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

The mol-ecule of the title compound, C(13)H(11)Cl(2)NO(2)S, is bent at the S atom with a C-SO(2)-NH-C torsion angle of -69.07 (16)°. The sulfonyl and aniline rings are rotated relative to each other by 53.0 (1)°. In the crystal, pairs of N-H⋯O(S) hydrogen bonds link the mol-ecules into centrosymmetric dimers.

Related literature

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: Arjunan et al. (2004 ▶); Gowda et al. (2000 ▶, 2006 ▶), on N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007 ▶) and on N-(ar­yl)-aryl­sulfonamides, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶); Shakuntala et al. (2010 ▶). For the preparation of the title compound, see: Shetty & Gowda (2005 ▶)

Experimental

Crystal data

C13H11Cl2NO2S

M = 316.19

Monoclinic,

a = 11.385 (1) Å

b = 11.959 (1) Å

c = 11.428 (1) Å

β = 112.87 (2)°

V = 1433.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.59 mm−1

T = 293 K

0.44 × 0.38 × 0.28 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.780, T max = 0.851

5752 measured reflections

2924 independent reflections

2361 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.103

S = 1.04

2924 reflections

177 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.38 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/S1600536811030819/bt5590sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811030819/bt5590Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811030819/bt5590Isup3.cml

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

C13H11Cl2NO2S	F(000) = 648
Mr = 316.19	Dx = 1.465 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2440 reflections
a = 11.385 (1) Å	θ = 2.6–27.7°
b = 11.959 (1) Å	µ = 0.59 mm−1
c = 11.428 (1) Å	T = 293 K
β = 112.87 (2)°	Prism, colourless
V = 1433.6 (2) Å3	0.44 × 0.38 × 0.28 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2924 independent reflections
Radiation source: fine-focus sealed tube	2361 reflections with I > 2σ(I)
graphite	Rint = 0.013
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −14→14
Tmin = 0.780, Tmax = 0.851	k = −10→14
5752 measured reflections	l = −14→11

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)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.103	w = 1/[σ2(Fo2) + (0.0569P)2 + 0.3942P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.018
2924 reflections	Δρmax = 0.28 e Å−3
177 parameters	Δρmin = −0.38 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: 0.070 (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	0.21863 (18)	−0.05135 (17)	−0.05214 (18)	0.0414 (4)
C2	0.2305 (2)	−0.1166 (2)	−0.1463 (2)	0.0564 (6)
H2	0.2911	−0.0991	−0.1794	0.068*
C3	0.1525 (2)	−0.2075 (2)	−0.1910 (2)	0.0660 (6)
H3	0.1595	−0.2500	−0.2561	0.079*
C4	0.0635 (2)	−0.2378 (2)	−0.1417 (2)	0.0607 (6)
C5	0.0538 (2)	−0.1719 (2)	−0.0458 (2)	0.0617 (6)
H5	−0.0051	−0.1907	−0.0111	0.074*
C6	0.1300 (2)	−0.07897 (19)	−0.0012 (2)	0.0525 (5)
H6	0.1220	−0.0352	0.0626	0.063*
C7	0.38204 (17)	0.02375 (15)	0.24980 (17)	0.0369 (4)
C8	0.39658 (18)	−0.07796 (15)	0.31288 (18)	0.0418 (4)
C9	0.3646 (2)	−0.09025 (18)	0.4174 (2)	0.0502 (5)
H9	0.3785	−0.1577	0.4612	0.060*
C10	0.3118 (2)	−0.0006 (2)	0.45504 (19)	0.0522 (5)
C11	0.2956 (2)	0.10096 (19)	0.3946 (2)	0.0536 (5)
H11	0.2600	0.1608	0.4212	0.064*
C12	0.3327 (2)	0.11299 (17)	0.29395 (19)	0.0469 (5)
H12	0.3245	0.1824	0.2548	0.056*
C13	−0.0193 (3)	−0.3395 (3)	−0.1891 (3)	0.0923 (10)
H13A	0.0322	−0.4014	−0.1944	0.111*
H13B	−0.0835	−0.3245	−0.2717	0.111*
H13C	−0.0593	−0.3577	−0.1315	0.111*
N1	0.41946 (15)	0.03784 (14)	0.14553 (15)	0.0404 (4)
H1N	0.4704 (18)	−0.0102 (15)	0.136 (2)	0.048*
O1	0.38666 (14)	0.08540 (13)	−0.07316 (14)	0.0563 (4)
O2	0.23685 (14)	0.15510 (12)	0.01841 (14)	0.0510 (4)
Cl1	0.45623 (6)	−0.19221 (5)	0.26176 (6)	0.0665 (2)
Cl2	0.26736 (7)	−0.01719 (8)	0.58308 (6)	0.0843 (3)
S1	0.31493 (4)	0.06739 (4)	0.00383 (5)	0.04119 (17)

