4-Chloro-N-(4-chloro­phenyl­sulfon­yl)-N-(3-oxo-2,3-dihydro-1,2-benzisothia­zol-2-yl)benzene­sulfonamide

Rizzoli, C.; Vicini, P.; Incerti, M.

doi:10.1107/S1600536809003195

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Pages o416-o417

doi:10.1107/S1600536809003195

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4-Chloro-N-(4-chlorophenylsulfonyl)-N-(3-oxo-2,3-dihydro-1,2-benzisothiazol-2-yl)benzenesulfonamide

Corrado Rizzoli,^a ^* Paola Vicini ^b and Matteo Incerti ^b

^aDipartimento di Chimica Generale ed Inorganica, Chimica Analitica, Chimica Fisica, Viale G. P. Usberti 17/A, Universitá di Parma, I-43100 Parma, Italy, and ^bDipartimento Farmaceutico, Viale G. P. Usberti 27/A, Universitá di Parma, I-43100 Parma, Italy
^*Correspondence e-mail: corrado.rizzoli@unipr.it

(Received 22 January 2009; accepted 26 January 2009; online 31 January 2009)

In the title compound, C₁₉H₁₂Cl₂N₂O₅S₃, the benzene rings of the chlorophenylsulfonyl 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 benzisothiazole ring system [maximum deviation = 0.030 (2) Å]. The molecular conformation is stabilized by an intramolecular C—H⋯O hydrogen bond. In the crystal packing, molecules are linked into chains parallel to the a axis by intermolecular C—H⋯O hydrogen bonds and π–π stacking interactions, 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_r = 515.39
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.035
wR(F²) = 0.060
S = 0.94
3930 reflections
280 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.22 e Å⁻³

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) -x+1, -y, -z+1; (ii) -x, -y, -z+1.

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 ).

Supporting information

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

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

checkCIF report

Comment top

Among 1,2-benzisothiazol-3(2H)-ones, a class of compounds with a wide spectrum of biological activities (Clerici et al., 2007; Siegemund et al., 2002), 2-amino-1,2-benzisothiazol-3(2H)-one derivatives have a rather recent history and 2-amino-1,2-benzisothiazol-3(2H)-one was first synthesized by our group in 1997 (Vicini et al., 1997). Due to their peculiar reactivity, 2-amino-1,2-benzisothiazol-3(2H)-one derivatives have recently emerged as effective antiplatelet, spasmolytic and antimicrobial agents (Clerici et al., 2007; Siegemund et al., 2002). The therapeutic significance of the 2-amino-1,2-benzisothiazol-3(2H)-one ring system with suitably functionalized substituents has encorauged us to develop novel compounds. The title compound was obtained unintentionally as a by-product during the synthesis of 2-(benzenesulfonyl)amino-1,2-benzisothiazol-3(2H)-ones that have been demonstrated to possess anti-HIV-1 activity against wild type virus and against viral strains carrying clinically relevant mutations (Vicini et al., 2008). The unexpected 2-(bisphenylsulfonyl)amino-1,2-benzisothiazol-3(2H)-ones, subjected to biological evaluation as well, resulted fairly active and, interestingly, endowed with lower cytotoxicity with respect to their monophenylsulfonyl substituted counterparts. In view of the structure-activity relationship study of the novel 1,2-benzisothiazol-3(2H)-one benzenesulfonamides aimed at optimizing their antiretroviral potency, the representative title compound was synthesized and its crystal structure is reported here.

The molecular structure of the title compound is shown in Fig. 1. The bond lengths and angles are unexceptional. The S1—N1 and S1—C7 bond distances within the benzoisothiazole ring system are 1.7347 (19) and 1.744 (2) Å respectively, in good agreement with those reported is related compounds (Cavalca et al., 1970; Ranganathan et al., 2002; Steinfeld & Kersting, 2006; Kim et al., 1996; Xu et al., 2006; Sarma & Mugesh, 2007). The N1—N2 bond distance (1.381 (2) Å) is not significantly different from the corresponding distance in 4,5-dimethyl-2-(3-nitrobenzenesulfonylamino)isothiazol-3(2H)-one 1,1-dioxide (1.387 (4) Å; Kolberg et al., 1999). The C8–C13 and C14–C19 benzene rings form a dihedral angle of 35.85 (8)° and are tilted by 23.51 (6) and 59.22 (6)° with respect to the essentially planar benzoisothiazole rings system (maximum deviation 0.030 (2) Å for atom N1). The molecular structure is stabilized by an intramolecular C—H···O hydrogen bond (Table 1). In the crystal packing (Fig. 2), molecules are linked into chains running parallel to the a axis by intermolecular C—H···O hydrogen interactions (Table 1) and π-π stacking interactions occurring between the benzene rings of centrosymmetrically related benzisothiazole rings, with a centroid-to-centroid separation of 3.592 (5) Å, a perpendicular interplanar distance of 3.514 (5) Å and a centroid-centroid offset of 0.746 (4) Å (symmetry code linking the adjacent rings: 1 - x, -y, 1 - z).

