(E,E)-N,N′-Bis[4-(methyl­sulfon­yl)benzyl­idene]ethane-1,2-diamine

Qian, S.-S.; Cui, H.-Y.

doi:10.1107/S1600536809047527

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3093

doi:10.1107/S1600536809047527

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(E,E)-N,N′-Bis[4-(methylsulfonyl)benzylidene]ethane-1,2-diamine

Shao-Song Qian ^a ^* and Hong-You Cui ^b

^aSchool of Life Sciences, ShanDong University of Technology, ZiBo 255049, People's Republic of China, and ^bSchool of Chemical Engineering, ShanDong University of Technology, ZiBo 255049, People's Republic of China
^*Correspondence e-mail: njuqss@yahoo.com.cn

(Received 8 November 2009; accepted 10 November 2009; online 14 November 2009)

In the crystal structure of the title Schiff base compound, C₁₈H₂₀N₂O₄S₂, the molecule lies across a crystallographic inversion centre. The torsion angle of the N—C—C—N fragment is 180°, as the inversion centre bisects the central C—C bond. The crystal packing is stabilized by C—H⋯O hydrogen bonds and aromatic π–π stacking interactions 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_r = 392.48
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.045
wR(F²) = 0.153
S = 1.00
1683 reflections
118 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.33 e Å⁻³

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) x-1, y, z.

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.

Supporting information

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

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

checkCIF report

Comment top

The title compound, (I), acts as an important precursor for the synthesis of Schiff base complexes. As an extension of our work on the structural characterization of Schiff base compounds, the crystal structure is reported here.

The asymmetric unit contains one-half of the molecule of (I), the other half being inversion-related by symmetry operation (-x, -y, 2-z) (Fig.1). All the bond lengths are within normal ranges (Allen et al., 1987) and comparable to the values observed in other similar compounds (Qian & Cui, 2009; Sun et al., 2004). The crystal packing is stabilized by C—H···O hydrogen bonds and aromatic π-π stacking interactions with a centroid-centroid distance of 3.913 (2) Å (Figure 2, Table 1). The torsion angle of the N—C—C—N fragment is 180 °, as the inversion centre bisects the central C—C bond.

Related literature top

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 top

4-(methylsulfonyl)benzaldehyde (0.184 g, 1 mmol) (Qian & Cui, 2009) and ethylene diamine (0.03 g, 0.5 mmol) were dissolved in acetonitrile (20 ml). The mixture was stirred at room temperature for 10 min to give a clear yellow solution. After keeping the solution in air for 10 d, yellow block-shaped crystals of (I) were formed at the bottom of the vessel on slow evaporation of the solvent.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 35% probability level. The molecule is completed by symmetry operation (-x, -y, 2-z) across the central C—C bond.
	Fig. 2. Plot of the crystal packing of compound (I). C—H···O hydrogen bonds are indicated with dotted lines.

(E,E)-N,N'-Bis[4- (methylsulfonyl)benzylidene]ethane-1,2-diamine top

Crystal data top

C₁₈H₂₀N₂O₄S₂	Z = 1
M_r = 392.48	F(000) = 206
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.1P)² + 0.140P] where P = (F_o² + 2F_c²)/3
1683 reflections	(Δ/σ)_max < 0.001
118 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₁₈H₂₀N₂O₄S₂	γ = 87.60 (3)°
M_r = 392.48	V = 462.53 (19) Å³
Triclinic, P1	Z = 1
a = 7.0100 (14) Å	Mo Kα radiation
b = 8.0530 (16) Å	µ = 0.31 mm⁻¹
c = 8.8740 (18) Å	T = 293 K
α = 88.06 (3)°	0.20 × 0.10 × 0.10 mm
β = 67.56 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1374 reflections with I > 2σ(I)
Absorption correction: multi-scan (SHELXTL; Sheldrick, 2008)	R_int = 0.017
T_min = 0.940, T_max = 0.969	3 standard reflections every 200 reflections
1830 measured reflections	intensity decay: 1%
1683 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.153	H-atom parameters constrained
S = 1.00	Δρ_max = 0.20 e Å⁻³
1683 reflections	Δρ_min = −0.33 e Å⁻³
118 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x, −y, −z+2.

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₀N₂O₄S₂
M_r	392.48
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.0100 (14), 8.0530 (16), 8.8740 (18)
α, β, γ (°)	88.06 (3), 67.56 (3), 87.60 (3)
V (Å³)	462.53 (19)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	Multi-scan (SHELXTL; Sheldrick, 2008)
T_min, T_max	0.940, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	1830, 1683, 1374
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.153, 1.00
No. of reflections	1683
No. of parameters	118
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.33

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O1ⁱ	0.93	2.52	3.241 (4)	134.6

Symmetry code: (i) x−1, y, z.

Acknowledgements

This project was sponsored by ShanDong Province Science & Technology Innovation Foundation.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
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