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

In the crystal structure of the title compound, C(12)H(7)Cl(4)NO(2)S, the conformation of the N-H bond is syn to the meta-chloro residue in the aniline benzene ring. The two aromatic rings are tilted relative to each other by 68.9 (1)°. N-H⋯O hydrogen bonds connect the mol-ecules into centrosymmetric dimers.

Related literature

For related structures, see: Gowda et al. (2008 ▶, 2009a ▶,b ▶). For comparative bond lengths in other aryl sulfonamides, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C12H7Cl4NO2S

M = 371.05

Triclinic,

a = 8.1498 (9) Å

b = 8.2633 (9) Å

c = 11.887 (1) Å

α = 81.857 (9)°

β = 72.728 (9)°

γ = 78.213 (9)°

V = 745.49 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.93 mm−1

T = 299 K

0.48 × 0.48 × 0.28 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.664, T max = 0.781

7103 measured reflections

2722 independent reflections

2388 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.152

S = 1.27

2722 reflections

184 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.68 e Å−3

Δρmin = −0.48 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/S1600536809027883/bt5008sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027883/bt5008Isup2.hkl

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

C12H7Cl4NO2S	Z = 2
Mr = 371.05	F(000) = 372
Triclinic, P1	Dx = 1.653 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1498 (9) Å	Cell parameters from 3818 reflections
b = 8.2633 (9) Å	θ = 2.5–27.5°
c = 11.887 (1) Å	µ = 0.93 mm−1
α = 81.857 (9)°	T = 299 K
β = 72.728 (9)°	Plate, colourless
γ = 78.213 (9)°	0.48 × 0.48 × 0.28 mm
V = 745.49 (13) Å3

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2722 independent reflections
Radiation source: fine-focus sealed tube	2388 reflections with I > 2σ(I)
graphite	Rint = 0.022
Rotation method data acquisition using ω and φ scans	θmax = 25.4°, θmin = 2.5°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −9→9
Tmin = 0.664, Tmax = 0.781	k = −9→9
7103 measured reflections	l = −14→14

