(E)-N-{(E)-2-[(3,5-Dimethylbiphenyl-4-yl)imino]­acenaphthen-1-yl­idene}-2,6-di­methyl-4-phenyl­aniline

Yuan, J.; Xie, X.; Liu, Y.; Miao, C.; Li, J.

doi:10.1107/S1600536811054092

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o210

doi:10.1107/S1600536811054092

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(E)-N-{(E)-2-[(3,5-Dimethylbiphenyl-4-yl)imino]acenaphthen-1-ylidene}-2,6-dimethyl-4-phenylaniline

Jianchao Yuan,^a ^* Xiaoli Xie,^a Yufeng Liu,^a Chengping Miao ^a and Jing Li ^a

^aKey Laboratory of Eco-Environment-Related Polymer Materials of the Ministry of Education, Key Laboratory of Polymer Materials of Gansu Province, College of Chemistry & Chemical Engineering, Northwest Normal University, Lanzhou 730070, People's Republic of China
^*Correspondence e-mail: jianchaoyuan@nwnu.edu.cn

(Received 14 November 2011; accepted 15 December 2011; online 21 December 2011)

The title compound, C₄₀H₃₂N₂, has crystallographic twofold rotation symmetry, with two C atoms lying on the axis. The dihedral angle between the two benzene rings of the 4-phenyl-2,6-dimethylphenyl group is 35.74 (17)°. The acenaphthene ring makes an angle of 76.93 (11)° with the benzene ring bonded to the N atom and an angle of 41.53 (13)° with the other benzene ring.

Related literature

The title compound was synthesized as an α-diimine ligand for use in Ni^II–α-diimine olefin polymerization catalysts. For applications of metal-organic polymerization catalysts, see: Johnson et al. (1995 ); Killian et al. (1996 ); Popeney et al. (2005 , 2010 , 2011 ). For a related structure, see: Lohr et al. (2011 ).

Experimental

Crystal data

C₄₀H₃₂N₂
M_r = 540.68
Monoclinic, C 2/c
a = 22.994 (14) Å
b = 8.676 (5) Å
c = 18.652 (18) Å
β = 124.084 (4)°
V = 3082 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 296 K
0.23 × 0.21 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ) T_min = 0.985, T_max = 0.987
10667 measured reflections
2857 independent reflections
1596 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.211
S = 1.16
2857 reflections
193 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b); molecular graphics: SHELXTL (Sheldrick, 2008b); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811054092/fy2034sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811054092/fy2034Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811054092/fy2034Isup3.cml

checkCIF report

Comment top

In recent years, α-diimine nickel catalysts have drawn wide-spread attention due to their high catalytic activity in ethylene polymerization (Johnson et al., 1995; Killian et al., 1996). It is well known that the ligand structure has significant influence on the product properties and polymerization activities (Popeney et al., 2011; Popeney et al., 2010; Popeney et al., 2005). In this study, we designed and synthesized the title compound as a bidentate ligand, and its molecular structure was characterized by X-ray diffraction.

Related literature top

The title compound was synthesized as an α-diimine ligand for use in Ni^II–α-diimine olefin polymerization catalysts. For applications of metal-organic polymerization catalysts, see: Johnson et al. (1995); Killian et al. (1996); Popeney et al. (2005, 2010, 2011). For a related structure, see: Lohr et al. (2011).

Experimental top

Formic acid (1 ml) was added to a stirred solution of acenaphthenequinone (0.25 g, 1.37 mmol) and 4-phenyl-2,6-dimehylaniline (0.54 g, 2.74 mmol) in methanol (20 ml). The mixture was refluxed for 24 h, then cooled and the precipitate was separated by filtration. The solid was recrystallized from ethanol/dichloromethane (v/v = 8:1), washed and dried under vacuum. Yield: 0.55 g (74%). Anal. Calcd. for C₄₀H₃₂N₂: C, 88.85; H, 5.97; N, 5.18. Found: C, 88.91; H, 6.03; N, 5.06. Crystals suitable for X-ray structure determination were grown from a solution of the title compound in a mixture of cyclohexane/dichloromethane (1:2, v/v) by slow evaporation.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b); molecular graphics: SHELXTL (Sheldrick, 2008b); software used to prepare material for publication: SHELXTL (Sheldrick, 2008b).

