N,N'-[1,3-Phenylenebis(methyl-ene)]dibenzene-sulfonamide.

The complete mol-ecule of the title compound, C(20)H(20)N(2)O(4)S(2), is generated by crystallographic twofold symmetry, with two C atoms lying on the rotation axis. The dihedral angle between the central benzene ring and the pendant ring is 68.42 (6)° and the dihedral angle between the pendant rings is 45.11 (5)°. The torsion angles for the C-S-N-C and S-N-C-C fragments are -73.22 (15) and -150.45 (13)°, respectively. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, generating corrugated (001) sheets. Aromatic π-π stacking [centroid-centroid separation = 3.8925 (12) and 3.9777 (12) Å] and weak C-H⋯O inter-actions also occur.

Related literature

For a related structure, see: Khan et al. (2011 ▶).

Experimental

Crystal data

C20H20N2O4S2

M = 416.50

Monoclinic,

a = 16.4319 (6) Å

b = 7.8024 (3) Å

c = 16.1217 (6) Å

β = 111.543 (2)°

V = 1922.54 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 296 K

0.15 × 0.11 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

8653 measured reflections

2346 independent reflections

1841 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.103

S = 1.07

2346 reflections

131 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.34 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 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811040694/su2323sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811040694/su2323Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811040694/su2323Isup3.cml

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

C20H20N2O4S2	F(000) = 872
Mr = 416.50	Dx = 1.439 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2346 reflections
a = 16.4319 (6) Å	θ = 2.9–28.3°
b = 7.8024 (3) Å	µ = 0.31 mm−1
c = 16.1217 (6) Å	T = 296 K
β = 111.543 (2)°	Block, colourless
V = 1922.54 (12) Å3	0.15 × 0.11 × 0.08 mm
Z = 4

Bruker APEXII CCD diffractometer	1841 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
graphite	θmax = 28.3°, θmin = 2.9°
ω scans	h = −21→21
8653 measured reflections	k = −9→10
2346 independent reflections	l = −21→21

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) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0466P)2 + 1.1784P] where P = (Fo2 + 2Fc2)/3
2346 reflections	(Δ/σ)max = 0.001
131 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

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	0.23478 (13)	0.4749 (3)	0.57485 (13)	0.0492 (5)
H1A	0.2133	0.4616	0.6204	0.059*
C2	0.18163 (12)	0.5397 (3)	0.49388 (14)	0.0493 (5)
H2	0.1239	0.5677	0.4846	0.059*
C3	0.21285 (11)	0.5637 (3)	0.42623 (12)	0.0405 (4)
H3	0.1766	0.6069	0.3713	0.049*
C4	0.29908 (10)	0.5225 (2)	0.44139 (10)	0.0313 (4)
C5	0.35276 (12)	0.4531 (2)	0.52240 (11)	0.0396 (4)
H5	0.4102	0.4230	0.5318	0.048*
C6	0.31953 (13)	0.4296 (3)	0.58870 (12)	0.0481 (5)
H6	0.3548	0.3828	0.6431	0.058*
C7	0.43547 (11)	0.2757 (2)	0.36899 (11)	0.0378 (4)
H7A	0.4162	0.1957	0.4041	0.045*
H7B	0.4827	0.3439	0.4096	0.045*
C8	0.46828 (10)	0.1780 (2)	0.30692 (11)	0.0332 (4)
C9	0.5000	0.2653 (3)	0.2500	0.0320 (5)
H9	0.5000	0.3845	0.2500	0.038*
C10	0.46821 (12)	0.0009 (3)	0.30605 (13)	0.0429 (4)
H10	0.4467	−0.0593	0.3434	0.052*
C11	0.5000	−0.0871 (4)	0.2500	0.0504 (7)
H11	0.5000	−0.2063	0.2500	0.061*
S1	0.34361 (3)	0.56500 (6)	0.35953 (3)	0.03403 (15)
N1	0.36255 (9)	0.3882 (2)	0.31843 (10)	0.0382 (4)
H1	0.3187 (13)	0.339 (3)	0.2865 (14)	0.046*
O1	0.42667 (8)	0.64544 (18)	0.40359 (9)	0.0459 (3)
O2	0.27803 (9)	0.65172 (19)	0.28749 (8)	0.0502 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0510 (11)	0.0624 (14)	0.0390 (10)	−0.0120 (10)	0.0223 (9)	−0.0015 (9)
C2	0.0371 (10)	0.0647 (14)	0.0507 (11)	−0.0021 (9)	0.0213 (9)	−0.0029 (10)
C3	0.0355 (9)	0.0490 (12)	0.0342 (9)	0.0017 (8)	0.0097 (7)	0.0017 (8)
C4	0.0330 (8)	0.0318 (9)	0.0282 (7)	−0.0021 (6)	0.0101 (6)	−0.0021 (6)
C5	0.0362 (9)	0.0459 (11)	0.0343 (8)	0.0004 (7)	0.0101 (7)	0.0019 (7)
C6	0.0526 (11)	0.0575 (13)	0.0307 (9)	−0.0038 (9)	0.0110 (8)	0.0074 (8)
C7	0.0364 (9)	0.0416 (11)	0.0367 (9)	0.0013 (7)	0.0151 (7)	0.0044 (8)
C8	0.0264 (7)	0.0335 (10)	0.0379 (8)	−0.0002 (6)	0.0098 (7)	0.0026 (7)
C9	0.0316 (11)	0.0233 (12)	0.0409 (12)	0.000	0.0131 (10)	0.000
C10	0.0406 (9)	0.0337 (10)	0.0530 (11)	−0.0052 (8)	0.0155 (9)	0.0091 (9)
C11	0.0536 (16)	0.0234 (14)	0.0696 (19)	0.000	0.0171 (15)	0.000
S1	0.0348 (2)	0.0367 (3)	0.0307 (2)	0.00170 (17)	0.01223 (17)	0.00359 (17)
N1	0.0313 (7)	0.0452 (10)	0.0358 (8)	0.0011 (6)	0.0095 (6)	−0.0079 (7)
O1	0.0439 (7)	0.0438 (8)	0.0516 (7)	−0.0117 (6)	0.0195 (6)	0.0002 (6)
O2	0.0544 (8)	0.0605 (10)	0.0357 (7)	0.0195 (7)	0.0165 (6)	0.0149 (6)

