2,4-Dichloro-N-(3,5-dimethyl-phen-yl)benzene-sulfonamide.

In the crystal of the title compound, C(14)H(13)Cl(2)NO(2)S, the N-H bond in the C-SO(2)-NH-C segment is syn to one of the meta-methyl groups in the aniline benzene ring and anti to the other. Further, the conformation of the N-C bond in the C-SO(2)-NH-C segment is gauche with respect to the S=O bonds. The C-SO(2)-NH-C torsion angle is 54.9 (2)°. The sulfonyl and aniline benzene rings are tilted relative to each other by 82.8 (1)°. The crystal structure features inversion-related dimers linked by pairs of N-H⋯O hydrogen bonds. There are also weak C-H⋯O hydrogen bonds between these dimers.

Related literature

For the preparation of the title compound, see: Savitha & Gowda (2006 ▶). For hydrogen-bonding modes of sulfonamides, see: Adsmond & Grant (2001 ▶). For our studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Gowda et al. (2003 ▶), on N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007 ▶) and on N-(ar­yl)-aryl­sulfonamides, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶); Gowda & Kumar (2003 ▶); Rodrigues et al. (2011 ▶).

Experimental

Crystal data

C14H13Cl2NO2S

M = 330.21

Monoclinic,

a = 23.067 (2) Å

b = 8.0794 (5) Å

c = 16.470 (1) Å

β = 101.575 (7)°

V = 3007.0 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.57 mm−1

T = 293 K

0.50 × 0.46 × 0.42 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD Detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.764, T max = 0.796

10045 measured reflections

3067 independent reflections

2555 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.124

S = 1.09

3067 reflections

186 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.73 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; 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 datablock(s) I, global. DOI: 10.1107/S1600536811040189/bq2307sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811040189/bq2307Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811040189/bq2307Isup3.cml

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

C14H13Cl2NO2S	F(000) = 1360
Mr = 330.21	Dx = 1.459 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3755 reflections
a = 23.067 (2) Å	θ = 2.7–28.0°
b = 8.0794 (5) Å	µ = 0.57 mm−1
c = 16.470 (1) Å	T = 293 K
β = 101.575 (7)°	Prism, light pink
V = 3007.0 (4) Å3	0.50 × 0.46 × 0.42 mm
Z = 8

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD Detector	3067 independent reflections
Radiation source: fine-focus sealed tube	2555 reflections with I > 2σ(I)
graphite	Rint = 0.018
Rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 2.7°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −26→28
Tmin = 0.764, Tmax = 0.796	k = −10→10
10045 measured reflections	l = −20→10

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.080P)2 + 1.2587P] where P = (Fo2 + 2Fc2)/3
3067 reflections	(Δ/σ)max = 0.005
186 parameters	Δρmax = 0.42 e Å−3
1 restraint	Δρmin = −0.73 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	0.46825 (3)	0.17165 (7)	0.04412 (4)	0.0546 (2)
Cl2	0.40676 (4)	−0.06394 (9)	0.31762 (4)	0.0740 (3)
S1	0.44325 (2)	0.54969 (6)	0.10219 (3)	0.03642 (17)
O1	0.50536 (6)	0.55754 (19)	0.10210 (9)	0.0465 (4)
O2	0.41625 (8)	0.68220 (18)	0.13769 (11)	0.0528 (4)
N1	0.41157 (8)	0.5283 (2)	0.00604 (11)	0.0404 (4)
H1N	0.4355 (10)	0.498 (3)	−0.0239 (14)	0.048*
C1	0.42987 (8)	0.3693 (2)	0.15700 (11)	0.0324 (4)
C2	0.44187 (8)	0.2097 (2)	0.13350 (12)	0.0343 (4)
C3	0.43374 (9)	0.0751 (2)	0.18203 (13)	0.0402 (5)
H3	0.4412	−0.0318	0.1659	0.048*
C4	0.41432 (9)	0.1028 (3)	0.25492 (12)	0.0423 (5)
C5	0.40168 (10)	0.2587 (3)	0.27941 (13)	0.0453 (5)
H5	0.3883	0.2746	0.3285	0.054*
C6	0.40921 (9)	0.3917 (3)	0.22994 (12)	0.0406 (4)
H6	0.4003	0.4978	0.2456	0.049*
C7	0.35076 (9)	0.4915 (2)	−0.02514 (12)	0.0383 (4)
C8	0.33728 (10)	0.4228 (3)	−0.10365 (14)	0.0437 (5)
H8	0.3675	0.3984	−0.1315	0.052*
C9	0.27908 (11)	0.3901 (3)	−0.14115 (16)	0.0556 (6)
C10	0.23500 (11)	0.4246 (3)	−0.09667 (18)	0.0612 (7)
H10	0.1958	0.4018	−0.1208	0.073*
C11	0.24769 (10)	0.4914 (3)	−0.01807 (16)	0.0539 (6)
C12	0.30625 (10)	0.5275 (3)	0.01805 (14)	0.0471 (5)
H12	0.3155	0.5750	0.0705	0.057*
C13	0.26428 (15)	0.3176 (5)	−0.2271 (2)	0.0863 (10)
H13A	0.2571	0.2010	−0.2235	0.104*
H13B	0.2968	0.3349	−0.2544	0.104*
H13C	0.2295	0.3706	−0.2580	0.104*
C14	0.19926 (13)	0.5276 (4)	0.0292 (2)	0.0767 (9)
H14A	0.1899	0.4286	0.0560	0.092*
H14B	0.1646	0.5660	−0.0086	0.092*
H14C	0.2125	0.6114	0.0700	0.092*