Figures top

Fig. 1. Structure of the title compound, with displacement ellipsoids drawn at the 30% probability level. H-atoms have been excluded for clarity. The atom name suffix indicates symmetry code (a): –x, y, –z + 1/2.

(E)-N-{(E)-2-[(3,5-Dimethylbiphenyl-4- yl)imino]acenaphthen-1-ylidene}-2,6-dimethyl-4-phenylaniline top

Crystal data top

C₄₀H₃₂N₂	F(000) = 1144
M_r = 540.68	D_x = 1.165 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 22.994 (14) Å	Cell parameters from 3073 reflections
b = 8.676 (5) Å	θ = 2.1–25.7°
c = 18.652 (18) Å	µ = 0.07 mm⁻¹
β = 124.084 (4)°	T = 296 K
V = 3082 (4) Å³	Block, red
Z = 4	0.23 × 0.21 × 0.19 mm

Data collection top

Bruker APEXII CCD diffractometer	2857 independent reflections
Radiation source: fine-focus sealed tube	1596 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	h = −27→27
T_min = 0.985, T_max = 0.987	k = −10→10
10667 measured reflections	l = −22→20

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.211	H-atom parameters constrained
S = 1.16	w = 1/[σ²(F_o²) + (0.0705P)² + 3.4006P] where P = (F_o² + 2F_c²)/3
2857 reflections	(Δ/σ)_max < 0.001
193 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₄₀H₃₂N₂	V = 3082 (4) Å³
M_r = 540.68	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 22.994 (14) Å	µ = 0.07 mm⁻¹
b = 8.676 (5) Å	T = 296 K
c = 18.652 (18) Å	0.23 × 0.21 × 0.19 mm
β = 124.084 (4)°

