2-(3-Methyl-but-2-en-1-yl)-1,2-benziso-thia-zol-3(2H)-one 1,1-dioxide.

In the title compound, C(12)H(13)NO(3)S, a saccharin derivative, the dihedral angle between the aromatic and isothia-zole rings is 2.91 (12)°. The planar 3,3-dimethyl-allyl group [maximum deviation = 0.0086 (16) Å] is oriented at dihedral angles of 71.86 (7) and 74.35 (7)° with respect to the aromatic and isothia-zole rings, respectively. In the crystal structure, weak inter-molecular C-H⋯O inter-actions link the mol-ecules into chains along the c axis. A weak C-H⋯π inter-action is also present.

Related literature

For the biological activity of saccharine derivatives, see: Primofiore et al. (1997 ▶). For related structures, see: Arshad et al. (2008 ▶); Kruszynski & Czestkowski (2001 ▶); Siddiqui et al. (2007 ▶); Yu et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C12H13NO3S

M = 251.29

Orthorhombic,

a = 9.4120 (5) Å

b = 19.4108 (11) Å

c = 6.5261 (4) Å

V = 1192.28 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 296 K

0.32 × 0.24 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.924, T max = 0.946

7340 measured reflections

2525 independent reflections

2304 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.083

S = 1.05

2525 reflections

156 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack (1983 ▶), 837 Friedel pairs

Flack parameter: 0.02 (8)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809012021/hk2656sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809012021/hk2656Isup2.hkl

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

C12H13NO3S	F(000) = 528
Mr = 251.29	Dx = 1.400 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2818 reflections
a = 9.4120 (5) Å	θ = 2.4–28.8°
b = 19.4108 (11) Å	µ = 0.27 mm−1
c = 6.5261 (4) Å	T = 296 K
V = 1192.28 (12) Å3	Rod, colorless
Z = 4	0.32 × 0.24 × 0.22 mm

Bruker Kappa APEXII CCD area-detector diffractometer	2525 independent reflections
Radiation source: fine-focus sealed tube	2304 reflections with I > 2σ(I)
graphite	Rint = 0.019
Detector resolution: 7.40 pixels mm-1	θmax = 28.8°, θmin = 2.4°
ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −26→26
Tmin = 0.924, Tmax = 0.946	l = −8→4
7340 measured reflections

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)] = 0.029	H-atom parameters constrained
wR(F2) = 0.083	w = 1/[σ2(Fo2) + (0.05P)2 + 0.1276P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2525 reflections	Δρmax = 0.28 e Å−3
156 parameters	Δρmin = −0.20 e Å−3
1 restraint	Absolute structure: Flack (1983), 837 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.02 (8)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.39059 (4)	0.43722 (2)	0.22028 (8)	0.0360 (1)
O1	0.47203 (15)	0.49780 (6)	0.1846 (2)	0.0527 (5)
O2	0.27683 (15)	0.44174 (7)	0.3626 (3)	0.0501 (5)
O3	0.34253 (18)	0.31180 (9)	−0.2062 (3)	0.0681 (6)
N1	0.32910 (16)	0.40665 (8)	−0.0015 (3)	0.0420 (5)
C1	0.47927 (19)	0.31849 (9)	0.1051 (3)	0.0430 (6)
C2	0.5491 (2)	0.25556 (10)	0.1123 (4)	0.0571 (7)
C3	0.6312 (2)	0.24143 (11)	0.2810 (5)	0.0643 (8)
C4	0.6463 (2)	0.28766 (11)	0.4407 (4)	0.0582 (8)
C5	0.5766 (2)	0.35100 (10)	0.4341 (4)	0.0474 (6)
C6	0.49541 (17)	0.36438 (8)	0.2640 (3)	0.0377 (5)
C7	0.37937 (19)	0.34237 (10)	−0.0545 (3)	0.0449 (6)
C8	0.2217 (2)	0.44531 (10)	−0.1171 (4)	0.0480 (6)
C9	0.0741 (2)	0.43125 (10)	−0.0398 (4)	0.0492 (7)
C10	−0.0319 (2)	0.40469 (9)	−0.1434 (4)	0.0476 (6)
C11	−0.0249 (3)	0.38285 (16)	−0.3615 (5)	0.0740 (10)
C12	−0.1738 (2)	0.39260 (14)	−0.0418 (5)	0.0718 (9)
H2	0.54056	0.22393	0.00600	0.0685*
H3	0.67821	0.19935	0.28810	0.0770*
H4	0.70306	0.27651	0.55253	0.0698*
H5	0.58470	0.38275	0.54021	0.0569*
H8A	0.22741	0.43275	−0.26069	0.0577*
H8B	0.24147	0.49421	−0.10592	0.0577*
H9	0.05601	0.44262	0.09618	0.0591*
H11A	0.06668	0.39430	−0.41673	0.1109*
H11B	−0.09740	0.40615	−0.43825	0.1109*
H11C	−0.03930	0.33398	−0.37040	0.1109*
H12A	−0.16911	0.40717	0.09857	0.1074*
H12B	−0.19663	0.34444	−0.04742	0.1074*
H12C	−0.24574	0.41849	−0.11203	0.1074*

