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

In the crystal structure of the title compound, C(14)H(13)Cl(2)NO(2)S, the configurations of the N-C bond with respect to the S=O bonds are trans and gauche. The mol-ecule is bent at the S atom with a C-SO(2)-NH-C torsion angle of -69.7 (2)°. The conformation of the N-H bond is syn to the 3-chloro group in the substituted aniline ring. The two benzene rings are tilted with respect to each other by 82.4 (1)°. The presence of N-H⋯O(S) hydrogen bonding packs the mol-ecules into supra-molecular chains along the b axis.

Related literature

For our study of the effect of substituents on the structures of N-(ar­yl)-aryl­sulfonamides, see: Gowda et al. (2008 ▶; 2009 ▶). For related structures, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C14H13Cl2NO2S

M = 330.21

Monoclinic,

a = 8.8046 (7) Å

b = 9.2688 (8) Å

c = 18.947 (1) Å

β = 99.644 (8)°

V = 1524.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.56 mm−1

T = 299 K

0.44 × 0.40 × 0.38 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.790, T max = 0.815

10274 measured reflections

3064 independent reflections

2618 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.100

S = 1.05

3064 reflections

186 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.39 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 datablocks I, global. DOI: 10.1107/S1600536809028840/tk2510sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028840/tk2510Isup2.hkl

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

C14H13Cl2NO2S	F(000) = 680
Mr = 330.21	Dx = 1.439 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4751 reflections
a = 8.8046 (7) Å	θ = 3.0–27.6°
b = 9.2688 (8) Å	µ = 0.56 mm−1
c = 18.947 (1) Å	T = 299 K
β = 99.644 (8)°	Prism, colourless
V = 1524.4 (2) Å3	0.44 × 0.40 × 0.38 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	3064 independent reflections
Radiation source: fine-focus sealed tube	2618 reflections with I > 2σ(I)
graphite	Rint = 0.013
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −9→10
Tmin = 0.790, Tmax = 0.815	k = −11→11
10274 measured reflections	l = −23→23

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0506P)2 + 0.7353P] where P = (Fo2 + 2Fc2)/3
3064 reflections	(Δ/σ)max = 0.007
186 parameters	Δρmax = 0.27 e Å−3
1 restraint	Δρmin = −0.39 e Å−3

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	0.7751 (2)	0.1105 (2)	0.26937 (9)	0.0342 (4)
C2	0.7595 (2)	0.0272 (2)	0.32852 (10)	0.0405 (4)
H2	0.8407	−0.0308	0.3497	0.049*
C3	0.6243 (2)	0.0301 (2)	0.35611 (10)	0.0425 (5)
C4	0.5020 (2)	0.1148 (2)	0.32506 (10)	0.0425 (5)
C5	0.5178 (2)	0.1972 (3)	0.26616 (10)	0.0472 (5)
H5	0.4360	0.2544	0.2449	0.057*
C6	0.6528 (2)	0.1963 (2)	0.23813 (10)	0.0441 (5)
H6	0.6618	0.2529	0.1985	0.053*
C7	0.8600 (2)	0.1276 (2)	0.09846 (9)	0.0334 (4)
C8	0.8733 (2)	−0.0147 (2)	0.07500 (10)	0.0363 (4)
C9	0.7833 (2)	−0.0518 (2)	0.01025 (10)	0.0410 (4)
H9	0.7907	−0.1453	−0.0067	0.049*
C10	0.6828 (2)	0.0432 (2)	−0.03070 (10)	0.0403 (4)
C11	0.6726 (2)	0.1824 (2)	−0.00542 (10)	0.0434 (5)
H11	0.6057	0.2479	−0.0317	0.052*
C12	0.7608 (2)	0.2250 (2)	0.05836 (10)	0.0406 (4)
H12	0.7537	0.3191	0.0746	0.049*
C13	0.9776 (3)	−0.1262 (2)	0.11551 (13)	0.0515 (5)
H13A	0.9396	−0.1519	0.1584	0.062*
H13B	1.0797	−0.0874	0.1277	0.062*
H13C	0.9800	−0.2103	0.0862	0.062*
C14	0.5881 (3)	−0.0036 (3)	−0.10031 (11)	0.0529 (5)
H14A	0.5855	−0.1071	−0.1026	0.064*
H14B	0.6331	0.0336	−0.1394	0.064*
H14C	0.4851	0.0328	−0.1035	0.064*
N1	0.91696 (19)	0.1015 (2)	0.24438 (8)	0.0407 (4)
H1N	0.976 (2)	0.035 (2)	0.2605 (12)	0.049*
O1	0.92732 (17)	0.33947 (15)	0.18616 (7)	0.0471 (4)
O2	1.12802 (16)	0.15602 (19)	0.18124 (8)	0.0530 (4)
Cl1	0.61158 (9)	−0.07351 (7)	0.43079 (4)	0.0753 (2)
Cl2	0.33330 (7)	0.12189 (9)	0.36022 (3)	0.0680 (2)
S1	0.96962 (5)	0.19135 (5)	0.17881 (2)	0.03717 (14)

