4-Chloro-N-(2-chloro-phen-yl)-2-methyl-benzene-sulfonamide.

In the crystal structure of the title compound, C(13)H(11)Cl(2)NO(2)S, the conformations of the N-C bond in the C-SO(2)-NH-C segment are trans and gauche with respect to the S=O bonds. The C-S(O(2))-N(H)-C torsion angle is 74.8 (4)°, indicating that the mol-ecule is bent at the S atom. In the crystal structure, inversion dimers linked by pairs of N-H⋯O hydrogen bonds occur. An intramolecular N-H⋯Cl inter-action is also present.

Related literature

For related structures of N-(ar­yl)-aryl­sulfonamides, see: Gelbrich et al. (2007 ▶); Gowda et al. (2009 ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C13H11Cl2NO2S

M = 316.19

Triclinic,

a = 8.089 (2) Å

b = 8.096 (2) Å

c = 10.946 (3) Å

α = 96.00 (1)°

β = 97.11 (2)°

γ = 105.67 (2)°

V = 677.7 (3) Å3

Z = 2

Cu Kα radiation

μ = 5.73 mm−1

T = 299 K

0.45 × 0.33 × 0.08 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.150, T max = 0.640

2684 measured reflections

2414 independent reflections

1932 reflections with I > 2σ(I)

R int = 0.037

3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

R[F 2 > 2σ(F 2)] = 0.083

wR(F 2) = 0.236

S = 1.05

2414 reflections

177 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.60 e Å−3

Δρmin = −0.67 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/S1600536809007880/tk2384sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007880/tk2384Isup2.hkl

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

C13H11Cl2NO2S	Z = 2
Mr = 316.19	F(000) = 324
Triclinic, P1	Dx = 1.549 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54180 Å
a = 8.089 (2) Å	Cell parameters from 25 reflections
b = 8.096 (2) Å	θ = 5.7–19.7°
c = 10.946 (3) Å	µ = 5.73 mm−1
α = 96.00 (1)°	T = 299 K
β = 97.11 (2)°	Plate, colourless
γ = 105.67 (2)°	0.45 × 0.33 × 0.08 mm
V = 677.7 (3) Å3

Enraf–Nonius CAD-4 diffractometer	1932 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.037
graphite	θmax = 66.9°, θmin = 4.1°
ω scans	h = −9→1
Absorption correction: ψ scan (North et al., 1968)	k = −9→9
Tmin = 0.150, Tmax = 0.640	l = −12→13
2684 measured reflections	3 standard reflections every 120 min
2414 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)] = 0.083	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.236	w = 1/[σ2(Fo2) + (0.179P)2 + 0.1079P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.008
2414 reflections	Δρmax = 0.60 e Å−3
177 parameters	Δρmin = −0.67 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: 0.039 (6)

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	0.35954 (18)	0.30027 (19)	0.56480 (12)	0.0932 (5)
Cl2	0.70514 (17)	0.48939 (15)	0.15780 (13)	0.0901 (5)
S1	0.71199 (12)	−0.00409 (12)	0.15693 (9)	0.0651 (4)
O1	0.8667 (4)	−0.0424 (4)	0.2054 (3)	0.0761 (8)
O2	0.5732 (4)	−0.1359 (4)	0.0795 (3)	0.0757 (8)
N1	0.7673 (4)	0.1494 (4)	0.0701 (3)	0.0659 (9)
H1N	0.678 (7)	0.178 (6)	0.034 (5)	0.079*
C1	0.6225 (5)	0.0807 (5)	0.2792 (4)	0.0637 (9)
C2	0.7215 (5)	0.1757 (5)	0.3907 (4)	0.0660 (10)
C3	0.6344 (6)	0.2423 (6)	0.4761 (4)	0.0719 (11)
H3	0.6974	0.3069	0.5507	0.086*
C4	0.4585 (6)	0.2158 (6)	0.4536 (4)	0.0708 (10)
C5	0.3607 (6)	0.1217 (6)	0.3426 (4)	0.0732 (11)
H5	0.2410	0.1036	0.3271	0.088*
C6	0.4441 (5)	0.0565 (5)	0.2569 (4)	0.0686 (10)
H6	0.3800	−0.0057	0.1818	0.082*
C7	0.9177 (5)	0.2931 (5)	0.1116 (4)	0.0625 (9)
C8	0.9064 (6)	0.4560 (5)	0.1521 (4)	0.0693 (10)
C9	1.0553 (7)	0.5950 (6)	0.1862 (4)	0.0812 (12)
H9	1.0466	0.7053	0.2114	0.097*
C10	1.2140 (6)	0.5692 (7)	0.1826 (5)	0.0900 (15)
H10	1.3139	0.6619	0.2069	0.108*
C11	1.2280 (6)	0.4087 (7)	0.1436 (5)	0.0900 (15)
H11	1.3372	0.3921	0.1427	0.108*
C12	1.0796 (6)	0.2698 (6)	0.1052 (5)	0.0760 (11)
H12	1.0891	0.1615	0.0753	0.091*
C13	0.9170 (6)	0.2092 (8)	0.4254 (4)	0.0875 (14)
H13A	0.9430	0.1011	0.4307	0.105*
H13B	0.9567	0.2823	0.5044	0.105*
H13C	0.9747	0.2655	0.3630	0.105*