	U11	U22	U33	U12	U13	U23
Cl1	0.0766 (4)	0.0469 (3)	0.0478 (3)	0.0090 (3)	0.0306 (3)	−0.0059 (2)
Cl2	0.1009 (6)	0.0607 (4)	0.0620 (4)	−0.0197 (4)	0.0203 (4)	0.0207 (3)
S1	0.0393 (3)	0.0314 (3)	0.0382 (3)	−0.00622 (18)	0.0070 (2)	−0.00107 (18)
O1	0.0392 (8)	0.0546 (9)	0.0446 (8)	−0.0151 (6)	0.0059 (6)	0.0006 (7)
O2	0.0694 (11)	0.0308 (7)	0.0597 (10)	−0.0001 (7)	0.0167 (8)	−0.0068 (6)
N1	0.0357 (9)	0.0483 (10)	0.0374 (9)	−0.0037 (7)	0.0081 (7)	0.0039 (7)
C1	0.0316 (9)	0.0322 (9)	0.0332 (9)	−0.0036 (7)	0.0063 (7)	−0.0024 (7)
C2	0.0337 (9)	0.0357 (10)	0.0341 (9)	−0.0014 (8)	0.0082 (7)	−0.0040 (7)
C3	0.0422 (11)	0.0324 (10)	0.0451 (11)	−0.0033 (8)	0.0062 (9)	−0.0012 (8)
C4	0.0411 (11)	0.0447 (11)	0.0393 (10)	−0.0114 (9)	0.0035 (8)	0.0077 (9)
C5	0.0492 (12)	0.0544 (13)	0.0344 (10)	−0.0061 (10)	0.0134 (9)	−0.0029 (9)
C6	0.0444 (11)	0.0406 (11)	0.0383 (10)	−0.0020 (9)	0.0123 (8)	−0.0064 (8)
C7	0.0369 (10)	0.0346 (10)	0.0422 (10)	−0.0004 (8)	0.0049 (8)	0.0104 (8)
C8	0.0419 (11)	0.0406 (11)	0.0467 (12)	0.0004 (9)	0.0044 (9)	0.0049 (9)
C9	0.0465 (13)	0.0568 (14)	0.0572 (14)	−0.0022 (11)	−0.0044 (10)	0.0029 (11)
C10	0.0358 (12)	0.0689 (17)	0.0728 (17)	−0.0036 (11)	−0.0036 (11)	0.0097 (13)
C11	0.0374 (11)	0.0594 (14)	0.0655 (16)	0.0035 (10)	0.0117 (10)	0.0199 (12)
C12	0.0429 (12)	0.0516 (13)	0.0471 (12)	0.0007 (9)	0.0097 (9)	0.0080 (10)
C13	0.0644 (18)	0.106 (3)	0.077 (2)	−0.0030 (17)	−0.0139 (15)	−0.0246 (18)
C14	0.0469 (15)	0.100 (2)	0.087 (2)	0.0041 (14)	0.0234 (14)	0.0196 (18)

