4-Chloro-N-(4-chloro-phenyl-sulfon-yl)-N-(3-oxo-2,3-dihydro-1,2-benzisothia-zol-2-yl)benzene-sulfonamide.

In the title compound, C(19)H(12)Cl(2)N(2)O(5)S(3), the benzene rings of the chloro-phenyl-sulfonyl groups form a dihedral angle of 35.85 (8)° and are inclined at angles of 23.51 (6) and 59.22 (6)° with respect to the essentially planar benzisothia-zole ring system [maximum deviation = 0.030 (2) Å]. The mol-ecular conformation is stabilized by an intra-molecular C-H⋯O hydrogen bond. In the crystal packing, mol-ecules are linked into chains parallel to the a axis by inter-molecular C-H⋯O hydrogen bonds and π-π stacking inter-actions, with centroid-centroid distances of 3.592 (5) Å.

Related literature

For the synthesis and biological activity of 1,2-benzisothia­zol-3(2H)-ones and 2-amino-1,2-benzisothia­zol-3(2H)-one derivatives, see: Clerici et al. (2007 ▶); Siegemund et al. (2002 ▶); Vicini et al. (1997 ▶). For the synthesis of the title compound, see: Vicini et al. (2009 ▶). For the crystal structures of related benzisothia­zole compounds, see: Cavalca et al. (1970 ▶); Ranganathan et al. (2002 ▶); Steinfeld & Kersting (2006 ▶); Kim et al. (1996 ▶); Xu et al. (2006 ▶); Sarma & Mugesh (2007 ▶); Kolberg et al. (1999 ▶).

Experimental

Crystal data

C19H12Cl2N2O5S3

M = 515.39

Triclinic,

a = 9.5358 (12) Å

b = 10.7757 (14) Å

c = 11.0393 (14) Å

α = 102.719 (2)°

β = 94.385 (3)°

γ = 105.598 (2)°

V = 1054.6 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.64 mm−1

T = 295 (2) K

0.22 × 0.14 × 0.12 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.872, T max = 0.927

10953 measured reflections

3930 independent reflections

2267 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.060

S = 0.94

3930 reflections

280 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and SCHAKAL (Keller, 1997 ▶); software used to prepare material for publication: SHELXL97 and PARST95 (Nardelli, 1995 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809003195/lh2763sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003195/lh2763Isup2.hkl

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

C19H12Cl2N2O5S3	Z = 2
Mr = 515.39	F(000) = 524
Triclinic, P1	Dx = 1.623 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.5358 (12) Å	Cell parameters from 1477 reflections
b = 10.7757 (14) Å	θ = 4.8–47.8°
c = 11.0393 (14) Å	µ = 0.64 mm−1
α = 102.719 (2)°	T = 295 K
β = 94.385 (3)°	Prism, pale yellow
γ = 105.598 (2)°	0.22 × 0.14 × 0.12 mm
V = 1054.6 (2) Å3

