Isopropyl 3-oxo-2,3-dihydro-1,2-benzothia-zole-2-carboxyl-ate.

The title compound, C(11)H(11)NO(3)S, was synthesized by the reaction of benzo[d]isothia-zol-3(2H)-one with isopropanol in toluene. The benzoisothia-zolone ring system is essentially planar, with a mean deviation of 0.018 (2) Å from the least-squares plane defined by the nine constituent atoms. In the crystal, mol-ecules are linked by weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

For background to the sythesis of benzoisothia­zolone derivatives, see: Davis (1972 ▶); Elgazwy & Abdel-Sattar (2003 ▶). For the biological activity of 1, 2–benzoisothia­zolone derivatives, see: Taubert et al. (2002 ▶). For structural studies of related alkyl 3-oxo-2,3-dihydro-1,2-benzothia­zole-2-carboxyl­ate derivatives, see: Wang et al. (2011a ▶,b ▶).

Experimental

Crystal data

C11H11NO3S

M = 237.27

Orthorhombic,

a = 4.6218 (19) Å

b = 11.621 (5) Å

c = 20.510 (9) Å

V = 1101.6 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 153 K

0.68 × 0.12 × 0.07 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.830, T max = 0.980

9436 measured reflections

2897 independent reflections

2245 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.078

S = 1.00

2897 reflections

147 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.22 e Å−3

Absolute structure: Flack, (1983 ▶), 1150 Friedel pairs

Flack parameter: −0.02 (8)

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811034209/lx2199sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034209/lx2199Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811034209/lx2199Isup3.cml

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

C11H11NO3S	F(000) = 496
Mr = 237.27	Dx = 1.431 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3268 reflections
a = 4.6218 (19) Å	θ = 2.7–29.1°
b = 11.621 (5) Å	µ = 0.28 mm−1
c = 20.510 (9) Å	T = 153 K
V = 1101.6 (8) Å3	Prism, colorless
Z = 4	0.68 × 0.12 × 0.07 mm

AFC10/Saturn724+ diffractometer	2897 independent reflections
Radiation source: Rotating Anode	2245 reflections with I > 2σ(I)
graphite	Rint = 0.045
Detector resolution: 28.5714 pixels mm-1	θmax = 29.1°, θmin = 3.5°
phi and ω scans	h = −6→6
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −14→15
Tmin = 0.830, Tmax = 0.980	l = −28→26
9436 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039	H-atom parameters constrained
wR(F2) = 0.078	w = 1/[σ2(Fo2) + (0.0289P)2 + 0.116P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
2897 reflections	Δρmax = 0.26 e Å−3
147 parameters	Δρmin = −0.22 e Å−3
0 restraints	Absolute structure: Flack, (1983), 1150 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.02 (8)

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	0.56113 (12)	0.76406 (4)	0.72970 (2)	0.02649 (13)
O1	0.3920 (3)	0.45795 (12)	0.67074 (7)	0.0339 (4)
O2	0.7876 (3)	0.55858 (12)	0.59264 (7)	0.0289 (3)
O3	0.9282 (3)	0.73722 (11)	0.62359 (6)	0.0303 (3)
N1	0.5743 (4)	0.64449 (13)	0.67914 (8)	0.0231 (4)
C1	0.3073 (4)	0.69457 (17)	0.77902 (10)	0.0258 (5)
C2	0.1822 (4)	0.73839 (18)	0.83559 (10)	0.0285 (5)
H2	0.2327	0.8124	0.8516	0.034*
C3	−0.0175 (5)	0.67062 (18)	0.86754 (11)	0.0333 (6)
H3	−0.1053	0.6986	0.9063	0.040*
C4	−0.0940 (5)	0.56146 (18)	0.84420 (10)	0.0319 (5)
H4	−0.2360	0.5175	0.8666	0.038*
C5	0.0350 (5)	0.51759 (17)	0.78915 (10)	0.0283 (5)
H5	−0.0128	0.4428	0.7738	0.034*
C6	0.2375 (5)	0.58518 (16)	0.75632 (10)	0.0236 (4)
C7	0.3987 (4)	0.55027 (18)	0.69814 (10)	0.0246 (4)
C8	0.7810 (5)	0.65258 (17)	0.62952 (10)	0.0248 (5)
C9	0.9960 (4)	0.56000 (18)	0.53842 (10)	0.0293 (5)
H9	1.1790	0.5981	0.5529	0.035*
C10	0.8682 (6)	0.62614 (19)	0.48198 (11)	0.0400 (6)
H10A	0.6858	0.5902	0.4687	0.048*
H10B	1.0041	0.6254	0.4453	0.048*
H10C	0.8318	0.7058	0.4954	0.048*
C11	1.0554 (6)	0.43512 (19)	0.52321 (12)	0.0432 (6)
H11A	1.1449	0.3982	0.5611	0.052*
H11B	1.1866	0.4299	0.4858	0.052*
H11C	0.8731	0.3961	0.5128	0.052*

