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

In the title compound, C(12)H(7)Cl(4)NO(2)S, the conformation of the N-C bond in the C-SO(2)-NH-C segment is gauche with respect to the S=O bonds. Further, the N-H bond in the C-SO(2)-NH-C segment is syn with respect to the ortho-Cl atoms in the aniline and sulfonyl benzene rings. The C-SO(2)-NH-C torsion angle is -51.98 (18)°. The sulfonyl and aniline benzene rings are tilted by 67.7 (1)° relative to each other. An intra-molecular N-H⋯Cl hydrogen bond occurs.

Related literature

For the preparation of the title compound, see: Savitha & Gowda (2006 ▶). For hydrogen-bonding modes of sulfonamides, see: Adsmond & Grant (2001 ▶). For studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Bhat & Gowda (2000 ▶), on N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007 ▶), on N-(ar­yl)-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

Monoclinic,

a = 9.0756 (6) Å

b = 9.7406 (7) Å

c = 16.432 (1) Å

β = 98.157 (6)°

V = 1437.92 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.97 mm−1

T = 293 K

0.48 × 0.48 × 0.40 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.654, T max = 0.699

5584 measured reflections

2929 independent reflections

2377 reflections with I > 2σ(I)

R int = 0.011

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.085

S = 1.06

2929 reflections

184 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.33 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 datablock(s) I, global. DOI: 10.1107/S1600536811040980/ds2148sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811040980/ds2148Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811040980/ds2148Isup3.cml

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

C12H7Cl4NO2S	F(000) = 744
Mr = 371.05	Dx = 1.714 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2527 reflections
a = 9.0756 (6) Å	θ = 3.1–27.7°
b = 9.7406 (7) Å	µ = 0.97 mm−1
c = 16.432 (1) Å	T = 293 K
β = 98.157 (6)°	Prism, light pink
V = 1437.92 (17) Å3	0.48 × 0.48 × 0.40 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2929 independent reflections
Radiation source: fine-focus sealed tube	2377 reflections with I > 2σ(I)
graphite	Rint = 0.011
Rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 3.1°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −11→11
Tmin = 0.654, Tmax = 0.699	k = −12→6
5584 measured reflections	l = −20→7

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0428P)2 + 0.4988P] where P = (Fo2 + 2Fc2)/3
2929 reflections	(Δ/σ)max < 0.001
184 parameters	Δρmax = 0.35 e Å−3
1 restraint	Δρmin = −0.33 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
Cl1	1.01332 (7)	0.16349 (7)	0.03990 (4)	0.06229 (19)
Cl2	0.68073 (12)	0.57632 (9)	−0.09497 (6)	0.0992 (3)
Cl3	0.75598 (6)	−0.10291 (6)	0.09622 (4)	0.05174 (16)
Cl4	0.41139 (7)	−0.13998 (7)	0.06337 (4)	0.06117 (19)
S1	0.94908 (5)	0.25929 (6)	0.22226 (3)	0.03991 (14)
O1	0.90401 (17)	0.33724 (18)	0.28772 (9)	0.0522 (4)
O2	1.10217 (15)	0.22678 (18)	0.22388 (10)	0.0533 (4)
N1	0.86340 (18)	0.11137 (19)	0.21735 (11)	0.0407 (4)
H1N	0.907 (2)	0.052 (2)	0.1941 (13)	0.049*
C1	0.8791 (2)	0.3472 (2)	0.13079 (12)	0.0381 (4)
C2	0.9078 (2)	0.3066 (2)	0.05351 (13)	0.0420 (5)
C3	0.8482 (3)	0.3780 (2)	−0.01612 (14)	0.0518 (6)
H3	0.8692	0.3517	−0.0677	0.062*
C4	0.7580 (3)	0.4880 (3)	−0.00799 (15)	0.0581 (6)
C5	0.7266 (3)	0.5302 (3)	0.06718 (18)	0.0644 (7)
H5	0.6646	0.6051	0.0714	0.077*
C6	0.7884 (3)	0.4598 (2)	0.13660 (15)	0.0521 (6)
H6	0.7688	0.4884	0.1880	0.063*
C7	0.7057 (2)	0.0989 (2)	0.20112 (11)	0.0348 (4)
C8	0.6430 (2)	−0.0002 (2)	0.14600 (11)	0.0357 (4)
C9	0.4892 (2)	−0.0153 (2)	0.13160 (12)	0.0408 (5)
C10	0.3983 (2)	0.0671 (3)	0.16999 (14)	0.0497 (6)
H10	0.2955	0.0570	0.1594	0.060*
C11	0.4611 (2)	0.1651 (3)	0.22439 (15)	0.0520 (6)
H11	0.3998	0.2217	0.2506	0.062*
C12	0.6134 (2)	0.1808 (2)	0.24075 (14)	0.0464 (5)
H12	0.6542	0.2465	0.2784	0.056*

