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

The mol-ecule of the title compound, C(12)H(8)Cl(3)NO(2)S, is twisted at the S atom, the C-SO(2)-NH-C torsion angle being 67.8 (2)°. The dihedral angle between the two benzene rings is 65.0 (1)°. The crystal structure features inversion dimers linked by pairs of N-H⋯O hydrogen bonds.

Related literature

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

Experimental

Crystal data

C12H8Cl3NO2S

M = 336.60

Triclinic,

a = 6.3925 (9) Å

b = 10.524 (2) Å

c = 11.684 (2) Å

α = 69.51 (1)°

β = 77.96 (1)°

γ = 77.30 (1)°

V = 710.8 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.79 mm−1

T = 299 K

0.40 × 0.40 × 0.30 mm

Data collection

Oxford Diffraction Xcalibur single-crystal X-ray diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.744, T max = 0.798

4462 measured reflections

2873 independent reflections

2514 reflections with I > 2σ(I)

R int = 0.008

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.091

S = 1.04

2873 reflections

175 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.47 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/S1600536810010494/ci5064sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010494/ci5064Isup2.hkl

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

C12H8Cl3NO2S	Z = 2
Mr = 336.60	F(000) = 340
Triclinic, P1	Dx = 1.573 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.3925 (9) Å	Cell parameters from 2802 reflections
b = 10.524 (2) Å	θ = 3.2–27.7°
c = 11.684 (2) Å	µ = 0.79 mm−1
α = 69.51 (1)°	T = 299 K
β = 77.96 (1)°	Prism, colourless
γ = 77.30 (1)°	0.40 × 0.40 × 0.30 mm
V = 710.8 (2) Å3

Oxford Diffraction Xcalibur single-crystal X-ray diffractometer with a Sapphire CCD detector	2873 independent reflections
Radiation source: fine-focus sealed tube	2514 reflections with I > 2σ(I)
graphite	Rint = 0.008
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 3.2°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −7→7
Tmin = 0.744, Tmax = 0.798	k = −13→13
4462 measured reflections	l = −14→12

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0386P)2 + 0.4934P] where P = (Fo2 + 2Fc2)/3
2873 reflections	(Δ/σ)max = 0.001
175 parameters	Δρmax = 0.41 e Å−3
1 restraint	Δρmin = −0.47 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	0.2300 (3)	−0.1157 (2)	0.30386 (18)	0.0362 (4)
C2	0.1233 (3)	−0.1828 (2)	0.25451 (18)	0.0370 (4)
C3	−0.0339 (4)	−0.2602 (2)	0.3281 (2)	0.0449 (5)
H3	−0.1049	−0.3044	0.2949	0.054*
C4	−0.0835 (4)	−0.2707 (2)	0.4523 (2)	0.0504 (5)
C5	0.0190 (4)	−0.2058 (3)	0.5036 (2)	0.0553 (6)
H5	−0.0168	−0.2136	0.5869	0.066*
C6	0.1766 (4)	−0.1286 (2)	0.4290 (2)	0.0477 (5)
H6	0.2472	−0.0850	0.4629	0.057*
C7	0.1442 (3)	0.2193 (2)	0.13604 (18)	0.0357 (4)
C8	0.1996 (3)	0.3448 (2)	0.1231 (2)	0.0430 (5)
H8	0.3429	0.3588	0.0971	0.052*
C9	0.0426 (4)	0.4488 (2)	0.1487 (2)	0.0473 (5)
H9	0.0792	0.5329	0.1397	0.057*
C10	−0.1696 (3)	0.4259 (2)	0.1880 (2)	0.0421 (5)
C11	−0.2275 (3)	0.3009 (2)	0.2035 (2)	0.0420 (5)
H11	−0.3703	0.2865	0.2317	0.050*
C12	−0.0694 (3)	0.1975 (2)	0.17658 (19)	0.0397 (4)
H12	−0.1065	0.1135	0.1857	0.048*
N1	0.3104 (3)	0.11422 (18)	0.10621 (17)	0.0432 (4)
H1N	0.312 (4)	0.100 (3)	0.0395 (18)	0.052*
O1	0.4832 (3)	0.04803 (18)	0.29394 (16)	0.0551 (4)
O2	0.5937 (2)	−0.08756 (17)	0.14887 (15)	0.0529 (4)
Cl1	0.17630 (10)	−0.16945 (7)	0.09860 (5)	0.05343 (17)
Cl2	−0.28179 (14)	−0.36791 (9)	0.54410 (7)	0.0830 (3)
Cl3	−0.36952 (11)	0.55863 (7)	0.21560 (8)	0.0699 (2)
S1	0.42695 (8)	−0.00974 (5)	0.21258 (5)	0.03973 (14)

