4-Chloro-N-(3,5-dichloro-phen-yl)-2-methyl-benzene-sulfonamide.

In the title compound, C(13)H(10)Cl(3)NO(2)S, torsion angle of the C-SO(2)-NH-C group in the mol-ecule is -58.57 (26)°. The sulfonyl and aniline benzene rings are tilted relative to each other by 84.2 (1)°. The crystal structure features inversion-related dimers linked by pairs of N-H⋯O hydrogen bonds.

Related literature

For the preparation of the title compound, see: Savitha & Gowda (2006 ▶). For the hydrogen-bonding preferences of sulfonamides, see: Adsmond & Grant (2001 ▶). For studies of the effects of substituents on the structure and other aspects of N-(ar­yl)amides, see: Gowda et al. (2000 ▶); of N-(ar­yl)methane­sulfonamides, see: Gowda et al. (2007 ▶); of N-(ar­yl)aryl­sulfonamides, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶); Rodrigues et al. (2011 ▶); Shetty & Gowda (2005 ▶); and of N-(chloro)­aryl­sulfonamides, see: Gowda et al. (2004 ▶).

Experimental

Crystal data

C13H10Cl3NO2S

M = 350.63

Triclinic,

a = 7.9638 (8) Å

b = 8.8494 (9) Å

c = 11.649 (1) Å

α = 97.002 (8)°

β = 102.726 (9)°

γ = 100.408 (9)°

V = 776.35 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.72 mm−1

T = 293 K

0.44 × 0.42 × 0.36 mm

Data collection

Oxford Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.742, T max = 0.781

5369 measured reflections

3137 independent reflections

2649 reflections with I > 2σ(I)

R int = 0.009

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.140

S = 1.06

3137 reflections

185 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.47 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/S1600536811043327/bt5682sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811043327/bt5682Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811043327/bt5682Isup3.cml

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

C13H10Cl3NO2S	Z = 2
Mr = 350.63	F(000) = 356
Triclinic, P1	Dx = 1.500 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9638 (8) Å	Cell parameters from 3195 reflections
b = 8.8494 (9) Å	θ = 3.2–27.7°
c = 11.649 (1) Å	µ = 0.72 mm−1
α = 97.002 (8)°	T = 293 K
β = 102.726 (9)°	Prism, colourless
γ = 100.408 (9)°	0.44 × 0.42 × 0.36 mm
V = 776.35 (13) Å3

Oxford Xcalibur diffractometer with a Sapphire CCD detector	3137 independent reflections
Radiation source: fine-focus sealed tube	2649 reflections with I > 2σ(I)
graphite	Rint = 0.009
rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 3.2°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −9→9
Tmin = 0.742, Tmax = 0.781	k = −11→6
5369 measured reflections	l = −14→13

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0686P)2 + 0.5149P] where P = (Fo2 + 2Fc2)/3
3137 reflections	(Δ/σ)max < 0.001
185 parameters	Δρmax = 0.44 e Å−3
1 restraint	Δρmin = −0.47 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	0.6313 (3)	0.3284 (3)	0.8732 (2)	0.0413 (5)
C2	0.7898 (3)	0.2789 (3)	0.8801 (2)	0.0520 (6)
C3	0.9242 (4)	0.3774 (4)	0.8502 (3)	0.0671 (8)
H3	1.0310	0.3479	0.8525	0.080*
C4	0.9016 (4)	0.5179 (4)	0.8174 (3)	0.0660 (8)
C5	0.7472 (4)	0.5659 (3)	0.8117 (3)	0.0643 (8)
H5	0.7342	0.6614	0.7895	0.077*
C6	0.6109 (4)	0.4700 (3)	0.8396 (2)	0.0523 (6)
H6	0.5043	0.5006	0.8359	0.063*
C7	0.3567 (3)	0.0027 (3)	0.7092 (2)	0.0473 (6)
C8	0.3722 (4)	−0.1450 (3)	0.6648 (2)	0.0549 (6)
H8	0.4155	−0.2093	0.7163	0.066*
C9	0.3226 (5)	−0.1955 (4)	0.5433 (3)	0.0707 (8)
C10	0.2603 (5)	−0.1027 (5)	0.4647 (3)	0.0769 (10)
H10	0.2280	−0.1379	0.3827	0.092*
C11	0.2473 (4)	0.0441 (4)	0.5115 (3)	0.0667 (8)
C12	0.2941 (4)	0.0998 (3)	0.6324 (2)	0.0570 (7)
H12	0.2841	0.1995	0.6617	0.068*
C13	0.8193 (4)	0.1183 (4)	0.9168 (3)	0.0657 (8)
H13A	0.7491	0.0347	0.8550	0.079*
H13B	0.7852	0.1076	0.9900	0.079*
H13C	0.9415	0.1148	0.9278	0.079*
N1	0.4035 (3)	0.0459 (3)	0.83447 (19)	0.0530 (5)
H1N	0.440 (4)	−0.018 (3)	0.874 (3)	0.064*
O1	0.5024 (3)	0.1945 (2)	1.03359 (15)	0.0547 (5)
O2	0.3065 (3)	0.2924 (3)	0.8798 (2)	0.0652 (5)
Cl1	1.07180 (15)	0.63564 (18)	0.77947 (12)	0.1240 (5)
Cl2	0.3407 (2)	−0.38086 (15)	0.49006 (10)	0.1233 (5)
Cl3	0.16476 (15)	0.16169 (14)	0.41414 (9)	0.1002 (4)
S1	0.45050 (8)	0.21891 (7)	0.91211 (5)	0.04505 (19)

