2-n-Butyl-1,2-benzisothia­zol-3(2H)-one 1,1-dioxide

Yu, G.-P.; Xu, Z.-J.; Xu, L.-Z.; Aisa, H.A.

doi:10.1107/S1600536808007733

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o805

doi:10.1107/S1600536808007733

Open

access

2-n-Butyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxide

Guan-Ping Yu,^a,^b Zhong-Jie Xu,^c Liang-Zhong Xu ^c and Haji Akber Aisa ^a ^*

^aXinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Science, Urumqi, 830011, People's Republic of China, ^bGraduate School of the Chinese Academy of Science, Beijing, 100039, People's Republic of China, and ^cCollege of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao, 266042, People's Republic of China
^*Correspondence e-mail: qknhs@yahoo.com.cn

(Received 2 March 2008; accepted 20 March 2008; online 4 April 2008)

The crystal packing of the title compound, C₁₁H₁₃NO₃S, exhibits weak intermolecular C—H⋯O hydrogen bonding, which links molecules related by translation along the b axis into chains, and π–π interactions [centroid–centroid distance of 3.778 (2) Å between benzene rings].

Related literature

For similar crystal structures, see: Feeder & Jones (1994 , 1996 ); Glidewell et al. (2000 ). For related literature, see: Xiong (2004 ); Rice & Pettit (1954 ).

Experimental

Crystal data

C₁₁H₁₃NO₃S
M_r = 239.28
Triclinic, $[P \overline 1]$
a = 7.3130 (15) Å
b = 7.7219 (15) Å
c = 11.416 (2) Å
α = 102.76 (3)°
β = 94.23 (3)°
γ = 109.75 (3)°
V = 584.0 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 153 (2) K
0.30 × 0.24 × 0.18 mm

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.924, T_max = 0.953
4589 measured reflections
2061 independent reflections
1712 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.109
S = 1.08
2061 reflections
146 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2B⋯O3ⁱⁱ	0.95	2.35	3.279 (2)	165
Symmetry code: (ii) x, y-1, z.

Data collection: RAPID-AUTO (Rigaku, 2004 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808007733/cv2391sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808007733/cv2391Isup2.hkl

checkCIF report

Comment top

The title compound, (I), also called THIAZONE, is a new skin penetration enhancer. The tests of penetration enhancing behaviors to berberine, ciclopirox olamino and cypermethrin show that penetration enhancing effect ofTHIAZONE is 2.99 times higher than that of AZONE. THIAZONE is widely applied in pharmaceutic industry, cosmetic and health care industry, agriculture and forest industry, and many others (Xiong, 2004). Herewith we report the crystal structure of (I).

In (I) (Fig. 1), all bond lengths and angles within the saccharin group are similar to those observed in the series of N-saccharin acids (Feeder & Jones, 1996), N-saccharin peracids (Feeder & Jones, 1994) and saccharin (Glidewell et al., 2000).

In the crystal, the relatively short distance between the centroids of benzene rings from neighbouring molecules (Table 1) suggests an existence of π···π interactions. The crystal packing exhibits also exhibits weak intermolecular C—H···O hydrogen bonds (Table 2), which link the molecules related by translation along b axis into chains.

Related literature top

For similar crystal structures, see: Feeder & Jones (1994, 1996); Glidewell et al. (2000). For related literature, see: Xiong (2004); Rice & Pettit (1954).

Experimental top

The title compound has been synthesized following the known procedure (Rice & Pettit, 1954). Saccharin sodium 2.65 g (0.011 mol) was dissolved in 20 ml of dried DMF. To the solution,1-butyl bromide 1.37 g (0.01 mol) was added. The mixture was stirred for half an hour at room temperature and then the mixture was heated with strring for 2 h at 100° C. The mixture was poured into water, and 2.50 g of the product were obtained (yield 95.7%). Single crystals suitable for X-ray measurement were obtained by recrystallization from dichloromethane at room temperature.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO (Rigaku, 2004); data reduction: RAPID-AUTO (Rigaku, 2004); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) showing the atomic numbering and displacement ellipsoids drawn at the 40% probability level.

