N,N'-[1,3-Phenyl-enebis(methyl-ene)]di-p-toluenesulfonamide.

In the title compound, C(22)H(24)N(2)O(4)S(2), the dihedral angles between the central benzene ring and the pendant rings are 66.96 (13) and 69.37 (13)°. The torsion angles for the C-N-S-C fragments are -68.5 (3) and -72.6 (3)°. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds to generate infinite (001) sheets containing R(4) (4)(28) loops. A weak aromatic π-π stacking contact between one of the terminal benzene rings and its inversion-related partner is also observed [centroid-to-centroid separation = 3.796 (2) Å and slippage = 1.581 Å], as are two possible C-H⋯π contacts.

Related literature

For a related structure, see: Ejaz et al. (2011 ▶). For hydrogen-bonding motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C22H24N2O4S2

M = 444.55

Triclinic,

a = 7.7562 (3) Å

b = 8.7905 (3) Å

c = 17.1479 (5) Å

α = 87.554 (1)°

β = 86.151 (1)°

γ = 70.895 (1)°

V = 1102.00 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.27 mm−1

T = 296 K

0.30 × 0.20 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

19493 measured reflections

5417 independent reflections

3937 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.187

S = 1.13

5417 reflections

273 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.41 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/S1600536812007222/su2379sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007222/su2379Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812007222/su2379Isup3.cml

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

C22H24N2O4S2	Z = 2
Mr = 444.55	F(000) = 468
Triclinic, P1	Dx = 1.340 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7562 (3) Å	Cell parameters from 6272 reflections
b = 8.7905 (3) Å	θ = 2.7–27.1°
c = 17.1479 (5) Å	µ = 0.27 mm−1
α = 87.554 (1)°	T = 296 K
β = 86.151 (1)°	Chip, colourless
γ = 70.895 (1)°	0.30 × 0.20 × 0.15 mm
V = 1102.00 (7) Å3

