Crystal structure of 2,3-bis-[(4-tert-butyl-2,6-di-methyl-phen-yl)imino]-butane.

The title compound, C28H40N2, was obtained from the condensation reaction of 4-tert-butyl-2,6-di-methyl-aniline and butane-2,3-dione. The mol-ecule lies on an inversion centre. The C=N bond has an E conformation. The plane of the benzene ring is almost perpendicular to the 1,4-di-aza-butadiene mean plane [dihedral angle = 89.8 (9)°].

Related literature

The title compound was synthesized as an α-di­imine ligand for applications in olefin polymerization NiII–α-di­imine catalysts, see: Cotts et al. (2000 ▸); Johnson et al.(1995 ▸); Ittel et al. (2000 ▸); Mecking et al. (1998 ▸) . For the effect of the ligand structure on the activity of the catalyst and the properties of the products, see: Gates et al. (2000 ▸); Meinhard et al. (2007 ▸); For related structures, see: Yuan et al. (2005 ▸).

Experimental

Crystal data

C28H40N2

M = 404.62

Triclinic,

a = 5.993 (6) Å

b = 10.064 (9) Å

c = 11.614 (11) Å

α = 107.913 (9)°

β = 100.484 (10)°

γ = 99.260 (9)°

V = 637.5 (10) Å3

Z = 1

Mo Kα radiation

μ = 0.06 mm−1

T = 296 K

0.23 × 0.21 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▸) T min = 0.986, T max = 0.989

4557 measured reflections

2310 independent reflections

1348 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.102

wR(F 2) = 0.220

S = 1.05

2310 reflections

142 parameters

42 restraints

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.21 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/S2056989015005551/xu5841sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015005551/xu5841Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015005551/xu5841Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015005551/xu5841fig1.tif

Mol­ecular structure of the title compound, using 30% probability level ellipsoids (the hydrogens have been omitted for clarity). Primed atoms are related by the symmetry code (-x+1, −y+2, −z+1).

Click here for additional data file.

tert . . DOI: 10.1107/S2056989015005551/xu5841fig2.tif

Synthesis of 2,3-bis­{[4-(tert-but­yl)-2,6-dimeth­yl]imino}­butane.

CCDC reference: 1054707

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

C28H40N2	Z = 1
Mr = 404.62	F(000) = 222
Triclinic, P1	Dx = 1.054 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.993 (6) Å	Cell parameters from 1229 reflections
b = 10.064 (9) Å	θ = 2.4–28.3°
c = 11.614 (11) Å	µ = 0.06 mm−1
α = 107.913 (9)°	T = 296 K
β = 100.484 (10)°	Block, yellow
γ = 99.260 (9)°	0.23 × 0.21 × 0.18 mm
V = 637.5 (10) Å3

Bruker APEXII CCD diffractometer	2310 independent reflections
Radiation source: fine-focus sealed tube	1348 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −7→7
Tmin = 0.986, Tmax = 0.989	k = −12→11
4557 measured reflections	l = −14→13