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152	H atoms treated by a mixture of independent and constrained refinement
S = 1.26	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
2722 reflections	(Δ/σ)max = 0.011
184 parameters	Δρmax = 0.68 e Å−3
1 restraint	Δρmin = −0.48 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	0.3911 (3)	0.5584 (3)	0.7834 (2)	0.0400 (6)
C2	0.3221 (3)	0.4144 (4)	0.8289 (2)	0.0464 (6)
H2	0.3248	0.3369	0.7785	0.056*
C3	0.2503 (3)	0.3869 (4)	0.9484 (3)	0.0551 (7)
C4	0.2429 (4)	0.5027 (4)	1.0245 (2)	0.0559 (7)
C5	0.3100 (4)	0.6460 (4)	0.9785 (3)	0.0590 (7)
H5	0.3034	0.7251	1.0288	0.071*
C6	0.3868 (4)	0.6734 (4)	0.8589 (2)	0.0509 (7)
H6	0.4355	0.7685	0.8291	0.061*
C7	0.2467 (3)	0.8593 (3)	0.61967 (19)	0.0337 (5)
C8	0.1074 (3)	0.7982 (3)	0.6056 (2)	0.0352 (5)
C9	−0.0613 (3)	0.8837 (3)	0.6440 (2)	0.0428 (6)
H9	−0.1543	0.8439	0.6338	0.051*
C10	−0.0895 (3)	1.0267 (3)	0.6968 (2)	0.0447 (6)
C11	0.0473 (3)	1.0924 (4)	0.7108 (3)	0.0513 (7)
H11	0.0262	1.1911	0.7458	0.062*
C12	0.2136 (3)	1.0071 (3)	0.6715 (2)	0.0448 (6)
H12	0.3063	1.0493	0.6798	0.054*
N1	0.4667 (3)	0.5772 (3)	0.65959 (18)	0.0410 (5)
H1N	0.478 (4)	0.500 (3)	0.618 (2)	0.049*
O1	0.5157 (2)	0.7111 (2)	0.46042 (14)	0.0419 (4)
O2	0.5641 (2)	0.8522 (2)	0.61286 (16)	0.0485 (5)
Cl1	0.16795 (16)	0.20525 (13)	1.00219 (9)	0.0922 (4)
Cl2	0.15005 (13)	0.47338 (13)	1.17468 (7)	0.0813 (3)
Cl3	0.13671 (8)	0.61471 (9)	0.54309 (6)	0.0544 (3)
Cl4	−0.30088 (9)	1.12858 (12)	0.75011 (8)	0.0705 (3)
S1	0.46469 (7)	0.75391 (7)	0.57981 (5)	0.0351 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0316 (12)	0.0451 (14)	0.0404 (12)	0.0022 (10)	−0.0130 (9)	−0.0006 (10)
C2	0.0439 (14)	0.0462 (15)	0.0468 (14)	−0.0028 (12)	−0.0137 (11)	−0.0012 (12)
C3	0.0428 (15)	0.0574 (18)	0.0573 (16)	−0.0035 (13)	−0.0135 (12)	0.0126 (14)
C4	0.0497 (16)	0.063 (2)	0.0445 (14)	0.0031 (14)	−0.0093 (12)	0.0021 (13)
C5	0.0676 (19)	0.0600 (19)	0.0475 (16)	−0.0058 (15)	−0.0149 (14)	−0.0083 (14)
C6	0.0569 (16)	0.0503 (17)	0.0459 (14)	−0.0101 (13)	−0.0143 (12)	−0.0040 (12)
C7	0.0279 (11)	0.0346 (12)	0.0387 (11)	−0.0069 (9)	−0.0102 (9)	0.0007 (9)
C8	0.0336 (12)	0.0363 (13)	0.0376 (11)	−0.0085 (10)	−0.0121 (9)	−0.0012 (9)
C9	0.0296 (12)	0.0553 (17)	0.0459 (13)	−0.0081 (11)	−0.0133 (10)	−0.0050 (12)
C10	0.0344 (12)	0.0496 (15)	0.0466 (13)	0.0040 (11)	−0.0136 (10)	−0.0041 (11)
C11	0.0471 (15)	0.0437 (15)	0.0649 (17)	0.0001 (12)	−0.0191 (13)	−0.0141 (13)
C12	0.0394 (14)	0.0414 (14)	0.0582 (15)	−0.0095 (11)	−0.0165 (11)	−0.0089 (12)
N1	0.0415 (11)	0.0400 (12)	0.0400 (11)	−0.0023 (9)	−0.0121 (9)	−0.0036 (9)
O1	0.0400 (9)	0.0414 (10)	0.0410 (9)	−0.0075 (7)	−0.0059 (7)	−0.0036 (7)
O2	0.0312 (9)	0.0583 (12)	0.0615 (11)	−0.0144 (8)	−0.0142 (8)	−0.0106 (9)
Cl1	0.1158 (8)	0.0755 (7)	0.0797 (7)	−0.0406 (6)	−0.0147 (6)	0.0204 (5)
Cl2	0.0879 (6)	0.0890 (7)	0.0450 (4)	−0.0018 (5)	0.0006 (4)	0.0053 (4)
Cl3	0.0432 (4)	0.0551 (5)	0.0720 (5)	−0.0139 (3)	−0.0140 (3)	−0.0250 (4)
Cl4	0.0396 (4)	0.0852 (6)	0.0818 (6)	0.0187 (4)	−0.0207 (4)	−0.0253 (5)
S1	0.0265 (3)	0.0384 (4)	0.0406 (4)	−0.0070 (3)	−0.0087 (2)	−0.0033 (3)

