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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)
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Document Title
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)
Author
Wannapaiboon S, Hanlumyuang Y, Chansaenpak K, Pinyou P, Veranitisagul C, Laobuthee A, Wattanathana W
Name from Authors Collection
Affiliations
Kasetsart University; National Science & Technology Development Agency - Thailand; National Nanotechnology Center (NANOTEC); Suranaree University of Technology; Rajamangala University of Technology Thanyaburi
Type
Article
Source Title
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
Year
2020
Volume
76
Page
1239-+
Open Access
gold, Green Published
Publisher
INT UNION CRYSTALLOGRAPHY
DOI
10.1107/S2056989020009184
Format
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)degrees. 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 center dot center dot center dot N hydrogen bond, generating an S(6) ring, and a short intramolecular C-H center dot center dot center dot O contact is also present. In the crystal, O-H center dot center dot center dot 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 center dot center dot center dot H (76.4%), H center dot center dot center dot C/C center dot center dot center dot H (16.3%), and H center dot center dot center dot O/O center dot center dot center dot H (7.2%).
Keyword
License
CC BY
Publication Source
WOS