	U11	U22	U33	U12	U13	U23
C1	0.0378 (10)	0.0348 (9)	0.0301 (8)	−0.0019 (7)	0.0057 (7)	−0.0059 (7)
C2	0.0482 (11)	0.0329 (10)	0.0418 (10)	0.0070 (8)	0.0121 (8)	0.0008 (8)
C3	0.0561 (12)	0.0323 (10)	0.0428 (10)	−0.0013 (9)	0.0190 (9)	−0.0015 (8)
C4	0.0378 (10)	0.0490 (12)	0.0424 (10)	−0.0053 (9)	0.0116 (8)	−0.0117 (9)
C5	0.0372 (11)	0.0635 (14)	0.0389 (10)	0.0079 (9)	0.0010 (8)	−0.0018 (9)
C6	0.0414 (11)	0.0577 (13)	0.0325 (9)	0.0056 (9)	0.0045 (8)	0.0039 (9)
C7	0.0347 (9)	0.0356 (10)	0.0313 (8)	−0.0044 (7)	0.0093 (7)	0.0007 (7)
C8	0.0373 (9)	0.0337 (9)	0.0398 (9)	−0.0012 (8)	0.0121 (7)	0.0019 (7)
C9	0.0476 (11)	0.0346 (10)	0.0421 (10)	−0.0028 (8)	0.0112 (8)	−0.0050 (8)
C10	0.0438 (11)	0.0453 (11)	0.0330 (9)	−0.0057 (9)	0.0100 (8)	−0.0020 (8)
C11	0.0520 (12)	0.0418 (11)	0.0353 (9)	0.0052 (9)	0.0037 (8)	0.0059 (8)
C12	0.0517 (11)	0.0336 (10)	0.0370 (9)	0.0028 (8)	0.0087 (8)	0.0008 (8)
C13	0.0532 (13)	0.0401 (11)	0.0588 (13)	0.0051 (10)	0.0027 (10)	0.0035 (10)
C14	0.0577 (13)	0.0602 (14)	0.0391 (11)	−0.0061 (11)	0.0032 (9)	−0.0050 (10)
N1	0.0381 (9)	0.0497 (10)	0.0350 (8)	0.0079 (7)	0.0080 (7)	0.0061 (7)
O1	0.0542 (9)	0.0374 (8)	0.0481 (8)	−0.0112 (6)	0.0038 (6)	−0.0065 (6)
O2	0.0326 (7)	0.0724 (11)	0.0544 (9)	−0.0062 (7)	0.0087 (6)	−0.0024 (7)
Cl1	0.0973 (5)	0.0599 (4)	0.0818 (5)	0.0169 (3)	0.0531 (4)	0.0292 (3)
Cl2	0.0443 (3)	0.0965 (5)	0.0679 (4)	−0.0024 (3)	0.0234 (3)	−0.0037 (3)
S1	0.0339 (2)	0.0413 (3)	0.0365 (2)	−0.00631 (19)	0.00630 (18)	−0.00184 (19)

