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

In the title compound, C(13)H(10)Cl(3)NO(2)S, the N-C bond in the C-SO(2)-NH-C segment forms trans and gauche torsion angles with respect to the S=O bonds. Further, the N-H bond in the C-SO(2)-NH-C segment is anti to the meta-Cl atom in the anilino benzene ring and nearly syn with respect to the ortho-methyl group in the sulfonyl benzene ring. The C-SO(2)-NH-C torsion angle is -49.4 (2)°. The sulfonyl and aniline benzene rings are tilted relative to each other by 54.6 (1)°. In the crystal, mol-ecules are linked into chains along the c-axis direction by inter-molecular N-H⋯O hydrogen bonds.

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: Gowda et al. (2003 ▶), on N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007 ▶), on N-(ar­yl)-aryl­sulfonamides, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶); Rodrigues et al. (2011 ▶); Shetty & Gowda (2005 ▶) and on N-(chloro)-aryl­sulfonamides, see: Gowda & Kumar (2003 ▶).

Experimental

Crystal data

C13H10Cl3NO2S

M = 350.63

Monoclinic,

a = 14.563 (2) Å

b = 10.033 (2) Å

c = 10.162 (2) Å

β = 92.60 (2)°

V = 1483.2 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.76 mm−1

T = 293 K

0.44 × 0.44 × 0.38 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.732, T max = 0.762

5266 measured reflections

3005 independent reflections

2373 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.126

S = 1.05

3005 reflections

185 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.42 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/S1600536811041717/tk2797sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811041717/tk2797Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811041717/tk2797Isup3.cml

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

C13H10Cl3NO2S	F(000) = 712
Mr = 350.63	Dx = 1.570 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 926 reflections
a = 14.563 (2) Å	θ = 2.9–27.8°
b = 10.033 (2) Å	µ = 0.76 mm−1
c = 10.162 (2) Å	T = 293 K
β = 92.60 (2)°	Prism, colourless
V = 1483.2 (5) Å3	0.44 × 0.44 × 0.38 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	3005 independent reflections
Radiation source: fine-focus sealed tube	2373 reflections with I > 2σ(I)
graphite	Rint = 0.021
Rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −18→17
Tmin = 0.732, Tmax = 0.762	k = −7→12
5266 measured reflections	l = −11→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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0556P)2 + 1.2273P] where P = (Fo2 + 2Fc2)/3
3005 reflections	(Δ/σ)max < 0.001
185 parameters	Δρmax = 0.41 e Å−3
1 restraint	Δρmin = −0.42 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	0.35205 (17)	0.5208 (3)	0.4395 (2)	0.0366 (5)
C2	0.39656 (16)	0.5884 (3)	0.3403 (2)	0.0376 (5)
C3	0.38485 (18)	0.7259 (3)	0.3330 (3)	0.0426 (6)
H3	0.4140	0.7740	0.2688	0.051*
C4	0.33077 (18)	0.7916 (3)	0.4196 (3)	0.0445 (6)
C5	0.2867 (2)	0.7245 (3)	0.5166 (3)	0.0517 (7)
H5	0.2505	0.7703	0.5746	0.062*
C6	0.2973 (2)	0.5885 (3)	0.5262 (3)	0.0487 (7)
H6	0.2677	0.5416	0.5909	0.058*
C7	0.19793 (17)	0.3372 (3)	0.3148 (2)	0.0384 (6)
C8	0.1756 (2)	0.4145 (3)	0.2057 (3)	0.0519 (7)
H8	0.2208	0.4376	0.1480	0.062*
C9	0.0865 (2)	0.4577 (4)	0.1820 (3)	0.0656 (9)
H9	0.0715	0.5090	0.1079	0.079*
C10	0.0196 (2)	0.4247 (4)	0.2682 (3)	0.0597 (8)
C11	0.0421 (2)	0.3503 (3)	0.3786 (3)	0.0517 (7)
C12	0.13136 (19)	0.3057 (3)	0.4024 (3)	0.0454 (6)
H12	0.1464	0.2549	0.4768	0.054*
C13	0.4565 (2)	0.5208 (3)	0.2399 (3)	0.0542 (8)
H13A	0.4225	0.4502	0.1966	0.065*
H13B	0.5106	0.4847	0.2843	0.065*
H13C	0.4742	0.5850	0.1757	0.065*
Cl1	0.31845 (6)	0.96380 (8)	0.40549 (10)	0.0668 (3)
Cl2	−0.09220 (7)	0.47671 (15)	0.23365 (13)	0.1025 (4)
Cl3	−0.04016 (6)	0.30826 (11)	0.48889 (11)	0.0810 (3)
N1	0.28934 (15)	0.2871 (2)	0.3357 (2)	0.0413 (5)
H1N	0.3167 (19)	0.274 (3)	0.265 (2)	0.050*
O1	0.31664 (17)	0.3122 (2)	0.57571 (19)	0.0578 (6)
O2	0.44650 (14)	0.2959 (2)	0.4296 (2)	0.0573 (5)
S1	0.35718 (5)	0.34532 (7)	0.45424 (6)	0.04128 (19)

