supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

xu2448 scheme

Acta Cryst. (2008). E64, o1771    [ doi:10.1107/S1600536808025919 ]

N,N'-Bis[(E)-2-Benzylidenepropylidene]ethane-1,2-diamine

A. D. Khalaji and S. W. Ng

Abstract top

The two independent molecules in the asymmetric unit of the title Schiff base, C22H24N2, lie across centers of inversion. The C=N double bonds are in a trans configuration.

Comment top

(type here to add)

Related literature top

There are many examples of similar Schiff bases in the current (2008) Cambrige Structural Database; for example, see: Khalaji et al. (2007). For the structure of bis[(E)-3-phenylpropen-1-al]-1,2-diiminoethane, see: Khalaji & Weil (2007).

Experimental top

Ethylenediamine (1 mmol, 60 mg) and α-methylcinnamaldehyde (2 mmol, 292 mg) were dissolved in methanol (10 ml) to give a colorless solution. Slow evaporation of the solvent yielded colorless crystals in about 85% yield.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.98 Å) and were included in the refinement in the riding model approximation, with U(H) fixed at 1.2 to 1.5U(C).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of the two independent molecules of the title compound; probability ellipsoids are set at the 70% level, and H atoms are drawn as spheres of arbitrary radius. The two molecules lie about centers of inversion.
N,N'-Bis[(E)-2-Benzylidenepropylidene]ethane-1,2-diamine top
Crystal data top
C22H24N2Z = 2
Mr = 316.43F000 = 340
Triclinic, P1Dx = 1.183 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 9.524 (2) ÅCell parameters from 1031 reflections
b = 9.576 (2) Åθ = 3.2–28.0º
c = 10.202 (2) ŵ = 0.07 mm−1
α = 88.160 (3)ºT = 100 (2) K
β = 76.865 (2)ºBlock, colorless
γ = 78.651 (3)º0.24 × 0.12 × 0.08 mm
V = 888.3 (3) Å3
Data collection top
Bruker SMART APEX
diffractometer		2186 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Monochromator: graphiteθmax = 25.0º
T = 100(2) Kθmin = 2.1º
ω scansh = −11→11
Absorption correction: Nonek = −11→7
4114 measured reflectionsl = −12→12
3015 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.069H-atom parameters constrained
wR(F2) = 0.228  w = 1/[σ2(Fo2) + (0.0966P)2 + 1.385P]
where P = (Fo2 + 2Fc2)/3
S = 1.13(Δ/σ)max = 0.001
3015 reflectionsΔρmax = 0.34 e Å−3
219 parametersΔρmin = −0.30 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C22H24N2γ = 78.651 (3)º
Mr = 316.43V = 888.3 (3) Å3
Triclinic, P1Z = 2
