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

In the title compound, C(13)H(11)Cl(2)NO(2)S, the conformations of the N-C bonds in the C-SO(2)-NH-C segments have gauche torsions with respect to the S=O bonds. The dihedral angle between the two benzene rings is 68.6 (1)°. The crystal structure features inversion dimers linked by pairs of N-H⋯O hydrogen bonds.

Related literature

For the preparation of the title compound, see: Savitha & Gowda (2006 ▶). For our studies of the effect of substituents on the structures of N-(ar­yl)aryl­sulfonamides, see: Gowda et al. (2010 ▶). For related structures, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C13H11Cl2NO2S

M = 316.19

Monoclinic,

a = 7.9031 (7) Å

b = 14.507 (1) Å

c = 12.715 (1) Å

β = 99.895 (8)°

V = 1436.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.59 mm−1

T = 299 K

0.36 × 0.24 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.815, T max = 0.891

5737 measured reflections

2915 independent reflections

2389 reflections with I > 2σ(I)

R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.097

S = 1.03

2915 reflections

176 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.49 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 datablocks I, global. DOI: 10.1107/S1600536810020106/bq2216sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810020106/bq2216Isup2.hkl

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

C13H11Cl2NO2S	F(000) = 648
Mr = 316.19	Dx = 1.462 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3053 reflections
a = 7.9031 (7) Å	θ = 2.6–27.8°
b = 14.507 (1) Å	µ = 0.59 mm−1
c = 12.715 (1) Å	T = 299 K
β = 99.895 (8)°	Prism, colorless
V = 1436.1 (2) Å3	0.36 × 0.24 × 0.20 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2915 independent reflections
Radiation source: fine-focus sealed tube	2389 reflections with I > 2σ(I)
graphite	Rint = 0.012
Rotation method data acquisition using ω and phi scans.	θmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −9→7
Tmin = 0.815, Tmax = 0.891	k = −18→15
5737 measured reflections	l = −14→15