C1—C6	1.386 (4)	C7—S1	1.768 (2)
C1—C2	1.391 (4)	C8—C9	1.385 (3)
C1—N1	1.416 (3)	C8—Cl3	1.724 (2)
C2—C3	1.372 (4)	C9—C10	1.363 (4)
C2—H2	0.9300	C9—H9	0.9300
C3—C4	1.388 (4)	C10—C11	1.396 (4)
C3—Cl1	1.731 (3)	C10—Cl4	1.729 (3)
C4—C5	1.380 (4)	C11—C12	1.371 (4)
C4—Cl2	1.723 (3)	C11—H11	0.9300
C5—C6	1.380 (4)	C12—H12	0.9300
C5—H5	0.9300	N1—S1	1.625 (2)
C6—H6	0.9300	N1—H1N	0.833 (17)
C7—C12	1.387 (3)	O1—S1	1.4297 (17)
C7—C8	1.394 (3)	O2—S1	1.4208 (16)
C6—C1—C2	119.9 (2)	C7—C8—Cl3	121.98 (19)
C6—C1—N1	123.2 (2)	C10—C9—C8	119.3 (2)
C2—C1—N1	116.9 (2)	C10—C9—H9	120.3
C3—C2—C1	119.9 (3)	C8—C9—H9	120.3
C3—C2—H2	120.1	C9—C10—C11	121.9 (2)
C1—C2—H2	120.1	C9—C10—Cl4	119.22 (19)
C2—C3—C4	120.7 (3)	C11—C10—Cl4	118.8 (2)
C2—C3—Cl1	118.6 (2)	C12—C11—C10	118.0 (3)
C4—C3—Cl1	120.7 (2)	C12—C11—H11	121.0
C5—C4—C3	119.2 (3)	C10—C11—H11	121.0
C5—C4—Cl2	119.1 (2)	C11—C12—C7	121.5 (2)
C3—C4—Cl2	121.8 (2)	C11—C12—H12	119.2
C6—C5—C4	120.8 (3)	C7—C12—H12	119.2
C6—C5—H5	119.6	C1—N1—S1	124.52 (17)
C4—C5—H5	119.6	C1—N1—H1N	121 (2)
C5—C6—C1	119.6 (3)	S1—N1—H1N	110 (2)
C5—C6—H6	120.2	O2—S1—O1	118.63 (10)
C1—C6—H6	120.2	O2—S1—N1	109.79 (11)
C12—C7—C8	119.0 (2)	O1—S1—N1	104.74 (10)
C12—C7—S1	117.67 (17)	O2—S1—C7	105.89 (11)
C8—C7—S1	123.32 (18)	O1—S1—C7	111.08 (10)
C9—C8—C7	120.2 (2)	N1—S1—C7	106.12 (11)
C9—C8—Cl3	117.83 (17)
C6—C1—C2—C3	0.0 (4)	C8—C9—C10—C11	1.7 (4)
N1—C1—C2—C3	178.6 (2)	C8—C9—C10—Cl4	−177.29 (18)
C1—C2—C3—C4	1.1 (4)	C9—C10—C11—C12	−1.1 (4)
C1—C2—C3—Cl1	−179.28 (19)	Cl4—C10—C11—C12	177.9 (2)
C2—C3—C4—C5	−0.4 (4)	C10—C11—C12—C7	−0.3 (4)
Cl1—C3—C4—C5	179.9 (2)	C8—C7—C12—C11	1.1 (4)
C2—C3—C4—Cl2	178.9 (2)	S1—C7—C12—C11	−176.5 (2)
Cl1—C3—C4—Cl2	−0.8 (4)	C6—C1—N1—S1	−34.0 (3)
C3—C4—C5—C6	−1.3 (5)	C2—C1—N1—S1	147.43 (19)
Cl2—C4—C5—C6	179.4 (2)	C1—N1—S1—O2	65.2 (2)
C4—C5—C6—C1	2.3 (5)	C1—N1—S1—O1	−166.37 (17)
C2—C1—C6—C5	−1.7 (4)	C1—N1—S1—C7	−48.8 (2)
N1—C1—C6—C5	179.8 (2)	C12—C7—S1—O2	0.2 (2)
C12—C7—C8—C9	−0.5 (4)	C8—C7—S1—O2	−177.34 (19)
S1—C7—C8—C9	176.96 (18)	C12—C7—S1—O1	−129.9 (2)
C12—C7—C8—Cl3	−179.53 (19)	C8—C7—S1—O1	52.6 (2)
S1—C7—C8—Cl3	−2.0 (3)	C12—C7—S1—N1	116.8 (2)
C7—C8—C9—C10	−0.8 (4)	C8—C7—S1—N1	−60.7 (2)
Cl3—C8—C9—C10	178.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.83 (2)	2.08 (2)	2.903 (3)	170 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.833 (17)	2.079 (18)	2.903 (3)	170 (3)

Symmetry code: (i) .