supplementary materials


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

ez2115 scheme

Acta Cryst. (2008). E64, o565    [ doi:10.1107/S1600536808001463 ]

N-{(E)-4-[(E)-(Dodecylimino)methyl]benzylidene}dodecan-1-imine

B. Wang, R. Wan, L.-H. Yin, F. Han and J.-T. Wang

Abstract top

The title compound, C32H56N2, was synthesized by the reaction of terephthalaldehyde and dodecan-1-amine. The imines adopt trans conformations, with the two halves of the molecule related to each other by a centre of symmetry.

Comment top

Schiff compounds and their derivatives containing long carbon chains are of great interest because of their surface active properties. They can be used as starting materials for producing polymers (Nishikawa, et al., 1992). Certain imines coordinated to metals have also received a great deal of attention recently, due to their antibacterial and antifungal activities (Sharaby, 2007).

We report here the crystal structure of the title compound, (I). The molecular structure of (I) is shown in Fig. 1. The N—C double bonds and the benzene ring lie in the same plane. The double bonds conjugate with the benzene ring. The molecule is centrosymmetric. The bond lengths and angles are within normal ranges (Allen et al., 1987).

Related literature top

For related literature, see: Sharaby (2007); Nishikawa et al. (1992). For bond-length data, see: Allen et al. (1987).

Experimental top

Terephthalaldehyde (5 mmol) and dodecan-1-amine (10 mmol) were dissolved in toluene (50 ml). The reaction mixture was allowed to reflux for 5 h, then left to cool to room temperature, filtered, and the solid was recrystallized from ethanol to give pure compound (I) (m.p. 333 K). Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution.

Refinement top

All H atoms bonded to the C atoms were placed geometrically at distances of 0.93–0.97 Å and included in the refinement in riding motion approximation with Uiso(H) = 1.2 or 1.5Ueq of the carrier atom.