	U11	U22	U33	U12	U13	U23
C1	0.0421 (12)	0.0438 (12)	0.0388 (11)	0.0124 (9)	0.0091 (9)	0.0067 (9)
C2	0.0455 (13)	0.0640 (16)	0.0511 (14)	0.0199 (12)	0.0100 (11)	0.0186 (12)
C3	0.0386 (13)	0.099 (2)	0.0649 (18)	0.0144 (14)	0.0081 (12)	0.0280 (17)
C4	0.0526 (16)	0.081 (2)	0.0532 (15)	−0.0097 (14)	0.0028 (12)	0.0232 (14)
C5	0.0736 (19)	0.0516 (16)	0.0627 (17)	0.0044 (14)	0.0087 (14)	0.0187 (13)
C6	0.0579 (15)	0.0477 (14)	0.0540 (14)	0.0182 (12)	0.0128 (12)	0.0104 (11)
C7	0.0420 (12)	0.0527 (14)	0.0440 (12)	0.0003 (10)	0.0105 (10)	0.0107 (10)
C8	0.0544 (15)	0.0579 (15)	0.0492 (14)	0.0075 (12)	0.0113 (11)	0.0066 (12)
C9	0.077 (2)	0.072 (2)	0.0558 (17)	0.0080 (16)	0.0166 (15)	−0.0060 (15)
C10	0.079 (2)	0.100 (3)	0.0421 (15)	0.0053 (19)	0.0079 (14)	0.0072 (16)
C11	0.0576 (17)	0.086 (2)	0.0512 (15)	0.0018 (15)	0.0064 (13)	0.0256 (15)
C12	0.0555 (15)	0.0586 (16)	0.0530 (15)	0.0050 (12)	0.0076 (12)	0.0154 (12)
C13	0.0505 (15)	0.082 (2)	0.085 (2)	0.0451 (15)	0.0225 (14)	0.0335 (16)
N1	0.0683 (14)	0.0466 (12)	0.0415 (11)	0.0092 (10)	0.0088 (10)	0.0104 (9)
O1	0.0713 (12)	0.0540 (10)	0.0429 (9)	0.0162 (9)	0.0200 (8)	0.0084 (8)
O2	0.0515 (11)	0.0776 (14)	0.0795 (14)	0.0308 (10)	0.0258 (10)	0.0203 (11)
Cl1	0.0745 (6)	0.1562 (12)	0.1290 (10)	−0.0240 (7)	0.0142 (6)	0.0702 (9)
Cl2	0.1735 (13)	0.0994 (8)	0.0837 (7)	0.0466 (8)	0.0144 (7)	−0.0283 (6)
Cl3	0.1019 (7)	0.1234 (9)	0.0713 (6)	0.0149 (6)	0.0016 (5)	0.0515 (6)
S1	0.0460 (3)	0.0480 (3)	0.0460 (3)	0.0156 (2)	0.0163 (2)	0.0092 (2)

