N-{(E)-4-[(E)-(Dodecyl-imino)meth-yl]benzyl-idene}dodecan-1-imine.

The title compound, C(32)H(56)N(2), was synthesized by the reaction of terephthalaldehyde and dodecan-1-amine. The imines adopt trans conformations, with the two halves of the mol-ecule 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 = 468.80

Triclinic,

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[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.171

S = 1.06

3020 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.11 e Å−3

Δρmin = −0.12 e Å−3

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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808001463/ez2115sup1.cif

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

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

C32H56N2	Z = 1
Mr = 468.80	F000 = 262
Triclinic, P1	Dx = 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 = 9–13º
α = 91.18 (3)º	µ = 0.06 mm−1
β = 93.44 (3)º	T = 298 (2) K
γ = 101.75 (3)º	Block, colorless
V = 774.1 (3) Å3	0.30 × 0.20 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	Rint = 0.044
Radiation source: fine-focus sealed tube	θmax = 26.0º
Monochromator: graphite	θmin = 1.4º
T = 298(2) K	h = −5→5
ω/2θ scans	k = −6→6
Absorption correction: ψ scan(North et al., 1968)	l = 0→37
Tmin = 0.953, Tmax = 0.964	3 standard reflections
3409 measured reflections	every 200 reflections
3020 independent reflections	intensity decay: none
1271 reflections with I > 2σ(I)

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.065	H-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 reflections	Δρmax = 0.11 e Å−3
154 parameters	Δρmin = −0.12 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

Table 1

Selected bond lengths (Å)

N1—C13	1.252 (3)
N1—C12	1.454 (2)