N-(2,5-Dichloro-phen-yl)-4-methyl-benzene-sulfonamide.

In the title compound, C(13)H(11)Cl(2)NO(2)S, the N-C bond in the C-SO(2)-NH-C segment has gauche torsion angles with respect to the S=O bonds. The mol-ecule is bent at the S atom with an C-SO(2)-NH-C torsion angle of 62.1 (2)°. Furthermore, the conformation of the N-H bond is syn to the ortho-chloro group in the adjacent benzene ring. The benzene rings are tilted by 67.8 (1)° relative to each other. The crystal structure features dimers linked by N-H⋯O hydrogen bonds. An intra-molecular N-H⋯Cl hydrogen bond is also observed.

Related literature

For our study of the effect of substituents on the structures of N-(ar­yl)aryl­sulfonamides, see: Gowda et al. (2009 ▶; 2010a ▶,b ▶). For related structures, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C13H11Cl2NO2S

M = 316.19

Monoclinic,

a = 9.075 (1) Å

b = 14.232 (2) Å

c = 10.773 (1) Å

β = 90.49 (1)°

V = 1391.3 (3) Å3

Z = 4

Cu Kα radiation

μ = 5.58 mm−1

T = 299 K

0.45 × 0.40 × 0.40 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

3316 measured reflections

2474 independent reflections

2268 reflections with I > 2σ(I)

R int = 0.053

3 standard reflections every 120 min intensity decay: 0.5%

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.141

S = 1.14

2474 reflections

177 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.49 e Å−3

Δρmin = −0.43 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/S1600536810050270/bq2259sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050270/bq2259Isup2.hkl

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

C13H11Cl2NO2S	F(000) = 648
Mr = 316.19	Dx = 1.509 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 9.075 (1) Å	θ = 4.9–15.1°
b = 14.232 (2) Å	µ = 5.58 mm−1
c = 10.773 (1) Å	T = 299 K
β = 90.49 (1)°	Prism, light-brown
V = 1391.3 (3) Å3	0.45 × 0.40 × 0.40 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.053
Radiation source: fine-focus sealed tube	θmax = 66.9°, θmin = 4.9°
graphite	h = −10→3
ω/2θ scans	k = −16→0
3316 measured reflections	l = −12→12
2474 independent reflections	3 standard reflections every 120 min
2268 reflections with I > 2σ(I)	intensity decay: 0.5%

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)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.141	w = 1/[σ2(Fo2) + (0.0718P)2 + 1.1523P] where P = (Fo2 + 2Fc2)/3
S = 1.14	(Δ/σ)max = 0.012
2474 reflections	Δρmax = 0.49 e Å−3
177 parameters	Δρmin = −0.43 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: 0.0121 (10)

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	0.8106 (3)	0.44716 (18)	0.0868 (3)	0.0336 (6)
C2	0.9194 (4)	0.4179 (3)	0.1653 (4)	0.0740 (13)
H2	0.9349	0.4487	0.2404	0.089*
C3	1.0068 (4)	0.3426 (4)	0.1335 (4)	0.0804 (14)
H3	1.0788	0.3220	0.1891	0.096*
C4	0.9905 (3)	0.2980 (2)	0.0237 (3)	0.0487 (7)
C5	0.8815 (5)	0.3281 (3)	−0.0543 (4)	0.0720 (12)
H5	0.8676	0.2978	−0.1300	0.086*
C6	0.7909 (4)	0.4027 (3)	−0.0237 (3)	0.0635 (10)
H6	0.7172	0.4222	−0.0783	0.076*
C7	0.5866 (3)	0.44233 (18)	0.3242 (2)	0.0324 (6)
C8	0.5187 (3)	0.35642 (19)	0.3458 (3)	0.0372 (6)
C9	0.5373 (4)	0.3097 (2)	0.4565 (3)	0.0531 (8)
H9	0.4892	0.2529	0.4698	0.064*
C10	0.6268 (4)	0.3467 (3)	0.5475 (3)	0.0566 (9)
H10	0.6418	0.3149	0.6219	0.068*
C11	0.6936 (3)	0.4315 (2)	0.5263 (3)	0.0470 (7)
C12	0.6738 (3)	0.47999 (19)	0.4179 (3)	0.0407 (6)
H12	0.7188	0.5381	0.4071	0.049*
C13	1.0874 (5)	0.2165 (3)	−0.0099 (4)	0.0756 (12)
H13A	1.1548	0.2039	0.0572	0.091*
H13B	1.1417	0.2314	−0.0833	0.091*
H13C	1.0275	0.1620	−0.0250	0.091*
N1	0.5612 (2)	0.49095 (16)	0.2114 (2)	0.0359 (5)
H1N	0.505 (3)	0.463 (2)	0.161 (3)	0.043*
O1	0.6219 (2)	0.57604 (14)	0.0235 (2)	0.0505 (6)
O2	0.7747 (2)	0.59971 (14)	0.2118 (2)	0.0520 (6)
Cl1	0.40649 (9)	0.30737 (5)	0.23286 (7)	0.0535 (3)
Cl2	0.80520 (12)	0.47898 (8)	0.64157 (9)	0.0756 (4)
S1	0.69445 (7)	0.53899 (4)	0.13097 (6)	0.0357 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0304 (12)	0.0293 (13)	0.0411 (14)	−0.0017 (10)	0.0051 (10)	0.0042 (11)
C2	0.0472 (19)	0.109 (3)	0.066 (2)	0.033 (2)	−0.0193 (17)	−0.034 (2)
C3	0.056 (2)	0.116 (4)	0.069 (2)	0.048 (2)	−0.0184 (18)	−0.017 (2)
C4	0.0414 (15)	0.0433 (17)	0.0616 (19)	0.0084 (13)	0.0124 (14)	0.0074 (15)
C5	0.080 (3)	0.075 (3)	0.060 (2)	0.036 (2)	−0.0136 (19)	−0.0246 (19)
C6	0.072 (2)	0.071 (2)	0.0469 (18)	0.0357 (19)	−0.0144 (16)	−0.0109 (16)
C7	0.0331 (12)	0.0260 (12)	0.0384 (14)	0.0027 (10)	0.0108 (10)	0.0014 (10)
C8	0.0434 (14)	0.0303 (14)	0.0381 (14)	−0.0049 (11)	0.0068 (11)	−0.0025 (11)
C9	0.071 (2)	0.0378 (16)	0.0504 (17)	−0.0163 (14)	0.0031 (15)	0.0113 (13)
C10	0.075 (2)	0.053 (2)	0.0426 (16)	−0.0126 (17)	−0.0025 (15)	0.0120 (14)
C11	0.0492 (17)	0.0501 (18)	0.0415 (16)	−0.0054 (14)	−0.0011 (13)	−0.0010 (13)
C12	0.0423 (14)	0.0308 (14)	0.0493 (16)	−0.0072 (11)	0.0039 (12)	−0.0003 (12)
C13	0.069 (2)	0.059 (2)	0.099 (3)	0.029 (2)	0.019 (2)	0.004 (2)
N1	0.0340 (12)	0.0317 (12)	0.0419 (13)	−0.0019 (9)	0.0056 (9)	0.0061 (10)
O1	0.0587 (12)	0.0381 (11)	0.0547 (13)	0.0088 (9)	0.0056 (10)	0.0209 (10)
O2	0.0611 (13)	0.0322 (10)	0.0628 (14)	−0.0158 (9)	0.0111 (11)	−0.0046 (10)
Cl1	0.0703 (5)	0.0432 (5)	0.0469 (4)	−0.0217 (3)	0.0009 (3)	−0.0060 (3)
Cl2	0.0841 (7)	0.0846 (7)	0.0576 (6)	−0.0247 (5)	−0.0215 (5)	0.0002 (5)
S1	0.0393 (4)	0.0232 (4)	0.0449 (4)	−0.0015 (2)	0.0083 (3)	0.0069 (3)

