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

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

doi:10.1107/S1600536808001463

organic compounds

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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Page o565

doi:10.1107/S1600536808001463

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

Bin Wang,^a Rong Wan,^a ^* Li-He Yin,^a Feng Han ^a and Jin-Tang Wang ^a

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, No. 5 Xinmofan Road, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: rwan@njut.edu.cn

(Received 16 November 2007; accepted 14 January 2008; online 6 February 2008)

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.

Related literature

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

Experimental

Crystal data

C₃₂H₅₆N₂
M_r = 468.80
Triclinic, $[P \overline 1]$
a = 4.7370 (9) Å
b = 5.5190 (11) Å
c = 30.315 (6) Å
α = 91.18 (3)°
β = 93.44 (3)°
γ = 101.75 (3)°
V = 774.1 (3) Å³
Z = 1
Mo Kα radiation
μ = 0.06 mm⁻¹
T = 298 (2) K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.953, T_max = 0.964
3409 measured reflections
3020 independent reflections
1271 reflections with I > 2σ(I)
R_int = 0.044
3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.171
S = 1.06
3020 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.12 e Å⁻³

Table 1
Selected bond lengths (Å)

N1—C13	1.252 (3)
N1—C12	1.454 (2)

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/S1600536808001463/ez2115sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808001463/ez2115Isup2.hkl

checkCIF report

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.

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. 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

C₃₂H₅₆N₂	Z = 1
M_r = 468.80	F(000) = 262
Triclinic, P1	D_x = 1.006 Mg m⁻³
Hall symbol: -P 1	Melting point = 332–333 K
a = 4.7370 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 5.5190 (11) Å	Cell parameters from 25 reflections
c = 30.315 (6) Å	θ = 9–13°
α = 91.18 (3)°	µ = 0.06 mm⁻¹
β = 93.44 (3)°	T = 298 K
γ = 101.75 (3)°	Block, colorless
V = 774.1 (3) Å³	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1271 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.044
Graphite monochromator	θ_max = 26.0°, θ_min = 1.4°
ω/2θ scans	h = −5→5
Absorption correction: ψ scan (North et al., 1968)	k = −6→6
T_min = 0.953, T_max = 0.964	l = 0→37
3409 measured reflections	3 standard reflections every 200 reflections
3020 independent reflections	intensity decay: none

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.171	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.06P)²] where P = (F_o² + 2F_c²)/3
3020 reflections	(Δ/σ)_max < 0.001
154 parameters	Δρ_max = 0.11 e Å⁻³
0 restraints	Δρ_min = −0.12 e Å⁻³

Crystal data top

C₃₂H₅₆N₂	γ = 101.75 (3)°
M_r = 468.80	V = 774.1 (3) Å³
Triclinic, P1	Z = 1
a = 4.7370 (9) Å	Mo Kα radiation
b = 5.5190 (11) Å	µ = 0.06 mm⁻¹
c = 30.315 (6) Å	T = 298 K
α = 91.18 (3)°	0.30 × 0.20 × 0.10 mm
β = 93.44 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1271 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.044
T_min = 0.953, T_max = 0.964	3 standard reflections every 200 reflections
3409 measured reflections	intensity decay: none
3020 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.171	H-atom parameters constrained
S = 1.06	Δρ_max = 0.11 e Å⁻³
3020 reflections	Δρ_min = −0.12 e Å⁻³
154 parameters

