N-(3,5-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 conformation of the N-C bond in the C-SO(2)-NH-C segment has gauche torsions with respect to the S=O bonds. The mol-ecule is bent at the N atom, with an C-SO(2)-NH-C torsion angle of -54.9 (3)°. The two benzene rings are tilted relative to each other by 82.3 (2)°. The mol-ecules are linked into centrosymmetric R(2) (2)(8) motifs by N-H⋯O hydrogen bonds and C-H⋯π inter-actions along [100].

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. (2008 ▶, 2009 ▶). For related structures, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H13Cl2NO2S

M = 330.21

Monoclinic,

a = 23.085 (3) Å

b = 8.113 (2) Å

c = 16.503 (3) Å

β = 102.03 (2)°

V = 3022.9 (10) Å3

Z = 8

Cu Kα radiation

μ = 5.16 mm−1

T = 299 K

0.55 × 0.45 × 0.38 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.164, T max = 0.245

7561 measured reflections

2690 independent reflections

2340 reflections with I > 2σ(I)

R int = 0.089

3 standard reflections every 120 min intensity decay: 1.0%

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.189

S = 1.14

2690 reflections

187 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.56 e Å−3

Δρmin = −0.46 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/S1600536810013504/bx2275sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013504/bx2275Isup2.hkl

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

C14H13Cl2NO2S	F(000) = 1360
Mr = 330.21	Dx = 1.451 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 23.085 (3) Å	θ = 5.5–18.6°
b = 8.113 (2) Å	µ = 5.16 mm−1
c = 16.503 (3) Å	T = 299 K
β = 102.03 (2)°	Prism, colourless
V = 3022.9 (10) Å3	0.55 × 0.45 × 0.38 mm
Z = 8

