3-(Propan-2-yl-oxy)-1,2-benzothia-zole 1,1-dioxide.

In the title compound, C(10)H(11)NO(3)S, the benzisothia-zole ring system is almost planar [maximum deviation = 0.030 (1) Å for the S atom]. The isoprop-oxy group is almost in the plane of the benzisothia-zole ring system [N-C-O-C = 4.5 (2)°] with one of its methyl groups in an anti-periplanar orientation relative to the benzisothia-zole ring system [C-C-O-C = -162.0 (2)°].

Related literature

For related structures, see: Siddiqui et al. (2007 ▶, 2008 ▶); Bassin et al. (2011 ▶); Arshad et al. (2009a ▶,b ▶).

Experimental

Crystal data

C10H11NO3S

M = 225.27

Triclinic,

a = 8.1899 (3) Å

b = 8.8361 (4) Å

c = 8.9045 (4) Å

α = 101.624 (2)°

β = 106.694 (1)°

γ = 114.898 (1)°

V = 519.89 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.30 mm−1

T = 296 K

0.13 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

9516 measured reflections

2560 independent reflections

2090 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.102

S = 1.05

2560 reflections

138 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.34 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: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶), PARST (Nardelli, 1983 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812002413/ld2045sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812002413/ld2045Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812002413/ld2045Isup3.cml

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

C10H11NO3S	Z = 2
Mr = 225.27	F(000) = 236
Triclinic, P1	Dx = 1.439 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1899 (3) Å	Cell parameters from 4072 reflections
b = 8.8361 (4) Å	θ = 2.6–28.0°
c = 8.9045 (4) Å	µ = 0.30 mm−1
α = 101.624 (2)°	T = 296 K
β = 106.694 (1)°	Prism, colourless
γ = 114.898 (1)°	0.13 × 0.10 × 0.08 mm
V = 519.89 (4) Å3

Bruker APEXII CCD diffractometer	2090 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.020
graphite	θmax = 28.4°, θmin = 2.7°
φ and ω scans	h = −10→10
9516 measured reflections	k = −11→11
2560 independent reflections	l = −11→11

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0509P)2 + 0.1198P] where P = (Fo2 + 2Fc2)/3
2560 reflections	(Δ/σ)max < 0.001
138 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.51553 (5)	0.65330 (5)	−0.19102 (5)	0.0414 (1)
O1	0.4815 (2)	0.7249 (2)	−0.31926 (16)	0.0625 (5)
O2	0.35943 (17)	0.48322 (17)	−0.21499 (18)	0.0616 (4)
O3	0.85768 (15)	0.97134 (14)	0.24607 (13)	0.0389 (3)
N1	0.58062 (18)	0.80108 (18)	−0.00718 (16)	0.0386 (4)
C1	0.7438 (2)	0.6603 (2)	−0.14202 (18)	0.0347 (4)
C2	0.8040 (2)	0.5704 (2)	−0.2379 (2)	0.0423 (5)
C3	0.9986 (3)	0.6115 (2)	−0.1638 (2)	0.0472 (6)
C4	1.1264 (2)	0.7379 (2)	−0.0035 (2)	0.0470 (6)
C5	1.0640 (2)	0.8267 (2)	0.0923 (2)	0.0402 (5)
C6	0.8694 (2)	0.78493 (19)	0.02064 (18)	0.0325 (4)
C7	0.7613 (2)	0.85598 (19)	0.08991 (18)	0.0333 (4)
C8	0.7475 (2)	1.0339 (2)	0.3210 (2)	0.0418 (5)
C9	0.9032 (3)	1.2032 (3)	0.4722 (2)	0.0561 (6)
C10	0.6175 (3)	0.8887 (3)	0.3664 (3)	0.0610 (7)
H2	0.71820	0.48640	−0.34680	0.0510*
H3	1.04400	0.55220	−0.22400	0.0570*
H4	1.25700	0.76420	0.04130	0.0560*
H5	1.15010	0.91140	0.20090	0.0480*
H8	0.66590	1.06130	0.23960	0.0500*
H9A	0.98120	1.17530	0.55260	0.0840*
H9B	0.84010	1.25380	0.52320	0.0840*
H9C	0.98750	1.28810	0.43690	0.0840*
H10A	0.53260	0.77990	0.26810	0.0910*
H10B	0.53830	0.92470	0.40760	0.0910*
H10C	0.69860	0.86850	0.45240	0.0910*

