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

In the title compound, C(13)H(11)Cl(2)NO(2)S, the methyl-substituted aromatic ring is disordered over two positions [occupancy ratio 0.705 (5):0.295 (5)]. The dihedral angles between the two aromatic rings are 74.9 (1) and 71.0 (3)° in the two disorder components. The crystal structure features centrosymmetric 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. (2008 ▶, 2010 ▶); For related structures, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C13H11Cl2NO2S

M = 316.19

Monoclinic,

a = 8.106 (1) Å

b = 14.854 (2) Å

c = 11.772 (1) Å

β = 97.34 (1)°

V = 1405.8 (3) Å3

Z = 4

Cu Kα radiation

μ = 5.52 mm−1

T = 299 K

0.35 × 0.25 × 0.25 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: multi-scan (North et al., 1968 ▶) T min = 0.248, T max = 0.339

5256 measured reflections

2501 independent reflections

2205 reflections with I > 2σ(I)

R int = 0.033

3 standard reflections every 120 min intensity decay: 1.0%

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.098

S = 1.04

2501 reflections

240 parameters

8 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.38 e Å−3

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ▶); 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/S1600536810035166/bt5340sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035166/bt5340Isup2.hkl

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

C13H11Cl2NO2S	F(000) = 648
Mr = 316.19	Dx = 1.494 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 8.106 (1) Å	θ = 4.6–16.5°
b = 14.854 (2) Å	µ = 5.52 mm−1
c = 11.772 (1) Å	T = 299 K
β = 97.34 (1)°	Prism, colourless
V = 1405.8 (3) Å3	0.35 × 0.25 × 0.25 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	2205 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
graphite	θmax = 67.0°, θmin = 4.8°
ω/2θ scans	h = 0→9
Absorption correction: multi-scan (North et al., 1968)	k = −17→17
Tmin = 0.248, Tmax = 0.339	l = −14→13
5256 measured reflections	3 standard reflections every 120 min
2501 independent reflections	intensity decay: 1.0%

