1,3-Dibenzyl-2-(2-chlorophenyl)-4-methylimidazolidine

In the title compound, C24H25ClN2, the methine, methylene and methyl C atoms of the methyl-substituted imidazolidine ring are disordered over two sets of sites with a refined occupancy ratio of 0.834 (4):0.166 (4). Each disordered ring assumes an envelope conformation with an N atom as the flap. The pendant benzyl rings are oriented equatorially with respect to the imidazolidine ring. The chlorophenyl ring is inclined to the mean plane of the four planar atoms of the major component of the imidazolidine ring by 76.27 (12)°. The dihedral angles between the chlorophenyl ring and the two benzyl rings are 55.31 (9) and 57.50 (8)°; the dihedral angle between these latter rings is 71.59 (9)°. In the crystal, molecules are linked by C—H⋯Cl interactions and a number of weak C—H⋯π interactions, involving all three aromatic rings, forming a three-dimensional structure.

In the title compound, C 24 H 25 ClN 2 , the methine, methylene and methyl C atoms of the methyl-substituted imidazolidine ring are disordered over two sets of sites with a refined occupancy ratio of 0.834 (4):0.166 (4). Each disordered ring assumes an envelope conformation with an N atom as the flap. The pendant benzyl rings are oriented equatorially with respect to the imidazolidine ring. The chlorophenyl ring is inclined to the mean plane of the four planar atoms of the major component of the imidazolidine ring by 76.27 (12) . The dihedral angles between the chlorophenyl ring and the two benzyl rings are 55.31 (9) and 57.50 (8) ; the dihedral angle between these latter rings is 71.59 (9) . In the crystal, molecules are linked by C-HÁ Á ÁCl interactions and a number of weak C-HÁ Á Á interactions, involving all three aromatic rings, forming a three-dimensional structure.
Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: JANA2006 (Petříček et al., 2006); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: JANA2006. As part of our studies on the synthesis of new imidazolidine derivatives we have prepared the title compound. It is an imidazolidine-bridged bis(phenol) which can serve as a useful precursor for the synthesis of lanthanide complexes of great potential application in homogeneous catalysis (Xu et al., 2007), and herein we report on its crystal structure.
The chlorophenyl ring attached to C9 (C18-C23) is inclined to the mean plane of the four planar atoms of the major component of the imidazolidine ring by 76.27 (12) °. The dihedral angles between the chlorophenyl ring (C18-C23) and the two benzyl rings (C1-C6) and (C12-C17) are 55.31 (9) and 57.50 (8)°, respectively. The pendant phenyl rings of the benzyl groups are oriented equatorially to the imidazolidine ring. The dihedral angle between these rings is 71.59 (9)°.
In the crystal, molecules are linked by C-H···Cl interactions and a number of weak C-H···π interactions, involving all three aromatic rings (Table 1), forming a three-dimensional structure.

Experimental
A toluene solution of N 1 ,N 2 -dibenzylpropane-1,2-diamine was refluxed for 8 h with 4-chlorobenzaldehyde in a molar ratio of 1.1:1.0. The mixture was evaporated on a rotary evaporator. The residue was cooled, and the precipitate was filtered off. It was then washed with cold ethanol, dried in air, and recrystallized from ethanol [Yield 81%; M.p. 352-353 K].

Refinement
H atoms present in the structural model were discernible in difference Fourier maps and could be refined to reasonable geometry. According to common practice H atoms bonded to C were kept in ideal positions with C-H = 0.96 Å and U iso (H) = 1.2U eq (C,N). The methine, methylene and methyl groups of the methyl substituted imidazolidine ring were found to be disordered with a refined occupancy ratio of 0.834 (4):0.166 (4). The disordered part of the molecule was refined with bond distances of both fractions kept at the same values. The H atoms of the minor fraction could also be found in difference Fourier maps as faint maxima, however, their addition had negligible impact on R values and GOF.
Moreover, it was found that the refined geometry of the minor fraction C atoms is not sufficiently correct for derivation of proper H atom positions, as indicated by too close positions between H2C25′ and H2C7 (1.81Å). However, these H supplementary materials sup-2 Acta Cryst. (2012). E68, o3427-o3428 atoms were retained in the final refined structural model.

Figure 1
A view of the molecular structure of the title compound, showing the atom numbering. Displacement ellipsoids are drawn at the 50% probability level. Only the major component of the disordered methyl substitued imidazolidine ring is shown.