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

In the title compound, C(12)H(8)Cl(3)NO(2)S, the two aromatic rings are tilted relative to each other by 56.5 (1)°. The crystal structure features centrosymmetric dimers in which mol-ecules are linked by N-H⋯O hydrogen bonds.

Related literature

For our study of the effect of substituents on the structures of N-(ar­yl)aryl­sulfonamides, see: Gowda et al. (2010 ▶); Nirmala et al. (2010 ▶); Shakuntala et al. (2010 ▶). For related structures, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C12H8Cl3NO2S

M = 336.60

Monoclinic,

a = 7.224 (1) Å

b = 14.975 (2) Å

c = 13.170 (2) Å

β = 97.16 (1)°

V = 1413.6 (3) Å3

Z = 4

Cu Kα radiation

μ = 7.23 mm−1

T = 299 K

0.38 × 0.30 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.170, T max = 0.326

2767 measured reflections

2516 independent reflections

2277 reflections with I > 2σ(I)

R int = 0.062

3 standard reflections every 120 min intensity decay: 0.5%

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.137

S = 1.15

2516 reflections

176 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.46 e Å−3

Δρmin = −0.51 e Å−3

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ▶); 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/S1600536810053638/bt5445sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810053638/bt5445Isup2.hkl

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

C12H8Cl3NO2S	F(000) = 680
Mr = 336.60	Dx = 1.582 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 7.224 (1) Å	θ = 6.8–22.5°
b = 14.975 (2) Å	µ = 7.23 mm−1
c = 13.170 (2) Å	T = 299 K
β = 97.16 (1)°	Prism, colourless
V = 1413.6 (3) Å3	0.38 × 0.30 × 0.20 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	2277 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.062
graphite	θmax = 66.9°, θmin = 4.5°
ω/2θ scans	h = −8→8
Absorption correction: ψ scan (North et al., 1968)	k = −17→0
Tmin = 0.170, Tmax = 0.326	l = −15→1
2767 measured reflections	3 standard reflections every 120 min
2516 independent reflections	intensity decay: 0.5%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.137	w = 1/[σ2(Fo2) + (0.0763P)2 + 1.0223P] where P = (Fo2 + 2Fc2)/3
S = 1.15	(Δ/σ)max = 0.001
2516 reflections	Δρmax = 0.46 e Å−3
176 parameters	Δρmin = −0.51 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0074 (7)

