2,3-Bis[(3-methyl-biphenyl-4-yl)imino]-butane.

The title compound, C30H28N2, is a product of the condensation reaction of 2-methyl-4-phenyl-aniline and butane-2,3-dione. The mol-ecule lies on a crystallographic inversion centre. The C=N bond has an E conformation. The dihedral angle between the two benzene rings of the 4-phenyl-2-methyl-phenyl group is 29.19 (76)°. The 1,4-di-aza-butadiene plane makes an angle of 70.1 (10)° with the N-bonded methyl-phenyl ring and an angle of 81.08 (97)° with the terminal phenyl group.

Related literature

The title compound was synthesized as an α-di­imine ligand for applications in olefin polymerization Ni(II)-α-di­imine catalysts, see: Johnson et al. (1995 ▶); Killian et al. (1996 ▶); Wang et al. (2013 ▶); Ionkin & Marshall (2004 ▶); Meinhard et al. (2007 ▶). For the effect of the ligand structure on the activity of the catalyst and the properties of the products, see: Popeney & Guan (2005 ▶); Yuan et al. (2005 ▶); Helldörfer et al. (2003 ▶). For related structures, see: Yuan et al. (2013 ▶).

Experimental

Crystal data

C30H28N2

M = 416.54

Orthorhombic,

a = 8.347 (3) Å

b = 7.063 (3) Å

c = 39.946 (16) Å

V = 2355.0 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 293 K

0.19 × 0.18 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.987, T max = 0.990

15668 measured reflections

2200 independent reflections

1251 reflections with I > 2σ(I)

R int = 0.088

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.135

S = 1.01

2200 reflections

148 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.16 e Å−3

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

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814005686/fk2080sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814005686/fk2080Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814005686/fk2080Isup3.cml

CCDC reference: 991458

Additional supporting information: crystallographic information; 3D view; checkCIF report

C30H28N2	Dx = 1.175 Mg m−3
Mr = 416.54	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 1674 reflections
a = 8.347 (3) Å	θ = 2.6–21.7°
b = 7.063 (3) Å	µ = 0.07 mm−1
c = 39.946 (16) Å	T = 293 K
V = 2355.0 (16) Å3	Block, yellow
Z = 4	0.19 × 0.18 × 0.15 mm
F(000) = 888

Bruker APEXII CCD diffractometer	2200 independent reflections
Radiation source: fine-focus sealed tube	1251 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.088
φ and ω scans	θmax = 25.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −10→10
Tmin = 0.987, Tmax = 0.990	k = −8→8
15668 measured reflections	l = −48→47

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.069	H-atom parameters constrained
wR(F2) = 0.135	w = 1/[σ2(Fo2) + (0.0366P)2 + 1.4273P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
2200 reflections	Δρmax = 0.15 e Å−3
148 parameters	Δρmin = −0.16 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0025 (6)

