N-(3-Chloro-phen-yl)-1,2-benzisothia-zol-3-amine 1,1-dioxide.

In the title compound, C(13)H(9)ClN(2)O(2)S, the dihedral angle between the aromatic ring systems is 6.00 (12)° and an intra-molecular C-H⋯N inter-action generates an S(6) ring. In the crystal, mol-ecules inter-act by way of C-H⋯O and N-H⋯O bonds, generating R(2) (1)(7) and R(2) (2)(10) ring motifs, and aromatic π-π stacking inter-actions [centroid-centroid separations = 3.730 (3) and 3.733 (2) Å] help to consolidate the packing.

Related literature

For other saccharin derivatives, see: Rafique et al. (2009 ▶); Siddiqui et al. (2010 ▶). For a related structure, see: Brigas et al. (2001 ▶). For graph-set theory, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H9ClN2O2S

M = 292.73

Triclinic,

a = 7.2223 (10) Å

b = 7.9138 (12) Å

c = 11.2175 (17) Å

α = 96.178 (6)°

β = 98.840 (5)°

γ = 97.574 (5)°

V = 622.63 (16) Å3

Z = 2

Mo Kα radiation

μ = 0.47 mm−1

T = 296 K

0.28 × 0.10 × 0.08 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.947, T max = 0.962

10481 measured reflections

2700 independent reflections

1244 reflections with I > 2σ(I)

R int = 0.088

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.115

S = 0.98

2700 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810015163/hb5389sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015163/hb5389Isup2.hkl

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

C13H9ClN2O2S	Z = 2
Mr = 292.73	F(000) = 300
Triclinic, P1	Dx = 1.561 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2223 (10) Å	Cell parameters from 1244 reflections
b = 7.9138 (12) Å	θ = 2.6–27.1°
c = 11.2175 (17) Å	µ = 0.47 mm−1
α = 96.178 (6)°	T = 296 K
β = 98.840 (5)°	Needle, colourless
γ = 97.574 (5)°	0.28 × 0.10 × 0.08 mm
V = 622.63 (16) Å3

Bruker Kappa APEXII CCD diffractometer	2700 independent reflections
Radiation source: fine-focus sealed tube	1244 reflections with I > 2σ(I)
graphite	Rint = 0.088
Detector resolution: 7.60 pixels mm-1	θmax = 27.1°, θmin = 2.6°
ω scans	h = −8→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −10→10
Tmin = 0.947, Tmax = 0.962	l = −14→14
10481 measured reflections

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.0363P)2] where P = (Fo2 + 2Fc2)/3
2700 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

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
C1	1.1663 (5)	0.2836 (4)	0.4969 (3)	0.0380 (9)
C2	1.2431 (5)	0.3741 (5)	0.6082 (3)	0.0512 (11)
H2	1.3719	0.4162	0.6278	0.061*
C3	1.1225 (6)	0.4010 (5)	0.6905 (3)	0.0566 (12)
H3	1.1705	0.4625	0.7668	0.068*
C4	0.9329 (6)	0.3379 (5)	0.6609 (4)	0.0557 (11)
H4	0.8542	0.3572	0.7177	0.067*
C5	0.8563 (5)	0.2460 (5)	0.5481 (3)	0.0466 (10)
H5	0.7275	0.2038	0.5289	0.056*
C6	0.9745 (5)	0.2185 (4)	0.4651 (3)	0.0352 (9)
C7	0.9368 (5)	0.1246 (4)	0.3407 (3)	0.0374 (9)
C8	0.6944 (4)	−0.0592 (4)	0.1789 (3)	0.0361 (9)
C9	0.5043 (5)	−0.1312 (5)	0.1558 (3)	0.0426 (10)
H9	0.4257	−0.1074	0.2119	0.051*
C10	0.4338 (5)	−0.2380 (5)	0.0491 (3)	0.0415 (10)
C11	0.5448 (5)	−0.2769 (5)	−0.0357 (3)	0.0482 (10)
H11	0.4944	−0.3497	−0.1073	0.058*
C12	0.7330 (5)	−0.2050 (5)	−0.0116 (3)	0.0485 (11)
H12	0.8109	−0.2302	−0.0677	0.058*
C13	0.8080 (5)	−0.0967 (5)	0.0939 (3)	0.0457 (10)
H13	0.9353	−0.0485	0.1081	0.055*
Cl1	0.19425 (13)	−0.32624 (14)	0.02129 (9)	0.0658 (4)
N1	0.7608 (4)	0.0472 (4)	0.2912 (3)	0.0417 (8)
H1	0.6751	0.0650	0.3345	0.050*
N2	1.0821 (4)	0.1190 (4)	0.2841 (3)	0.0428 (8)
O1	1.4055 (3)	0.1090 (3)	0.4010 (2)	0.0619 (8)
O2	1.3450 (4)	0.3710 (3)	0.3184 (2)	0.0645 (8)
S1	1.27387 (13)	0.22471 (14)	0.37119 (9)	0.0481 (3)