Cl1—C2	1.7296 (19)	C7—C8	1.384 (3)
Cl2—C4	1.727 (2)	C7—C12	1.392 (3)
S1—O2	1.4220 (16)	C8—C9	1.386 (3)
S1—O1	1.4343 (16)	C8—H8	0.9300
S1—N1	1.6148 (18)	C9—C10	1.395 (4)
S1—C1	1.7739 (19)	C9—C13	1.506 (4)
N1—C7	1.425 (3)	C10—C11	1.379 (4)
N1—H1N	0.845 (16)	C10—H10	0.9300
C1—C2	1.390 (3)	C11—C12	1.393 (3)
C1—C6	1.390 (3)	C11—C14	1.512 (4)
C2—C3	1.385 (3)	C12—H12	0.9300
C3—C4	1.381 (3)	C13—H13A	0.9600
C3—H3	0.9300	C13—H13B	0.9600
C4—C5	1.372 (3)	C13—H13C	0.9600
C5—C6	1.380 (3)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—H6	0.9300	C14—H14C	0.9600
O2—S1—O1	119.16 (10)	C12—C7—N1	123.1 (2)
O2—S1—N1	109.55 (10)	C7—C8—C9	120.6 (2)
O1—S1—N1	105.02 (9)	C7—C8—H8	119.7
O2—S1—C1	105.91 (9)	C9—C8—H8	119.7
O1—S1—C1	108.22 (9)	C8—C9—C10	118.1 (2)
N1—S1—C1	108.67 (9)	C8—C9—C13	120.6 (2)
C7—N1—S1	126.50 (14)	C10—C9—C13	121.3 (2)
C7—N1—H1N	116.2 (17)	C11—C10—C9	122.1 (2)
S1—N1—H1N	112.5 (17)	C11—C10—H10	118.9
C2—C1—C6	118.90 (17)	C9—C10—H10	118.9
C2—C1—S1	123.77 (14)	C10—C11—C12	119.2 (2)
C6—C1—S1	117.23 (15)	C10—C11—C14	121.3 (2)
C3—C2—C1	120.70 (17)	C12—C11—C14	119.5 (3)
C3—C2—Cl1	117.57 (15)	C7—C12—C11	119.3 (2)
C1—C2—Cl1	121.72 (15)	C7—C12—H12	120.3
C4—C3—C2	118.62 (19)	C11—C12—H12	120.3
C4—C3—H3	120.7	C9—C13—H13A	109.5
C2—C3—H3	120.7	C9—C13—H13B	109.5
C5—C4—C3	121.99 (18)	H13A—C13—H13B	109.5
C5—C4—Cl2	119.18 (16)	C9—C13—H13C	109.5
C3—C4—Cl2	118.83 (17)	H13A—C13—H13C	109.5
C4—C5—C6	118.80 (19)	H13B—C13—H13C	109.5
C4—C5—H5	120.6	C11—C14—H14A	109.5
C6—C5—H5	120.6	C11—C14—H14B	109.5
C5—C6—C1	120.96 (19)	H14A—C14—H14B	109.5
C5—C6—H6	119.5	C11—C14—H14C	109.5
C1—C6—H6	119.5	H14A—C14—H14C	109.5
C8—C7—C12	120.7 (2)	H14B—C14—H14C	109.5
C8—C7—N1	116.14 (18)
O2—S1—N1—C7	−60.3 (2)	Cl2—C4—C5—C6	178.44 (17)
O1—S1—N1—C7	170.56 (17)	C4—C5—C6—C1	−0.7 (3)
C1—S1—N1—C7	54.9 (2)	C2—C1—C6—C5	1.2 (3)
O2—S1—C1—C2	170.58 (16)	S1—C1—C6—C5	−175.34 (16)
O1—S1—C1—C2	−60.58 (18)	S1—N1—C7—C8	−158.16 (16)
N1—S1—C1—C2	52.96 (18)	S1—N1—C7—C12	24.4 (3)
O2—S1—C1—C6	−13.03 (18)	C12—C7—C8—C9	0.7 (3)
O1—S1—C1—C6	115.81 (16)	N1—C7—C8—C9	−176.8 (2)
N1—S1—C1—C6	−130.65 (16)	C7—C8—C9—C10	−1.5 (3)
C6—C1—C2—C3	−0.4 (3)	C7—C8—C9—C13	179.1 (3)
S1—C1—C2—C3	175.98 (15)	C8—C9—C10—C11	0.9 (4)
C6—C1—C2—Cl1	−179.47 (15)	C13—C9—C10—C11	−179.8 (3)
S1—C1—C2—Cl1	−3.1 (2)	C9—C10—C11—C12	0.7 (4)
C1—C2—C3—C4	−1.0 (3)	C9—C10—C11—C14	−179.9 (3)
Cl1—C2—C3—C4	178.18 (16)	C8—C7—C12—C11	0.9 (3)
C2—C3—C4—C5	1.5 (3)	N1—C7—C12—C11	178.2 (2)
C2—C3—C4—Cl2	−177.60 (15)	C10—C11—C12—C7	−1.5 (3)
C3—C4—C5—C6	−0.6 (3)	C14—C11—C12—C7	179.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.85 (2)	2.11 (2)	2.948 (2)	176 (2)
C3—H3···O2ii	0.93	2.40	3.264 (2)	154 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.85 (2)	2.11 (2)	2.948 (2)	176 (2)
C3—H3⋯O2ii	0.93	2.40	3.264 (2)	154 (1)

Symmetry codes: (i) ; (ii) .