Related literature top

For the synthesis and biological activities 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. (2008). For the crystal structure 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 top

The title compound was synthesized by reaction of 2-amino-1,2-benzisothiazol-3(2H)-one (10 mmol) with 4-chlorobenzenesulfonyl chloride (11 mmol) in pyridine (8 ml) for 2 h at 273K, resulting in a mixture of 4-chloro-N-(3-oxo-1,2-benzisothiazol-2(3H)-yl)benzenesulfonamide and 4-chloro-N-[(4-chlorophenyl)sulfonyl]-N-(3-oxo-1,2-benzisothiazol-2(3H)-yl)benzenesulfonamide (% yield ratio 33/66). Indeed, once the monophenylsulfonyl product is formed, a subsequent sulfonylation yielding the bisphenylsulfonyl derivative readily occurs, by the action of the electrophilic benzenesulfonyl chloride. The two products were simply separated because of the acidic character of the former. The crude product was poured into water (30 ml) and treated with a 10% aqueous sodium carbonate under stirring for 1 h, affording the title compound as insoluble solid that was collected by filtration. Pale yellow crystals suitable for X-ray analysis were obtained on slow evaporation of an ethanol solution at room temperature.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 (Sheldrick, 2008) and PARST95 (Nardelli, 1995).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Crystal packing of the title compound viewed approximately along the a axis. Red and green dashed lines indicate C–H···O hydrogen bonds and π-π stacking interactions, respectively.

4-Chloro-N-(4-chlorophenylsulfonyl)-N-(3-oxo-2,3-dihydro-1,2-benzisothiazol-2-yl)benzenesulfonamide top

Crystal data top

C₁₉H₁₂Cl₂N₂O₅S₃	Z = 2
M_r = 515.39	F(000) = 524
Triclinic, P1	D_x = 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

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3930 independent reflections
Radiation source: fine-focus sealed tube	2267 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ω scans	θ_max = 25.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −11→11
T_min = 0.872, T_max = 0.927	k = −13→13
10953 measured reflections	l = −13→13

Refinement top

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(F_o²) + (0.0145P)²] where P = (F_o² + 2F_c²)/3
3930 reflections	(Δ/σ)_max = 0.001
280 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₉H₁₂Cl₂N₂O₅S₃	γ = 105.598 (2)°
M_r = 515.39	V = 1054.6 (2) Å³
Triclinic, P1	Z = 2
a = 9.5358 (12) Å	Mo Kα radiation
b = 10.7757 (14) Å	µ = 0.64 mm⁻¹
c = 11.0393 (14) Å	T = 295 K
α = 102.719 (2)°	0.22 × 0.14 × 0.12 mm
β = 94.385 (3)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3930 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	2267 reflections with I > 2σ(I)
T_min = 0.872, T_max = 0.927	R_int = 0.037
10953 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.060	H-atom parameters constrained
S = 0.94	Δρ_max = 0.21 e Å⁻³
3930 reflections	Δρ_min = −0.22 e Å⁻³
280 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y, −z+1; (ii) −x, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₂Cl₂N₂O₅S₃
M_r	515.39
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	9.5358 (12), 10.7757 (14), 11.0393 (14)
α, β, γ (°)	102.719 (2), 94.385 (3), 105.598 (2)
V (Å³)	1054.6 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.64
Crystal size (mm)	0.22 × 0.14 × 0.12

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.872, 0.927
No. of measured, independent and observed [I > 2σ(I)] reflections	10953, 3930, 2267
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.060, 0.94
No. of reflections	3930
No. of parameters	280
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.22

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SIR97 (Altomare et al., 1999), ORTEP-3 for Windows (Farrugia, 1997) and SCHAKAL (Keller, 1997), SHELXL97 (Sheldrick, 2008) and PARST95 (Nardelli, 1995).

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y, −z+1; (ii) −x, −y, −z+1.

Acknowledgements

Financial support from the Italian MIUR (Ministero dell'Istruzione, dell'Universitá e della Ricerca) is gratefully acknowledged.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bruker (1997). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Volume 65| Part 2| February 2009| Pages o416-o417

doi:10.1107/S1600536809003195

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4-Chloro-N-(4-chloro­phenyl­sulfon­yl)-N-(3-oxo-2,3-di­hydro-1,2-benziso­thia­zol-2-yl)benzene­sulfonamide

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-Chloro-N-(4-chlorophenylsulfonyl)-N-(3-oxo-2,3-dihydro-1,2-benzisothiazol-2-yl)benzenesulfonamide