2,5-Dichloro-N-(2,3-dimethyl-phen-yl)benzene-sulfonamide.

In the title compound, C(14)H(13)Cl(2)NO(2)S, the dihedral angle between the aromatic rings is 62.21 (7)° and the C-S-N-C group adopts a gauche conformation [torsion angle = 60.22 (17)°]. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into C(4) chains propagating in [010]. A short inter-molecular Cl⋯O contact of 3.1115 (17) Å is seen.

Related literature

For related structures, see: Mughal et al. (2012a ▶,b ▶).

Experimental

Crystal data

C14H13Cl2NO2S

M = 330.21

Orthorhombic,

a = 13.0069 (11) Å

b = 10.0775 (9) Å

c = 22.408 (2) Å

V = 2937.2 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.58 mm−1

T = 296 K

0.30 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer

23820 measured reflections

3260 independent reflections

2377 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.090

S = 0.98

3260 reflections

186 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812035787/bt6820sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035787/bt6820Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812035787/bt6820Isup3.cml

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

C14H13Cl2NO2S	Dx = 1.494 Mg m−3
Mr = 330.21	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 1890 reflections
a = 13.0069 (11) Å	θ = 4.2–21.6°
b = 10.0775 (9) Å	µ = 0.58 mm−1
c = 22.408 (2) Å	T = 296 K
V = 2937.2 (4) Å3	Block, colourless
Z = 8	0.30 × 0.20 × 0.18 mm
F(000) = 1360

Bruker APEXII CCD diffractometer	2377 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.045
Graphite monochromator	θmax = 27.2°, θmin = 1.8°
ω scans	h = −16→15
23820 measured reflections	k = −12→12
3260 independent reflections	l = −28→28

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ2(Fo2) + (0.0396P)2 + 1.0864P] where P = (Fo2 + 2Fc2)/3
3260 reflections	(Δ/σ)max = 0.001
186 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.31 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
C1	0.36432 (15)	0.2392 (2)	0.27761 (9)	0.0380 (5)
C2	0.34175 (15)	0.1626 (2)	0.22779 (9)	0.0403 (5)
C3	0.41472 (17)	0.1589 (2)	0.18170 (10)	0.0471 (6)
C4	0.50361 (19)	0.2333 (3)	0.18622 (11)	0.0607 (7)
H1A	0.5523	0.2287	0.1559	0.073*
C5	0.52163 (19)	0.3142 (3)	0.23476 (12)	0.0648 (7)
H13	0.5802	0.3670	0.2362	0.078*
C6	0.45235 (17)	0.3159 (2)	0.28092 (11)	0.0510 (6)
H14	0.4645	0.3685	0.3143	0.061*
C7	0.24248 (18)	0.0871 (3)	0.22183 (11)	0.0593 (7)
H11A	0.2014	0.1006	0.2569	0.089*
H11B	0.2570	−0.0058	0.2174	0.089*
H11C	0.2057	0.1183	0.1874	0.089*
C8	0.3960 (2)	0.0772 (3)	0.12657 (11)	0.0689 (8)
H12A	0.4552	0.0817	0.1011	0.103*
H12B	0.3371	0.1111	0.1057	0.103*
H12C	0.3838	−0.0134	0.1377	0.103*
C9	0.42663 (14)	0.14693 (19)	0.41375 (8)	0.0334 (4)
C10	0.45813 (15)	0.2588 (2)	0.44538 (9)	0.0376 (5)
C11	0.55332 (16)	0.2609 (2)	0.47257 (10)	0.0469 (5)
H7	0.5742	0.3358	0.4936	0.056*
C12	0.61758 (16)	0.1526 (2)	0.46883 (10)	0.0490 (6)
H8	0.6814	0.1538	0.4875	0.059*
C13	0.58658 (16)	0.0429 (2)	0.43732 (9)	0.0416 (5)
C14	0.49226 (15)	0.0390 (2)	0.40944 (9)	0.0389 (5)
H10	0.4727	−0.0356	0.3878	0.047*
Cl1	0.38122 (4)	0.39770 (5)	0.45093 (3)	0.04880 (16)
Cl2	0.66673 (5)	−0.09408 (7)	0.43314 (3)	0.0630 (2)
S1	0.30265 (4)	0.13320 (5)	0.38004 (2)	0.03558 (14)
N1	0.29345 (12)	0.24200 (17)	0.32771 (8)	0.0376 (4)
H1	0.2777 (16)	0.322 (2)	0.3392 (10)	0.045*
O1	0.30173 (10)	0.00454 (14)	0.35289 (7)	0.0443 (4)
O2	0.22658 (11)	0.16635 (16)	0.42321 (7)	0.0487 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0366 (10)	0.0394 (12)	0.0381 (11)	0.0035 (9)	−0.0028 (8)	0.0021 (10)
C2	0.0406 (11)	0.0416 (12)	0.0386 (12)	0.0063 (10)	−0.0032 (9)	−0.0006 (10)
C3	0.0519 (13)	0.0519 (14)	0.0375 (12)	0.0134 (11)	0.0019 (10)	0.0036 (11)
C4	0.0500 (13)	0.0814 (19)	0.0506 (15)	0.0037 (13)	0.0089 (11)	0.0181 (14)
C5	0.0498 (14)	0.0821 (19)	0.0627 (17)	−0.0222 (14)	−0.0005 (12)	0.0166 (15)
C6	0.0541 (13)	0.0544 (14)	0.0446 (13)	−0.0158 (12)	−0.0040 (11)	0.0014 (12)
C7	0.0507 (13)	0.0732 (17)	0.0540 (14)	−0.0088 (13)	−0.0089 (11)	−0.0155 (14)
C8	0.0825 (19)	0.078 (2)	0.0458 (14)	0.0175 (15)	0.0057 (13)	−0.0104 (14)
C9	0.0351 (10)	0.0356 (11)	0.0296 (10)	−0.0050 (9)	0.0024 (8)	−0.0019 (9)
C10	0.0390 (10)	0.0374 (11)	0.0365 (11)	−0.0029 (9)	−0.0006 (8)	−0.0027 (9)
C11	0.0462 (12)	0.0483 (13)	0.0461 (13)	−0.0077 (11)	−0.0079 (10)	−0.0096 (11)
C12	0.0382 (11)	0.0592 (15)	0.0497 (14)	−0.0038 (11)	−0.0091 (10)	−0.0002 (12)
C13	0.0401 (11)	0.0439 (12)	0.0407 (12)	0.0038 (10)	0.0028 (9)	0.0077 (10)
C14	0.0412 (11)	0.0373 (11)	0.0384 (11)	−0.0036 (9)	0.0018 (9)	−0.0021 (9)
Cl1	0.0479 (3)	0.0399 (3)	0.0586 (4)	0.0005 (2)	−0.0035 (2)	−0.0150 (3)
Cl2	0.0558 (4)	0.0571 (4)	0.0760 (4)	0.0165 (3)	−0.0020 (3)	0.0082 (3)
S1	0.0320 (2)	0.0373 (3)	0.0374 (3)	−0.0063 (2)	0.0019 (2)	−0.0072 (2)
N1	0.0382 (9)	0.0360 (9)	0.0386 (9)	0.0041 (8)	0.0001 (7)	−0.0077 (8)
O1	0.0438 (8)	0.0374 (8)	0.0515 (9)	−0.0084 (7)	−0.0015 (7)	−0.0112 (7)
O2	0.0393 (8)	0.0595 (10)	0.0473 (9)	−0.0077 (7)	0.0115 (7)	−0.0117 (8)

