2-[2-(3-Chloro-phen-yl)-2-oxoeth-yl]-1,2-benzisothia-zol-3(2H)-one 1,1-dioxide.

In the title compound, C(15)H(10)ClNO(4)S, the benzothia-zole ring system is essentially planar [maximum deviation = 0.0382 (13) Å for the N atom] and forms a dihedral angle of 74.43 (6)° with the chloro-substituted benzene ring. In the crystal structure, weak inter-molecular C-H⋯O hydrogen bonds form R(2) (2)(10) and R(2) (2)(16) ring motifs.

Related literature

For the use of 1,2-benzisothia­zoline-3-one 1,1-dioxide (saccharine) as an inter­mediate in the preparation of medicinally important mol­ecules, see: Siddiqui et al. (2006 ▶); Zia-ur-Rehman et al. (2005 ▶, 2009 ▶). For the biological activity of saccharine, see: Singh et al. (2007 ▶); Vaccarino et al. (2007 ▶); Kapui et al. (2003 ▶). For related structures, see: Ahmad et al. (2008 ▶, 2009 ▶). For hydrogen-bonding motifs, see: Bernstein et al. (1995 ▶). Zia-ur-Rehman, Choudary & Ahmad (2005 ▶).

Experimental

Crystal data

C15H10ClNO4S

M = 335.75

Triclinic,

a = 7.7258 (4) Å

b = 9.0780 (4) Å

c = 10.0809 (5) Å

α = 83.884 (3)°

β = 85.092 (3)°

γ = 87.765 (3)°

V = 700.10 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.44 mm−1

T = 173 K

0.20 × 0.12 × 0.10 mm

Data collection

Nonius diffractometer with Bruker APEXII CCD

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.917, T max = 0.957

5768 measured reflections

3157 independent reflections

2881 reflections with (I) > 2.0 σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.130

S = 1.06

3157 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.40 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: HKL DENZO (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK (Otwinowski & Minor, 1997 ▶); 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 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks Global, I. DOI: 10.1107/S1600536810005428/lh2992sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810005428/lh2992Isup2.hkl

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

C15H10ClNO4S	Z = 2
Mr = 335.75	F(000) = 344
Triclinic, P1	Dx = 1.593 Mg m−3
Hall symbol: -P 1	Melting point: 488 K
a = 7.7258 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.0780 (4) Å	Cell parameters from 2955 reflections
c = 10.0809 (5) Å	θ = 1.0–27.5°
α = 83.884 (3)°	µ = 0.44 mm−1
β = 85.092 (3)°	T = 173 K
γ = 87.765 (3)°	Prism, white
V = 700.10 (6) Å3	0.20 × 0.12 × 0.10 mm

Nonius APEXII CCD diffractometer	3157 independent reflections
Radiation source: fine-focus sealed tube	2881 reflections with (I) > 2.0 σ(I)
graphite	Rint = 0.025
φ & ω scans	θmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −10→9
Tmin = 0.917, Tmax = 0.957	k = −11→11
5768 measured reflections	l = −12→13

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0738P)2 + 0.5259P] where P = (Fo2 + 2Fc2)/3
3157 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.40 e Å−3

Experimental. IR (KBr): 1737, 1690, 1341, 1151 cm-1, 1H NMR: (DMSO-d6) δ: 5.40 (s, 2H, CH2), 7.43 (dd, 1H, J1 = 2.4 Hz, J2 = 8.4 Hz, Ar—H), 7.50 (t, 1H, J = 8.0 Hz, Ar—H), 7.58 (t, 1H, J = 2.4 Hz, Ar—H), 7.65 (d, 1H, J = 7.6 Hz, Ar—H), 8.05 (t, 1H, J = 7.6 Hz, Ar—H), 8.11 (t, 1H, J = 7.6 Hz, Ar—H), 8.17 (d, 1H, J = 7.6 Hz, Ar—H), 8.23 (d, 1H, J = 7.2 Hz, Ar—H). MS m/z: 335.8[M+].

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
Cl1	0.05636 (8)	0.97635 (7)	0.83644 (5)	0.03594 (18)
S1	0.13366 (6)	0.50633 (5)	0.22038 (5)	0.02250 (15)
O1	0.57018 (19)	0.54728 (17)	0.34507 (15)	0.0275 (3)
O2	0.0709 (2)	0.62625 (18)	0.13199 (17)	0.0340 (4)
O3	0.0067 (2)	0.42357 (19)	0.30583 (17)	0.0341 (4)
O4	0.3503 (2)	0.85538 (18)	0.25316 (16)	0.0360 (4)
N1	0.2798 (2)	0.56575 (19)	0.31383 (17)	0.0237 (4)
C1	0.2881 (2)	0.3923 (2)	0.13935 (19)	0.0206 (4)
C2	0.2593 (3)	0.2980 (2)	0.0452 (2)	0.0259 (4)
H2	0.1469	0.2874	0.0166	0.031*
C3	0.4039 (3)	0.2192 (2)	−0.0055 (2)	0.0285 (4)
H3	0.3898	0.1525	−0.0700	0.034*
C4	0.5687 (3)	0.2356 (2)	0.0359 (2)	0.0279 (4)
H4	0.6648	0.1808	−0.0012	0.034*
C5	0.5948 (3)	0.3314 (2)	0.1312 (2)	0.0239 (4)
H5	0.7071	0.3424	0.1598	0.029*
C6	0.4518 (3)	0.4102 (2)	0.18287 (18)	0.0197 (4)
C7	0.4493 (3)	0.5143 (2)	0.28697 (19)	0.0207 (4)
C8	0.2318 (3)	0.6673 (2)	0.4143 (2)	0.0237 (4)
H8A	0.2891	0.6334	0.4968	0.028*
H8B	0.1046	0.6660	0.4367	0.028*
C9	0.2845 (3)	0.8255 (2)	0.3652 (2)	0.0232 (4)
C10	0.2549 (3)	0.9392 (2)	0.46202 (19)	0.0216 (4)
C11	0.1755 (3)	0.9062 (2)	0.5907 (2)	0.0219 (4)
H11	0.1351	0.8095	0.6193	0.026*
C12	0.1567 (3)	1.0164 (2)	0.6761 (2)	0.0237 (4)
C13	0.2149 (3)	1.1584 (2)	0.6376 (2)	0.0277 (4)
H13	0.2020	1.2324	0.6979	0.033*
C14	0.2926 (3)	1.1900 (2)	0.5085 (2)	0.0307 (5)
H14	0.3325	1.2868	0.4804	0.037*
C15	0.3124 (3)	1.0828 (2)	0.4209 (2)	0.0266 (4)
H15	0.3648	1.1062	0.3328	0.032*