C1—C2	1.387 (3)	C9—C10	1.389 (3)
C1—C6	1.389 (3)	C9—H9	0.9300
C1—N1	1.410 (2)	C10—C11	1.385 (3)
C2—C3	1.379 (3)	C10—C14	1.501 (3)
C2—H2	0.9300	C11—C12	1.380 (3)
C3—C4	1.382 (3)	C11—H11	0.9300
C3—Cl1	1.729 (2)	C12—H12	0.9300
C4—C5	1.378 (3)	C13—H13A	0.9600
C4—Cl2	1.7283 (19)	C13—H13B	0.9600
C5—C6	1.381 (3)	C13—H13C	0.9600
C5—H5	0.9300	C14—H14A	0.9600
C6—H6	0.9300	C14—H14B	0.9600
C7—C12	1.391 (3)	C14—H14C	0.9600
C7—C8	1.403 (3)	N1—S1	1.6264 (17)
C7—S1	1.7623 (18)	N1—H1N	0.833 (16)
C8—C9	1.387 (3)	O1—S1	1.4353 (15)
C8—C13	1.505 (3)	O2—S1	1.4258 (15)
C2—C1—C6	119.25 (18)	C9—C10—C14	121.03 (19)
C2—C1—N1	116.83 (17)	C12—C11—C10	120.66 (18)
C6—C1—N1	123.92 (17)	C12—C11—H11	119.7
C3—C2—C1	120.29 (18)	C10—C11—H11	119.7
C3—C2—H2	119.9	C11—C12—C7	120.17 (18)
C1—C2—H2	119.9	C11—C12—H12	119.9
C2—C3—C4	120.68 (18)	C7—C12—H12	119.9
C2—C3—Cl1	118.55 (16)	C8—C13—H13A	109.5
C4—C3—Cl1	120.77 (15)	C8—C13—H13B	109.5
C5—C4—C3	118.87 (18)	H13A—C13—H13B	109.5
C5—C4—Cl2	120.05 (16)	C8—C13—H13C	109.5
C3—C4—Cl2	121.06 (16)	H13A—C13—H13C	109.5
C4—C5—C6	121.20 (19)	H13B—C13—H13C	109.5
C4—C5—H5	119.4	C10—C14—H14A	109.5
C6—C5—H5	119.4	C10—C14—H14B	109.5
C5—C6—C1	119.71 (18)	H14A—C14—H14B	109.5
C5—C6—H6	120.1	C10—C14—H14C	109.5
C1—C6—H6	120.1	H14A—C14—H14C	109.5
C12—C7—C8	121.01 (17)	H14B—C14—H14C	109.5
C12—C7—S1	117.22 (14)	C1—N1—S1	127.44 (14)
C8—C7—S1	121.76 (14)	C1—N1—H1N	117.1 (16)
C9—C8—C7	116.59 (17)	S1—N1—H1N	114.8 (16)
C9—C8—C13	119.36 (18)	O2—S1—O1	119.00 (9)
C7—C8—C13	124.05 (18)	O2—S1—N1	105.08 (9)
C8—C9—C10	123.55 (18)	O1—S1—N1	107.69 (9)
C8—C9—H9	118.2	O2—S1—C7	109.99 (9)
C10—C9—H9	118.2	O1—S1—C7	106.92 (9)
C11—C10—C9	118.01 (18)	N1—S1—C7	107.66 (9)
C11—C10—C14	120.96 (19)
C6—C1—C2—C3	−0.2 (3)	C8—C9—C10—C11	0.2 (3)
N1—C1—C2—C3	−179.96 (17)	C8—C9—C10—C14	−179.83 (18)
C1—C2—C3—C4	0.5 (3)	C9—C10—C11—C12	0.4 (3)
C1—C2—C3—Cl1	−179.00 (14)	C14—C10—C11—C12	−179.54 (19)
C2—C3—C4—C5	−0.3 (3)	C10—C11—C12—C7	−0.7 (3)
Cl1—C3—C4—C5	179.16 (16)	C8—C7—C12—C11	0.3 (3)
C2—C3—C4—Cl2	−178.74 (15)	S1—C7—C12—C11	179.45 (15)
Cl1—C3—C4—Cl2	0.7 (2)	C2—C1—N1—S1	−177.17 (15)
C3—C4—C5—C6	−0.1 (3)	C6—C1—N1—S1	3.1 (3)
Cl2—C4—C5—C6	178.33 (16)	C1—N1—S1—O2	173.04 (16)
C4—C5—C6—C1	0.4 (3)	C1—N1—S1—O1	45.23 (19)
C2—C1—C6—C5	−0.2 (3)	C1—N1—S1—C7	−69.74 (18)
N1—C1—C6—C5	179.52 (18)	C12—C7—S1—O2	−129.57 (15)
C12—C7—C8—C9	0.3 (3)	C8—C7—S1—O2	49.56 (17)
S1—C7—C8—C9	−178.82 (13)	C12—C7—S1—O1	0.97 (17)
C12—C7—C8—C13	−179.77 (19)	C8—C7—S1—O1	−179.90 (14)
S1—C7—C8—C13	1.1 (3)	C12—C7—S1—N1	116.45 (15)
C7—C8—C9—C10	−0.6 (3)	C8—C7—S1—N1	−64.42 (16)
C13—C8—C9—C10	179.49 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.83 (2)	2.18 (2)	2.984 (2)	164 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.833 (16)	2.176 (17)	2.984 (2)	164 (2)

Symmetry code: (i) .