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Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): o1771.
Published online 2008 August 16. doi:  10.1107/S1600536808025919
PMCID: PMC2960613

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

Abstract

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.

Related literature

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

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Object name is e-64-o1771-scheme1.jpg

Experimental

Crystal data

  • C22H24N2
  • M r = 316.43
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1771-efi1.jpg
  • a = 9.524 (2) Å
  • b = 9.576 (2) Å
  • c = 10.202 (2) Å
  • α = 88.160 (3)°
  • β = 76.865 (2)°
  • γ = 78.651 (3)°
  • V = 888.3 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 100 (2) K
  • 0.24 × 0.12 × 0.08 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: none
  • 4114 measured reflections
  • 3015 independent reflections
  • 2186 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.069
  • wR(F 2) = 0.228
  • S = 1.13
  • 3015 reflections
  • 219 parameters
  • H-atom parameters constrained
  • Δρmax = 0.34 e Å−3
  • Δρmin = −0.30 e Å−3

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

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808025919/xu2448sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808025919/xu2448Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

(type here to add)

Experimental

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

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).

Figures

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.

Crystal data

C22H24N2Z = 2
Mr = 316.43F000 = 340
Triclinic, P1Dx = 1.183 Mg m3
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 mm1
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

Bruker SMART APEX diffractometer2186 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

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 Å3
219 parametersΔρmin = −0.30 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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

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)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2448).

References

  • 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. [PubMed]
  • Westrip, S. P. (2008). publCIF In preparation.

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