	U11	U22	U33	U12	U13	U23
Cl1	0.0441 (3)	0.0384 (3)	0.0246 (3)	−0.0009 (2)	0.0080 (2)	−0.0084 (2)
S1	0.0185 (2)	0.0232 (3)	0.0262 (3)	0.00100 (18)	−0.00166 (18)	−0.00494 (19)
O1	0.0254 (7)	0.0312 (8)	0.0276 (8)	−0.0025 (6)	−0.0057 (6)	−0.0074 (6)
O2	0.0318 (8)	0.0319 (8)	0.0386 (9)	0.0082 (7)	−0.0110 (7)	−0.0020 (7)
O3	0.0245 (8)	0.0375 (9)	0.0398 (9)	−0.0060 (7)	0.0071 (7)	−0.0073 (7)
O4	0.0505 (10)	0.0325 (8)	0.0234 (8)	−0.0037 (7)	0.0081 (7)	−0.0037 (6)
N1	0.0221 (8)	0.0248 (8)	0.0252 (8)	0.0024 (7)	−0.0022 (6)	−0.0087 (7)
C1	0.0206 (9)	0.0200 (9)	0.0207 (9)	0.0005 (7)	0.0003 (7)	−0.0017 (7)
C2	0.0257 (10)	0.0271 (10)	0.0258 (10)	−0.0028 (8)	−0.0042 (8)	−0.0047 (8)
C3	0.0366 (12)	0.0261 (10)	0.0238 (10)	−0.0025 (8)	−0.0007 (8)	−0.0083 (8)
C4	0.0300 (10)	0.0279 (10)	0.0250 (10)	0.0041 (8)	0.0027 (8)	−0.0047 (8)
C5	0.0218 (9)	0.0254 (10)	0.0238 (10)	0.0007 (8)	0.0009 (7)	−0.0016 (8)
C6	0.0234 (9)	0.0185 (9)	0.0168 (8)	−0.0013 (7)	−0.0005 (7)	−0.0007 (7)
C7	0.0224 (9)	0.0182 (9)	0.0210 (9)	−0.0007 (7)	−0.0010 (7)	−0.0007 (7)
C8	0.0280 (10)	0.0216 (9)	0.0217 (9)	0.0010 (8)	0.0010 (8)	−0.0067 (7)
C9	0.0219 (9)	0.0258 (10)	0.0216 (9)	0.0011 (7)	−0.0014 (7)	−0.0025 (8)
C10	0.0217 (9)	0.0220 (9)	0.0215 (9)	0.0002 (7)	−0.0020 (7)	−0.0032 (7)
C11	0.0222 (9)	0.0209 (9)	0.0227 (9)	0.0007 (7)	−0.0007 (7)	−0.0031 (7)
C12	0.0252 (10)	0.0270 (10)	0.0193 (9)	0.0017 (8)	−0.0025 (7)	−0.0041 (7)
C13	0.0317 (11)	0.0244 (10)	0.0289 (11)	0.0010 (8)	−0.0073 (8)	−0.0076 (8)
C14	0.0390 (12)	0.0214 (10)	0.0319 (11)	−0.0038 (9)	−0.0053 (9)	−0.0007 (8)
C15	0.0325 (11)	0.0244 (10)	0.0228 (10)	−0.0032 (8)	−0.0024 (8)	−0.0003 (8)