Data collection top

Bruker APEXII CCD diffractometer	2857 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	1596 reflections with I > 2σ(I)
T_min = 0.985, T_max = 0.987	R_int = 0.031
10667 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.211	H-atom parameters constrained
S = 1.16	Δρ_max = 0.23 e Å⁻³
2857 reflections	Δρ_min = −0.20 e Å⁻³
193 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
C1	0.2760 (2)	0.8437 (6)	0.7549 (2)	0.1024 (15)
H1	0.2411	0.7699	0.7368	0.123*
C2	0.3295 (3)	0.8543 (8)	0.8419 (3)	0.132 (2)
H2	0.3303	0.7877	0.8815	0.159*
C3	0.3807 (3)	0.9614 (9)	0.8696 (3)	0.135 (3)
H3	0.4158	0.9705	0.9283	0.162*
C4	0.3807 (2)	1.0559 (8)	0.8112 (4)	0.126 (2)
H4	0.4165	1.1278	0.8300	0.151*
C5	0.3271 (2)	1.0452 (6)	0.7229 (3)	0.1089 (16)
H5	0.3277	1.1089	0.6832	0.131*
C6	0.27359 (18)	0.9396 (5)	0.6951 (2)	0.0804 (11)
C7	0.21565 (18)	0.9254 (4)	0.6012 (2)	0.0691 (9)
C8	0.22787 (19)	0.9461 (4)	0.5373 (2)	0.0719 (10)
H8	0.2729	0.9726	0.5534	0.086*
C9	0.1758 (2)	0.9289 (4)	0.4504 (2)	0.0707 (10)
C10	0.10860 (19)	0.8859 (3)	0.42739 (19)	0.0639 (9)
C11	0.09402 (17)	0.8687 (4)	0.4894 (2)	0.0668 (9)
C12	0.14776 (18)	0.8885 (4)	0.5757 (2)	0.0720 (10)
H12	0.1382	0.8768	0.6177	0.086*
C13	0.02861 (17)	0.7530 (3)	0.29823 (18)	0.0617 (9)
C14	0.04351 (15)	0.5886 (3)	0.32523 (18)	0.0526 (8)
C15	0.0000	0.5015 (4)	0.2500	0.0497 (10)
C16	0.0000	0.3396 (5)	0.2500	0.0642 (12)
C17	0.0457 (2)	0.2681 (4)	0.3300 (2)	0.0833 (12)
H17	0.0476	0.1610	0.3334	0.100*
C18	0.08782 (19)	0.3537 (4)	0.4034 (2)	0.0753 (10)
H18	0.1177	0.3028	0.4555	0.090*
C19	0.08738 (16)	0.5154 (3)	0.4025 (2)	0.0619 (9)
H19	0.1162	0.5712	0.4532	0.074*
C20	0.1907 (3)	0.9524 (5)	0.3822 (2)	0.1042 (15)
H20A	0.2376	0.9908	0.4088	0.156*
H20B	0.1579	1.0253	0.3402	0.156*
H20C	0.1861	0.8559	0.3542	0.156*
C21	0.02117 (19)	0.8275 (5)	0.4649 (3)	0.0984 (14)
H21A	−0.0123	0.8974	0.4212	0.148*
H21B	0.0194	0.8350	0.5151	0.148*
H21C	0.0101	0.7240	0.4430	0.148*
N1	0.05454 (16)	0.8787 (3)	0.33777 (16)	0.0755 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.081 (3)	0.157 (4)	0.056 (2)	0.001 (3)	0.030 (2)	−0.013 (3)
C2	0.095 (3)	0.217 (7)	0.060 (3)	0.012 (4)	0.028 (3)	−0.017 (3)
C3	0.071 (3)	0.239 (7)	0.071 (3)	0.023 (4)	0.025 (3)	−0.055 (4)
C4	0.070 (3)	0.205 (6)	0.098 (4)	−0.027 (3)	0.044 (3)	−0.082 (4)
C5	0.080 (3)	0.158 (5)	0.082 (3)	−0.031 (3)	0.041 (2)	−0.059 (3)
C6	0.064 (2)	0.113 (3)	0.060 (2)	−0.005 (2)	0.0321 (19)	−0.030 (2)
C7	0.070 (2)	0.074 (2)	0.054 (2)	−0.0068 (17)	0.0291 (18)	−0.0192 (17)
C8	0.077 (2)	0.070 (2)	0.063 (2)	−0.0172 (18)	0.0356 (19)	−0.0174 (17)
C9	0.095 (3)	0.0485 (18)	0.058 (2)	−0.0117 (18)	0.036 (2)	−0.0076 (15)
C10	0.084 (2)	0.0305 (15)	0.0465 (19)	0.0000 (15)	0.0174 (18)	−0.0051 (12)
C11	0.063 (2)	0.0528 (19)	0.060 (2)	−0.0019 (15)	0.0198 (17)	−0.0129 (15)
C12	0.067 (2)	0.082 (2)	0.059 (2)	−0.0036 (18)	0.0293 (18)	−0.0152 (17)
C13	0.080 (2)	0.0283 (15)	0.0504 (17)	−0.0004 (14)	0.0208 (16)	−0.0002 (12)
C14	0.0646 (18)	0.0322 (15)	0.0498 (17)	0.0021 (13)	0.0252 (15)	0.0007 (12)
C15	0.063 (2)	0.0282 (19)	0.051 (2)	0.000	0.027 (2)	0.000
C16	0.078 (3)	0.036 (2)	0.064 (3)	0.000	0.031 (3)	0.000
C17	0.102 (3)	0.0344 (17)	0.087 (3)	0.0073 (17)	0.036 (2)	0.0108 (17)
C18	0.086 (2)	0.050 (2)	0.065 (2)	0.0111 (17)	0.0268 (19)	0.0197 (17)
C19	0.073 (2)	0.0420 (17)	0.0547 (19)	0.0052 (15)	0.0257 (17)	0.0054 (14)
C20	0.145 (4)	0.091 (3)	0.073 (3)	−0.020 (3)	0.059 (3)	0.001 (2)
C21	0.067 (2)	0.105 (3)	0.091 (3)	−0.003 (2)	0.025 (2)	−0.028 (2)
N1	0.100 (2)	0.0295 (13)	0.0510 (16)	−0.0021 (13)	0.0140 (15)	−0.0045 (11)