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
[Figure 1] Fig. 1. A view of the molecular structure of (I), showing the atom labelling scheme and ellipsoids at the 50% probability level.
N-{(E)-4-[(E)-(Dodecylimino)methyl]benzylidene}dodecan-\ 1-imine ? top
Crystal data top
C32H56N2Z = 1
Mr = 468.80F000 = 262
Triclinic, P1Dx = 1.006 Mg m−3
Hall symbol: -P 1Melting point = 332–333 K
a = 4.7370 (9) ÅMo Kα radiation
λ = 0.71073 Å
b = 5.5190 (11) ÅCell parameters from 25 reflections
c = 30.315 (6) Åθ = 9–13º
α = 91.18 (3)ºµ = 0.06 mm−1
β = 93.44 (3)ºT = 298 (2) K
γ = 101.75 (3)ºBlock, colorless
V = 774.1 (3) Å30.30 × 0.20 × 0.10 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer		Rint = 0.044
Radiation source: fine-focus sealed tubeθmax = 26.0º
Monochromator: graphiteθmin = 1.4º
T = 298(2) Kh = −5→5
ω/2θ scansk = −6→6
Absorption correction: ψ scan
(North et al., 1968)		l = 0→37
Tmin = 0.953, Tmax = 0.9643 standard reflections
3409 measured reflections every 200 reflections
3020 independent reflections intensity decay: none
1271 reflections with I > 2σ(I)
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)] = 0.065H-atom parameters constrained
wR(F2) = 0.171  w = 1/[σ2(Fo2) + (0.06P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
3020 reflectionsΔρmax = 0.11 e Å−3
154 parametersΔρmin = −0.12 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C32H56N2γ = 101.75 (3)º
Mr = 468.80V = 774.1 (3) Å3
Triclinic, P1Z = 1
a = 4.7370 (9) ÅMo Kα
b = 5.5190 (11) ŵ = 0.06 mm−1
c = 30.315 (6) ÅT = 298 (2) K
α = 91.18 (3)º0.30 × 0.20 × 0.10 mm
β = 93.44 (3)º
Data collection top
Enraf–Nonius CAD-4
diffractometer		1271 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)		Rint = 0.044
Tmin = 0.953, Tmax = 0.9643 standard reflections
3409 measured reflections every 200 reflections
3020 independent reflections intensity decay: none
Refinement top
R[F2 > 2σ(F2)] = 0.065154 parameters
wR(F2) = 0.171H-atom parameters constrained
S = 1.06Δρmax = 0.11 e Å−3
3020 reflectionsΔρmin = −0.12 e Å−3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.2538 (4)−0.7333 (4)0.10048 (7)0.0778 (7)
C10.7923 (7)1.2784 (5)0.45915 (9)0.1139 (11)
H1A0.69481.36060.47990.171*
H1B0.89341.39770.44000.171*
H1C0.92781.19850.47490.171*
C20.5752 (6)1.0886 (5)0.43217 (9)0.0957 (9)
H2A0.47020.97340.45210.115*
H2B0.43721.17180.41710.115*
C30.6950 (5)0.9444 (4)0.39859 (8)0.0776 (7)
H3A0.83300.86120.41360.093*
H3B0.80021.05960.37860.093*
C40.4773 (5)0.7540 (4)0.37145 (8)0.0748 (7)
H4A0.37270.63820.39140.090*
H4B0.33890.83700.35650.090*
C50.6000 (5)0.6097 (4)0.33745 (7)0.0698 (7)
H5A0.73670.52480.35240.084*
H5B0.70600.72520.31760.084*
C60.3788 (5)0.4215 (4)0.31028 (7)0.0683 (7)
H6A0.24500.50680.29470.082*
H6B0.26950.30840.33010.082*
C70.5035 (5)0.2726 (4)0.27696 (7)0.0672 (7)
H7A0.61540.38610.25740.081*
H7B0.63510.18550.29260.081*
C80.2832 (5)0.0869 (4)0.24921 (7)0.0665 (7)
H8A0.15360.17420.23310.080*
H8B0.1691−0.02510.26870.080*
C90.4102 (5)−0.0638 (4)0.21653 (7)0.0680 (7)
H9A0.5357−0.15440.23270.082*
H9B0.52890.04870.19760.082*
C100.1910 (5)−0.2461 (4)0.18760 (7)0.0706 (7)
H10A0.0643−0.35280.20640.085*
H10B0.0734−0.15530.16980.085*
C110.3247 (5)−0.4049 (4)0.15738 (7)0.0679 (7)
H11A0.4605−0.29780.14000.081*
H11B0.4328−0.50290.17530.081*
C120.1100 (5)−0.5762 (5)0.12654 (8)0.0814 (8)
H12A−0.0327−0.67880.14350.098*
H12B0.0105−0.47970.10690.098*
C130.2374 (5)−0.7155 (4)0.05935 (9)0.0691 (7)
H13A0.1336−0.60410.04720.083*
C140.3736 (5)−0.8616 (4)0.02936 (8)0.0599 (6)
C150.5322 (5)−1.0284 (4)0.04476 (8)0.0662 (7)
H15A0.5576−1.04790.07500.079*
C160.3458 (5)−0.8331 (4)−0.01595 (9)0.0705 (7)
H16A0.2430−0.7184−0.02700.085*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0771 (14)0.0880 (15)0.0692 (14)0.0179 (12)0.0158 (12)−0.0196 (12)
C10.129 (3)0.098 (2)0.105 (2)0.007 (2)0.003 (2)−0.0417 (18)
C20.098 (2)0.0910 (19)0.092 (2)0.0058 (17)0.0204 (17)−0.0272 (17)
C30.0739 (17)0.0762 (16)0.0810 (18)0.0124 (14)0.0088 (14)−0.0160 (14)
C40.0687 (16)0.0754 (16)0.0798 (18)0.0121 (14)0.0158 (14)−0.0155 (14)
C50.0625 (15)0.0703 (15)0.0782 (17)0.0153 (13)0.0171 (13)−0.0122 (13)
