Propyl 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 propyl carbono-chloridate in toluene. The benzoisothiazolone ring system is approximately planar with a maximum deviation from the mean plane of 0.0226 (14) Å for the N atom. Weak inter-molecular C-H⋯O hydrogen bonding occurs in the crystal structure.

Related literature

For background to the synthesis of benzoisothiazolone derivatives, see: Davis (1972 ▶); Elgazwy & Abdel-Sattar (2003 ▶). For their biological activity, see: Taubert et al. (2002 ▶). For related structures, see: Xu et al. (2005 ▶, 2006 ▶); Cavalca et al. (1969 ▶, 1970 ▶).

Experimental

Crystal data

C11H11NO3S

M = 237.27

Monoclinic,

a = 16.235 (7) Å

b = 5.123 (2) Å

c = 12.791 (6) Å

β = 90.720 (7)°

V = 1063.7 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 153 K

0.35 × 0.25 × 0.20 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.904, T max = 0.943

8491 measured reflections

2766 independent reflections

2224 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.099

S = 1.00

2766 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.25 e Å−3

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/S1600536811028613/fl2349sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028613/fl2349Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811028613/fl2349Isup3.cml

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

C11H11NO3S	F(000) = 496
Mr = 237.27	Dx = 1.482 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.235 (7) Å	Cell parameters from 3253 reflections
b = 5.123 (2) Å	θ = 3.0–29.1°
c = 12.791 (6) Å	µ = 0.29 mm−1
β = 90.720 (7)°	T = 153 K
V = 1063.7 (8) Å3	Block, pink
Z = 4	0.35 × 0.25 × 0.20 mm

Rigaku AFC10/Saturn724+ diffractometer	2766 independent reflections
Radiation source: Rotating Anode	2224 reflections with I > 2σ(I)
graphite	Rint = 0.031
Detector resolution: 28.5714 pixels mm-1	θmax = 29.1°, θmin = 3.2°
phi and ω scans	h = −20→22
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −6→6
Tmin = 0.904, Tmax = 0.943	l = −16→17
8491 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0506P)2 + 0.316P] where P = (Fo2 + 2Fc2)/3
2766 reflections	(Δ/σ)max < 0.001
146 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.25 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	0.25453 (2)	0.70918 (8)	0.71855 (3)	0.02263 (12)
O1	0.16642 (7)	0.7439 (2)	0.43840 (8)	0.0285 (3)
O2	0.28813 (7)	1.0985 (2)	0.46620 (9)	0.0289 (3)
O3	0.34796 (8)	1.1023 (3)	0.62778 (10)	0.0339 (3)
N1	0.24529 (8)	0.8149 (3)	0.59025 (10)	0.0210 (3)
C1	0.17595 (9)	0.4842 (3)	0.69666 (11)	0.0195 (3)
C2	0.14578 (10)	0.3037 (3)	0.76888 (12)	0.0227 (3)
H2	0.1671	0.2966	0.8383	0.027*
C3	0.08395 (10)	0.1360 (3)	0.73593 (13)	0.0256 (3)
H3	0.0628	0.0116	0.7837	0.031*
C4	0.05157 (10)	0.1449 (3)	0.63348 (13)	0.0258 (3)
H4	0.0088	0.0285	0.6130	0.031*
C5	0.08200 (9)	0.3230 (3)	0.56251 (12)	0.0226 (3)
H5	0.0608	0.3292	0.4930	0.027*
C6	0.14445 (9)	0.4939 (3)	0.59480 (11)	0.0189 (3)
C7	0.18296 (9)	0.6918 (3)	0.52901 (12)	0.0203 (3)
C8	0.29898 (9)	1.0187 (3)	0.56431 (12)	0.0231 (3)
C9	0.34321 (10)	1.3087 (3)	0.43295 (15)	0.0304 (4)
H9A	0.3533	1.4290	0.4923	0.036*
H9B	0.3163	1.4093	0.3760	0.036*
C10	0.42408 (10)	1.2039 (4)	0.39541 (14)	0.0295 (4)
H10A	0.4139	1.0737	0.3395	0.035*
H10B	0.4532	1.1151	0.4539	0.035*
C11	0.47784 (11)	1.4220 (4)	0.35365 (15)	0.0357 (4)
H11A	0.4520	1.4964	0.2907	0.043*
H11B	0.5322	1.3520	0.3364	0.043*
H11C	0.4840	1.5583	0.4070	0.043*

	U11	U22	U33	U12	U13	U23
S1	0.0270 (2)	0.0248 (2)	0.01593 (19)	−0.00360 (15)	−0.00484 (14)	0.00027 (15)
O1	0.0359 (7)	0.0350 (7)	0.0145 (5)	−0.0040 (5)	−0.0035 (5)	0.0026 (5)
O2	0.0261 (6)	0.0344 (7)	0.0262 (6)	−0.0044 (5)	−0.0009 (5)	0.0112 (5)
O3	0.0381 (7)	0.0357 (7)	0.0279 (6)	−0.0132 (6)	−0.0037 (5)	−0.0001 (5)
N1	0.0242 (6)	0.0236 (7)	0.0151 (6)	−0.0010 (5)	−0.0010 (5)	0.0009 (5)
C1	0.0213 (7)	0.0193 (7)	0.0178 (7)	0.0021 (5)	−0.0014 (5)	−0.0029 (6)
C2	0.0276 (8)	0.0237 (8)	0.0166 (7)	0.0024 (6)	−0.0013 (6)	0.0017 (6)
C3	0.0299 (8)	0.0225 (8)	0.0245 (8)	0.0000 (6)	0.0042 (6)	0.0010 (6)
C4	0.0248 (8)	0.0254 (8)	0.0270 (8)	−0.0027 (6)	0.0001 (6)	−0.0052 (7)
C5	0.0232 (7)	0.0258 (8)	0.0188 (7)	0.0026 (6)	−0.0025 (6)	−0.0051 (6)
C6	0.0218 (7)	0.0199 (7)	0.0150 (7)	0.0044 (6)	−0.0006 (5)	−0.0030 (6)
C7	0.0226 (7)	0.0227 (8)	0.0156 (7)	0.0024 (6)	−0.0006 (6)	−0.0030 (6)
C8	0.0242 (8)	0.0221 (8)	0.0228 (8)	0.0023 (6)	0.0018 (6)	−0.0005 (6)
C9	0.0274 (8)	0.0260 (9)	0.0378 (10)	0.0003 (7)	0.0037 (7)	0.0136 (7)
C10	0.0300 (9)	0.0278 (9)	0.0308 (9)	−0.0015 (7)	0.0049 (7)	−0.0023 (7)
C11	0.0334 (9)	0.0434 (11)	0.0305 (9)	−0.0095 (8)	0.0042 (7)	0.0008 (8)