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)] = 0.102	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.220	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.040P)2 + 1.2419P] where P = (Fo2 + 2Fc2)/3
2310 reflections	(Δ/σ)max < 0.001
142 parameters	Δρmax = 0.52 e Å−3
42 restraints	Δρmin = −0.21 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	0.4381 (7)	0.6834 (4)	0.3770 (4)	0.0394 (10)
C2	0.2730 (7)	0.6166 (4)	0.2638 (4)	0.0434 (11)
C3	0.2889 (7)	0.4854 (4)	0.1863 (4)	0.0439 (11)
H3	0.1786	0.4407	0.1104	0.053*
C4	0.4620 (7)	0.4180 (4)	0.2170 (4)	0.0413 (11)
C5	0.6199 (8)	0.4869 (4)	0.3302 (4)	0.0466 (11)
H5	0.7373	0.4430	0.3531	0.056*
C6	0.6132 (8)	0.6185 (4)	0.4121 (4)	0.0431 (11)
C7	0.0812 (9)	0.6857 (5)	0.2255 (5)	0.0642 (15)
H7A	−0.0024	0.7076	0.2894	0.096*
H7B	−0.0239	0.6209	0.1487	0.096*
H7C	0.1475	0.7725	0.2138	0.096*
C8	0.4746 (9)	0.2729 (4)	0.1263 (4)	0.0540 (13)
C9	0.5397 (13)	0.2937 (6)	0.0139 (6)	0.107 (2)
H9A	0.5464	0.2030	−0.0431	0.160*
H9B	0.6895	0.3591	0.0387	0.160*
H9C	0.4250	0.3322	−0.0264	0.160*
C10	0.2528 (12)	0.1679 (6)	0.0939 (8)	0.138 (3)
H10A	0.1292	0.2030	0.0567	0.208*
H10B	0.2225	0.1533	0.1680	0.208*
H10C	0.2614	0.0785	0.0357	0.208*
C11	0.6673 (13)	0.2145 (6)	0.1849 (6)	0.112 (2)
H11A	0.6383	0.2030	0.2603	0.167*
H11B	0.8149	0.2805	0.2039	0.167*
H11C	0.6703	0.1233	0.1274	0.167*
C12	0.7936 (9)	0.6874 (5)	0.5336 (4)	0.0648 (15)
H12A	0.9289	0.7412	0.5211	0.097*
H12B	0.8363	0.6146	0.5645	0.097*
H12C	0.7313	0.7507	0.5930	0.097*
C13	0.5168 (8)	0.9330 (4)	0.4552 (4)	0.0404 (10)
C14	0.6647 (10)	0.9478 (5)	0.3680 (5)	0.0671 (16)
H14A	0.6877	0.8553	0.3238	0.101*
H14B	0.8131	1.0115	0.4145	0.101*
H14C	0.5890	0.9860	0.3095	0.101*
N1	0.4167 (6)	0.8151 (3)	0.4603 (3)	0.0440 (10)

	U11	U22	U33	U12	U13	U23
C1	0.052 (3)	0.026 (2)	0.042 (2)	0.0086 (19)	0.023 (2)	0.0084 (18)
C2	0.050 (3)	0.034 (2)	0.051 (3)	0.016 (2)	0.020 (2)	0.013 (2)
C3	0.047 (3)	0.037 (2)	0.044 (3)	0.010 (2)	0.010 (2)	0.009 (2)
C4	0.049 (3)	0.031 (2)	0.047 (3)	0.010 (2)	0.019 (2)	0.0123 (19)
C5	0.050 (3)	0.037 (2)	0.054 (3)	0.018 (2)	0.013 (2)	0.013 (2)
C6	0.051 (3)	0.036 (2)	0.043 (3)	0.009 (2)	0.013 (2)	0.013 (2)
C7	0.063 (3)	0.053 (3)	0.072 (4)	0.026 (3)	0.012 (3)	0.013 (3)
C8	0.068 (3)	0.033 (2)	0.061 (3)	0.021 (2)	0.029 (2)	0.005 (2)
C9	0.164 (6)	0.077 (4)	0.080 (4)	0.040 (4)	0.058 (4)	0.008 (3)
C10	0.107 (5)	0.049 (3)	0.198 (7)	−0.008 (3)	0.068 (5)	−0.046 (4)
C11	0.148 (6)	0.067 (4)	0.108 (5)	0.068 (4)	0.018 (4)	0.000 (3)
C12	0.072 (4)	0.054 (3)	0.052 (3)	0.012 (3)	−0.002 (3)	0.007 (2)
C13	0.050 (3)	0.032 (2)	0.042 (2)	0.0111 (19)	0.018 (2)	0.0119 (18)
C14	0.102 (4)	0.035 (2)	0.074 (3)	0.017 (3)	0.053 (3)	0.013 (2)
N1	0.057 (2)	0.0297 (19)	0.047 (2)	0.0110 (17)	0.0237 (18)	0.0097 (16)