C60.0582 (14)0.0693 (15)0.0765 (17)0.0104 (13)0.0124 (13)−0.0116 (13)
C70.0611 (15)0.0663 (14)0.0754 (16)0.0136 (13)0.0157 (13)−0.0104 (12)
C80.0625 (15)0.0688 (14)0.0696 (16)0.0153 (13)0.0137 (13)−0.0091 (12)
C90.0643 (15)0.0718 (15)0.0713 (16)0.0190 (13)0.0196 (13)−0.0097 (13)
C100.0614 (15)0.0778 (16)0.0726 (17)0.0137 (14)0.0135 (13)−0.0134 (13)
C110.0690 (16)0.0721 (15)0.0657 (16)0.0187 (13)0.0189 (13)−0.0079 (12)
C120.0737 (17)0.0956 (18)0.0769 (18)0.0210 (16)0.0184 (15)−0.0256 (15)
C130.0552 (15)0.0678 (15)0.0824 (19)0.0085 (13)0.0094 (14)−0.0150 (14)
C140.0494 (14)0.0552 (14)0.0723 (17)0.0034 (12)0.0120 (13)−0.0098 (12)
C150.0690 (16)0.0692 (15)0.0596 (15)0.0108 (14)0.0099 (13)−0.0034 (13)
C160.0670 (17)0.0724 (16)0.0747 (19)0.0195 (14)0.0098 (14)−0.0049 (14)
Geometric parameters (Å, °) top
N1—C131.252 (3)C7—H7B0.9700
N1—C121.454 (2)C8—C91.509 (2)
C1—C21.500 (3)C8—H8A0.9700
C1—H1A0.9600C8—H8B0.9700
C1—H1B0.9600C9—C101.513 (3)
C1—H1C0.9600C9—H9A0.9700
C2—C31.487 (3)C9—H9B0.9700
C2—H2A0.9700C10—C111.507 (2)
C2—H2B0.9700C10—H10A0.9700
C3—C41.505 (3)C10—H10B0.9700
C3—H3A0.9700C11—C121.503 (3)
C3—H3B0.9700C11—H11A0.9700
C4—C51.504 (2)C11—H11B0.9700
C4—H4A0.9700C12—H12A0.9700
C4—H4B0.9700C12—H12B0.9700
C5—C61.508 (3)C13—C141.464 (3)
C5—H5A0.9700C13—H13A0.9300
C5—H5B0.9700C14—C151.374 (3)
C6—C71.510 (2)C14—C161.387 (3)
C6—H6A0.9700C15—C16i1.376 (3)
C6—H6B0.9700C15—H15A0.9300
C7—C81.507 (3)C16—C15i1.376 (3)
C7—H7A0.9700C16—H16A0.9300
C13—N1—C12117.7 (2)C7—C8—C9114.44 (18)
C2—C1—H1A109.5C7—C8—H8A108.7
C2—C1—H1B109.5C9—C8—H8A108.7
H1A—C1—H1B109.5C7—C8—H8B108.7
C2—C1—H1C109.5C9—C8—H8B108.7
H1A—C1—H1C109.5H8A—C8—H8B107.6
H1B—C1—H1C109.5C8—C9—C10114.96 (18)
C3—C2—C1115.7 (2)C8—C9—H9A108.5
C3—C2—H2A108.4C10—C9—H9A108.5
C1—C2—H2A108.4C8—C9—H9B108.5
C3—C2—H2B108.4C10—C9—H9B108.5
C1—C2—H2B108.4H9A—C9—H9B107.5
H2A—C2—H2B107.4C11—C10—C9113.62 (18)
C2—C3—C4115.7 (2)C11—C10—H10A108.8
C2—C3—H3A108.3C9—C10—H10A108.8
C4—C3—H3A108.3C11—C10—H10B108.8
C2—C3—H3B108.3C9—C10—H10B108.8
C4—C3—H3B108.3H10A—C10—H10B107.7
H3A—C3—H3B107.4C12—C11—C10114.14 (18)
C5—C4—C3115.43 (18)C12—C11—H11A108.7
C5—C4—H4A108.4C10—C11—H11A108.7
C3—C4—H4A108.4C12—C11—H11B108.7
C5—C4—H4B108.4C10—C11—H11B108.7
C3—C4—H4B108.4H11A—C11—H11B107.6
H4A—C4—H4B107.5N1—C12—C11110.77 (19)
C4—C5—C6114.74 (17)N1—C12—H12A109.5
C4—C5—H5A108.6C11—C12—H12A109.5
C6—C5—H5A108.6N1—C12—H12B109.5
C4—C5—H5B108.6C11—C12—H12B109.5
C6—C5—H5B108.6H12A—C12—H12B108.1
H5A—C5—H5B107.6N1—C13—C14123.2 (3)
C5—C6—C7114.56 (17)N1—C13—H13A118.4
C5—C6—H6A108.6C14—C13—H13A118.4
C7—C6—H6A108.6C15—C14—C16118.0 (2)
C5—C6—H6B108.6C15—C14—C13121.8 (2)
C7—C6—H6B108.6C16—C14—C13120.2 (2)
H6A—C6—H6B107.6C14—C15—C16i120.9 (2)
C8—C7—C6114.84 (18)C14—C15—H15A119.6
C8—C7—H7A108.6C16i—C15—H15A119.6
C6—C7—H7A108.6C15i—C16—C14121.1 (2)
C8—C7—H7B108.6C15i—C16—H16A119.5
C6—C7—H7B108.6C14—C16—H16A119.5
H7A—C7—H7B107.5
C1—C2—C3—C4−179.9 (2)C13—N1—C12—C11−118.5 (3)
C2—C3—C4—C5179.8 (2)C10—C11—C12—N1−176.5 (2)
C3—C4—C5—C6−179.4 (2)C12—N1—C13—C14179.61 (18)
C4—C5—C6—C7−178.6 (2)N1—C13—C14—C15−0.5 (3)
C5—C6—C7—C8−179.1 (2)N1—C13—C14—C16179.8 (2)
C6—C7—C8—C9−179.04 (19)C16—C14—C15—C16i−1.5 (3)
C7—C8—C9—C10−178.4 (2)C13—C14—C15—C16i178.85 (19)
C8—C9—C10—C11−176.34 (19)C15—C14—C16—C15i1.5 (3)
C9—C10—C11—C12−176.5 (2)C13—C14—C16—C15i−178.85 (19)
Symmetry codes: (i) −x+1, −y−2, −z.
Table 1
Selected geometric parameters (Å) top
N1—C131.252 (3)N1—C121.454 (2)
Acknowledgements top

The authors thank Professor Hua-Qin Wang, Analysis Centre, Nanjing University, for carrying out the X-ray crystallographic analysis.

references
References top

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.

Enraf–Nonius (1989). CAD-4 Software. Version 5.0. Enraf–Nonius, Delft, The Netherlands.

Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.

Nishikawa, A., Koyama, T., Asano, H. & Narahara, T. (1992). US Patent No. 5 166 283.

North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.

Sharaby, C. M. (2007). Spectrochim. Acta Part A, 66, 1271–1278.

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