	U11	U22	U33	U12	U13	U23
C1	0.029 (2)	0.039 (2)	0.041 (2)	−0.0055 (17)	0.0023 (17)	0.0026 (19)
C2	0.044 (2)	0.052 (3)	0.047 (3)	−0.011 (2)	−0.003 (2)	−0.001 (2)
C3	0.062 (3)	0.062 (3)	0.039 (3)	−0.004 (2)	0.002 (2)	−0.002 (2)
C4	0.056 (3)	0.063 (3)	0.045 (3)	−0.001 (2)	0.013 (2)	−0.001 (2)
C5	0.036 (2)	0.059 (3)	0.041 (2)	−0.0003 (19)	0.0038 (19)	0.002 (2)
C6	0.033 (2)	0.039 (2)	0.033 (2)	0.0038 (17)	0.0032 (17)	0.0035 (19)
C7	0.028 (2)	0.037 (2)	0.043 (2)	−0.0002 (17)	0.0007 (17)	0.0000 (19)
C8	0.028 (2)	0.040 (2)	0.036 (2)	0.0022 (17)	0.0018 (17)	−0.0021 (19)
C9	0.030 (2)	0.048 (3)	0.047 (3)	−0.0001 (18)	0.0107 (18)	−0.005 (2)
C10	0.027 (2)	0.042 (3)	0.049 (3)	−0.0019 (17)	0.0015 (18)	−0.005 (2)
C11	0.040 (2)	0.054 (3)	0.044 (2)	−0.0013 (19)	0.0037 (19)	−0.010 (2)
C12	0.036 (2)	0.064 (3)	0.042 (2)	0.002 (2)	0.0083 (19)	−0.007 (2)
C13	0.024 (2)	0.065 (3)	0.044 (2)	0.0020 (18)	0.0045 (18)	0.001 (2)
Cl1	0.0325 (6)	0.0807 (9)	0.0706 (8)	−0.0122 (5)	0.0055 (5)	−0.0205 (6)
N1	0.0249 (16)	0.054 (2)	0.0411 (19)	−0.0042 (14)	0.0069 (14)	−0.0036 (16)
N2	0.0248 (16)	0.057 (2)	0.0421 (19)	−0.0024 (14)	0.0065 (14)	−0.0062 (16)
O1	0.0289 (15)	0.077 (2)	0.073 (2)	0.0088 (14)	0.0005 (13)	−0.0092 (17)
O2	0.0539 (18)	0.070 (2)	0.0632 (19)	−0.0227 (15)	0.0210 (15)	0.0020 (16)
S1	0.0261 (5)	0.0609 (8)	0.0494 (7)	−0.0073 (5)	0.0045 (5)	−0.0087 (6)