Enraf–Nonius CAD-4 diffractometer	2340 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.089
graphite	θmax = 66.9°, θmin = 3.9°
ω/2θ scans	h = −15→27
Absorption correction: ψ scan (North et al., 1968)	k = −9→9
Tmin = 0.164, Tmax = 0.245	l = −19→19
7561 measured reflections	3 standard reflections every 120 min
2690 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)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.189	w = 1/[σ2(Fo2) + (0.1031P)2 + 3.0862P] where P = (Fo2 + 2Fc2)/3
S = 1.14	(Δ/σ)max = 0.006
2690 reflections	Δρmax = 0.56 e Å−3
187 parameters	Δρmin = −0.46 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00090 (16)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.43013 (12)	0.1399 (3)	0.15596 (17)	0.0411 (6)
C2	0.44290 (12)	0.2976 (4)	0.13142 (18)	0.0442 (6)
C3	0.43210 (14)	0.4268 (4)	0.1793 (2)	0.0509 (7)
H3	0.4397	0.5330	0.1631	0.061*
C4	0.41035 (13)	0.4069 (4)	0.2511 (2)	0.0507 (7)
C5	0.39736 (14)	0.2499 (4)	0.27317 (19)	0.0541 (8)
H5	0.3822	0.2338	0.3205	0.065*
C6	0.40659 (14)	0.1169 (4)	0.22618 (19)	0.0505 (7)
H6	0.3971	0.0114	0.2412	0.061*
C7	0.35181 (14)	0.0098 (4)	−0.0243 (2)	0.0479 (7)
C8	0.33700 (14)	0.0724 (4)	−0.1038 (2)	0.0537 (8)
H8	0.3663	0.0948	−0.1332	0.064*
C9	0.27851 (16)	0.1011 (5)	−0.1390 (2)	0.0653 (9)
C10	0.23406 (16)	0.0720 (6)	−0.0964 (3)	0.0728 (11)
H10	0.1946	0.0926	−0.1205	0.087*
C11	0.24997 (17)	0.0121 (5)	−0.0178 (3)	0.0658 (10)
C12	0.30817 (16)	−0.0218 (5)	0.0207 (2)	0.0594 (9)
H12	0.3176	−0.0639	0.0742	0.071*
C13	0.46692 (19)	0.3326 (5)	0.0555 (2)	0.0657 (10)
H13A	0.4371	0.3088	0.0070	0.079*
H13B	0.5010	0.2648	0.0557	0.079*
H13C	0.4780	0.4466	0.0551	0.079*
C14	0.4006 (2)	0.5542 (5)	0.3010 (3)	0.0769 (12)
H14A	0.3644	0.6078	0.2751	0.092*
H14B	0.4331	0.6296	0.3040	0.092*
H14C	0.3982	0.5200	0.3558	0.092*
Cl1	0.26077 (5)	0.1724 (2)	−0.23956 (8)	0.1056 (6)
Cl2	0.19530 (5)	−0.0269 (2)	0.03757 (9)	0.1007 (5)
N1	0.41245 (12)	−0.0223 (4)	0.00734 (18)	0.0542 (7)
H1N	0.4333 (19)	0.011 (5)	−0.027 (3)	0.065*
O1	0.50684 (10)	−0.0457 (3)	0.10170 (15)	0.0615 (7)
O2	0.41982 (13)	−0.1739 (3)	0.13907 (17)	0.0680 (7)
S1	0.44494 (3)	−0.03942 (9)	0.10412 (5)	0.0485 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0405 (13)	0.0437 (14)	0.0396 (13)	0.0051 (11)	0.0094 (11)	0.0025 (11)
C2	0.0423 (14)	0.0489 (15)	0.0427 (14)	0.0023 (12)	0.0115 (11)	0.0066 (12)
C3	0.0515 (16)	0.0429 (15)	0.0588 (18)	0.0019 (13)	0.0128 (14)	0.0043 (13)
C4	0.0469 (15)	0.0571 (18)	0.0489 (16)	0.0066 (13)	0.0117 (13)	−0.0040 (14)
C5	0.0572 (17)	0.0655 (19)	0.0440 (15)	0.0038 (15)	0.0207 (13)	0.0031 (14)
C6	0.0584 (17)	0.0503 (16)	0.0460 (16)	0.0012 (13)	0.0181 (13)	0.0088 (13)
C7	0.0446 (15)	0.0497 (15)	0.0491 (16)	0.0012 (12)	0.0092 (12)	−0.0122 (13)
C8	0.0481 (16)	0.0595 (18)	0.0534 (18)	0.0003 (14)	0.0105 (13)	−0.0058 (14)
C9	0.0530 (18)	0.079 (2)	0.059 (2)	−0.0018 (17)	−0.0004 (15)	−0.0007 (18)
C10	0.0436 (17)	0.094 (3)	0.076 (3)	0.0021 (18)	0.0022 (17)	−0.010 (2)
C11	0.0499 (18)	0.081 (2)	0.069 (2)	−0.0055 (17)	0.0176 (17)	−0.0172 (19)
C12	0.0541 (18)	0.072 (2)	0.0534 (19)	−0.0005 (15)	0.0141 (15)	−0.0095 (15)
C13	0.085 (2)	0.062 (2)	0.059 (2)	−0.0049 (18)	0.0346 (19)	0.0102 (16)
C14	0.090 (3)	0.071 (3)	0.075 (3)	0.010 (2)	0.028 (2)	−0.0170 (19)
Cl1	0.0679 (7)	0.1625 (14)	0.0765 (7)	−0.0020 (7)	−0.0073 (5)	0.0331 (8)
Cl2	0.0616 (6)	0.1549 (13)	0.0940 (9)	−0.0108 (6)	0.0353 (6)	−0.0121 (8)
N1	0.0481 (14)	0.0703 (18)	0.0441 (14)	0.0076 (12)	0.0096 (12)	−0.0056 (12)
O1	0.0525 (13)	0.0771 (17)	0.0535 (13)	0.0247 (11)	0.0077 (10)	−0.0028 (11)
O2	0.0908 (18)	0.0436 (12)	0.0717 (16)	0.0060 (12)	0.0214 (14)	0.0064 (11)
S1	0.0521 (5)	0.0462 (5)	0.0475 (5)	0.0114 (3)	0.0106 (3)	0.0007 (3)

