2,4-Dichloro-N-(3,5-dichloro-phen-yl)benzene-sulfonamide.

In the title compound, C(12)H(7)Cl(4)NO(2)S, the N-H bond in the C-SO(2)-NH-C segment is syn with respect to the ortho-Cl atom of the sulfonyl-benzene ring and one of the meta-Cl atoms of the aniline ring. The C-SO(2)-NH-C torsion angle is -93.9 (2)°. The benzene rings are tilted relative to each other by 61.9 (1)°. The crystal structure features inversion-related dimers linked by pairs of N-H⋯O hydrogen bonds.

Related literature

For the preparation of the title compound, see: Savitha & Gowda (2006 ▶). For hydrogen-bonding modes of n class="Chemical">sulfonamides, see; Adsmond & Grant (2001 ▶). For studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-substituted amides, see: Gowda et al. (2000 ▶), on methane­sulfonamides, see: Gowda et al. (2007 ▶), on aryl­sulfonamides, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶); Gowda et al. (2009 ▶); Shetty & Gowda (2005 ▶) and on N-(chloro)-aryl­sulfonamides, see: Gowda et al. (2003 ▶).

Experimental

Crystal data

C12H7Cl4NO2S

M = 371.05

Triclinic,

a = 8.075 (1) Å

b = 9.479 (1) Å

c = 10.103 (2) Å

α = 84.90 (2)°

β = 78.49 (1)°

γ = 79.28 (1)°

V = 743.46 (19) Å3

Z = 2

Mo Kα radiation

μ = 0.93 mm−1

T = 293 K

0.48 × 0.44 × 0.32 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.663, T max = 0.754

4974 measured reflections

3027 independent reflections

2423 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.104

S = 1.03

3027 reflections

184 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 ▶); 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 datablock(s) I, global. DOI: 10.1107/S160053681104219X/rz2649sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104219X/rz2649Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681104219X/rz2649Isup3.cml

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

C12H7Cl4NO2S	Z = 2
Mr = 371.05	F(000) = 372
Triclinic, P1	Dx = 1.657 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.075 (1) Å	Cell parameters from 2149 reflections
b = 9.479 (1) Å	θ = 2.6–27.7°
c = 10.103 (2) Å	µ = 0.93 mm−1
α = 84.90 (2)°	T = 293 K
β = 78.49 (1)°	Prism, light pink
γ = 79.28 (1)°	0.48 × 0.44 × 0.32 mm
V = 743.46 (19) Å3

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	3027 independent reflections
Radiation source: fine-focus sealed tube	2423 reflections with I > 2σ(I)
graphite	Rint = 0.014
Rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −10→10
Tmin = 0.663, Tmax = 0.754	k = −11→11
4974 measured reflections	l = −12→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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0494P)2 + 0.2632P] where P = (Fo2 + 2Fc2)/3
3027 reflections	(Δ/σ)max = 0.001
184 parameters	Δρmax = 0.36 e Å−3
1 restraint	Δρmin = −0.29 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	0.2231 (3)	0.3850 (2)	0.6848 (2)	0.0383 (5)
C2	0.3719 (3)	0.3794 (3)	0.7381 (2)	0.0401 (5)
C3	0.5311 (3)	0.3381 (3)	0.6599 (3)	0.0454 (6)
H3	0.6298	0.3351	0.6951	0.055*
C4	0.5432 (3)	0.3010 (3)	0.5291 (3)	0.0481 (6)
C5	0.3988 (3)	0.3048 (3)	0.4738 (3)	0.0520 (6)
H5	0.4086	0.2792	0.3855	0.062*
C6	0.2400 (3)	0.3475 (3)	0.5529 (2)	0.0466 (6)
H6	0.1419	0.3512	0.5167	0.056*
C7	−0.0988 (3)	0.2062 (2)	0.9076 (2)	0.0397 (5)
C8	−0.1821 (3)	0.1626 (3)	1.0339 (3)	0.0431 (5)
H8	−0.1863	0.2132	1.1096	0.052*
C9	−0.2587 (3)	0.0423 (3)	1.0452 (3)	0.0442 (6)
C10	−0.2563 (3)	−0.0345 (3)	0.9350 (3)	0.0482 (6)
H10	−0.3092	−0.1149	0.9440	0.058*
C11	−0.1723 (3)	0.0125 (3)	0.8107 (3)	0.0455 (6)
C12	−0.0919 (3)	0.1312 (3)	0.7950 (3)	0.0436 (5)
H12	−0.0345	0.1599	0.7105	0.052*
N1	−0.0178 (3)	0.3284 (2)	0.9021 (2)	0.0470 (5)
H1N	−0.017 (4)	0.358 (3)	0.975 (2)	0.056*
O1	−0.1015 (2)	0.4407 (2)	0.68767 (18)	0.0528 (5)
O2	0.0147 (2)	0.57618 (18)	0.83484 (17)	0.0488 (4)
Cl1	0.36340 (9)	0.42083 (9)	0.90298 (7)	0.0630 (2)
Cl2	0.74509 (9)	0.25049 (9)	0.43243 (8)	0.0707 (2)
Cl3	−0.36154 (9)	−0.01334 (8)	1.20398 (7)	0.0631 (2)
Cl4	−0.16598 (10)	−0.08094 (8)	0.66939 (8)	0.0692 (2)
S1	0.01475 (7)	0.44418 (6)	0.77605 (6)	0.04076 (17)