Geometric parameters (Å, º) top

C1—C6	1.368 (6)	C12—H12	0.9300
C1—C2	1.386 (6)	C13—N1	1.263 (4)
C1—H1	0.9300	C13—C14	1.487 (4)
C2—C3	1.355 (8)	C13—C13ⁱ	1.522 (6)
C2—H2	0.9300	C14—C19	1.368 (4)
C3—C4	1.363 (8)	C14—C15	1.403 (3)
C3—H3	0.9300	C15—C14ⁱ	1.403 (3)
C4—C5	1.402 (6)	C15—C16	1.404 (6)
C4—H4	0.9300	C16—C17ⁱ	1.400 (4)
C5—C6	1.381 (6)	C16—C17	1.400 (4)
C5—H5	0.9300	C17—C18	1.370 (5)
C6—C7	1.497 (5)	C17—H17	0.9300
C7—C8	1.381 (5)	C18—C19	1.403 (4)
C7—C12	1.391 (5)	C18—H18	0.9300
C8—C9	1.382 (4)	C19—H19	0.9300
C8—H8	0.9300	C20—H20A	0.9600
C9—C10	1.404 (5)	C20—H20B	0.9600
C9—C20	1.504 (5)	C20—H20C	0.9600
C10—C11	1.381 (5)	C21—H21A	0.9600
C10—N1	1.419 (4)	C21—H21B	0.9600
C11—C12	1.385 (4)	C21—H21C	0.9600
C11—C21	1.512 (5)

C6—C1—C2	121.2 (5)	C7—C12—H12	119.2
C6—C1—H1	119.4	N1—C13—C14	133.3 (3)
C2—C1—H1	119.4	N1—C13—C13ⁱ	120.18 (17)
C3—C2—C1	120.3 (6)	C14—C13—C13ⁱ	106.44 (15)
C3—C2—H2	119.9	C19—C14—C15	119.7 (3)
C1—C2—H2	119.9	C19—C14—C13	134.2 (3)
C2—C3—C4	119.8 (5)	C15—C14—C13	106.2 (2)
C2—C3—H3	120.1	C14ⁱ—C15—C14	114.8 (3)
C4—C3—H3	120.1	C14ⁱ—C15—C16	122.62 (17)
C3—C4—C5	120.4 (5)	C14—C15—C16	122.62 (17)
C3—C4—H4	119.8	C17ⁱ—C16—C17	127.3 (4)
C5—C4—H4	119.8	C17ⁱ—C16—C15	116.3 (2)
C6—C5—C4	119.8 (5)	C17—C16—C15	116.3 (2)
C6—C5—H5	120.1	C18—C17—C16	120.8 (3)
C4—C5—H5	120.1	C18—C17—H17	119.6
C1—C6—C5	118.5 (4)	C16—C17—H17	119.6
C1—C6—C7	120.4 (4)	C17—C18—C19	122.3 (3)
C5—C6—C7	121.1 (4)	C17—C18—H18	118.8
C8—C7—C12	117.9 (3)	C19—C18—H18	118.8
C8—C7—C6	121.4 (3)	C14—C19—C18	118.2 (3)
C12—C7—C6	120.8 (3)	C14—C19—H19	120.9
C9—C8—C7	122.5 (3)	C18—C19—H19	120.9
C9—C8—H8	118.7	C9—C20—H20A	109.5
C7—C8—H8	118.7	C9—C20—H20B	109.5
C8—C9—C10	117.9 (3)	H20A—C20—H20B	109.5
C8—C9—C20	121.3 (4)	C9—C20—H20C	109.5
C10—C9—C20	120.8 (3)	H20A—C20—H20C	109.5
C11—C10—C9	121.0 (3)	H20B—C20—H20C	109.5
C11—C10—N1	121.2 (3)	C11—C21—H21A	109.5
C9—C10—N1	117.3 (3)	C11—C21—H21B	109.5
C10—C11—C12	118.9 (3)	H21A—C21—H21B	109.5
C10—C11—C21	121.4 (3)	C11—C21—H21C	109.5
C12—C11—C21	119.7 (4)	H21A—C21—H21C	109.5
C11—C12—C7	121.7 (3)	H21B—C21—H21C	109.5
C11—C12—H12	119.2	C13—N1—C10	122.7 (2)

