2,4-Dichloro-N-(2-chloro-phen-yl)benzene-sulfonamide.

In the title compound, C(12)H(8)Cl(3)NO(2)S, the conformation of the N-H bond in the C-SO(2)-NH-C segment is syn to the ortho-Cl in the aniline ring. The dihedral angle between the two benzene rings is 74.3 (1)°. An intra-molecular N-H⋯Cl hydrogen bond occurs. In the crystal, pairs of N-H⋯O hydrogen bonds link the mol-ecules into dimers.

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. (2010 ▶); Nirmala et al. (2010 ▶). For related structures, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C12H8Cl3NO2S

M = 336.60

Orthorhombic,

a = 10.5639 (8) Å

b = 16.279 (1) Å

c = 16.693 (1) Å

V = 2870.7 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.78 mm−1

T = 299 K

0.30 × 0.24 × 0.22 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.800, T max = 0.847

8054 measured reflections

2938 independent reflections

2054 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.107

S = 1.01

2938 reflections

175 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.35 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/S1600536810021306/bq2220sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810021306/bq2220Isup2.hkl

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

C12H8Cl3NO2S	F(000) = 1360
Mr = 336.60	Dx = 1.558 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 2957 reflections
a = 10.5639 (8) Å	θ = 2.5–27.8°
b = 16.279 (1) Å	µ = 0.78 mm−1
c = 16.693 (1) Å	T = 299 K
V = 2870.7 (3) Å3	Prism, colourless
Z = 8	0.30 × 0.24 × 0.22 mm

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2938 independent reflections
Radiation source: fine-focus sealed tube	2054 reflections with I > 2σ(I)
graphite	Rint = 0.019
Rotation method data acquisition using ω and phi scans	θmax = 26.4°, θmin = 2.5°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −9→13
Tmin = 0.800, Tmax = 0.847	k = −14→20
8054 measured reflections	l = −11→20

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0458P)2 + 1.5152P] where P = (Fo2 + 2Fc2)/3
2938 reflections	(Δ/σ)max < 0.001
175 parameters	Δρmax = 0.36 e Å−3
1 restraint	Δρmin = −0.35 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	0.3134 (2)	0.61639 (15)	0.32900 (15)	0.0497 (6)
C2	0.2866 (3)	0.53340 (17)	0.31598 (16)	0.0579 (7)
C3	0.3728 (3)	0.47403 (19)	0.3366 (2)	0.0753 (9)
H3	0.3545	0.4188	0.3282	0.090*
C4	0.4862 (3)	0.4967 (2)	0.3697 (2)	0.0850 (10)
C5	0.5150 (3)	0.5775 (2)	0.3827 (2)	0.0919 (11)
H5	0.5923	0.5920	0.4052	0.110*
C6	0.4285 (3)	0.6371 (2)	0.36218 (19)	0.0713 (8)
H6	0.4480	0.6921	0.3708	0.086*
C7	0.0989 (2)	0.68618 (15)	0.45102 (14)	0.0477 (6)
C8	0.0161 (2)	0.63852 (15)	0.49537 (15)	0.0509 (6)
C9	0.0238 (3)	0.63637 (17)	0.57821 (16)	0.0664 (8)
H9	−0.0334	0.6050	0.6076	0.080*
C10	0.1164 (3)	0.68083 (19)	0.61698 (17)	0.0730 (9)
H10	0.1232	0.6786	0.6725	0.088*
C11	0.1978 (3)	0.7281 (2)	0.57371 (17)	0.0703 (8)
H11	0.2600	0.7581	0.6000	0.084*
C12	0.1892 (3)	0.73195 (18)	0.49182 (16)	0.0629 (7)
H12	0.2444	0.7655	0.4633	0.075*
N1	0.08883 (19)	0.68827 (15)	0.36630 (12)	0.0542 (6)
H1N	0.0212 (16)	0.6693 (15)	0.3452 (15)	0.065*
O1	0.15449 (18)	0.68354 (12)	0.22707 (9)	0.0648 (5)
O2	0.27286 (18)	0.77149 (11)	0.32041 (12)	0.0675 (5)
Cl1	0.14598 (8)	0.50245 (5)	0.27304 (6)	0.0914 (3)
Cl2	0.59587 (12)	0.42218 (8)	0.39456 (10)	0.1453 (5)
Cl3	−0.09873 (7)	0.58020 (5)	0.44734 (5)	0.0691 (2)
S1	0.20683 (6)	0.69660 (4)	0.30490 (4)	0.05119 (19)

