2,2′-[(4-Methyl-2-phenyl­imidazolidine-1,3-di­yl)bis­(methyl­ene)]diphenol

The methyl-substituted imidazolidine ring of the title compound, C₂₄H₂₆N₂O₂, adopts an envelope conformation with the N atom adjacent to the methyl­ene group as the flap. The meth­yl–ethyl­ene fragment in this ring is disordered over two positions with an occupancy ratio of 0.899 (4):0.101 (4). The hy­droxy­benzyl groups are inclined at 71.57 (15) and 69.97 (19)° to the mean plane of major disorder component of the heterocyclic ring with an inter­planar angle between the two hy­droxy­benzyl groups of 66.00 (5)°. The phenyl substit­uent approaches a nearly perpendicular orientation relative to the mean plane of the imidazolidine ring, making a dihedral angle of 75.60 (12)°. This conformation is stabilized by two intra­molecular O—H...N bonds, which generate S(6) ring motifs.

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

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.

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

The asymmetric unit in the title compound, C₂₄H₂₆N₂O₃, comprises two independent mol­ecules (A and B). In molecule A, the central 2-hydroxyphenyl ring is inclined to the mean plane of the major component of the imidazolidine ring by 84.52 (14)°, and by 68.08 (9) and 47.48 (9)° to the outer phenol rings. The later are inclined to one another by 66.76 (9)° and by 78.12 (14) and 80.20 (14)° to the imidazoline ring mean plane. In molecule B, the central 2-hydroxyphenyl ring is inclined to the mean plane of the imidazolidine ring by 73.64 (10)°, and by 75.60 (8) and 38.32 (9)° to the outer phenol rings. The later are inclined to one another by 69.47 (9)° and by 82.60 (10) and 64.26 (10)° to the imidazolidine ring mean plane. In each of the independent mol­ecules, two intra­molecular O—H...N hydrogen bond form S(6) ring motifs. In disordered mol­ecule A, the O—H groups of the 2-hy­droxy­benzyl groups are also involved in intra­molecular O—H...O hydrogen bonds, with the O atom of the hy­droxy­phenyl group acting as the acceptor. In the crystal, A molecules are linked by pairs of O—H...O hydrogen bonds forming inversion dimers. These dimers are linked to the B molecules via O—H...O hydrogen bonds forming double-layered slabs lying parallel to the bc plane.