	U11	U22	U33	U12	U13	U23
S1	0.0419 (2)	0.0326 (2)	0.0335 (2)	−0.0031 (1)	−0.0001 (2)	−0.0011 (2)
O1	0.0694 (8)	0.0384 (5)	0.0503 (10)	−0.0151 (5)	−0.0077 (8)	0.0034 (6)
O2	0.0521 (8)	0.0565 (8)	0.0418 (9)	0.0060 (5)	0.0063 (7)	−0.0040 (7)
O3	0.0786 (10)	0.0716 (10)	0.0540 (10)	−0.0120 (8)	−0.0050 (9)	−0.0261 (8)
N1	0.0438 (8)	0.0479 (8)	0.0343 (9)	−0.0056 (6)	−0.0020 (7)	−0.0034 (7)
C1	0.0392 (9)	0.0402 (8)	0.0495 (12)	−0.0075 (6)	0.0084 (8)	−0.0088 (8)
C2	0.0494 (11)	0.0444 (9)	0.0775 (17)	−0.0011 (8)	0.0111 (11)	−0.0155 (11)
C3	0.0501 (11)	0.0438 (9)	0.099 (2)	0.0072 (8)	0.0129 (12)	0.0057 (12)
C4	0.0462 (10)	0.0532 (11)	0.0752 (18)	0.0057 (8)	−0.0045 (11)	0.0117 (11)
C5	0.0475 (10)	0.0434 (9)	0.0513 (14)	−0.0043 (7)	−0.0044 (9)	0.0014 (9)
C6	0.0352 (7)	0.0336 (6)	0.0442 (12)	−0.0041 (5)	0.0046 (7)	−0.0010 (7)
C7	0.0436 (9)	0.0482 (9)	0.0430 (12)	−0.0128 (7)	0.0093 (8)	−0.0107 (9)
C8	0.0458 (10)	0.0566 (10)	0.0417 (12)	−0.0100 (8)	−0.0051 (9)	0.0101 (9)
C9	0.0486 (10)	0.0525 (10)	0.0466 (14)	0.0003 (8)	0.0024 (9)	0.0071 (9)
C10	0.0421 (10)	0.0398 (8)	0.0609 (14)	0.0017 (7)	−0.0025 (10)	0.0120 (9)
C11	0.0618 (14)	0.0871 (17)	0.0730 (19)	−0.0177 (12)	−0.0137 (13)	−0.0061 (15)
C12	0.0427 (11)	0.0706 (14)	0.102 (2)	0.0039 (9)	0.0049 (13)	0.0159 (14)

