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

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

doi:10.1107/S1600536809003201

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Pages o425-o426

doi:10.1107/S1600536809003201

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4-Methyl-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 molecule, C₁₄H₁₂N₂O₃S₂, the benzisothiazolone ring system is essentially planar and forms a dihedral angle of 67.37 (6)° with the plane of the benzene ring. In the crystal structure, molecules are linked via intermolecular N—H⋯O and C—H⋯O hydrogen bonds to form chains parallel to the b axis.

Related literature

For the chemical and biological properties of 1,2-benzisothiazol-3(2H)-one derivatives, see: Clerici et al. (2007 ); Siegemund et al. (2002 ). For 2-amino-1,2-benzisothiazol-3(2H)-one derivatives with antiplatelet/spasmolitic effects, see: Vicini et al. (1997 ,2000 ). For derivatives with antimicrobial properties, see: Vicini et al. (2002 ); Zani et al. (2004 ). For the synthesis of the title compound, see: Vicini et al. (2009 ). For the crystal structures of related 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

C₁₄H₁₂N₂O₃S₂
M_r = 320.38
Monoclinic, P 2₁ /n
a = 8.051 (3) Å
b = 7.655 (3) Å
c = 23.910 (10) Å
β = 98.490 (8)°
V = 1457.4 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.38 mm⁻¹
T = 296 (2) K
0.28 × 0.26 × 0.12 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.892, T_max = 0.957
17685 measured reflections
3521 independent reflections
1888 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.089
S = 1.01
3521 reflections
194 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1ⁱ	0.848 (17)	1.948 (17)	2.784 (3)	168.3 (15)
C6—H6⋯O2ⁱⁱ	0.93	2.56	3.492 (3)	175
Symmetry codes: (i) $[-x-{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x+1, y, z.

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/S1600536809003201/lh2764sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809003201/lh2764Isup2.hkl

checkCIF report

Comment top

Over the past decades a substantial number of 1,2-benzisothiazol-3(2H)-one derivatives have been reported to possess a wide range of biological activities including antimicrobial, antiviral, anticancer, anti-inflammatory, cartilage antidegenerative and other pharmacological activities (Clerici et al., 2007; Siegemund et al., 2002). As part of our program aimed at developing novel biologically active 1,2-benzisothiazol-3(2H)-ones, we have synthesized in the last years 2-amino-1,2-benzisothiazol-3(2H)-one derivatives resulted in the discovery of new compounds active as antiplatelet/spasmolitic agents (Vicini et al., 1997; Vicini et al., 2000) and of compounds endowed with very interesting antimicrobial properties (Vicini et al., 2002; Zani et al., 2004). Recently, in our continuing efforts to find novel effective 2-amino-1,2-benzisothiazol-3(2H)-one derivatives, we have synthesized a series of 2-(phenylsulfonyl)amino-1,2-benzisothiazol-3(2H)-ones which exhibit anti-HIV-1 activity against wild type virus and against viral strains carrying clinically relevant mutations (Vicini et al., 2009). Experimental evidences suggest non classical targets for this novel class of anti-HIV-1 agents. In order to study their binding sites at a molecular level we thought it appropriate to obtain X-ray crystallographic data for a prototype.

The molecule of the title compound (Fig. 1) shows no unusual geometric features, with the S1—N1 (1.7116 (19) Å) and S1—C1 (1.721 (2) Å) bond distances corresponding to those observed in similar structures (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 (1.364 (2) Å) is just significantly shorter than that observed in 4,5-dimethyl-2-(3-nitrobenzenesulfonylamino)isothiazol-3(2H)-one 1,1-dioxide (1.387 (4) Å; Kolberg et al., 1999). The benzoisothiazole rings system is essentially planar (maximum deviation 0.019 (4) Å for atom C4) and forms a dihedral angle of 67.37 (6)° with the plane of the C8–C13 benzene ring. In the crystal structure (Fig. 2), molecules are linked into chains running parallel to the b axis by intermolecular N—H···O and C—H···O hydrogen bonding interactions (Table 1).

