(Z)-3-Chloro-methyl-idene-5,6-dimeth-oxy-2-methyl-2,3-dihydro-1,2-benzothia-zole 1,1-dioxide.

The title compound, C(11)H(12)ClNO(4)S, adopts a Z configuration about the C=C double bond. The benzisothia-zole system is essentially planar [maximum deviation of 0.235 (2) Å for the S atom]. In the crystal, the mol-ecules stack parallel to each other in the b-axis direction, with inter-planar spacings for the benzene and thia-zole rings ranging from 3.402 (2) to 3.702 (2) Å.

Related literature

3-Substituted 1,2-benzisothia­zole-1,1-dioxides are an important class of heterocycles with a broad range of biological activity, see: Feit et al. (1973 ▶); Shutske et al. (1983 ▶); Bachman et al. (1978 ▶); Vicini et al. (2003 ▶); Sharmeen et al. (2001 ▶). Various synthetic routes have been developed for the synthesis of 1,2-benzisothia­zole-1,1-dioxides, see: Chapman & Peart (1996 ▶). Carbonation of ortho-lithia­ted sulfonamides is the most common method for the preparation of substituted saccharins; however, this results in poor yields (Lombardino, 1971 ▶) and is limited by the availability of starting materials. A recent improved synthesis of 1,2-benzisothia­zole-1,1-dioxides involved cyclization of N-acyl-benzene­sulfonamides using LDA, see: Hermann et al. (1992 ▶).

Experimental

Crystal data

C11H12ClNO4S

M = 289.73

Triclinic,

a = 7.578 (5) Å

b = 7.904 (6) Å

c = 10.002 (7) Å

α = 88.875 (11)°

β = 86.293 (10)°

γ = 84.176 (11)°

V = 594.7 (7) Å3

Z = 2

Synchrotron radiation

λ = 0.6937 Å

μ = 0.50 mm−1

T = 120 K

0.20 × 0.04 × 0.01 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.905, T max = 0.990

4651 measured reflections

2237 independent reflections

1671 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.177

S = 1.02

2237 reflections

167 parameters

H-atom parameters constrained

Δρmax = 1.29 e Å−3

Δρmin = −0.43 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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 and local programs.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810049561/jh2234sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810049561/jh2234Isup2.hkl

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

C11H12ClNO4S	Z = 2
Mr = 289.73	F(000) = 300
Triclinic, P1	Dx = 1.618 Mg m−3
Hall symbol: -P 1	Synchrotron radiation, λ = 0.6937 Å
a = 7.578 (5) Å	Cell parameters from 974 reflections
b = 7.904 (6) Å	θ = 2.6–24.5°
c = 10.002 (7) Å	µ = 0.50 mm−1
α = 88.875 (11)°	T = 120 K
β = 86.293 (10)°	Needle, colourless
γ = 84.176 (11)°	0.20 × 0.04 × 0.01 mm
V = 594.7 (7) Å3

Bruker APEXII CCD diffractometer	2237 independent reflections
Radiation source: Daresbury SRS station 9.8	1671 reflections with I > 2σ(I)
silicon 111	Rint = 0.038
thin–slice ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −9→9
Tmin = 0.905, Tmax = 0.990	k = −9→9
4651 measured reflections	l = −12→12

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)] = 0.065	H-atom parameters constrained
wR(F2) = 0.177	w = 1/[σ2(Fo2) + (0.0319P)2 + 1.6618P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2237 reflections	Δρmax = 1.29 e Å−3
167 parameters	Δρmin = −0.43 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.084 (15)

