(E)-N-{(E)-2-[(3,5-Dimethylbiphenyl-4-yl)imino]-acenaphthen-1-yl-idene}-2,6-di-methyl-4-phenyl-aniline.

The title compound, C(40)H(32)N(2), 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-dimethyl-phenyl 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 NiII–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 = 540.68

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.211

S = 1.16

2857 reflections

193 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811054092/fy2034sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811054092/fy2034Isup3.cml

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

C40H32N2	F(000) = 1144
Mr = 540.68	Dx = 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

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

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(Fo2) + (0.0705P)2 + 3.4006P] where P = (Fo2 + 2Fc2)/3
2857 reflections	(Δ/σ)max < 0.001
193 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

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
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)

	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)

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)