	U11	U22	U33	U12	U13	U23
C1	0.0362 (12)	0.0411 (12)	0.0409 (12)	−0.0147 (10)	−0.0093 (9)	0.0030 (10)
C2	0.0375 (12)	0.0447 (13)	0.0423 (13)	−0.0134 (10)	−0.0122 (10)	−0.0015 (10)
C3	0.0359 (12)	0.0481 (14)	0.0548 (15)	−0.0136 (11)	−0.0101 (11)	0.0010 (11)
C4	0.0428 (14)	0.0466 (14)	0.0531 (15)	−0.0151 (11)	0.0007 (11)	0.0003 (11)
C5	0.0567 (16)	0.0606 (16)	0.0418 (14)	−0.0193 (13)	−0.0069 (12)	−0.0047 (12)
C6	0.0455 (14)	0.0566 (15)	0.0436 (14)	−0.0189 (12)	−0.0148 (11)	0.0007 (11)
C7	0.0274 (11)	0.0447 (13)	0.0487 (13)	−0.0103 (10)	−0.0098 (9)	0.0027 (10)
C8	0.0339 (12)	0.0466 (13)	0.0491 (14)	−0.0096 (10)	−0.0080 (10)	0.0016 (11)
C9	0.0288 (11)	0.0477 (14)	0.0547 (14)	−0.0092 (10)	−0.0071 (10)	0.0089 (11)
C10	0.0354 (13)	0.0437 (13)	0.0681 (17)	−0.0129 (11)	−0.0125 (12)	0.0020 (12)
C11	0.0335 (12)	0.0459 (13)	0.0584 (15)	−0.0044 (10)	−0.0117 (11)	−0.0081 (12)
C12	0.0311 (12)	0.0501 (14)	0.0495 (14)	−0.0098 (10)	−0.0057 (10)	−0.0004 (11)
N1	0.0489 (12)	0.0557 (12)	0.0430 (11)	−0.0264 (10)	−0.0104 (10)	0.0028 (10)
O1	0.0390 (9)	0.0673 (12)	0.0570 (11)	−0.0153 (8)	−0.0199 (8)	0.0081 (9)
O2	0.0475 (10)	0.0473 (10)	0.0518 (10)	−0.0135 (8)	−0.0059 (8)	−0.0004 (8)
Cl1	0.0509 (4)	0.0957 (6)	0.0500 (4)	−0.0160 (4)	−0.0187 (3)	−0.0163 (4)
Cl2	0.0511 (4)	0.0808 (5)	0.0728 (5)	−0.0128 (4)	0.0116 (3)	−0.0131 (4)
Cl3	0.0566 (4)	0.0687 (5)	0.0631 (4)	−0.0273 (4)	−0.0004 (3)	0.0123 (3)
Cl4	0.0673 (5)	0.0699 (5)	0.0748 (5)	−0.0190 (4)	−0.0071 (4)	−0.0263 (4)
S1	0.0344 (3)	0.0473 (3)	0.0433 (3)	−0.0139 (3)	−0.0101 (2)	0.0040 (3)