a = 9.524 (2) ÅMo Kα
b = 9.576 (2) ŵ = 0.07 mm−1
c = 10.202 (2) ÅT = 100 (2) K
α = 88.160 (3)º0.24 × 0.12 × 0.08 mm
β = 76.865 (2)º
Data collection top
Bruker SMART APEX
diffractometer		3015 independent reflections
Absorption correction: None2186 reflections with I > 2σ(I)
4114 measured reflectionsRint = 0.023
Refinement top
R[F2 > 2σ(F2)] = 0.069219 parameters
wR(F2) = 0.228H-atom parameters constrained
S = 1.13Δρmax = 0.34 e Å−3
3015 reflectionsΔρmin = −0.30 e Å−3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.3982 (3)1.1256 (3)0.1398 (3)0.0221 (7)
N20.3642 (3)0.5970 (3)0.1443 (3)0.0220 (7)
C10.1158 (4)1.3426 (4)0.6498 (4)0.0242 (8)
H10.06741.37000.57850.029*
C20.0423 (4)1.3777 (4)0.7810 (4)0.0268 (9)
H2−0.05671.42790.79930.032*
C30.1114 (4)1.3405 (4)0.8862 (4)0.0238 (8)
H30.05971.36460.97620.029*
C40.2550 (4)1.2685 (4)0.8602 (4)0.0238 (8)
H40.30261.24280.93220.029*
C50.3297 (4)1.2335 (4)0.7291 (3)0.0218 (8)
H50.42961.18600.71180.026*
C60.2613 (4)1.2668 (4)0.6210 (3)0.0209 (8)
C70.3478 (4)1.2169 (4)0.4872 (3)0.0211 (8)
H70.45011.18710.48190.025*
C80.3067 (4)1.2062 (4)0.3699 (3)0.0198 (8)
C90.1543 (4)1.2473 (5)0.3469 (4)0.0358 (10)
H9A0.08491.21370.42170.054*
H9B0.15021.20390.26250.054*
H9C0.12791.35120.34150.054*
C100.4227 (4)1.1443 (4)0.2552 (3)0.0209 (8)
H100.52041.11690.26710.025*
C110.5216 (4)1.0601 (4)0.0345 (3)0.0224 (8)
H11A0.60701.02110.07380.027*
H11B0.55001.1325−0.03260.027*
C120.1872 (4)0.8841 (4)0.6385 (4)0.0234 (8)
H120.18260.93910.55990.028*
C130.1387 (4)0.9502 (4)0.7643 (4)0.0235 (8)
H130.10021.04970.77090.028*
C140.1461 (4)0.8727 (4)0.8798 (4)0.0252 (8)
H140.11170.91840.96560.030*
C150.2040 (4)0.7277 (4)0.8698 (4)0.0238 (8)
H150.21120.67400.94880.029*
C160.2510 (4)0.6617 (4)0.7450 (4)0.0224 (8)
H160.29010.56220.73940.027*
C170.2427 (3)0.7372 (4)0.6261 (3)0.0188 (8)
C180.2977 (4)0.6565 (4)0.4993 (4)0.0210 (8)
H180.34950.56260.50850.025*
C190.2885 (4)0.6906 (4)0.3718 (3)0.0201 (8)
C200.2131 (4)0.8296 (4)0.3247 (4)0.0260 (9)
H20A0.11510.85810.38330.039*
H20B0.20410.81840.23200.039*
H20C0.27110.90280.32820.039*
C210.3610 (4)0.5804 (4)0.2695 (3)0.0207 (8)
H210.40840.49150.29770.025*
C220.4398 (4)0.4776 (4)0.0556 (3)0.0245 (8)
H22A0.36870.44210.01450.029*
H22B0.48450.39930.10790.029*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0217 (15)0.0204 (16)0.0237 (17)−0.0038 (12)−0.0043 (13)−0.0017 (12)
N20.0225 (15)0.0213 (16)0.0224 (17)−0.0058 (12)−0.0041 (12)0.0005 (12)