C1—C6	1.391 (4)	C9—C10	1.379 (6)
C1—C2	1.392 (4)	C9—Cl1	1.725 (4)
C1—S1	1.757 (3)	C10—C11	1.362 (6)
C2—C3	1.366 (4)	C10—H10	0.9300
C2—C13	1.500 (4)	C11—C12	1.389 (5)
C3—C4	1.389 (5)	C11—Cl2	1.735 (4)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.375 (5)	C13—H13A	0.9600
C4—C14	1.495 (5)	C13—H13B	0.9600
C5—C6	1.371 (5)	C13—H13C	0.9600
C5—H5	0.9300	C14—H14A	0.9600
C6—H6	0.9300	C14—H14B	0.9600
C7—C8	1.381 (5)	C14—H14C	0.9600
C7—C12	1.394 (5)	N1—S1	1.623 (3)
C7—N1	1.413 (4)	N1—H1N	0.86 (4)
C8—C9	1.374 (5)	O1—S1	1.439 (2)
C8—H8	0.9300	O2—S1	1.414 (3)
C6—C1—C2	120.6 (3)	C9—C10—H10	121.2
C6—C1—S1	116.4 (2)	C10—C11—C12	123.3 (4)
C2—C1—S1	123.0 (2)	C10—C11—Cl2	119.0 (3)
C3—C2—C1	117.5 (3)	C12—C11—Cl2	117.6 (3)
C3—C2—C13	118.8 (3)	C11—C12—C7	117.2 (4)
C1—C2—C13	123.7 (3)	C11—C12—H12	121.4
C2—C3—C4	123.1 (3)	C7—C12—H12	121.4
C2—C3—H3	118.5	C2—C13—H13A	109.5
C4—C3—H3	118.5	C2—C13—H13B	109.5
C5—C4—C3	118.1 (3)	H13A—C13—H13B	109.5
C5—C4—C14	121.9 (3)	C2—C13—H13C	109.5
C3—C4—C14	120.0 (3)	H13A—C13—H13C	109.5
C6—C5—C4	120.7 (3)	H13B—C13—H13C	109.5
C6—C5—H5	119.6	C4—C14—H14A	109.5
C4—C5—H5	119.6	C4—C14—H14B	109.5
C5—C6—C1	120.0 (3)	H14A—C14—H14B	109.5
C5—C6—H6	120.0	C4—C14—H14C	109.5
C1—C6—H6	120.0	H14A—C14—H14C	109.5
C8—C7—C12	120.7 (3)	H14B—C14—H14C	109.5
C8—C7—N1	116.7 (3)	C7—N1—S1	126.8 (2)
C12—C7—N1	122.6 (3)	C7—N1—H1N	110 (3)
C9—C8—C7	119.4 (3)	S1—N1—H1N	118 (3)
C9—C8—H8	120.3	O2—S1—O1	118.57 (16)
C7—C8—H8	120.3	O2—S1—N1	108.85 (17)
C8—C9—C10	121.7 (4)	O1—S1—N1	103.52 (15)
C8—C9—Cl1	118.6 (3)	O2—S1—C1	107.61 (14)
C10—C9—Cl1	119.7 (3)	O1—S1—C1	109.74 (14)
C11—C10—C9	117.7 (3)	N1—S1—C1	108.13 (14)
C11—C10—H10	121.2
C6—C1—C2—C3	0.8 (4)	Cl1—C9—C10—C11	178.5 (3)
S1—C1—C2—C3	−176.7 (2)	C9—C10—C11—C12	−0.5 (7)
C6—C1—C2—C13	−178.5 (3)	C9—C10—C11—Cl2	−179.7 (3)
S1—C1—C2—C13	4.0 (4)	C10—C11—C12—C7	0.7 (6)
C1—C2—C3—C4	1.3 (5)	Cl2—C11—C12—C7	180.0 (3)
C13—C2—C3—C4	−179.5 (3)	C8—C7—C12—C11	0.0 (5)
C2—C3—C4—C5	−2.2 (5)	N1—C7—C12—C11	−178.8 (3)
C2—C3—C4—C14	179.0 (3)	C8—C7—N1—S1	159.3 (3)
C3—C4—C5—C6	1.0 (5)	C12—C7—N1—S1	−21.8 (5)
C14—C4—C5—C6	179.9 (3)	C7—N1—S1—O2	61.7 (3)
C4—C5—C6—C1	0.9 (5)	C7—N1—S1—O1	−171.3 (3)
C2—C1—C6—C5	−1.9 (5)	C7—N1—S1—C1	−54.9 (3)
S1—C1—C6—C5	175.8 (2)	C6—C1—S1—O2	9.6 (3)
C12—C7—C8—C9	−1.0 (5)	C2—C1—S1—O2	−172.8 (3)
N1—C7—C8—C9	177.9 (3)	C6—C1—S1—O1	−120.7 (3)
C7—C8—C9—C10	1.3 (6)	C2—C1—S1—O1	56.9 (3)
C7—C8—C9—Cl1	−177.8 (3)	C6—C1—S1—N1	127.0 (2)
C8—C9—C10—C11	−0.5 (7)	C2—C1—S1—N1	−55.4 (3)

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.86 (4)	2.05 (5)	2.900 (4)	168 (4)
C10—H10···Cg1ii	0.93	2.92	3.834 (4)	168

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.86 (4)	2.05 (5)	2.900 (4)	168 (4)
C10—H10⋯Cg1ii	0.93	2.92	3.834 (4)	168

Symmetry codes: (i) ; (ii) .