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Acta Crystallogr Sect E Struct Rep Online. 2008 March 1; 64(Pt 3): o567.
Published online 2008 February 6. doi:  10.1107/S1600536808003632
PMCID: PMC2960884

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

Abstract

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 [triangle]); Bao, Lü et al. (2006 [triangle]); Bao, Ma et al. (2006 [triangle]); Zou et al. (2005 [triangle]).

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Object name is e-64-0o567-scheme1.jpg

Experimental

Crystal data

  • C28H24N2
  • M r = 388.49
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o567-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.178
  • S = 1.03
  • 2373 reflections
  • 137 parameters
  • H-atom parameters constrained
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.19 e Å−3

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

Supplementary Material

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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.

supplementary crystallographic information

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.

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.

Refinement

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

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.

Crystal data

C28H24N2F000 = 412
Mr = 388.49Dx = 1.173 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 775 reflections
a = 9.603 (3) Åθ = 2.7–26.1º
b = 8.017 (3) ŵ = 0.07 mm1
c = 14.332 (5) ÅT = 273 (2) K
β = 94.740 (6)ºBlock, yellow
V = 1099.7 (7) Å30.50 × 0.50 × 0.45 mm
Z = 2

Data collection

Bruker SMART 1K CCD diffractometer2373 independent reflections
Radiation source: fine-focus sealed tube1776 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.029
Detector resolution: 10 pixels mm-1θmax = 27.0º
T = 273(2) Kθmin = 2.5º
ω scansh = −12→12
Absorption correction: multi-scan(SADABS; Sheldrick, 2002)k = −10→8
Tmin = 0.973, Tmax = 0.976l = −15→18
6608 measured reflections

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.049  w = 1/[σ2(Fo2) + (0.1119P)2 + 0.1177P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.178(Δ/σ)max < 0.001
S = 1.03Δρmax = 0.27 e Å3
2373 reflectionsΔρmin = −0.19 e Å3
137 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.126 (15)
Secondary atom site location: difference Fourier map

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 (Å2)

xyzUiso*/Ueq
N10.41183 (12)0.12272 (16)0.07641 (9)0.0549 (4)
C10.28095 (15)0.14069 (18)0.11538 (11)0.0522 (4)
C20.26218 (19)0.0733 (2)0.20274 (12)0.0678 (5)
H2A0.33360.01170.23400.081*
C30.1387 (2)0.0970 (2)0.24353 (14)0.0766 (6)
H3A0.12690.05050.30180.092*
C40.03264 (19)0.1895 (2)0.19818 (14)0.0728 (5)
H4A−0.05010.20730.22610.087*
C50.05000 (16)0.2551 (2)0.11148 (13)0.0626 (5)
H5A−0.02240.31630.08100.075*
C60.17315 (14)0.23261 (18)0.06781 (10)0.0513 (4)
C70.18618 (15)0.30173 (19)−0.02718 (10)0.0540 (4)
C80.29127 (18)0.4124 (2)−0.04477 (12)0.0638 (5)
H8A0.35720.44200.00360.077*
C90.3002 (2)0.4798 (3)−0.13270 (13)0.0799 (6)
H9A0.37080.5554−0.14290.096*
C100.2048 (3)0.4352 (3)−0.20518 (14)0.0936 (8)
H10A0.21040.4808−0.26440.112*
C110.1018 (3)0.3236 (3)−0.18970 (15)0.0941 (8)
H11A0.03830.2920−0.23910.113*
C120.09052 (19)0.2568 (3)−0.10133 (13)0.0731 (5)
H12A0.01910.1820−0.09160.088*
C130.43020 (13)0.00418 (18)0.02004 (10)0.0503 (4)
C140.32384 (18)−0.1253 (3)−0.00980 (15)0.0783 (6)
H14C0.3624−0.2013−0.05260.117*
H14B0.2426−0.0724−0.04010.117*
H14A0.2982−0.18550.04410.117*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0449 (7)0.0577 (7)0.0620 (8)0.0032 (5)0.0036 (5)−0.0031 (6)
C10.0450 (7)0.0529 (8)0.0590 (8)−0.0012 (6)0.0060 (6)−0.0063 (6)
C20.0647 (10)0.0702 (10)0.0682 (10)0.0027 (8)0.0049 (8)0.0078 (8)
C30.0831 (13)0.0817 (12)0.0680 (11)−0.0117 (10)0.0237 (9)0.0057 (9)
C40.0608 (10)0.0759 (11)0.0854 (12)−0.0047 (9)0.0285 (9)−0.0047 (9)
C50.0489 (9)0.0618 (9)0.0783 (11)0.0025 (7)0.0126 (7)−0.0076 (7)
C60.0464 (8)0.0481 (8)0.0594 (8)−0.0015 (6)0.0056 (6)−0.0090 (6)
C70.0503 (8)0.0545 (8)0.0570 (8)0.0132 (6)0.0045 (6)−0.0080 (6)
C80.0706 (10)0.0619 (10)0.0605 (10)0.0030 (8)0.0155 (7)−0.0056 (7)
C90.1029 (15)0.0716 (11)0.0695 (11)0.0155 (10)0.0331 (10)0.0031 (9)
C100.128 (2)0.0970 (16)0.0586 (11)0.0514 (15)0.0237 (12)0.0052 (10)
C110.1005 (16)0.1150 (18)0.0631 (12)0.0464 (15)−0.0156 (11)−0.0194 (12)
C120.0634 (10)0.0816 (12)0.0721 (11)0.0155 (9)−0.0080 (8)−0.0144 (9)
C130.0435 (8)0.0497 (8)0.0573 (8)0.0037 (6)0.0018 (6)0.0011 (6)
C140.0592 (10)0.0759 (12)0.1026 (14)−0.0153 (9)0.0236 (9)−0.0272 (10)

