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

In the title compound, C(14)H(13)Cl(2)NO(2)S, the dihedral angle between the two aromatic rings is 70.4 (1)°. The mol-ecular conformation is stabilized by an intra-molecular N-H⋯Cl hydrogen bond.

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

Monoclinic,

a = 9.198 (1) Å

b = 9.933 (1) Å

c = 16.099 (2) Å

β = 99.100 (1)°

V = 1452.4 (3) Å3

Z = 4

Cu Kα radiation

μ = 5.37 mm−1

T = 299 K

0.53 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

3394 measured reflections

2581 independent reflections

2367 reflections with I > 2σ(I)

R int = 0.041

3 standard reflections every 120 min intensity decay: 1.0%

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.111

S = 1.13

2581 reflections

186 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.66 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/S1600536810044338/bt5400sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810044338/bt5400Isup2.hkl

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

C14H13Cl2NO2S	F(000) = 680
Mr = 330.21	Dx = 1.510 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 9.198 (1) Å	θ = 4.9–22.5°
b = 9.933 (1) Å	µ = 5.37 mm−1
c = 16.099 (2) Å	T = 299 K
β = 99.100 (1)°	Prism, colorless
V = 1452.4 (3) Å3	0.53 × 0.20 × 0.20 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.041
Radiation source: fine-focus sealed tube	θmax = 66.9°, θmin = 4.9°
graphite	h = −10→10
ω/2θ scans	k = −11→0
3394 measured reflections	l = −19→4
2581 independent reflections	3 standard reflections every 120 min
2367 reflections with I > 2σ(I)	intensity decay: 1.0%

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ2(Fo2) + (0.0691P)2 + 0.3328P] where P = (Fo2 + 2Fc2)/3
2581 reflections	(Δ/σ)max < 0.001
186 parameters	Δρmax = 0.26 e Å−3
1 restraint	Δρmin = −0.66 e Å−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
Cl1	0.25244 (6)	−0.10202 (6)	0.09534 (4)	0.05416 (19)
Cl2	−0.08838 (6)	−0.14100 (6)	0.06647 (4)	0.0576 (2)
S1	0.45032 (5)	0.26140 (5)	0.21630 (3)	0.04180 (18)
O1	0.60015 (16)	0.22571 (19)	0.21346 (11)	0.0561 (4)
O2	0.41640 (18)	0.33596 (18)	0.28705 (10)	0.0545 (4)
N1	0.36407 (18)	0.11597 (18)	0.21294 (12)	0.0432 (4)
H1N	0.409 (3)	0.052 (2)	0.1949 (16)	0.052*
C1	0.3736 (2)	0.3504 (2)	0.12509 (13)	0.0385 (4)
C2	0.3976 (2)	0.3127 (2)	0.04461 (13)	0.0418 (5)
C3	0.3316 (3)	0.3909 (2)	−0.02241 (14)	0.0492 (5)
H3	0.3482	0.3688	−0.0763	0.059*
C4	0.2427 (3)	0.4999 (2)	−0.01297 (16)	0.0535 (6)
C5	0.2205 (3)	0.5337 (2)	0.06777 (17)	0.0592 (6)
H5	0.1606	0.6065	0.0757	0.071*
C6	0.2859 (3)	0.4606 (2)	0.13590 (15)	0.0509 (5)
H6	0.2713	0.4852	0.1897	0.061*
C7	0.2086 (2)	0.10239 (19)	0.19856 (12)	0.0366 (4)
C8	0.1436 (2)	0.00162 (19)	0.14533 (12)	0.0370 (4)
C9	−0.0078 (2)	−0.0153 (2)	0.13289 (13)	0.0409 (5)
C10	−0.0959 (2)	0.0673 (2)	0.17213 (14)	0.0482 (5)
H10	−0.1975	0.0555	0.1634	0.058*
C11	−0.0319 (2)	0.1676 (3)	0.22442 (15)	0.0513 (5)
H11	−0.0910	0.2245	0.2506	0.062*
C12	0.1197 (2)	0.1853 (2)	0.23870 (14)	0.0467 (5)
H12	0.1617	0.2524	0.2751	0.056*
C13	0.4877 (3)	0.1928 (3)	0.02611 (16)	0.0583 (6)
H13A	0.5892	0.2075	0.0494	0.070*
H13B	0.4789	0.1809	−0.0337	0.070*
H13C	0.4526	0.1136	0.0508	0.070*
C14	0.1715 (4)	0.5790 (3)	−0.0878 (2)	0.0778 (9)
H14A	0.2434	0.5993	−0.1232	0.093*
H14B	0.1324	0.6613	−0.0692	0.093*
H14C	0.0933	0.5270	−0.1189	0.093*