2-n-Butyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxide top

Crystal data top

C₁₁H₁₃NO₃S	Z = 2
M_r = 239.28	F(000) = 252
Triclinic, P1	D_x = 1.361 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3130 (15) Å	Cell parameters from 1494 reflections
b = 7.7219 (15) Å	θ = 2.6–26.4°
c = 11.416 (2) Å	µ = 0.27 mm⁻¹
α = 102.76 (3)°	T = 153 K
β = 94.23 (3)°	Block, colourless
γ = 109.75 (3)°	0.30 × 0.24 × 0.18 mm
V = 584.0 (2) Å³

Data collection top

Rigaku R-Axis Rapid IP area-detector diffractometer	2061 independent reflections
Radiation source: Rotating Anode	1712 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
ω Oscillation scans	θ_max = 25.0°, θ_min = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −8→8
T_min = 0.924, T_max = 0.953	k = −9→9
4589 measured reflections	l = −13→13

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.109	w = 1/[σ²(F_o²) + (0.0554P)² + 0.1349P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.001
2061 reflections	Δρ_max = 0.23 e Å⁻³
146 parameters	Δρ_min = −0.27 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.129 (10)

Crystal data top

C₁₁H₁₃NO₃S	γ = 109.75 (3)°
M_r = 239.28	V = 584.0 (2) Å³
Triclinic, P1	Z = 2
a = 7.3130 (15) Å	Mo Kα radiation
b = 7.7219 (15) Å	µ = 0.27 mm⁻¹
c = 11.416 (2) Å	T = 153 K
α = 102.76 (3)°	0.30 × 0.24 × 0.18 mm
β = 94.23 (3)°

Data collection top

Rigaku R-Axis Rapid IP area-detector diffractometer	2061 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1712 reflections with I > 2σ(I)
T_min = 0.924, T_max = 0.953	R_int = 0.017
4589 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 1.08	Δρ_max = 0.23 e Å⁻³
2061 reflections	Δρ_min = −0.27 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	0.42409 (7)	0.81664 (7)	0.72568 (5)	0.0606 (2)
O1	0.3065 (2)	0.7267 (2)	0.80490 (15)	0.0795 (5)
O2	0.6279 (2)	0.8432 (2)	0.74251 (17)	0.0828 (5)
O3	0.3009 (2)	1.1828 (2)	0.60625 (15)	0.0757 (5)
N1	0.4016 (2)	1.0256 (2)	0.73053 (15)	0.0597 (4)
C1	0.3124 (3)	0.7195 (3)	0.57339 (18)	0.0521 (5)
C2	0.2711 (3)	0.5368 (3)	0.5017 (2)	0.0624 (5)
H2B	0.3056	0.4455	0.5327	0.075*
C3	0.1780 (3)	0.4928 (3)	0.3836 (2)	0.0685 (6)
H3A	0.1489	0.3691	0.3317	0.082*
C4	0.1262 (3)	0.6256 (3)	0.3393 (2)	0.0675 (6)
H4A	0.0605	0.5910	0.2580	0.081*
C5	0.1682 (3)	0.8068 (3)	0.41115 (19)	0.0603 (5)
H5A	0.1332	0.8977	0.3800	0.072*
C6	0.2625 (3)	0.8541 (3)	0.52964 (18)	0.0506 (4)
C7	0.3201 (3)	1.0391 (3)	0.62121 (19)	0.0555 (5)
C8	0.4943 (3)	1.1887 (3)	0.8376 (2)	0.0770 (7)
H8A	0.5302	1.3073	0.8103	0.092*
H8B	0.6178	1.1805	0.8731	0.092*
C9	0.3700 (4)	1.2038 (4)	0.9357 (2)	0.0828 (7)
H9A	0.3341	1.0851	0.9628	0.099*
H9B	0.4509	1.3101	1.0061	0.099*
C10	0.1870 (4)	1.2355 (4)	0.9009 (3)	0.0896 (8)
H10A	0.0964	1.1205	0.8392	0.108*
H10B	0.2196	1.3434	0.8629	0.108*
C11	0.0818 (5)	1.2781 (4)	1.0081 (3)	0.1019 (9)
H11A	−0.0369	1.2987	0.9794	0.153*
H11B	0.1698	1.3930	1.0690	0.153*
H11C	0.0449	1.1701	1.0446	0.153*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0564 (3)	0.0666 (4)	0.0714 (4)	0.0257 (3)	0.0102 (2)	0.0377 (3)
O1	0.0874 (11)	0.0866 (11)	0.0758 (10)	0.0256 (9)	0.0202 (8)	0.0509 (9)
O2	0.0591 (9)	0.0988 (12)	0.1038 (12)	0.0374 (8)	0.0022 (8)	0.0426 (10)
O3	0.0906 (11)	0.0589 (9)	0.0971 (12)	0.0388 (8)	0.0214 (9)	0.0387 (8)
N1	0.0593 (10)	0.0567 (10)	0.0665 (10)	0.0210 (8)	0.0087 (8)	0.0232 (8)
C1	0.0454 (10)	0.0560 (11)	0.0688 (12)	0.0231 (8)	0.0181 (8)	0.0338 (9)
C2	0.0565 (11)	0.0555 (11)	0.0927 (16)	0.0284 (9)	0.0287 (11)	0.0358 (11)
C3	0.0599 (13)	0.0654 (13)	0.0783 (15)	0.0195 (10)	0.0227 (11)	0.0166 (11)
C4	0.0589 (12)	0.0796 (15)	0.0638 (13)	0.0218 (11)	0.0142 (10)	0.0228 (11)
C5	0.0533 (11)	0.0721 (13)	0.0695 (13)	0.0275 (10)	0.0156 (9)	0.0368 (11)
C6	0.0439 (9)	0.0530 (10)	0.0669 (11)	0.0209 (8)	0.0164 (8)	0.0319 (9)
C7	0.0512 (11)	0.0544 (11)	0.0736 (13)	0.0235 (9)	0.0196 (9)	0.0322 (9)
C8	0.0637 (14)	0.0725 (15)	0.0824 (16)	0.0144 (11)	0.0050 (12)	0.0142 (12)
C9	0.0883 (17)	0.0833 (16)	0.0685 (14)	0.0276 (14)	−0.0029 (12)	0.0141 (12)
C10	0.0831 (17)	0.0983 (19)	0.0853 (17)	0.0308 (15)	0.0070 (14)	0.0255 (14)
C11	0.104 (2)	0.095 (2)	0.107 (2)	0.0410 (17)	0.0282 (18)	0.0150 (16)

