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)
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 cyclohexy...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2020-08-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989020009184 |
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| author | Suttipong Wannapaiboon Yuranan Hanlumyuang Kantapat Chansaenpak Piyanut Pinyou Chatchai Veranitisagul Apirat Laobuthee Worawat Wattanathana |
| author_facet | Suttipong Wannapaiboon Yuranan Hanlumyuang Kantapat Chansaenpak Piyanut Pinyou Chatchai Veranitisagul Apirat Laobuthee Worawat Wattanathana |
| author_sort | Suttipong Wannapaiboon |
| collection | DOAJ |
| description | 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%). |
| first_indexed | 2024-12-24T03:35:54Z |
| format | Article |
| id | doaj.art-be837ab4b0c04e3da59c2fd1200b7a9c |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-12-24T03:35:54Z |
| publishDate | 2020-08-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-be837ab4b0c04e3da59c2fd1200b7a9c2022-12-21T17:17:03ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902020-08-017681239124410.1107/S2056989020009184hb7926Crystal 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)Suttipong Wannapaiboon0Yuranan Hanlumyuang1Kantapat Chansaenpak2Piyanut Pinyou3Chatchai Veranitisagul4Apirat Laobuthee5Worawat Wattanathana6Synchrotron Light Research Institute, 111 University Avenue, Suranaree, Muang, Nakhon Ratchasima 30000, ThailandDepartment of Materials Engineering, Faculty of Engineering, Kasetsart University 10900, ThailandNational Nanotechnology Center, National Science and Technology Development Agency, Thailand Science Park, Pathum Thani, 12120, ThailandSchool of Chemistry, Institute of Science, Suranaree University of Technology, 111 University Avenue, Suranaree, Muang, Nakhon Ratchasima 30000, ThailandDepartment of Materials and Metallurgical Engineering, Faculty of Engineering, Rajamangala University of Technology Thanyaburi, Pathumthani 12110, ThailandDepartment of Materials Engineering, Faculty of Engineering, Kasetsart University 10900, ThailandDepartment of Materials Engineering, Faculty of Engineering, Kasetsart University 10900, ThailandIn 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%).http://scripts.iucr.org/cgi-bin/paper?S2056989020009184crystal structuredihydrobenzoxazinehirshfeld surface |
| spellingShingle | Suttipong Wannapaiboon Yuranan Hanlumyuang Kantapat Chansaenpak Piyanut Pinyou Chatchai Veranitisagul Apirat Laobuthee Worawat Wattanathana 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) Acta Crystallographica Section E: Crystallographic Communications crystal structure dihydrobenzoxazine hirshfeld surface |
| 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) |
| title_full | 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) |
| title_fullStr | 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) |
| title_full_unstemmed | 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) |
| title_short | 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) |
| title_sort | 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 |
| topic | crystal structure dihydrobenzoxazine hirshfeld surface |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989020009184 |
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