Zwitterionic 4-bromo-6-methoxy-2-{[tris(hydroxymethyl)methyl]iminiumylmethyl}phenolate: crystal structure and Hirshfeld surface analysis
In the solid state, the title compound, C12H16BrNO5 [systematic name: 4-bromo-2-((1E)-{[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]iminiumyl}methyl)-6-methoxybenzen-1-olate], C12H16BrNO5, is found in the keto-amine tautomeric form, with an intramolecular iminium-N-H...O(phenolate) hydrogen...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2016
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| Online Access: | http://eprints.sunway.edu.my/646/ http://eprints.sunway.edu.my/646/1/Acta%20E_RC%202016%201223.pdf |
| _version_ | 1848801868285739008 |
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| author | Lee, See Mun * Lo, Kong Mun * Tan, Sang Loon * Tiekink, Edward R. T. * |
| author_facet | Lee, See Mun * Lo, Kong Mun * Tan, Sang Loon * Tiekink, Edward R. T. * |
| author_sort | Lee, See Mun * |
| building | SU Institutional Repository |
| collection | Online Access |
| description | In the solid state, the title compound, C12H16BrNO5 [systematic name: 4-bromo-2-((1E)-{[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]iminiumyl}methyl)-6-methoxybenzen-1-olate], C12H16BrNO5, is found in the keto-amine tautomeric form, with an intramolecular iminium-N-H...O(phenolate) hydrogen bond and an E conformation about the C=N bond. Both gauche (two) and anti relationships are found for the methylhydroxy groups. In the crystal, a supramolecular layer in the bc plane is formed via hydroxy-O-H...O(hydroxy) and charge-assisted hydroxy-O-H...O(phenolate) hydrogen-bonding interactions; various C-H...O interactions provide additional cohesion to the layers, which stack along the a axis with no directional interactions between them. A Hirshfeld surface analysis confirms the lack of specific interactions in the inter-layer region. |
| first_indexed | 2025-11-14T21:14:17Z |
| format | Article |
| id | sunway-646 |
| institution | Sunway University |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T21:14:17Z |
| publishDate | 2016 |
| publisher | International Union of Crystallography |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | sunway-6462020-10-12T07:28:09Z http://eprints.sunway.edu.my/646/ Zwitterionic 4-bromo-6-methoxy-2-{[tris(hydroxymethyl)methyl]iminiumylmethyl}phenolate: crystal structure and Hirshfeld surface analysis Lee, See Mun * Lo, Kong Mun * Tan, Sang Loon * Tiekink, Edward R. T. * QD Chemistry In the solid state, the title compound, C12H16BrNO5 [systematic name: 4-bromo-2-((1E)-{[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]iminiumyl}methyl)-6-methoxybenzen-1-olate], C12H16BrNO5, is found in the keto-amine tautomeric form, with an intramolecular iminium-N-H...O(phenolate) hydrogen bond and an E conformation about the C=N bond. Both gauche (two) and anti relationships are found for the methylhydroxy groups. In the crystal, a supramolecular layer in the bc plane is formed via hydroxy-O-H...O(hydroxy) and charge-assisted hydroxy-O-H...O(phenolate) hydrogen-bonding interactions; various C-H...O interactions provide additional cohesion to the layers, which stack along the a axis with no directional interactions between them. A Hirshfeld surface analysis confirms the lack of specific interactions in the inter-layer region. International Union of Crystallography 2016 Article PeerReviewed text en http://eprints.sunway.edu.my/646/1/Acta%20E_RC%202016%201223.pdf Lee, See Mun * and Lo, Kong Mun * and Tan, Sang Loon * and Tiekink, Edward R. T. * (2016) Zwitterionic 4-bromo-6-methoxy-2-{[tris(hydroxymethyl)methyl]iminiumylmethyl}phenolate: crystal structure and Hirshfeld surface analysis. Acta Crystallographica Section E Crystallographic Communications, 72 (8). pp. 1223-1227. ISSN 2056-9890 http://dx.doi.org/10.1107/S2056989016012159 doi:10.1107/S2056989016012159 |
| spellingShingle | QD Chemistry Lee, See Mun * Lo, Kong Mun * Tan, Sang Loon * Tiekink, Edward R. T. * Zwitterionic 4-bromo-6-methoxy-2-{[tris(hydroxymethyl)methyl]iminiumylmethyl}phenolate: crystal structure and Hirshfeld surface analysis |
| title | Zwitterionic 4-bromo-6-methoxy-2-{[tris(hydroxymethyl)methyl]iminiumylmethyl}phenolate: crystal structure and Hirshfeld surface analysis |
| title_full | Zwitterionic 4-bromo-6-methoxy-2-{[tris(hydroxymethyl)methyl]iminiumylmethyl}phenolate: crystal structure and Hirshfeld surface analysis |
| title_fullStr | Zwitterionic 4-bromo-6-methoxy-2-{[tris(hydroxymethyl)methyl]iminiumylmethyl}phenolate: crystal structure and Hirshfeld surface analysis |
| title_full_unstemmed | Zwitterionic 4-bromo-6-methoxy-2-{[tris(hydroxymethyl)methyl]iminiumylmethyl}phenolate: crystal structure and Hirshfeld surface analysis |
| title_short | Zwitterionic 4-bromo-6-methoxy-2-{[tris(hydroxymethyl)methyl]iminiumylmethyl}phenolate: crystal structure and Hirshfeld surface analysis |
| title_sort | zwitterionic 4-bromo-6-methoxy-2-{[tris(hydroxymethyl)methyl]iminiumylmethyl}phenolate: crystal structure and hirshfeld surface analysis |
| topic | QD Chemistry |
| url | http://eprints.sunway.edu.my/646/ http://eprints.sunway.edu.my/646/ http://eprints.sunway.edu.my/646/ http://eprints.sunway.edu.my/646/1/Acta%20E_RC%202016%201223.pdf |