N-(2,6-Dichloro-phen-yl)-4-methyl-benzene-sulfonamide.

In the title compound, C(13)H(11)Cl(2)NO(2)S, the mol-ecule is bent at the S atom with a C-SO(2)-NH-C torsion angle of -90.4 (2)°. The sulfonyl benzene and the aniline benzene rings are tilted relative to each other by 51.7 (1)°. In the crystal, mol-ecules are linked by N- H⋯O inter-actions into chains with graph-set notation C(4) along [100].

Related literature

For our study of the effect of substituents on the structures of N-(ar­yl)aryl­sulfonamides, see: Gowda et al. (2009 ▶); Nirmala et al. (2010 ▶); Shakuntala et al. (2010 ▶). For related structures, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H11Cl2NO2S

M = 316.19

Monoclinic,

a = 5.0456 (6) Å

b = 17.128 (2) Å

c = 16.540 (2) Å

β = 97.13 (1)°

V = 1418.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.60 mm−1

T = 293 K

0.55 × 0.28 × 0.25 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.734, T max = 0.864

5631 measured reflections

2904 independent reflections

2493 reflections with I > 2σ(I)

R int = 0.011

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.102

S = 1.05

2904 reflections

176 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.48 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/S1600536810051792/bx2335sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051792/bx2335Isup2.hkl

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

C13H11Cl2NO2S	F(000) = 648
Mr = 316.19	Dx = 1.481 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3098 reflections
a = 5.0456 (6) Å	θ = 3.4–27.7°
b = 17.128 (2) Å	µ = 0.60 mm−1
c = 16.540 (2) Å	T = 293 K
β = 97.13 (1)°	Rod, colourless
V = 1418.4 (3) Å3	0.55 × 0.28 × 0.25 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2904 independent reflections
Radiation source: fine-focus sealed tube	2493 reflections with I > 2σ(I)
graphite	Rint = 0.011
Rotation method data acquisition using ω and phi scans	θmax = 26.4°, θmin = 3.4°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −3→6
Tmin = 0.734, Tmax = 0.864	k = −21→18
5631 measured reflections	l = −20→15

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0469P)2 + 0.7136P] where P = (Fo2 + 2Fc2)/3
2904 reflections	(Δ/σ)max = 0.028
176 parameters	Δρmax = 0.30 e Å−3
1 restraint	Δρmin = −0.48 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	0.0019 (4)	0.70942 (11)	0.33030 (12)	0.0361 (4)
C2	−0.2076 (4)	0.76146 (13)	0.32461 (14)	0.0471 (5)
H2	−0.3280	0.7645	0.2773	0.057*
C3	−0.2359 (5)	0.80913 (14)	0.39037 (16)	0.0559 (6)
H3	−0.3784	0.8439	0.3869	0.067*
C4	−0.0594 (5)	0.80678 (14)	0.46089 (15)	0.0537 (6)
C5	0.1467 (5)	0.75322 (15)	0.46540 (15)	0.0582 (6)
H5	0.2656	0.7498	0.5130	0.070*
C6	0.1799 (5)	0.70457 (14)	0.40068 (14)	0.0508 (5)
H6	0.3202	0.6690	0.4045	0.061*
C7	−0.0179 (4)	0.50337 (11)	0.28274 (13)	0.0387 (4)
C8	0.1533 (5)	0.45552 (13)	0.24465 (16)	0.0521 (6)
C9	0.2543 (6)	0.38721 (15)	0.2808 (2)	0.0736 (8)
H9	0.3728	0.3570	0.2554	0.088*
C10	0.1807 (7)	0.36409 (16)	0.3536 (2)	0.0793 (9)
H10	0.2488	0.3180	0.3776	0.095*
C11	0.0071 (6)	0.40828 (15)	0.39182 (17)	0.0674 (7)
H11	−0.0466	0.3917	0.4408	0.081*
C12	−0.0877 (4)	0.47785 (13)	0.35667 (14)	0.0471 (5)
C13	−0.0895 (7)	0.8623 (2)	0.5296 (2)	0.0855 (9)
H13A	−0.2690	0.8819	0.5242	0.103*
H13B	0.0328	0.9050	0.5278	0.103*
H13C	−0.0513	0.8354	0.5807	0.103*
N1	−0.1228 (3)	0.57274 (10)	0.24474 (10)	0.0388 (4)
H1N	−0.286 (3)	0.5809 (14)	0.2422 (14)	0.047*
O1	0.3260 (3)	0.63094 (9)	0.25207 (10)	0.0495 (4)
O2	−0.0611 (3)	0.69646 (9)	0.17450 (9)	0.0538 (4)
Cl1	0.23560 (17)	0.47929 (4)	0.14965 (5)	0.0797 (3)
Cl2	−0.30503 (14)	0.53278 (4)	0.40686 (4)	0.0675 (2)
S1	0.05144 (9)	0.65342 (3)	0.24407 (3)	0.03684 (15)