	U11	U22	U33	U12	U13	U23
C1	0.0362 (12)	0.0393 (13)	0.0344 (12)	−0.0026 (10)	0.0007 (10)	−0.0030 (10)
C2	0.0325 (11)	0.0432 (14)	0.0376 (12)	−0.0018 (11)	0.0069 (10)	−0.0038 (11)
C3	0.0389 (13)	0.0426 (14)	0.0469 (14)	−0.0051 (11)	0.0084 (11)	0.0019 (12)
C4	0.0405 (13)	0.0389 (14)	0.0540 (16)	−0.0015 (11)	0.0014 (12)	−0.0059 (12)
C5	0.0524 (16)	0.0505 (17)	0.0537 (16)	0.0012 (13)	0.0183 (13)	−0.0147 (14)
C6	0.0545 (16)	0.0531 (17)	0.0398 (14)	−0.0078 (14)	0.0172 (12)	−0.0049 (13)
C7	0.0432 (13)	0.0350 (13)	0.0369 (13)	−0.0034 (11)	0.0004 (10)	−0.0055 (10)
C8	0.0549 (16)	0.0552 (18)	0.0458 (15)	0.0018 (14)	0.0053 (13)	0.0072 (14)
C9	0.069 (2)	0.074 (2)	0.0538 (18)	0.0123 (18)	−0.0016 (16)	0.0139 (17)
C10	0.0492 (16)	0.066 (2)	0.0632 (19)	0.0130 (15)	−0.0027 (15)	−0.0027 (16)
C11	0.0478 (15)	0.0518 (17)	0.0559 (17)	−0.0030 (13)	0.0079 (13)	−0.0032 (14)
C12	0.0496 (15)	0.0443 (15)	0.0423 (14)	−0.0013 (12)	0.0025 (12)	0.0010 (12)
C13	0.0536 (16)	0.0486 (16)	0.0631 (18)	0.0065 (14)	0.0322 (15)	0.0066 (14)
Cl1	0.0696 (5)	0.0436 (4)	0.0880 (6)	0.0018 (4)	0.0133 (4)	−0.0057 (4)
Cl2	0.0603 (5)	0.1361 (11)	0.1105 (9)	0.0337 (6)	−0.0036 (6)	0.0203 (8)
Cl3	0.0575 (5)	0.0977 (7)	0.0900 (7)	0.0007 (5)	0.0267 (5)	0.0084 (6)
N1	0.0458 (12)	0.0412 (12)	0.0369 (11)	−0.0017 (10)	0.0039 (9)	−0.0053 (10)
O1	0.0820 (15)	0.0555 (12)	0.0357 (10)	−0.0111 (11)	0.0012 (10)	0.0099 (9)
O2	0.0465 (11)	0.0550 (12)	0.0693 (14)	0.0099 (10)	−0.0077 (10)	0.0041 (11)
S1	0.0465 (4)	0.0410 (4)	0.0360 (3)	−0.0022 (3)	−0.0017 (3)	0.0034 (3)