	U11	U22	U33	U12	U13	U23
C1	0.0351 (10)	0.0349 (10)	0.0358 (10)	−0.0039 (8)	−0.0043 (8)	−0.0094 (8)
C2	0.0393 (10)	0.0357 (10)	0.0334 (10)	−0.0018 (8)	−0.0043 (8)	−0.0109 (8)
C3	0.0463 (12)	0.0424 (11)	0.0464 (12)	−0.0104 (9)	−0.0050 (9)	−0.0138 (9)
C4	0.0497 (13)	0.0499 (13)	0.0429 (12)	−0.0139 (10)	0.0019 (10)	−0.0056 (10)
C5	0.0659 (15)	0.0634 (15)	0.0325 (11)	−0.0148 (12)	−0.0011 (10)	−0.0112 (10)
C6	0.0557 (13)	0.0513 (13)	0.0384 (11)	−0.0118 (10)	−0.0073 (10)	−0.0149 (10)
C7	0.0369 (10)	0.0344 (10)	0.0335 (9)	−0.0039 (8)	−0.0044 (8)	−0.0095 (8)
C8	0.0365 (10)	0.0412 (11)	0.0480 (12)	−0.0122 (9)	−0.0032 (9)	−0.0081 (9)
C9	0.0525 (13)	0.0337 (10)	0.0574 (13)	−0.0131 (9)	−0.0071 (10)	−0.0134 (9)
C10	0.0425 (11)	0.0373 (10)	0.0454 (11)	−0.0003 (9)	−0.0070 (9)	−0.0152 (9)
C11	0.0340 (10)	0.0450 (11)	0.0483 (12)	−0.0082 (9)	−0.0047 (9)	−0.0159 (9)
C12	0.0402 (10)	0.0365 (10)	0.0462 (11)	−0.0098 (8)	−0.0065 (9)	−0.0154 (9)
N1	0.0445 (10)	0.0402 (9)	0.0379 (9)	−0.0001 (8)	−0.0002 (8)	−0.0113 (8)
O1	0.0531 (9)	0.0575 (10)	0.0612 (10)	−0.0182 (8)	−0.0146 (8)	−0.0175 (8)
O2	0.0368 (8)	0.0504 (9)	0.0592 (10)	0.0036 (7)	0.0019 (7)	−0.0141 (8)
Cl1	0.0641 (4)	0.0632 (4)	0.0384 (3)	−0.0168 (3)	0.0000 (2)	−0.0230 (3)
Cl2	0.0816 (5)	0.0924 (6)	0.0669 (5)	−0.0470 (4)	0.0183 (4)	−0.0121 (4)
Cl3	0.0592 (4)	0.0491 (3)	0.0987 (5)	0.0051 (3)	0.0000 (4)	−0.0350 (4)
S1	0.0324 (3)	0.0389 (3)	0.0448 (3)	−0.0049 (2)	−0.0031 (2)	−0.0116 (2)