	U11	U22	U33	U12	U13	U23
Cl1	0.0896 (9)	0.1076 (10)	0.0887 (9)	0.0410 (7)	0.0150 (6)	0.0072 (7)
Cl2	0.0869 (8)	0.0730 (8)	0.1186 (10)	0.0325 (6)	0.0255 (7)	0.0141 (6)
S1	0.0608 (6)	0.0547 (6)	0.0758 (7)	0.0165 (4)	−0.0011 (4)	0.0066 (4)
O1	0.0695 (18)	0.0690 (17)	0.093 (2)	0.0285 (14)	0.0023 (15)	0.0136 (14)
O2	0.0690 (17)	0.0601 (16)	0.0872 (19)	0.0119 (13)	−0.0024 (14)	−0.0020 (13)
N1	0.0591 (18)	0.0635 (19)	0.0692 (19)	0.0144 (14)	−0.0032 (14)	0.0074 (14)
C1	0.058 (2)	0.060 (2)	0.073 (2)	0.0185 (16)	−0.0008 (17)	0.0152 (17)
C2	0.061 (2)	0.071 (2)	0.065 (2)	0.0205 (17)	−0.0021 (17)	0.0108 (17)
C3	0.072 (2)	0.073 (2)	0.065 (2)	0.0210 (19)	−0.0043 (18)	0.0072 (18)
C4	0.075 (2)	0.070 (2)	0.071 (2)	0.0278 (19)	0.0071 (19)	0.0153 (18)
C5	0.062 (2)	0.079 (3)	0.079 (3)	0.0260 (19)	0.0022 (19)	0.013 (2)
C6	0.061 (2)	0.067 (2)	0.072 (2)	0.0168 (18)	−0.0026 (18)	0.0084 (17)
C7	0.058 (2)	0.062 (2)	0.063 (2)	0.0149 (16)	−0.0013 (15)	0.0093 (15)
C8	0.072 (2)	0.065 (2)	0.068 (2)	0.0178 (18)	0.0016 (18)	0.0123 (17)
C9	0.087 (3)	0.067 (2)	0.077 (3)	0.006 (2)	0.000 (2)	0.0105 (19)
C10	0.070 (3)	0.086 (3)	0.095 (3)	−0.005 (2)	−0.011 (2)	0.025 (2)
C11	0.061 (2)	0.094 (3)	0.109 (4)	0.014 (2)	−0.005 (2)	0.032 (3)
C12	0.062 (2)	0.080 (3)	0.089 (3)	0.023 (2)	0.008 (2)	0.022 (2)
C13	0.062 (3)	0.114 (4)	0.075 (3)	0.022 (2)	−0.008 (2)	−0.003 (2)

