2-Methyl-1,2-benzisothia-zol-3(2H)-one 1,1-dioxide.

All atoms of the title mol-ecule, C(8)H(7)NO(3)S, except the two oxide O atoms and two H atoms of the methyl group, lie on a crystallographic mirror plane. The crystal structure is stabilized by weak inter- and intra-molecular C-H⋯O hydrogen bonds.

Related literature

For related literature, see: Hu et al. (2004 ▶); Kap-Sun & Nicholas (1998 ▶); Liang et al. (2006 ▶); Masashi et al. (1999 ▶); Nagasawa et al. (1995 ▶); Siddiqui et al. (2006 ▶, 2007a ▶,b ▶,c ▶); Siddiqui, Ahmad, Khan & Siddiqui (2007 ▶); Siddiqui, Ahmad, Khan, Siddiqui & Ahmad (2007 ▶); Siddiqui, Ahmad, Khan, Siddiqui & Parvez (2007 ▶).

Experimental

Crystal data

C8H7NO3S

M = 197.21

Monoclinic,

a = 7.463 (7) Å

b = 6.761 (6) Å

c = 8.748 (8) Å

β = 103.78 (3)°

V = 428.7 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.35 mm−1

T = 173 (2) K

0.12 × 0.08 × 0.07 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.960, T max = 0.976

1724 measured reflections

1045 independent reflections

889 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.106

S = 1.03

1045 reflections

76 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.42 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SAPI91 (Fan, 1991 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808004637/lh2597sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808004637/lh2597Isup2.hkl

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

C8H7NO3S	F000 = 204
Mr = 197.21	Dx = 1.528 Mg m−3
Monoclinic, P21/m	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yb	Cell parameters from 1724 reflections
a = 7.463 (7) Å	θ = 3.2–27.4º
b = 6.761 (6) Å	µ = 0.35 mm−1
c = 8.748 (8) Å	T = 173 (2) K
β = 103.78 (3)º	Prism, colorless
V = 428.7 (7) Å3	0.12 × 0.08 × 0.07 mm
Z = 2

Nonius KappaCCD diffractometer	1045 independent reflections
Radiation source: fine-focus sealed tube	889 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.023
T = 173(2) K	θmax = 27.4º
ω and φ scans	θmin = 3.2º
Absorption correction: multi-scan(SORTAV; Blessing, 1997)	h = −9→9
Tmin = 0.960, Tmax = 0.976	k = −8→8
1724 measured reflections	l = −11→11

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041	H-atom parameters constrained
wR(F2) = 0.106	w = 1/[σ2(Fo2) + (0.0455P)2 + 0.2966P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
1045 reflections	Δρmax = 0.41 e Å−3
76 parameters	Δρmin = −0.42 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
S1	0.68037 (10)	0.2500	0.26611 (7)	0.0314 (2)
O1	0.2425 (3)	0.2500	0.4038 (3)	0.0416 (5)
O2	0.7324 (2)	0.0698 (2)	0.20266 (16)	0.0445 (4)
N1	0.4534 (3)	0.2500	0.2520 (3)	0.0314 (5)
C1	0.7314 (4)	0.2500	0.4722 (3)	0.0254 (5)
C2	0.9043 (4)	0.2500	0.5750 (3)	0.0337 (6)
H2	1.0141	0.2500	0.5381	0.040*
C3	0.9090 (4)	0.2500	0.7337 (3)	0.0403 (7)
H3	1.0249	0.2500	0.8079	0.048*
C4	0.7486 (4)	0.2500	0.7873 (3)	0.0379 (7)
H4	0.7566	0.2500	0.8974	0.045*
C5	0.5767 (4)	0.2500	0.6832 (3)	0.0308 (6)
H5	0.4670	0.2500	0.7203	0.037*
C6	0.5690 (3)	0.2500	0.5235 (3)	0.0251 (5)
C7	0.4012 (4)	0.2500	0.3931 (3)	0.0289 (6)
C8	0.3218 (5)	0.2500	0.0986 (3)	0.0455 (8)
H8A	0.1982	0.2500	0.1130	0.055*
H8B	0.3405	0.1341	0.0410	0.055*

