4-Chloro-N-(3-chloro-phen-yl)-2-methyl-benzene-sulfonamide.

In the title compound, C(13)H(11)Cl(2)NO(2)S, the conformation of the N-H bond in the C-SO(2)-NH-C segment is anti to the meta-Cl atom on the aniline ring and syn to the ortho-methyl group on the sulfonyl-benzene ring. Furthermore, the torsion angle of the C-SO(2)-NH-C segment in the mol-ecule is 80.1 (3)°. The two benzene rings are tilted relative to each other by 70.9 (1)°. In the crystal, pairs of inter-molecular N-H⋯O hydrogen bonds link the mol-ecules via inversion-related dimers into infinite column-like chains.

Related literature

For the preparation of the title compound, see: Savitha & Gowda (2006 ▶). For our studies of the effect of substituents on the structures of N-(ar­yl)aryl­sulfonamides, see: Gowda et al. (2008 ▶, 2009 ▶). For related structures, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C13H11Cl2NO2S

M = 316.19

Monoclinic,

a = 7.9757 (7) Å

b = 11.3472 (8) Å

c = 15.569 (1) Å

β = 91.490 (8)°

V = 1408.55 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.61 mm−1

T = 299 K

0.36 × 0.28 × 0.04 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.812, T max = 0.976

5849 measured reflections

2866 independent reflections

1853 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.161

S = 1.04

2866 reflections

176 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.52 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; 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/S1600536810022968/vm2031sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810022968/vm2031Isup2.hkl

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

C13H11Cl2NO2S	F(000) = 648
Mr = 316.19	Dx = 1.491 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2107 reflections
a = 7.9757 (7) Å	θ = 2.6–27.8°
b = 11.3472 (8) Å	µ = 0.61 mm−1
c = 15.569 (1) Å	T = 299 K
β = 91.490 (8)°	Plate, colourless
V = 1408.55 (18) Å3	0.36 × 0.28 × 0.04 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2866 independent reflections
Radiation source: fine-focus sealed tube	1853 reflections with I > 2σ(I)
graphite	Rint = 0.017
Rotation method data acquisition using ω and phi scans	θmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −9→7
Tmin = 0.812, Tmax = 0.976	k = −14→14
5849 measured reflections	l = −19→19

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0763P)2 + 0.8836P] where P = (Fo2 + 2Fc2)/3
2866 reflections	(Δ/σ)max = 0.001
176 parameters	Δρmax = 0.43 e Å−3
1 restraint	Δρmin = −0.52 e Å−3

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	0.3431 (4)	0.2031 (3)	0.66150 (19)	0.0451 (7)
C2	0.3719 (5)	0.2761 (3)	0.7319 (2)	0.0571 (9)
H2	0.4793	0.2818	0.7563	0.069*
C3	0.2436 (6)	0.3398 (3)	0.7657 (2)	0.0642 (10)
H3	0.2638	0.3897	0.8122	0.077*
C4	0.0858 (5)	0.3293 (3)	0.7305 (2)	0.0617 (10)
C5	0.0557 (5)	0.2571 (3)	0.6608 (3)	0.0630 (10)
H5	−0.0530	0.2507	0.6383	0.076*
C6	0.1829 (4)	0.1936 (3)	0.6234 (2)	0.0508 (8)
C7	0.6346 (4)	0.2765 (3)	0.5046 (2)	0.0486 (8)
C8	0.6426 (4)	0.3741 (3)	0.5575 (2)	0.0543 (8)
H8	0.5940	0.3729	0.6111	0.065*
C9	0.7240 (5)	0.4732 (3)	0.5292 (2)	0.0585 (9)
C10	0.7951 (6)	0.4781 (4)	0.4506 (3)	0.0809 (13)
H10	0.8492	0.5459	0.4325	0.097*
C11	0.7847 (6)	0.3796 (4)	0.3983 (3)	0.0887 (15)
H11	0.8319	0.3815	0.3444	0.106*
C12	0.7061 (5)	0.2795 (4)	0.4249 (2)	0.0641 (10)
H12	0.7007	0.2137	0.3893	0.077*
C13	0.1457 (5)	0.1168 (3)	0.5412 (2)	0.0595 (10)
H13A	0.1807	0.0371	0.5519	0.071*
H13B	0.2060	0.1481	0.4937	0.071*
H13C	0.0276	0.1182	0.5276	0.071*
N1	0.5495 (4)	0.1719 (3)	0.5270 (2)	0.0640 (9)
H1N	0.539 (5)	0.120 (3)	0.488 (2)	0.077*
O1	0.6571 (3)	0.1510 (2)	0.67778 (17)	0.0697 (7)
O2	0.4690 (3)	0.0031 (2)	0.61100 (16)	0.0660 (7)
Cl1	−0.0771 (2)	0.41129 (13)	0.77137 (10)	0.1162 (6)
Cl2	0.73479 (16)	0.59549 (9)	0.59594 (8)	0.0858 (4)
S1	0.51639 (11)	0.12421 (7)	0.62307 (6)	0.0533 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0512 (19)	0.0407 (16)	0.0432 (17)	−0.0108 (14)	0.0010 (14)	0.0041 (13)
C2	0.062 (2)	0.061 (2)	0.0488 (19)	−0.0148 (18)	−0.0021 (16)	−0.0027 (17)
C3	0.087 (3)	0.057 (2)	0.049 (2)	−0.011 (2)	0.012 (2)	−0.0088 (17)
C4	0.070 (3)	0.048 (2)	0.068 (2)	−0.0030 (18)	0.023 (2)	0.0086 (18)
C5	0.049 (2)	0.058 (2)	0.082 (3)	−0.0104 (18)	0.0034 (19)	0.012 (2)
C6	0.054 (2)	0.0417 (18)	0.057 (2)	−0.0135 (15)	0.0006 (16)	0.0043 (15)
C7	0.0451 (18)	0.0475 (18)	0.0533 (19)	−0.0033 (15)	0.0043 (15)	0.0037 (15)
C8	0.055 (2)	0.050 (2)	0.058 (2)	−0.0003 (16)	0.0070 (16)	0.0008 (16)
C9	0.059 (2)	0.0453 (19)	0.070 (2)	−0.0021 (17)	−0.0067 (18)	0.0079 (17)
C10	0.098 (3)	0.072 (3)	0.073 (3)	−0.031 (2)	0.002 (2)	0.020 (2)
C11	0.105 (4)	0.100 (4)	0.061 (3)	−0.034 (3)	0.021 (2)	0.010 (3)
C12	0.069 (2)	0.068 (2)	0.055 (2)	−0.010 (2)	0.0066 (19)	−0.0050 (18)
C13	0.056 (2)	0.058 (2)	0.063 (2)	−0.0245 (17)	−0.0249 (17)	−0.0032 (17)
N1	0.084 (2)	0.0510 (18)	0.0578 (19)	−0.0174 (16)	0.0191 (16)	−0.0079 (14)
O1	0.0540 (15)	0.0750 (18)	0.0794 (18)	−0.0031 (13)	−0.0104 (13)	0.0085 (14)
O2	0.0826 (19)	0.0420 (13)	0.0738 (17)	−0.0038 (12)	0.0094 (14)	0.0032 (11)
Cl1	0.1189 (12)	0.0990 (10)	0.1336 (12)	0.0235 (8)	0.0566 (10)	0.0030 (8)
Cl2	0.1005 (9)	0.0488 (6)	0.1077 (9)	−0.0067 (5)	−0.0032 (7)	−0.0073 (5)
S1	0.0557 (5)	0.0457 (5)	0.0584 (5)	−0.0046 (4)	0.0028 (4)	0.0040 (4)

