Crystal structure and Hirshfeld surface analysis of the product of the ring-opening reaction of a di-hydro-benzoxazine: 6,6'-[(cyclo-hexyl-aza-nedi-yl)bis-(methyl-ene)]bis-(2,4-di-methyl-phenol)

Suttipong Wannapaiboon; Yuranan Hanlumyuang; Kantapat Chansaenpak; Piyanut Pinyou; Chatchai Veranitisagul; Apirat Laobuthee; Worawat Wattanathana

doi:10.1107/S2056989020009184

Crystal structure and Hirshfeld surface analysis of the product of the ring-opening reaction of a di-hydro-benzoxazine: 6,6'-[(cyclo-hexyl-aza-nedi-yl)bis-(methyl-ene)]bis-(2,4-di-methyl-phenol)

Acta Crystallogr E Crystallogr Commun. 2020 Jul 10;76(Pt 8):1239-1244. doi: 10.1107/S2056989020009184. eCollection 2020 Aug 1.

Authors

Suttipong Wannapaiboon¹, Yuranan Hanlumyuang², Kantapat Chansaenpak³, Piyanut Pinyou⁴, Chatchai Veranitisagul⁵, Apirat Laobuthee², Worawat Wattanathana²

Affiliations

¹ Synchrotron Light Research Institute, 111 University Avenue, Suranaree, Muang, Nakhon Ratchasima 30000, Thailand.
² Department of Materials Engineering, Faculty of Engineering, Kasetsart University 10900, Thailand.
³ National Nanotechnology Center, National Science and Technology Development Agency, Thailand Science Park, Pathum Thani, 12120, Thailand.
⁴ School of Chemistry, Institute of Science, Suranaree University of Technology, 111 University Avenue, Suranaree, Muang, Nakhon Ratchasima 30000, Thailand.
⁵ Department of Materials and Metallurgical Engineering, Faculty of Engineering, Rajamangala University of Technology Thanyaburi, Pathumthani 12110, Thailand.

Abstract

In the title unsymmetrical tertiary amine, C₂₄H₃₃NO₂, which arose from the ring-opening reaction of a di-hydro-benzoxazine, two 2,4-di-methyl-phenol moieties are linked by a 6,6'-(cyclo-hexyl-aza-nedi-yl)-bis-(methyl-ene) bridge: the dihedral angle between the dimethyl-phenol rings is 72.45 (7)°. The cyclo-hexyl ring adopts a chair conformation with the exocyclic C-N bond in an equatorial orientation. One of the phenol OH groups forms an intra-molecular O-H⋯N hydrogen bond, generating an S(6) ring, and a short intra-molecular C-H⋯O contact is also present. In the crystal, O-H⋯O hydrogen bonds link the mol-ecules into C(10) chains propagating along the [100] direction. The Hirshfeld surface analysis of the title compound confirms the presence of these intra- and inter-molecular inter-actions. 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%).

Keywords: Hirshfeld surface; crystal structure; dihydrobenzoxazine.