(E,E)-N-[3-(Biphenyl-2-ylimino)butan-2-yl­idene]-2-phenyl­aniline

Zou, H.; Hou, Y.; Yong, X.; Cen, Y.; Bao, F.

doi:10.1107/S1600536808003632

organic compounds

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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Page o567

doi:10.1107/S1600536808003632

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(E,E)-N-[3-(Biphenyl-2-ylimino)butan-2-ylidene]-2-phenylaniline

Hao Zou,^a Yubang Hou,^b Xuejian Yong,^b Yunbin Cen ^b and Feng Bao ^b ^*

^aInstitute of Polymer Science, School of Chemistry and Chemical Engineering, Sun Yat-Sen (Zhongshan) University, Guangzhou 510275, People's Republic of China, and ^bDepartment of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China
^*Correspondence e-mail: baofengstorm@126.com

(Received 2 October 2007; accepted 1 February 2008; online 6 February 2008)

The two C=N double bonds in the structure of the title compound, C₂₈H₂₄N₂, lie in the same plane with a bond length of 1.269 (2) Å. The molecule is positioned on a centre of symmetry.

Related literature

For related literature, see: Bao et al. (2005 ); Bao, Lü et al. (2006 ); Bao, Ma et al. (2006 ); Zou et al. (2005 ).

Experimental

Crystal data

C₂₈H₂₄N₂
M_r = 388.49
Monoclinic, P 2₁ /n
a = 9.603 (3) Å
b = 8.017 (3) Å
c = 14.332 (5) Å
β = 94.740 (6)°
V = 1099.7 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 273 (2) K
0.50 × 0.50 × 0.45 mm

Data collection

Bruker SMART 1K CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ) T_min = 0.973, T_max = 0.976
6608 measured reflections
2373 independent reflections
1776 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.178
S = 1.03
2373 reflections
137 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT ; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Bergerhoff, 1996 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808003632/er2044sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808003632/er2044Isup2.hkl

checkCIF report

Comment top

As the late metal complexes are effective catalysts in the polymerization of ethylene and other olefins (Bao et al., 2005), a number of studies have been directed towards the development of the late transition metal complexes (Bao, Ma et al., 2006). The studies have been complemented by a report that the α–diimine ligand unit of the Ni complex is responsible for catalytic activity in the homopolymerization of ethylene (Zou et al., 2005). The crystal structure of this α-diimine ligand has been obtained by our group. It was characterized by X-ray diffraction.

Related literature top

For related literature, see: Bao et al. (2005); Bao, Lü et al. (2006); Bao, Ma et al. (2006); Zou et al. (2005).

Experimental top

α-Diimine ligands was prepared according to modified literature procedures (Bao et al., 2005; Bao, Lü et al., 2006; Bao, Ma et al., 2006). 3-Butanedione 1.3 ml (1.27 g, 14.8 mmol) and 2-aminobiphenyl 5.00 g (29.5 mmol) were stirred for 5 h at 55°C in 25 ml of ethanol containing 1 ml formic acid. The precipitated orange solid was collected by filtration and dried. The crude product was recrystallized from a mixed solvent of petroleum aether/ethyl acetate 1:1 to give the pure ligand, yield 3.20 g, 51.04%. Anal. Calcd. for C₂₈H₂₄N₂: C, 86.56; H, 6.23; N, 7.21. Found: C, 86.48; H, 6.25; N, 7.02. Crystals suitable for X-ray structure determination were grown from a solution of the title compound in a (1:1) mixture of dichloromethane-ethanol.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Bergerhoff, 1996); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Vew of (I), with displacement ellipsoids drawn at the 50% probability level. H atoms are drawn as spheres of arbitrary radius and the hydrogen bond is indicated by a double-dashed line.

(E,E)—N-[3-(Biphenyl-2-ylimino)butan-2-ylidene]-2-phenylaniline top

Crystal data top

C₂₈H₂₄N₂	F(000) = 412
M_r = 388.49	D_x = 1.173 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 775 reflections
a = 9.603 (3) Å	θ = 2.7–26.1°
b = 8.017 (3) Å	µ = 0.07 mm⁻¹
c = 14.332 (5) Å	T = 273 K
β = 94.740 (6)°	Block, yellow
V = 1099.7 (7) Å³	0.50 × 0.50 × 0.45 mm
Z = 2