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0451P)2 + 0.717P] where P = (Fo2 + 2Fc2)/3
2915 reflections	(Δ/σ)max = 0.001
176 parameters	Δρmax = 0.41 e Å−3
1 restraint	Δρmin = −0.49 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	0.6418 (2)	0.33869 (13)	0.20486 (15)	0.0350 (4)
C2	0.8068 (2)	0.36037 (14)	0.18846 (16)	0.0402 (4)
C3	0.9482 (3)	0.31950 (15)	0.24999 (18)	0.0509 (5)
H3	1.0586	0.3336	0.2389	0.061*
C4	0.9232 (3)	0.25777 (15)	0.32759 (18)	0.0520 (5)
C5	0.7617 (3)	0.23604 (15)	0.34720 (17)	0.0502 (5)
H5	0.7475	0.1948	0.4010	0.060*
C6	0.6213 (3)	0.27706 (14)	0.28493 (16)	0.0420 (4)
H6	0.5114	0.2631	0.2970	0.050*
C7	0.4604 (3)	0.53438 (14)	0.24891 (17)	0.0442 (5)
C8	0.3109 (3)	0.53560 (16)	0.2914 (2)	0.0549 (6)
H8	0.2117	0.5089	0.2538	0.066*
C9	0.3078 (4)	0.57624 (18)	0.3896 (2)	0.0714 (8)
C10	0.4569 (5)	0.6157 (2)	0.4429 (2)	0.0811 (9)
H10	0.4570	0.6428	0.5092	0.097*
C11	0.6042 (4)	0.6158 (2)	0.4005 (2)	0.0768 (8)
H11	0.7026	0.6439	0.4373	0.092*
C12	0.6080 (3)	0.57441 (17)	0.3031 (2)	0.0589 (6)
H12	0.7087	0.5736	0.2745	0.071*
C13	0.1436 (6)	0.5793 (3)	0.4345 (4)	0.1194 (15)
H13A	0.0657	0.5334	0.4000	0.143*
H13B	0.0922	0.6392	0.4223	0.143*
H13C	0.1682	0.5672	0.5098	0.143*
N1	0.4582 (2)	0.49567 (12)	0.14485 (14)	0.0433 (4)
H1N	0.516 (3)	0.5237 (15)	0.1041 (16)	0.052*
O1	0.46312 (19)	0.37240 (11)	0.01548 (11)	0.0509 (4)
O2	0.31399 (17)	0.34804 (11)	0.16821 (13)	0.0538 (4)
S1	0.45443 (6)	0.38552 (3)	0.12621 (4)	0.03929 (14)
Cl1	0.84366 (7)	0.44023 (5)	0.09354 (5)	0.06074 (19)
Cl2	1.10203 (10)	0.20696 (6)	0.40428 (7)	0.0889 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0317 (9)	0.0341 (9)	0.0383 (10)	−0.0004 (7)	0.0031 (7)	−0.0038 (8)
C2	0.0354 (9)	0.0417 (10)	0.0439 (11)	−0.0010 (8)	0.0076 (8)	−0.0012 (8)
C3	0.0337 (10)	0.0520 (12)	0.0659 (14)	0.0041 (9)	0.0056 (9)	−0.0013 (11)
C4	0.0461 (12)	0.0456 (12)	0.0579 (13)	0.0081 (9)	−0.0093 (10)	−0.0004 (10)
C5	0.0605 (13)	0.0409 (11)	0.0462 (12)	−0.0013 (10)	0.0006 (10)	0.0059 (9)
C6	0.0418 (10)	0.0390 (10)	0.0448 (11)	−0.0047 (8)	0.0068 (8)	−0.0016 (8)
C7	0.0510 (12)	0.0348 (10)	0.0459 (11)	0.0067 (9)	0.0059 (9)	0.0047 (9)
C8	0.0598 (14)	0.0464 (12)	0.0615 (14)	0.0002 (10)	0.0194 (11)	0.0008 (11)
C9	0.100 (2)	0.0550 (15)	0.0682 (17)	0.0041 (14)	0.0391 (16)	0.0008 (13)
C10	0.126 (3)	0.0642 (17)	0.0560 (16)	0.0059 (18)	0.0231 (17)	−0.0095 (14)
C11	0.093 (2)	0.0638 (17)	0.0661 (17)	−0.0007 (15)	−0.0074 (16)	−0.0131 (14)
C12	0.0566 (14)	0.0536 (13)	0.0639 (15)	0.0025 (11)	0.0033 (11)	−0.0041 (11)
C13	0.143 (4)	0.114 (3)	0.125 (3)	−0.007 (3)	0.089 (3)	−0.019 (2)
N1	0.0453 (9)	0.0410 (9)	0.0441 (10)	0.0038 (7)	0.0092 (7)	0.0050 (7)
O1	0.0512 (9)	0.0578 (9)	0.0401 (8)	−0.0029 (7)	−0.0021 (6)	−0.0060 (7)
O2	0.0320 (7)	0.0580 (9)	0.0711 (10)	−0.0050 (7)	0.0083 (7)	0.0028 (8)
S1	0.0313 (2)	0.0429 (3)	0.0420 (3)	−0.00170 (19)	0.00161 (18)	−0.0009 (2)
Cl1	0.0471 (3)	0.0713 (4)	0.0669 (4)	−0.0056 (3)	0.0187 (3)	0.0193 (3)
Cl2	0.0670 (4)	0.0819 (5)	0.1043 (6)	0.0210 (4)	−0.0233 (4)	0.0194 (4)

