Acta Crystallographica Section E

Structure Reports Online

Volume 69, Part 8 (August 2013)


organic compounds



bx2443 scheme

Acta Cryst. (2013). E69, o1221-o1222    [ doi:10.1107/S1600536813017923 ]

2,2'-{[2-(2-Chlorophenyl)-4-methylimidazolidine-1,3-diyl]bis(methylene)}diphenol

A. Rivera, L. Cárdenas, J. Ríos-Motta, M. Kuceraková and M. Dusek

Abstract: In the title compound, C24H25ClN2O2, the 2-hydroxybenzyl substituents and the 2-chlorophenyl group occupy the sterically preferred equatorial positions, whereas the methyl group occupies the axial position. The imidazolidine ring adopts an envelope conformation with one of the N atoms adjacent to the methylene group as the flap. The chlorophenyl substituent approaches a nearly perpendicular orientation relative to the mean plane of the imidazolidine ring, making a dihedral angle of 73.44 (12)° and the Cl atom is almost coplanar with the C atom bearing the chlorophenyl substituent [Cl-C-C-C torsion angle = 1.1 (3)°]. The hydroxybenzyl groups make dihedral angles of 71.23 (15) and 69.13 (19)° with the mean plane of the heterocyclic ring. The dihedral angle between the two hydroxybenzyl groups is 69.61 (12)°. The molecular structure features two intramolecular O-H...N hydrogen bonds with graph-set motif S(6) between the phenolic hydroxyl groups and N atoms.


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