Data collection top

Bruker SMART 1K CCD diffractometer	2373 independent reflections
Radiation source: fine-focus sealed tube	1776 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 10 pixels mm^-1	θ_max = 27.0°, θ_min = 2.5°
ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	k = −10→8
T_min = 0.973, T_max = 0.976	l = −15→18
6608 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.049	H-atom parameters constrained
wR(F²) = 0.178	w = 1/[σ²(F_o²) + (0.1119P)² + 0.1177P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
2373 reflections	Δρ_max = 0.27 e Å⁻³
137 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.126 (15)

Crystal data top

C₂₈H₂₄N₂	V = 1099.7 (7) Å³
M_r = 388.49	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.603 (3) Å	µ = 0.07 mm⁻¹
b = 8.017 (3) Å	T = 273 K
c = 14.332 (5) Å	0.50 × 0.50 × 0.45 mm
β = 94.740 (6)°

Data collection top

Bruker SMART 1K CCD diffractometer	2373 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	1776 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.976	R_int = 0.029
6608 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.178	H-atom parameters constrained
S = 1.03	Δρ_max = 0.27 e Å⁻³
2373 reflections	Δρ_min = −0.19 e Å⁻³
137 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
N1	0.41183 (12)	0.12272 (16)	0.07641 (9)	0.0549 (4)
C1	0.28095 (15)	0.14069 (18)	0.11538 (11)	0.0522 (4)
C2	0.26218 (19)	0.0733 (2)	0.20274 (12)	0.0678 (5)
H2A	0.3336	0.0117	0.2340	0.081*
C3	0.1387 (2)	0.0970 (2)	0.24353 (14)	0.0766 (6)
H3A	0.1269	0.0505	0.3018	0.092*
C4	0.03264 (19)	0.1895 (2)	0.19818 (14)	0.0728 (5)
H4A	−0.0501	0.2073	0.2261	0.087*
C5	0.05000 (16)	0.2551 (2)	0.11148 (13)	0.0626 (5)
H5A	−0.0224	0.3163	0.0810	0.075*
C6	0.17315 (14)	0.23261 (18)	0.06781 (10)	0.0513 (4)
C7	0.18618 (15)	0.30173 (19)	−0.02718 (10)	0.0540 (4)
C8	0.29127 (18)	0.4124 (2)	−0.04477 (12)	0.0638 (5)
H8A	0.3572	0.4420	0.0036	0.077*
C9	0.3002 (2)	0.4798 (3)	−0.13270 (13)	0.0799 (6)
H9A	0.3708	0.5554	−0.1429	0.096*
C10	0.2048 (3)	0.4352 (3)	−0.20518 (14)	0.0936 (8)
H10A	0.2104	0.4808	−0.2644	0.112*
C11	0.1018 (3)	0.3236 (3)	−0.18970 (15)	0.0941 (8)
H11A	0.0383	0.2920	−0.2391	0.113*
C12	0.09052 (19)	0.2568 (3)	−0.10133 (13)	0.0731 (5)
H12A	0.0191	0.1820	−0.0916	0.088*
C13	0.43020 (13)	0.00418 (18)	0.02004 (10)	0.0503 (4)
C14	0.32384 (18)	−0.1253 (3)	−0.00980 (15)	0.0783 (6)
H14C	0.3624	−0.2013	−0.0526	0.117*
H14B	0.2426	−0.0724	−0.0401	0.117*
H14A	0.2982	−0.1855	0.0441	0.117*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0449 (7)	0.0577 (7)	0.0620 (8)	0.0032 (5)	0.0036 (5)	−0.0031 (6)
C1	0.0450 (7)	0.0529 (8)	0.0590 (8)	−0.0012 (6)	0.0060 (6)	−0.0063 (6)
C2	0.0647 (10)	0.0702 (10)	0.0682 (10)	0.0027 (8)	0.0049 (8)	0.0078 (8)
C3	0.0831 (13)	0.0817 (12)	0.0680 (11)	−0.0117 (10)	0.0237 (9)	0.0057 (9)
C4	0.0608 (10)	0.0759 (11)	0.0854 (12)	−0.0047 (9)	0.0285 (9)	−0.0047 (9)
C5	0.0489 (9)	0.0618 (9)	0.0783 (11)	0.0025 (7)	0.0126 (7)	−0.0076 (7)
C6	0.0464 (8)	0.0481 (8)	0.0594 (8)	−0.0015 (6)	0.0056 (6)	−0.0090 (6)
C7	0.0503 (8)	0.0545 (8)	0.0570 (8)	0.0132 (6)	0.0045 (6)	−0.0080 (6)
C8	0.0706 (10)	0.0619 (10)	0.0605 (10)	0.0030 (8)	0.0155 (7)	−0.0056 (7)
C9	0.1029 (15)	0.0716 (11)	0.0695 (11)	0.0155 (10)	0.0331 (10)	0.0031 (9)
C10	0.128 (2)	0.0970 (16)	0.0586 (11)	0.0514 (15)	0.0237 (12)	0.0052 (10)
C11	0.1005 (16)	0.1150 (18)	0.0631 (12)	0.0464 (15)	−0.0156 (11)	−0.0194 (12)
C12	0.0634 (10)	0.0816 (12)	0.0721 (11)	0.0155 (9)	−0.0080 (8)	−0.0144 (9)
C13	0.0435 (8)	0.0497 (8)	0.0573 (8)	0.0037 (6)	0.0018 (6)	0.0011 (6)
C14	0.0592 (10)	0.0759 (12)	0.1026 (14)	−0.0153 (9)	0.0236 (9)	−0.0272 (10)

