Ethyl 3-oxo-2,3-dihydro-1,2-benzothia­zole-2-carboxyl­ate

Wang, X.; Yang, J.; You, C.; Lin, Q.

doi:10.1107/S1600536811029199

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2238

doi:10.1107/S1600536811029199

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Ethyl 3-oxo-2,3-dihydro-1,2-benzothiazole-2-carboxylate

Xiang-hui Wang,^a Jian-xin Yang,^b Cheng-hang You ^b and Qiang Lin ^c,^d ^*

^aInstitute of Environmental Science and Engineering, Kunming University of Science and Technology, Kunming 650093, People's Republic of China, ^bHainan University Materials and Chemical Engineering, Haikou 570228, People's Republic of China, ^cHainan Provincial Fine Chemical Engineering Center, Hainan University, Haikou 570228, People's Republic of China, and ^dCollege of Chemistry and Chemical Engineering, Hainan Normal University, Haikou 571100, People's Republic of China
^*Correspondence e-mail: linqiang@hainu.edu.cn

(Received 25 May 2011; accepted 19 July 2011; online 2 August 2011)

The title compound, C₁₀H₉NO₃S, was synthesized by the reaction of benzo[d]isothiazol-3(2H)-one with ethyl carbonochloridate in toluol. The benzisothiazolone 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_r = 223.24
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.038
wR(F²) = 0.101
S = 1.00
2570 reflections
137 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811029199/kj2180sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811029199/kj2180Isup3.cml

checkCIF report

Comment top

1,2-Benzisothiazol-3(2H)-ones are a class of compounds with a wide spectrum of biological activities (Davis, 1972; Elgazwy & Abdel-Sattar, 2003). 1, 2-Benzisothiazolone derivatives have been reported to possess high antibacterial and antifungal activity (Taubert et al., 2002). In view of the importance of the 1,2-benzisothiazol-3(2H)-ones, the title compound was synthesized and characterized by X-ray diffraction.

The molecular structure of the title compound is shown in Fig. 1. In the molecule, the benzisothiazolone ring system is approximately planar with a maximum deviation from the mean plane of 0.020 (1) A ° for the N atom, and the C8—O2—C9—C10 torsion angle is -85.9 (2)°.

Related literature top

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 top

A toluol solution (20 ml) containing benzo[d]isothiazol-3(2H)-one (1.51 g, 0.01 mol) was added dropwise to a solution of ethyl carbonochloridate (1.08 g, 0.01 mol) in toluol (20 ml) under stirring on an ice-water bath. The reaction mixture was stirred at room temperature for 3.5 h to afford the title compound (1.65 g, yield 72%).. Single crystals suitable for X-ray measurements were obtained by recrystallization of the title compound from cyclohexane at room temperature.

Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); 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 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

Fig. 1. Title molecule showing the 50% probability displacement ellipsoids and the atom-numbering scheme.

Ethyl 3-oxo-2,3-dihydro-1,2-benzothiazole-2-carboxylate top

Crystal data top

C₁₀H₉NO₃S	F(000) = 464
M_r = 223.24	D_x = 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

Data collection top

Rigaku AFC10/Saturn724+ diffractometer	2570 independent reflections
Radiation source: Rotating Anode	2219 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 28.5714 pixels mm^-1	θ_max = 29.1°, θ_min = 3.2°
phi and ω scans	h = −21→23
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −6→6
T_min = 0.887, T_max = 0.907	l = −13→17
8002 measured reflections

Refinement top

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(F_o²) + (0.0596P)² + 0.216P] where P = (F_o² + 2F_c²)/3
2570 reflections	(Δ/σ)_max < 0.001
137 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₀H₉NO₃S	V = 979.0 (5) Å³
M_r = 223.24	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.904 (5) Å	µ = 0.32 mm⁻¹
b = 4.8912 (13) Å	T = 153 K
c = 12.676 (4) Å	0.39 × 0.33 × 0.32 mm
β = 110.929 (4)°

Data collection top

Rigaku AFC10/Saturn724+ diffractometer	2570 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2219 reflections with I > 2σ(I)
T_min = 0.887, T_max = 0.907	R_int = 0.027
8002 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.00	Δρ_max = 0.33 e Å⁻³
2570 reflections	Δρ_min = −0.23 e Å⁻³
137 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₀H₉NO₃S
M_r	223.24
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	153
a, b, c (Å)	16.904 (5), 4.8912 (13), 12.676 (4)
β (°)	110.929 (4)
V (Å³)	979.0 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.39 × 0.33 × 0.32

Data collection
Diffractometer	Rigaku AFC10/Saturn724+ diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.887, 0.907
No. of measured, independent and observed [I > 2σ(I)] reflections	8002, 2570, 2219
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.685

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.101, 1.00
No. of reflections	2570
No. of parameters	137
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.23

Computer programs: CrystalClear (Rigaku, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

Acknowledgements

The authors are grateful to the National Natural Science Foundation of China (No. 20962007) and the Creative Talents Plan of the Hainan University 211 Project.

References

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