2-[(Cyclopenta-1,3-dien-2-yl)diphenylmethyl]-1-methyl-1H-imidazole

Abstract

The title compound, C22H20N2, (Ib), forms along with 2-[(cyclo­penta-1,3-dien-1-yl)diphenyl­meth­yl]-1-methyl-1H-imid­azole, (Ia), which differs with respect to the position of the double-bonds in the C5H5 ring, in an approximately 3:7 ratio (Ia:Ib; NMR spectroscopy data). However, in a single crystal, only compound (Ib) is present. H atoms of the CH2 group (C5H5 ring) were found from the difference Fourier synthesis and refined isotropically using the riding model. Hypothesis on possible presence of the (Ia) isomer in crystal lattice (model with a C5H5 ring disordered between two positions) was especially checked and rejected due to its inconsistency. In the crystal structure, no significant hydrogen-bonding inter­actions between the CH2 groups of the C5H5 rings and nonsubstituted N-atoms of the imidazole rings were observed. Despite the fact that the chemically achiral compound (I) crystallizes in a chiral space group P212121, neither the absolute structure determination nor assignment of the inversion twinning was possible in the absence of a heavy atom.

2-{(E)-N-[2-(1H-Inden-3-yl)ethyl]iminomethyl}-1H-imidazole

“…For the structural parameters of 3-organyl substituted 1Hindenes (organic structures only), see: Sun et al (2010) and references cited therein. For the structural parameters of 2organyl-1H-imidazoles (organic structures only, not bi-or oligocyclic, non-ionic, recent publications only), see: Lassalle-Kaiser et al (2006).…”

“…For the structural parameters of Li, Ti, and Zr complexes derived from 1H-imidazol(in)-2-yl side-chainfunctionalized cyclopentadienes see: Krut'ko et al (2006); Nie et al (2008); Wang et al (2009); Ge et al (2010). For the structural parameters of 1H-imidazol(in)-2-yl side-chainfunctionalized 3-substituted 1H-indene and Li-indenide, see: Sun et al (2009Sun et al ( , 2010. For graph-set notation, see: Etter et al (1990); Bernstein et al (1995).…”

“…1H-Imidazol(in)-2-yl side-chain functionalized cyclopentadiene-type (Cp) ligands were introduced into the organometallic chemistry, and, particularly into that of the Group 4 transition metals, not long ago (Krut'ko et al, 2006;Nie et al, 2008;Wang et al, 2009;Sun et al, 2009;Sun et al, 2010;Ge et al, 2010). All these compounds are usually considered to be prospective precursors for catalytic systems capable to effectively polymerize ethylene and α-olefins.…”

{2-[(η5-Cyclopentadienyl)diphenylmethyl]-1H-imidazolido-κN}bis(N,N-diethylamido)titanium(IV)

“…Cyclopentadienes (Cp-s) with pendant 1H-imidazol(in)-2-yl side-chain functional groups, their mono-and di-Li salts, and group 4 transition metal complexes of general type [η 5 -Cp-(C 1 or C 2 )-imidazol(in)e)-κN]-M IV L n [M = Ti, Zr; L n = Cl 3 , (NR 2 ) 2 ] have been described previously (Krut'ko et al, 2006;Nie et al, 2008;Sun et al, 2009;Wang et al, 2009;Ge et al, 2010;Sun et al, 2010). The present contribution reports the structural investigation of the closest analogue of two Ti IV 18e -(η 5 -Cp)tris(sec-amido)-type complexes described recently by Wang et al (2009).…”