C10.0238 (18)0.026 (2)0.0222 (19)−0.0025 (15)−0.0076 (15)0.0024 (15)
C20.0238 (19)0.027 (2)0.028 (2)−0.0021 (16)−0.0043 (16)−0.0027 (16)
C30.0293 (19)0.0191 (19)0.0221 (19)−0.0049 (15)−0.0035 (15)−0.0022 (15)
C40.030 (2)0.0163 (18)0.027 (2)−0.0048 (15)−0.0112 (16)0.0010 (15)
C50.0228 (18)0.0181 (18)0.026 (2)−0.0040 (15)−0.0085 (15)0.0012 (15)
C60.0238 (18)0.0178 (18)0.0226 (19)−0.0077 (14)−0.0054 (15)0.0012 (14)
C70.0198 (17)0.0186 (18)0.0239 (19)−0.0034 (14)−0.0031 (15)−0.0003 (15)
C80.0233 (18)0.0190 (18)0.0191 (18)−0.0075 (15)−0.0062 (15)0.0033 (14)
C90.028 (2)0.053 (3)0.025 (2)0.0003 (19)−0.0093 (17)−0.0110 (19)
C100.0200 (17)0.0176 (18)0.026 (2)−0.0054 (14)−0.0064 (15)0.0046 (14)
C110.0220 (18)0.026 (2)0.0196 (18)−0.0063 (15)−0.0036 (15)0.0001 (15)
C120.0253 (19)0.023 (2)0.026 (2)−0.0094 (15)−0.0108 (16)0.0056 (15)
C130.0176 (17)0.0210 (19)0.031 (2)−0.0011 (14)−0.0054 (15)−0.0033 (15)
C140.0189 (18)0.030 (2)0.0243 (19)−0.0042 (15)0.0006 (15)−0.0064 (16)
C150.0227 (18)0.030 (2)0.0179 (18)−0.0043 (16)−0.0046 (15)0.0036 (15)
C160.0208 (17)0.0196 (19)0.027 (2)−0.0033 (15)−0.0076 (15)0.0042 (15)
C170.0143 (16)0.0236 (19)0.0185 (18)−0.0059 (14)−0.0021 (13)0.0023 (14)
C180.0196 (17)0.0153 (18)0.028 (2)−0.0020 (14)−0.0057 (15)0.0013 (14)
C190.0190 (17)0.0210 (19)0.0215 (19)−0.0072 (14)−0.0043 (14)0.0018 (14)
C200.028 (2)0.0214 (19)0.025 (2)0.0013 (16)−0.0037 (16)0.0007 (16)
C210.0236 (18)0.0176 (18)0.0222 (19)−0.0061 (15)−0.0059 (14)0.0014 (14)
C220.031 (2)0.0207 (19)0.0220 (19)−0.0058 (16)−0.0067 (16)−0.0025 (15)
Geometric parameters (Å, °) top
N1—C101.276 (5)C11—H11A0.9900
N1—C111.452 (5)C11—H11B0.9900
N2—C211.276 (5)C12—C131.389 (5)
N2—C221.446 (5)C12—C171.401 (5)
C1—C21.380 (5)C12—H120.9500
C1—C61.403 (5)C13—C141.380 (5)
C1—H10.9500C13—H130.9500
C2—C31.384 (5)C14—C151.388 (5)
C2—H20.9500C14—H140.9500
C3—C41.375 (5)C15—C161.380 (5)
C3—H30.9500C15—H150.9500
C4—C51.382 (5)C16—C171.401 (5)
C4—H40.9500C16—H160.9500
C5—C61.401 (5)C17—C181.464 (5)
C5—H50.9500C18—C191.349 (5)
C6—C71.465 (5)C18—H180.9500
C7—C81.354 (5)C19—C211.462 (5)
C7—H70.9500C19—C201.502 (5)
C8—C101.463 (5)C20—H20A0.9800
C8—C91.497 (5)C20—H20B0.9800
C9—H9A0.9800C20—H20C0.9800
C9—H9B0.9800C21—H210.9500
C9—H9C0.9800C22—C22ii1.534 (7)
C10—H100.9500C22—H22A0.9900
C11—C11i1.536 (7)C22—H22B0.9900
C10—N1—C11117.7 (3)H11A—C11—H11B108.2
C21—N2—C22117.0 (3)C13—C12—C17120.8 (3)
C2—C1—C6120.5 (3)C13—C12—H12119.6
C2—C1—H1119.8C17—C12—H12119.6
C6—C1—H1119.8C14—C13—C12120.6 (3)