	U11	U22	U33	U12	U13	U23
C1	0.0392 (9)	0.0493 (11)	0.0380 (9)	0.0077 (8)	0.0176 (8)	0.0066 (8)
C2	0.0641 (13)	0.0662 (14)	0.0471 (11)	0.0042 (12)	0.0307 (11)	−0.0004 (11)
C3	0.0703 (16)	0.0719 (16)	0.0534 (13)	0.0024 (13)	0.0213 (12)	−0.0156 (12)
C4	0.0484 (12)	0.0623 (14)	0.0561 (13)	0.0007 (11)	0.0035 (10)	−0.0041 (11)
C5	0.0430 (11)	0.0757 (16)	0.0679 (14)	−0.0083 (11)	0.0231 (11)	−0.0012 (13)
C6	0.0468 (11)	0.0630 (14)	0.0561 (12)	−0.0011 (10)	0.0291 (10)	−0.0048 (10)
C7	0.0346 (9)	0.0384 (9)	0.0394 (9)	−0.0021 (8)	0.0162 (8)	0.0008 (8)
C8	0.0428 (10)	0.0384 (10)	0.0455 (10)	0.0012 (8)	0.0188 (8)	0.0020 (8)
C9	0.0547 (12)	0.0511 (12)	0.0464 (11)	−0.0006 (10)	0.0215 (10)	0.0104 (9)
C10	0.0545 (12)	0.0675 (14)	0.0395 (10)	−0.0056 (11)	0.0239 (9)	−0.0030 (10)
C11	0.0616 (13)	0.0539 (12)	0.0516 (12)	0.0034 (11)	0.0287 (11)	−0.0109 (10)
C12	0.0559 (12)	0.0376 (10)	0.0518 (11)	0.0019 (9)	0.0259 (10)	0.0000 (9)
C13	0.0752 (19)	0.086 (2)	0.095 (2)	−0.0204 (17)	0.0106 (16)	−0.0174 (17)
N1	0.0374 (8)	0.0428 (9)	0.0468 (9)	0.0039 (7)	0.0227 (7)	0.0048 (7)
O1	0.0604 (9)	0.0663 (10)	0.0574 (9)	0.0063 (8)	0.0395 (8)	0.0187 (7)
O2	0.0544 (8)	0.0441 (8)	0.0608 (9)	0.0134 (7)	0.0294 (7)	0.0134 (7)
Cl1	0.0877 (5)	0.0423 (3)	0.0857 (4)	0.0176 (3)	0.0513 (4)	0.0088 (3)
Cl2	0.0955 (5)	0.1192 (6)	0.0568 (4)	−0.0017 (5)	0.0500 (4)	0.0039 (4)
S1	0.0430 (3)	0.0440 (3)	0.0447 (3)	0.0062 (2)	0.0259 (2)	0.0116 (2)