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	0.6218 (4)	−0.0240 (5)	0.17712 (7)	0.0644 (9)
H1	0.7117	−0.0468	0.1640	0.077*
C2	0.6029 (4)	−0.1219 (5)	0.20680 (8)	0.0716 (10)
H2	0.6792	−0.2106	0.2133	0.086*
C3	0.4725 (4)	−0.0893 (5)	0.22677 (7)	0.0663 (9)
H3	0.4597	−0.1548	0.2468	0.080*
C4	0.3612 (4)	0.0413 (4)	0.21680 (7)	0.0594 (9)
H4	0.2726	0.0652	0.2303	0.071*
C5	0.3788 (4)	0.1375 (4)	0.18713 (6)	0.0504 (8)
H5	0.3012	0.2248	0.1807	0.061*
C6	0.5099 (3)	0.1070 (4)	0.16654 (6)	0.0442 (7)
C7	0.5276 (3)	0.2107 (4)	0.13451 (6)	0.0425 (7)
C8	0.6072 (3)	0.1298 (4)	0.10744 (7)	0.0509 (8)
H8	0.6563	0.0124	0.1099	0.061*
C9	0.6142 (3)	0.2216 (4)	0.07704 (7)	0.0532 (8)
H9	0.6678	0.1652	0.0592	0.064*
C10	0.5427 (3)	0.3961 (4)	0.07266 (6)	0.0423 (7)
C11	0.4688 (3)	0.4856 (4)	0.09956 (6)	0.0432 (7)
C12	0.4629 (3)	0.3887 (4)	0.12980 (6)	0.0443 (7)
H12	0.4126	0.4468	0.1479	0.053*
C13	0.3949 (4)	0.6774 (4)	0.09594 (8)	0.0674 (10)
H13A	0.2882	0.6648	0.0873	0.101*
H13B	0.4580	0.7522	0.0808	0.101*
H13C	0.3912	0.7384	0.1174	0.101*
C14	0.4850 (3)	0.4425 (4)	0.01552 (6)	0.0440 (7)
C15	0.3729 (4)	0.2792 (5)	0.01278 (8)	0.0773 (11)
H15A	0.3722	0.2102	0.0335	0.116*
H15B	0.4073	0.1972	−0.0050	0.116*
H15C	0.2670	0.3248	0.0081	0.116*
N1	0.5572 (3)	0.4954 (3)	0.04174 (5)	0.0486 (6)

	U11	U22	U33	U12	U13	U23
C1	0.068 (2)	0.078 (3)	0.0472 (19)	0.013 (2)	0.0012 (16)	0.0083 (18)
C2	0.086 (3)	0.075 (2)	0.054 (2)	0.016 (2)	−0.0096 (19)	0.012 (2)
C3	0.092 (3)	0.064 (2)	0.0429 (18)	−0.005 (2)	−0.0080 (19)	0.0083 (17)
C4	0.075 (2)	0.063 (2)	0.0400 (17)	−0.0046 (19)	0.0066 (16)	−0.0005 (16)
C5	0.0651 (19)	0.0476 (19)	0.0386 (17)	−0.0013 (16)	0.0034 (14)	0.0006 (15)
C6	0.0502 (17)	0.0475 (18)	0.0349 (15)	0.0018 (15)	−0.0037 (13)	−0.0025 (14)
C7	0.0388 (15)	0.0504 (19)	0.0381 (16)	−0.0011 (15)	−0.0014 (13)	−0.0022 (14)
C8	0.0587 (18)	0.0529 (19)	0.0410 (17)	0.0119 (16)	0.0057 (14)	0.0047 (16)
C9	0.0593 (18)	0.058 (2)	0.0424 (18)	0.0049 (17)	0.0088 (15)	−0.0019 (16)
C10	0.0417 (15)	0.0495 (18)	0.0356 (16)	−0.0052 (15)	−0.0010 (13)	0.0013 (14)
C11	0.0430 (15)	0.0456 (17)	0.0410 (17)	−0.0007 (14)	−0.0023 (13)	−0.0011 (14)
C12	0.0474 (16)	0.0479 (18)	0.0377 (16)	0.0014 (15)	0.0034 (13)	−0.0058 (14)
C13	0.088 (2)	0.055 (2)	0.059 (2)	0.0099 (19)	0.0034 (18)	0.0063 (17)
C14	0.0404 (15)	0.0522 (19)	0.0395 (16)	−0.0047 (14)	0.0022 (13)	0.0024 (13)
C15	0.090 (2)	0.086 (3)	0.055 (2)	−0.041 (2)	−0.0109 (19)	0.0185 (19)
N1	0.0521 (14)	0.0561 (16)	0.0375 (13)	−0.0075 (12)	0.0012 (12)	0.0028 (12)

