4-Chloro-N-(3,5-dichloro-phenyl)benzene-sulfonamide.

In the title compound, C(12)H(8)Cl(3)NO(2)S, the dihedral angle between the aromatic rings is 87.9 (1)° and the C-S-N-C torsion angle is 77.8 (2)°. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds occur.

Related literature

For hydrogen-bonding preferences of n class="Chemical">sulfonamides, see; Adsmond & Grant (2001 ▶). For our study of the effect of substituents on the structures of N-(ar­yl)-amides, see: Gowda et al. (2004 ▶); on the structures of N-(ar­yl)aryl­sulfonamides, see: Shakuntala et al. (2011a ▶,b ▶); and on the oxidative strengths of N-chloro-N-aryl­sulfonamides, see: Gowda & Kumar (2003 ▶).

Experimental

Crystal data

C12H8Cl3NO2S

M = 336.60

Triclinic,

a = 4.935 (1) Å

b = 11.630 (2) Å

c = 13.115 (2) Å

α = 113.52 (2)°

β = 90.49 (1)°

γ = 96.50 (1)°

V = 684.6 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.82 mm−1

T = 293 K

0.32 × 0.20 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.780, T max = 0.923

4440 measured reflections

2785 independent reflections

2236 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.086

S = 1.03

2785 reflections

175 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.33 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data n class="Disease">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/S160053681101470X/bq2298sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681101470X/bq2298Isup2.hkl

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

C12H8Cl3NO2S	Z = 2
Mr = 336.60	F(000) = 340
Triclinic, P1	Dx = 1.633 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.935 (1) Å	Cell parameters from 1578 reflections
b = 11.630 (2) Å	θ = 3.0–27.8°
c = 13.115 (2) Å	µ = 0.82 mm−1
α = 113.52 (2)°	T = 293 K
β = 90.49 (1)°	Prism, colourless
γ = 96.50 (1)°	0.32 × 0.20 × 0.10 mm
V = 684.6 (2) Å3

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	2785 independent reflections
Radiation source: fine-focus sealed tube	2236 reflections with I > 2σ(I)
graphite	Rint = 0.013
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 3.0°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −6→4
Tmin = 0.780, Tmax = 0.923	k = −14→14
4440 measured reflections	l = −15→16

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0393P)2 + 0.3103P] where P = (Fo2 + 2Fc2)/3
2785 reflections	(Δ/σ)max = 0.005
175 parameters	Δρmax = 0.36 e Å−3
1 restraint	Δρmin = −0.33 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	0.7071 (4)	0.7199 (2)	0.24024 (17)	0.0357 (5)
C2	0.8325 (5)	0.7573 (2)	0.34566 (19)	0.0443 (5)
H2	0.7746	0.7164	0.3913	0.053*
C3	1.0431 (5)	0.8552 (2)	0.3823 (2)	0.0506 (6)
H3	1.1295	0.8807	0.4525	0.061*
C4	1.1242 (5)	0.9149 (2)	0.3139 (2)	0.0466 (6)
C5	0.9996 (5)	0.8800 (2)	0.2095 (2)	0.0507 (6)
H5	1.0565	0.9221	0.1648	0.061*
C6	0.7896 (5)	0.7817 (2)	0.17258 (19)	0.0454 (5)
H6	0.7035	0.7569	0.1024	0.055*
C7	0.7357 (4)	0.39831 (19)	0.18639 (16)	0.0330 (4)
C8	0.6937 (4)	0.4095 (2)	0.29448 (17)	0.0388 (5)
H8	0.5776	0.4644	0.3387	0.047*
C9	0.8290 (5)	0.3369 (2)	0.33442 (18)	0.0416 (5)
C10	1.0005 (5)	0.2536 (2)	0.27211 (19)	0.0463 (6)
H10	1.0892	0.2057	0.3010	0.056*
C11	1.0357 (4)	0.2439 (2)	0.16442 (19)	0.0400 (5)
C12	0.9083 (4)	0.3151 (2)	0.12094 (18)	0.0365 (5)
H12	0.9373	0.3077	0.0487	0.044*
N1	0.5991 (4)	0.46264 (17)	0.13400 (14)	0.0382 (4)
H1N	0.645 (5)	0.452 (2)	0.0694 (15)	0.046*
O1	0.3111 (3)	0.58358 (15)	0.28347 (12)	0.0442 (4)
O2	0.2996 (3)	0.59558 (15)	0.09918 (12)	0.0442 (4)
Cl1	1.39180 (14)	1.03860 (7)	0.36017 (7)	0.0681 (2)
Cl2	0.77531 (16)	0.35067 (7)	0.46970 (5)	0.0603 (2)
Cl3	1.24838 (13)	0.13818 (6)	0.08193 (6)	0.05370 (18)
S1	0.45009 (11)	0.58943 (5)	0.19092 (4)	0.03502 (14)

