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

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

doi:10.1107/S1600536811028613

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2237

doi:10.1107/S1600536811028613

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Propyl 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: yangjxmail@sohu.com, linqianggroup@163.com

(Received 21 June 2011; accepted 16 July 2011; online 2 August 2011)

The title compound, C₁₁H₁₁NO₃S, was synthesized by the reaction of benzo[d]isothiazol-3(2H)-one with propyl carbonochloridate 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 intermolecular 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_r = 237.27
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.039
wR(F²) = 0.099
S = 1.00
2766 reflections
146 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.25 e Å⁻³

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) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

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/S1600536811028613/fl2349sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811028613/fl2349Isup3.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, (I), 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 0.0226 (14) A ° for the N atom, and the C8—O2—C9—C10 torsion angle is 85.16 (18)°. Weak intermolecular C—H···O hydrogen bonding occurs in the crystal structure (Table 1, Fig. 22))..

Related literature top

For background to the sythesis of benzisothiazolone 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 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 propyl carbonochloridate (1.22 g, 0.01 mol) in toluol (20 ml) under stirring on an ice-water bath. The reaction mixture was stirred at room temperature for 4.5 h to afford the title compound (1.55 g, yield 65.5%). 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 30% probability displacement ellipsoids and the atomnumbering scheme.
	Fig. 2. The crystal packing of the title compound, showing a hydrogen-bonded (dashed lines) molecular chain.

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

Crystal data top

C₁₁H₁₁NO₃S	F(000) = 496
M_r = 237.27	D_x = 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

Data collection top

Rigaku AFC10/Saturn724+ diffractometer	2766 independent reflections
Radiation source: Rotating Anode	2224 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
Detector resolution: 28.5714 pixels mm^-1	θ_max = 29.1°, θ_min = 3.2°
phi and ω scans	h = −20→22
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −6→6
T_min = 0.904, T_max = 0.943	l = −16→17
8491 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0506P)² + 0.316P] where P = (F_o² + 2F_c²)/3
2766 reflections	(Δ/σ)_max < 0.001
146 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₁H₁₁NO₃S	V = 1063.7 (8) Å³
M_r = 237.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.235 (7) Å	µ = 0.29 mm⁻¹
b = 5.123 (2) Å	T = 153 K
c = 12.791 (6) Å	0.35 × 0.25 × 0.20 mm
β = 90.720 (7)°

Data collection top

Rigaku AFC10/Saturn724+ diffractometer	2766 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2224 reflections with I > 2σ(I)
T_min = 0.904, T_max = 0.943	R_int = 0.031
8491 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 1.00	Δρ_max = 0.35 e Å⁻³
2766 reflections	Δρ_min = −0.25 e Å⁻³
146 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	0.25453 (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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₁NO₃S
M_r	237.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	153
a, b, c (Å)	16.235 (7), 5.123 (2), 12.791 (6)
β (°)	90.720 (7)
V (Å³)	1063.7 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.35 × 0.25 × 0.20

Data collection
Diffractometer	Rigaku AFC10/Saturn724+ diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.904, 0.943
No. of measured, independent and observed [I > 2σ(I)] reflections	8491, 2766, 2224
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.684

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.099, 1.00
No. of reflections	2766
No. of parameters	146
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.25

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

Hydrogen-bond geometry (Å, º) top

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) x, −y+3/2, z+1/2.

Acknowledgements

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

References

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