	U11	U22	U33	U12	U13	U23
S1	0.0236 (2)	0.0281 (3)	0.0277 (2)	−0.0018 (2)	0.0024 (2)	−0.0002 (2)
O1	0.0339 (9)	0.0294 (8)	0.0386 (9)	−0.0041 (7)	0.0053 (8)	−0.0039 (7)
O2	0.0272 (8)	0.0338 (8)	0.0256 (8)	−0.0021 (7)	0.0072 (6)	−0.0037 (7)
O3	0.0312 (8)	0.0314 (8)	0.0284 (7)	−0.0096 (8)	0.0033 (7)	−0.0001 (6)
N1	0.0192 (8)	0.0240 (8)	0.0261 (9)	−0.0014 (8)	0.0021 (8)	−0.0011 (7)
C1	0.0184 (10)	0.0304 (11)	0.0286 (11)	0.0032 (8)	−0.0010 (9)	0.0056 (9)
C2	0.0284 (11)	0.0292 (11)	0.0277 (10)	−0.0002 (10)	0.0001 (9)	−0.0004 (9)
C3	0.0330 (14)	0.0401 (13)	0.0267 (11)	0.0055 (10)	0.0060 (9)	0.0043 (9)
C4	0.0271 (12)	0.0346 (12)	0.0341 (12)	0.0014 (11)	0.0050 (10)	0.0105 (10)
C5	0.0234 (11)	0.0239 (11)	0.0376 (12)	0.0004 (9)	−0.0024 (10)	0.0040 (9)
C6	0.0181 (10)	0.0255 (11)	0.0273 (11)	0.0031 (8)	−0.0042 (8)	0.0048 (8)
C7	0.0172 (10)	0.0290 (11)	0.0275 (10)	−0.0003 (9)	−0.0023 (9)	0.0047 (8)
C8	0.0218 (11)	0.0313 (12)	0.0215 (10)	0.0023 (9)	−0.0029 (9)	0.0028 (9)
C9	0.0262 (13)	0.0373 (12)	0.0244 (10)	−0.0021 (10)	0.0055 (9)	−0.0009 (9)
C10	0.0405 (16)	0.0507 (14)	0.0289 (12)	−0.0036 (12)	−0.0017 (11)	0.0002 (11)
C11	0.0464 (15)	0.0454 (13)	0.0377 (13)	0.0011 (14)	0.0115 (13)	−0.0039 (11)

