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.

In the title compound, C 24 H 25 ClN 2 O 2 , 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-HÁ Á ÁN hydrogen bonds with graph-set motif S(6) between the phenolic hydroxyl groups and N atoms.

Related literature
For related structures, see: Rivera et al. (2012a,b). For the synthesis of the title compound, see: Rivera et al. (2013). For bond-length data, see: Allen et al. (1987). For hydrogen-bond graph-set nomenclature, see: Bernstein et al. (1995).  Table 1 Hydrogen-bond geometry (Å , ).  In the title compound ( Fig. 1), all values of the geometric parameters are normal (Allen et al., 1987). The largest difference maximum 1.2 e -A -3 coincides with the hydrogen H1-C13 and it could be explained by an atom with the scattering power of 2.2 H atoms. We tried to describe this maximum with an O-H group disordered between C5 (occupancy 0.85) and C13 (occupancy 0.15). The difference maximum decreased to ~0.5 e -A -3 , which unfortunately still dominates the difference electron density map and remains at the position of the partially occupied (0.85) H1-C13.

Experimental
Because this disorder complicates the structure description and at the same time does not fully explain the difference maximum, we used for the final CIF the structure model without disorder.
The distances within the imidazolidine ring of the title compund are very similar to those found in related strctures (Rivera et al., 2012a,b). However, the observed N1-C20 bond length

Figure 1
A perspective view of the title compound. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. Hydrogen bonds are drawn as dashed lines.

Special details
Experimental. (CrysAlis PRO; Agilent, 2010) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F 2 for refinement carried out on F and F 2 , respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement. The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program.