C1—C6	1.383 (3)	C7—N1	1.424 (3)
C1—C2	1.402 (3)	C8—C9	1.381 (3)
C1—S1	1.765 (2)	C8—H8	0.9300
C2—C3	1.376 (3)	C9—C10	1.378 (4)
C2—Cl1	1.731 (2)	C9—Cl3	1.738 (2)
C3—C4	1.378 (4)	C10—C11	1.381 (4)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.383 (4)	C11—C12	1.383 (3)
C4—Cl2	1.731 (3)	C11—Cl4	1.733 (3)
C5—C6	1.379 (4)	C12—H12	0.9300
C5—H5	0.9300	N1—S1	1.618 (2)
C6—H6	0.9300	N1—H1N	0.815 (16)
C7—C12	1.381 (3)	O1—S1	1.4254 (17)
C7—C8	1.386 (3)	O2—S1	1.4319 (18)
C6—C1—C2	118.7 (2)	C7—C8—H8	120.7
C6—C1—S1	118.24 (17)	C10—C9—C8	122.1 (2)
C2—C1—S1	123.06 (18)	C10—C9—Cl3	119.25 (18)
C3—C2—C1	120.3 (2)	C8—C9—Cl3	118.6 (2)
C3—C2—Cl1	117.68 (17)	C9—C10—C11	117.6 (2)
C1—C2—Cl1	121.97 (18)	C9—C10—H10	121.2
C2—C3—C4	119.5 (2)	C11—C10—H10	121.2
C2—C3—H3	120.3	C10—C11—C12	122.3 (2)
C4—C3—H3	120.3	C10—C11—Cl4	119.07 (19)
C3—C4—C5	121.6 (2)	C12—C11—Cl4	118.7 (2)
C3—C4—Cl2	118.57 (19)	C7—C12—C11	118.5 (2)
C5—C4—Cl2	119.9 (2)	C7—C12—H12	120.8
C6—C5—C4	118.4 (2)	C11—C12—H12	120.8
C6—C5—H5	120.8	C7—N1—S1	127.32 (17)
C4—C5—H5	120.8	C7—N1—H1N	115 (2)
C5—C6—C1	121.6 (2)	S1—N1—H1N	114 (2)
C5—C6—H6	119.2	O1—S1—O2	119.41 (11)
C1—C6—H6	119.2	O1—S1—N1	109.48 (10)
C12—C7—C8	120.9 (2)	O2—S1—N1	105.64 (11)
C12—C7—N1	122.7 (2)	O1—S1—C1	106.86 (11)
C8—C7—N1	116.4 (2)	O2—S1—C1	108.24 (10)
C9—C8—C7	118.7 (2)	N1—S1—C1	106.57 (11)
C9—C8—H8	120.7
C6—C1—C2—C3	0.3 (3)	Cl3—C9—C10—C11	−179.56 (18)
S1—C1—C2—C3	−177.25 (18)	C9—C10—C11—C12	0.4 (4)
C6—C1—C2—Cl1	−178.67 (18)	C9—C10—C11—Cl4	179.96 (17)
S1—C1—C2—Cl1	3.7 (3)	C8—C7—C12—C11	0.9 (3)
C1—C2—C3—C4	−0.5 (4)	N1—C7—C12—C11	179.0 (2)
Cl1—C2—C3—C4	178.53 (19)	C10—C11—C12—C7	−1.1 (4)
C2—C3—C4—C5	0.2 (4)	Cl4—C11—C12—C7	179.34 (17)
C2—C3—C4—Cl2	179.58 (18)	C12—C7—N1—S1	30.7 (3)
C3—C4—C5—C6	0.3 (4)	C8—C7—N1—S1	−151.21 (19)
Cl2—C4—C5—C6	−179.1 (2)	C7—N1—S1—O1	21.3 (3)
C4—C5—C6—C1	−0.5 (4)	C7—N1—S1—O2	151.1 (2)
C2—C1—C6—C5	0.2 (4)	C7—N1—S1—C1	−93.9 (2)
S1—C1—C6—C5	177.9 (2)	C6—C1—S1—O1	0.0 (2)
C12—C7—C8—C9	−0.1 (3)	C2—C1—S1—O1	177.56 (19)
N1—C7—C8—C9	−178.3 (2)	C6—C1—S1—O2	−129.83 (19)
C7—C8—C9—C10	−0.6 (4)	C2—C1—S1—O2	47.8 (2)
C7—C8—C9—Cl3	179.45 (17)	C6—C1—S1—N1	116.95 (19)
C8—C9—C10—C11	0.5 (4)	C2—C1—S1—N1	−65.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.82 (2)	2.07 (2)	2.889 (3)	177 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.82 (2)	2.07 (2)	2.889 (3)	177 (3)

Symmetry code: (i) .