C1—C2—C3120.7 (3)C14—C13—H13119.7
C1—C2—H2119.7C12—C13—H13119.7
C3—C2—H2119.7C13—C14—C15119.6 (3)
C4—C3—C2119.9 (3)C13—C14—H14120.2
C4—C3—H3120.0C15—C14—H14120.2
C2—C3—H3120.0C16—C15—C14119.8 (3)
C3—C4—C5119.8 (3)C16—C15—H15120.1
C3—C4—H4120.1C14—C15—H15120.1
C5—C4—H4120.1C15—C16—C17121.8 (3)
C4—C5—C6121.4 (3)C15—C16—H16119.1
C4—C5—H5119.3C17—C16—H16119.1
C6—C5—H5119.3C12—C17—C16117.3 (3)
C5—C6—C1117.6 (3)C12—C17—C18125.6 (3)
C5—C6—C7116.9 (3)C16—C17—C18117.1 (3)
C1—C6—C7125.5 (3)C19—C18—C17132.0 (3)
C8—C7—C6131.0 (3)C19—C18—H18114.0
C8—C7—H7114.5C17—C18—H18114.0
C6—C7—H7114.5C18—C19—C21116.0 (3)
C7—C8—C10116.5 (3)C18—C19—C20126.8 (3)
C7—C8—C9126.6 (3)C21—C19—C20117.2 (3)
C10—C8—C9116.9 (3)C19—C20—H20A109.5
C8—C9—H9A109.5C19—C20—H20B109.5
C8—C9—H9B109.5H20A—C20—H20B109.5
H9A—C9—H9B109.5C19—C20—H20C109.5
C8—C9—H9C109.5H20A—C20—H20C109.5
H9A—C9—H9C109.5H20B—C20—H20C109.5
H9B—C9—H9C109.5N2—C21—C19123.5 (3)
N1—C10—C8122.7 (3)N2—C21—H21118.2
N1—C10—H10118.6C19—C21—H21118.2
C8—C10—H10118.6N2—C22—C22ii110.4 (4)
N1—C11—C11i109.5 (3)N2—C22—H22A109.6
N1—C11—H11A109.8C22ii—C22—H22A109.6
C11i—C11—H11A109.8N2—C22—H22B109.6
N1—C11—H11B109.8C22ii—C22—H22B109.6
C11i—C11—H11B109.8H22A—C22—H22B108.1
C6—C1—C2—C30.9 (6)C17—C12—C13—C140.8 (5)
C1—C2—C3—C40.4 (6)C12—C13—C14—C150.7 (5)
C2—C3—C4—C50.0 (5)C13—C14—C15—C16−1.2 (5)
C3—C4—C5—C6−1.6 (5)C14—C15—C16—C170.2 (5)
C4—C5—C6—C12.8 (5)C13—C12—C17—C16−1.8 (5)
C4—C5—C6—C7−176.2 (3)C13—C12—C17—C18−179.5 (3)
C2—C1—C6—C5−2.4 (5)C15—C16—C17—C121.3 (5)
C2—C1—C6—C7176.5 (3)C15—C16—C17—C18179.2 (3)
C5—C6—C7—C8165.1 (4)C12—C17—C18—C19−12.3 (6)
C1—C6—C7—C8−13.8 (6)C16—C17—C18—C19169.9 (4)
C6—C7—C8—C10−177.0 (3)C17—C18—C19—C21178.9 (3)
C6—C7—C8—C91.1 (6)C17—C18—C19—C20−0.6 (6)
C11—N1—C10—C8−178.6 (3)C22—N2—C21—C19−179.8 (3)
C7—C8—C10—N1178.6 (3)C18—C19—C21—N2−178.9 (3)
C9—C8—C10—N10.2 (5)C20—C19—C21—N20.6 (5)
C10—N1—C11—C11i131.7 (4)C21—N2—C22—C22ii−124.0 (4)
Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+1, −y+1, −z.
Acknowledgements top

We thank Gorgan University of Agricultural Sciences and Natural Resources and the University of Malaya supporting this study.

references
References top

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Khalaji, A. D., Brad, K. & Zhang, Y. (2007). Acta Cryst. E63, o4389.

Khalaji, A. D. & Weil, M. (2007). Anal. Sci. 23, x187–x188.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Westrip, S. P. (2008). publCIF. In preparation.