N,N,N′,N′-Tetrakis(2-hydroxy-5-methylbenzyl)ethane-1,2-diamine dimethylformamide disolvate

The title compound, C34H40N2O4·2C3H7NO, was synthesized by the Mannich condensation of ethanediamine, formaldehyde and p-cresol. In the crystal, the tetraphenol molecule is arranged around an inversion center. The molecule and the dimethylformamide solvate are linked through an O—H⋯O hydrogen bond. An intramolecular O—H⋯N hydrogen bond occurs in the tetraphenol molecule, which may influence the molecular confomation. Futhermore, C—H⋯O and π–π stacking interactions [centroid–centroid distance = 3.7081 (14) Å] stabilize the crystal packing, building a three-dimensional network.


Comment
Multidentate aminophenol are of interest as metallochelators and as ligands for bioinorganic modeling, catalysis, and medical imaging. (Higham et al., 2006;Farrell et al., 2007). Some of them in combination with metals are used as active catalysts for alkenes polymerization (Tshuva et al., 2000) and initiators in the ring-openingpolymerization of lactones (Liu et al., 2007).
Herein, we report the crystal structure of the title compound, 'C 34 H 40 N 2 O 4 .(C 3 H 7 NO) 2 '.
There is also a weak intramolecular O-H···N interactions which might influence the conformation of the molecule (Table   1) (Hou et al., 2010).

Experimental
The title compound was prepared by mixing ethylenediamine (1.0 mmol), paraformaldehyde (4.0 mmol) and p-cresol (10 mmol) were heated to 90°C and stirred for 18 h. This reaction requires no solvent nor inert atmosphere. At the end of the reaction, 10ml of ethanol was added to the mixtures to remove the unreacted p-cresol, then sonicated 10 minutes. Finally a white precipitate product was collected by filtration in 56% yield.

Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating Rfactors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.