C1—C6	1.384 (3)	C8—H12C	0.9600
C1—C2	1.388 (3)	C9—C14	1.386 (3)
C1—N1	1.453 (3)	C9—C10	1.394 (3)
C2—C3	1.403 (3)	C9—S1	1.786 (2)
C2—C7	1.505 (3)	C10—C11	1.380 (3)
C3—C4	1.381 (3)	C10—Cl1	1.725 (2)
C3—C8	1.505 (3)	C11—C12	1.377 (3)
C4—C5	1.379 (4)	C11—H7	0.9300
C4—H1A	0.9300	C12—C13	1.372 (3)
C5—C6	1.372 (3)	C12—H8	0.9300
C5—H13	0.9300	C13—C14	1.377 (3)
C6—H14	0.9300	C13—Cl2	1.732 (2)
C7—H11A	0.9600	C14—H10	0.9300
C7—H11B	0.9600	S1—O2	1.4235 (14)
C7—H11C	0.9600	S1—O1	1.4323 (14)
C8—H12A	0.9600	S1—N1	1.6098 (18)
C8—H12B	0.9600	N1—H1	0.87 (2)
C6—C1—C2	121.9 (2)	H12B—C8—H12C	109.5
C6—C1—N1	118.21 (19)	C14—C9—C10	119.30 (18)
C2—C1—N1	119.86 (18)	C14—C9—S1	117.77 (15)
C1—C2—C3	117.6 (2)	C10—C9—S1	122.90 (15)
C1—C2—C7	122.27 (19)	C11—C10—C9	120.01 (19)
C3—C2—C7	120.1 (2)	C11—C10—Cl1	118.46 (16)
C4—C3—C2	119.9 (2)	C9—C10—Cl1	121.52 (15)
C4—C3—C8	119.5 (2)	C12—C11—C10	120.4 (2)
C2—C3—C8	120.6 (2)	C12—C11—H7	119.8
C5—C4—C3	121.4 (2)	C10—C11—H7	119.8
C5—C4—H1A	119.3	C13—C12—C11	119.42 (19)
C3—C4—H1A	119.3	C13—C12—H8	120.3
C6—C5—C4	119.4 (2)	C11—C12—H8	120.3
C6—C5—H13	120.3	C12—C13—C14	121.2 (2)
C4—C5—H13	120.3	C12—C13—Cl2	119.53 (17)
C5—C6—C1	119.7 (2)	C14—C13—Cl2	119.27 (18)
C5—C6—H14	120.1	C13—C14—C9	119.7 (2)
C1—C6—H14	120.1	C13—C14—H10	120.2
C2—C7—H11A	109.5	C9—C14—H10	120.2
C2—C7—H11B	109.5	O2—S1—O1	119.69 (9)
H11A—C7—H11B	109.5	O2—S1—N1	106.47 (9)
C2—C7—H11C	109.5	O1—S1—N1	107.85 (9)
H11A—C7—H11C	109.5	O2—S1—C9	108.78 (9)
H11B—C7—H11C	109.5	O1—S1—C9	104.91 (9)
C3—C8—H12A	109.5	N1—S1—C9	108.81 (9)
C3—C8—H12B	109.5	C1—N1—S1	120.16 (14)
H12A—C8—H12B	109.5	C1—N1—H1	113.4 (15)
C3—C8—H12C	109.5	S1—N1—H1	115.5 (15)
H12A—C8—H12C	109.5
C6—C1—C2—C3	3.8 (3)	Cl1—C10—C11—C12	−179.43 (18)
N1—C1—C2—C3	−177.39 (18)	C10—C11—C12—C13	0.6 (3)
C6—C1—C2—C7	−175.2 (2)	C11—C12—C13—C14	−0.1 (3)
N1—C1—C2—C7	3.6 (3)	C11—C12—C13—Cl2	−179.36 (17)
C1—C2—C3—C4	−2.0 (3)	C12—C13—C14—C9	−0.8 (3)
C7—C2—C3—C4	177.0 (2)	Cl2—C13—C14—C9	178.45 (15)
C1—C2—C3—C8	179.5 (2)	C10—C9—C14—C13	1.2 (3)
C7—C2—C3—C8	−1.5 (3)	S1—C9—C14—C13	−176.79 (16)
C2—C3—C4—C5	−1.5 (4)	C14—C9—S1—O2	127.48 (16)
C8—C3—C4—C5	177.1 (2)	C10—C9—S1—O2	−50.46 (19)
C3—C4—C5—C6	3.3 (4)	C14—C9—S1—O1	−1.71 (18)
C4—C5—C6—C1	−1.5 (4)	C10—C9—S1—O1	−179.65 (16)
C2—C1—C6—C5	−2.0 (3)	C14—C9—S1—N1	−116.91 (16)
N1—C1—C6—C5	179.1 (2)	C10—C9—S1—N1	65.14 (18)
C14—C9—C10—C11	−0.7 (3)	C6—C1—N1—S1	−93.2 (2)
S1—C9—C10—C11	177.17 (16)	C2—C1—N1—S1	87.9 (2)
C14—C9—C10—Cl1	178.49 (15)	O2—S1—N1—C1	177.30 (15)
S1—C9—C10—Cl1	−3.6 (2)	O1—S1—N1—C1	−53.06 (17)
C9—C10—C11—C12	−0.2 (3)	C9—S1—N1—C1	60.22 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.87 (2)	2.14 (2)	2.975 (2)	162.9 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.87 (2)	2.14 (2)	2.975 (2)	162.9 (19)

Symmetry code: (i) .