C1—C6	1.395 (3)	C7—N1	1.440 (3)
C1—C2	1.398 (3)	C8—C9	1.384 (3)
C1—S1	1.787 (2)	C8—H8	0.93
C2—C3	1.387 (3)	C9—C10	1.384 (3)
C2—Cl1	1.743 (2)	C9—H9	0.93
C3—C4	1.389 (3)	C10—C11	1.384 (3)
C3—H3	0.93	C10—Cl3	1.746 (2)
C4—C5	1.380 (4)	C11—C12	1.389 (3)
C4—Cl2	1.743 (2)	C11—H11	0.93
C5—C6	1.391 (3)	C12—H12	0.93
C5—H5	0.93	N1—S1	1.6203 (19)
C6—H6	0.93	N1—H1N	0.839 (16)
C7—C12	1.391 (3)	O1—S1	1.4305 (17)
C7—C8	1.391 (3)	O2—S1	1.4398 (16)
C6—C1—C2	118.88 (19)	C7—C8—H8	119.8
C6—C1—S1	118.25 (16)	C10—C9—C8	119.11 (19)
C2—C1—S1	122.84 (15)	C10—C9—H9	120.4
C3—C2—C1	120.79 (18)	C8—C9—H9	120.4
C3—C2—Cl1	117.32 (16)	C9—C10—C11	121.48 (19)
C1—C2—Cl1	121.87 (15)	C9—C10—Cl3	119.21 (17)
C2—C3—C4	118.9 (2)	C11—C10—Cl3	119.30 (16)
C2—C3—H3	120.6	C10—C11—C12	119.08 (19)
C4—C3—H3	120.6	C10—C11—H11	120.5
C5—C4—C3	121.7 (2)	C12—C11—H11	120.5
C5—C4—Cl2	119.76 (18)	C11—C12—C7	120.12 (18)
C3—C4—Cl2	118.58 (19)	C11—C12—H12	119.9
C4—C5—C6	119.0 (2)	C7—C12—H12	119.9
C4—C5—H5	120.5	C7—N1—S1	121.38 (14)
C6—C5—H5	120.5	C7—N1—H1N	117.2 (18)
C5—C6—C1	120.8 (2)	S1—N1—H1N	117.4 (18)
C5—C6—H6	119.6	O1—S1—O2	119.68 (10)
C1—C6—H6	119.6	O1—S1—N1	108.21 (10)
C12—C7—C8	119.89 (18)	O2—S1—N1	105.97 (10)
C12—C7—N1	121.13 (18)	O1—S1—C1	105.62 (10)
C8—C7—N1	118.99 (18)	O2—S1—C1	109.05 (10)
C9—C8—C7	120.31 (19)	N1—S1—C1	107.86 (10)
C9—C8—H8	119.8
C6—C1—C2—C3	0.4 (3)	C8—C9—C10—Cl3	−177.94 (18)
S1—C1—C2—C3	−177.75 (16)	C9—C10—C11—C12	−1.4 (3)
C6—C1—C2—Cl1	178.71 (16)	Cl3—C10—C11—C12	177.38 (17)
S1—C1—C2—Cl1	0.6 (2)	C10—C11—C12—C7	0.8 (3)
C1—C2—C3—C4	−0.3 (3)	C8—C7—C12—C11	0.3 (3)
Cl1—C2—C3—C4	−178.66 (17)	N1—C7—C12—C11	−179.30 (19)
C2—C3—C4—C5	0.2 (4)	C12—C7—N1—S1	−81.8 (2)
C2—C3—C4—Cl2	179.86 (17)	C8—C7—N1—S1	98.6 (2)
C3—C4—C5—C6	−0.3 (4)	C7—N1—S1—O1	−46.02 (19)
Cl2—C4—C5—C6	−179.93 (19)	C7—N1—S1—O2	−175.53 (16)
C4—C5—C6—C1	0.4 (4)	C7—N1—S1—C1	67.79 (18)
C2—C1—C6—C5	−0.5 (3)	C6—C1—S1—O1	−2.80 (19)
S1—C1—C6—C5	177.76 (19)	C2—C1—S1—O1	175.37 (16)
C12—C7—C8—C9	−0.9 (3)	C6—C1—S1—O2	127.02 (17)
N1—C7—C8—C9	178.7 (2)	C2—C1—S1—O2	−54.81 (19)
C7—C8—C9—C10	0.3 (3)	C6—C1—S1—N1	−118.33 (17)
C8—C9—C10—C11	0.8 (3)	C2—C1—S1—N1	59.84 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.84 (2)	2.20 (2)	3.014 (3)	163 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.84 (2)	2.20 (2)	3.014 (3)	163 (2)

Symmetry code: (i) .