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

In the title compound, C(14)H(13)Cl(2)NO(2)S, the mol-ecule is bent at the S atom with an C-SO(2)-NH-C torsion angle of -69.9 (2)°. The dihedral angle between the sulfonyl and aniline benzene rings is 44.0 (1)°. The crystal structure features inversion dimers linked by pairs of N-H⋯O hydrogen bonds. An intra-molecular N-H⋯Cl hydrogen bond is also observed.

Related literature

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

Experimental

Crystal data

C14H13Cl2NO2S

M = 330.21

Triclinic,

a = 8.2407 (9) Å

b = 8.3418 (9) Å

c = 10.849 (1) Å

α = 84.59 (1)°

β = 89.06 (1)°

γ = 85.07 (1)°

V = 739.69 (13) Å3

Z = 2

Cu Kα radiation

μ = 5.27 mm−1

T = 293 K

0.45 × 0.40 × 0.13 mm

Data collection

Ennraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.200, T max = 0.547

5173 measured reflections

2629 independent reflections

2496 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)] = 0.056

wR(F 2) = 0.159

S = 1.05

2629 reflections

187 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.80 e Å−3

Data collection: CAD-4-PC (Enraf–n class="Chemical">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/S1600536810045563/bq2251sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045563/bq2251Isup2.hkl

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

C14H13Cl2NO2S	Z = 2
Mr = 330.21	F(000) = 340
Triclinic, P1	Dx = 1.483 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54180 Å
a = 8.2407 (9) Å	Cell parameters from 25 reflections
b = 8.3418 (9) Å	θ = 6.7–18.3°
c = 10.849 (1) Å	µ = 5.27 mm−1
α = 84.59 (1)°	T = 293 K
β = 89.06 (1)°	Plate, colorless
γ = 85.07 (1)°	0.45 × 0.40 × 0.13 mm
V = 739.69 (13) Å3

Ennraf–Nonius CAD-4 diffractometer	2496 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
graphite	θmax = 66.9°, θmin = 4.1°
ω/2θ scans	h = −9→9
Absorption correction: ψ scan (North et al., 1968)	k = −9→9
Tmin = 0.200, Tmax = 0.547	l = −12→12
5173 measured reflections	3 standard reflections every 120 min
2629 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)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.159	w = 1/[σ2(Fo2) + (0.1122P)2 + 0.3056P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.003
2629 reflections	Δρmax = 0.41 e Å−3
187 parameters	Δρmin = −0.80 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: 0.0131 (18)