Cl1—C12	1.740 (2)	C5—C6	1.387 (3)
S1—O2	1.4285 (16)	C5—H5	0.9500
S1—O3	1.4297 (16)	C6—C7	1.483 (3)
S1—N1	1.6707 (18)	C8—C9	1.528 (3)
S1—C1	1.755 (2)	C8—H8A	0.9900
O1—C7	1.207 (2)	C8—H8B	0.9900
O4—C9	1.206 (3)	C9—C10	1.493 (3)
N1—C7	1.388 (3)	C10—C11	1.395 (3)
N1—C8	1.456 (2)	C10—C15	1.403 (3)
C1—C2	1.381 (3)	C11—C12	1.384 (3)
C1—C6	1.394 (3)	C11—H11	0.9500
C2—C3	1.393 (3)	C12—C13	1.387 (3)
C2—H2	0.9500	C13—C14	1.391 (3)
C3—C4	1.392 (3)	C13—H13	0.9500
C3—H3	0.9500	C14—C15	1.377 (3)
C4—C5	1.394 (3)	C14—H14	0.9500
C4—H4	0.9500	C15—H15	0.9500
O2—S1—O3	116.98 (10)	N1—C7—C6	108.78 (17)
O2—S1—N1	110.34 (9)	N1—C8—C9	111.68 (16)
O3—S1—N1	108.98 (10)	N1—C8—H8A	109.3
O2—S1—C1	112.54 (10)	C9—C8—H8A	109.3
O3—S1—C1	112.63 (10)	N1—C8—H8B	109.3
N1—S1—C1	92.62 (9)	C9—C8—H8B	109.3
C7—N1—C8	122.70 (17)	H8A—C8—H8B	107.9
C7—N1—S1	115.44 (14)	O4—C9—C10	121.91 (19)
C8—N1—S1	121.85 (14)	O4—C9—C8	120.72 (19)
C2—C1—C6	122.96 (18)	C10—C9—C8	117.36 (17)
C2—C1—S1	127.13 (16)	C11—C10—C15	119.82 (19)
C6—C1—S1	109.90 (14)	C11—C10—C9	122.23 (18)
C1—C2—C3	116.44 (19)	C15—C10—C9	117.94 (18)
C1—C2—H2	121.8	C12—C11—C10	118.92 (18)
C3—C2—H2	121.8	C12—C11—H11	120.5
C4—C3—C2	121.64 (19)	C10—C11—H11	120.5
C4—C3—H3	119.2	C11—C12—C13	121.94 (19)
C2—C3—H3	119.2	C11—C12—Cl1	119.16 (16)
C3—C4—C5	120.9 (2)	C13—C12—Cl1	118.90 (16)
C3—C4—H4	119.5	C12—C13—C14	118.45 (19)
C5—C4—H4	119.5	C12—C13—H13	120.8
C6—C5—C4	118.02 (19)	C14—C13—H13	120.8
C6—C5—H5	121.0	C15—C14—C13	121.0 (2)
C4—C5—H5	121.0	C15—C14—H14	119.5
C5—C6—C1	119.99 (18)	C13—C14—H14	119.5
C5—C6—C7	126.87 (18)	C14—C15—C10	119.9 (2)
C1—C6—C7	113.12 (17)	C14—C15—H15	120.1
O1—C7—N1	123.66 (18)	C10—C15—H15	120.1
O1—C7—C6	127.50 (18)
O2—S1—N1—C7	−111.61 (16)	C8—N1—C7—C6	178.35 (16)
O3—S1—N1—C7	118.65 (15)	S1—N1—C7—C6	−3.0 (2)
C1—S1—N1—C7	3.62 (16)	C5—C6—C7—O1	−0.6 (3)
O2—S1—N1—C8	67.08 (18)	C1—C6—C7—O1	177.71 (19)
O3—S1—N1—C8	−62.65 (18)	C5—C6—C7—N1	−177.90 (19)
C1—S1—N1—C8	−177.68 (16)	C1—C6—C7—N1	0.5 (2)
O2—S1—C1—C2	−69.4 (2)	C7—N1—C8—C9	75.9 (2)
O3—S1—C1—C2	65.5 (2)	S1—N1—C8—C9	−102.69 (18)
N1—S1—C1—C2	177.32 (19)	N1—C8—C9—O4	3.1 (3)
O2—S1—C1—C6	110.17 (15)	N1—C8—C9—C10	−175.59 (17)
O3—S1—C1—C6	−114.98 (15)	O4—C9—C10—C11	178.6 (2)
N1—S1—C1—C6	−3.15 (15)	C8—C9—C10—C11	−2.8 (3)
C6—C1—C2—C3	0.1 (3)	O4—C9—C10—C15	−2.4 (3)
S1—C1—C2—C3	179.62 (16)	C8—C9—C10—C15	176.20 (18)
C1—C2—C3—C4	−0.4 (3)	C15—C10—C11—C12	−0.7 (3)
C2—C3—C4—C5	0.5 (3)	C9—C10—C11—C12	178.30 (18)
C3—C4—C5—C6	−0.3 (3)	C10—C11—C12—C13	−0.2 (3)
C4—C5—C6—C1	0.0 (3)	C10—C11—C12—Cl1	179.53 (15)
C4—C5—C6—C7	178.24 (18)	C11—C12—C13—C14	0.7 (3)
C2—C1—C6—C5	0.1 (3)	Cl1—C12—C13—C14	−179.03 (17)
S1—C1—C6—C5	−179.49 (15)	C12—C13—C14—C15	−0.3 (3)
C2—C1—C6—C7	−178.41 (18)	C13—C14—C15—C10	−0.5 (3)
S1—C1—C6—C7	2.0 (2)	C11—C10—C15—C14	1.0 (3)
C8—N1—C7—O1	1.0 (3)	C9—C10—C15—C14	−178.0 (2)
S1—N1—C7—O1	179.65 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2i	0.95	2.40	3.249 (3)	148
C8—H8A···O1ii	0.99	2.45	3.378 (3)	156
C11—H11···O3iii	0.95	2.44	3.382 (3)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2i	0.95	2.40	3.249 (3)	148
C8—H8A⋯O1ii	0.99	2.45	3.378 (3)	156
C11—H11⋯O3iii	0.95	2.44	3.382 (3)	173

Symmetry codes: (i) ; (ii) ; (iii) .