C1—C6	1.385 (3)	C8—H8	0.9300
C1—C2	1.392 (3)	C9—C10	1.379 (5)
C1—S1	1.7734 (18)	C9—C13	1.505 (4)
C2—C3	1.383 (3)	C10—C11	1.365 (5)
C2—Cl1	1.733 (2)	C10—H10	0.9300
C3—C4	1.372 (3)	C11—C12	1.381 (4)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.379 (3)	C12—H12	0.9300
C4—Cl2	1.737 (2)	C13—H13A	0.9600
C5—C6	1.382 (3)	C13—H13B	0.9600
C5—H5	0.9300	C13—H13C	0.9600
C6—H6	0.9300	N1—S1	1.6150 (18)
C7—C12	1.377 (3)	N1—H1N	0.852 (10)
C7—C8	1.381 (3)	O1—S1	1.4340 (15)
C7—N1	1.435 (3)	O2—S1	1.4201 (15)
C8—C9	1.385 (4)
C6—C1—C2	119.14 (17)	C8—C9—C13	120.3 (3)
C6—C1—S1	118.04 (14)	C11—C10—C9	121.4 (3)
C2—C1—S1	122.82 (15)	C11—C10—H10	119.3
C3—C2—C1	120.37 (19)	C9—C10—H10	119.3
C3—C2—Cl1	117.66 (16)	C10—C11—C12	120.3 (3)
C1—C2—Cl1	121.96 (15)	C10—C11—H11	119.8
C4—C3—C2	118.96 (19)	C12—C11—H11	119.8
C4—C3—H3	120.5	C7—C12—C11	119.0 (3)
C2—C3—H3	120.5	C7—C12—H12	120.5
C3—C4—C5	122.14 (19)	C11—C12—H12	120.5
C3—C4—Cl2	118.47 (18)	C9—C13—H13A	109.5
C5—C4—Cl2	119.39 (18)	C9—C13—H13B	109.5
C4—C5—C6	118.4 (2)	H13A—C13—H13B	109.5
C4—C5—H5	120.8	C9—C13—H13C	109.5
C6—C5—H5	120.8	H13A—C13—H13C	109.5
C5—C6—C1	121.01 (19)	H13B—C13—H13C	109.5
C5—C6—H6	119.5	C7—N1—S1	121.30 (14)
C1—C6—H6	119.5	C7—N1—H1N	116.9 (16)
C12—C7—C8	120.5 (2)	S1—N1—H1N	112.4 (16)
C12—C7—N1	120.1 (2)	O2—S1—O1	119.39 (9)
C8—C7—N1	119.3 (2)	O2—S1—N1	108.64 (9)
C7—C8—C9	120.5 (3)	O1—S1—N1	105.82 (9)
C7—C8—H8	119.8	O2—S1—C1	105.78 (9)
C9—C8—H8	119.8	O1—S1—C1	109.07 (9)
C10—C9—C8	118.3 (3)	N1—S1—C1	107.68 (9)
C10—C9—C13	121.4 (3)
C6—C1—C2—C3	1.2 (3)	C8—C9—C10—C11	0.6 (4)
S1—C1—C2—C3	−177.90 (16)	C13—C9—C10—C11	−177.7 (3)
C6—C1—C2—Cl1	−177.39 (15)	C9—C10—C11—C12	−1.3 (5)
S1—C1—C2—Cl1	3.5 (2)	C8—C7—C12—C11	0.0 (4)
C1—C2—C3—C4	−0.3 (3)	N1—C7—C12—C11	176.4 (2)
Cl1—C2—C3—C4	178.37 (17)	C10—C11—C12—C7	1.0 (4)
C2—C3—C4—C5	−0.9 (3)	C12—C7—N1—S1	107.6 (2)
C2—C3—C4—Cl2	180.00 (17)	C8—C7—N1—S1	−76.0 (2)
C3—C4—C5—C6	1.1 (3)	C7—N1—S1—O2	53.93 (18)
Cl2—C4—C5—C6	−179.77 (16)	C7—N1—S1—O1	−176.73 (15)
C4—C5—C6—C1	−0.1 (3)	C7—N1—S1—C1	−60.20 (18)
C2—C1—C6—C5	−1.0 (3)	C6—C1—S1—O2	1.58 (18)
S1—C1—C6—C5	178.18 (16)	C2—C1—S1—O2	−179.27 (16)
C12—C7—C8—C9	−0.7 (3)	C6—C1—S1—O1	−128.01 (16)
N1—C7—C8—C9	−177.1 (2)	C2—C1—S1—O1	51.14 (18)
C7—C8—C9—C10	0.4 (4)	C6—C1—S1—N1	117.60 (16)
C7—C8—C9—C13	178.6 (3)	C2—C1—S1—N1	−63.25 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.85 (1)	2.17 (1)	2.940 (2)	151 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.85 (1)	2.17 (1)	2.940 (2)	151 (2)

Symmetry code: (i) .