Crystal structure of 2,3-bis­[(4-tert-butyl-2,6-di­methyl­phen­yl)imino]­butane

Zhao, S.-L.; Yuan, J.-C.; Zhao, Y.

doi:10.1107/S2056989015005551

organic compounds

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Volume 71| Part 4| April 2015| Page o258

doi:10.1107/S2056989015005551

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Crystal structure of 2,3-bis[(4-tert-butyl-2,6-dimethylphenyl)imino]butane

Sheng-Lan Zhao,^a Jian-Chao Yuan ^a ^* and Yan Zhao ^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

Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), China (Received 5 March 2015; accepted 18 March 2015; online 25 March 2015)

The title compound, C₂₈H₄₀N₂, was obtained from the condensation reaction of 4-tert-butyl-2,6-dimethylaniline and butane-2,3-dione. The molecule 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-diazabutadiene mean plane [dihedral angle = 89.8 (9)°].

Keywords: crystal structure; α-diimine ligand; catalyst; aniline; diiminobutane.

CCDC reference: 1054707

1. Related literature

The title compound was synthesized as an α-diimine ligand for applications in olefin polymerization Ni^II–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 ).

2. Experimental

2.1. Crystal data

C₂₈H₄₀N₂
M_r = 404.62
Triclinic, $[P \overline 1]$
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

2.2. 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

2.3. Refinement

R[F² > 2σ(F²)] = 0.102
wR(F²) = 0.220
S = 1.05
2310 reflections
142 parameters
42 restraints
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −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.

Supporting information

CCDC reference: 1054707

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S2056989015005551/xu5841sup1.cif

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

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

checkCIF report

Introduction top

Since Brookhart and co-workers discovered Ni^II and Pd^II aryl-substituted α-diimine complexes for olefin polymerization (Cotts et al., 2000; Gates et al., 2000; Johnson et al., 1995; Meinhard et al., 2007; Mecking et al., 1998), late transition metal catalysts have attracted increseaing attention from their high functionality. It is well known that the ligand structure had significant influence on the product properties and polymerization activities (Ittel et al., 2000; Yuan 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. In the crystal structure of the title compound, C₂₈H₄₀N₂, the complete molecule is generated by the application of C₂ symmetry. The single bond of 1,4-diazabutadiene fragment is (E)-configured. The dihedral angle between the benzene ring and 1,4-diazabutadiene plane is 89.8 (9)°.

Synthesis and crystallization top

Formic acid (0.2 ml) was added to a stirred solution of butane-2,3-dione (0.09 g, 1.00 mmol) and 4-(tert-butyl)-2,6-dimethylaniline (0.39 g, 2.2 mmol) in ethanol (10 ml). The mixture was refluxed for 24 h, then cooled and the precipitate was separated by filtration. The solid was recrystallized from MeOH/CH₂Cl₂ (v/v = 10:1), than washed with cold ethanol and dried under vacuum (0.35 g, 87% yield). Anal. Calc. for C₂₈H₄₀N₂: C, 83.11; H, 9.96; N, 6.92. Found: C, 83.23; H, 10.03; N, 6.89.

Refinement top

All hydrogen atoms were placed in calculated positions with C—H distances of 0.93Å and 0.96Å for aryl and methyl H atoms. They were included in the refinement in a riding model approximation, respectively. The H atoms were assigned U_iso = 1.2U_eq(C) for aryl H and U_iso = 1.5U_eq(C) for methyl H.

Results and discussion top

Related literature top

The title compound was synthesized as an α-diimine ligand for applications in olefin polymerization Ni^II–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).

Structure description top

The title compound was synthesized as an α-diimine ligand for applications in olefin polymerization Ni^II–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).

Synthesis and crystallization top

Refinement details top

Computing details top

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

Figures top

	Fig. 1. 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).
	Fig. 2. Synthesis of 2,3-bis{[4-(tert-butyl)-2,6-dimethyl]imino}butane.

4-tert-Butyl-N-{3-[(4-tert-butyl-2,6-dimethylphenyl)imino]butan-2-ylidene}-2,6-dimethylaniline top

Crystal data top

C₂₈H₄₀N₂	Z = 1
M_r = 404.62	F(000) = 222
Triclinic, P1	D_x = 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

Data collection top

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

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)] = 0.102	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.220	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.040P)² + 1.2419P] where P = (F_o² + 2F_c²)/3
2310 reflections	(Δ/σ)_max < 0.001
142 parameters	Δρ_max = 0.52 e Å⁻³
42 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₈H₄₀N₂	γ = 99.260 (9)°
M_r = 404.62	V = 637.5 (10) Å³
Triclinic, P1	Z = 1
a = 5.993 (6) Å	Mo Kα radiation
b = 10.064 (9) Å	µ = 0.06 mm⁻¹
c = 11.614 (11) Å	T = 296 K
α = 107.913 (9)°	0.23 × 0.21 × 0.18 mm
β = 100.484 (10)°

Data collection top

Bruker APEXII CCD diffractometer	2310 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	1348 reflections with I > 2σ(I)
T_min = 0.986, T_max = 0.989	R_int = 0.030
4557 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.102	42 restraints
wR(F²) = 0.220	H-atom parameters constrained
S = 1.05	Δρ_max = 0.52 e Å⁻³
2310 reflections	Δρ_min = −0.21 e Å⁻³
142 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	0.4381 (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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₈H₄₀N₂
M_r	404.62
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	5.993 (6), 10.064 (9), 11.614 (11)
α, β, γ (°)	107.913 (9), 100.484 (10), 99.260 (9)
V (Å³)	637.5 (10)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.06
Crystal size (mm)	0.23 × 0.21 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.986, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	4557, 2310, 1348
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.102, 0.220, 1.05
No. of reflections	2310
No. of parameters	142
No. of restraints	42
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.21

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

Acknowledgements

We thank the National Natural Science Foundation of China (grant No. 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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Volume 71| Part 4| April 2015| Page o258

doi:10.1107/S2056989015005551

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of 2,3-bis­­[(4-tert-butyl-2,6-di­methyl­phen­yl)imino]­butane

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 2,3-bis[(4-tert-butyl-2,6-dimethylphenyl)imino]butane