Bruker APEXII CCD diffractometer	3937 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
Graphite monochromator	θmax = 28.4°, θmin = 2.7°
ω scans	h = −10→6
19493 measured reflections	k = −11→9
5417 independent reflections	l = −22→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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.187	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.0628P)2 + 1.4755P] where P = (Fo2 + 2Fc2)/3
5417 reflections	(Δ/σ)max = 0.002
273 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.41 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	0.2038 (4)	0.8090 (4)	0.09032 (18)	0.0368 (7)
C2	0.2158 (5)	0.8022 (4)	0.0097 (2)	0.0428 (7)
H2A	0.2057	0.7136	−0.0150	0.051*
C3	0.2430 (5)	0.9293 (4)	−0.0337 (2)	0.0480 (8)
H3	0.2527	0.9247	−0.0880	0.058*
C4	0.2561 (4)	1.0631 (4)	0.0017 (2)	0.0458 (8)
C5	0.2419 (5)	1.0681 (4)	0.0823 (2)	0.0522 (9)
H5	0.2502	1.1573	0.1070	0.063*
C6	0.2152 (5)	0.9410 (4)	0.1267 (2)	0.0467 (8)
H6	0.2050	0.9454	0.1809	0.056*
C7	0.2849 (6)	1.2011 (5)	−0.0458 (3)	0.0642 (11)
H7A	0.4002	1.2116	−0.0348	0.096*
H7B	0.1884	1.2987	−0.0326	0.096*
H7C	0.2846	1.1814	−0.1004	0.096*
C8	0.5167 (5)	0.4630 (4)	0.1421 (2)	0.0448 (8)
H8A	0.5583	0.5366	0.1081	0.054*
H8B	0.4842	0.3902	0.1095	0.054*
C9	0.6684 (4)	0.3680 (4)	0.19293 (19)	0.0376 (7)
C10	0.8289 (5)	0.4027 (4)	0.1920 (2)	0.0486 (9)
H10	0.8447	0.4853	0.1597	0.058*
C11	0.9671 (5)	0.3151 (5)	0.2390 (2)	0.0545 (9)
H11	1.0748	0.3402	0.2386	0.065*
C12	0.9465 (5)	0.1917 (4)	0.2862 (2)	0.0471 (8)
H12	1.0406	0.1322	0.3171	0.057*
C13	0.7851 (5)	0.1558 (4)	0.2878 (2)	0.0407 (7)
C14	0.6483 (4)	0.2438 (4)	0.24124 (19)	0.0395 (7)
H14	0.5401	0.2195	0.2421	0.047*
C15	0.7604 (6)	0.0222 (5)	0.3412 (2)	0.0546 (10)
H15A	0.8756	−0.0365	0.3637	0.066*
H15B	0.6719	0.0684	0.3836	0.066*
C16	0.6242 (4)	−0.2929 (4)	0.41314 (19)	0.0391 (7)
C17	0.6438 (5)	−0.2385 (4)	0.4858 (2)	0.0509 (9)
H17	0.6070	−0.1286	0.4947	0.061*
C18	0.7171 (6)	−0.3463 (5)	0.5445 (2)	0.0563 (10)
H18	0.7304	−0.3086	0.5928	0.068*
C19	0.7714 (5)	−0.5093 (5)	0.5330 (2)	0.0514 (9)
C20	0.7504 (6)	−0.5623 (4)	0.4604 (2)	0.0569 (10)
H20	0.7865	−0.6723	0.4518	0.068*
C21	0.6772 (6)	−0.4554 (4)	0.4005 (2)	0.0506 (9)
H21	0.6640	−0.4930	0.3522	0.061*
C22	0.8531 (6)	−0.6281 (6)	0.5971 (3)	0.0731 (13)
H22A	0.9644	−0.6136	0.6113	0.110*
H22B	0.8789	−0.7357	0.5791	0.110*
H22C	0.7683	−0.6109	0.6419	0.110*
S1	0.16991 (10)	0.64814 (10)	0.14733 (5)	0.0395 (2)
S2	0.53793 (12)	−0.15372 (10)	0.33690 (5)	0.0422 (2)
N1	0.3566 (4)	0.5539 (3)	0.19015 (16)	0.0391 (6)
H1	0.3810	0.6124	0.2295	0.047*
N2	0.6978 (4)	−0.0890 (3)	0.29893 (18)	0.0478 (7)
H2	0.7907	−0.1623	0.2698	0.057*
O1	0.1399 (4)	0.5365 (3)	0.09599 (16)	0.0537 (6)
O2	0.0363 (3)	0.7163 (3)	0.20915 (15)	0.0567 (7)
O3	0.3995 (4)	−0.0193 (3)	0.37070 (17)	0.0614 (7)
O4	0.4957 (4)	−0.2391 (3)	0.27635 (16)	0.0632 (8)