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

	x	y	z	U_iso*/U_eq
N1	0.2538 (4)	−0.7333 (4)	0.10048 (7)	0.0778 (7)
C1	0.7923 (7)	1.2784 (5)	0.45915 (9)	0.1139 (11)
H1A	0.6948	1.3606	0.4799	0.171*
H1B	0.8934	1.3977	0.4400	0.171*
H1C	0.9278	1.1985	0.4749	0.171*
C2	0.5752 (6)	1.0886 (5)	0.43217 (9)	0.0957 (9)
H2A	0.4702	0.9734	0.4521	0.115*
H2B	0.4372	1.1718	0.4171	0.115*
C3	0.6950 (5)	0.9444 (4)	0.39859 (8)	0.0776 (7)
H3A	0.8330	0.8612	0.4136	0.093*
H3B	0.8002	1.0596	0.3786	0.093*
C4	0.4773 (5)	0.7540 (4)	0.37145 (8)	0.0748 (7)
H4A	0.3727	0.6382	0.3914	0.090*
H4B	0.3389	0.8370	0.3565	0.090*
C5	0.6000 (5)	0.6097 (4)	0.33745 (7)	0.0698 (7)
H5A	0.7367	0.5248	0.3524	0.084*
H5B	0.7060	0.7252	0.3176	0.084*
C6	0.3788 (5)	0.4215 (4)	0.31028 (7)	0.0683 (7)
H6A	0.2450	0.5068	0.2947	0.082*
H6B	0.2695	0.3084	0.3301	0.082*
C7	0.5035 (5)	0.2726 (4)	0.27696 (7)	0.0672 (7)
H7A	0.6154	0.3861	0.2574	0.081*
H7B	0.6351	0.1855	0.2926	0.081*
C8	0.2832 (5)	0.0869 (4)	0.24921 (7)	0.0665 (7)
H8A	0.1536	0.1742	0.2331	0.080*
H8B	0.1691	−0.0251	0.2687	0.080*
C9	0.4102 (5)	−0.0638 (4)	0.21653 (7)	0.0680 (7)
H9A	0.5357	−0.1544	0.2327	0.082*
H9B	0.5289	0.0487	0.1976	0.082*
C10	0.1910 (5)	−0.2461 (4)	0.18760 (7)	0.0706 (7)
H10A	0.0643	−0.3528	0.2064	0.085*
H10B	0.0734	−0.1553	0.1698	0.085*
C11	0.3247 (5)	−0.4049 (4)	0.15738 (7)	0.0679 (7)
H11A	0.4605	−0.2978	0.1400	0.081*
H11B	0.4328	−0.5029	0.1753	0.081*
C12	0.1100 (5)	−0.5762 (5)	0.12654 (8)	0.0814 (8)
H12A	−0.0327	−0.6788	0.1435	0.098*
H12B	0.0105	−0.4797	0.1069	0.098*
C13	0.2374 (5)	−0.7155 (4)	0.05935 (9)	0.0691 (7)
H13A	0.1336	−0.6041	0.0472	0.083*
C14	0.3736 (5)	−0.8616 (4)	0.02936 (8)	0.0599 (6)
C15	0.5322 (5)	−1.0284 (4)	0.04476 (8)	0.0662 (7)
H15A	0.5576	−1.0479	0.0750	0.079*
C16	0.3458 (5)	−0.8331 (4)	−0.01595 (9)	0.0705 (7)
H16A	0.2430	−0.7184	−0.0270	0.085*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0771 (14)	0.0880 (15)	0.0692 (14)	0.0179 (12)	0.0158 (12)	−0.0196 (12)
C1	0.129 (3)	0.098 (2)	0.105 (2)	0.007 (2)	0.003 (2)	−0.0417 (18)
C2	0.098 (2)	0.0910 (19)	0.092 (2)	0.0058 (17)	0.0204 (17)	−0.0272 (17)
C3	0.0739 (17)	0.0762 (16)	0.0810 (18)	0.0124 (14)	0.0088 (14)	−0.0160 (14)
C4	0.0687 (16)	0.0754 (16)	0.0798 (18)	0.0121 (14)	0.0158 (14)	−0.0155 (14)
C5	0.0625 (15)	0.0703 (15)	0.0782 (17)	0.0153 (13)	0.0171 (13)	−0.0122 (13)
C6	0.0582 (14)	0.0693 (15)	0.0765 (17)	0.0104 (13)	0.0124 (13)	−0.0116 (13)
C7	0.0611 (15)	0.0663 (14)	0.0754 (16)	0.0136 (13)	0.0157 (13)	−0.0104 (12)
C8	0.0625 (15)	0.0688 (14)	0.0696 (16)	0.0153 (13)	0.0137 (13)	−0.0091 (12)
C9	0.0643 (15)	0.0718 (15)	0.0713 (16)	0.0190 (13)	0.0196 (13)	−0.0097 (13)
C10	0.0614 (15)	0.0778 (16)	0.0726 (17)	0.0137 (14)	0.0135 (13)	−0.0134 (13)
C11	0.0690 (16)	0.0721 (15)	0.0657 (16)	0.0187 (13)	0.0189 (13)	−0.0079 (12)
C12	0.0737 (17)	0.0956 (18)	0.0769 (18)	0.0210 (16)	0.0184 (15)	−0.0256 (15)
C13	0.0552 (15)	0.0678 (15)	0.0824 (19)	0.0085 (13)	0.0094 (14)	−0.0150 (14)
C14	0.0494 (14)	0.0552 (14)	0.0723 (17)	0.0034 (12)	0.0120 (13)	−0.0098 (12)
C15	0.0690 (16)	0.0692 (15)	0.0596 (15)	0.0108 (14)	0.0099 (13)	−0.0034 (13)
C16	0.0670 (17)	0.0724 (16)	0.0747 (19)	0.0195 (14)	0.0098 (14)	−0.0049 (14)

Geometric parameters (Å, º) top

N1—C13	1.252 (3)	C7—H7B	0.9700
N1—C12	1.454 (2)	C8—C9	1.509 (2)
C1—C2	1.500 (3)	C8—H8A	0.9700
C1—H1A	0.9600	C8—H8B	0.9700
C1—H1B	0.9600	C9—C10	1.513 (3)
C1—H1C	0.9600	C9—H9A	0.9700
C2—C3	1.487 (3)	C9—H9B	0.9700
C2—H2A	0.9700	C10—C11	1.507 (2)
C2—H2B	0.9700	C10—H10A	0.9700
C3—C4	1.505 (3)	C10—H10B	0.9700
C3—H3A	0.9700	C11—C12	1.503 (3)
C3—H3B	0.9700	C11—H11A	0.9700
C4—C5	1.504 (2)	C11—H11B	0.9700
C4—H4A	0.9700	C12—H12A	0.9700
C4—H4B	0.9700	C12—H12B	0.9700
C5—C6	1.508 (3)	C13—C14	1.464 (3)
C5—H5A	0.9700	C13—H13A	0.9300
C5—H5B	0.9700	C14—C15	1.374 (3)
C6—C7	1.510 (2)	C14—C16	1.387 (3)
C6—H6A	0.9700	C15—C16ⁱ	1.376 (3)
C6—H6B	0.9700	C15—H15A	0.9300
C7—C8	1.507 (3)	C16—C15ⁱ	1.376 (3)
C7—H7A	0.9700	C16—H16A	0.9300