C1—C6	1.358 (4)	C8—Cl1	1.727 (3)
C1—C2	1.360 (4)	C9—C10	1.373 (5)
C1—S1	1.748 (3)	C9—H9	0.9300
C2—C3	1.378 (5)	C10—C11	1.370 (5)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.350 (5)	C11—C12	1.367 (4)
C3—H3	0.9300	C11—Cl2	1.733 (3)
C4—C5	1.362 (5)	C12—H12	0.9300
C4—C13	1.502 (4)	C13—H13A	0.9600
C5—C6	1.385 (5)	C13—H13B	0.9600
C5—H5	0.9300	C13—H13C	0.9600
C6—H6	0.9300	N1—S1	1.643 (2)
C7—C12	1.385 (4)	N1—H1N	0.847 (18)
C7—C8	1.390 (4)	O1—S1	1.428 (2)
C7—N1	1.415 (3)	O2—S1	1.423 (2)
C8—C9	1.375 (4)
C6—C1—C2	119.4 (3)	C8—C9—H9	120.0
C6—C1—S1	120.8 (2)	C11—C10—C9	118.6 (3)
C2—C1—S1	119.7 (2)	C11—C10—H10	120.7
C1—C2—C3	119.9 (3)	C9—C10—H10	120.7
C1—C2—H2	120.0	C12—C11—C10	122.2 (3)
C3—C2—H2	120.0	C12—C11—Cl2	119.1 (2)
C4—C3—C2	121.7 (3)	C10—C11—Cl2	118.7 (2)
C4—C3—H3	119.2	C11—C12—C7	119.8 (3)
C2—C3—H3	119.2	C11—C12—H12	120.1
C3—C4—C5	117.8 (3)	C7—C12—H12	120.1
C3—C4—C13	121.0 (3)	C4—C13—H13A	109.5
C5—C4—C13	121.2 (3)	C4—C13—H13B	109.5
C4—C5—C6	121.6 (3)	H13A—C13—H13B	109.5
C4—C5—H5	119.2	C4—C13—H13C	109.5
C6—C5—H5	119.2	H13A—C13—H13C	109.5
C1—C6—C5	119.5 (3)	H13B—C13—H13C	109.5
C1—C6—H6	120.2	C7—N1—S1	122.79 (18)
C5—C6—H6	120.2	C7—N1—H1N	114 (2)
C12—C7—C8	118.0 (2)	S1—N1—H1N	108 (2)
C12—C7—N1	121.6 (2)	O2—S1—O1	120.12 (13)
C8—C7—N1	120.3 (2)	O2—S1—N1	107.79 (13)
C9—C8—C7	121.3 (3)	O1—S1—N1	104.19 (13)
C9—C8—Cl1	118.9 (2)	O2—S1—C1	108.31 (13)
C7—C8—Cl1	119.8 (2)	O1—S1—C1	109.27 (14)
C10—C9—C8	120.1 (3)	N1—S1—C1	106.30 (12)
C10—C9—H9	120.0
C6—C1—C2—C3	−1.2 (6)	C9—C10—C11—C12	0.0 (5)
S1—C1—C2—C3	176.9 (4)	C9—C10—C11—Cl2	179.4 (3)
C1—C2—C3—C4	2.0 (8)	C10—C11—C12—C7	−1.5 (5)
C2—C3—C4—C5	−1.7 (7)	Cl2—C11—C12—C7	179.1 (2)
C2—C3—C4—C13	179.5 (4)	C8—C7—C12—C11	1.6 (4)
C3—C4—C5—C6	0.8 (7)	N1—C7—C12—C11	178.9 (3)
C13—C4—C5—C6	179.5 (4)	C12—C7—N1—S1	48.0 (3)
C2—C1—C6—C5	0.3 (6)	C8—C7—N1—S1	−134.7 (2)
S1—C1—C6—C5	−177.8 (3)	C7—N1—S1—O2	−53.8 (3)
C4—C5—C6—C1	−0.1 (7)	C7—N1—S1—O1	177.5 (2)
C12—C7—C8—C9	−0.1 (4)	C7—N1—S1—C1	62.1 (2)
N1—C7—C8—C9	−177.5 (3)	C6—C1—S1—O2	−152.1 (3)
C12—C7—C8—Cl1	179.0 (2)	C2—C1—S1—O2	29.8 (3)
N1—C7—C8—Cl1	1.6 (3)	C6—C1—S1—O1	−19.6 (3)
C7—C8—C9—C10	−1.4 (5)	C2—C1—S1—O1	162.3 (3)
Cl1—C8—C9—C10	179.5 (3)	C6—C1—S1—N1	92.3 (3)
C8—C9—C10—C11	1.4 (6)	C2—C1—S1—N1	−85.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.85 (2)	2.35 (2)	3.163 (3)	161 (3)
N1—H1N···Cl1	0.85 (2)	2.51 (3)	2.976 (2)	116 (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)	2.35 (2)	3.163 (3)	161 (3)
N1—H1N⋯Cl1	0.85 (2)	2.51 (3)	2.976 (2)	116 (3)

Symmetry code: (i) .