4-Methyl-N-(4-methyl-phenyl-sulfon-yl)-N-phenyl-benzene-sulfonamide.

The whole mol-ecule of the title compound, C20H19NO4S2, is generated by twofold rotational symmetry. The N atom is located on the twofold rotation axis and has a trigonal-planar geometry. It is bonded by two S atoms of two symmetry-related 4-methyl-phenyl-sulfonyl groups and by the C atom of the phenyl ring, which is bis-ected by the twofold rotation axis. The benzene and phenyl rings are oriented at a dihedral angle of 51.48 (5)° while the pendant benzene rings are inclined to one another by 87.76 (9)°. In the crystal, weak C-H⋯O hydrogen bonds link the mol-ecules, forming a three-dimensional network.

Related literature

Several sulfonamide derivatives have been used as chemotherapeutic agents for their anti­bacterial, anti­fungal, anti­tumor and hypoglycemic effects for many years, see: Chohan et al. (2010 ▶); El-Sayed et al. (2011 ▶); Seri et al. (2000 ▶). Some sulfonamide derivatives are reported to have carbonic anhydrases (CA) inhibition properties, see: Suparan et al. (2000 ▶). For the use of disulfonamides for their anti­tumor activity and CA inhibitory properties, see: Boriack-Sjodin et al. (1998 ▶). For the use as catalysts in asymmetric syntheses of complexes obtained from disulfonamides chiral derivatives, see: Guo et al. (1997 ▶). For sulfonation of aniline by 4-tolyl­sulfonyl chloride utilizing standard procedures with small modifications, see: DeChristopher et al. (1974 ▶). For a related structure involving 4-methyl­phenyl­sulfonyl, see: Elgemeie et al. (2013 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C20H19NO4S2

M = 401.51

Monoclinic,

a = 18.1080 (5) Å

b = 9.3834 (3) Å

c = 11.4821 (4) Å

β = 96.015 (3)°

V = 1940.24 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 296 K

0.25 × 0.22 × 0.14 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

9411 measured reflections

2441 independent reflections

1981 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.109

S = 1.05

2441 reflections

125 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.39 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814002086/su2692sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814002086/su2692Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814002086/su2692Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C20H19NO4S2	F(000) = 840
Mr = 401.51	Dx = 1.375 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3887 reflections
a = 18.1080 (5) Å	θ = 2.3–28.1°
b = 9.3834 (3) Å	µ = 0.30 mm−1
c = 11.4821 (4) Å	T = 296 K
β = 96.015 (3)°	Block, colourless
V = 1940.24 (11) Å3	0.25 × 0.22 × 0.14 mm
Z = 4

Bruker Kappa APEXII CCD area-detector diffractometer	1981 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
Graphite monochromator	θmax = 28.4°, θmin = 2.3°
φ and ω scans	h = −24→23
9411 measured reflections	k = −10→12
2441 independent reflections	l = −15→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) = 0.109	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0574P)2 + 0.990P] where P = (Fo2 + 2Fc2)/3
2441 reflections	(Δ/σ)max < 0.001
125 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

