Rac-4-Chloro-2-[({2-[(3-chloro-6-hydroxy-2,4-dimethylbenzyl)(methyl)amino]propyl}(methyl)amino)methyl]-3,5-dimethylphenol

Augusto Rivera,Jaime Ríos-Motta,Michael Bolte,Dency José Pacheco,Mauricio Maldonado

doi:10.1107/s1600536812039694

Abstract

The title compound, C23H32Cl2N2O2, a potential chiral ligand for coordination chemistry, was prepared by a two-step reaction. The molecule is located on a crystallographic centre of inversion. As a result, the methyl group bonded to the methylene group is disordered over two equally occupied positions, sharing the same site as the H atom of the chiral C atom. As a further consequence of the crystallographic centrosymmetry, the 1,2-diaminopropane unit adopts an antiperiplanar conformation and the two benzene rings are coplanar. The central chain is in an all-trans arrangement. An intramolecular O—H⋯N hydrogen bond makes an S(6) ring motif. A C—H⋯π interaction links the molecules into one-dimensional chains along the [001] direction.

Highlights

Data collectionAugusto Rivera,a* Dency José Pacheco,a Jaime RıosMotta,a Mauricio Maldonadoa and Michael Bolteb
The title compound, C23H32Cl2N2O2, a potential chiral ligand for coordination chemistry, was prepared by a two-step reaction
Cg1 is the centroid of the C11–C16 ring

Summary

Data collection

Augusto Rivera,a* Dency José Pacheco,a Jaime RıosMotta,a Mauricio Maldonadoa and Michael Bolteb. Key indicators: single-crystal X-ray study; T = 173 K; mean (C–C) = 0.004 Å; disorder in main residue; R factor = 0.064; wR factor = 0.159; data-to-parameter ratio = 14.3. Cg1 is the centroid of the C11–C16 ring. The molecule is located on a crystallographic centre of inversion. The methyl group bonded to the methylene group is disordered over two occupied positions, sharing the same site as the H atom of the chiral C atom. As a further consequence of the crystallographic centrosymmetry, the 1,2-diaminopropane unit adopts an antiperiplanar conformation and the two benzene rings are coplanar. The central chain is in an all-trans arrangement. An intramolecular O—H N hydrogen bond makes an S(6) ring motif. A C—H interaction links the molecules into onedimensional chains along the [001] direction

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