C1—C6	1.383 (3)	C8—H8	0.9300
C1—C2	1.399 (3)	C9—C10	1.375 (5)
C1—S1	1.763 (2)	C9—Cl2	1.725 (4)
C2—C3	1.388 (4)	C10—C11	1.377 (5)
C2—C13	1.575 (4)	C10—H10	0.9300
C3—C4	1.376 (5)	C11—C12	1.377 (4)
C3—H3	0.9300	C11—Cl3	1.734 (3)
C4—C5	1.362 (5)	C12—H12	0.9300
C4—Cl1	1.727 (3)	C13—H13A	0.9600
C5—C6	1.376 (4)	C13—H13B	0.9600
C5—H5	0.9300	C13—H13C	0.9600
C6—H6	0.9300	N1—S1	1.615 (2)
C7—C8	1.383 (4)	N1—H1N	0.825 (17)
C7—C12	1.391 (4)	O1—S1	1.4384 (19)
C7—N1	1.410 (3)	O2—S1	1.4206 (19)
C8—C9	1.376 (4)
C6—C1—C2	121.3 (2)	C8—C9—Cl2	118.2 (3)
C6—C1—S1	116.38 (19)	C9—C10—C11	117.7 (3)
C2—C1—S1	122.24 (19)	C9—C10—H10	121.2
C3—C2—C1	116.9 (2)	C11—C10—H10	121.2
C3—C2—C13	119.8 (2)	C10—C11—C12	122.6 (3)
C1—C2—C13	123.3 (2)	C10—C11—Cl3	118.5 (2)
C4—C3—C2	121.0 (3)	C12—C11—Cl3	118.9 (3)
C4—C3—H3	119.5	C11—C12—C7	118.0 (3)
C2—C3—H3	119.5	C11—C12—H12	121.0
C5—C4—C3	121.8 (3)	C7—C12—H12	121.0
C5—C4—Cl1	118.9 (3)	C2—C13—H13A	109.5
C3—C4—Cl1	119.3 (3)	C2—C13—H13B	109.5
C4—C5—C6	118.6 (3)	H13A—C13—H13B	109.5
C4—C5—H5	120.7	C2—C13—H13C	109.5
C6—C5—H5	120.7	H13A—C13—H13C	109.5
C5—C6—C1	120.5 (3)	H13B—C13—H13C	109.5
C5—C6—H6	119.8	C7—N1—S1	128.18 (19)
C1—C6—H6	119.8	C7—N1—H1N	117 (2)
C8—C7—C12	120.6 (2)	S1—N1—H1N	112 (2)
C8—C7—N1	116.5 (2)	O2—S1—O1	118.37 (12)
C12—C7—N1	122.8 (3)	O2—S1—N1	109.26 (13)
C9—C8—C7	119.0 (3)	O1—S1—N1	104.09 (11)
C9—C8—H8	120.5	O2—S1—C1	107.01 (12)
C7—C8—H8	120.5	O1—S1—C1	109.78 (11)
C10—C9—C8	122.0 (3)	N1—S1—C1	107.94 (12)
C10—C9—Cl2	119.8 (3)
C6—C1—C2—C3	−0.8 (4)	Cl2—C9—C10—C11	179.7 (3)
S1—C1—C2—C3	−178.2 (2)	C9—C10—C11—C12	0.1 (5)
C6—C1—C2—C13	−179.5 (3)	C9—C10—C11—Cl3	−178.7 (3)
S1—C1—C2—C13	3.1 (4)	C10—C11—C12—C7	0.0 (5)
C1—C2—C3—C4	1.0 (4)	Cl3—C11—C12—C7	178.7 (2)
C13—C2—C3—C4	179.7 (3)	C8—C7—C12—C11	0.4 (4)
C2—C3—C4—C5	−0.6 (5)	N1—C7—C12—C11	−178.1 (2)
C2—C3—C4—Cl1	−179.3 (2)	C8—C7—N1—S1	161.9 (2)
C3—C4—C5—C6	−0.1 (5)	C12—C7—N1—S1	−19.5 (4)
Cl1—C4—C5—C6	178.6 (2)	C7—N1—S1—O2	57.5 (3)
C4—C5—C6—C1	0.3 (4)	C7—N1—S1—O1	−175.2 (2)
C2—C1—C6—C5	0.2 (4)	C7—N1—S1—C1	−58.6 (3)
S1—C1—C6—C5	177.7 (2)	C6—C1—S1—O2	9.9 (2)
C12—C7—C8—C9	−0.8 (4)	C2—C1—S1—O2	−172.5 (2)
N1—C7—C8—C9	177.8 (3)	C6—C1—S1—O1	−119.7 (2)
C7—C8—C9—C10	0.9 (5)	C2—C1—S1—O1	57.8 (2)
C7—C8—C9—Cl2	−179.3 (2)	C6—C1—S1—N1	127.4 (2)
C8—C9—C10—C11	−0.5 (5)	C2—C1—S1—N1	−55.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.83 (2)	2.06 (2)	2.884 (3)	172 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.83 (2)	2.06 (2)	2.884 (3)	172 (3)

Symmetry code: (i) .