Related literature top

For the chemical and biological properties of 1,2-benzisothiazol-3(2H)-one derivatives, see: Clerici et al. (2007); Siegemund et al. (2002). For 2-amino-1,2-benzisothiazol-3(2H)-one derivatives with antiplatelet/spasmolitic effects, see: Vicini et al. (1997,2000). For derivatives with antimicrobial properties, see: Vicini et al. (2002); Zani et al. (2004). For the synthesis of the title compound, see: Vicini et al. (2009). For the crystal structures of related 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 as described elsewhere (Vicini et al., 2009). Freshly prepared chlorocarbonylsulfenylchloride (18 mmol) in dried CCl₄ (40 ml) was added dropwise to a stirred, ice-cooled solution of 2-tosylhydrazine (20 mmol) in pyridine (18 ml). After 2 h the reaction mixture was allowed to cool to room temperature and the crude product was filtered, purified by base-acid (Na₂CO₃—HCl) exchange and silica-gel column chromatography (eluent CH₂Cl₂—EtOH 95:5 v/v). Pale yellow single crystals of the title compound suitable for X-ray analysis were obtained by 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 b axis. Intemolecular N—H···O and C–H···O hydrogen bonds are shown as dashed lines.

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

Crystal data top

C₁₄H₁₂N₂O₃S₂	F(000) = 664
M_r = 320.38	D_x = 1.460 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1208 reflections
a = 8.051 (3) Å	θ = 3.1–54.7°
b = 7.655 (3) Å	µ = 0.38 mm⁻¹
c = 23.91 (1) Å	T = 296 K
β = 98.490 (8)°	Prism, pale yellow
V = 1457.4 (10) Å³	0.28 × 0.26 × 0.12 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3521 independent reflections
Radiation source: fine-focus sealed tube	1888 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
ω scans	θ_max = 28.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −10→10
T_min = 0.892, T_max = 0.957	k = −10→10
17685 measured reflections	l = −31→31