Bruker SMART 1000 CCD area-detector diffractometer	3930 independent reflections
Radiation source: fine-focus sealed tube	2267 reflections with I > 2σ(I)
graphite	Rint = 0.037
ω scans	θmax = 25.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −11→11
Tmin = 0.872, Tmax = 0.927	k = −13→13
10953 measured reflections	l = −13→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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.060	H-atom parameters constrained
S = 0.94	w = 1/[σ2(Fo2) + (0.0145P)2] where P = (Fo2 + 2Fc2)/3
3930 reflections	(Δ/σ)max = 0.001
280 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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	0.30528 (10)	0.89637 (7)	0.94340 (8)	0.0862 (3)
Cl2	0.37123 (10)	0.47508 (9)	1.37354 (8)	0.1051 (3)
S1	0.13674 (7)	−0.02399 (6)	0.62308 (7)	0.0550 (2)
S2	0.14511 (8)	0.31023 (7)	0.62932 (7)	0.0539 (2)
S3	0.01047 (7)	0.21135 (7)	0.84324 (7)	0.0515 (2)
O1	0.43050 (18)	0.27563 (17)	0.83915 (17)	0.0630 (5)
O2	0.2660 (2)	0.28393 (17)	0.57181 (16)	0.0677 (5)
O3	0.00450 (19)	0.27802 (16)	0.55643 (16)	0.0687 (6)
O4	−0.07297 (17)	0.29573 (16)	0.81554 (16)	0.0605 (5)
O5	−0.05678 (18)	0.07361 (16)	0.83264 (17)	0.0639 (5)
N1	0.2112 (2)	0.12783 (18)	0.73222 (19)	0.0501 (6)
N2	0.1337 (2)	0.22006 (18)	0.74166 (18)	0.0476 (5)
C1	0.3647 (3)	0.1683 (3)	0.7692 (2)	0.0478 (7)
C2	0.4188 (3)	0.0593 (2)	0.7077 (2)	0.0451 (6)
C3	0.5641 (3)	0.0591 (3)	0.7197 (2)	0.0554 (7)
H3	0.6367	0.1309	0.7718	0.066*
C4	0.5991 (3)	−0.0492 (3)	0.6532 (3)	0.0654 (8)
H4	0.6964	−0.0507	0.6600	0.078*
C5	0.4911 (3)	−0.1560 (3)	0.5762 (3)	0.0638 (8)
H5	0.5174	−0.2288	0.5330	0.077*
C6	0.3462 (3)	−0.1582 (3)	0.5614 (2)	0.0575 (7)
H6	0.2744	−0.2306	0.5090	0.069*
C7	0.3110 (3)	−0.0472 (2)	0.6283 (2)	0.0462 (6)
C8	0.1916 (3)	0.4758 (2)	0.7178 (2)	0.0477 (7)
C9	0.0978 (3)	0.5504 (3)	0.7018 (2)	0.0560 (7)
H9	0.0109	0.5132	0.6456	0.067*
C10	0.1350 (3)	0.6819 (3)	0.7707 (3)	0.0611 (8)
H10	0.0739	0.7342	0.7603	0.073*
C11	0.2626 (3)	0.7341 (2)	0.8544 (2)	0.0561 (7)
C12	0.3557 (3)	0.6602 (3)	0.8706 (3)	0.0657 (8)
H12	0.4419	0.6976	0.9275	0.079*
C13	0.3203 (3)	0.5293 (3)	0.8017 (3)	0.0614 (8)
H13	0.3826	0.4779	0.8117	0.074*
C14	0.1174 (2)	0.2839 (2)	0.9908 (2)	0.0450 (6)
C15	0.1572 (3)	0.2053 (3)	1.0622 (3)	0.0630 (8)
H15	0.1308	0.1134	1.0312	0.076*
C16	0.2365 (3)	0.2648 (3)	1.1799 (3)	0.0772 (9)
H16	0.2630	0.2130	1.2295	0.093*
C17	0.2764 (3)	0.4011 (3)	1.2242 (3)	0.0632 (8)
C18	0.2397 (3)	0.4797 (3)	1.1525 (3)	0.0593 (8)
H18	0.2694	0.5718	1.1826	0.071*
C19	0.1583 (3)	0.4206 (2)	1.0355 (3)	0.0531 (7)
H19	0.1309	0.4726	0.9866	0.064*