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	0.0771 (3)	0.4275 (3)	0.2785 (2)	0.0417 (5)
C2	0.1504 (3)	0.3433 (3)	0.3839 (2)	0.0494 (6)
C3	0.0454 (4)	0.2704 (4)	0.4696 (3)	0.0593 (7)
H3	0.0903	0.2133	0.5405	0.071*
C4	−0.1211 (4)	0.2779 (4)	0.4556 (3)	0.0586 (7)
C5	−0.1883 (4)	0.3659 (4)	0.3526 (3)	0.0571 (7)
H5	−0.3007	0.3764	0.3428	0.069*
C6	−0.0905 (3)	0.4382 (3)	0.2642 (2)	0.0497 (6)
H6	−0.1372	0.4952	0.1939	0.060*
C7	0.3576 (3)	0.2472 (3)	0.0982 (2)	0.0385 (5)
C8	0.3155 (3)	0.0907 (3)	0.1315 (2)	0.0394 (5)
C9	0.4329 (3)	−0.0337 (3)	0.1657 (2)	0.0440 (6)
H9	0.4039	−0.1381	0.1872	0.053*
C10	0.5934 (3)	0.0004 (3)	0.1671 (2)	0.0448 (6)
C11	0.6398 (3)	0.1535 (3)	0.1328 (2)	0.0496 (6)
H11	0.7490	0.1741	0.1331	0.060*
C12	0.5214 (3)	0.2753 (3)	0.0980 (2)	0.0459 (6)
H12	0.5516	0.3785	0.0739	0.055*
C13	0.3296 (4)	0.3251 (5)	0.4112 (3)	0.0705 (9)
H13A	0.3685	0.4300	0.4134	0.085*
H13B	0.3869	0.2698	0.3477	0.085*
H13C	0.3478	0.2639	0.4899	0.085*
C14	−0.2268 (5)	0.1923 (5)	0.5518 (4)	0.0833 (11)
H14A	−0.1703	0.1745	0.6292	0.100*
H14B	−0.2503	0.0904	0.5250	0.100*
H14C	−0.3268	0.2579	0.5621	0.100*
N1	0.2394 (3)	0.3750 (2)	0.06051 (18)	0.0425 (5)
H1N	0.156 (3)	0.347 (4)	0.026 (3)	0.051*
O1	0.3348 (2)	0.5697 (2)	0.1953 (2)	0.0564 (5)
O2	0.0776 (3)	0.6299 (2)	0.08078 (18)	0.0559 (5)
Cl1	0.11490 (8)	0.04794 (8)	0.12875 (7)	0.0581 (3)
Cl2	0.74198 (9)	−0.15459 (9)	0.20963 (7)	0.0672 (3)
S1	0.18758 (7)	0.51721 (7)	0.15244 (5)	0.0428 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0409 (12)	0.0415 (13)	0.0434 (12)	−0.0039 (9)	0.0029 (10)	−0.0073 (10)
C2	0.0487 (15)	0.0545 (16)	0.0446 (13)	0.0003 (11)	−0.0017 (11)	−0.0077 (11)
C3	0.0670 (18)	0.0663 (18)	0.0424 (13)	0.0009 (14)	−0.0003 (12)	0.0003 (12)
C4	0.0614 (17)	0.0637 (18)	0.0516 (15)	−0.0101 (14)	0.0112 (13)	−0.0078 (13)
C5	0.0440 (14)	0.0716 (19)	0.0575 (15)	−0.0091 (13)	0.0056 (12)	−0.0119 (13)
C6	0.0450 (14)	0.0559 (15)	0.0475 (13)	−0.0012 (11)	−0.0019 (10)	−0.0034 (11)
C7	0.0397 (12)	0.0382 (12)	0.0374 (11)	−0.0034 (9)	0.0025 (9)	−0.0027 (9)
C8	0.0398 (12)	0.0406 (13)	0.0384 (11)	−0.0086 (9)	0.0006 (9)	−0.0029 (9)
C9	0.0503 (14)	0.0380 (12)	0.0429 (12)	−0.0041 (10)	−0.0009 (10)	0.0008 (9)
C10	0.0440 (13)	0.0455 (13)	0.0439 (12)	0.0053 (10)	−0.0032 (10)	−0.0071 (10)
C11	0.0381 (13)	0.0524 (15)	0.0599 (15)	−0.0058 (11)	0.0026 (11)	−0.0122 (12)
C12	0.0413 (13)	0.0404 (13)	0.0568 (14)	−0.0082 (10)	0.0079 (10)	−0.0058 (10)
C13	0.0512 (17)	0.097 (3)	0.0608 (17)	0.0054 (16)	−0.0101 (13)	−0.0045 (16)
C14	0.084 (3)	0.092 (3)	0.073 (2)	−0.018 (2)	0.0244 (19)	0.0047 (19)
N1	0.0435 (11)	0.0382 (11)	0.0450 (11)	−0.0008 (8)	0.0010 (8)	−0.0015 (8)
O1	0.0508 (11)	0.0462 (11)	0.0749 (12)	−0.0120 (8)	0.0031 (9)	−0.0134 (9)
O2	0.0590 (12)	0.0403 (10)	0.0646 (11)	0.0061 (8)	0.0026 (9)	0.0059 (8)
Cl1	0.0405 (4)	0.0519 (4)	0.0825 (5)	−0.0131 (3)	−0.0042 (3)	−0.0001 (3)
Cl2	0.0586 (5)	0.0630 (5)	0.0758 (5)	0.0180 (3)	−0.0144 (4)	−0.0036 (4)
S1	0.0434 (4)	0.0333 (4)	0.0512 (4)	−0.0023 (2)	0.0033 (3)	−0.0024 (3)