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 > 2sigma(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
S1	0.06888 (2)	0.13028 (4)	0.33345 (3)	0.03537 (14)
O1	0.08971 (7)	0.22464 (13)	0.42817 (10)	0.0471 (3)
O2	0.04424 (7)	−0.00962 (13)	0.35650 (11)	0.0491 (3)
N1	0.0000	0.21329 (18)	0.2500	0.0332 (4)
C1	0.14280 (9)	0.12114 (17)	0.24640 (14)	0.0369 (3)
C2	0.20477 (10)	0.2045 (2)	0.27464 (17)	0.0533 (5)
H2	0.2065	0.2682	0.3369	0.064*
C3	0.26449 (11)	0.1920 (2)	0.2089 (2)	0.0622 (5)
H3	0.3066	0.2472	0.2284	0.075*
C4	0.26270 (10)	0.0998 (2)	0.11573 (17)	0.0502 (4)
C5	0.19959 (10)	0.0185 (2)	0.08876 (17)	0.0555 (5)
H5	0.1976	−0.0443	0.0258	0.067*
C6	0.13953 (10)	0.0282 (2)	0.15261 (17)	0.0505 (4)
H6	0.0974	−0.0270	0.1330	0.061*
C7	0.0000	0.3675 (2)	0.2500	0.0303 (4)
C8	0.03282 (9)	0.43935 (18)	0.16443 (14)	0.0416 (4)
H8	0.0547	0.3897	0.1069	0.050*
C9	0.03269 (12)	0.5865 (2)	0.16553 (18)	0.0575 (5)
H9	0.0549	0.6366	0.1086	0.069*
C10	0.0000	0.6588 (3)	0.2500	0.0642 (8)
H10	0.0000	0.7579	0.2500	0.077*
C11	0.32811 (12)	0.0864 (3)	0.0452 (2)	0.0711 (6)
H11A	0.3110	0.0578	−0.0333	0.107*
H11B	0.3620	0.0163	0.0805	0.107*
H11C	0.3529	0.1767	0.0435	0.107*

	U11	U22	U33	U12	U13	U23
S1	0.0368 (2)	0.0329 (2)	0.0360 (2)	0.00350 (15)	0.00149 (15)	0.00050 (14)
O1	0.0507 (7)	0.0514 (7)	0.0377 (6)	0.0076 (6)	−0.0026 (5)	−0.0083 (5)
O2	0.0542 (7)	0.0365 (7)	0.0565 (7)	0.0010 (5)	0.0051 (6)	0.0118 (5)
N1	0.0307 (9)	0.0270 (9)	0.0416 (9)	0.000	0.0019 (7)	0.000
C1	0.0326 (7)	0.0355 (8)	0.0421 (8)	0.0054 (6)	0.0014 (6)	−0.0017 (6)
C2	0.0428 (10)	0.0543 (12)	0.0634 (11)	−0.0051 (8)	0.0085 (8)	−0.0180 (9)
C3	0.0400 (10)	0.0637 (14)	0.0836 (14)	−0.0079 (9)	0.0102 (9)	−0.0130 (11)
C4	0.0383 (9)	0.0586 (11)	0.0542 (10)	0.0136 (8)	0.0077 (8)	0.0061 (9)
C5	0.0433 (10)	0.0721 (13)	0.0507 (10)	0.0088 (9)	0.0036 (8)	−0.0189 (9)
C6	0.0373 (9)	0.0587 (11)	0.0551 (10)	0.0005 (8)	0.0023 (7)	−0.0181 (9)
C7	0.0289 (9)	0.0271 (10)	0.0353 (10)	0.000	0.0052 (8)	0.000
C8	0.0416 (9)	0.0435 (10)	0.0412 (8)	−0.0051 (7)	0.0116 (7)	0.0032 (7)
C9	0.0655 (13)	0.0455 (11)	0.0606 (11)	−0.0167 (10)	0.0013 (9)	0.0166 (9)
C10	0.076 (2)	0.0270 (13)	0.084 (2)	0.000	−0.0178 (17)	0.000
C11	0.0481 (11)	0.0943 (18)	0.0736 (14)	0.0158 (12)	0.0198 (10)	0.0051 (13)