S1—O1	1.4229 (13)	C10—C11	1.487 (4)
S1—O2	1.4201 (17)	C10—C12	1.510 (3)
S1—N1	1.6679 (19)	C2—H2	0.9300
S1—C6	1.7475 (16)	C3—H3	0.9300
O3—C7	1.205 (3)	C4—H4	0.9300
N1—C7	1.379 (2)	C5—H5	0.9300
N1—C8	1.468 (3)	C8—H8A	0.9700
C1—C2	1.388 (3)	C8—H8B	0.9700
C1—C6	1.376 (3)	C9—H9	0.9300
C1—C7	1.478 (3)	C11—H11A	0.9600
C2—C3	1.373 (4)	C11—H11B	0.9600
C3—C4	1.383 (4)	C11—H11C	0.9600
C4—C5	1.394 (3)	C12—H12A	0.9600
C5—C6	1.373 (3)	C12—H12B	0.9600
C8—C9	1.503 (3)	C12—H12C	0.9600
C9—C10	1.311 (3)
O1···C5i	3.391 (2)	C11···H8A	2.6500
O1···C8ii	3.347 (2)	C12···H2viii	3.0500
O2···C9	3.253 (3)	H2···O3	2.8800
O2···C12iii	3.416 (3)	H2···C9vii	3.0400
O3···C5iv	3.308 (3)	H2···C10vii	2.7700
O1···H8B	2.8800	H2···C12vii	3.0500
O1···H5i	2.5600	H3···C1vii	3.0900
O2···H9	2.7100	H3···C7vii	3.0400
O2···H8Av	2.5100	H4···O3x	2.6700
O2···H12Ciii	2.7300	H5···O1ii	2.5600
O2···H11Av	2.6100	H8A···O2iv	2.5100
O3···H2	2.8800	H8A···O3	2.6100
O3···H8A	2.6100	H8A···C11	2.6500
O3···H4vi	2.6700	H8A···H11A	1.9700
C3···C7vii	3.591 (3)	H8B···O1	2.8800
C5···O1ii	3.391 (2)	H9···O2	2.7100
C5···O3v	3.308 (3)	H9···H12A	2.2300
C7···C3viii	3.591 (3)	H11A···O2iv	2.6100
C8···O1i	3.347 (2)	H11A···C8	2.6300
C9···O2	3.253 (3)	H11A···H8A	1.9700
C12···O2ix	3.416 (3)	H11B···H12C	2.5600
C1···H3viii	3.0900	H11C···H12B	2.5800
C7···H3viii	3.0400	H12A···H9	2.2300
C8···H11A	2.6300	H12B···H11C	2.5800
C9···H2viii	3.0400	H12C···H11B	2.5600
C10···H2viii	2.7700	H12C···O2ix	2.7300
O1—S1—O2	117.53 (8)	C1—C2—H2	121.00
O1—S1—N1	109.81 (8)	C3—C2—H2	121.00
O1—S1—C6	113.03 (8)	C2—C3—H3	119.00
O2—S1—N1	109.14 (9)	C4—C3—H3	119.00
O2—S1—C6	111.65 (9)	C3—C4—H4	120.00
N1—S1—C6	92.85 (8)	C5—C4—H4	120.00
S1—N1—C7	114.88 (14)	C4—C5—H5	122.00
S1—N1—C8	120.21 (14)	C6—C5—H5	121.00
C7—N1—C8	124.76 (18)	N1—C8—H8A	109.00
C2—C1—C6	119.48 (18)	N1—C8—H8B	109.00
C2—C1—C7	126.96 (18)	C9—C8—H8A	109.00
C6—C1—C7	113.49 (16)	C9—C8—H8B	109.00
C1—C2—C3	118.0 (2)	H8A—C8—H8B	108.00
C2—C3—C4	122.2 (2)	C8—C9—H9	117.00
C3—C4—C5	120.1 (2)	C10—C9—H9	116.00
C4—C5—C6	117.0 (2)	C10—C11—H11A	109.00
S1—C6—C1	109.79 (14)	C10—C11—H11B	109.00
S1—C6—C5	126.83 (15)	C10—C11—H11C	109.00
C1—C6—C5	123.28 (16)	H11A—C11—H11B	109.00
O3—C7—N1	123.57 (19)	H11A—C11—H11C	109.00
O3—C7—C1	127.42 (18)	H11B—C11—H11C	109.00
N1—C7—C1	108.99 (16)	C10—C12—H12A	109.00
N1—C8—C9	111.79 (19)	C10—C12—H12B	109.00
C8—C9—C10	127.0 (2)	C10—C12—H12C	109.00
C9—C10—C11	124.9 (2)	H12A—C12—H12B	109.00
C9—C10—C12	120.5 (2)	H12A—C12—H12C	110.00
C11—C10—C12	114.6 (2)	H12B—C12—H12C	109.00
O1—S1—N1—C7	116.40 (14)	C6—C1—C2—C3	0.6 (3)
O1—S1—N1—C8	−67.88 (16)	C7—C1—C2—C3	−176.00 (19)
O2—S1—N1—C7	−113.44 (14)	C2—C1—C6—S1	−177.54 (15)
O2—S1—N1—C8	62.29 (17)	C2—C1—C6—C5	−0.9 (3)
C6—S1—N1—C7	0.66 (15)	C7—C1—C6—S1	−0.5 (2)
C6—S1—N1—C8	176.38 (15)	C7—C1—C6—C5	176.15 (17)
O1—S1—C6—C1	−113.04 (13)	C2—C1—C7—O3	−0.8 (3)
O1—S1—C6—C5	70.51 (19)	C2—C1—C7—N1	177.73 (19)
O2—S1—C6—C1	111.81 (14)	C6—C1—C7—O3	−177.6 (2)
O2—S1—C6—C5	−64.64 (19)	C6—C1—C7—N1	0.9 (2)
N1—S1—C6—C1	−0.09 (14)	C1—C2—C3—C4	−0.3 (3)
N1—S1—C6—C5	−176.54 (17)	C2—C3—C4—C5	0.2 (3)
S1—N1—C7—O3	177.61 (17)	C3—C4—C5—C6	−0.4 (3)
S1—N1—C7—C1	−1.0 (2)	C4—C5—C6—S1	176.81 (15)
C8—N1—C7—O3	2.1 (3)	C4—C5—C6—C1	0.8 (3)
C8—N1—C7—C1	−176.49 (17)	N1—C8—C9—C10	−119.5 (2)
S1—N1—C8—C9	−83.37 (19)	C8—C9—C10—C11	0.3 (3)
C7—N1—C8—C9	91.9 (2)	C8—C9—C10—C12	178.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ii	0.93	2.56	3.391 (2)	149
C8—H8A···O2iv	0.97	2.51	3.436 (3)	160
C3—H3···Cg1vii	0.93	2.89	3.664 (2)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1i	0.93	2.56	3.391 (2)	149
C8—H8A⋯O2ii	0.97	2.51	3.436 (3)	160
C3—H3⋯Cg1iii	0.93	2.89	3.664 (2)	141

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the centroid of the C1–C6 ring.