	U11	U22	U33	U12	U13	U23
C1	0.0463 (14)	0.0562 (15)	0.0466 (14)	−0.0060 (12)	0.0030 (11)	0.0018 (12)
C2	0.0561 (16)	0.0593 (16)	0.0584 (16)	−0.0085 (14)	0.0062 (13)	−0.0016 (13)
C3	0.082 (2)	0.0563 (17)	0.087 (2)	0.0018 (17)	0.0103 (18)	0.0005 (17)
C4	0.075 (2)	0.083 (2)	0.097 (3)	0.024 (2)	−0.0010 (19)	0.006 (2)
C5	0.0572 (19)	0.099 (3)	0.119 (3)	0.0074 (19)	−0.0242 (18)	−0.003 (2)
C6	0.0537 (17)	0.0678 (19)	0.092 (2)	−0.0065 (15)	−0.0125 (16)	−0.0029 (17)
C7	0.0517 (14)	0.0510 (14)	0.0403 (13)	0.0108 (12)	−0.0058 (11)	−0.0019 (11)
C8	0.0630 (16)	0.0433 (13)	0.0463 (14)	0.0131 (12)	−0.0027 (12)	0.0000 (12)
C9	0.093 (2)	0.0583 (17)	0.0482 (16)	0.0183 (17)	0.0063 (15)	0.0079 (14)
C10	0.110 (3)	0.069 (2)	0.0401 (15)	0.0277 (19)	−0.0159 (16)	−0.0087 (15)
C11	0.086 (2)	0.0712 (19)	0.0535 (17)	0.0103 (17)	−0.0189 (15)	−0.0123 (15)
C12	0.0659 (17)	0.0709 (19)	0.0518 (16)	−0.0033 (15)	−0.0088 (13)	−0.0053 (14)
N1	0.0456 (12)	0.0765 (16)	0.0404 (11)	−0.0022 (11)	−0.0071 (9)	−0.0013 (11)
O1	0.0674 (11)	0.0888 (14)	0.0382 (9)	−0.0078 (11)	−0.0027 (8)	0.0105 (9)
O2	0.0745 (13)	0.0518 (10)	0.0763 (13)	−0.0140 (10)	−0.0064 (10)	0.0104 (10)
Cl1	0.0830 (6)	0.0772 (5)	0.1140 (7)	−0.0306 (5)	−0.0171 (5)	−0.0062 (5)
Cl2	0.1218 (9)	0.1269 (10)	0.1873 (13)	0.0642 (8)	−0.0140 (9)	0.0199 (9)
Cl3	0.0743 (5)	0.0665 (5)	0.0665 (5)	−0.0100 (4)	−0.0044 (4)	0.0089 (4)
S1	0.0528 (4)	0.0574 (4)	0.0434 (3)	−0.0060 (3)	−0.0025 (3)	0.0086 (3)