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)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.098	w = 1/[σ2(Fo2) + (0.0521P)2 + 0.4627P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.005
2501 reflections	Δρmax = 0.44 e Å−3
240 parameters	Δρmin = −0.38 e Å−3
8 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0021 (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	Occ. (<1)
C1	0.1368 (2)	0.33703 (12)	0.20574 (15)	0.0386 (4)
C2	0.2961 (3)	0.36013 (12)	0.18389 (16)	0.0404 (4)
C3	0.4340 (3)	0.31932 (15)	0.24250 (19)	0.0502 (5)
H3	0.5403	0.3342	0.2269	0.060*
C4	0.4113 (3)	0.25585 (15)	0.3250 (2)	0.0533 (5)
C5	0.2555 (3)	0.23232 (14)	0.34875 (19)	0.0520 (5)
H5	0.2430	0.1899	0.4051	0.062*
C6	0.1183 (3)	0.27211 (13)	0.28857 (17)	0.0450 (5)
H6	0.0124	0.2556	0.3032	0.054*
C7A	−0.1071 (5)	0.5236 (2)	0.2565 (3)	0.0446 (8)	0.705 (5)
C8A	0.0002 (5)	0.5685 (2)	0.3379 (4)	0.0532 (9)	0.705 (5)
C9A	−0.072 (2)	0.6089 (7)	0.4284 (7)	0.071 (3)	0.705 (5)
H9A	−0.0061	0.6448	0.4807	0.085*	0.705 (5)
C10A	−0.2337 (8)	0.5970 (3)	0.4412 (4)	0.0903 (16)	0.705 (5)
H10A	−0.2750	0.6187	0.5061	0.108*	0.705 (5)
C11A	−0.3369 (8)	0.5525 (4)	0.3577 (6)	0.0851 (17)	0.705 (5)
H11A	−0.4495	0.5469	0.3644	0.102*	0.705 (5)
C12A	−0.2749 (7)	0.5167 (3)	0.2651 (5)	0.0608 (12)	0.705 (5)
H12A	−0.3455	0.4877	0.2081	0.073*	0.705 (5)
C13A	0.1816 (13)	0.5795 (9)	0.3311 (9)	0.074 (3)	0.705 (5)
H13A	0.1967	0.6110	0.2619	0.088*	0.705 (5)
H13B	0.2331	0.5214	0.3309	0.088*	0.705 (5)
H13C	0.2316	0.6134	0.3960	0.088*	0.705 (5)
N1	−0.0460 (2)	0.49066 (12)	0.15829 (14)	0.0462 (4)
H1N	0.003 (3)	0.5230 (16)	0.1141 (19)	0.055*
O1	−0.1805 (2)	0.34262 (12)	0.17683 (16)	0.0629 (4)
O2	−0.0363 (2)	0.37672 (10)	0.01067 (12)	0.0560 (4)
Cl1	0.32844 (7)	0.44230 (4)	0.08450 (4)	0.05248 (18)
Cl2	0.58543 (10)	0.20713 (6)	0.40131 (8)	0.0887 (3)
S1	−0.04615 (6)	0.38428 (3)	0.13094 (4)	0.04322 (17)
C7B	−0.0109 (13)	0.5386 (5)	0.2733 (7)	0.043 (2)	0.295 (5)
C8B	−0.1310 (11)	0.5537 (5)	0.3435 (6)	0.055 (2)	0.295 (5)
C9B	−0.080 (4)	0.5925 (14)	0.4520 (14)	0.052 (4)	0.295 (5)
H9B	−0.1519	0.5919	0.5073	0.062*	0.295 (5)
C10B	0.0727 (13)	0.6305 (6)	0.4773 (8)	0.068 (3)	0.295 (5)
H10B	0.0964	0.6653	0.5429	0.082*	0.295 (5)
C11B	0.1903 (13)	0.6177 (7)	0.4071 (10)	0.074 (3)	0.295 (5)
H11B	0.2974	0.6398	0.4274	0.088*	0.295 (5)
C12B	0.151 (3)	0.5715 (16)	0.3043 (19)	0.054 (4)	0.295 (5)
H12B	0.2317	0.5624	0.2561	0.064*	0.295 (5)
C13B	−0.3078 (15)	0.5262 (10)	0.3116 (11)	0.067 (4)	0.295 (5)
H13D	−0.3132	0.4623	0.2989	0.081*	0.295 (5)
H13E	−0.3532	0.5569	0.2429	0.081*	0.295 (5)
H13F	−0.3709	0.5415	0.3725	0.081*	0.295 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0406 (10)	0.0357 (9)	0.0390 (9)	−0.0031 (8)	0.0029 (7)	−0.0023 (7)
C2	0.0429 (11)	0.0354 (9)	0.0432 (10)	−0.0030 (8)	0.0065 (8)	−0.0020 (8)
C3	0.0395 (11)	0.0490 (12)	0.0620 (13)	−0.0002 (9)	0.0059 (9)	−0.0007 (10)
C4	0.0516 (13)	0.0457 (11)	0.0600 (12)	0.0073 (10)	−0.0036 (10)	0.0029 (10)
C5	0.0623 (14)	0.0420 (10)	0.0511 (11)	−0.0001 (10)	0.0051 (10)	0.0077 (9)
C6	0.0460 (11)	0.0422 (10)	0.0474 (11)	−0.0066 (9)	0.0082 (8)	0.0013 (8)
C7A	0.050 (2)	0.0363 (16)	0.0468 (19)	0.0050 (15)	0.0028 (16)	0.0013 (13)
C8A	0.060 (3)	0.0448 (18)	0.053 (2)	0.0001 (16)	0.0025 (18)	0.0001 (16)
C9A	0.111 (5)	0.051 (5)	0.050 (4)	−0.003 (3)	0.012 (4)	−0.002 (4)
C10A	0.110 (4)	0.084 (3)	0.085 (3)	0.007 (3)	0.043 (3)	−0.020 (2)
C11A	0.071 (3)	0.084 (4)	0.109 (5)	0.005 (3)	0.047 (3)	−0.022 (3)
C12A	0.056 (3)	0.053 (2)	0.074 (4)	0.0074 (18)	0.013 (2)	−0.007 (2)
C13A	0.059 (4)	0.080 (5)	0.077 (7)	−0.011 (3)	−0.006 (4)	−0.019 (4)
N1	0.0526 (11)	0.0438 (9)	0.0424 (9)	0.0006 (8)	0.0069 (7)	0.0035 (7)
O1	0.0401 (9)	0.0595 (9)	0.0888 (12)	−0.0069 (7)	0.0073 (8)	0.0146 (8)
O2	0.0650 (11)	0.0557 (9)	0.0431 (8)	−0.0070 (7)	−0.0094 (7)	−0.0048 (6)
Cl1	0.0507 (3)	0.0533 (3)	0.0544 (3)	−0.0078 (2)	0.0107 (2)	0.0094 (2)
Cl2	0.0639 (4)	0.0861 (5)	0.1097 (6)	0.0179 (4)	−0.0134 (4)	0.0310 (4)
S1	0.0373 (3)	0.0435 (3)	0.0472 (3)	−0.00531 (19)	−0.00115 (19)	0.00201 (19)
C7B	0.062 (7)	0.032 (4)	0.033 (4)	0.002 (4)	−0.001 (4)	−0.008 (3)
C8B	0.068 (6)	0.045 (4)	0.054 (5)	0.007 (4)	0.017 (4)	−0.002 (3)
C9B	0.091 (10)	0.035 (7)	0.033 (6)	0.004 (6)	0.022 (6)	0.007 (5)
C10B	0.093 (7)	0.053 (5)	0.057 (5)	0.004 (5)	0.004 (5)	−0.020 (4)
C11B	0.064 (6)	0.075 (6)	0.076 (6)	−0.003 (5)	−0.014 (5)	−0.030 (5)
C12B	0.065 (11)	0.046 (6)	0.047 (7)	−0.006 (6)	−0.004 (7)	−0.014 (5)
C13B	0.048 (8)	0.088 (10)	0.069 (10)	−0.002 (6)	0.021 (6)	−0.021 (7)

C1—C2	1.391 (3)	C12A—H12A	0.9300
C1—C6	1.393 (3)	C13A—H13A	0.9600
C1—S1	1.770 (2)	C13A—H13B	0.9600
C2—C3	1.377 (3)	C13A—H13C	0.9600
C2—Cl1	1.7337 (19)	N1—C7B	1.524 (9)
C3—C4	1.382 (3)	N1—S1	1.6125 (18)
C3—H3	0.9300	N1—H1N	0.844 (17)
C4—C5	1.373 (3)	O1—S1	1.4183 (17)
C4—Cl2	1.732 (2)	O2—S1	1.4326 (15)
C5—C6	1.373 (3)	C7B—C8B	1.374 (11)
C5—H5	0.9300	C7B—C12B	1.402 (17)
C6—H6	0.9300	C8B—C9B	1.415 (16)
C7A—C12A	1.381 (7)	C8B—C13B	1.492 (13)
C7A—C8A	1.381 (5)	C9B—C10B	1.36 (3)
C7A—N1	1.403 (4)	C9B—H9B	0.9300
C8A—C9A	1.413 (11)	C10B—C11B	1.352 (15)
C8A—C13A	1.492 (11)	C10B—H10B	0.9300
C9A—C10A	1.350 (15)	C11B—C12B	1.393 (16)
C9A—H9A	0.9300	C11B—H11B	0.9300
C10A—C11A	1.375 (8)	C12B—H12B	0.9300
C10A—H10A	0.9300	C13B—H13D	0.9600
C11A—C12A	1.366 (7)	C13B—H13E	0.9600
C11A—H11A	0.9300	C13B—H13F	0.9600
C2—C1—C6	119.02 (18)	C8A—C13A—H13C	109.5
C2—C1—S1	123.26 (14)	H13A—C13A—H13C	109.5
C6—C1—S1	117.69 (15)	H13B—C13A—H13C	109.5
C3—C2—C1	120.80 (19)	C7A—N1—C7B	31.8 (3)
C3—C2—Cl1	117.70 (16)	C7A—N1—S1	121.00 (19)
C1—C2—Cl1	121.49 (15)	C7B—N1—S1	129.1 (3)
C2—C3—C4	118.6 (2)	C7A—N1—H1N	123.6 (17)
C2—C3—H3	120.7	C7B—N1—H1N	103.4 (17)
C4—C3—H3	120.7	S1—N1—H1N	115.0 (17)
C5—C4—C3	121.7 (2)	O1—S1—O2	118.99 (10)
C5—C4—Cl2	119.84 (18)	O1—S1—N1	109.42 (11)
C3—C4—Cl2	118.43 (18)	O2—S1—N1	105.99 (9)
C4—C5—C6	119.4 (2)	O1—S1—C1	105.83 (10)
C4—C5—H5	120.3	O2—S1—C1	108.16 (10)
C6—C5—H5	120.3	N1—S1—C1	108.06 (9)
C5—C6—C1	120.5 (2)	C8B—C7B—C12B	119.8 (13)
C5—C6—H6	119.8	C8B—C7B—N1	123.0 (9)
C1—C6—H6	119.8	C12B—C7B—N1	117.1 (11)
C12A—C7A—C8A	121.6 (4)	C7B—C8B—C9B	117.4 (14)
C12A—C7A—N1	119.3 (4)	C7B—C8B—C13B	122.4 (9)
C8A—C7A—N1	118.9 (4)	C9B—C8B—C13B	120.1 (14)
C7A—C8A—C9A	116.3 (7)	C10B—C9B—C8B	121.5 (16)
C7A—C8A—C13A	123.6 (5)	C10B—C9B—H9B	119.2
C9A—C8A—C13A	120.0 (7)	C8B—C9B—H9B	119.2
C10A—C9A—C8A	122.0 (8)	C11B—C10B—C9B	120.1 (10)
C10A—C9A—H9A	119.0	C11B—C10B—H10B	120.0
C8A—C9A—H9A	119.0	C9B—C10B—H10B	120.0
C9A—C10A—C11A	119.6 (5)	C10B—C11B—C12B	119.9 (13)
C9A—C10A—H10A	120.2	C10B—C11B—H11B	120.1
