Acta Cryst. (2008). E64, o567 [ doi:10.1107/S1600536808003632 ]
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.
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.
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.
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).
![[Figure 1]](./er2044fig1thm.gif)
| 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. |
| C28H24N2 | F000 = 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 = 2.7–26.1º |
| b = 8.017 (3) Å | µ = 0.07 mm−1 |
| c = 14.332 (5) Å | T = 273 (2) K |
| β = 94.740 (6)º | Block, yellow |
| V = 1099.7 (7) Å3 | 0.50 × 0.50 × 0.45 mm |
| Z = 2 |
| Bruker SMART 1K CCD diffractometer | 2373 independent reflections |
| Radiation source: fine-focus sealed tube | 1776 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.029 |
| Detector resolution: 10 pixels mm-1 | θmax = 27.0º |
| T = 273(2) K | θmin = 2.5º |
| 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 on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-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 = 1.03 | Δρmax = 0.27 e Å−3 |
| 2373 reflections | Δρmin = −0.19 e Å−3 |
| 137 parameters | 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) |
| Secondary atom site location: difference Fourier map |
| C28H24N2 | V = 1099.7 (7) Å3 |
| Mr = 388.49 | Z = 2 |
| Monoclinic, P21/n | Mo Kα |
| a = 9.603 (3) Å | µ = 0.07 mm−1 |
| b = 8.017 (3) Å | T = 273 (2) K |
| c = 14.332 (5) Å | 0.50 × 0.50 × 0.45 mm |
| β = 94.740 (6)º |
| Bruker SMART 1K CCD diffractometer | 2373 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | 1776 reflections with I > 2σ(I) |
| Tmin = 0.973, Tmax = 0.976 | Rint = 0.029 |
| 6608 measured reflections |
| R[F2 > 2σ(F2)] = 0.049 | 137 parameters |
| wR(F2) = 0.178 | H-atom parameters constrained |
| S = 1.03 | Δρmax = 0.27 e Å−3 |
| 2373 reflections | Δρmin = −0.19 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 | ||
| 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* |
| 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) |
| 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 codes: (i) −x+1, −y, −z. |
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.
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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.