	U11	U22	U33	U12	U13	U23
Cl1	0.0441 (3)	0.0501 (3)	0.0692 (4)	0.0080 (2)	0.0118 (3)	−0.0127 (2)
Cl2	0.0507 (3)	0.0612 (4)	0.0571 (3)	−0.0150 (2)	−0.0028 (2)	0.0009 (3)
S1	0.0302 (3)	0.0512 (3)	0.0432 (3)	−0.00367 (19)	0.00317 (19)	−0.0066 (2)
O1	0.0278 (7)	0.0756 (11)	0.0636 (10)	−0.0026 (7)	0.0036 (7)	−0.0020 (8)
O2	0.0526 (9)	0.0673 (10)	0.0427 (8)	−0.0068 (8)	0.0050 (7)	−0.0160 (7)
N1	0.0296 (8)	0.0444 (10)	0.0554 (10)	0.0026 (7)	0.0059 (7)	−0.0006 (8)
C1	0.0325 (9)	0.0398 (10)	0.0436 (10)	−0.0056 (8)	0.0072 (8)	−0.0065 (8)
C2	0.0340 (10)	0.0454 (11)	0.0474 (11)	−0.0083 (8)	0.0105 (8)	−0.0089 (9)
C3	0.0472 (12)	0.0552 (13)	0.0448 (11)	−0.0144 (10)	0.0067 (9)	−0.0055 (9)
C4	0.0542 (13)	0.0437 (12)	0.0602 (14)	−0.0143 (10)	0.0014 (11)	0.0032 (10)
C5	0.0653 (15)	0.0387 (11)	0.0729 (16)	0.0055 (11)	0.0092 (12)	−0.0036 (11)
C6	0.0575 (13)	0.0440 (11)	0.0527 (13)	0.0017 (10)	0.0136 (10)	−0.0096 (10)
C7	0.0292 (9)	0.0394 (10)	0.0415 (10)	0.0019 (7)	0.0070 (8)	0.0068 (8)
C8	0.0335 (10)	0.0376 (10)	0.0408 (10)	0.0050 (8)	0.0087 (8)	0.0084 (8)
C9	0.0359 (10)	0.0441 (10)	0.0419 (10)	−0.0037 (8)	0.0037 (8)	0.0107 (8)
C10	0.0295 (9)	0.0602 (13)	0.0564 (12)	0.0035 (9)	0.0110 (9)	0.0133 (10)
C11	0.0395 (11)	0.0573 (13)	0.0607 (13)	0.0094 (10)	0.0185 (10)	0.0021 (11)
C12	0.0402 (11)	0.0494 (12)	0.0528 (12)	0.0012 (9)	0.0143 (9)	−0.0042 (10)
C13	0.0533 (13)	0.0682 (15)	0.0563 (13)	0.0088 (12)	0.0179 (11)	−0.0144 (12)
C14	0.080 (2)	0.0654 (17)	0.082 (2)	−0.0069 (15)	−0.0054 (16)	0.0205 (15)

Cl1—C8	1.7221 (19)	C5—H5	0.9300
Cl2—C9	1.733 (2)	C6—H6	0.9300
S1—O1	1.4307 (16)	C7—C12	1.389 (3)
S1—O2	1.4338 (16)	C7—C8	1.390 (3)
S1—N1	1.6448 (18)	C8—C9	1.385 (3)
S1—C1	1.763 (2)	C9—C10	1.375 (3)
N1—C7	1.419 (2)	C10—C11	1.375 (3)
N1—H1N	0.839 (17)	C10—H10	0.9300
C1—C6	1.387 (3)	C11—C12	1.387 (3)
C1—C2	1.399 (3)	C11—H11	0.9300
C2—C3	1.389 (3)	C12—H12	0.9300
C2—C13	1.507 (3)	C13—H13A	0.9600
C3—C4	1.379 (4)	C13—H13B	0.9600
C3—H3	0.9300	C13—H13C	0.9600
C4—C5	1.388 (4)	C14—H14A	0.9600
C4—C14	1.499 (4)	C14—H14B	0.9600
C5—C6	1.372 (4)	C14—H14C	0.9600
O1—S1—O2	119.02 (10)	C8—C7—N1	119.57 (17)
O1—S1—N1	104.09 (10)	C9—C8—C7	120.06 (18)
O2—S1—N1	108.37 (10)	C9—C8—Cl1	120.38 (16)
O1—S1—C1	111.01 (10)	C7—C8—Cl1	119.56 (15)
O2—S1—C1	107.10 (10)	C10—C9—C8	120.9 (2)
N1—S1—C1	106.58 (9)	C10—C9—Cl2	119.20 (16)
C7—N1—S1	123.88 (14)	C8—C9—Cl2	119.90 (17)
C7—N1—H1N	114.4 (18)	C9—C10—C11	119.14 (19)
S1—N1—H1N	114.7 (18)	C9—C10—H10	120.4
C6—C1—C2	120.5 (2)	C11—C10—H10	120.4
C6—C1—S1	117.09 (16)	C10—C11—C12	121.0 (2)
C2—C1—S1	122.40 (16)	C10—C11—H11	119.5
C3—C2—C1	117.1 (2)	C12—C11—H11	119.5
C3—C2—C13	118.4 (2)	C11—C12—C7	119.9 (2)
C1—C2—C13	124.5 (2)	C11—C12—H12	120.1
C4—C3—C2	123.2 (2)	C7—C12—H12	120.1
C4—C3—H3	118.4	C2—C13—H13A	109.5
C2—C3—H3	118.4	C2—C13—H13B	109.5
C3—C4—C5	118.1 (2)	H13A—C13—H13B	109.5
C3—C4—C14	120.9 (3)	C2—C13—H13C	109.5
C5—C4—C14	121.0 (3)	H13A—C13—H13C	109.5
C6—C5—C4	120.6 (2)	H13B—C13—H13C	109.5
C6—C5—H5	119.7	C4—C14—H14A	109.5
C4—C5—H5	119.7	C4—C14—H14B	109.5
C5—C6—C1	120.5 (2)	H14A—C14—H14B	109.5
C5—C6—H6	119.8	C4—C14—H14C	109.5
C1—C6—H6	119.8	H14A—C14—H14C	109.5
C12—C7—C8	119.07 (18)	H14B—C14—H14C	109.5
C12—C7—N1	121.33 (19)
O1—S1—N1—C7	−167.74 (17)	C4—C5—C6—C1	−1.0 (4)
O2—S1—N1—C7	64.64 (19)	C2—C1—C6—C5	0.5 (3)
C1—S1—N1—C7	−50.33 (19)	S1—C1—C6—C5	−179.00 (19)
O1—S1—C1—C6	−138.08 (17)	S1—N1—C7—C12	−44.1 (3)
O2—S1—C1—C6	−6.64 (19)	S1—N1—C7—C8	137.91 (17)
N1—S1—C1—C6	109.19 (17)	C12—C7—C8—C9	0.0 (3)
O1—S1—C1—C2	42.39 (19)	N1—C7—C8—C9	177.98 (17)
O2—S1—C1—C2	173.83 (16)	C12—C7—C8—Cl1	−179.87 (16)
N1—S1—C1—C2	−70.35 (18)	N1—C7—C8—Cl1	−1.9 (2)
C6—C1—C2—C3	0.7 (3)	C7—C8—C9—C10	0.5 (3)
S1—C1—C2—C3	−179.79 (15)	Cl1—C8—C9—C10	−179.67 (16)
C6—C1—C2—C13	−178.4 (2)	C7—C8—C9—Cl2	179.99 (14)
S1—C1—C2—C13	1.1 (3)	Cl1—C8—C9—Cl2	−0.2 (2)
C1—C2—C3—C4	−1.5 (3)	C8—C9—C10—C11	−0.1 (3)
C13—C2—C3—C4	177.6 (2)	Cl2—C9—C10—C11	−179.59 (17)
C2—C3—C4—C5	1.0 (3)	C9—C10—C11—C12	−0.8 (3)
C2—C3—C4—C14	−178.6 (2)	C10—C11—C12—C7	1.2 (3)
C3—C4—C5—C6	0.3 (4)	C8—C7—C12—C11	−0.8 (3)
C14—C4—C5—C6	179.9 (3)	N1—C7—C12—C11	−178.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···Cl1	0.84 (2)	2.50 (2)	2.9517 (19)	115 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯Cl1	0.84 (2)	2.50 (2)	2.9517 (19)	115 (2)