Geometric parameters (Å, º) top

S1—O1	1.4243 (15)	C5—C6	1.383 (3)
S1—O2	1.4265 (16)	C5—H5A	0.9500
S1—N1	1.6661 (17)	C6—C7	1.476 (3)
S1—C1	1.747 (2)	C8—C9	1.503 (3)
O3—C7	1.210 (2)	C8—H8A	0.9900
N1—C7	1.383 (3)	C8—H8B	0.9900
N1—C8	1.470 (3)	C9—C10	1.481 (4)
C1—C2	1.384 (3)	C9—H9A	0.9900
C1—C6	1.386 (2)	C9—H9B	0.9900
C2—C3	1.381 (3)	C10—C11	1.527 (4)
C2—H2B	0.9500	C10—H10A	0.9900
C3—C4	1.383 (3)	C10—H10B	0.9900
C3—H3A	0.9500	C11—H11A	0.9800
C4—C5	1.375 (3)	C11—H11B	0.9800
C4—H4A	0.9500	C11—H11C	0.9800

Cg1···Cg1ⁱ	3.778 (2)

O1—S1—O2	117.55 (10)	O3—C7—N1	123.7 (2)
O1—S1—N1	109.67 (10)	O3—C7—C6	126.81 (19)
O2—S1—N1	109.17 (10)	N1—C7—C6	109.45 (16)
O1—S1—C1	111.98 (10)	N1—C8—C9	115.25 (19)
O2—S1—C1	112.60 (10)	N1—C8—H8A	108.5
N1—S1—C1	93.09 (9)	C9—C8—H8A	108.5
C7—N1—C8	123.88 (18)	N1—C8—H8B	108.5
C7—N1—S1	114.58 (14)	C9—C8—H8B	108.5
C8—N1—S1	120.69 (15)	H8A—C8—H8B	107.5
C2—C1—C6	121.99 (19)	C10—C9—C8	115.6 (2)
C2—C1—S1	128.18 (16)	C10—C9—H9A	108.4
C6—C1—S1	109.81 (15)	C8—C9—H9A	108.4
C3—C2—C1	117.30 (19)	C10—C9—H9B	108.4
C3—C2—H2B	121.3	C8—C9—H9B	108.4
C1—C2—H2B	121.3	H9A—C9—H9B	107.4
C2—C3—C4	121.1 (2)	C9—C10—C11	113.4 (2)
C2—C3—H3A	119.4	C9—C10—H10A	108.9
C4—C3—H3A	119.4	C11—C10—H10A	108.9
C5—C4—C3	121.1 (2)	C9—C10—H10B	108.9
C5—C4—H4A	119.4	C11—C10—H10B	108.9
C3—C4—H4A	119.4	H10A—C10—H10B	107.7
C4—C5—C6	118.64 (19)	C10—C11—H11A	109.5
C4—C5—H5A	120.7	C10—C11—H11B	109.5
C6—C5—H5A	120.7	H11A—C11—H11B	109.5
C5—C6—C1	119.82 (19)	C10—C11—H11C	109.5
C5—C6—C7	127.23 (17)	H11A—C11—H11C	109.5
C1—C6—C7	112.96 (17)	H11B—C11—H11C	109.5