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	0.20714 (16)	0.29186 (15)	0.38990 (10)	0.0286 (4)
Cl1	0.72928 (18)	0.01424 (17)	0.14119 (11)	0.0402 (4)
N1	0.3721 (5)	0.2029 (5)	0.2891 (3)	0.0315 (9)
C1	0.3515 (8)	0.2190 (8)	0.1449 (4)	0.0441 (14)
H1A	0.4303	0.3002	0.1058	0.066*
H1B	0.2279	0.2595	0.1290	0.066*
H1C	0.3823	0.1079	0.1031	0.066*
C2	0.5330 (6)	0.1725 (6)	0.3483 (4)	0.0277 (10)
C3	0.6901 (7)	0.0988 (6)	0.2982 (4)	0.0353 (12)
H3	0.7873	0.0931	0.3541	0.042*
C4	0.5098 (6)	0.2358 (5)	0.4871 (4)	0.0255 (10)
C5	0.6343 (6)	0.2194 (6)	0.5848 (4)	0.0270 (10)
H5	0.7509	0.1660	0.5653	0.032*
C6	0.5834 (6)	0.2829 (6)	0.7102 (4)	0.0268 (10)
C7	0.4134 (6)	0.3697 (6)	0.7387 (4)	0.0255 (10)
C8	0.2894 (6)	0.3844 (6)	0.6435 (4)	0.0271 (10)
H8	0.1733	0.4400	0.6615	0.033*
C9	0.3435 (6)	0.3132 (6)	0.5189 (4)	0.0250 (10)
C10	0.8610 (6)	0.1808 (6)	0.7939 (5)	0.0328 (11)
H10A	0.8510	0.0663	0.7612	0.049*
H10B	0.9205	0.1726	0.8782	0.049*
H10C	0.9306	0.2431	0.7271	0.049*
C11	0.2152 (7)	0.5175 (7)	0.8980 (5)	0.0354 (11)
H11A	0.1882	0.6091	0.8329	0.053*
H11B	0.2138	0.5654	0.9878	0.053*
H11C	0.1258	0.4362	0.8971	0.053*
O1	0.0829 (5)	0.1725 (4)	0.4255 (3)	0.0371 (8)
O2	0.1341 (5)	0.4480 (4)	0.3321 (3)	0.0358 (8)
O3	0.6882 (4)	0.2685 (4)	0.8156 (3)	0.0316 (8)
O4	0.3860 (4)	0.4328 (4)	0.8638 (3)	0.0320 (8)

	U11	U22	U33	U12	U13	U23
S1	0.0357 (7)	0.0326 (7)	0.0185 (6)	−0.0065 (5)	−0.0058 (5)	0.0001 (4)
Cl1	0.0493 (8)	0.0498 (8)	0.0204 (6)	0.0003 (6)	−0.0013 (5)	−0.0052 (5)
N1	0.039 (2)	0.043 (2)	0.0123 (17)	−0.0009 (18)	−0.0043 (16)	−0.0005 (16)
C1	0.052 (3)	0.068 (4)	0.012 (2)	−0.006 (3)	−0.008 (2)	0.002 (2)
C2	0.036 (3)	0.027 (2)	0.020 (2)	−0.003 (2)	0.0002 (18)	0.0020 (18)
C3	0.054 (3)	0.036 (3)	0.017 (2)	−0.010 (2)	−0.003 (2)	−0.0034 (19)
C4	0.033 (2)	0.026 (2)	0.018 (2)	−0.0053 (19)	−0.0008 (18)	−0.0002 (17)
C5	0.028 (2)	0.032 (2)	0.020 (2)	−0.0014 (19)	−0.0004 (18)	0.0004 (18)
C6	0.029 (2)	0.034 (2)	0.019 (2)	−0.0067 (19)	−0.0039 (17)	0.0038 (18)
C7	0.034 (2)	0.029 (2)	0.0132 (19)	−0.0050 (19)	0.0020 (17)	−0.0001 (16)
C8	0.030 (2)	0.030 (2)	0.022 (2)	−0.0059 (19)	−0.0021 (18)	0.0008 (18)
C9	0.029 (2)	0.029 (2)	0.017 (2)	−0.0033 (19)	−0.0032 (17)	0.0023 (17)
C10	0.034 (3)	0.036 (3)	0.029 (2)	−0.001 (2)	−0.011 (2)	0.001 (2)
C11	0.039 (3)	0.042 (3)	0.024 (2)	−0.002 (2)	0.005 (2)	−0.006 (2)
O1	0.041 (2)	0.042 (2)	0.0306 (18)	−0.0136 (16)	−0.0048 (15)	−0.0041 (15)
O2	0.044 (2)	0.0359 (19)	0.0287 (17)	−0.0017 (15)	−0.0140 (15)	0.0039 (14)
O3	0.0333 (18)	0.0432 (19)	0.0182 (15)	−0.0007 (15)	−0.0065 (13)	−0.0009 (13)
O4	0.0385 (19)	0.0414 (19)	0.0159 (15)	−0.0035 (15)	−0.0008 (13)	−0.0020 (13)