C1—C6	1.381 (4)	C9—C10	1.380 (4)
C1—C2	1.382 (4)	C9—H9	0.9300
C1—H1	0.9300	C10—C11	1.391 (3)
C2—C3	1.369 (4)	C10—N1	1.426 (3)
C2—H2	0.9300	C11—C12	1.389 (3)
C3—C4	1.368 (4)	C11—C13	1.496 (4)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.374 (4)	C13—H13A	0.9600
C4—H4	0.9300	C13—H13B	0.9600
C5—C6	1.386 (4)	C13—H13C	0.9600
C5—H5	0.9300	C14—N1	1.265 (3)
C6—C7	1.481 (4)	C14—C15	1.489 (4)
C7—C12	1.381 (4)	C14—C14i	1.504 (5)
C7—C8	1.392 (3)	C15—H15A	0.9600
C8—C9	1.378 (4)	C15—H15B	0.9600
C8—H8	0.9300	C15—H15C	0.9600
C6—C1—C2	121.4 (3)	C8—C9—H9	119.6
C6—C1—H1	119.3	C9—C10—C11	120.0 (3)
C2—C1—H1	119.3	C9—C10—N1	120.8 (2)
C3—C2—C1	120.4 (3)	C11—C10—N1	118.9 (3)
C3—C2—H2	119.8	C10—C11—C12	117.6 (3)
C1—C2—H2	119.8	C10—C11—C13	121.3 (3)
C4—C3—C2	118.9 (3)	C12—C11—C13	121.1 (3)
C4—C3—H3	120.5	C7—C12—C11	123.6 (3)
C2—C3—H3	120.5	C7—C12—H12	118.2
C3—C4—C5	120.8 (3)	C11—C12—H12	118.2
C3—C4—H4	119.6	C11—C13—H13A	109.5
C5—C4—H4	119.6	C11—C13—H13B	109.5
C4—C5—C6	121.3 (3)	H13A—C13—H13B	109.5
C4—C5—H5	119.4	C11—C13—H13C	109.5
C6—C5—H5	119.4	H13A—C13—H13C	109.5
C1—C6—C5	117.2 (3)	H13B—C13—H13C	109.5
C1—C6—C7	121.9 (3)	N1—C14—C15	126.1 (3)
C5—C6—C7	120.9 (3)	N1—C14—C14i	116.4 (3)
C12—C7—C8	117.0 (3)	C15—C14—C14i	117.5 (3)
C12—C7—C6	121.9 (3)	C14—C15—H15A	109.5
C8—C7—C6	121.1 (3)	C14—C15—H15B	109.5
C9—C8—C7	120.8 (3)	H15A—C15—H15B	109.5
C9—C8—H8	119.6	C14—C15—H15C	109.5
C7—C8—H8	119.6	H15A—C15—H15C	109.5
C10—C9—C8	120.9 (3)	H15B—C15—H15C	109.5
C10—C9—H9	119.6	C14—N1—C10	122.1 (2)
C6—C1—C2—C3	−0.8 (5)	C8—C9—C10—C11	3.0 (4)
C1—C2—C3—C4	0.2 (5)	C8—C9—C10—N1	176.7 (3)
C2—C3—C4—C5	0.5 (5)	C9—C10—C11—C12	−3.4 (4)
C3—C4—C5—C6	−0.6 (5)	N1—C10—C11—C12	−177.2 (2)
C2—C1—C6—C5	0.7 (5)	C9—C10—C11—C13	178.0 (3)
C2—C1—C6—C7	−179.0 (3)	N1—C10—C11—C13	4.2 (4)
C4—C5—C6—C1	0.0 (4)	C8—C7—C12—C11	2.3 (4)
C4—C5—C6—C7	179.7 (3)	C6—C7—C12—C11	−176.1 (3)
C1—C6—C7—C12	−152.1 (3)	C10—C11—C12—C7	0.7 (4)
C5—C6—C7—C12	28.3 (4)	C13—C11—C12—C7	179.4 (3)
C1—C6—C7—C8	29.6 (4)	C15—C14—N1—C10	2.3 (5)
C5—C6—C7—C8	−150.0 (3)	C14i—C14—N1—C10	−178.4 (3)
C12—C7—C8—C9	−2.7 (4)	C9—C10—N1—C14	71.9 (4)
C6—C7—C8—C9	175.7 (3)	C11—C10—N1—C14	−114.4 (3)
C7—C8—C9—C10	0.1 (4)