	U11	U22	U33	U12	U13	U23
Cl1	0.1137 (7)	0.0495 (5)	0.0768 (6)	0.0059 (4)	0.0144 (5)	−0.0001 (4)
Cl2	0.1116 (7)	0.1090 (7)	0.0712 (6)	0.0070 (6)	−0.0208 (5)	0.0175 (5)
S1	0.0427 (4)	0.0480 (4)	0.0663 (5)	0.0159 (3)	−0.0044 (4)	−0.0012 (4)
S2	0.0533 (5)	0.0505 (5)	0.0519 (5)	0.0148 (4)	0.0004 (4)	0.0035 (4)
S3	0.0382 (4)	0.0465 (4)	0.0652 (5)	0.0107 (3)	0.0072 (4)	0.0067 (4)
O1	0.0498 (11)	0.0554 (12)	0.0689 (13)	0.0092 (10)	−0.0101 (10)	−0.0007 (10)
O2	0.0727 (13)	0.0704 (13)	0.0658 (13)	0.0290 (11)	0.0304 (11)	0.0121 (10)
O3	0.0659 (12)	0.0604 (12)	0.0646 (13)	0.0196 (10)	−0.0240 (10)	−0.0055 (10)
O4	0.0441 (10)	0.0671 (12)	0.0743 (13)	0.0273 (10)	0.0043 (9)	0.0136 (10)
O5	0.0517 (11)	0.0423 (11)	0.0842 (14)	−0.0009 (9)	0.0102 (10)	0.0064 (10)
N1	0.0398 (13)	0.0440 (13)	0.0617 (15)	0.0170 (11)	0.0009 (11)	−0.0002 (11)
N2	0.0433 (12)	0.0427 (13)	0.0591 (14)	0.0168 (10)	0.0119 (11)	0.0108 (11)
C1	0.0416 (16)	0.0511 (18)	0.0499 (18)	0.0127 (14)	0.0007 (14)	0.0139 (14)
C2	0.0411 (16)	0.0508 (17)	0.0444 (17)	0.0155 (14)	0.0053 (13)	0.0119 (13)
C3	0.0402 (16)	0.0617 (19)	0.068 (2)	0.0166 (14)	0.0050 (15)	0.0228 (16)
C4	0.0469 (18)	0.081 (2)	0.086 (2)	0.0333 (18)	0.0151 (17)	0.0384 (19)
C5	0.065 (2)	0.067 (2)	0.072 (2)	0.0377 (18)	0.0179 (18)	0.0175 (17)
C6	0.0581 (19)	0.0574 (19)	0.0596 (19)	0.0262 (15)	0.0077 (15)	0.0086 (15)
C7	0.0459 (16)	0.0517 (17)	0.0457 (17)	0.0204 (14)	0.0083 (14)	0.0136 (14)
C8	0.0442 (16)	0.0445 (16)	0.0512 (17)	0.0087 (13)	0.0069 (14)	0.0111 (13)
C9	0.0483 (17)	0.0503 (18)	0.065 (2)	0.0112 (14)	0.0023 (15)	0.0121 (15)
C10	0.0604 (19)	0.0529 (19)	0.071 (2)	0.0164 (16)	0.0114 (17)	0.0163 (16)
C11	0.0647 (19)	0.0431 (17)	0.0545 (19)	0.0032 (15)	0.0185 (16)	0.0121 (14)
C12	0.0598 (19)	0.056 (2)	0.064 (2)	0.0015 (16)	−0.0087 (16)	0.0054 (16)
C13	0.0516 (17)	0.0563 (19)	0.071 (2)	0.0160 (15)	−0.0043 (16)	0.0104 (16)
C14	0.0384 (15)	0.0426 (16)	0.0527 (17)	0.0126 (13)	0.0082 (13)	0.0080 (14)
C15	0.065 (2)	0.0434 (17)	0.081 (2)	0.0162 (15)	0.0061 (18)	0.0180 (17)
C16	0.079 (2)	0.069 (2)	0.086 (3)	0.0211 (19)	−0.006 (2)	0.031 (2)
C17	0.0556 (18)	0.068 (2)	0.062 (2)	0.0124 (16)	0.0010 (15)	0.0160 (17)
C18	0.0550 (18)	0.0442 (17)	0.070 (2)	0.0097 (14)	0.0032 (16)	0.0049 (16)
C19	0.0511 (17)	0.0461 (18)	0.0614 (19)	0.0136 (14)	0.0074 (15)	0.0134 (15)