Geometric parameters (Å, º) top

N1—C13	1.2691 (19)	C8—C9	1.380 (3)
N1—C1	1.424 (2)	C8—H8A	0.9300
C1—C2	1.389 (2)	C9—C10	1.374 (3)
C1—C6	1.401 (2)	C9—H9A	0.9300
C2—C3	1.378 (3)	C10—C11	1.365 (3)
C2—H2A	0.9300	C10—H10A	0.9300
C3—C4	1.378 (3)	C11—C12	1.388 (3)
C3—H3A	0.9300	C11—H11A	0.9300
C4—C5	1.372 (3)	C12—H12A	0.9300
C4—H4A	0.9300	C13—C14	1.494 (2)
C5—C6	1.395 (2)	C13—C13ⁱ	1.503 (3)
C5—H5A	0.9300	C14—H14C	0.9600
C6—C7	1.485 (2)	C14—H14B	0.9600
C7—C8	1.383 (2)	C14—H14A	0.9600
C7—C12	1.393 (2)

C13—N1—C1	119.94 (12)	C9—C8—H8A	119.4
C2—C1—C6	119.83 (14)	C7—C8—H8A	119.4
C2—C1—N1	119.91 (14)	C10—C9—C8	120.0 (2)
C6—C1—N1	120.19 (14)	C10—C9—H9A	120.0
C3—C2—C1	120.61 (16)	C8—C9—H9A	120.0
C3—C2—H2A	119.7	C11—C10—C9	119.61 (19)
C1—C2—H2A	119.7	C11—C10—H10A	120.2
C2—C3—C4	120.15 (17)	C9—C10—H10A	120.2
C2—C3—H3A	119.9	C10—C11—C12	120.9 (2)
C4—C3—H3A	119.9	C10—C11—H11A	119.5
C5—C4—C3	119.54 (16)	C12—C11—H11A	119.5
C5—C4—H4A	120.2	C11—C12—C7	120.0 (2)
C3—C4—H4A	120.2	C11—C12—H12A	120.0
C4—C5—C6	121.86 (16)	C7—C12—H12A	120.0
C4—C5—H5A	119.1	N1—C13—C14	125.10 (14)
C6—C5—H5A	119.1	N1—C13—C13ⁱ	116.87 (15)
C5—C6—C1	118.00 (15)	C14—C13—C13ⁱ	118.03 (16)
C5—C6—C7	120.13 (14)	C13—C14—H14C	109.5
C1—C6—C7	121.85 (13)	C13—C14—H14B	109.5
C8—C7—C12	118.16 (16)	H14C—C14—H14B	109.5
C8—C7—C6	121.66 (14)	C13—C14—H14A	109.5
C12—C7—C6	120.18 (16)	H14C—C14—H14A	109.5
C9—C8—C7	121.27 (18)	H14B—C14—H14A	109.5

Symmetry code: (i) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	C₂₈H₂₄N₂
M_r	388.49
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	273
a, b, c (Å)	9.603 (3), 8.017 (3), 14.332 (5)
β (°)	94.740 (6)
V (Å³)	1099.7 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.50 × 0.50 × 0.45

Data collection
Diffractometer	Bruker SMART 1K CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2002)
T_min, T_max	0.973, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	6608, 2373, 1776
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.640

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.178, 1.03
No. of reflections	2373
No. of parameters	137
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.19

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Bergerhoff, 1996), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors thank the Central China Normal University and the China University of Geosciences for supporting this work. The support of the Education Bureau of Hubei Province (project D2006–28004) and the Technologies R&D Programme of Hubei Province (2005 A A401D57, 2006 A A101C39) is gratefully acknowledged.

References

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