C1—C2	1.388 (6)	C9—H9A	0.9600
C1—C6	1.386 (6)	C9—H9B	0.9600
C1—N1	1.421 (5)	C9—H9C	0.9600
C2—C3	1.379 (5)	C10—H10A	0.9600
C2—C7	1.505 (6)	C10—H10B	0.9600
C3—C4	1.380 (6)	C10—H10C	0.9600
C3—H3	0.9300	C11—H11A	0.9600
C4—C5	1.372 (6)	C11—H11B	0.9600
C4—C8	1.538 (5)	C11—H11C	0.9600
C5—C6	1.384 (6)	C12—H12A	0.9600
C5—H5	0.9300	C12—H12B	0.9600
C6—C12	1.497 (6)	C12—H12C	0.9600
C7—H7A	0.9600	C13—N1	1.264 (5)
C7—H7B	0.9600	C13—C14	1.486 (6)
C7—H7C	0.9600	C13—C13i	1.497 (7)
C8—C10	1.465 (7)	C14—H14A	0.9600
C8—C9	1.493 (7)	C14—H14B	0.9600
C8—C11	1.523 (7)	C14—H14C	0.9600
C2—C1—C6	120.6 (3)	H9A—C9—H9B	109.5
C2—C1—N1	119.1 (4)	C8—C9—H9C	109.5
C6—C1—N1	120.2 (4)	H9A—C9—H9C	109.5
C1—C2—C3	118.6 (4)	H9B—C9—H9C	109.5
C1—C2—C7	121.0 (4)	C8—C10—H10A	109.5
C3—C2—C7	120.4 (4)	C8—C10—H10B	109.5
C4—C3—C2	122.6 (4)	H10A—C10—H10B	109.5
C4—C3—H3	118.7	C8—C10—H10C	109.5
C2—C3—H3	118.7	H10A—C10—H10C	109.5
C5—C4—C3	116.9 (4)	H10B—C10—H10C	109.5
C5—C4—C8	122.5 (4)	C8—C11—H11A	109.5
C3—C4—C8	120.6 (4)	C8—C11—H11B	109.5
C4—C5—C6	123.2 (4)	H11A—C11—H11B	109.5
C4—C5—H5	118.4	C8—C11—H11C	109.5
C6—C5—H5	118.4	H11A—C11—H11C	109.5
C1—C6—C5	118.0 (4)	H11B—C11—H11C	109.5
C1—C6—C12	122.0 (4)	C6—C12—H12A	109.5
C5—C6—C12	120.0 (4)	C6—C12—H12B	109.5
C2—C7—H7A	109.5	H12A—C12—H12B	109.5
C2—C7—H7B	109.5	C6—C12—H12C	109.5
H7A—C7—H7B	109.5	H12A—C12—H12C	109.5
C2—C7—H7C	109.5	H12B—C12—H12C	109.5
H7A—C7—H7C	109.5	N1—C13—C14	124.9 (4)
H7B—C7—H7C	109.5	N1—C13—C13i	116.8 (5)
C10—C8—C9	112.2 (6)	C14—C13—C13i	118.2 (5)
C10—C8—C11	108.4 (5)	C13—C14—H14A	109.5
C9—C8—C11	105.7 (5)	C13—C14—H14B	109.5
C10—C8—C4	110.2 (4)	H14A—C14—H14B	109.5
C9—C8—C4	109.4 (4)	C13—C14—H14C	109.5
C11—C8—C4	110.9 (4)	H14A—C14—H14C	109.5
C8—C9—H9A	109.5	H14B—C14—H14C	109.5
C8—C9—H9B	109.5	C13—N1—C1	120.1 (3)
C6—C1—C2—C3	−0.9 (6)	N1—C1—C6—C12	−3.9 (6)
N1—C1—C2—C3	−177.0 (4)	C4—C5—C6—C1	−0.2 (6)
C6—C1—C2—C7	179.5 (4)	C4—C5—C6—C12	−179.4 (4)
N1—C1—C2—C7	3.5 (6)	C5—C4—C8—C10	125.0 (6)
C1—C2—C3—C4	0.1 (6)	C3—C4—C8—C10	−55.4 (7)
C7—C2—C3—C4	179.7 (4)	C5—C4—C8—C9	−111.2 (5)
C2—C3—C4—C5	0.6 (6)	C3—C4—C8—C9	68.3 (6)
C2—C3—C4—C8	−179.0 (4)	C5—C4—C8—C11	5.0 (6)
C3—C4—C5—C6	−0.5 (6)	C3—C4—C8—C11	−175.5 (5)
C8—C4—C5—C6	179.0 (4)	C14—C13—N1—C1	−1.2 (7)
C2—C1—C6—C5	0.9 (6)	C13i—C13—N1—C1	179.2 (5)
N1—C1—C6—C5	176.9 (4)	C2—C1—N1—C13	−91.4 (5)
C2—C1—C6—C12	−179.9 (4)	C6—C1—N1—C13	92.6 (5)