S1—N1	1.7328 (15)	C4—C5	1.383 (2)
S1—C1	1.7393 (17)	C4—H4	0.9500
O1—C7	1.2162 (19)	C5—C6	1.398 (2)
O2—C8	1.329 (2)	C5—H5	0.9500
O2—C9	1.466 (2)	C6—C7	1.463 (2)
O3—C8	1.208 (2)	C9—C10	1.503 (2)
N1—C8	1.403 (2)	C9—H9A	0.9900
N1—C7	1.4195 (19)	C9—H9B	0.9900
C1—C6	1.395 (2)	C10—C11	1.519 (3)
C1—C2	1.400 (2)	C10—H10A	0.9900
C2—C3	1.383 (2)	C10—H10B	0.9900
C2—H2	0.9500	C11—H11A	0.9800
C3—C4	1.407 (2)	C11—H11B	0.9800
C3—H3	0.9500	C11—H11C	0.9800
N1—S1—C1	90.00 (7)	O1—C7—C6	127.56 (14)
C8—O2—C9	115.18 (13)	N1—C7—C6	107.29 (12)
C8—N1—C7	129.86 (13)	O3—C8—O2	127.15 (15)
C8—N1—S1	114.20 (10)	O3—C8—N1	120.72 (15)
C7—N1—S1	115.87 (11)	O2—C8—N1	112.13 (13)
C6—C1—C2	120.86 (14)	O2—C9—C10	111.65 (14)
C6—C1—S1	112.73 (12)	O2—C9—H9A	109.3
C2—C1—S1	126.40 (12)	C10—C9—H9A	109.3
C3—C2—C1	117.89 (14)	O2—C9—H9B	109.3
C3—C2—H2	121.1	C10—C9—H9B	109.3
C1—C2—H2	121.1	H9A—C9—H9B	108.0
C2—C3—C4	121.68 (15)	C9—C10—C11	110.97 (16)
C2—C3—H3	119.2	C9—C10—H10A	109.4
C4—C3—H3	119.2	C11—C10—H10A	109.4
C5—C4—C3	120.04 (15)	C9—C10—H10B	109.4
C5—C4—H4	120.0	C11—C10—H10B	109.4
C3—C4—H4	120.0	H10A—C10—H10B	108.0
C4—C5—C6	118.88 (15)	C10—C11—H11A	109.5
C4—C5—H5	120.6	C10—C11—H11B	109.5
C6—C5—H5	120.6	H11A—C11—H11B	109.5
C1—C6—C5	120.65 (14)	C10—C11—H11C	109.5
C1—C6—C7	114.07 (13)	H11A—C11—H11C	109.5
C5—C6—C7	125.28 (14)	H11B—C11—H11C	109.5
O1—C7—N1	125.15 (15)
C1—S1—N1—C8	178.88 (12)	S1—N1—C7—O1	178.47 (13)
C1—S1—N1—C7	1.45 (12)	C8—N1—C7—C6	−179.01 (14)
N1—S1—C1—C6	−0.32 (12)	S1—N1—C7—C6	−2.07 (16)
N1—S1—C1—C2	178.34 (14)	C1—C6—C7—O1	−178.77 (16)
C6—C1—C2—C3	0.0 (2)	C5—C6—C7—O1	1.8 (3)
S1—C1—C2—C3	−178.55 (12)	C1—C6—C7—N1	1.79 (18)
C1—C2—C3—C4	−0.3 (2)	C5—C6—C7—N1	−177.67 (14)
C2—C3—C4—C5	0.6 (2)	C9—O2—C8—O3	0.9 (2)
C3—C4—C5—C6	−0.6 (2)	C9—O2—C8—N1	−179.00 (13)
C2—C1—C6—C5	−0.1 (2)	C7—N1—C8—O3	178.88 (15)
S1—C1—C6—C5	178.67 (12)	S1—N1—C8—O3	1.9 (2)
C2—C1—C6—C7	−179.57 (14)	C7—N1—C8—O2	−1.2 (2)
S1—C1—C6—C7	−0.82 (17)	S1—N1—C8—O2	−178.19 (10)
C4—C5—C6—C1	0.4 (2)	C8—O2—C9—C10	85.16 (18)
C4—C5—C6—C7	179.80 (14)	O2—C9—C10—C11	175.72 (15)
C8—N1—C7—O1	1.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2i	0.95	2.60	3.437 (3)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2i	0.95	2.60	3.437 (3)	148

Symmetry code: (i) .