	U11	U22	U33	U12	U13	U23
S1	0.0302 (2)	0.0471 (2)	0.0359 (2)	0.0212 (2)	0.0067 (2)	0.0023 (2)
O1	0.0688 (9)	0.0846 (10)	0.0389 (7)	0.0538 (8)	0.0105 (6)	0.0162 (7)
O2	0.0311 (6)	0.0500 (7)	0.0705 (9)	0.0097 (5)	0.0136 (6)	−0.0036 (6)
O3	0.0344 (5)	0.0448 (6)	0.0316 (5)	0.0210 (5)	0.0112 (4)	0.0054 (4)
N1	0.0319 (6)	0.0444 (7)	0.0358 (7)	0.0225 (6)	0.0112 (5)	0.0055 (5)
C1	0.0307 (7)	0.0378 (8)	0.0358 (7)	0.0185 (6)	0.0146 (6)	0.0110 (6)
C2	0.0446 (8)	0.0425 (8)	0.0403 (8)	0.0232 (7)	0.0208 (7)	0.0095 (7)
C3	0.0496 (9)	0.0551 (10)	0.0560 (10)	0.0350 (8)	0.0335 (8)	0.0211 (8)
C4	0.0359 (8)	0.0632 (11)	0.0544 (10)	0.0311 (8)	0.0231 (7)	0.0256 (9)
C5	0.0316 (7)	0.0491 (9)	0.0385 (8)	0.0205 (7)	0.0138 (6)	0.0149 (7)
C6	0.0303 (7)	0.0364 (7)	0.0336 (7)	0.0179 (6)	0.0154 (6)	0.0133 (6)
C7	0.0319 (7)	0.0345 (7)	0.0326 (7)	0.0177 (6)	0.0130 (6)	0.0099 (6)
C8	0.0444 (8)	0.0458 (9)	0.0352 (8)	0.0281 (7)	0.0147 (7)	0.0062 (7)
C9	0.0649 (12)	0.0509 (10)	0.0402 (9)	0.0286 (9)	0.0160 (8)	0.0048 (8)
C10	0.0610 (11)	0.0629 (12)	0.0602 (12)	0.0292 (10)	0.0367 (10)	0.0139 (10)

S1—O1	1.4278 (15)	C8—C9	1.508 (3)
S1—O2	1.4264 (16)	C8—C10	1.500 (3)
S1—N1	1.6493 (14)	C2—H2	0.9300
S1—C1	1.7642 (19)	C3—H3	0.9300
O3—C7	1.3101 (18)	C4—H4	0.9300
O3—C8	1.477 (2)	C5—H5	0.9300
N1—C7	1.290 (2)	C8—H8	0.9800
C1—C2	1.379 (2)	C9—H9A	0.9600
C1—C6	1.384 (2)	C9—H9B	0.9600
C2—C3	1.385 (3)	C9—H9C	0.9600
C3—C4	1.377 (2)	C10—H10A	0.9600
C4—C5	1.387 (3)	C10—H10B	0.9600
C5—C6	1.382 (3)	C10—H10C	0.9600
C6—C7	1.478 (3)
O1—S1—O2	117.54 (9)	C1—C2—H2	122.00
O1—S1—N1	109.42 (8)	C3—C2—H2	122.00
O1—S1—C1	110.06 (9)	C2—C3—H3	119.00
O2—S1—N1	109.04 (8)	C4—C3—H3	119.00
O2—S1—C1	112.19 (9)	C3—C4—H4	119.00
N1—S1—C1	96.54 (8)	C5—C4—H4	119.00
C7—O3—C8	117.70 (14)	C4—C5—H5	121.00
S1—N1—C7	109.19 (13)	C6—C5—H5	121.00
S1—C1—C2	130.80 (12)	O3—C8—H8	110.00
S1—C1—C6	106.85 (13)	C9—C8—H8	110.00
C2—C1—C6	122.32 (17)	C10—C8—H8	110.00
C1—C2—C3	116.66 (15)	C8—C9—H9A	109.00
C2—C3—C4	121.7 (2)	C8—C9—H9B	109.00
C3—C4—C5	121.20 (18)	C8—C9—H9C	109.00
C4—C5—C6	117.64 (15)	H9A—C9—H9B	110.00
C1—C6—C5	120.49 (16)	H9A—C9—H9C	109.00
C1—C6—C7	109.38 (15)	H9B—C9—H9C	110.00
C5—C6—C7	130.13 (14)	C8—C10—H10A	109.00
O3—C7—N1	124.94 (16)	C8—C10—H10B	109.00
O3—C7—C6	117.08 (15)	C8—C10—H10C	109.00
N1—C7—C6	117.98 (14)	H10A—C10—H10B	110.00
O3—C8—C9	105.62 (16)	H10A—C10—H10C	109.00
O3—C8—C10	108.91 (16)	H10B—C10—H10C	110.00
C9—C8—C10	113.00 (16)
O1—S1—N1—C7	−114.21 (14)	C2—C1—C6—C7	−179.48 (15)
O2—S1—N1—C7	115.99 (13)	S1—C1—C6—C5	−176.95 (13)
C1—S1—N1—C7	−0.22 (13)	S1—C1—C2—C3	177.44 (14)
O1—S1—C1—C2	−65.92 (19)	C6—C1—C2—C3	−0.4 (3)
O2—S1—C1—C2	66.96 (19)	S1—C1—C6—C7	2.25 (16)
N1—S1—C1—C2	−179.38 (17)	C2—C1—C6—C5	1.3 (3)
O1—S1—C1—C6	112.15 (13)	C1—C2—C3—C4	−1.0 (3)
O2—S1—C1—C6	−114.97 (13)	C2—C3—C4—C5	1.5 (3)
N1—S1—C1—C6	−1.30 (13)	C3—C4—C5—C6	−0.5 (3)
C8—O3—C7—N1	4.5 (2)	C4—C5—C6—C7	−179.86 (16)
C8—O3—C7—C6	−175.82 (13)	C4—C5—C6—C1	−0.8 (2)
C7—O3—C8—C10	76.34 (18)	C5—C6—C7—N1	176.34 (17)
C7—O3—C8—C9	−162.02 (15)	C1—C6—C7—O3	177.57 (14)
S1—N1—C7—C6	1.72 (19)	C1—C6—C7—N1	−2.8 (2)
S1—N1—C7—O3	−178.64 (13)	C5—C6—C7—O3	−3.3 (3)