Geometric parameters (Å, °)

N1—C131.2691 (19)C8—C91.380 (3)
N1—C11.424 (2)C8—H8A0.9300
C1—C21.389 (2)C9—C101.374 (3)
C1—C61.401 (2)C9—H9A0.9300
C2—C31.378 (3)C10—C111.365 (3)
C2—H2A0.9300C10—H10A0.9300
C3—C41.378 (3)C11—C121.388 (3)
C3—H3A0.9300C11—H11A0.9300
C4—C51.372 (3)C12—H12A0.9300
C4—H4A0.9300C13—C141.494 (2)
C5—C61.395 (2)C13—C13i1.503 (3)
C5—H5A0.9300C14—H14C0.9600
C6—C71.485 (2)C14—H14B0.9600
C7—C81.383 (2)C14—H14A0.9600
C7—C121.393 (2)
C13—N1—C1119.94 (12)C9—C8—H8A119.4
C2—C1—C6119.83 (14)C7—C8—H8A119.4
C2—C1—N1119.91 (14)C10—C9—C8120.0 (2)
C6—C1—N1120.19 (14)C10—C9—H9A120.0
C3—C2—C1120.61 (16)C8—C9—H9A120.0
C3—C2—H2A119.7C11—C10—C9119.61 (19)
C1—C2—H2A119.7C11—C10—H10A120.2
C2—C3—C4120.15 (17)C9—C10—H10A120.2
C2—C3—H3A119.9C10—C11—C12120.9 (2)
C4—C3—H3A119.9C10—C11—H11A119.5
C5—C4—C3119.54 (16)C12—C11—H11A119.5
C5—C4—H4A120.2C11—C12—C7120.0 (2)
C3—C4—H4A120.2C11—C12—H12A120.0
C4—C5—C6121.86 (16)C7—C12—H12A120.0
C4—C5—H5A119.1N1—C13—C14125.10 (14)
C6—C5—H5A119.1N1—C13—C13i116.87 (15)
C5—C6—C1118.00 (15)C14—C13—C13i118.03 (16)
C5—C6—C7120.13 (14)C13—C14—H14C109.5
C1—C6—C7121.85 (13)C13—C14—H14B109.5
C8—C7—C12118.16 (16)H14C—C14—H14B109.5
C8—C7—C6121.66 (14)C13—C14—H14A109.5
C12—C7—C6120.18 (16)H14C—C14—H14A109.5
C9—C8—C7121.27 (18)H14B—C14—H14A109.5

Symmetry codes: (i) −x+1, −y, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ER2044).

References

  • Bao, F., Lü, X.-Q., Gao, H.-Y., Gui, G.-Q. & Wu, Q. (2005). J. Polym. Sci. Part A Polym. Chem.43, 5535–5544.
  • Bao, F., Lü, X.-Q., Kang, B.-S. & Wu, Q. (2006). Eur. Polym. J.42, 928–934.
  • Bao, F., Ma, R., Lü, X.-Q., Gui, G.-Q. & Wu, Q. (2006). Appl. Organomet. Chem.20, 32–38.
  • Bergerhoff, G. (1996). DIAMOND Bonn, Germany.
  • Bruker (1998). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2002). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Zou, H., Zhu, F.-M., Wu, Q., Ai, J.-Y. & Lin, S.-A. (2005). J. Polym. Sci. Part A Polym. Chem.43, 1325–1330.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography