2-n-Butyl-1,2-benzisothia-zol-3(2H)-one 1,1-dioxide.

The crystal packing of the title compound, C(11)H(13)NO(3)S, exhibits weak inter-molecular C-H⋯O hydrogen bonding, which links mol-ecules related by translation along the b axis into chains, and π-π inter-actions [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 = 239.28

Triclinic,

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[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.109

S = 1.08

2061 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.27 e Å−3

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.

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

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

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

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	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)

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)

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

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) .