C11A—C10A—H10A	120.2	C12B—C11B—H11B	120.1
C12A—C11A—C10A	120.4 (6)	C11B—C12B—C7B	120.1 (18)
C12A—C11A—H11A	119.8	C11B—C12B—H12B	120.0
C10A—C11A—H11A	119.8	C7B—C12B—H12B	120.0
C11A—C12A—C7A	119.7 (6)	C8B—C13B—H13D	109.5
C11A—C12A—H12A	120.1	C8B—C13B—H13E	109.5
C7A—C12A—H12A	120.1	H13D—C13B—H13E	109.5
C8A—C13A—H13A	109.5	C8B—C13B—H13F	109.5
C8A—C13A—H13B	109.5	H13D—C13B—H13F	109.5
H13A—C13A—H13B	109.5	H13E—C13B—H13F	109.5
C6—C1—C2—C3	0.4 (3)	C7A—N1—S1—O1	29.7 (3)
S1—C1—C2—C3	−178.13 (16)	C7B—N1—S1—O1	67.6 (5)
C6—C1—C2—Cl1	−178.41 (15)	C7A—N1—S1—O2	159.2 (2)
S1—C1—C2—Cl1	3.1 (2)	C7B—N1—S1—O2	−162.9 (5)
C1—C2—C3—C4	−1.0 (3)	C7A—N1—S1—C1	−85.1 (2)
Cl1—C2—C3—C4	177.79 (16)	C7B—N1—S1—C1	−47.2 (5)
C2—C3—C4—C5	0.5 (3)	C2—C1—S1—O1	179.13 (16)
C2—C3—C4—Cl2	−178.15 (17)	C6—C1—S1—O1	0.62 (18)
C3—C4—C5—C6	0.6 (3)	C2—C1—S1—O2	50.59 (18)
Cl2—C4—C5—C6	179.28 (17)	C6—C1—S1—O2	−127.93 (15)
C4—C5—C6—C1	−1.3 (3)	C2—C1—S1—N1	−63.73 (18)
C2—C1—C6—C5	0.8 (3)	C6—C1—S1—N1	117.75 (16)
S1—C1—C6—C5	179.39 (16)	C7A—N1—C7B—C8B	1.1 (5)
C12A—C7A—C8A—C9A	−1.7 (7)	S1—N1—C7B—C8B	−86.0 (8)
N1—C7A—C8A—C9A	173.1 (5)	C7A—N1—C7B—C12B	−176.0 (15)
C12A—C7A—C8A—C13A	−178.6 (8)	S1—N1—C7B—C12B	96.9 (13)
N1—C7A—C8A—C13A	−3.8 (8)	C12B—C7B—C8B—C9B	−7.9 (19)
C7A—C8A—C9A—C10A	6.4 (11)	N1—C7B—C8B—C9B	175.0 (12)
C13A—C8A—C9A—C10A	−176.6 (9)	C12B—C7B—C8B—C13B	175.7 (15)
C8A—C9A—C10A—C11A	−7.2 (13)	N1—C7B—C8B—C13B	−1.4 (12)
C9A—C10A—C11A—C12A	3.2 (11)	C7B—C8B—C9B—C10B	14 (3)
C10A—C11A—C12A—C7A	1.3 (9)	C13B—C8B—C9B—C10B	−170.0 (16)
C8A—C7A—C12A—C11A	−2.0 (7)	C8B—C9B—C10B—C11B	−12 (3)
N1—C7A—C12A—C11A	−176.8 (5)	C9B—C10B—C11B—C12B	5(2)
C12A—C7A—N1—C7B	177.2 (8)	C10B—C11B—C12B—C7B	0(3)
C8A—C7A—N1—C7B	2.3 (5)	C8B—C7B—C12B—C11B	1(2)
C12A—C7A—N1—S1	−67.5 (4)	N1—C7B—C12B—C11B	178.6 (13)
C8A—C7A—N1—S1	117.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.84 (2)	2.13 (2)	2.936 (2)	159 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.84 (2)	2.13 (2)	2.936 (2)	159 (2)

Symmetry code: (i) .