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

In 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 has gauche torsions with respect to the S=O bonds. The mol-ecule is bent at the S atom with a C-SO(2)-NH-C torsion angle of 64.3 (4)°. Furthermore, the conformation of the N-H bond and the meta-chloro group in the adjacent benzene ring are anti to each other. The two benzene rings are tilted relative to each other by 82.5 (1)°. In the crystal, mol-ecules are linked by pairs of N-H⋯O(S) hydrogen bonds, forming inversion dimers.

Related literature

For our study of the effect of substituents on the structures of N-(ar­yl)aryl­sulfonamides, see: Gowda et al. (2009 ▶); Shakuntala et al. (2010 ▶, 2011 ▶); For related structures, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C13H11Cl2NO2S

M = 316.19

Monoclinic,

a = 9.543 (1) Å

b = 13.628 (2) Å

c = 10.893 (1) Å

β = 94.85 (1)°

V = 1411.6 (3) Å3

Z = 4

Cu Kα radiation

μ = 5.50 mm−1

T = 299 K

0.40 × 0.28 × 0.18 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.217, T max = 0.438

2927 measured reflections

2462 independent reflections

1791 reflections with I > 2σ(I)

R int = 0.117

3 standard reflections every 120 min intensity decay: 1.0%

Refinement

R[F 2 > 2σ(F 2)] = 0.086

wR(F 2) = 0.236

S = 1.03

2462 reflections

176 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.97 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/S1600536810051305/ds2077sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051305/ds2077Isup2.hkl

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

C13H11Cl2NO2S	F(000) = 648
Mr = 316.19	Dx = 1.488 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 9.543 (1) Å	θ = 5.7–18.6°
b = 13.628 (2) Å	µ = 5.50 mm−1
c = 10.893 (1) Å	T = 299 K
β = 94.85 (1)°	Prism, light brown
V = 1411.6 (3) Å3	0.40 × 0.28 × 0.18 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	1791 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.117
graphite	θmax = 66.9°, θmin = 4.7°
ω/2θ scans	h = −11→2
Absorption correction: ψ scan (North et al., 1968)	k = −16→0
Tmin = 0.217, Tmax = 0.438	l = −13→13
2927 measured reflections	3 standard reflections every 120 min
2462 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)] = 0.086	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.236	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.1697P)2 + 0.0915P] where P = (Fo2 + 2Fc2)/3
2462 reflections	(Δ/σ)max < 0.001
176 parameters	Δρmax = 0.38 e Å−3
1 restraint	Δρmin = −0.97 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	0.8141 (4)	0.4519 (3)	0.0796 (4)	0.0606 (10)
C2	0.7845 (5)	0.3933 (4)	−0.0224 (5)	0.0831 (15)
H2	0.7044	0.4049	−0.0751	0.100*
C3	0.8723 (6)	0.3186 (4)	−0.0457 (6)	0.0875 (15)
H3	0.8519	0.2801	−0.1154	0.105*
C4	0.9909 (5)	0.2983 (4)	0.0311 (5)	0.0800 (14)
C5	1.0181 (6)	0.3562 (6)	0.1314 (6)	0.103 (2)
H5	1.0970	0.3433	0.1851	0.124*
C6	0.9322 (5)	0.4336 (5)	0.1561 (6)	0.0953 (18)
H6	0.9544	0.4733	0.2245	0.114*
C7	0.5844 (4)	0.4522 (3)	0.2993 (4)	0.0572 (9)
C8	0.6858 (5)	0.4779 (3)	0.3929 (4)	0.0654 (11)
H8	0.7506	0.5271	0.3806	0.079*
C9	0.6891 (5)	0.4292 (3)	0.5048 (4)	0.0640 (10)
C10	0.5946 (5)	0.3574 (4)	0.5250 (4)	0.0684 (11)
C11	0.4920 (5)	0.3339 (4)	0.4311 (5)	0.0769 (13)
H11	0.4256	0.2859	0.4438	0.092*
C12	0.4885 (4)	0.3809 (3)	0.3209 (4)	0.0648 (11)
H12	0.4195	0.3644	0.2589	0.078*
C13	1.0877 (7)	0.2150 (5)	0.0040 (8)	0.118 (3)
H13A	1.1115	0.2196	−0.0796	0.142*
H13B	1.0414	0.1536	0.0158	0.142*
H13C	1.1719	0.2187	0.0587	0.142*
N1	0.5735 (4)	0.4999 (3)	0.1825 (4)	0.0644 (9)
H1N	0.515 (4)	0.467 (3)	0.139 (4)	0.077*
O1	0.7751 (4)	0.6143 (3)	0.1958 (3)	0.0814 (10)
O2	0.6338 (3)	0.5836 (2)	−0.0009 (3)	0.0746 (9)
Cl1	0.81491 (16)	0.46318 (12)	0.61972 (13)	0.0981 (6)
Cl2	0.59783 (18)	0.29657 (12)	0.66355 (13)	0.1038 (6)
S1	0.70098 (11)	0.54753 (8)	0.11309 (10)	0.0632 (4)

	U11	U22	U33	U12	U13	U23
C1	0.051 (2)	0.076 (3)	0.053 (2)	−0.0054 (18)	−0.0029 (16)	0.0103 (19)
C2	0.075 (3)	0.095 (3)	0.075 (3)	0.018 (3)	−0.019 (2)	−0.017 (3)
C3	0.090 (3)	0.088 (3)	0.084 (4)	0.013 (3)	0.000 (3)	−0.011 (3)
C4	0.069 (3)	0.083 (3)	0.090 (4)	0.009 (2)	0.018 (2)	0.023 (3)
C5	0.069 (3)	0.149 (6)	0.088 (4)	0.034 (3)	−0.016 (3)	−0.001 (4)
C6	0.063 (3)	0.141 (5)	0.077 (4)	0.017 (3)	−0.018 (2)	−0.019 (3)
C7	0.054 (2)	0.065 (2)	0.053 (2)	0.0078 (17)	0.0068 (16)	−0.0095 (18)
C8	0.062 (2)	0.071 (3)	0.062 (3)	−0.0084 (19)	−0.0018 (18)	−0.002 (2)
C9	0.064 (2)	0.070 (3)	0.057 (2)	0.004 (2)	0.0003 (18)	−0.008 (2)
C10	0.078 (3)	0.072 (3)	0.057 (2)	−0.003 (2)	0.018 (2)	−0.005 (2)
C11	0.072 (3)	0.086 (3)	0.076 (3)	−0.016 (2)	0.020 (2)	−0.012 (3)
C12	0.055 (2)	0.083 (3)	0.057 (2)	−0.004 (2)	0.0075 (17)	−0.015 (2)
C13	0.102 (4)	0.108 (5)	0.151 (7)	0.037 (4)	0.043 (4)	0.032 (4)
N1	0.0579 (19)	0.073 (2)	0.061 (2)	−0.0018 (16)	0.0008 (15)	0.0013 (18)
O1	0.094 (2)	0.078 (2)	0.072 (2)	−0.0218 (17)	0.0003 (17)	−0.0074 (17)
O2	0.0768 (19)	0.077 (2)	0.068 (2)	0.0037 (15)	−0.0080 (15)	0.0107 (16)
Cl1	0.0977 (10)	0.1188 (12)	0.0725 (9)	−0.0217 (8)	−0.0235 (7)	0.0056 (7)
Cl2	0.1393 (13)	0.1090 (11)	0.0655 (8)	−0.0192 (9)	0.0224 (8)	0.0143 (7)
S1	0.0652 (6)	0.0664 (7)	0.0567 (6)	−0.0025 (4)	−0.0028 (4)	0.0024 (5)