C6—C1—C2—C3	0.3 (8)	C21—C11—C12—C7	179.6 (3)
C1—C2—C3—C4	−2.0 (8)	C8—C7—C12—C11	1.7 (5)
C2—C3—C4—C5	1.5 (8)	C6—C7—C12—C11	−177.3 (3)
C3—C4—C5—C6	0.8 (7)	N1—C13—C14—C19	4.2 (7)
C2—C1—C6—C5	2.0 (7)	C13ⁱ—C13—C14—C19	−178.1 (4)
C2—C1—C6—C7	179.5 (4)	N1—C13—C14—C15	−176.1 (4)
C4—C5—C6—C1	−2.5 (6)	C13ⁱ—C13—C14—C15	1.6 (4)
C4—C5—C6—C7	180.0 (4)	C19—C14—C15—C14ⁱ	179.1 (3)
C1—C6—C7—C8	−142.6 (4)	C13—C14—C15—C14ⁱ	−0.65 (17)
C5—C6—C7—C8	34.9 (5)	C19—C14—C15—C16	−0.9 (3)
C1—C6—C7—C12	36.4 (5)	C13—C14—C15—C16	179.35 (17)
C5—C6—C7—C12	−146.1 (4)	C14ⁱ—C15—C16—C17ⁱ	0.5 (2)
C12—C7—C8—C9	−1.1 (5)	C14—C15—C16—C17ⁱ	−179.5 (2)
C6—C7—C8—C9	177.9 (3)	C14ⁱ—C15—C16—C17	−179.5 (2)
C7—C8—C9—C10	−1.3 (5)	C14—C15—C16—C17	0.5 (2)
C7—C8—C9—C20	179.9 (3)	C17ⁱ—C16—C17—C18	179.8 (4)
C8—C9—C10—C11	3.2 (5)	C15—C16—C17—C18	−0.2 (4)
C20—C9—C10—C11	−178.0 (3)	C16—C17—C18—C19	0.1 (6)
C8—C9—C10—N1	175.9 (3)	C15—C14—C19—C18	0.8 (5)
C20—C9—C10—N1	−5.3 (5)	C13—C14—C19—C18	−179.5 (4)
C9—C10—C11—C12	−2.7 (5)	C17—C18—C19—C14	−0.5 (6)
N1—C10—C11—C12	−175.1 (3)	C14—C13—N1—C10	−1.7 (7)
C9—C10—C11—C21	177.9 (3)	C13ⁱ—C13—N1—C10	−179.2 (4)
N1—C10—C11—C21	5.5 (5)	C11—C10—N1—C13	−78.7 (5)
C10—C11—C12—C7	0.2 (5)	C9—C10—N1—C13	108.6 (4)

Symmetry code: (i) −x, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₄₀H₃₂N₂
M_r	540.68
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	22.994 (14), 8.676 (5), 18.652 (18)
β (°)	124.084 (4)
V (Å³)	3082 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.23 × 0.21 × 0.19

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2008a)
T_min, T_max	0.985, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	10667, 2857, 1596
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.211, 1.16
No. of reflections	2857
No. of parameters	193
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.20

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008b), SHELXL97 (Sheldrick, 2008b), SHELXTL (Sheldrick, 2008b).

Acknowledgements

We thank the National Natural Science Foundation of China (20964003) for funding. We also thank the Key Laboratory of Eco Environment-Related Polymer Materials of the Ministry of Education, Key Laboratory of Polymer Materials of Gansu Province (Northwest Normal University), for financial support.

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