S1—N1	1.661 (4)	C5—C6	1.377 (6)
S1—C9	1.725 (4)	C6—C7	1.411 (7)
S1—O1	1.424 (4)	C6—O3	1.357 (5)
S1—O2	1.427 (3)	C7—C8	1.376 (6)
Cl1—C3	1.715 (5)	C7—O4	1.352 (5)
N1—C1	1.463 (5)	C8—H8	0.950
N1—C2	1.387 (6)	C8—C9	1.398 (6)
C1—H1A	0.980	C10—H10A	0.980
C1—H1B	0.980	C10—H10B	0.980
C1—H1C	0.980	C10—H10C	0.980
C2—C3	1.342 (7)	C10—O3	1.424 (6)
C2—C4	1.478 (6)	C11—H11A	0.980
C3—H3	0.950	C11—H11B	0.980
C4—C5	1.397 (6)	C11—H11C	0.980
C4—C9	1.365 (6)	C11—O4	1.420 (6)
C5—H5	0.950
N1—S1—C9	93.3 (2)	C5—C6—C7	121.5 (4)
N1—S1—O1	110.3 (2)	C5—C6—O3	124.1 (4)
N1—S1—O2	109.9 (2)	C7—C6—O3	114.4 (4)
C9—S1—O1	110.6 (2)	C6—C7—C8	120.6 (4)
C9—S1—O2	115.1 (2)	C6—C7—O4	114.7 (4)
O1—S1—O2	115.4 (2)	C8—C7—O4	124.7 (4)
S1—N1—C1	117.1 (3)	C7—C8—H8	121.8
S1—N1—C2	114.2 (3)	C7—C8—C9	116.3 (4)
C1—N1—C2	125.1 (4)	H8—C8—C9	121.8
N1—C1—H1A	109.5	S1—C9—C4	110.2 (3)
N1—C1—H1B	109.5	S1—C9—C8	125.5 (4)
N1—C1—H1C	109.5	C4—C9—C8	124.1 (4)
H1A—C1—H1B	109.5	H10A—C10—H10B	109.5
H1A—C1—H1C	109.5	H10A—C10—H10C	109.5
H1B—C1—H1C	109.5	H10A—C10—O3	109.5
N1—C2—C3	129.9 (4)	H10B—C10—H10C	109.5
N1—C2—C4	108.7 (4)	H10B—C10—O3	109.5
C3—C2—C4	121.4 (4)	H10C—C10—O3	109.5
Cl1—C3—C2	125.2 (4)	H11A—C11—H11B	109.5
Cl1—C3—H3	117.4	H11A—C11—H11C	109.5
C2—C3—H3	117.4	H11A—C11—O4	109.5
C2—C4—C5	127.5 (4)	H11B—C11—H11C	109.5
C2—C4—C9	113.3 (4)	H11B—C11—O4	109.5
C5—C4—C9	119.3 (4)	H11C—C11—O4	109.5
C4—C5—H5	120.9	C6—O3—C10	117.2 (4)
C4—C5—C6	118.2 (4)	C7—O4—C11	116.7 (4)
H5—C5—C6	120.9
C9—S1—N1—C1	−155.2 (4)	C5—C6—C7—O4	−176.5 (4)
C9—S1—N1—C2	4.6 (4)	O3—C6—C7—C8	−176.0 (4)
O1—S1—N1—C1	91.4 (4)	O3—C6—C7—O4	3.6 (6)
O1—S1—N1—C2	−108.8 (3)	C6—C7—C8—C9	−1.5 (6)
O2—S1—N1—C1	−37.0 (4)	O4—C7—C8—C9	178.9 (4)
O2—S1—N1—C2	122.8 (3)	C2—C4—C9—S1	6.2 (5)
S1—N1—C2—C3	177.8 (4)	C2—C4—C9—C8	−179.5 (4)
S1—N1—C2—C4	−1.8 (5)	C5—C4—C9—S1	−171.9 (3)
C1—N1—C2—C3	−24.3 (8)	C5—C4—C9—C8	2.5 (7)
C1—N1—C2—C4	156.1 (5)	C7—C8—C9—S1	171.8 (3)
N1—C2—C3—Cl1	−2.1 (7)	C7—C8—C9—C4	−1.6 (7)
C4—C2—C3—Cl1	177.5 (3)	N1—S1—C9—C4	−6.2 (3)
N1—C2—C4—C5	174.9 (4)	N1—S1—C9—C8	179.6 (4)
N1—C2—C4—C9	−2.9 (5)	O1—S1—C9—C4	107.0 (3)
C3—C2—C4—C5	−4.8 (7)	O1—S1—C9—C8	−67.3 (4)
C3—C2—C4—C9	177.4 (4)	O2—S1—C9—C4	−120.0 (3)
C2—C4—C5—C6	−177.8 (4)	O2—S1—C9—C8	65.8 (4)
C9—C4—C5—C6	0.0 (6)	C5—C6—O3—C10	−0.5 (6)
C4—C5—C6—C7	−3.1 (7)	C7—C6—O3—C10	179.4 (4)
C4—C5—C6—O3	176.8 (4)	C6—C7—O4—C11	−178.5 (4)
C5—C6—C7—C8	3.9 (7)	C8—C7—O4—C11	1.1 (6)