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

The title compound, C(10)H(9)NO(3)S, was synthesized by the reaction of benzo[d]isothia-zol-3(2H)-one with ethyl carbonochloridate in toluol. The benzisothia-zolone ring system is approximately planar, with a maximum deviation from the mean plane of 0.020 (1) Å for the N atom.

Related literature

For background to the sythesis of benzisothia­zolone derivatives, see: Davis (1972 ▶); Elgazwy & Abdel-Sattar (2003 ▶). For details of 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

C10H9NO3S

M = 223.24

Monoclinic,

a = 16.904 (5) Å

b = 4.8912 (13) Å

c = 12.676 (4) Å

β = 110.929 (4)°

V = 979.0 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.32 mm−1

T = 153 K

0.39 × 0.33 × 0.32 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.887, T max = 0.907

8002 measured reflections

2570 independent reflections

2219 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.101

S = 1.00

2570 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.23 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/S1600536811029199/kj2180sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029199/kj2180Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811029199/kj2180Isup3.cml

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

C10H9NO3S	F(000) = 464
Mr = 223.24	Dx = 1.515 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.904 (5) Å	Cell parameters from 3063 reflections
b = 4.8912 (13) Å	θ = 3.2–29.1°
c = 12.676 (4) Å	µ = 0.32 mm−1
β = 110.929 (4)°	T = 153 K
V = 979.0 (5) Å3	Block, colourless
Z = 4	0.39 × 0.33 × 0.32 mm

Rigaku AFC10/Saturn724+ diffractometer	2570 independent reflections
Radiation source: Rotating Anode	2219 reflections with I > 2σ(I)
graphite	Rint = 0.027
Detector resolution: 28.5714 pixels mm-1	θmax = 29.1°, θmin = 3.2°
phi and ω scans	h = −21→23
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −6→6
Tmin = 0.887, Tmax = 0.907	l = −13→17
8002 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0596P)2 + 0.216P] where P = (Fo2 + 2Fc2)/3
2570 reflections	(Δ/σ)max < 0.001
137 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.23 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	0.27279 (2)	0.29920 (8)	0.34210 (3)	0.02398 (12)
O1	0.18146 (7)	0.2458 (2)	0.01861 (9)	0.0304 (3)
O2	0.31201 (7)	−0.1043 (2)	0.10660 (10)	0.0330 (3)
O3	0.37405 (7)	−0.0967 (2)	0.29680 (10)	0.0345 (3)
N1	0.26376 (8)	0.1848 (2)	0.20927 (10)	0.0221 (3)
C1	0.18919 (9)	0.5239 (3)	0.28158 (11)	0.0206 (3)
C2	0.15658 (10)	0.7092 (3)	0.33898 (12)	0.0248 (3)
H2	0.1792	0.7220	0.4190	0.030*
C3	0.09010 (10)	0.8740 (3)	0.27524 (13)	0.0272 (3)
H3	0.0672	1.0030	0.3125	0.033*
C4	0.05574 (10)	0.8556 (3)	0.15727 (13)	0.0275 (3)
H4	0.0095	0.9691	0.1158	0.033*
C5	0.08898 (9)	0.6725 (3)	0.10098 (12)	0.0238 (3)
H5	0.0666	0.6606	0.0209	0.029*
C6	0.15598 (9)	0.5061 (3)	0.16423 (11)	0.0203 (3)
C7	0.19790 (9)	0.3036 (3)	0.11718 (12)	0.0217 (3)
C8	0.32227 (9)	−0.0189 (3)	0.20969 (13)	0.0249 (3)
C9	0.37419 (11)	−0.3059 (4)	0.10007 (17)	0.0422 (5)
H9A	0.3489	−0.4204	0.0319	0.051*
H9B	0.3901	−0.4269	0.1670	0.051*
C10	0.45105 (12)	−0.1664 (5)	0.0952 (2)	0.0548 (6)
H10A	0.4349	−0.0427	0.0301	0.066*
H10B	0.4910	−0.3033	0.0876	0.066*
H10C	0.4778	−0.0613	0.1647	0.066*