	U11	U22	U33	U12	U13	U23
C1	0.0349 (9)	0.0306 (9)	0.0445 (10)	−0.0027 (7)	0.0116 (8)	−0.0009 (8)
C2	0.0412 (11)	0.0452 (12)	0.0547 (12)	0.0063 (9)	0.0046 (9)	−0.0015 (10)
C3	0.0526 (13)	0.0481 (13)	0.0695 (15)	0.0120 (10)	0.0170 (12)	−0.0079 (11)
C4	0.0646 (14)	0.0481 (12)	0.0520 (13)	−0.0031 (11)	0.0211 (11)	−0.0068 (10)
C5	0.0648 (15)	0.0631 (15)	0.0456 (12)	0.0016 (12)	0.0021 (10)	−0.0030 (11)
C6	0.0508 (12)	0.0485 (12)	0.0526 (12)	0.0097 (10)	0.0045 (10)	0.0011 (10)
C7	0.0349 (10)	0.0309 (9)	0.0502 (11)	−0.0052 (8)	0.0040 (8)	−0.0045 (8)
C8	0.0499 (12)	0.0367 (11)	0.0716 (15)	−0.0060 (9)	0.0150 (11)	−0.0127 (10)
C9	0.0655 (16)	0.0384 (13)	0.117 (3)	0.0088 (12)	0.0133 (16)	−0.0165 (15)
C10	0.085 (2)	0.0417 (14)	0.105 (3)	0.0090 (14)	−0.0109 (18)	0.0073 (15)
C11	0.0817 (18)	0.0513 (14)	0.0654 (16)	−0.0093 (13)	−0.0055 (13)	0.0132 (12)
C12	0.0463 (12)	0.0438 (11)	0.0502 (12)	−0.0056 (9)	0.0021 (9)	−0.0019 (9)
C13	0.104 (2)	0.086 (2)	0.0706 (18)	0.0060 (19)	0.0242 (17)	−0.0281 (17)
N1	0.0267 (7)	0.0374 (9)	0.0524 (10)	−0.0016 (7)	0.0047 (7)	−0.0004 (7)
O1	0.0310 (7)	0.0471 (8)	0.0728 (10)	−0.0049 (6)	0.0158 (7)	−0.0143 (8)
O2	0.0686 (10)	0.0477 (9)	0.0462 (8)	0.0004 (8)	0.0111 (7)	0.0086 (7)
Cl1	0.1007 (6)	0.0582 (4)	0.0912 (5)	−0.0164 (4)	0.0558 (4)	−0.0252 (3)
Cl2	0.0720 (4)	0.0775 (4)	0.0574 (4)	0.0006 (3)	0.0258 (3)	−0.0011 (3)
S1	0.0334 (2)	0.0338 (3)	0.0449 (3)	−0.00172 (19)	0.01091 (19)	−0.00076 (19)