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	0.5255 (4)	0.83900 (18)	0.1877 (2)	0.0332 (6)
C2	0.4733 (4)	0.80016 (19)	0.2749 (2)	0.0372 (6)
H2	0.3502	0.8034	0.2886	0.045*
C3	0.6057 (4)	0.7565 (2)	0.3415 (2)	0.0401 (7)
H3	0.5726	0.7303	0.4008	0.048*
C4	0.7869 (4)	0.7519 (2)	0.3199 (2)	0.0429 (7)
C5	0.8394 (5)	0.7896 (3)	0.2323 (3)	0.0551 (9)
H5	0.9622	0.7853	0.2183	0.066*
C6	0.7079 (5)	0.8336 (2)	0.1657 (3)	0.0504 (8)
H6	0.7412	0.8594	0.1064	0.060*
C7	0.3738 (4)	1.03085 (17)	0.2425 (2)	0.0326 (6)
C8	0.5279 (4)	1.06989 (18)	0.3008 (2)	0.0345 (6)
C9	0.5110 (5)	1.10001 (19)	0.3994 (2)	0.0416 (7)
C10	0.3474 (5)	1.0888 (2)	0.4403 (3)	0.0516 (8)
H10	0.3383	1.1076	0.5068	0.062*
C11	0.1954 (5)	1.0497 (2)	0.3829 (3)	0.0536 (8)
H11	0.0844	1.0422	0.4109	0.064*
C12	0.2082 (4)	1.0217 (2)	0.2843 (2)	0.0431 (7)
H12	0.1050	0.9964	0.2455	0.052*
N1	0.3873 (3)	1.00439 (16)	0.14018 (17)	0.0365 (6)
H1N	0.467 (4)	1.031 (2)	0.107 (2)	0.044*
O1	0.4094 (4)	0.89646 (15)	0.00411 (15)	0.0486 (6)
O2	0.1801 (3)	0.87121 (16)	0.12563 (17)	0.0469 (5)
Cl1	0.95260 (14)	0.69893 (7)	0.40587 (8)	0.0675 (3)
Cl2	0.73258 (11)	1.08276 (6)	0.24909 (6)	0.0517 (3)
Cl3	0.69792 (14)	1.15158 (6)	0.47020 (6)	0.0596 (3)
S1	0.35957 (10)	0.89965 (5)	0.10606 (5)	0.0353 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0408 (15)	0.0311 (13)	0.0289 (13)	−0.0055 (11)	0.0092 (11)	−0.0026 (10)
C2	0.0421 (15)	0.0385 (15)	0.0334 (14)	−0.0047 (12)	0.0137 (12)	−0.0011 (11)
C3	0.0514 (17)	0.0388 (15)	0.0309 (14)	−0.0032 (13)	0.0085 (12)	0.0011 (11)
C4	0.0419 (16)	0.0372 (15)	0.0479 (18)	−0.0019 (12)	−0.0004 (13)	−0.0040 (12)
C5	0.0352 (16)	0.064 (2)	0.067 (2)	−0.0019 (15)	0.0126 (15)	0.0076 (17)
C6	0.0483 (18)	0.059 (2)	0.0478 (18)	−0.0058 (15)	0.0201 (15)	0.0102 (15)
C7	0.0400 (14)	0.0281 (12)	0.0303 (13)	0.0033 (11)	0.0068 (11)	0.0040 (10)
C8	0.0387 (15)	0.0308 (13)	0.0343 (14)	0.0054 (11)	0.0055 (11)	0.0045 (11)
C9	0.0533 (18)	0.0326 (14)	0.0377 (16)	0.0021 (13)	0.0014 (13)	−0.0018 (11)
C10	0.066 (2)	0.0518 (19)	0.0397 (17)	0.0027 (16)	0.0189 (15)	−0.0070 (13)
C11	0.056 (2)	0.056 (2)	0.0528 (19)	−0.0010 (16)	0.0256 (16)	−0.0040 (15)
C12	0.0419 (16)	0.0428 (16)	0.0460 (17)	0.0003 (13)	0.0111 (13)	−0.0012 (13)
N1	0.0441 (13)	0.0362 (13)	0.0302 (12)	−0.0057 (10)	0.0082 (10)	0.0030 (9)
O1	0.0695 (15)	0.0514 (13)	0.0254 (10)	−0.0129 (11)	0.0077 (10)	−0.0030 (8)
O2	0.0413 (12)	0.0525 (13)	0.0460 (12)	−0.0151 (10)	0.0019 (9)	0.0011 (10)
Cl1	0.0594 (6)	0.0690 (6)	0.0686 (6)	0.0082 (4)	−0.0138 (4)	0.0057 (4)
Cl2	0.0380 (4)	0.0687 (6)	0.0490 (5)	−0.0056 (3)	0.0081 (3)	−0.0070 (3)
Cl3	0.0697 (6)	0.0598 (5)	0.0456 (5)	−0.0055 (4)	−0.0068 (4)	−0.0122 (3)
S1	0.0418 (4)	0.0381 (4)	0.0260 (4)	−0.0093 (3)	0.0045 (3)	−0.0011 (2)

C1—C2	1.381 (4)	C7—N1	1.420 (3)
C1—C6	1.386 (4)	C8—C9	1.394 (4)
C1—S1	1.760 (3)	C8—Cl2	1.714 (3)
C2—C3	1.379 (4)	C9—C10	1.369 (5)
C2—H2	0.9300	C9—Cl3	1.724 (3)
C3—C4	1.376 (4)	C10—C11	1.384 (5)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.380 (5)	C11—C12	1.379 (4)
C4—Cl1	1.734 (3)	C11—H11	0.9300
C5—C6	1.378 (5)	C12—H12	0.9300
C5—H5	0.9300	N1—S1	1.637 (2)
C6—H6	0.9300	N1—H1N	0.858 (18)
C7—C12	1.384 (4)	O1—S1	1.434 (2)
C7—C8	1.399 (4)	O2—S1	1.418 (2)
C2—C1—C6	121.0 (3)	C7—C8—Cl2	119.7 (2)
C2—C1—S1	119.3 (2)	C10—C9—C8	120.4 (3)
C6—C1—S1	119.7 (2)	C10—C9—Cl3	119.9 (2)
C3—C2—C1	119.3 (3)	C8—C9—Cl3	119.7 (2)
C3—C2—H2	120.4	C9—C10—C11	120.1 (3)
C1—C2—H2	120.4	C9—C10—H10	119.9
C4—C3—C2	119.6 (3)	C11—C10—H10	119.9
C4—C3—H3	120.2	C12—C11—C10	120.1 (3)
C2—C3—H3	120.2	C12—C11—H11	120.0
C3—C4—C5	121.4 (3)	C10—C11—H11	120.0
C3—C4—Cl1	119.0 (2)	C11—C12—C7	120.5 (3)
C5—C4—Cl1	119.6 (2)	C11—C12—H12	119.8
C6—C5—C4	119.2 (3)	C7—C12—H12	119.8
C6—C5—H5	120.4	C7—N1—S1	120.50 (18)
C4—C5—H5	120.4	C7—N1—H1N	118 (2)
C5—C6—C1	119.5 (3)	S1—N1—H1N	112 (2)
C5—C6—H6	120.2	O2—S1—O1	120.13 (14)
C1—C6—H6	120.2	O2—S1—N1	108.73 (14)
C12—C7—C8	119.4 (3)	O1—S1—N1	104.63 (12)
C12—C7—N1	120.9 (3)	O2—S1—C1	107.60 (13)
C8—C7—N1	119.6 (2)	O1—S1—C1	108.90 (14)
C9—C8—C7	119.4 (3)	N1—S1—C1	106.03 (13)
C9—C8—Cl2	120.9 (2)
C6—C1—C2—C3	0.9 (4)	C8—C9—C10—C11	−1.8 (5)
S1—C1—C2—C3	−176.7 (2)	Cl3—C9—C10—C11	178.3 (3)
C1—C2—C3—C4	−0.4 (4)	C9—C10—C11—C12	0.0 (5)
C2—C3—C4—C5	−0.5 (5)	C10—C11—C12—C7	1.3 (5)
C2—C3—C4—Cl1	178.6 (2)	C8—C7—C12—C11	−0.8 (4)
C3—C4—C5—C6	0.7 (5)	N1—C7—C12—C11	−178.4 (3)
Cl1—C4—C5—C6	−178.3 (3)	C12—C7—N1—S1	−63.5 (3)
C4—C5—C6—C1	−0.1 (6)	C8—C7—N1—S1	118.9 (2)
C2—C1—C6—C5	−0.7 (5)	C7—N1—S1—O2	58.7 (2)
S1—C1—C6—C5	177.0 (3)	C7—N1—S1—O1	−171.8 (2)
C12—C7—C8—C9	−0.9 (4)	C7—N1—S1—C1	−56.7 (2)
N1—C7—C8—C9	176.7 (2)	C2—C1—S1—O2	−20.9 (3)
C12—C7—C8—Cl2	−179.2 (2)	C6—C1—S1—O2	161.3 (2)
N1—C7—C8—Cl2	−1.6 (3)	C2—C1—S1—O1	−152.6 (2)
C7—C8—C9—C10	2.2 (4)	C6—C1—S1—O1	29.6 (3)
Cl2—C8—C9—C10	−179.5 (2)	C2—C1—S1—N1	95.3 (2)
C7—C8—C9—Cl3	−177.8 (2)	C6—C1—S1—N1	−82.5 (3)
Cl2—C8—C9—Cl3	0.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.86 (2)	2.11 (2)	2.944 (3)	163 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.86 (2)	2.11 (2)	2.944 (3)	163 (3)

Symmetry code: (i) .