	U11	U22	U33	U12	U13	U23
C1	0.0393 (11)	0.0375 (11)	0.0312 (10)	0.0088 (9)	0.0033 (9)	0.0137 (9)
C2	0.0567 (14)	0.0441 (13)	0.0365 (12)	0.0058 (11)	−0.0029 (10)	0.0210 (10)
C3	0.0594 (15)	0.0460 (13)	0.0460 (14)	0.0057 (11)	−0.0123 (11)	0.0187 (11)
C4	0.0438 (13)	0.0368 (12)	0.0563 (15)	0.0068 (10)	−0.0006 (11)	0.0154 (11)
C5	0.0588 (15)	0.0504 (14)	0.0501 (14)	0.0054 (12)	0.0082 (12)	0.0279 (12)
C6	0.0553 (14)	0.0514 (14)	0.0321 (11)	0.0054 (11)	0.0030 (10)	0.0197 (10)
C7	0.0362 (11)	0.0341 (11)	0.0301 (10)	−0.0015 (8)	−0.0025 (8)	0.0159 (8)
C8	0.0454 (12)	0.0407 (12)	0.0311 (11)	0.0013 (9)	0.0002 (9)	0.0164 (9)
C9	0.0505 (13)	0.0444 (12)	0.0329 (11)	−0.0039 (10)	−0.0028 (10)	0.0212 (10)
C10	0.0528 (14)	0.0444 (13)	0.0480 (14)	0.0032 (11)	−0.0076 (11)	0.0263 (11)
C11	0.0390 (12)	0.0362 (11)	0.0423 (12)	0.0001 (9)	−0.0002 (9)	0.0145 (10)
C12	0.0388 (11)	0.0382 (11)	0.0327 (11)	−0.0005 (9)	0.0000 (9)	0.0160 (9)
N1	0.0495 (11)	0.0440 (10)	0.0249 (9)	0.0105 (8)	0.0057 (8)	0.0166 (8)
O1	0.0453 (9)	0.0560 (10)	0.0342 (8)	0.0078 (7)	0.0101 (7)	0.0206 (7)
O2	0.0448 (9)	0.0574 (10)	0.0330 (8)	0.0125 (7)	−0.0027 (7)	0.0194 (7)
Cl1	0.0579 (4)	0.0520 (4)	0.0911 (6)	−0.0058 (3)	−0.0129 (4)	0.0292 (4)
Cl2	0.0874 (5)	0.0668 (4)	0.0378 (3)	0.0071 (3)	0.0023 (3)	0.0333 (3)
Cl3	0.0543 (4)	0.0469 (3)	0.0610 (4)	0.0135 (3)	0.0063 (3)	0.0209 (3)
S1	0.0375 (3)	0.0434 (3)	0.0262 (3)	0.0081 (2)	0.0021 (2)	0.0154 (2)

