Crystal structure and Hirshfeld surface analysis of the product of the ring-opening reaction of a dihydrobenzoxazine: 6,6′-[(cyclohexylazanediyl)bis(methylene)]bis(2,4-dimethylphenol)

Abstract

In the title unsymmetrical tertiary amine, C24H33NO2, which arose from the ring-opening reaction of a dihydrobenzoxazine, two 2,4-dimethylphenol moieties are linked by a 6,6′-(cyclohexylazanediyl)-bis(methylene) bridge: the dihedral angle between the dimethylphenol rings is 72.45 (7)°. The cyclohexyl ring adopts a chair conformation with the exocyclic C—N bond in an equatorial orientation. One of the phenol OH groups forms an intramolecular O—H...N hydrogen bond, generating an S(6) ring, and a short intramolecular C—H...O contact is also present. In the crystal, O—H...O hydrogen bonds link the molecules into C(10) chains propagating along the [100] direction. The Hirshfeld surface analysis of the title compound confirms the presence of these intra- and intermolecular interactions. The corresponding fingerprint plots indicate that the most significant contacts in the crystal packing are H...H (76.4%), H...C/C...H (16.3%), and H...O/O...H (7.2%).