O1—S1—N1—C7	−117.32 (15)	C4—C5—C6—C7	−179.82 (17)
O2—S1—N1—C7	112.58 (16)	C2—C1—C6—C5	0.2 (3)
C1—S1—N1—C7	−2.65 (15)	S1—C1—C6—C5	−178.69 (14)
O1—S1—N1—C8	72.84 (17)	C2—C1—C6—C7	179.99 (16)
O2—S1—N1—C8	−57.26 (18)	S1—C1—C6—C7	1.14 (19)
C1—S1—N1—C8	−172.49 (16)	C8—N1—C7—O3	−7.0 (3)
O1—S1—C1—C2	−65.33 (19)	S1—N1—C7—O3	−176.51 (15)
O2—S1—C1—C2	69.76 (19)	C8—N1—C7—C6	173.10 (17)
N1—S1—C1—C2	−177.99 (17)	S1—N1—C7—C6	3.63 (19)
O1—S1—C1—C6	113.43 (14)	C5—C6—C7—O3	−3.0 (3)
O2—S1—C1—C6	−111.48 (14)	C1—C6—C7—O3	177.15 (18)
N1—S1—C1—C6	0.77 (14)	C5—C6—C7—N1	176.82 (17)
C6—C1—C2—C3	0.2 (3)	C1—C6—C7—N1	−3.0 (2)
S1—C1—C2—C3	178.82 (14)	C7—N1—C8—C9	101.9 (2)
C1—C2—C3—C4	−0.7 (3)	S1—N1—C8—C9	−89.2 (2)
C2—C3—C4—C5	0.9 (3)	N1—C8—C9—C10	−63.7 (3)
C3—C4—C5—C6	−0.5 (3)	C8—C9—C10—C11	−171.7 (2)
C4—C5—C6—C1	0.0 (3)

Symmetry code: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O3ⁱⁱ	0.95	2.35	3.279 (2)	165

Symmetry code: (ii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₃NO₃S
M_r	239.28
Crystal system, space group	Triclinic, P1
Temperature (K)	153
a, b, c (Å)	7.3130 (15), 7.7219 (15), 11.416 (2)
α, β, γ (°)	102.76 (3), 94.23 (3), 109.75 (3)
V (Å³)	584.0 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.30 × 0.24 × 0.18

Data collection
Diffractometer	Rigaku R-Axis Rapid IP area-detector diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.924, 0.953
No. of measured, independent and observed [I > 2σ(I)] reflections	4589, 2061, 1712
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.109, 1.08
No. of reflections	2061
No. of parameters	146
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.27

Computer programs: RAPID-AUTO (Rigaku, 2004), SHELXTL (Sheldrick, 2008).

Selected interatomic distances (Å) top

Cg1···Cg1ⁱ

3.778 (2)

Symmetry code: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O3ⁱⁱ	0.95	2.35	3.279 (2)	164.9

Symmetry code: (ii) x, y−1, z.

Acknowledgements

We thank the Xinjiang Laboratory of Plant Resources and Natural Products Chemistry.

References

Feeder, N. & Jones, W. (1994). Acta Cryst. C50, 1118–1122. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Feeder, N. & Jones, W. (1996). Acta Cryst. C52, 2323–2326. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Glidewell, C., Low, J. N. & Wardell, J. L. (2000). Acta Cryst. C56, 1462–1464. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rice, H. L. & Pettit, G. R. (1954). J. Am. Chem. Soc. 76, 302–303. CrossRef CAS Web of Science Google Scholar
Rigaku (2004). RAPID-AUTO. Rigaku Corporation, Takyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xiong, L. Z. (2004). Jingxi Huaxuepin, 21, 9–11. Google Scholar