C1—C6	1.385 (3)	C7—N1	1.415 (3)
C1—C2	1.389 (3)	C8—C9	1.381 (3)
C1—S1	1.760 (2)	C8—H8	0.9300
C2—C3	1.376 (3)	C9—C10	1.375 (3)
C2—H2	0.9300	C9—Cl2	1.742 (2)
C3—C4	1.373 (4)	C10—C11	1.385 (3)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.379 (3)	C11—C12	1.377 (3)
C4—Cl1	1.744 (2)	C11—Cl3	1.742 (2)
C5—C6	1.376 (3)	C12—H12	0.9300
C5—H5	0.9300	N1—S1	1.6274 (19)
C6—H6	0.9300	N1—H1N	0.844 (16)
C7—C12	1.391 (3)	O1—S1	1.4207 (16)
C7—C8	1.390 (3)	O2—S1	1.4387 (15)
C6—C1—C2	120.5 (2)	C7—C8—H8	120.9
C6—C1—S1	120.01 (17)	C10—C9—C8	123.1 (2)
C2—C1—S1	119.48 (17)	C10—C9—Cl2	118.69 (17)
C3—C2—C1	119.6 (2)	C8—C9—Cl2	118.17 (19)
C3—C2—H2	120.2	C9—C10—C11	117.1 (2)
C1—C2—H2	120.2	C9—C10—H10	121.4
C2—C3—C4	119.2 (2)	C11—C10—H10	121.4
C2—C3—H3	120.4	C12—C11—C10	122.1 (2)
C4—C3—H3	120.4	C12—C11—Cl3	119.20 (18)
C3—C4—C5	121.8 (2)	C10—C11—Cl3	118.70 (18)
C3—C4—Cl1	119.2 (2)	C11—C12—C7	119.2 (2)
C5—C4—Cl1	119.0 (2)	C11—C12—H12	120.4
C6—C5—C4	119.0 (2)	C7—C12—H12	120.4
C6—C5—H5	120.5	C7—N1—S1	128.77 (14)
C4—C5—H5	120.5	C7—N1—H1N	116.4 (17)
C5—C6—C1	119.8 (2)	S1—N1—H1N	111.1 (17)
C5—C6—H6	120.1	O1—S1—O2	120.01 (10)
C1—C6—H6	120.1	O1—S1—N1	108.60 (10)
C12—C7—C8	120.25 (19)	O2—S1—N1	104.03 (9)
C12—C7—N1	116.01 (18)	O1—S1—C1	108.36 (10)
C8—C7—N1	123.65 (19)	O2—S1—C1	107.64 (10)
C9—C8—C7	118.2 (2)	N1—S1—C1	107.59 (10)
C9—C8—H8	120.9
C6—C1—C2—C3	−1.0 (3)	C9—C10—C11—Cl3	−179.32 (18)
S1—C1—C2—C3	176.71 (18)	C10—C11—C12—C7	−0.9 (3)
C1—C2—C3—C4	0.5 (4)	Cl3—C11—C12—C7	179.18 (16)
C2—C3—C4—C5	0.4 (4)	C8—C7—C12—C11	0.3 (3)
C2—C3—C4—Cl1	−179.78 (18)	N1—C7—C12—C11	−176.30 (19)
C3—C4—C5—C6	−0.6 (4)	C12—C7—N1—S1	−162.46 (16)
Cl1—C4—C5—C6	179.53 (18)	C8—C7—N1—S1	21.1 (3)
C4—C5—C6—C1	0.0 (4)	C7—N1—S1—O1	−39.3 (2)
C2—C1—C6—C5	0.8 (3)	C7—N1—S1—O2	−168.24 (18)
S1—C1—C6—C5	−176.95 (18)	C7—N1—S1—C1	77.8 (2)
C12—C7—C8—C9	0.5 (3)	C6—C1—S1—O1	−151.25 (18)
N1—C7—C8—C9	176.8 (2)	C2—C1—S1—O1	31.0 (2)
C7—C8—C9—C10	−0.6 (3)	C6—C1—S1—O2	−20.1 (2)
C7—C8—C9—Cl2	−179.79 (16)	C2—C1—S1—O2	162.20 (17)
C8—C9—C10—C11	0.0 (4)	C6—C1—S1—N1	91.51 (19)
Cl2—C9—C10—C11	179.18 (17)	C2—C1—S1—N1	−86.23 (19)
C9—C10—C11—C12	0.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.84 (2)	2.08 (2)	2.917 (2)	170 (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)	2.08 (2)	2.917 (2)	170 (2)

Symmetry code: (i) .