0.5261	0.038*
H9B	1.5664	0.1325	0.4916	0.038*
H9C	1.6244	0.2063	0.6117	0.038*

	U11	U22	U33	U12	U13	U23
S1	0.0225 (2)	0.0275 (2)	0.0162 (2)	−0.00213 (16)	0.01023 (18)	−0.00010 (16)
S2	0.0260 (3)	0.0289 (3)	0.0266 (2)	−0.00508 (18)	0.0157 (2)	−0.00217 (18)
O1	0.0280 (7)	0.0252 (7)	0.0258 (6)	−0.0001 (5)	0.0145 (6)	0.0052 (5)
O2	0.0433 (8)	0.0417 (8)	0.0282 (7)	−0.0045 (7)	0.0270 (6)	−0.0055 (6)
O3	0.0238 (7)	0.0406 (8)	0.0223 (6)	0.0006 (6)	0.0059 (6)	0.0055 (6)
N1	0.0253 (8)	0.0243 (8)	0.0186 (7)	−0.0056 (6)	0.0109 (6)	−0.0024 (6)
C1	0.0178 (8)	0.0236 (9)	0.0176 (7)	0.0014 (6)	0.0099 (7)	0.0003 (6)
C2	0.0266 (9)	0.0235 (9)	0.0255 (8)	0.0020 (7)	0.0160 (8)	0.0046 (7)
C3	0.0251 (9)	0.0205 (9)	0.0324 (9)	−0.0007 (7)	0.0172 (8)	−0.0016 (7)
C4	0.0222 (8)	0.0275 (9)	0.0212 (8)	−0.0011 (7)	0.0099 (7)	−0.0046 (7)
C5	0.0216 (8)	0.0258 (9)	0.0180 (8)	0.0017 (7)	0.0102 (7)	0.0012 (7)
C6	0.0169 (8)	0.0223 (8)	0.0187 (8)	0.0013 (6)	0.0101 (7)	0.0009 (6)
C7	0.0174 (8)	0.0231 (9)	0.0204 (8)	0.0017 (6)	0.0108 (7)	0.0010 (6)
C8	0.0231 (9)	0.0247 (9)	0.0272 (9)	−0.0027 (7)	0.0135 (8)	−0.0067 (7)
C9	0.0227 (9)	0.0401 (11)	0.0274 (9)	−0.0025 (8)	0.0106 (8)	−0.0025 (8)

S1—O3	1.4304 (15)	C3—C4	1.392 (3)
S1—O2	1.4306 (14)	C3—H3	0.9500
S1—N1	1.6754 (16)	C4—C5	1.392 (3)
S1—C1	1.7537 (18)	C4—H4	0.9500
S2—C8	1.804 (2)	C5—C6	1.385 (2)
S2—C9	1.804 (2)	C5—H5	0.9500
O1—C7	1.208 (2)	C6—C7	1.483 (2)
N1—C7	1.397 (2)	C8—H8A	0.9900
N1—C8	1.468 (2)	C8—H8B	0.9900
C1—C2	1.385 (3)	C9—H9A	0.9800
C1—C6	1.390 (2)	C9—H9B	0.9800
C2—C3	1.393 (3)	C9—H9C	0.9800
C2—H2	0.9500
O3—S1—O2	117.06 (9)	C6—C5—C4	118.30 (16)
O3—S1—N1	110.18 (8)	C6—C5—H5	120.9
O2—S1—N1	109.50 (9)	C4—C5—H5	120.9
O3—S1—C1	112.44 (9)	C5—C6—C1	120.09 (16)
O2—S1—C1	112.28 (9)	C5—C6—C7	126.71 (15)
N1—S1—C1	92.68 (8)	C1—C6—C7	113.20 (15)
C8—S2—C9	100.92 (9)	O1—C7—N1	123.12 (16)
C7—N1—C8	121.81 (15)	O1—C7—C6	128.06 (15)
C7—N1—S1	115.07 (12)	N1—C7—C6	108.81 (14)
C8—N1—S1	122.85 (12)	N1—C8—S2	114.65 (12)
C2—C1—C6	122.64 (16)	N1—C8—H8A	108.6
C2—C1—S1	127.13 (13)	S2—C8—H8A	108.6
C6—C1—S1	110.22 (13)	N1—C8—H8B	108.6
C1—C2—C3	116.69 (16)	S2—C8—H8B	108.6
C1—C2—H2	121.7	H8A—C8—H8B	107.6
C3—C2—H2	121.7	S2—C9—H9A	109.5
C2—C3—C4	121.45 (17)	S2—C9—H9B	109.5
C2—C3—H3	119.3	H9A—C9—H9B	109.5
C4—C3—H3	119.3	S2—C9—H9C	109.5
C5—C4—C3	120.82 (16)	H9A—C9—H9C	109.5
C5—C4—H4	119.6	H9B—C9—H9C	109.5
C3—C4—H4	119.6
O3—S1—N1—C7	116.17 (13)	C4—C5—C6—C1	0.0 (3)
O2—S1—N1—C7	−113.73 (13)	C4—C5—C6—C7	−179.11 (16)
C1—S1—N1—C7	1.06 (13)	C2—C1—C6—C5	0.8 (3)
O3—S1—N1—C8	−69.74 (16)	S1—C1—C6—C5	−178.13 (13)
O2—S1—N1—C8	60.36 (16)	C2—C1—C6—C7	−179.96 (15)
C1—S1—N1—C8	175.15 (14)	S1—C1—C6—C7	1.10 (18)
O3—S1—C1—C2	66.76 (18)	C8—N1—C7—O1	4.5 (3)
O2—S1—C1—C2	−67.75 (18)	S1—N1—C7—O1	178.63 (14)
N1—S1—C1—C2	179.89 (16)	C8—N1—C7—C6	−174.75 (14)
O3—S1—C1—C6	−114.36 (13)	S1—N1—C7—C6	−0.59 (17)
O2—S1—C1—C6	111.13 (13)	C5—C6—C7—O1	−0.4 (3)
N1—S1—C1—C6	−1.22 (13)	C1—C6—C7—O1	−179.53 (17)
C6—C1—C2—C3	−0.8 (3)	C5—C6—C7—N1	178.80 (16)
S1—C1—C2—C3	177.98 (13)	C1—C6—C7—N1	−0.37 (19)
C1—C2—C3—C4	0.0 (3)	C7—N1—C8—S2	−76.41 (19)
C2—C3—C4—C5	0.8 (3)	S1—N1—C8—S2	109.89 (14)
C3—C4—C5—C6	−0.8 (3)	C9—S2—C8—N1	−82.19 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2i	0.95	2.49	3.390 (2)	158
C9—H9B···O3	0.98	2.56	3.383 (3)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2i	0.95	2.49	3.390 (2)	158
C9—H9B⋯O3	0.98	2.56	3.383 (3)	142

Symmetry code: (i) .