C1—C2	1.378 (3)	C8—Cl1	1.7256 (19)
C1—C6	1.387 (3)	C9—C10	1.377 (3)
C1—S1	1.756 (2)	C9—H9	0.9300
C2—C3	1.371 (3)	C10—C11	1.374 (3)
C2—H2	0.9300	C10—Cl2	1.736 (2)
C3—C4	1.385 (3)	C11—C12	1.378 (3)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.389 (3)	C12—H12	0.9300
C4—C13	1.505 (4)	C13—H13A	0.9600
C5—C6	1.380 (3)	C13—H13B	0.9600
C5—H5	0.9300	C13—H13C	0.9600
C6—H6	0.9300	N1—S1	1.6326 (17)
C7—C12	1.389 (3)	N1—H1N	0.852 (15)
C7—C8	1.391 (3)	O1—S1	1.4304 (13)
C7—N1	1.423 (2)	O2—S1	1.4260 (14)
C8—C9	1.385 (3)
C2—C1—C6	120.1 (2)	C8—C9—H9	120.7
C2—C1—S1	120.38 (16)	C11—C10—C9	121.39 (19)
C6—C1—S1	119.53 (16)	C11—C10—Cl2	119.92 (17)
C3—C2—C1	119.6 (2)	C9—C10—Cl2	118.68 (17)
C3—C2—H2	120.2	C10—C11—C12	119.14 (19)
C1—C2—H2	120.2	C10—C11—H11	120.4
C2—C3—C4	121.8 (2)	C12—C11—H11	120.4
C2—C3—H3	119.1	C11—C12—C7	121.42 (19)
C4—C3—H3	119.1	C11—C12—H12	119.3
C3—C4—C5	117.9 (2)	C7—C12—H12	119.3
C3—C4—C13	121.3 (2)	C4—C13—H13A	109.5
C5—C4—C13	120.8 (2)	C4—C13—H13B	109.5
C6—C5—C4	121.2 (2)	H13A—C13—H13B	109.5
C6—C5—H5	119.4	C4—C13—H13C	109.5
C4—C5—H5	119.4	H13A—C13—H13C	109.5
C5—C6—C1	119.5 (2)	H13B—C13—H13C	109.5
C5—C6—H6	120.3	C7—N1—S1	121.08 (12)
C1—C6—H6	120.3	C7—N1—H1N	117.6 (15)
C12—C7—C8	117.85 (17)	S1—N1—H1N	107.0 (15)
C12—C7—N1	120.55 (16)	O2—S1—O1	119.47 (9)
C8—C7—N1	121.58 (16)	O2—S1—N1	106.89 (9)
C9—C8—C7	121.44 (18)	O1—S1—N1	105.80 (9)
C9—C8—Cl1	118.54 (15)	O2—S1—C1	107.95 (9)
C7—C8—Cl1	120.02 (14)	O1—S1—C1	108.83 (9)
C10—C9—C8	118.67 (19)	N1—S1—C1	107.31 (9)
C10—C9—H9	120.7
C6—C1—C2—C3	1.3 (3)	C8—C9—C10—Cl2	178.11 (16)
S1—C1—C2—C3	−178.49 (18)	C9—C10—C11—C12	0.1 (3)
C1—C2—C3—C4	−1.7 (4)	Cl2—C10—C11—C12	179.30 (17)
C2—C3—C4—C5	0.9 (4)	C10—C11—C12—C7	2.2 (3)
C2—C3—C4—C13	−178.4 (2)	C8—C7—C12—C11	−1.9 (3)
C3—C4—C5—C6	0.2 (4)	N1—C7—C12—C11	179.82 (18)
C13—C4—C5—C6	179.5 (2)	C12—C7—N1—S1	−65.1 (2)
C4—C5—C6—C1	−0.6 (3)	C8—C7—N1—S1	116.64 (18)
C2—C1—C6—C5	−0.2 (3)	C7—N1—S1—O2	46.53 (16)
S1—C1—C6—C5	179.58 (17)	C7—N1—S1—O1	174.86 (14)
C12—C7—C8—C9	−0.8 (3)	C7—N1—S1—C1	−69.07 (16)
N1—C7—C8—C9	177.50 (18)	C2—C1—S1—O2	137.68 (17)
C12—C7—C8—Cl1	179.49 (15)	C6—C1—S1—O2	−42.10 (18)
N1—C7—C8—Cl1	−2.2 (3)	C2—C1—S1—O1	6.6 (2)
C7—C8—C9—C10	3.0 (3)	C6—C1—S1—O1	−173.16 (16)
Cl1—C8—C9—C10	−177.23 (17)	C2—C1—S1—N1	−107.43 (17)
C8—C9—C10—C11	−2.7 (3)	C6—C1—S1—N1	72.78 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.85 (2)	2.21 (2)	3.024 (2)	160.(2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.85 (2)	2.21 (2)	3.024 (2)	160 (2)

Symmetry code: (i) .