C1—C2	1.367 (5)	C8—C9	1.389 (4)
C1—C6	1.390 (4)	C8—N1	1.417 (4)
C1—S1	1.760 (4)	C9—C10	1.374 (5)
C2—C3	1.382 (5)	C9—H9	0.9300
C2—H2	0.9300	C10—C11	1.370 (5)
C3—C4	1.371 (5)	C10—Cl1	1.746 (3)
C3—H3	0.9300	C11—C12	1.376 (4)
C4—C5	1.384 (5)	C11—H11	0.9300
C4—H4	0.9300	C12—C13	1.375 (5)
C5—C6	1.376 (4)	C12—H12	0.9300
C5—H5	0.9300	C13—H13	0.9300
C6—C7	1.477 (5)	N1—H1	0.8600
C7—N2	1.310 (4)	N2—S1	1.635 (3)
C7—N1	1.343 (4)	O1—S1	1.432 (3)
C8—C13	1.384 (4)	O2—S1	1.428 (3)
C2—C1—C6	122.5 (3)	C10—C9—H9	120.4
C2—C1—S1	130.4 (3)	C8—C9—H9	120.4
C6—C1—S1	107.1 (3)	C11—C10—C9	122.3 (3)
C1—C2—C3	117.7 (4)	C11—C10—Cl1	119.2 (3)
C1—C2—H2	121.2	C9—C10—Cl1	118.5 (3)
C3—C2—H2	121.2	C10—C11—C12	118.0 (3)
C4—C3—C2	120.7 (4)	C10—C11—H11	121.0
C4—C3—H3	119.6	C12—C11—H11	121.0
C2—C3—H3	119.6	C13—C12—C11	121.3 (3)
C3—C4—C5	121.3 (4)	C13—C12—H12	119.3
C3—C4—H4	119.4	C11—C12—H12	119.3
C5—C4—H4	119.4	C12—C13—C8	120.0 (3)
C6—C5—C4	118.7 (4)	C12—C13—H13	120.0
C6—C5—H5	120.7	C8—C13—H13	120.0
C4—C5—H5	120.7	C7—N1—C8	130.1 (3)
C5—C6—C1	119.2 (3)	C7—N1—H1	115.0
C5—C6—C7	131.3 (3)	C8—N1—H1	115.0
C1—C6—C7	109.5 (3)	C7—N2—S1	109.9 (2)
N2—C7—N1	122.9 (3)	O2—S1—O1	115.88 (17)
N2—C7—C6	116.9 (3)	O2—S1—N2	110.41 (16)
N1—C7—C6	120.2 (3)	O1—S1—N2	109.76 (16)
C13—C8—C9	119.3 (3)	O2—S1—C1	111.86 (17)
C13—C8—N1	123.8 (3)	O1—S1—C1	110.64 (17)
C9—C8—N1	116.9 (3)	N2—S1—C1	96.63 (15)
C10—C9—C8	119.1 (3)
C6—C1—C2—C3	−0.3 (6)	Cl1—C10—C11—C12	179.7 (3)
S1—C1—C2—C3	−179.8 (3)	C10—C11—C12—C13	−0.3 (6)
C1—C2—C3—C4	0.3 (6)	C11—C12—C13—C8	0.6 (6)
C2—C3—C4—C5	−0.1 (6)	C9—C8—C13—C12	−0.5 (5)
C3—C4—C5—C6	0.0 (6)	N1—C8—C13—C12	178.3 (3)
C4—C5—C6—C1	−0.1 (5)	N2—C7—N1—C8	4.0 (6)
C4—C5—C6—C7	178.8 (4)	C6—C7—N1—C8	−174.8 (3)
C2—C1—C6—C5	0.2 (6)	C13—C8—N1—C7	−3.2 (6)
S1—C1—C6—C5	179.8 (3)	C9—C8—N1—C7	175.6 (3)
C2—C1—C6—C7	−178.9 (3)	N1—C7—N2—S1	−179.4 (3)
S1—C1—C6—C7	0.8 (4)	C6—C7—N2—S1	−0.6 (4)
C5—C6—C7—N2	−179.1 (4)	C7—N2—S1—O2	−115.4 (3)
C1—C6—C7—N2	−0.1 (4)	C7—N2—S1—O1	115.7 (3)
C5—C6—C7—N1	−0.2 (6)	C7—N2—S1—C1	0.9 (3)
C1—C6—C7—N1	178.7 (3)	C2—C1—S1—O2	−66.3 (4)
C13—C8—C9—C10	0.1 (5)	C6—C1—S1—O2	114.1 (3)
N1—C8—C9—C10	−178.8 (3)	C2—C1—S1—O1	64.5 (4)
C8—C9—C10—C11	0.2 (6)	C6—C1—S1—O1	−115.0 (3)
C8—C9—C10—Cl1	−179.6 (3)	C2—C1—S1—N2	178.6 (4)
C9—C10—C11—C12	−0.1 (6)	C6—C1—S1—N2	−1.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···N2	0.93	2.28	2.901 (5)	124
N1—H1···O1i	0.86	2.24	3.084 (4)	165
C5—H5···O1i	0.93	2.51	3.396 (4)	159
C2—H2···O2ii	0.93	2.42	3.302 (4)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯N2	0.93	2.28	2.901 (5)	124
N1—H1⋯O1i	0.86	2.24	3.084 (4)	165
C5—H5⋯O1i	0.93	2.51	3.396 (4)	159
C2—H2⋯O2ii	0.93	2.42	3.302 (4)	158

Symmetry codes: (i) ; (ii) .