S1—O1	1.4223 (12)	C6—C5	1.377 (3)
S1—O2	1.4203 (13)	C6—H6	0.9300
S1—N1	1.6822 (9)	C7—N1	1.447 (3)
S1—C1	1.7546 (17)	C7—C8i	1.3768 (18)
N1—S1i	1.6822 (9)	C7—C8	1.3768 (18)
C1—C2	1.378 (2)	C8—C9	1.380 (3)
C1—C6	1.382 (2)	C8—H8	0.9300
C2—C3	1.387 (3)	C9—C10	1.368 (3)
C2—H2	0.9300	C9—H9	0.9300
C3—H3	0.9300	C10—C9i	1.368 (3)
C4—C3	1.374 (3)	C10—H10	0.9300
C4—C5	1.382 (3)	C11—H11A	0.9600
C4—C11	1.508 (3)	C11—H11B	0.9600
C5—H5	0.9300	C11—H11C	0.9600
O1—S1—N1	105.59 (7)	C6—C5—H5	119.2
O1—S1—C1	108.00 (8)	C1—C6—H6	120.5
O2—S1—O1	119.74 (8)	C5—C6—C1	118.97 (17)
O2—S1—N1	107.79 (8)	C5—C6—H6	120.5
O2—S1—C1	109.53 (8)	C8i—C7—N1	119.33 (10)
N1—S1—C1	105.22 (5)	C8—C7—N1	119.33 (10)
S1i—N1—S1	124.83 (11)	C8i—C7—C8	121.3 (2)
C7—N1—S1	117.58 (5)	C7—C8—C9	118.82 (17)
C7—N1—S1i	117.58 (5)	C7—C8—H8	120.6
C2—C1—S1	119.29 (13)	C9—C8—H8	120.6
C2—C1—C6	120.59 (16)	C8—C9—H9	119.9
C6—C1—S1	120.10 (13)	C10—C9—C8	120.26 (19)
C1—C2—C3	119.09 (17)	C10—C9—H9	119.9
C1—C2—H2	120.5	C9i—C10—C9	120.5 (3)
C3—C2—H2	120.5	C9i—C10—H10	119.8
C2—C3—H3	119.3	C9—C10—H10	119.8
C4—C3—C2	121.38 (18)	C4—C11—H11A	109.5
C4—C3—H3	119.3	C4—C11—H11B	109.5
C3—C4—C5	118.27 (17)	C4—C11—H11C	109.5
C3—C4—C11	120.97 (19)	H11A—C11—H11B	109.5
C5—C4—C11	120.76 (19)	H11A—C11—H11C	109.5
C4—C5—H5	119.2	H11B—C11—H11C	109.5
C6—C5—C4	121.70 (17)
O1—S1—N1—S1i	−151.02 (6)	C2—C1—C6—C5	0.9 (3)
O1—S1—N1—C7	28.98 (6)	C1—C2—C3—C4	0.8 (3)
O2—S1—N1—S1i	−21.94 (6)	C5—C4—C3—C2	−0.2 (3)
O2—S1—N1—C7	158.06 (6)	C11—C4—C3—C2	−179.7 (2)
C1—S1—N1—S1i	94.88 (6)	C3—C4—C5—C6	−0.1 (3)
C1—S1—N1—C7	−85.12 (6)	C11—C4—C5—C6	179.42 (19)
O1—S1—C1—C2	−3.00 (17)	C1—C6—C5—C4	−0.3 (3)
O1—S1—C1—C6	175.15 (14)	C8—C7—N1—S1	94.21 (8)
O2—S1—C1—C2	−134.97 (15)	C8i—C7—N1—S1	−85.79 (8)
O2—S1—C1—C6	43.18 (16)	C8—C7—N1—S1i	−85.79 (8)
N1—S1—C1—C2	109.41 (15)	C8i—C7—N1—S1i	94.21 (8)
N1—S1—C1—C6	−72.44 (16)	N1—C7—C8—C9	−179.79 (12)
S1—C1—C2—C3	177.00 (16)	C8i—C7—C8—C9	0.21 (12)
C6—C1—C2—C3	−1.1 (3)	C7—C8—C9—C10	−0.4 (2)
S1—C1—C6—C5	−177.22 (15)	C8—C9—C10—C9i	0.21 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2i	0.93	2.59	3.337 (2)	138
C9—H9···O1ii	0.93	2.58	3.496 (2)	168
C10—H10···O2iii	0.93	2.59	3.408 (3)	147
C10—H10···O2iv	0.93	2.59	3.408 (3)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2i	0.93	2.59	3.337 (2)	138
C9—H9⋯O1ii	0.93	2.58	3.496 (2)	168
C10—H10⋯O2iii	0.93	2.59	3.408 (3)	147
C10—H10⋯O2iv	0.93	2.59	3.408 (3)	147

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .