4-Methyl-N-(3-oxo-2,3-dihydro-1,2-benzisothia-zol-2-yl)benzene-sulfonamide.

In the title mol-ecule, C(14)H(12)N(2)O(3)S(2), the benzisothia-zolone 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, mol-ecules are linked via inter-molecular 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 = 320.38

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.089

S = 1.01

3521 reflections

194 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.28 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/S1600536809003201/lh2764sup1.cif

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

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

C14H12N2O3S2	F(000) = 664
Mr = 320.38	Dx = 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

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

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 = 1.00	w = 1/[σ2(Fo2) + (0.0354P)2] where P = (Fo2 + 2Fc2)/3
3521 reflections	(Δ/σ)max < 0.001
194 parameters	Δρmax = 0.23 e Å−3
1 restraint	Δρmin = −0.28 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
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*

	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)

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

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

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) ; (ii) .