S1—N1	1.7349 (17)	C4—C5	1.375 (3)
S1—C1	1.747 (2)	C4—H4	0.9500
O1—C7	1.212 (2)	C5—C6	1.395 (3)
O2—C8	1.329 (2)	C5—H5	0.9500
O2—C9	1.472 (2)	C6—C7	1.464 (3)
O3—C8	1.202 (2)	C9—C11	1.509 (3)
N1—C8	1.399 (3)	C9—C10	1.510 (3)
N1—C7	1.418 (3)	C9—H9	1.0000
C1—C6	1.392 (3)	C10—H10A	0.9800
C1—C2	1.393 (3)	C10—H10B	0.9800
C2—C3	1.379 (3)	C10—H10C	0.9800
C2—H2	0.9500	C11—H11A	0.9800
C3—C4	1.401 (3)	C11—H11B	0.9800
C3—H3	0.9500	C11—H11C	0.9800
N1—S1—C1	89.97 (9)	O1—C7—C6	127.63 (19)
C8—O2—C9	115.85 (16)	N1—C7—C6	107.53 (17)
C8—N1—C7	130.00 (17)	O3—C8—O2	127.0 (2)
C8—N1—S1	113.89 (13)	O3—C8—N1	121.00 (19)
C7—N1—S1	115.74 (14)	O2—C8—N1	112.00 (17)
C6—C1—C2	121.1 (2)	O2—C9—C11	105.33 (17)
C6—C1—S1	112.58 (15)	O2—C9—C10	109.20 (17)
C2—C1—S1	126.31 (17)	C11—C9—C10	113.71 (19)
C3—C2—C1	117.7 (2)	O2—C9—H9	109.5
C3—C2—H2	121.1	C11—C9—H9	109.5
C1—C2—H2	121.1	C10—C9—H9	109.5
C2—C3—C4	121.6 (2)	C9—C10—H10A	109.5
C2—C3—H3	119.2	C9—C10—H10B	109.5
C4—C3—H3	119.2	H10A—C10—H10B	109.5
C5—C4—C3	120.5 (2)	C9—C10—H10C	109.5
C5—C4—H4	119.8	H10A—C10—H10C	109.5
C3—C4—H4	119.8	H10B—C10—H10C	109.5
C4—C5—C6	118.6 (2)	C9—C11—H11A	109.5
C4—C5—H5	120.7	C9—C11—H11B	109.5
C6—C5—H5	120.7	H11A—C11—H11B	109.5
C1—C6—C5	120.5 (2)	C9—C11—H11C	109.5
C1—C6—C7	114.09 (18)	H11A—C11—H11C	109.5
C5—C6—C7	125.36 (18)	H11B—C11—H11C	109.5
O1—C7—N1	124.83 (19)
C1—S1—N1—C8	−175.20 (15)	S1—N1—C7—O1	−175.99 (17)
C1—S1—N1—C7	−1.47 (16)	C8—N1—C7—C6	175.40 (19)
N1—S1—C1—C6	−0.54 (15)	S1—N1—C7—C6	2.9 (2)
N1—S1—C1—C2	178.93 (19)	C1—C6—C7—O1	175.6 (2)
C6—C1—C2—C3	−1.3 (3)	C5—C6—C7—O1	−2.9 (3)
S1—C1—C2—C3	179.25 (17)	C1—C6—C7—N1	−3.3 (2)
C1—C2—C3—C4	−0.2 (3)	C5—C6—C7—N1	178.28 (19)
C2—C3—C4—C5	1.6 (3)	C9—O2—C8—O3	−0.8 (3)
C3—C4—C5—C6	−1.6 (3)	C9—O2—C8—N1	179.12 (16)
C2—C1—C6—C5	1.4 (3)	C7—N1—C8—O3	−173.8 (2)
S1—C1—C6—C5	−179.12 (16)	S1—N1—C8—O3	−1.2 (3)
C2—C1—C6—C7	−177.15 (18)	C7—N1—C8—O2	6.3 (3)
S1—C1—C6—C7	2.3 (2)	S1—N1—C8—O2	178.90 (13)
C4—C5—C6—C1	0.1 (3)	C8—O2—C9—C11	156.63 (18)
C4—C5—C6—C7	178.46 (19)	C8—O2—C9—C10	−80.9 (2)
C8—N1—C7—O1	−3.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1i	0.95	2.47	3.225 (3)	137.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.95	2.47	3.225 (3)	137

Symmetry code: (i) .