	U11	U22	U33	U12	U13	U23
S1	0.0276 (2)	0.02520 (19)	0.01661 (18)	0.00118 (14)	0.00484 (13)	0.00023 (13)
O1	0.0399 (6)	0.0342 (6)	0.0176 (5)	0.0038 (5)	0.0110 (5)	−0.0003 (4)
O2	0.0273 (6)	0.0384 (6)	0.0333 (6)	0.0050 (5)	0.0110 (5)	−0.0109 (5)
O3	0.0350 (6)	0.0345 (6)	0.0318 (6)	0.0075 (5)	0.0092 (5)	0.0049 (5)
N1	0.0247 (6)	0.0243 (6)	0.0174 (6)	0.0004 (5)	0.0078 (5)	−0.0002 (4)
C1	0.0235 (6)	0.0188 (6)	0.0195 (7)	−0.0034 (5)	0.0078 (5)	0.0013 (5)
C2	0.0309 (7)	0.0252 (7)	0.0197 (7)	−0.0036 (6)	0.0109 (6)	−0.0024 (5)
C3	0.0321 (8)	0.0234 (7)	0.0312 (8)	−0.0002 (6)	0.0174 (6)	−0.0003 (6)
C4	0.0275 (7)	0.0267 (7)	0.0288 (8)	0.0027 (6)	0.0108 (6)	0.0064 (6)
C5	0.0253 (7)	0.0254 (7)	0.0198 (7)	−0.0026 (5)	0.0072 (5)	0.0034 (5)
C6	0.0236 (6)	0.0195 (6)	0.0189 (7)	−0.0049 (5)	0.0089 (5)	0.0006 (5)
C7	0.0254 (7)	0.0229 (6)	0.0188 (6)	−0.0023 (5)	0.0102 (5)	0.0019 (5)
C8	0.0233 (7)	0.0231 (7)	0.0299 (8)	−0.0022 (6)	0.0113 (6)	0.0001 (6)
C9	0.0322 (9)	0.0456 (10)	0.0462 (11)	0.0092 (8)	0.0109 (8)	−0.0155 (8)
C10	0.0375 (10)	0.0769 (16)	0.0567 (13)	0.0176 (10)	0.0249 (9)	0.0170 (11)

S1—N1	1.7286 (13)	C3—H3	0.9500
S1—C1	1.7374 (15)	C4—C5	1.383 (2)
O1—C7	1.2125 (18)	C4—H4	0.9500
O2—C8	1.3232 (19)	C5—C6	1.393 (2)
O2—C9	1.465 (2)	C5—H5	0.9500
O3—C8	1.1999 (18)	C6—C7	1.463 (2)
N1—C8	1.4025 (19)	C9—C10	1.488 (3)
N1—C7	1.4182 (18)	C9—H9A	0.9900
C1—C6	1.3924 (19)	C9—H9B	0.9900
C1—C2	1.393 (2)	C10—H10A	0.9800
C2—C3	1.384 (2)	C10—H10B	0.9800
C2—H2	0.9500	C10—H10C	0.9800
C3—C4	1.400 (2)
N1—S1—C1	89.99 (6)	C1—C6—C7	114.11 (12)
C8—O2—C9	115.15 (13)	C5—C6—C7	125.01 (13)
C8—N1—C7	129.73 (12)	O1—C7—N1	125.20 (14)
C8—N1—S1	114.18 (10)	O1—C7—C6	127.71 (13)
C7—N1—S1	116.07 (10)	N1—C7—C6	107.09 (12)
C6—C1—C2	120.98 (13)	O3—C8—O2	127.15 (14)
C6—C1—S1	112.72 (11)	O3—C8—N1	120.68 (14)
C2—C1—S1	126.30 (11)	O2—C8—N1	112.17 (12)
C3—C2—C1	117.65 (13)	O2—C9—C10	110.40 (16)
C3—C2—H2	121.2	O2—C9—H9A	109.6
C1—C2—H2	121.2	C10—C9—H9A	109.6
C2—C3—C4	121.76 (14)	O2—C9—H9B	109.6
C2—C3—H3	119.1	C10—C9—H9B	109.6
C4—C3—H3	119.1	H9A—C9—H9B	108.1
C5—C4—C3	120.16 (14)	C9—C10—H10A	109.5
C5—C4—H4	119.9	C9—C10—H10B	109.5
C3—C4—H4	119.9	H10A—C10—H10B	109.5
C4—C5—C6	118.56 (14)	C9—C10—H10C	109.5
C4—C5—H5	120.7	H10A—C10—H10C	109.5
C6—C5—H5	120.7	H10B—C10—H10C	109.5
C1—C6—C5	120.88 (13)
C1—S1—N1—C8	−179.94 (11)	C8—N1—C7—O1	−0.7 (2)
C1—S1—N1—C7	−1.47 (11)	S1—N1—C7—O1	−178.93 (12)
N1—S1—C1—C6	0.71 (11)	C8—N1—C7—C6	179.92 (13)
N1—S1—C1—C2	−178.46 (13)	S1—N1—C7—C6	1.74 (15)
C6—C1—C2—C3	0.1 (2)	C1—C6—C7—O1	179.53 (14)
S1—C1—C2—C3	179.22 (11)	C5—C6—C7—O1	−0.9 (2)
C1—C2—C3—C4	0.5 (2)	C1—C6—C7—N1	−1.16 (16)
C2—C3—C4—C5	−1.1 (2)	C5—C6—C7—N1	178.43 (13)
C3—C4—C5—C6	0.9 (2)	C9—O2—C8—O3	−3.4 (2)
C2—C1—C6—C5	−0.2 (2)	C9—O2—C8—N1	176.56 (13)
S1—C1—C6—C5	−179.46 (11)	C7—N1—C8—O3	−179.58 (14)
C2—C1—C6—C7	179.38 (13)	S1—N1—C8—O3	−1.37 (18)
S1—C1—C6—C7	0.15 (15)	C7—N1—C8—O2	0.5 (2)
C4—C5—C6—C1	−0.3 (2)	S1—N1—C8—O2	178.70 (10)
C4—C5—C6—C7	−179.85 (13)	C8—O2—C9—C10	−85.9 (2)