Cl1—C11	1.729 (3)	C5—H5	0.9300
Cl2—C17	1.726 (3)	C6—C7	1.399 (3)
S1—N1	1.7347 (19)	C6—H6	0.9300
S1—C7	1.744 (2)	C8—C9	1.379 (3)
S2—O2	1.4214 (17)	C8—C13	1.381 (3)
S2—O3	1.4239 (16)	C9—C10	1.388 (3)
S2—N2	1.729 (2)	C9—H9	0.9300
S2—C8	1.754 (2)	C10—C11	1.371 (3)
S3—O4	1.4240 (16)	C10—H10	0.9300
S3—O5	1.4242 (16)	C11—C12	1.368 (3)
S3—N2	1.684 (2)	C12—C13	1.383 (3)
S3—C14	1.750 (3)	C12—H12	0.9300
O1—C1	1.213 (3)	C13—H13	0.9300
N1—N2	1.381 (2)	C14—C15	1.379 (3)
N1—C1	1.409 (3)	C14—C19	1.381 (3)
C1—C2	1.461 (3)	C15—C16	1.376 (4)
C2—C3	1.383 (3)	C15—H15	0.9300
C2—C7	1.388 (3)	C16—C17	1.377 (4)
C3—C4	1.371 (3)	C16—H16	0.9300
C3—H3	0.9300	C17—C18	1.370 (3)
C4—C5	1.380 (3)	C18—C19	1.377 (3)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.371 (3)	C19—H19	0.9300
N1—S1—C7	89.10 (11)	C2—C7—S1	113.04 (18)
O2—S2—O3	120.38 (11)	C6—C7—S1	126.2 (2)
O2—S2—N2	102.15 (10)	C9—C8—C13	121.2 (2)
O3—S2—N2	109.77 (11)	C9—C8—S2	118.9 (2)
O2—S2—C8	110.89 (11)	C13—C8—S2	119.9 (2)
O3—S2—C8	108.61 (12)	C8—C9—C10	119.0 (2)
N2—S2—C8	103.62 (11)	C8—C9—H9	120.5
O4—S3—O5	121.61 (11)	C10—C9—H9	120.5
O4—S3—N2	104.10 (10)	C11—C10—C9	119.4 (3)
O5—S3—N2	106.59 (10)	C11—C10—H10	120.3
O4—S3—C14	109.51 (11)	C9—C10—H10	120.3
O5—S3—C14	109.23 (12)	C12—C11—C10	121.6 (3)
N2—S3—C14	104.29 (10)	C12—C11—Cl1	119.2 (2)
N2—N1—C1	120.88 (19)	C10—C11—Cl1	119.1 (2)
N2—N1—S1	117.96 (15)	C11—C12—C13	119.4 (3)
C1—N1—S1	116.69 (17)	C11—C12—H12	120.3
N1—N2—S3	115.94 (15)	C13—C12—H12	120.3
N1—N2—S2	117.41 (15)	C8—C13—C12	119.3 (3)
S3—N2—S2	125.38 (12)	C8—C13—H13	120.4
O1—C1—N1	122.8 (2)	C12—C13—H13	120.4
O1—C1—C2	130.4 (2)	C15—C14—C19	120.8 (2)
N1—C1—C2	106.9 (2)	C15—C14—S3	120.4 (2)
C3—C2—C7	120.6 (2)	C19—C14—S3	118.8 (2)
C3—C2—C1	125.3 (2)	C16—C15—C14	119.1 (3)
C7—C2—C1	114.1 (2)	C16—C15—H15	120.5
C4—C3—C2	118.7 (3)	C14—C15—H15	120.5
C4—C3—H3	120.7	C15—C16—C17	119.9 (3)
C2—C3—H3	120.7	C15—C16—H16	120.0
C3—C4—C5	120.6 (2)	C17—C16—H16	120.0
C3—C4—H4	119.7	C18—C17—C16	121.2 (3)
C5—C4—H4	119.7	C18—C17—Cl2	119.0 (2)
C6—C5—C4	122.1 (3)	C16—C17—Cl2	119.9 (2)
C6—C5—H5	119.0	C17—C18—C19	119.2 (3)
C4—C5—H5	119.0	C17—C18—H18	120.4
C5—C6—C7	117.2 (3)	C19—C18—H18	120.4
C5—C6—H6	121.4	C18—C19—C14	119.9 (3)
C7—C6—H6	121.4	C18—C19—H19	120.1
C2—C7—C6	120.8 (2)	C14—C19—H19	120.1

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1	0.93	2.42	3.275 (4)	153
C5—H5···O2i	0.93	2.58	3.353 (4)	140
C6—H6···O3ii	0.93	2.58	3.289 (3)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O1	0.93	2.42	3.275 (4)	153
C5—H5⋯O2i	0.93	2.58	3.353 (4)	140
C6—H6⋯O3ii	0.93	2.58	3.289 (3)	133

Symmetry codes: (i) ; (ii) .