C1—C2	1.373 (3)	C7—H7A	0.9700
C1—C6	1.373 (3)	C7—H7B	0.9700
C1—H1A	0.9300	C8—C10	1.382 (3)
C2—C3	1.378 (3)	C8—C9	1.389 (2)
C2—H2	0.9300	C9—C8i	1.389 (2)
C3—C4	1.385 (2)	C9—H9	0.9300
C3—H3	0.9300	C10—C11	1.381 (2)
C4—C5	1.390 (2)	C10—H10	0.9300
C4—S1	1.7596 (17)	C11—C10i	1.381 (2)
C5—C6	1.379 (3)	C11—H11	0.9300
C5—H5	0.9300	S1—O2	1.4314 (12)
C6—H6	0.9300	S1—O1	1.4315 (13)
C7—N1	1.467 (2)	S1—N1	1.6092 (16)
C7—C8	1.506 (2)	N1—H1	0.81 (2)
C2—C1—C6	120.16 (18)	H7A—C7—H7B	108.1
C2—C1—H1A	119.9	C10—C8—C9	118.86 (17)
C6—C1—H1A	119.9	C10—C8—C7	120.91 (16)
C1—C2—C3	120.73 (18)	C9—C8—C7	120.22 (17)
C1—C2—H2	119.6	C8i—C9—C8	121.3 (2)
C3—C2—H2	119.6	C8i—C9—H9	119.4
C2—C3—C4	118.88 (16)	C8—C9—H9	119.4
C2—C3—H3	120.6	C11—C10—C8	120.31 (19)
C4—C3—H3	120.6	C11—C10—H10	119.8
C3—C4—C5	120.78 (16)	C8—C10—H10	119.8
C3—C4—S1	120.29 (13)	C10—C11—C10i	120.4 (3)
C5—C4—S1	118.89 (13)	C10—C11—H11	119.8
C6—C5—C4	119.00 (17)	C10i—C11—H11	119.8
C6—C5—H5	120.5	O2—S1—O1	119.47 (9)
C4—C5—H5	120.5	O2—S1—N1	105.84 (8)
C1—C6—C5	120.41 (17)	O1—S1—N1	106.67 (8)
C1—C6—H6	119.8	O2—S1—C4	107.53 (8)
C5—C6—H6	119.8	O1—S1—C4	107.08 (8)
N1—C7—C8	110.62 (13)	N1—S1—C4	110.10 (8)
N1—C7—H7A	109.5	C7—N1—S1	121.73 (12)
C8—C7—H7A	109.5	C7—N1—H1	114.8 (15)
N1—C7—H7B	109.5	S1—N1—H1	114.1 (15)
C8—C7—H7B	109.5
C6—C1—C2—C3	−1.4 (3)	C7—C8—C10—C11	−178.78 (13)
C1—C2—C3—C4	−0.4 (3)	C8—C10—C11—C10i	−0.31 (11)
C2—C3—C4—C5	1.9 (3)	C3—C4—S1—O2	3.65 (17)
C2—C3—C4—S1	−175.61 (15)	C5—C4—S1—O2	−173.94 (14)
C3—C4—C5—C6	−1.6 (3)	C3—C4—S1—O1	133.19 (15)
S1—C4—C5—C6	175.99 (15)	C5—C4—S1—O1	−44.39 (17)
C2—C1—C6—C5	1.8 (3)	C3—C4—S1—N1	−111.21 (15)
C4—C5—C6—C1	−0.3 (3)	C5—C4—S1—N1	71.20 (16)
N1—C7—C8—C10	−121.05 (17)	C8—C7—N1—S1	−150.45 (13)
N1—C7—C8—C9	59.57 (18)	O2—S1—N1—C7	170.85 (14)
C10—C8—C9—C8i	−0.30 (11)	O1—S1—N1—C7	42.63 (16)
C7—C8—C9—C8i	179.09 (15)	C4—S1—N1—C7	−73.22 (15)
C9—C8—C10—C11	0.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ii	0.81 (2)	2.16 (2)	2.960 (2)	166 (2)
C5—H5···O1iii	0.93	2.55	3.461 (2)	166
C10—H10···O1iv	0.93	2.57	3.379 (3)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.81 (2)	2.16 (2)	2.960 (2)	166 (2)
C5—H5⋯O1ii	0.93	2.55	3.461 (2)	166
C10—H10⋯O1iii	0.93	2.57	3.379 (3)	146

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