C1—C2	1.388 (4)	C8—H8	0.9300
C1—C6	1.399 (5)	C9—C10	1.362 (6)
C1—S1	1.764 (3)	C9—Cl2	1.734 (4)
C2—C3	1.369 (5)	C10—C11	1.384 (6)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.365 (5)	C11—C12	1.366 (5)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.375 (5)	C12—H12	0.9300
C4—Cl1	1.733 (4)	C13—H13A	0.9600
C5—C6	1.386 (5)	C13—H13B	0.9600
C5—H5	0.9300	C13—H13C	0.9600
C6—C13	1.571 (5)	N1—S1	1.619 (3)
C7—C12	1.380 (5)	N1—H1N	0.850 (18)
C7—C8	1.380 (5)	O1—S1	1.424 (3)
C7—N1	1.416 (4)	O2—S1	1.436 (2)
C8—C9	1.377 (5)
C2—C1—C6	120.7 (3)	C8—C9—Cl2	118.5 (3)
C2—C1—S1	117.1 (3)	C9—C10—C11	118.4 (4)
C6—C1—S1	122.1 (2)	C9—C10—H10	120.8
C3—C2—C1	120.6 (3)	C11—C10—H10	120.8
C3—C2—H2	119.7	C12—C11—C10	121.0 (4)
C1—C2—H2	119.7	C12—C11—H11	119.5
C4—C3—C2	119.3 (3)	C10—C11—H11	119.5
C4—C3—H3	120.3	C11—C12—C7	119.7 (4)
C2—C3—H3	120.3	C11—C12—H12	120.1
C3—C4—C5	120.6 (4)	C7—C12—H12	120.1
C3—C4—Cl1	119.9 (3)	C6—C13—H13A	109.5
C5—C4—Cl1	119.5 (3)	C6—C13—H13B	109.5
C4—C5—C6	121.8 (4)	H13A—C13—H13B	109.5
C4—C5—H5	119.1	C6—C13—H13C	109.5
C6—C5—H5	119.1	H13A—C13—H13C	109.5
C5—C6—C1	116.9 (3)	H13B—C13—H13C	109.5
C5—C6—C13	120.4 (3)	C7—N1—S1	126.7 (3)
C1—C6—C13	122.7 (3)	C7—N1—H1N	116 (3)
C12—C7—C8	120.2 (3)	S1—N1—H1N	115 (3)
C12—C7—N1	117.0 (3)	O1—S1—O2	118.89 (17)
C8—C7—N1	122.8 (3)	O1—S1—N1	109.67 (17)
C9—C8—C7	118.7 (3)	O2—S1—N1	104.33 (16)
C9—C8—H8	120.7	O1—S1—C1	107.51 (16)
C7—C8—H8	120.7	O2—S1—C1	108.91 (15)
C10—C9—C8	122.1 (4)	N1—S1—C1	106.97 (16)
C10—C9—Cl2	119.4 (3)
C6—C1—C2—C3	0.4 (5)	C8—C9—C10—C11	−0.2 (7)
S1—C1—C2—C3	−179.7 (3)	Cl2—C9—C10—C11	−179.9 (4)
C1—C2—C3—C4	1.2 (5)	C9—C10—C11—C12	−0.4 (7)
C2—C3—C4—C5	−1.0 (5)	C10—C11—C12—C7	0.5 (7)
C2—C3—C4—Cl1	−178.9 (3)	C8—C7—C12—C11	−0.1 (6)
C3—C4—C5—C6	−0.7 (6)	N1—C7—C12—C11	177.6 (4)
Cl1—C4—C5—C6	177.2 (3)	C12—C7—N1—S1	155.4 (3)
C4—C5—C6—C1	2.1 (5)	C8—C7—N1—S1	−27.0 (5)
C4—C5—C6—C13	−177.0 (3)	C7—N1—S1—O1	−36.2 (4)
C2—C1—C6—C5	−2.0 (5)	C7—N1—S1—O2	−164.6 (3)
S1—C1—C6—C5	178.1 (2)	C7—N1—S1—C1	80.1 (3)
C2—C1—C6—C13	177.2 (3)	C2—C1—S1—O1	2.0 (3)
S1—C1—C6—C13	−2.8 (4)	C6—C1—S1—O1	−178.1 (3)
C12—C7—C8—C9	−0.5 (5)	C2—C1—S1—O2	132.0 (3)
N1—C7—C8—C9	−178.1 (3)	C6—C1—S1—O2	−48.0 (3)
C7—C8—C9—C10	0.6 (6)	C2—C1—S1—N1	−115.7 (3)
C7—C8—C9—Cl2	−179.7 (3)	C6—C1—S1—N1	64.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.85 (2)	2.08 (2)	2.926 (4)	175 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.85 (2)	2.08 (2)	2.926 (4)	175 (4)

Symmetry code: (i) .