	U11	U22	U33	U12	U13	U23
C1	0.0298 (14)	0.0401 (17)	0.0370 (17)	−0.0068 (12)	−0.0034 (12)	0.0024 (13)
C2	0.0409 (17)	0.0444 (18)	0.0405 (18)	−0.0102 (14)	−0.0028 (14)	−0.0021 (15)
C3	0.0451 (19)	0.057 (2)	0.0354 (18)	−0.0097 (16)	−0.0012 (14)	0.0059 (16)
C4	0.0320 (16)	0.0459 (19)	0.054 (2)	−0.0058 (14)	−0.0060 (14)	0.0135 (16)
C5	0.058 (2)	0.0424 (19)	0.057 (2)	−0.0172 (17)	−0.0097 (18)	0.0017 (17)
C6	0.055 (2)	0.0461 (19)	0.0384 (18)	−0.0157 (16)	−0.0055 (15)	0.0016 (15)
C7	0.050 (2)	0.063 (3)	0.078 (3)	−0.0178 (19)	−0.012 (2)	0.028 (2)
C8	0.0429 (18)	0.0429 (18)	0.0425 (19)	−0.0073 (15)	−0.0009 (14)	0.0094 (15)
C9	0.0357 (15)	0.0313 (15)	0.0422 (17)	−0.0069 (12)	0.0005 (13)	0.0028 (13)
C10	0.0463 (19)	0.0418 (18)	0.060 (2)	−0.0200 (15)	0.0047 (16)	0.0113 (16)
C11	0.0389 (18)	0.058 (2)	0.072 (3)	−0.0240 (17)	−0.0011 (17)	0.0060 (19)
C12	0.0354 (16)	0.0439 (19)	0.059 (2)	−0.0074 (14)	−0.0092 (15)	0.0027 (16)
C13	0.0445 (17)	0.0323 (16)	0.0450 (18)	−0.0124 (13)	−0.0045 (14)	0.0063 (14)
C14	0.0376 (16)	0.0388 (17)	0.0450 (18)	−0.0168 (13)	−0.0029 (13)	0.0042 (14)
C15	0.071 (3)	0.049 (2)	0.051 (2)	−0.0285 (19)	−0.0196 (19)	0.0165 (17)
C16	0.0377 (16)	0.0363 (16)	0.0417 (18)	−0.0101 (13)	−0.0017 (13)	0.0024 (14)
C17	0.061 (2)	0.0413 (19)	0.043 (2)	−0.0053 (16)	−0.0046 (16)	−0.0032 (15)
C18	0.066 (2)	0.063 (2)	0.0352 (19)	−0.015 (2)	−0.0035 (17)	−0.0012 (17)
C19	0.0461 (19)	0.055 (2)	0.047 (2)	−0.0115 (17)	0.0017 (16)	0.0169 (17)
C20	0.070 (3)	0.0349 (18)	0.060 (2)	−0.0101 (17)	−0.005 (2)	0.0076 (17)
C21	0.067 (2)	0.0373 (18)	0.047 (2)	−0.0151 (17)	−0.0100 (17)	0.0023 (15)
C22	0.067 (3)	0.080 (3)	0.062 (3)	−0.015 (2)	−0.008 (2)	0.032 (2)
S1	0.0328 (4)	0.0434 (5)	0.0423 (5)	−0.0134 (3)	−0.0019 (3)	0.0049 (3)
S2	0.0466 (5)	0.0346 (4)	0.0440 (5)	−0.0101 (3)	−0.0110 (4)	0.0035 (3)
N1	0.0382 (14)	0.0368 (14)	0.0392 (15)	−0.0082 (11)	−0.0049 (11)	0.0043 (11)
N2	0.0591 (18)	0.0344 (14)	0.0495 (17)	−0.0160 (13)	0.0012 (14)	0.0055 (13)
O1	0.0555 (15)	0.0546 (15)	0.0606 (16)	−0.0288 (12)	−0.0140 (12)	0.0003 (12)
O2	0.0398 (13)	0.0673 (17)	0.0541 (15)	−0.0089 (12)	0.0101 (11)	0.0076 (13)
O3	0.0505 (15)	0.0505 (15)	0.0697 (18)	0.0019 (12)	−0.0049 (13)	0.0029 (13)
O4	0.089 (2)	0.0570 (16)	0.0530 (16)	−0.0332 (15)	−0.0285 (15)	0.0058 (13)

C1—C6	1.371 (5)	C13—C15	1.512 (5)
C1—C2	1.382 (5)	C14—H14	0.9300
C1—S1	1.765 (3)	C15—N2	1.461 (5)
C2—C3	1.382 (5)	C15—H15A	0.9700
C2—H2A	0.9300	C15—H15B	0.9700
C3—C4	1.381 (5)	C16—C21	1.374 (5)
C3—H3	0.9300	C16—C17	1.388 (5)
C4—C5	1.381 (5)	C16—S2	1.760 (3)
C4—C7	1.502 (5)	C17—C18	1.370 (5)
C5—C6	1.389 (5)	C17—H17	0.9300
C5—H5	0.9300	C18—C19	1.374 (6)
C6—H6	0.9300	C18—H18	0.9300
C7—H7A	0.9600	C19—C20	1.385 (6)
C7—H7B	0.9600	C19—C22	1.505 (5)
C7—H7C	0.9600	C20—C21	1.381 (5)
C8—N1	1.459 (4)	C20—H20	0.9300
C8—C9	1.508 (4)	C21—H21	0.9300
C8—H8A	0.9700	C22—H22A	0.9600
C8—H8B	0.9700	C22—H22B	0.9600
C9—C10	1.374 (5)	C22—H22C	0.9600
C9—C14	1.386 (4)	S1—O1	1.429 (3)
C10—C11	1.384 (5)	S1—O2	1.434 (3)
C10—H10	0.9300	S1—N1	1.621 (3)
C11—C12	1.371 (5)	S2—O4	1.422 (3)
C11—H11	0.9300	S2—O3	1.424 (3)
C12—C13	1.386 (5)	S2—N2	1.614 (3)
C12—H12	0.9300	N1—H1	0.9305
C13—C14	1.373 (4)	N2—H2	0.9265
C6—C1—C2	120.5 (3)	N2—C15—C13	111.3 (3)
C6—C1—S1	119.5 (3)	N2—C15—H15A	109.4
C2—C1—S1	120.0 (3)	C13—C15—H15A	109.4
C3—C2—C1	118.9 (3)	N2—C15—H15B	109.4
C3—C2—H2A	120.5	C13—C15—H15B	109.4
C1—C2—H2A	120.5	H15A—C15—H15B	108.0
C4—C3—C2	121.5 (3)	C21—C16—C17	119.7 (3)
C4—C3—H3	119.2	C21—C16—S2	120.3 (3)
C2—C3—H3	119.2	C17—C16—S2	120.0 (3)
C3—C4—C5	118.6 (3)	C18—C17—C16	120.2 (3)
C3—C4—C7	121.3 (4)	C18—C17—H17	119.9
C5—C4—C7	120.1 (4)	C16—C17—H17	119.9
C4—C5—C6	120.5 (3)	C17—C18—C19	121.0 (4)
C4—C5—H5	119.7	C17—C18—H18	119.5
C6—C5—H5	119.7	C19—C18—H18	119.5
C1—C6—C5	119.8 (3)	C18—C19—C20	118.3 (3)
C1—C6—H6	120.1	C18—C19—C22	121.2 (4)
C5—C6—H6	120.1	C20—C19—C22	120.5 (4)
C4—C7—H7A	109.5	C21—C20—C19	121.5 (3)
C4—C7—H7B	109.5	C21—C20—H20	119.3
H7A—C7—H7B	109.5	C19—C20—H20	119.3
C4—C7—H7C	109.5	C16—C21—C20	119.3 (4)
H7A—C7—H7C	109.5	C16—C21—H21	120.4
H7B—C7—H7C	109.5	C20—C21—H21	120.4
N1—C8—C9	110.5 (3)	C19—C22—H22A	109.5
N1—C8—H8A	109.6	C19—C22—H22B	109.5
C9—C8—H8A	109.6	H22A—C22—H22B	109.5
N1—C8—H8B	109.6	C19—C22—H22C	109.5
C9—C8—H8B	109.6	H22A—C22—H22C	109.5
H8A—C8—H8B	108.1	H22B—C22—H22C	109.5
C10—C9—C14	118.9 (3)	O1—S1—O2	119.71 (17)
C10—C9—C8	120.7 (3)	O1—S1—N1	106.78 (15)
C14—C9—C8	120.4 (3)	O2—S1—N1	105.48 (15)
C9—C10—C11	120.3 (3)	O1—S1—C1	108.30 (16)
C9—C10—H10	119.9	O2—S1—C1	107.56 (15)
C11—C10—H10	119.9	N1—S1—C1	108.60 (14)
C12—C11—C10	120.4 (3)	O4—S2—O3	119.86 (18)
C12—C11—H11	119.8	O4—S2—N2	105.13 (17)
C10—C11—H11	119.8	O3—S2—N2	107.23 (17)
C11—C12—C13	119.9 (3)	O4—S2—C16	107.55 (16)
C11—C12—H12	120.1	O3—S2—C16	107.40 (17)
C13—C12—H12	120.1	N2—S2—C16	109.40 (16)
C14—C13—C12	119.3 (3)	C8—N1—S1	118.4 (2)
C14—C13—C15	120.7 (3)	C8—N1—H1	114.7
C12—C13—C15	120.0 (3)	S1—N1—H1	113.5
C13—C14—C9	121.2 (3)	C15—N2—S2	120.7 (3)
C13—C14—H14	119.4	C15—N2—H2	113.3
C9—C14—H14	119.4	S2—N2—H2	116.1
C6—C1—C2—C3	1.3 (5)	C17—C18—C19—C20	0.1 (6)
S1—C1—C2—C3	−179.8 (3)	C17—C18—C19—C22	179.6 (4)
C1—C2—C3—C4	−0.8 (5)	C18—C19—C20—C21	0.0 (6)
C2—C3—C4—C5	0.2 (5)	C22—C19—C20—C21	−179.4 (4)
C2—C3—C4—C7	−179.8 (3)	C17—C16—C21—C20	−0.4 (6)
C3—C4—C5—C6	0.1 (5)	S2—C16—C21—C20	177.8 (3)
C7—C4—C5—C6	−180.0 (3)	C19—C20—C21—C16	0.1 (6)
C2—C1—C6—C5	−1.0 (5)	C6—C1—S1—O1	172.7 (3)
S1—C1—C6—C5	−180.0 (3)	C2—C1—S1—O1	−6.2 (3)
C4—C5—C6—C1	0.4 (6)	C6—C1—S1—O2	42.0 (3)
N1—C8—C9—C10	−114.7 (4)	C2—C1—S1—O2	−136.9 (3)
N1—C8—C9—C14	65.5 (4)	C6—C1—S1—N1	−71.7 (3)
C14—C9—C10—C11	−0.4 (5)	C2—C1—S1—N1	109.4 (3)
C8—C9—C10—C11	179.8 (3)	C21—C16—S2—O4	14.3 (4)
C9—C10—C11—C12	0.9 (6)	C17—C16—S2—O4	−167.6 (3)
C10—C11—C12—C13	−1.0 (6)	C21—C16—S2—O3	144.5 (3)
C11—C12—C13—C14	0.7 (6)	C17—C16—S2—O3	−37.3 (3)
C11—C12—C13—C15	−178.6 (4)	C21—C16—S2—N2	−99.4 (3)
C12—C13—C14—C9	−0.2 (5)	C17—C16—S2—N2	78.8 (3)
C15—C13—C14—C9	179.1 (3)	C9—C8—N1—S1	−173.1 (2)
C10—C9—C14—C13	0.1 (5)	O1—S1—N1—C8	48.1 (3)
C8—C9—C14—C13	179.9 (3)	O2—S1—N1—C8	176.5 (2)
C14—C13—C15—N2	50.8 (5)	C1—S1—N1—C8	−68.5 (3)
C12—C13—C15—N2	−129.9 (4)	C13—C15—N2—S2	−136.6 (3)
C21—C16—C17—C18	0.6 (6)	O4—S2—N2—C15	172.2 (3)
S2—C16—C17—C18	−177.6 (3)	O3—S2—N2—C15	43.6 (3)
C16—C17—C18—C19	−0.4 (6)	C16—S2—N2—C15	−72.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4i	0.93	2.02	2.896 (4)	156
N2—H2···O2ii	0.93	2.09	2.989 (4)	165
C7—H7A···Cg1iii	0.96	2.74	3.560 (5)	144
C21—H21···Cg2iv	0.93	2.74	3.560 (4)	147

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring and Cg2 is the centroid of the C9–C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4i	0.93	2.02	2.896 (4)	156
N2—H2⋯O2ii	0.93	2.09	2.989 (4)	165
C7—H7A⋯Cg1iii	0.96	2.74	3.560 (5)	144
C21—H21⋯Cg2iv	0.93	2.74	3.560 (4)	147

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