(E,E)-N,N'-Bis[4-(methyl-sulfon-yl)benzyl-idene]ethane-1,2-diamine.

In the crystal structure of the title Schiff base compound, C(18)H(20)N(2)O(4)S(2), the mol-ecule lies across a crystallographic inversion centre. The torsion angle of the N-C-C-N fragment is 180°, as the inversion centre bis-ects the central C-C bond. The crystal packing is stabilized by C-H⋯O hydrogen bonds and aromatic π-π stacking inter-actions with a centroid-centroid distance of 3.913 (2) Å.

Related literature

For bond-length data, see: Allen et al. (1987 ▶); For the crystal structure of a similar Schiff base compound, see: Sun et al. (2004 ▶). For the crystal structure of a precursor mol­ecule used in the synthesis of the title compound, see: Qian & Cui (2009 ▶).

Experimental

Crystal data

C18H20N2O4S2

M = 392.48

Triclinic,

a = 7.0100 (14) Å

b = 8.0530 (16) Å

c = 8.8740 (18) Å

α = 88.06 (3)°

β = 67.56 (3)°

γ = 87.60 (3)°

V = 462.53 (19) Å3

Z = 1

Mo Kα radiation

μ = 0.31 mm−1

T = 293 K

0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: multi-scan (SHELXTL; Sheldrick, 2008 ▶) T min = 0.940, T max = 0.969

1830 measured reflections

1683 independent reflections

1374 reflections with I > 2σ(I)

R int = 0.017

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.153

S = 1.00

1683 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.33 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809047527/wm2281sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809047527/wm2281Isup2.hkl

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

C18H20N2O4S2	Z = 1
Mr = 392.48	F(000) = 206
Triclinic, P1	Dx = 1.409 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0100 (14) Å	Cell parameters from 25 reflections
b = 8.0530 (16) Å	θ = 9–13°
c = 8.8740 (18) Å	µ = 0.31 mm−1
α = 88.06 (3)°	T = 293 K
β = 67.56 (3)°	Block, yellow
γ = 87.60 (3)°	0.20 × 0.10 × 0.10 mm
V = 462.53 (19) Å3

Enraf–Nonius CAD-4 diffractometer	1374 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.017
graphite	θmax = 25.3°, θmin = 2.5°
ω/2θ scans	h = 0→8
Absorption correction: multi-scan (SHELXTL; Sheldrick, 2008)	k = −9→9
Tmin = 0.940, Tmax = 0.969	l = −9→10
1830 measured reflections	3 standard reflections every 200 reflections
1683 independent reflections	intensity decay: 1%

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.1P)2 + 0.140P] where P = (Fo2 + 2Fc2)/3
1683 reflections	(Δ/σ)max < 0.001
118 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.33 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
S	0.75133 (11)	0.83172 (8)	0.57111 (9)	0.0414 (3)
N	0.1391 (4)	0.1964 (3)	0.9738 (3)	0.0443 (6)
O1	0.9506 (3)	0.7668 (3)	0.5545 (4)	0.0715 (8)
C1	−0.0335 (5)	0.0843 (4)	1.0382 (4)	0.0479 (8)
H1B	−0.1492	0.1292	1.0136	0.057*
H1C	−0.0774	0.0735	1.1557	0.057*
O2	0.7244 (4)	0.8981 (3)	0.4285 (3)	0.0532 (6)
C2	0.1219 (4)	0.3116 (3)	0.8807 (3)	0.0410 (7)
H2B	0.0013	0.3200	0.8601	0.049*
C3	0.2822 (4)	0.4346 (3)	0.8017 (3)	0.0366 (6)
C4	0.2457 (4)	0.5596 (4)	0.7043 (4)	0.0422 (7)
H4A	0.1227	0.5624	0.6871	0.051*
C5	0.3882 (4)	0.6802 (3)	0.6324 (3)	0.0405 (7)
H5A	0.3619	0.7641	0.5677	0.049*
C6	0.5702 (4)	0.6742 (3)	0.6579 (3)	0.0362 (6)
C7	0.6120 (5)	0.5482 (4)	0.7525 (4)	0.0503 (8)
H7A	0.7364	0.5441	0.7675	0.060*
C8	0.4670 (5)	0.4292 (4)	0.8242 (4)	0.0472 (8)
H8A	0.4937	0.3447	0.8881	0.057*
C9	0.6747 (6)	0.9854 (4)	0.7201 (4)	0.0578 (9)
H9A	0.7652	1.0772	0.6829	0.087*
H9B	0.6811	0.9399	0.8195	0.087*
H9C	0.5357	1.0231	0.7393	0.087*

