N-(3,5-Dichloro-phen-yl)-4-methyl-benzene-sulfonamide.

In the crystal structure of the title compound, C(13)H(11)Cl(2)NO(2)S, the conformation of the N-C bond in the C-SO(2)-NH-C segment is gauche with respect to the SO bonds. The two benzene rings are tilted by 79.6 (1)° relative to each other. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds occur.

Related literature

For the preparation of the title compound, see: Shetty & Gowda (2005 ▶). For background literature, see: For a study of the effect of substituents on the crystal structures of N-(ar­yl)-aryl­sulfonamides, see: Gowda et al. (2008 ▶, 2009 ▶). For bond parameters in related aryl sulfonamides, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C13H11Cl2NO2S

M = 316.19

Monoclinic,

a = 6.7388 (8) Å

b = 8.9627 (8) Å

c = 22.944 (2) Å

β = 91.801 (8)°

V = 1385.1 (2) Å3

Z = 4

Cu Kα radiation

μ = 5.61 mm−1

T = 299 K

0.42 × 0.35 × 0.13 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.140, T max = 0.482

3363 measured reflections

2424 independent reflections

2049 reflections with I > 2σ(I)

R int = 0.104

3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.236

S = 1.11

2424 reflections

176 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.48 e Å−3

Δρmin = −0.64 e Å−3

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809034801/bv2124sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034801/bv2124Isup2.hkl

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

C13H11Cl2NO2S	F(000) = 648
Mr = 316.19	Dx = 1.516 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 6.7388 (8) Å	θ = 3.9–18.2°
b = 8.9627 (8) Å	µ = 5.61 mm−1
c = 22.944 (2) Å	T = 299 K
β = 91.801 (8)°	Prism, colourless
V = 1385.1 (2) Å3	0.42 × 0.35 × 0.13 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	2049 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.104
graphite	θmax = 66.9°, θmin = 3.9°
ω/2θ scans	h = −7→2
Absorption correction: ψ scan (North et al., 1968)	k = −10→0
Tmin = 0.140, Tmax = 0.482	l = −27→27
3363 measured reflections	3 standard reflections every 120 min
2424 independent reflections	intensity decay: 1.0%

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) = 0.236	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ2(Fo2) + (0.1586P)2 + 1.125P] where P = (Fo2 + 2Fc2)/3
2424 reflections	(Δ/σ)max = 0.011
176 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.64 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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	0.6639 (6)	0.0125 (4)	0.60350 (17)	0.0403 (9)
C2	0.4841 (6)	0.0772 (5)	0.61451 (17)	0.0442 (9)
H2	0.4215	0.1394	0.5872	0.053*
C3	0.3986 (6)	0.0473 (5)	0.66742 (18)	0.0441 (9)
C4	0.4832 (7)	−0.0443 (5)	0.70890 (18)	0.0470 (10)
H4	0.4223	−0.0636	0.7439	0.056*
C5	0.6627 (7)	−0.1064 (5)	0.69595 (19)	0.0496 (10)
C6	0.7556 (7)	−0.0807 (5)	0.64425 (18)	0.0454 (9)
H6	0.8771	−0.1249	0.6369	0.054*
C7	0.9133 (6)	0.3137 (4)	0.54905 (17)	0.0393 (9)
C8	1.1092 (6)	0.3369 (5)	0.53436 (18)	0.0430 (9)
H8	1.1630	0.2845	0.5036	0.052*
C9	1.2229 (7)	0.4380 (5)	0.56558 (19)	0.0495 (10)
H9	1.3544	0.4532	0.5560	0.059*
C10	1.1436 (8)	0.5185 (5)	0.6117 (2)	0.0522 (11)
C11	0.9505 (8)	0.4940 (6)	0.62479 (19)	0.0547 (11)
H11	0.8965	0.5466	0.6554	0.066*
C12	0.8329 (7)	0.3936 (5)	0.59400 (18)	0.0476 (10)
H12	0.7010	0.3799	0.6034	0.057*
C13	1.2739 (10)	0.6246 (7)	0.6464 (2)	0.0714 (15)
H13A	1.2902	0.7152	0.6248	0.086*
H13B	1.4014	0.5795	0.6540	0.086*
H13C	1.2133	0.6468	0.6827	0.086*
N1	0.7620 (6)	0.0309 (4)	0.55009 (16)	0.0467 (9)
H1N	0.872 (8)	−0.020 (6)	0.549 (2)	0.056*
O1	0.8754 (5)	0.1373 (3)	0.46032 (12)	0.0478 (8)
O2	0.5716 (4)	0.2390 (4)	0.50360 (13)	0.0490 (7)
Cl1	0.17240 (18)	0.13146 (17)	0.68157 (5)	0.0653 (5)
Cl2	0.7786 (3)	−0.22328 (19)	0.74746 (6)	0.0826 (6)
S1	0.76828 (14)	0.18214 (11)	0.51047 (4)	0.0392 (4)

	U11	U22	U33	U12	U13	U23
C1	0.049 (2)	0.0334 (18)	0.039 (2)	−0.0094 (16)	0.0126 (16)	−0.0055 (15)
C2	0.051 (2)	0.042 (2)	0.040 (2)	−0.0025 (17)	0.0062 (17)	0.0030 (17)
C3	0.044 (2)	0.045 (2)	0.044 (2)	0.0012 (16)	0.0111 (17)	−0.0025 (18)
C4	0.061 (3)	0.042 (2)	0.038 (2)	−0.0064 (18)	0.0116 (18)	−0.0019 (17)
C5	0.067 (3)	0.039 (2)	0.044 (2)	0.0051 (19)	0.0065 (19)	0.0027 (18)
C6	0.053 (2)	0.041 (2)	0.043 (2)	0.0065 (17)	0.0083 (17)	−0.0036 (17)
C7	0.046 (2)	0.039 (2)	0.0330 (18)	0.0042 (16)	0.0065 (15)	0.0040 (15)
C8	0.048 (2)	0.041 (2)	0.040 (2)	0.0033 (17)	0.0104 (17)	0.0008 (17)
C9	0.052 (3)	0.047 (2)	0.049 (2)	−0.0016 (18)	0.0036 (19)	0.0065 (19)
C10	0.072 (3)	0.040 (2)	0.045 (2)	−0.001 (2)	−0.003 (2)	0.0070 (19)
C11	0.078 (3)	0.050 (2)	0.037 (2)	0.006 (2)	0.008 (2)	−0.0056 (18)
C12	0.055 (3)	0.046 (2)	0.042 (2)	0.0047 (18)	0.0138 (18)	−0.0040 (18)
C13	0.089 (4)	0.068 (3)	0.056 (3)	−0.008 (3)	−0.014 (3)	−0.004 (3)
N1	0.055 (2)	0.0387 (18)	0.047 (2)	0.0038 (15)	0.0219 (17)	0.0029 (15)
O1	0.0598 (18)	0.0507 (17)	0.0337 (14)	0.0098 (13)	0.0148 (12)	−0.0022 (12)
O2	0.0481 (17)	0.0543 (18)	0.0446 (16)	0.0038 (13)	0.0051 (12)	0.0002 (14)
Cl1	0.0525 (7)	0.0842 (9)	0.0604 (7)	0.0132 (6)	0.0205 (5)	0.0067 (6)
Cl2	0.1076 (12)	0.0872 (10)	0.0542 (8)	0.0448 (9)	0.0193 (7)	0.0235 (7)
S1	0.0456 (6)	0.0388 (6)	0.0338 (6)	0.0031 (4)	0.0110 (4)	−0.0010 (4)