C1—C6	1.392 (4)	C8—H8	0.9300
C1—C2	1.399 (4)	C9—C10	1.380 (5)
C1—S1	1.768 (3)	C9—H9	0.9300
C2—C3	1.392 (4)	C10—C11	1.375 (4)
C2—C13	1.531 (4)	C10—Cl2	1.730 (3)
C3—C4	1.375 (4)	C11—C12	1.386 (4)
C3—H3	0.9300	C11—Cl3	1.729 (3)
C4—C5	1.376 (4)	C12—H12	0.9300
C4—Cl1	1.743 (3)	C13—H13A	0.9600
C5—C6	1.377 (4)	C13—H13B	0.9600
C5—H5	0.9300	C13—H13C	0.9600
C6—H6	0.9300	N1—S1	1.631 (2)
C7—C8	1.380 (4)	N1—H1N	0.847 (17)
C7—C12	1.382 (4)	O1—S1	1.431 (2)
C7—N1	1.430 (3)	O2—S1	1.425 (2)
C8—C9	1.378 (4)
C6—C1—C2	121.2 (3)	C10—C9—H9	120.0
C6—C1—S1	117.1 (2)	C11—C10—C9	119.9 (3)
C2—C1—S1	121.61 (19)	C11—C10—Cl2	121.1 (3)
C3—C2—C1	117.3 (2)	C9—C10—Cl2	119.0 (3)
C3—C2—C13	118.4 (2)	C10—C11—C12	120.3 (3)
C1—C2—C13	124.3 (2)	C10—C11—Cl3	121.0 (2)
C4—C3—C2	120.9 (3)	C12—C11—Cl3	118.7 (2)
C4—C3—H3	119.5	C7—C12—C11	119.6 (3)
C2—C3—H3	119.5	C7—C12—H12	120.2
C3—C4—C5	121.5 (3)	C11—C12—H12	120.2
C3—C4—Cl1	118.9 (2)	C2—C13—H13A	109.5
C5—C4—Cl1	119.6 (2)	C2—C13—H13B	109.5
C4—C5—C6	118.8 (3)	H13A—C13—H13B	109.5
C4—C5—H5	120.6	C2—C13—H13C	109.5
C6—C5—H5	120.6	H13A—C13—H13C	109.5
C5—C6—C1	120.3 (3)	H13B—C13—H13C	109.5
C5—C6—H6	119.9	C7—N1—S1	120.79 (18)
C1—C6—H6	119.9	C7—N1—H1N	114 (2)
C8—C7—C12	120.0 (3)	S1—N1—H1N	113 (2)
C8—C7—N1	120.0 (2)	O2—S1—O1	119.09 (14)
C12—C7—N1	120.0 (2)	O2—S1—N1	105.82 (13)
C9—C8—C7	120.2 (3)	O1—S1—N1	107.11 (13)
C9—C8—H8	119.9	O2—S1—C1	111.54 (13)
C7—C8—H8	119.9	O1—S1—C1	106.65 (13)
C8—C9—C10	120.0 (3)	N1—S1—C1	105.81 (12)
C8—C9—H9	120.0
C6—C1—C2—C3	0.9 (4)	Cl2—C10—C11—C12	177.8 (2)
S1—C1—C2—C3	177.02 (19)	C9—C10—C11—Cl3	179.6 (3)
C6—C1—C2—C13	−178.9 (3)	Cl2—C10—C11—Cl3	−1.2 (4)
S1—C1—C2—C13	−2.8 (4)	C8—C7—C12—C11	1.1 (4)
C1—C2—C3—C4	−0.7 (4)	N1—C7—C12—C11	−177.4 (2)
C13—C2—C3—C4	179.1 (3)	C10—C11—C12—C7	0.4 (5)
C2—C3—C4—C5	0.3 (4)	Cl3—C11—C12—C7	179.4 (2)
C2—C3—C4—Cl1	−179.8 (2)	C8—C7—N1—S1	109.5 (3)
C3—C4—C5—C6	−0.2 (4)	C12—C7—N1—S1	−72.0 (3)
Cl1—C4—C5—C6	180.0 (2)	C7—N1—S1—O2	−167.9 (2)
C4—C5—C6—C1	0.4 (4)	C7—N1—S1—O1	64.1 (2)
C2—C1—C6—C5	−0.8 (4)	C7—N1—S1—C1	−49.4 (2)
S1—C1—C6—C5	−177.1 (2)	C6—C1—S1—O2	−143.8 (2)
C12—C7—C8—C9	−1.7 (5)	C2—C1—S1—O2	40.0 (2)
N1—C7—C8—C9	176.9 (3)	C6—C1—S1—O1	−12.2 (2)
C7—C8—C9—C10	0.7 (5)	C2—C1—S1—O1	171.5 (2)
C8—C9—C10—C11	0.8 (5)	C6—C1—S1—N1	101.6 (2)
C8—C9—C10—Cl2	−178.4 (3)	C2—C1—S1—N1	−74.6 (2)
C9—C10—C11—C12	−1.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.85 (2)	2.11 (2)	2.868 (3)	149 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.85 (2)	2.11 (2)	2.868 (3)	149 (3)

Symmetry code: (i) .