	U11	U22	U33	U12	U13	U23
S	0.0377 (4)	0.0343 (4)	0.0478 (5)	−0.0113 (3)	−0.0116 (3)	0.0135 (3)
N	0.0499 (15)	0.0369 (13)	0.0412 (14)	−0.0182 (11)	−0.0110 (11)	0.0078 (11)
O1	0.0380 (13)	0.0554 (14)	0.111 (2)	−0.0117 (10)	−0.0194 (13)	0.0313 (14)
C1	0.0466 (17)	0.0404 (16)	0.0470 (17)	−0.0190 (13)	−0.0059 (13)	0.0091 (13)
O2	0.0648 (15)	0.0483 (12)	0.0440 (12)	−0.0185 (10)	−0.0178 (10)	0.0166 (10)
C2	0.0378 (15)	0.0369 (15)	0.0445 (16)	−0.0103 (12)	−0.0106 (13)	0.0008 (12)
C3	0.0399 (15)	0.0289 (13)	0.0362 (14)	−0.0081 (11)	−0.0086 (12)	0.0024 (11)
C4	0.0345 (15)	0.0385 (15)	0.0533 (18)	−0.0040 (12)	−0.0167 (13)	0.0079 (13)
C5	0.0419 (16)	0.0330 (14)	0.0455 (16)	−0.0032 (12)	−0.0160 (13)	0.0109 (12)
C6	0.0372 (15)	0.0300 (13)	0.0387 (14)	−0.0081 (11)	−0.0116 (12)	0.0078 (11)
C7	0.0437 (17)	0.0461 (17)	0.067 (2)	−0.0149 (13)	−0.0280 (15)	0.0225 (15)
C8	0.0528 (18)	0.0381 (15)	0.0572 (18)	−0.0143 (13)	−0.0287 (15)	0.0213 (13)
C9	0.068 (2)	0.0509 (19)	0.055 (2)	−0.0248 (16)	−0.0214 (17)	0.0071 (15)

S—O1	1.426 (2)	C3—C4	1.384 (4)
S—O2	1.433 (2)	C4—C5	1.379 (4)
S—C9	1.755 (4)	C4—H4A	0.9300
S—C6	1.771 (3)	C5—C6	1.377 (4)
N—C2	1.254 (4)	C5—H5A	0.9300
N—C1	1.461 (3)	C6—C7	1.388 (4)
C1—C1i	1.513 (6)	C7—C8	1.380 (4)
C1—H1B	0.9700	C7—H7A	0.9300
C1—H1C	0.9700	C8—H8A	0.9300
C2—C3	1.476 (4)	C9—H9A	0.9600
C2—H2B	0.9300	C9—H9B	0.9600
C3—C8	1.382 (4)	C9—H9C	0.9600
O1—S—O2	118.21 (16)	C5—C4—H4A	119.4
O1—S—C9	108.72 (19)	C3—C4—H4A	119.4
O2—S—C9	108.48 (16)	C6—C5—C4	118.9 (3)
O1—S—C6	108.36 (14)	C6—C5—H5A	120.6
O2—S—C6	108.51 (14)	C4—C5—H5A	120.6
C9—S—C6	103.57 (15)	C5—C6—C7	121.0 (3)
C2—N—C1	116.2 (3)	C5—C6—S	119.4 (2)
N—C1—C1i	109.3 (3)	C7—C6—S	119.6 (2)
N—C1—H1B	109.8	C8—C7—C6	119.2 (3)
C1i—C1—H1B	109.8	C8—C7—H7A	120.4
N—C1—H1C	109.8	C6—C7—H7A	120.4
C1i—C1—H1C	109.8	C7—C8—C3	120.6 (3)
H1B—C1—H1C	108.3	C7—C8—H8A	119.7
N—C2—C3	123.8 (3)	C3—C8—H8A	119.7
N—C2—H2B	118.1	S—C9—H9A	109.5
C3—C2—H2B	118.1	S—C9—H9B	109.5
C8—C3—C4	119.1 (2)	H9A—C9—H9B	109.5
C8—C3—C2	121.7 (3)	S—C9—H9C	109.5
C4—C3—C2	119.2 (3)	H9A—C9—H9C	109.5
C5—C4—C3	121.2 (3)	H9B—C9—H9C	109.5
C2—N—C1—C1i	110.1 (4)	O2—S—C6—C5	−26.6 (3)
C1—N—C2—C3	−178.8 (3)	C9—S—C6—C5	88.5 (3)
N—C2—C3—C8	0.9 (5)	O1—S—C6—C7	24.9 (3)
N—C2—C3—C4	−178.3 (3)	O2—S—C6—C7	154.4 (3)
C8—C3—C4—C5	−1.3 (5)	C9—S—C6—C7	−90.4 (3)
C2—C3—C4—C5	177.9 (3)	C5—C6—C7—C8	−1.2 (5)
C3—C4—C5—C6	0.4 (4)	S—C6—C7—C8	177.8 (3)
C4—C5—C6—C7	0.8 (5)	C6—C7—C8—C3	0.3 (5)
C4—C5—C6—S	−178.2 (2)	C4—C3—C8—C7	0.9 (5)
O1—S—C6—C5	−156.1 (3)	C2—C3—C8—C7	−178.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O1ii	0.93	2.52	3.241 (4)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯O1i	0.93	2.52	3.241 (4)	135

Symmetry code: (i) .