	U11	U22	U33	U12	U13	U23
Cl1	0.0608 (4)	0.0666 (4)	0.0633 (4)	0.0104 (3)	0.0221 (3)	−0.0190 (3)
Cl2	0.1211 (7)	0.0792 (6)	0.0854 (6)	−0.0130 (5)	−0.0259 (5)	0.0308 (4)
Cl3	0.0468 (3)	0.0479 (3)	0.0614 (4)	0.0047 (2)	0.0107 (2)	−0.0119 (3)
Cl4	0.0561 (3)	0.0688 (4)	0.0549 (3)	−0.0229 (3)	−0.0052 (3)	0.0012 (3)
S1	0.0291 (2)	0.0476 (3)	0.0424 (3)	−0.0015 (2)	0.00272 (19)	−0.0094 (2)
O1	0.0480 (9)	0.0646 (11)	0.0438 (8)	−0.0037 (8)	0.0059 (7)	−0.0187 (8)
O2	0.0271 (7)	0.0690 (11)	0.0625 (10)	−0.0014 (7)	0.0024 (6)	−0.0085 (8)
N1	0.0285 (8)	0.0427 (10)	0.0509 (10)	0.0034 (7)	0.0062 (7)	−0.0019 (8)
C1	0.0331 (10)	0.0361 (10)	0.0454 (11)	−0.0060 (8)	0.0062 (8)	−0.0092 (9)
C2	0.0360 (10)	0.0416 (11)	0.0493 (11)	−0.0095 (9)	0.0091 (9)	−0.0104 (10)
C3	0.0543 (13)	0.0543 (14)	0.0466 (13)	−0.0207 (11)	0.0062 (10)	−0.0030 (11)
C4	0.0650 (15)	0.0444 (13)	0.0601 (15)	−0.0169 (12)	−0.0079 (12)	0.0059 (12)
C5	0.0662 (16)	0.0376 (13)	0.0855 (19)	0.0047 (11)	−0.0028 (14)	−0.0026 (13)
C6	0.0571 (14)	0.0413 (12)	0.0579 (13)	0.0037 (10)	0.0076 (11)	−0.0120 (11)
C7	0.0292 (9)	0.0391 (11)	0.0364 (10)	0.0017 (8)	0.0056 (8)	0.0047 (8)
C8	0.0351 (10)	0.0364 (10)	0.0363 (10)	0.0029 (8)	0.0077 (8)	0.0078 (8)
C9	0.0356 (10)	0.0461 (12)	0.0395 (10)	−0.0064 (9)	0.0012 (8)	0.0114 (9)
C10	0.0267 (10)	0.0639 (15)	0.0591 (14)	0.0009 (10)	0.0081 (9)	0.0148 (12)
C11	0.0362 (11)	0.0587 (15)	0.0649 (15)	0.0070 (10)	0.0203 (10)	0.0001 (12)
C12	0.0405 (11)	0.0502 (13)	0.0505 (12)	0.0005 (10)	0.0135 (9)	−0.0053 (10)

Cl1—C2	1.723 (2)	C3—H3	0.9300
Cl2—C4	1.729 (2)	C4—C5	1.370 (4)
Cl3—C8	1.720 (2)	C5—C6	1.380 (3)
Cl4—C9	1.734 (2)	C5—H5	0.9300
S1—O2	1.4216 (15)	C6—H6	0.9300
S1—O1	1.4232 (15)	C7—C12	1.384 (3)
S1—N1	1.6338 (18)	C7—C8	1.389 (3)
S1—C1	1.768 (2)	C8—C9	1.390 (3)
N1—C7	1.424 (2)	C9—C10	1.368 (3)
N1—H1N	0.825 (16)	C10—C11	1.375 (3)
C1—C6	1.383 (3)	C10—H10	0.9300
C1—C2	1.390 (3)	C11—C12	1.379 (3)
C2—C3	1.382 (3)	C11—H11	0.9300
C3—C4	1.366 (4)	C12—H12	0.9300
O2—S1—O1	119.32 (9)	C6—C5—H5	120.5
O2—S1—N1	105.16 (10)	C5—C6—C1	120.9 (2)
O1—S1—N1	108.79 (10)	C5—C6—H6	119.6
O2—S1—C1	110.86 (10)	C1—C6—H6	119.6
O1—S1—C1	106.09 (10)	C12—C7—C8	119.22 (18)
N1—S1—C1	105.90 (9)	C12—C7—N1	121.45 (18)
C7—N1—S1	122.92 (14)	C8—C7—N1	119.31 (17)
C7—N1—H1N	112.9 (17)	C7—C8—C9	119.53 (18)
S1—N1—H1N	112.7 (17)	C7—C8—Cl3	119.83 (14)
C6—C1—C2	118.7 (2)	C9—C8—Cl3	120.64 (16)
C6—C1—S1	118.10 (16)	C10—C9—C8	121.1 (2)
C2—C1—S1	123.21 (16)	C10—C9—Cl4	119.52 (16)
C3—C2—C1	120.7 (2)	C8—C9—Cl4	119.40 (17)
C3—C2—Cl1	117.35 (17)	C9—C10—C11	119.09 (19)
C1—C2—Cl1	121.91 (17)	C9—C10—H10	120.5
C4—C3—C2	118.9 (2)	C11—C10—H10	120.5
C4—C3—H3	120.5	C10—C11—C12	121.0 (2)
C2—C3—H3	120.5	C10—C11—H11	119.5
C3—C4—C5	121.9 (2)	C12—C11—H11	119.5
C3—C4—Cl2	119.2 (2)	C11—C12—C7	120.1 (2)
C5—C4—Cl2	119.0 (2)	C11—C12—H12	120.0
C4—C5—C6	119.0 (2)	C7—C12—H12	120.0
C4—C5—H5	120.5
O2—S1—N1—C7	−169.42 (16)	C4—C5—C6—C1	−0.9 (4)
O1—S1—N1—C7	61.68 (19)	C2—C1—C6—C5	0.4 (3)
C1—S1—N1—C7	−51.98 (18)	S1—C1—C6—C5	−178.02 (19)
O2—S1—C1—C6	−136.46 (17)	S1—N1—C7—C12	−45.7 (3)
O1—S1—C1—C6	−5.5 (2)	S1—N1—C7—C8	136.06 (17)
N1—S1—C1—C6	109.99 (18)	C12—C7—C8—C9	0.0 (3)
O2—S1—C1—C2	45.2 (2)	N1—C7—C8—C9	178.29 (18)
O1—S1—C1—C2	176.12 (16)	C12—C7—C8—Cl3	−179.99 (16)
N1—S1—C1—C2	−68.37 (19)	N1—C7—C8—Cl3	−1.8 (3)
C6—C1—C2—C3	0.7 (3)	C7—C8—C9—C10	0.9 (3)
S1—C1—C2—C3	179.01 (16)	Cl3—C8—C9—C10	−179.07 (16)
C6—C1—C2—Cl1	−177.34 (17)	C7—C8—C9—Cl4	−179.51 (15)
S1—C1—C2—Cl1	1.0 (3)	Cl3—C8—C9—Cl4	0.5 (2)
C1—C2—C3—C4	−1.3 (3)	C8—C9—C10—C11	−0.8 (3)
Cl1—C2—C3—C4	176.82 (17)	Cl4—C9—C10—C11	179.58 (17)
C2—C3—C4—C5	0.8 (4)	C9—C10—C11—C12	−0.2 (3)
C2—C3—C4—Cl2	−179.01 (17)	C10—C11—C12—C7	1.1 (4)
C3—C4—C5—C6	0.2 (4)	C8—C7—C12—C11	−1.0 (3)
Cl2—C4—C5—C6	−179.9 (2)	N1—C7—C12—C11	−179.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···Cl3	0.83 (2)	2.47 (2)	2.9526 (19)	118.(2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯Cl3	0.83 (2)	2.47 (2)	2.9526 (19)	118 (2)