C1—C2	1.377 (3)	C8—Cl1	1.723 (3)
C1—C6	1.382 (3)	C9—C10	1.363 (4)
C1—S1	1.7620 (19)	C9—H9	0.9300
C2—C3	1.381 (3)	C10—C11	1.370 (4)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.377 (4)	C11—C12	1.385 (3)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.382 (3)	C12—Cl2	1.733 (2)
C4—C13	1.504 (3)	C13—H13A	0.9600
C5—C6	1.383 (3)	C13—H13B	0.9600
C5—H5	0.9300	C13—H13C	0.9600
C6—H6	0.9300	N1—S1	1.6386 (17)
C7—C12	1.385 (3)	N1—H1N	0.830 (16)
C7—C8	1.396 (3)	O1—S1	1.4283 (14)
C7—N1	1.416 (3)	O2—S1	1.4241 (16)
C8—C9	1.382 (4)
C2—C1—C6	120.64 (19)	C8—C9—H9	119.9
C2—C1—S1	118.80 (16)	C9—C10—C11	120.5 (3)
C6—C1—S1	120.44 (15)	C9—C10—H10	119.8
C1—C2—C3	118.8 (2)	C11—C10—H10	119.8
C1—C2—H2	120.6	C10—C11—C12	119.3 (3)
C3—C2—H2	120.6	C10—C11—H11	120.4
C4—C3—C2	122.0 (2)	C12—C11—H11	120.4
C4—C3—H3	119.0	C7—C12—C11	122.0 (2)
C2—C3—H3	119.0	C7—C12—Cl2	119.81 (17)
C3—C4—C5	117.9 (2)	C11—C12—Cl2	118.2 (2)
C3—C4—C13	120.4 (2)	C4—C13—H13A	109.5
C5—C4—C13	121.6 (3)	C4—C13—H13B	109.5
C4—C5—C6	121.4 (2)	H13A—C13—H13B	109.5
C4—C5—H5	119.3	C4—C13—H13C	109.5
C6—C5—H5	119.3	H13A—C13—H13C	109.5
C1—C6—C5	119.2 (2)	H13B—C13—H13C	109.5
C1—C6—H6	120.4	C7—N1—S1	122.66 (13)
C5—C6—H6	120.4	C7—N1—H1N	118.4 (17)
C12—C7—C8	116.9 (2)	S1—N1—H1N	112.8 (17)
C12—C7—N1	122.35 (18)	O2—S1—O1	119.96 (10)
C8—C7—N1	120.7 (2)	O2—S1—N1	106.35 (9)
C9—C8—C7	121.2 (3)	O1—S1—N1	106.68 (9)
C9—C8—Cl1	118.5 (2)	O2—S1—C1	106.85 (10)
C7—C8—Cl1	120.36 (19)	O1—S1—C1	107.77 (9)
C10—C9—C8	120.1 (3)	N1—S1—C1	108.88 (9)
C10—C9—H9	119.9
C6—C1—C2—C3	0.4 (3)	C8—C7—C12—C11	0.1 (3)
S1—C1—C2—C3	−175.68 (18)	N1—C7—C12—C11	177.3 (2)
C1—C2—C3—C4	0.8 (4)	C8—C7—C12—Cl2	−178.62 (16)
C2—C3—C4—C5	−1.7 (4)	N1—C7—C12—Cl2	−1.4 (3)
C2—C3—C4—C13	177.1 (3)	C10—C11—C12—C7	1.7 (4)
C3—C4—C5—C6	1.5 (4)	C10—C11—C12—Cl2	−179.5 (2)
C13—C4—C5—C6	−177.2 (3)	C12—C7—N1—S1	104.6 (2)
C2—C1—C6—C5	−0.6 (3)	C8—C7—N1—S1	−78.4 (2)
S1—C1—C6—C5	175.45 (18)	C7—N1—S1—O2	154.79 (16)
C4—C5—C6—C1	−0.4 (4)	C7—N1—S1—O1	25.65 (18)
C12—C7—C8—C9	−2.0 (3)	C7—N1—S1—C1	−90.40 (17)
N1—C7—C8—C9	−179.2 (2)	C2—C1—S1—O2	25.70 (19)
C12—C7—C8—Cl1	176.09 (16)	C6—C1—S1—O2	−150.40 (17)
N1—C7—C8—Cl1	−1.1 (3)	C2—C1—S1—O1	155.87 (16)
C7—C8—C9—C10	2.1 (4)	C6—C1—S1—O1	−20.2 (2)
Cl1—C8—C9—C10	−176.0 (2)	C2—C1—S1—N1	−88.79 (17)
C8—C9—C10—C11	−0.2 (5)	C6—C1—S1—N1	95.11 (18)
C9—C10—C11—C12	−1.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.83 (2)	2.16 (2)	2.971 (2)	165 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.83 (2)	2.16 (2)	2.971 (2)	165 (2)

Symmetry code: (i) .