C1—C6	1.366 (6)	C8—H8	0.9300
C1—C2	1.378 (7)	C9—C10	1.361 (6)
C1—S1	1.751 (5)	C9—Cl1	1.723 (4)
C2—C3	1.356 (7)	C10—C11	1.392 (7)
C2—H2	0.9300	C10—Cl2	1.720 (5)
C3—C4	1.377 (8)	C11—C12	1.359 (7)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.355 (8)	C12—H12	0.9300
C4—C13	1.509 (7)	C13—H13A	0.9600
C5—C6	1.377 (8)	C13—H13B	0.9600
C5—H5	0.9300	C13—H13C	0.9600
C6—H6	0.9300	N1—S1	1.621 (4)
C7—C12	1.368 (6)	N1—H1N	0.83 (3)
C7—C8	1.390 (6)	O1—S1	1.426 (3)
C7—N1	1.425 (6)	O2—S1	1.435 (3)
C8—C9	1.385 (6)
C6—C1—C2	119.3 (5)	C8—C9—Cl1	118.2 (4)
C6—C1—S1	120.0 (4)	C9—C10—C11	118.7 (4)
C2—C1—S1	120.7 (3)	C9—C10—Cl2	121.7 (4)
C3—C2—C1	119.9 (5)	C11—C10—Cl2	119.6 (4)
C3—C2—H2	120.1	C12—C11—C10	120.3 (4)
C1—C2—H2	120.1	C12—C11—H11	119.9
C2—C3—C4	121.7 (6)	C10—C11—H11	119.9
C2—C3—H3	119.1	C11—C12—C7	121.3 (4)
C4—C3—H3	119.1	C11—C12—H12	119.4
C5—C4—C3	117.7 (5)	C7—C12—H12	119.4
C5—C4—C13	121.1 (6)	C4—C13—H13A	109.5
C3—C4—C13	121.2 (6)	C4—C13—H13B	109.5
C4—C5—C6	121.8 (5)	H13A—C13—H13B	109.5
C4—C5—H5	119.1	C4—C13—H13C	109.5
C6—C5—H5	119.1	H13A—C13—H13C	109.5
C1—C6—C5	119.6 (5)	H13B—C13—H13C	109.5
C1—C6—H6	120.2	C7—N1—S1	126.8 (3)
C5—C6—H6	120.2	C7—N1—H1N	105 (4)
C12—C7—C8	119.1 (4)	S1—N1—H1N	116 (4)
C12—C7—N1	118.5 (4)	O1—S1—O2	119.3 (2)
C8—C7—N1	122.3 (4)	O1—S1—N1	108.2 (2)
C9—C8—C7	119.2 (4)	O2—S1—N1	104.04 (19)
C9—C8—H8	120.4	O1—S1—C1	109.0 (2)
C7—C8—H8	120.4	O2—S1—C1	108.3 (2)
C10—C9—C8	121.4 (4)	N1—S1—C1	107.4 (2)
C10—C9—Cl1	120.4 (4)
C6—C1—C2—C3	−0.1 (9)	Cl1—C9—C10—Cl2	−1.0 (6)
S1—C1—C2—C3	−179.0 (5)	C9—C10—C11—C12	1.2 (7)
C1—C2—C3—C4	0.9 (10)	Cl2—C10—C11—C12	−179.7 (4)
C2—C3—C4—C5	−0.4 (9)	C10—C11—C12—C7	−0.2 (7)
C2—C3—C4—C13	180.0 (6)	C8—C7—C12—C11	−1.1 (6)
C3—C4—C5—C6	−0.8 (9)	N1—C7—C12—C11	−179.0 (4)
C13—C4—C5—C6	178.8 (6)	C12—C7—N1—S1	−151.4 (3)
C2—C1—C6—C5	−1.1 (9)	C8—C7—N1—S1	30.8 (6)
S1—C1—C6—C5	177.8 (5)	C7—N1—S1—O1	−53.2 (4)
C4—C5—C6—C1	1.6 (10)	C7—N1—S1—O2	178.9 (4)
C12—C7—C8—C9	1.4 (6)	C7—N1—S1—C1	64.3 (4)
N1—C7—C8—C9	179.2 (4)	C6—C1—S1—O1	19.7 (5)
C7—C8—C9—C10	−0.4 (7)	C2—C1—S1—O1	−161.4 (4)
C7—C8—C9—Cl1	−179.4 (3)	C6—C1—S1—O2	150.9 (4)
C8—C9—C10—C11	−0.8 (7)	C2—C1—S1—O2	−30.2 (5)
Cl1—C9—C10—C11	178.2 (4)	C6—C1—S1—N1	−97.4 (5)
C8—C9—C10—Cl2	−180.0 (4)	C2—C1—S1—N1	81.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.83 (3)	2.10 (3)	2.908 (5)	166 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.83 (3)	2.10 (3)	2.908 (5)	166 (5)

Symmetry code: (i) .