1-{(E)-[4-(4-Hydroxyphenyl)butan-2-ylidene]amino}-3-phenylthiourea: crystal structure, Hirshfeld surface analysis and computational study
The title thio-urea derivative, C17H19N3OS, adopts a U-shaped conformation with the dihedral angle between the terminal aromatic rings being 73.64 (5)°. The major twist in the mol-ecule occurs about the ethane bond with the Ci-Ce-Ce-Cb torsion angle being -78.12 (18)°; i = imine, e = ethane and b =...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2021
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| Online Access: | http://eprints.sunway.edu.my/1792/ http://eprints.sunway.edu.my/1792/1/Tiekink%20acta%20cryst%202021%20e77%20788.pdf |
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| author | Tan, Ming Yueh Kwong, Huey Chong * Crouse, Karen A. Ravoof, Thahira Begum S. A. Tiekink, Edward R. T. * |
| author_facet | Tan, Ming Yueh Kwong, Huey Chong * Crouse, Karen A. Ravoof, Thahira Begum S. A. Tiekink, Edward R. T. * |
| author_sort | Tan, Ming Yueh |
| building | SU Institutional Repository |
| collection | Online Access |
| description | The title thio-urea derivative, C17H19N3OS, adopts a U-shaped conformation with the dihedral angle between the terminal aromatic rings being 73.64 (5)°. The major twist in the mol-ecule occurs about the ethane bond with the Ci-Ce-Ce-Cb torsion angle being -78.12 (18)°; i = imine, e = ethane and b = benzene. The configuration about the imine bond is E, the N-bound H atoms lie on opposite sides of the mol-ecule and an intra-molecular amine-N-H⋯N(imine) hydrogen bond is evident. In the mol-ecular packing, hydroxyl-O-H⋯S(thione) and amine-N-H⋯O hydrogen bonding feature within a linear, supra-molecular chain. The chains are connected into a layer in the ab plane by a combination of methyl-ene-C-H⋯S(thione), methyl-ene-C-H⋯O(hydrox-yl), methyl-C-H⋯π(phen-yl) and phenyl-C-H⋯π(hy-droxy-benzene) inter-actions. The layers stack without directional inter-actions between them. The analysis of the calculated Hirshfeld surface highlights the presence of weak methyl-C-H⋯O(hydrox-yl) and H⋯H inter-actions in the inter-layer region. Computational chemistry indicates that dispersion energy is the major contributor to the overall stabilization of the mol-ecular packing. |
| first_indexed | 2025-11-14T21:18:32Z |
| format | Article |
| id | sunway-1792 |
| institution | Sunway University |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T21:18:32Z |
| publishDate | 2021 |
| publisher | International Union of Crystallography |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | sunway-17922021-12-01T01:50:33Z http://eprints.sunway.edu.my/1792/ 1-{(E)-[4-(4-Hydroxyphenyl)butan-2-ylidene]amino}-3-phenylthiourea: crystal structure, Hirshfeld surface analysis and computational study Tan, Ming Yueh Kwong, Huey Chong * Crouse, Karen A. Ravoof, Thahira Begum S. A. Tiekink, Edward R. T. * QD Chemistry The title thio-urea derivative, C17H19N3OS, adopts a U-shaped conformation with the dihedral angle between the terminal aromatic rings being 73.64 (5)°. The major twist in the mol-ecule occurs about the ethane bond with the Ci-Ce-Ce-Cb torsion angle being -78.12 (18)°; i = imine, e = ethane and b = benzene. The configuration about the imine bond is E, the N-bound H atoms lie on opposite sides of the mol-ecule and an intra-molecular amine-N-H⋯N(imine) hydrogen bond is evident. In the mol-ecular packing, hydroxyl-O-H⋯S(thione) and amine-N-H⋯O hydrogen bonding feature within a linear, supra-molecular chain. The chains are connected into a layer in the ab plane by a combination of methyl-ene-C-H⋯S(thione), methyl-ene-C-H⋯O(hydrox-yl), methyl-C-H⋯π(phen-yl) and phenyl-C-H⋯π(hy-droxy-benzene) inter-actions. The layers stack without directional inter-actions between them. The analysis of the calculated Hirshfeld surface highlights the presence of weak methyl-C-H⋯O(hydrox-yl) and H⋯H inter-actions in the inter-layer region. Computational chemistry indicates that dispersion energy is the major contributor to the overall stabilization of the mol-ecular packing. International Union of Crystallography 2021 Article PeerReviewed text en cc_by_nc_4 http://eprints.sunway.edu.my/1792/1/Tiekink%20acta%20cryst%202021%20e77%20788.pdf Tan, Ming Yueh and Kwong, Huey Chong * and Crouse, Karen A. and Ravoof, Thahira Begum S. A. and Tiekink, Edward R. T. * (2021) 1-{(E)-[4-(4-Hydroxyphenyl)butan-2-ylidene]amino}-3-phenylthiourea: crystal structure, Hirshfeld surface analysis and computational study. Acta Crystallographica Section E Crystallographic Communications, 77 (8). pp. 788-794. ISSN 2056-9890 http://doi.org/10.1107/S2056989021006666 doi:10.1107/S2056989021006666 |
| spellingShingle | QD Chemistry Tan, Ming Yueh Kwong, Huey Chong * Crouse, Karen A. Ravoof, Thahira Begum S. A. Tiekink, Edward R. T. * 1-{(E)-[4-(4-Hydroxyphenyl)butan-2-ylidene]amino}-3-phenylthiourea: crystal structure, Hirshfeld surface analysis and computational study |
| title | 1-{(E)-[4-(4-Hydroxyphenyl)butan-2-ylidene]amino}-3-phenylthiourea: crystal structure, Hirshfeld surface analysis and computational study |
| title_full | 1-{(E)-[4-(4-Hydroxyphenyl)butan-2-ylidene]amino}-3-phenylthiourea: crystal structure, Hirshfeld surface analysis and computational study |
| title_fullStr | 1-{(E)-[4-(4-Hydroxyphenyl)butan-2-ylidene]amino}-3-phenylthiourea: crystal structure, Hirshfeld surface analysis and computational study |
| title_full_unstemmed | 1-{(E)-[4-(4-Hydroxyphenyl)butan-2-ylidene]amino}-3-phenylthiourea: crystal structure, Hirshfeld surface analysis and computational study |
| title_short | 1-{(E)-[4-(4-Hydroxyphenyl)butan-2-ylidene]amino}-3-phenylthiourea: crystal structure, Hirshfeld surface analysis and computational study |
| title_sort | 1-{(e)-[4-(4-hydroxyphenyl)butan-2-ylidene]amino}-3-phenylthiourea: crystal structure, hirshfeld surface analysis and computational study |
| topic | QD Chemistry |
| url | http://eprints.sunway.edu.my/1792/ http://eprints.sunway.edu.my/1792/ http://eprints.sunway.edu.my/1792/ http://eprints.sunway.edu.my/1792/1/Tiekink%20acta%20cryst%202021%20e77%20788.pdf |