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0354P)²] where P = (F_o² + 2F_c²)/3
3521 reflections	(Δ/σ)_max < 0.001
194 parameters	Δρ_max = 0.23 e Å⁻³
1 restraint	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₄H₁₂N₂O₃S₂	V = 1457.4 (10) Å³
M_r = 320.38	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.051 (3) Å	µ = 0.38 mm⁻¹
b = 7.655 (3) Å	T = 296 K
c = 23.91 (1) Å	0.28 × 0.26 × 0.12 mm
β = 98.490 (8)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3521 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	1888 reflections with I > 2σ(I)
T_min = 0.892, T_max = 0.957	R_int = 0.041
17685 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	1 restraint
wR(F²) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.23 e Å⁻³
3521 reflections	Δρ_min = −0.28 e Å⁻³
194 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
S1	0.07092 (8)	0.54275 (7)	0.15129 (2)	0.0674 (2)
S2	−0.38794 (7)	0.64261 (7)	0.12617 (2)	0.06196 (18)
O1	−0.25352 (19)	0.2912 (2)	0.21942 (6)	0.0740 (4)
O2	−0.4086 (2)	0.48129 (18)	0.09686 (6)	0.0795 (5)
O3	−0.5189 (2)	0.7130 (2)	0.15313 (7)	0.0826 (5)
N1	−0.1134 (2)	0.4976 (2)	0.17603 (7)	0.0585 (5)
N2	−0.2283 (3)	0.6277 (2)	0.17766 (8)	0.0692 (5)
H2	−0.247 (3)	0.670 (3)	0.2089 (6)	0.085 (8)*
C1	−0.1300 (3)	0.3352 (2)	0.19864 (8)	0.0524 (5)
C2	0.0211 (2)	0.2380 (2)	0.19334 (8)	0.0469 (5)
C3	0.0556 (3)	0.0671 (3)	0.21027 (8)	0.0584 (5)
H3	−0.0221	0.0028	0.2269	0.070*
C4	0.2040 (3)	−0.0051 (3)	0.20233 (10)	0.0702 (6)
H4	0.2268	−0.1211	0.2122	0.084*
C5	0.3219 (3)	0.0936 (3)	0.17950 (10)	0.0796 (7)
H5	0.4249	0.0432	0.1758	0.096*
C6	0.2925 (3)	0.2611 (3)	0.16232 (10)	0.0722 (6)
H6	0.3724	0.3250	0.1467	0.087*
C7	0.1378 (3)	0.3337 (2)	0.16900 (8)	0.0527 (5)
C8	−0.3251 (2)	0.7991 (3)	0.08016 (8)	0.0544 (5)
C9	−0.3198 (3)	0.7587 (3)	0.02474 (10)	0.0815 (7)
H9	−0.3454	0.6466	0.0111	0.098*
C10	−0.2757 (4)	0.8877 (4)	−0.01057 (10)	0.0977 (9)
H10	−0.2729	0.8606	−0.0483	0.117*
C11	−0.2362 (3)	1.0529 (4)	0.00758 (12)	0.0789 (7)
C12	−0.2448 (3)	1.0894 (3)	0.06352 (11)	0.0793 (7)
H12	−0.2203	1.2017	0.0772	0.095*
C13	−0.2886 (3)	0.9645 (3)	0.09934 (10)	0.0708 (6)
H13	−0.2935	0.9922	0.1369	0.085*
C14	−0.1871 (4)	1.1911 (4)	−0.03204 (12)	0.1226 (12)
H14A	−0.1661	1.2993	−0.0120	0.184*
H14B	−0.2766	1.2068	−0.0629	0.184*
H14C	−0.0874	1.1549	−0.0464	0.184*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0837 (4)	0.0494 (3)	0.0742 (4)	−0.0037 (3)	0.0287 (3)	0.0081 (3)
S2	0.0711 (4)	0.0537 (3)	0.0623 (4)	0.0114 (3)	0.0140 (3)	0.0072 (3)
O1	0.0561 (9)	0.0904 (11)	0.0790 (10)	0.0106 (8)	0.0222 (8)	0.0324 (9)
O2	0.1055 (13)	0.0531 (9)	0.0784 (11)	−0.0047 (8)	0.0092 (9)	−0.0016 (8)
O3	0.0789 (11)	0.0863 (11)	0.0896 (12)	0.0260 (9)	0.0360 (9)	0.0181 (9)
N1	0.0668 (12)	0.0489 (10)	0.0626 (11)	0.0159 (9)	0.0193 (9)	0.0127 (8)
N2	0.0929 (14)	0.0660 (12)	0.0483 (11)	0.0358 (11)	0.0092 (10)	0.0007 (10)
C1	0.0538 (13)	0.0556 (13)	0.0484 (12)	0.0027 (10)	0.0099 (10)	0.0099 (10)
C2	0.0457 (12)	0.0437 (11)	0.0508 (11)	0.0001 (9)	0.0055 (9)	0.0021 (9)
C3	0.0598 (14)	0.0514 (13)	0.0610 (13)	0.0000 (10)	−0.0004 (11)	0.0053 (10)
C4	0.0759 (17)	0.0548 (13)	0.0760 (16)	0.0139 (13)	−0.0013 (13)	−0.0038 (12)
C5	0.0670 (16)	0.0808 (18)	0.0911 (18)	0.0205 (14)	0.0121 (14)	−0.0180 (14)
C6	0.0622 (15)	0.0765 (16)	0.0834 (16)	−0.0070 (13)	0.0287 (13)	−0.0146 (14)
C7	0.0552 (13)	0.0498 (12)	0.0543 (12)	−0.0030 (10)	0.0122 (10)	−0.0045 (9)
C8	0.0579 (13)	0.0556 (12)	0.0491 (12)	0.0104 (10)	0.0056 (10)	0.0034 (10)
C9	0.111 (2)	0.0751 (16)	0.0603 (16)	−0.0120 (15)	0.0195 (14)	−0.0075 (13)
C10	0.125 (2)	0.119 (2)	0.0504 (15)	−0.0115 (19)	0.0165 (15)	0.0051 (16)
C11	0.0669 (16)	0.0886 (19)	0.0774 (19)	−0.0017 (14)	−0.0021 (13)	0.0278 (16)
C12	0.0940 (19)	0.0613 (15)	0.0808 (19)	−0.0026 (13)	0.0065 (14)	0.0065 (14)
C13	0.0920 (18)	0.0637 (15)	0.0571 (14)	0.0010 (13)	0.0125 (13)	−0.0009 (12)
C14	0.108 (2)	0.143 (3)	0.114 (2)	−0.014 (2)	0.0065 (18)	0.070 (2)

