organic compounds
2-n-Butyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxide
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
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
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Refinement
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Data collection: RAPID-AUTO (Rigaku, 2004); cell 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
10.1107/S1600536808007733/cv2391sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808007733/cv2391Isup2.hkl
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.
All H atoms were placed in idealized positions and constrained to ride on their parent atoms,with C—H distances of 0.95 (aromatic), 0.98 (CH3) and 0.99 Å (CH2),and with Uiso(H) values set at 1.5 Ueq(C)(for CH3) or 1.2 Ueq(C)(for CH2, aromatic CH).
Data collection: RAPID-AUTO (Rigaku, 2004); cell
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).Fig. 1. The molecular structure of (I) showing the atomic numbering and displacement ellipsoids drawn at the 40% probability level. |
C11H13NO3S | Z = 2 |
Mr = 239.28 | F(000) = 252 |
Triclinic, P1 | Dx = 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 |
Rigaku R-Axis Rapid IP area-detector diffractometer | 2061 independent reflections |
Radiation source: Rotating Anode | 1712 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
ω Oscillation scans | θmax = 25.0°, θmin = 3.0° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −8→8 |
Tmin = 0.924, Tmax = 0.953 | k = −9→9 |
4589 measured reflections | l = −13→13 |
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(Fo2) + (0.0554P)2 + 0.1349P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
2061 reflections | Δρmax = 0.23 e Å−3 |
146 parameters | Δρmin = −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) |
C11H13NO3S | γ = 109.75 (3)° |
Mr = 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)° |
Rigaku R-Axis Rapid IP area-detector diffractometer | 2061 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 1712 reflections with I > 2σ(I) |
Tmin = 0.924, Tmax = 0.953 | Rint = 0.017 |
4589 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.109 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.23 e Å−3 |
2061 reflections | Δρmin = −0.27 e Å−3 |
146 parameters |
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 | 0.42409 (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* |
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) |
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. |
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 |
Mr | 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) |
Tmin, Tmax | 0.924, 0.953 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4589, 2061, 1712 |
Rint | 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 |
Δρmax, Δρmin (e Å−3) | 0.23, −0.27 |
Computer programs: RAPID-AUTO (Rigaku, 2004), SHELXTL (Sheldrick, 2008).
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
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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.