Cl1—C4	1.719 (5)	C5—H5	0.9300
Cl2—C8	1.728 (5)	C6—H6	0.9300
S1—O1	1.423 (3)	C7—C8	1.378 (6)
S1—O2	1.430 (3)	C7—C12	1.381 (6)
S1—N1	1.643 (4)	C8—C9	1.388 (6)
S1—C1	1.761 (4)	C9—C10	1.360 (8)
N1—C7	1.424 (5)	C9—H9	0.9300
N1—H1N	0.88 (5)	C10—C11	1.364 (8)
C1—C6	1.390 (5)	C10—H10	0.9300
C1—C2	1.398 (5)	C11—C12	1.389 (6)
C2—C3	1.387 (7)	C11—H11	0.9300
C2—C13	1.522 (6)	C12—H12	0.9300
C3—C4	1.366 (6)	C13—H13A	0.9600
C3—H3	0.9300	C13—H13B	0.9600
C4—C5	1.388 (6)	C13—H13C	0.9600
C5—C6	1.364 (7)
O1—S1—O2	120.08 (19)	C1—C6—H6	119.2
O1—S1—N1	107.27 (18)	C8—C7—C12	119.1 (4)
O2—S1—N1	104.75 (18)	C8—C7—N1	122.1 (4)
O1—S1—C1	109.99 (19)	C12—C7—N1	118.8 (4)
O2—S1—C1	106.96 (19)	C7—C8—C9	120.6 (4)
N1—S1—C1	107.03 (18)	C7—C8—Cl2	120.0 (3)
C7—N1—S1	120.4 (3)	C9—C8—Cl2	119.4 (4)
C7—N1—H1N	114 (3)	C10—C9—C8	119.6 (5)
S1—N1—H1N	113 (3)	C10—C9—H9	120.2
C6—C1—C2	120.1 (4)	C8—C9—H9	120.2
C6—C1—S1	116.1 (3)	C9—C10—C11	120.6 (4)
C2—C1—S1	123.7 (3)	C9—C10—H10	119.7
C3—C2—C1	117.4 (4)	C11—C10—H10	119.7
C3—C2—C13	118.0 (4)	C10—C11—C12	120.2 (5)
C1—C2—C13	124.6 (4)	C10—C11—H11	119.9
C4—C3—C2	121.9 (4)	C12—C11—H11	119.9
C4—C3—H3	119.0	C7—C12—C11	119.8 (5)
C2—C3—H3	119.0	C7—C12—H12	120.1
C3—C4—C5	120.6 (4)	C11—C12—H12	120.1
C3—C4—Cl1	119.2 (4)	C2—C13—H13A	109.5
C5—C4—Cl1	120.3 (4)	C2—C13—H13B	109.5
C6—C5—C4	118.5 (4)	H13A—C13—H13B	109.5
C6—C5—H5	120.8	C2—C13—H13C	109.5
C4—C5—H5	120.8	H13A—C13—H13C	109.5
C5—C6—C1	121.6 (4)	H13B—C13—H13C	109.5
C5—C6—H6	119.2
O1—S1—N1—C7	−43.2 (4)	Cl1—C4—C5—C6	−179.9 (3)
O2—S1—N1—C7	−171.9 (3)	C4—C5—C6—C1	0.7 (6)
C1—S1—N1—C7	74.8 (4)	C2—C1—C6—C5	−0.9 (6)
O1—S1—C1—C6	−153.8 (3)	S1—C1—C6—C5	−177.6 (3)
O2—S1—C1—C6	−21.8 (3)	S1—N1—C7—C8	−106.8 (4)
N1—S1—C1—C6	90.0 (3)	S1—N1—C7—C12	76.4 (5)
O1—S1—C1—C2	29.7 (4)	C12—C7—C8—C9	−0.1 (6)
O2—S1—C1—C2	161.6 (3)	N1—C7—C8—C9	−176.9 (4)
N1—S1—C1—C2	−86.6 (4)	C12—C7—C8—Cl2	178.6 (3)
C6—C1—C2—C3	0.2 (6)	N1—C7—C8—Cl2	1.9 (6)
S1—C1—C2—C3	176.7 (3)	C7—C8—C9—C10	−1.7 (7)
C6—C1—C2—C13	179.5 (4)	Cl2—C8—C9—C10	179.6 (4)
S1—C1—C2—C13	−4.0 (6)	C8—C9—C10—C11	1.2 (8)
C1—C2—C3—C4	0.6 (6)	C9—C10—C11—C12	1.0 (8)
C13—C2—C3—C4	−178.8 (4)	C8—C7—C12—C11	2.3 (6)
C2—C3—C4—C5	−0.7 (7)	N1—C7—C12—C11	179.2 (4)
C2—C3—C4—Cl1	179.2 (3)	C10—C11—C12—C7	−2.7 (7)
C3—C4—C5—C6	0.1 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.88 (5)	2.17 (5)	2.994 (5)	157 (4)
N1—H1N···Cl2	0.88 (5)	2.67 (5)	3.011 (4)	104 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.88 (5)	2.17 (5)	2.994 (5)	157 (4)
N1—H1N⋯Cl2	0.88 (5)	2.67 (5)	3.011 (4)	104 (4)

Symmetry code: (i) .