C1—C2	1.374 (6)	C8—H8	0.9300
C1—C6	1.384 (6)	C9—C10	1.399 (7)
C1—N1	1.420 (5)	C9—H9	0.9300
C2—C3	1.387 (5)	C10—C11	1.362 (7)
C2—H2	0.9300	C10—C13	1.506 (7)
C3—C4	1.368 (6)	C11—C12	1.379 (7)
C3—Cl1	1.740 (4)	C11—H11	0.9300
C4—C5	1.373 (6)	C12—H12	0.9300
C4—H4	0.9300	C13—H13A	0.9600
C5—C6	1.378 (6)	C13—H13B	0.9600
C5—Cl2	1.746 (5)	C13—H13C	0.9600
C6—H6	0.9300	N1—S1	1.633 (4)
C7—C12	1.380 (6)	N1—H1N	0.87 (5)
C7—C8	1.389 (6)	O1—S1	1.435 (3)
C7—S1	1.753 (4)	O2—S1	1.424 (3)
C8—C9	1.374 (6)
C2—C1—C6	120.5 (4)	C10—C9—H9	119.5
C2—C1—N1	123.1 (4)	C11—C10—C9	118.3 (4)
C6—C1—N1	116.3 (4)	C11—C10—C13	122.0 (5)
C1—C2—C3	118.2 (4)	C9—C10—C13	119.7 (5)
C1—C2—H2	120.9	C10—C11—C12	121.9 (4)
C3—C2—H2	120.9	C10—C11—H11	119.0
C4—C3—C2	123.3 (4)	C12—C11—H11	119.0
C4—C3—Cl1	118.6 (3)	C11—C12—C7	119.3 (4)
C2—C3—Cl1	118.1 (3)	C11—C12—H12	120.4
C3—C4—C5	116.3 (4)	C7—C12—H12	120.4
C3—C4—H4	121.8	C10—C13—H13A	109.5
C5—C4—H4	121.8	C10—C13—H13B	109.5
C4—C5—C6	123.1 (4)	H13A—C13—H13B	109.5
C4—C5—Cl2	118.4 (3)	C10—C13—H13C	109.5
C6—C5—Cl2	118.5 (3)	H13A—C13—H13C	109.5
C5—C6—C1	118.5 (4)	H13B—C13—H13C	109.5
C5—C6—H6	120.7	C1—N1—S1	126.7 (3)
C1—C6—H6	120.7	C1—N1—H1N	113 (4)
C12—C7—C8	120.1 (4)	S1—N1—H1N	112 (4)
C12—C7—S1	120.0 (3)	O2—S1—O1	120.10 (18)
C8—C7—S1	119.8 (3)	O2—S1—N1	108.55 (19)
C9—C8—C7	119.4 (4)	O1—S1—N1	103.68 (17)
C9—C8—H8	120.3	O2—S1—C7	108.50 (19)
C7—C8—H8	120.3	O1—S1—C7	107.86 (19)
C8—C9—C10	120.9 (4)	N1—S1—C7	107.5 (2)
C8—C9—H9	119.5
C6—C1—C2—C3	0.3 (6)	C9—C10—C11—C12	−0.2 (7)
N1—C1—C2—C3	177.7 (4)	C13—C10—C11—C12	−178.1 (5)
C1—C2—C3—C4	−0.6 (7)	C10—C11—C12—C7	0.9 (7)
C1—C2—C3—Cl1	179.2 (3)	C8—C7—C12—C11	−1.4 (6)
C2—C3—C4—C5	0.6 (7)	S1—C7—C12—C11	178.5 (3)
Cl1—C3—C4—C5	−179.1 (3)	C2—C1—N1—S1	37.0 (6)
C3—C4—C5—C6	−0.4 (7)	C6—C1—N1—S1	−145.5 (4)
C3—C4—C5—Cl2	179.6 (3)	C1—N1—S1—O2	−47.9 (4)
C4—C5—C6—C1	0.2 (7)	C1—N1—S1—O1	−176.6 (4)
Cl2—C5—C6—C1	−179.8 (3)	C1—N1—S1—C7	69.3 (4)
C2—C1—C6—C5	−0.2 (6)	C12—C7—S1—O2	37.9 (4)
N1—C1—C6—C5	−177.7 (4)	C8—C7—S1—O2	−142.2 (3)
C12—C7—C8—C9	1.1 (6)	C12—C7—S1—O1	169.5 (3)
S1—C7—C8—C9	−178.7 (3)	C8—C7—S1—O1	−10.7 (4)
C7—C8—C9—C10	−0.4 (6)	C12—C7—S1—N1	−79.3 (4)
C8—C9—C10—C11	0.0 (7)	C8—C7—S1—N1	100.6 (3)
C8—C9—C10—C13	177.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.87 (5)	2.02 (6)	2.888 (5)	176 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.87 (5)	2.02 (6)	2.888 (5)	176 (5)

Symmetry code: (i) .