	U11	U22	U33	U12	U13	U23
S1	0.0415 (4)	0.0319 (4)	0.0237 (3)	0.000	0.0133 (3)	0.000
O1	0.0284 (10)	0.0449 (13)	0.0521 (13)	0.000	0.0107 (9)	0.000
O2	0.0587 (10)	0.0435 (9)	0.0369 (8)	0.0058 (7)	0.0223 (7)	−0.0101 (7)
N1	0.0355 (12)	0.0301 (12)	0.0266 (11)	0.000	0.0031 (9)	0.000
C1	0.0319 (13)	0.0222 (12)	0.0237 (12)	0.000	0.0099 (10)	0.000
C2	0.0276 (13)	0.0367 (16)	0.0371 (14)	0.000	0.0085 (11)	0.000
C3	0.0402 (16)	0.0417 (17)	0.0340 (15)	0.000	−0.0010 (12)	0.000
C4	0.0553 (18)	0.0343 (16)	0.0238 (13)	0.000	0.0087 (12)	0.000
C5	0.0392 (15)	0.0257 (13)	0.0324 (14)	0.000	0.0181 (12)	0.000
C6	0.0280 (12)	0.0189 (12)	0.0297 (13)	0.000	0.0093 (10)	0.000
C7	0.0330 (14)	0.0221 (13)	0.0320 (13)	0.000	0.0086 (11)	0.000
C8	0.0551 (19)	0.0452 (19)	0.0284 (15)	0.000	−0.0053 (13)	0.000

S1—O2i	1.430 (2)	C2—H2	0.9500
S1—O2	1.430 (2)	C3—C4	1.386 (4)
S1—N1	1.668 (3)	C3—H3	0.9500
S1—C1	1.752 (3)	C4—C5	1.385 (4)
O1—C7	1.211 (3)	C4—H4	0.9500
N1—C7	1.380 (4)	C5—C6	1.384 (4)
N1—C8	1.462 (4)	C5—H5	0.9500
C1—C2	1.386 (4)	C6—C7	1.479 (4)
C1—C6	1.389 (4)	C8—H8A	0.9600
C2—C3	1.380 (4)	C8—H8B	0.9600
O2i—S1—O2	116.79 (14)	C4—C3—H3	119.2
O2i—S1—N1	109.63 (8)	C5—C4—C3	121.1 (3)
O2—S1—N1	109.63 (8)	C5—C4—H4	119.5
O2i—S1—C1	112.76 (8)	C3—C4—H4	119.5
O2—S1—C1	112.76 (8)	C6—C5—C4	118.2 (2)
N1—S1—C1	92.54 (12)	C6—C5—H5	120.9
C7—N1—C8	123.3 (2)	C4—C5—H5	120.9
C7—N1—S1	115.6 (2)	C5—C6—C1	119.7 (2)
C8—N1—S1	121.1 (2)	C5—C6—C7	127.0 (2)
C2—C1—C6	122.7 (2)	C1—C6—C7	113.2 (2)
C2—C1—S1	127.5 (2)	O1—C7—N1	124.0 (3)
C6—C1—S1	109.9 (2)	O1—C7—C6	127.2 (3)
C3—C2—C1	116.7 (3)	N1—C7—C6	108.8 (2)
C3—C2—H2	121.6	N1—C8—H8A	109.6
C1—C2—H2	121.6	N1—C8—H8B	109.4
C2—C3—C4	121.6 (3)	H8A—C8—H8B	109.5
C2—C3—H3	119.2
O2i—S1—N1—C7	−115.28 (8)	C3—C4—C5—C6	0.000 (1)
O2—S1—N1—C7	115.28 (8)	C4—C5—C6—C1	0.0
C1—S1—N1—C7	0.0	C4—C5—C6—C7	180.0
O2i—S1—N1—C8	64.72 (8)	C2—C1—C6—C5	0.0
O2—S1—N1—C8	−64.72 (8)	S1—C1—C6—C5	180.0
C1—S1—N1—C8	180.0	C2—C1—C6—C7	180.0
O2i—S1—C1—C2	−67.46 (9)	S1—C1—C6—C7	0.0
O2—S1—C1—C2	67.46 (9)	C8—N1—C7—O1	0.0
N1—S1—C1—C2	180.0	S1—N1—C7—O1	180.0
O2i—S1—C1—C6	112.54 (9)	C8—N1—C7—C6	180.0
O2—S1—C1—C6	−112.54 (9)	S1—N1—C7—C6	0.0
N1—S1—C1—C6	0.0	C5—C6—C7—O1	0.0
C6—C1—C2—C3	0.0	C1—C6—C7—O1	180.0
S1—C1—C2—C3	180.0	C5—C6—C7—N1	180.0
C1—C2—C3—C4	0.000 (1)	C1—C6—C7—N1	0.0
C2—C3—C4—C5	0.000 (1)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O1	0.96	2.49	2.869 (4)	104
C2—H2···O1ii	0.95	2.29	3.227 (4)	169
C8—H8B···O2iii	0.96	2.49	3.358 (3)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O1	0.96	2.49	2.869 (4)	104
C2—H2⋯O1i	0.95	2.29	3.227 (4)	169
C8—H8B⋯O2ii	0.96	2.49	3.358 (3)	151

Symmetry codes: (i) ; (ii) .