C1—C6	1.387 (4)	C9—C10	1.378 (4)
C1—C2	1.402 (4)	C9—H9	0.9300
C1—S1	1.773 (2)	C10—C11	1.381 (4)
C2—C3	1.393 (4)	C10—Cl2	1.737 (2)
C2—C13	1.502 (4)	C11—C12	1.377 (4)
C3—C4	1.378 (5)	C11—H11	0.9300
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.374 (4)	C13—H13A	0.9600
C4—C14	1.515 (4)	C13—H13B	0.9600
C5—C6	1.372 (4)	C13—H13C	0.9600
C5—H5	0.9300	C14—H14A	0.9600
C6—H6	0.9300	C14—H14B	0.9600
C7—C12	1.389 (3)	C14—H14C	0.9600
C7—C8	1.393 (3)	N1—S1	1.645 (2)
C7—N1	1.416 (3)	N1—H1N	0.853 (18)
C8—C9	1.384 (3)	O1—S1	1.424 (2)
C8—Cl1	1.722 (2)	O2—S1	1.4311 (19)
C6—C1—C2	120.8 (2)	C11—C10—Cl2	119.1 (2)
C6—C1—S1	115.43 (19)	C12—C11—C10	118.7 (2)
C2—C1—S1	123.7 (2)	C12—C11—H11	120.6
C3—C2—C1	115.9 (3)	C10—C11—H11	120.6
C3—C2—C13	118.1 (3)	C11—C12—C7	121.4 (2)
C1—C2—C13	125.9 (3)	C11—C12—H12	119.3
C4—C3—C2	123.9 (3)	C7—C12—H12	119.3
C4—C3—H3	118.1	C2—C13—H13A	109.5
C2—C3—H3	118.1	C2—C13—H13B	109.5
C5—C4—C3	118.2 (3)	H13A—C13—H13B	109.5
C5—C4—C14	121.1 (3)	C2—C13—H13C	109.5
C3—C4—C14	120.7 (3)	H13A—C13—H13C	109.5
C6—C5—C4	120.4 (3)	H13B—C13—H13C	109.5
C6—C5—H5	119.8	C4—C14—H14A	109.5
C4—C5—H5	119.8	C4—C14—H14B	109.5
C5—C6—C1	120.8 (3)	H14A—C14—H14B	109.5
C5—C6—H6	119.6	C4—C14—H14C	109.5
C1—C6—H6	119.6	H14A—C14—H14C	109.5
C12—C7—C8	118.3 (2)	H14B—C14—H14C	109.5
C12—C7—N1	119.8 (2)	C7—N1—S1	120.33 (16)
C8—C7—N1	121.9 (2)	C7—N1—H1N	115 (2)
C9—C8—C7	121.2 (2)	S1—N1—H1N	110 (2)
C9—C8—Cl1	118.61 (18)	O1—S1—O2	119.34 (13)
C7—C8—Cl1	120.21 (19)	O1—S1—N1	106.94 (12)
C10—C9—C8	118.6 (2)	O2—S1—N1	104.56 (11)
C10—C9—H9	120.7	O1—S1—C1	110.04 (12)
C8—C9—H9	120.7	O2—S1—C1	108.11 (12)
C9—C10—C11	121.8 (2)	N1—S1—C1	107.11 (11)
C9—C10—Cl2	119.1 (2)
C6—C1—C2—C3	1.3 (4)	C8—C9—C10—C11	−1.5 (4)
S1—C1—C2—C3	−175.4 (2)	C8—C9—C10—Cl2	−179.91 (18)
C6—C1—C2—C13	−179.0 (3)	C9—C10—C11—C12	1.0 (4)
S1—C1—C2—C13	4.4 (4)	Cl2—C10—C11—C12	179.3 (2)
C1—C2—C3—C4	−0.2 (4)	C10—C11—C12—C7	0.7 (4)
C13—C2—C3—C4	−180.0 (3)	C8—C7—C12—C11	−1.7 (4)
C2—C3—C4—C5	−1.8 (5)	N1—C7—C12—C11	−179.3 (2)
C2—C3—C4—C14	178.7 (3)	C12—C7—N1—S1	−74.9 (3)
C3—C4—C5—C6	2.6 (5)	C8—C7—N1—S1	107.6 (2)
C14—C4—C5—C6	−177.8 (3)	C7—N1—S1—O1	48.1 (2)
C4—C5—C6—C1	−1.6 (4)	C7—N1—S1—O2	175.56 (18)
C2—C1—C6—C5	−0.4 (4)	C7—N1—S1—C1	−69.8 (2)
S1—C1—C6—C5	176.5 (2)	C6—C1—S1—O1	151.8 (2)
C12—C7—C8—C9	1.1 (4)	C2—C1—S1—O1	−31.4 (3)
N1—C7—C8—C9	178.6 (2)	C6—C1—S1—O2	19.9 (2)
C12—C7—C8—Cl1	−178.02 (18)	C2—C1—S1—O2	−163.3 (2)
N1—C7—C8—Cl1	−0.5 (3)	C6—C1—S1—N1	−92.3 (2)
C7—C8—C9—C10	0.5 (4)	C2—C1—S1—N1	84.5 (2)
Cl1—C8—C9—C10	179.62 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.85 (2)	2.24 (2)	3.056 (3)	159 (3)
N1—H1N···Cl1	0.85 (2)	2.68 (3)	3.020 (2)	105 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.85 (2)	2.24 (2)	3.056 (3)	159 (3)
N1—H1N⋯Cl1	0.85 (2)	2.68 (3)	3.020 (2)	105 (2)

Symmetry code: (i) .