C1—C6	1.379 (3)	C7—N1	1.419 (3)
C1—C2	1.397 (3)	C8—C9	1.386 (4)
C1—S1	1.770 (3)	C8—Cl3	1.737 (3)
C2—C3	1.372 (4)	C9—C10	1.378 (4)
C2—Cl1	1.725 (3)	C9—H9	0.9300
C3—C4	1.369 (5)	C10—C11	1.361 (4)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.367 (5)	C11—C12	1.372 (4)
C4—Cl2	1.728 (3)	C11—H11	0.9300
C5—C6	1.377 (4)	C12—H12	0.9300
C5—H5	0.9300	N1—S1	1.620 (2)
C6—H6	0.9300	N1—H1N	0.855 (10)
C7—C8	1.383 (4)	O1—S1	1.4279 (17)
C7—C12	1.389 (3)	O2—S1	1.4282 (18)
C6—C1—C2	118.5 (3)	C9—C8—Cl3	119.2 (2)
C6—C1—S1	118.1 (2)	C10—C9—C8	119.8 (3)
C2—C1—S1	123.3 (2)	C10—C9—H9	120.1
C3—C2—C1	120.5 (3)	C8—C9—H9	120.1
C3—C2—Cl1	118.1 (2)	C11—C10—C9	119.7 (3)
C1—C2—Cl1	121.4 (2)	C11—C10—H10	120.1
C4—C3—C2	119.5 (3)	C9—C10—H10	120.1
C4—C3—H3	120.3	C10—C11—C12	120.9 (3)
C2—C3—H3	120.3	C10—C11—H11	119.6
C5—C4—C3	121.2 (3)	C12—C11—H11	119.6
C5—C4—Cl2	119.2 (3)	C11—C12—C7	120.6 (3)
C3—C4—Cl2	119.6 (3)	C11—C12—H12	119.7
C4—C5—C6	119.5 (3)	C7—C12—H12	119.7
C4—C5—H5	120.3	C7—N1—S1	125.13 (17)
C6—C5—H5	120.3	C7—N1—H1N	117.7 (19)
C5—C6—C1	120.8 (3)	S1—N1—H1N	114.3 (19)
C5—C6—H6	119.6	O1—S1—O2	118.76 (12)
C1—C6—H6	119.6	O1—S1—N1	105.39 (11)
C8—C7—C12	118.2 (2)	O2—S1—N1	109.43 (12)
C8—C7—N1	120.0 (2)	O1—S1—C1	110.08 (12)
C12—C7—N1	121.8 (2)	O2—S1—C1	106.14 (12)
C7—C8—C9	120.7 (3)	N1—S1—C1	106.48 (12)
C7—C8—Cl3	120.06 (19)
C6—C1—C2—C3	0.7 (4)	Cl3—C8—C9—C10	178.5 (2)
S1—C1—C2—C3	−179.4 (2)	C8—C9—C10—C11	1.5 (4)
C6—C1—C2—Cl1	−178.8 (2)	C9—C10—C11—C12	−0.2 (5)
S1—C1—C2—Cl1	1.1 (3)	C10—C11—C12—C7	−1.5 (4)
C1—C2—C3—C4	−0.4 (5)	C8—C7—C12—C11	1.7 (4)
Cl1—C2—C3—C4	179.0 (3)	N1—C7—C12—C11	−179.2 (3)
C2—C3—C4—C5	0.1 (5)	C8—C7—N1—S1	−145.6 (2)
C2—C3—C4—Cl2	−179.1 (2)	C12—C7—N1—S1	35.3 (4)
C3—C4—C5—C6	0.0 (6)	C7—N1—S1—O1	171.4 (2)
Cl2—C4—C5—C6	179.3 (3)	C7—N1—S1—O2	−59.8 (2)
C4—C5—C6—C1	0.2 (5)	C7—N1—S1—C1	54.5 (2)
C2—C1—C6—C5	−0.5 (4)	C6—C1—S1—O1	134.6 (2)
S1—C1—C6—C5	179.6 (3)	C2—C1—S1—O1	−45.3 (2)
C12—C7—C8—C9	−0.3 (4)	C6—C1—S1—O2	4.9 (2)
N1—C7—C8—C9	−179.4 (2)	C2—C1—S1—O2	−175.0 (2)
C12—C7—C8—Cl3	179.94 (19)	C6—C1—S1—N1	−111.6 (2)
N1—C7—C8—Cl3	0.8 (3)	C2—C1—S1—N1	68.5 (2)
C7—C8—C9—C10	−1.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.86 (1)	2.23 (2)	3.007 (3)	152 (2)
N1—H1N···Cl3	0.86 (1)	2.57 (3)	2.975 (2)	110 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.86 (1)	2.23 (2)	3.007 (3)	152 (2)
N1—H1N⋯Cl3	0.86 (1)	2.57 (3)	2.975 (2)	110 (2)

Symmetry code: (i) .