C13—N1—C12	117.7 (2)	C7—C8—C9	114.44 (18)
C2—C1—H1A	109.5	C7—C8—H8A	108.7
C2—C1—H1B	109.5	C9—C8—H8A	108.7
H1A—C1—H1B	109.5	C7—C8—H8B	108.7
C2—C1—H1C	109.5	C9—C8—H8B	108.7
H1A—C1—H1C	109.5	H8A—C8—H8B	107.6
H1B—C1—H1C	109.5	C8—C9—C10	114.96 (18)
C3—C2—C1	115.7 (2)	C8—C9—H9A	108.5
C3—C2—H2A	108.4	C10—C9—H9A	108.5
C1—C2—H2A	108.4	C8—C9—H9B	108.5
C3—C2—H2B	108.4	C10—C9—H9B	108.5
C1—C2—H2B	108.4	H9A—C9—H9B	107.5
H2A—C2—H2B	107.4	C11—C10—C9	113.62 (18)
C2—C3—C4	115.7 (2)	C11—C10—H10A	108.8
C2—C3—H3A	108.3	C9—C10—H10A	108.8
C4—C3—H3A	108.3	C11—C10—H10B	108.8
C2—C3—H3B	108.3	C9—C10—H10B	108.8
C4—C3—H3B	108.3	H10A—C10—H10B	107.7
H3A—C3—H3B	107.4	C12—C11—C10	114.14 (18)
C5—C4—C3	115.43 (18)	C12—C11—H11A	108.7
C5—C4—H4A	108.4	C10—C11—H11A	108.7
C3—C4—H4A	108.4	C12—C11—H11B	108.7
C5—C4—H4B	108.4	C10—C11—H11B	108.7
C3—C4—H4B	108.4	H11A—C11—H11B	107.6
H4A—C4—H4B	107.5	N1—C12—C11	110.77 (19)
C4—C5—C6	114.74 (17)	N1—C12—H12A	109.5
C4—C5—H5A	108.6	C11—C12—H12A	109.5
C6—C5—H5A	108.6	N1—C12—H12B	109.5
C4—C5—H5B	108.6	C11—C12—H12B	109.5
C6—C5—H5B	108.6	H12A—C12—H12B	108.1
H5A—C5—H5B	107.6	N1—C13—C14	123.2 (3)
C5—C6—C7	114.56 (17)	N1—C13—H13A	118.4
C5—C6—H6A	108.6	C14—C13—H13A	118.4
C7—C6—H6A	108.6	C15—C14—C16	118.0 (2)
C5—C6—H6B	108.6	C15—C14—C13	121.8 (2)
C7—C6—H6B	108.6	C16—C14—C13	120.2 (2)
H6A—C6—H6B	107.6	C14—C15—C16ⁱ	120.9 (2)
C8—C7—C6	114.84 (18)	C14—C15—H15A	119.6
C8—C7—H7A	108.6	C16ⁱ—C15—H15A	119.6
C6—C7—H7A	108.6	C15ⁱ—C16—C14	121.1 (2)
C8—C7—H7B	108.6	C15ⁱ—C16—H16A	119.5
C6—C7—H7B	108.6	C14—C16—H16A	119.5
H7A—C7—H7B	107.5

C1—C2—C3—C4	−179.9 (2)	C13—N1—C12—C11	−118.5 (3)
C2—C3—C4—C5	179.8 (2)	C10—C11—C12—N1	−176.5 (2)
C3—C4—C5—C6	−179.4 (2)	C12—N1—C13—C14	179.61 (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—C16	179.8 (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—C16ⁱ	178.85 (19)
C8—C9—C10—C11	−176.34 (19)	C15—C14—C16—C15ⁱ	1.5 (3)
C9—C10—C11—C12	−176.5 (2)	C13—C14—C16—C15ⁱ	−178.85 (19)

Symmetry code: (i) −x+1, −y−2, −z.

Experimental details

Crystal data
Chemical formula	C₃₂H₅₆N₂
M_r	468.80
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	4.7370 (9), 5.5190 (11), 30.315 (6)
α, β, γ (°)	91.18 (3), 93.44 (3), 101.75 (3)
V (Å³)	774.1 (3)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.06
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.953, 0.964
No. of measured, independent and observed [I > 2σ(I)] reflections	3409, 3020, 1271
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.171, 1.06
No. of reflections	3020
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.11, −0.12

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

Selected bond lengths (Å) top

N1—C13

1.252 (3)

N1—C12

1.454 (2)

Acknowledgements

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

References

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