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

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.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.049
• wR factor = 0.178
• Data-to-parameter ratio = 17.3

checkCIF/PLATON results

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Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C13
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C14

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

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

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

S2. Experimental

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.

S3. Refinement

H atoms were placed in calculated positions [C—H=0.93 Å and U(H) = 1.2U_eq(C)] and were included in the refinement in the riding model approximation.

Computing details

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

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

Crystal data

C28H24N2	F(000) = 412
Mr = 388.49	Dx = 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) Å^3	0.50 × 0.50 × 0.45 mm
Z = 2

Data collection

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

Refinement

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

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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—C13^i	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—C13^i	116.87 (15)
C5—C6—C1	118.00 (15)	C14—C13—C13^i	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.