Geometric parameters (Å, º) top

S1—N1	1.7116 (19)	C5—H5	0.9300
S1—C7	1.721 (2)	C6—C7	1.394 (3)
S2—O2	1.4175 (16)	C6—H6	0.9300
S2—O3	1.4205 (15)	C8—C13	1.364 (3)
S2—N2	1.647 (2)	C8—C9	1.368 (3)
S2—C8	1.751 (2)	C9—C10	1.380 (3)
O1—C1	1.223 (2)	C9—H9	0.9300
N1—N2	1.364 (2)	C10—C11	1.359 (3)
N1—C1	1.370 (2)	C10—H10	0.9300
N2—H2	0.844 (9)	C11—C12	1.378 (3)
C1—C2	1.448 (3)	C11—C14	1.511 (3)
C2—C3	1.385 (3)	C12—C13	1.364 (3)
C2—C7	1.386 (2)	C12—H12	0.9300
C3—C4	1.355 (3)	C13—H13	0.9300
C3—H3	0.9300	C14—H14A	0.9600
C4—C5	1.387 (3)	C14—H14B	0.9600
C4—H4	0.9300	C14—H14C	0.9600
C5—C6	1.356 (3)

N1—S1—C7	89.03 (9)	C5—C6—H6	121.3
O2—S2—O3	120.93 (11)	C7—C6—H6	121.3
O2—S2—N2	109.30 (10)	C2—C7—C6	120.65 (19)
O3—S2—N2	103.69 (10)	C2—C7—S1	112.83 (15)
O2—S2—C8	107.99 (10)	C6—C7—S1	126.50 (17)
O3—S2—C8	109.17 (10)	C13—C8—C9	120.0 (2)
N2—S2—C8	104.56 (10)	C13—C8—S2	119.47 (17)
N2—N1—C1	123.02 (17)	C9—C8—S2	120.50 (18)
N2—N1—S1	119.29 (14)	C8—C9—C10	118.6 (2)
C1—N1—S1	117.36 (13)	C8—C9—H9	120.7
N1—N2—S2	119.16 (15)	C10—C9—H9	120.7
N1—N2—H2	120.6 (16)	C11—C10—C9	122.7 (2)
S2—N2—H2	114.6 (16)	C11—C10—H10	118.7
O1—C1—N1	122.89 (18)	C9—C10—H10	118.7
O1—C1—C2	129.65 (18)	C10—C11—C12	117.1 (2)
N1—C1—C2	107.45 (17)	C10—C11—C14	121.4 (3)
C3—C2—C7	120.20 (18)	C12—C11—C14	121.5 (3)
C3—C2—C1	126.50 (18)	C13—C12—C11	121.5 (2)
C7—C2—C1	113.30 (17)	C13—C12—H12	119.3
C4—C3—C2	119.2 (2)	C11—C12—H12	119.3
C4—C3—H3	120.4	C12—C13—C8	120.2 (2)
C2—C3—H3	120.4	C12—C13—H13	119.9
C3—C4—C5	120.1 (2)	C8—C13—H13	119.9
C3—C4—H4	119.9	C11—C14—H14A	109.5
C5—C4—H4	119.9	C11—C14—H14B	109.5
C6—C5—C4	122.3 (2)	H14A—C14—H14B	109.5
C6—C5—H5	118.8	C11—C14—H14C	109.5
C4—C5—H5	118.8	H14A—C14—H14C	109.5
C5—C6—C7	117.5 (2)	H14B—C14—H14C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.85 (2)	1.95 (2)	2.784 (3)	168 (2)
C6—H6···O2ⁱⁱ	0.93	2.56	3.492 (3)	175

Symmetry codes: (i) −x−1/2, y+1/2, −z+1/2; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂N₂O₃S₂
M_r	320.38
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	8.051 (3), 7.655 (3), 23.91 (1)
β (°)	98.490 (8)
V (Å³)	1457.4 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.38
Crystal size (mm)	0.28 × 0.26 × 0.12

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.892, 0.957
No. of measured, independent and observed [I > 2σ(I)] reflections	17685, 3521, 1888
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.089, 1.01
No. of reflections	3521
No. of parameters	194
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.28

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
N2—H2···O1ⁱ	0.848 (17)	1.948 (17)	2.784 (3)	168.3 (15)
C6—H6···O2ⁱⁱ	0.93	2.56	3.492 (3)	175

Symmetry codes: (i) −x−1/2, y+1/2, −z+1/2; (ii) x+1, y, z.

Acknowledgements

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

References

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