2-Methyl-4-(4-nitrophenyl)but-3-yn-2-ol: crystal structure, Hirshfeld surface analysis and computational chemistry study
The di-substituted acetylene residue in the title compound, C11H11NO3, is capped at either end by di-methylhydroxy and 4-nitrobenzene groups; the nitro substituent is close to co-planar with the ring to which it is attached [dihedral angle = 9.4 (3)]. The most prominent feature of the molecular pac...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2019
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| Online Access: | http://eprints.sunway.edu.my/1075/ http://eprints.sunway.edu.my/1075/1/Tiekink%202%20Methyl%204%20%20nitrophenyl%20Acta%20E75%202019%201232.pdf |
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| author | Caracelli, Ignez Zukerman-Schpector, Julio Schwab, Ricardo S Silva, Everton M Jotani, Mukesh M. Tiekink, Edward R. T. * |
| author_facet | Caracelli, Ignez Zukerman-Schpector, Julio Schwab, Ricardo S Silva, Everton M Jotani, Mukesh M. Tiekink, Edward R. T. * |
| author_sort | Caracelli, Ignez |
| building | SU Institutional Repository |
| collection | Online Access |
| description | The di-substituted acetylene residue in the title compound, C11H11NO3, is capped at either end by di-methylhydroxy and 4-nitrobenzene groups; the nitro substituent is close to co-planar with the ring to which it is attached [dihedral
angle = 9.4 (3)]. The most prominent feature of the molecular packing is the formation, via hydroxy-O—HO(hydroxy) hydrogen bonds, of hexameric clusters about a site of symmetry 3. The aggregates are sustained by 12-
membered {OH}6 synthons and have the shape of a flattened chair. The clusters are connected into a three-dimensional architecture by benzene-C—HO(nitro) interactions, involving both nitro-O atoms. The aforementioned interactions are readily identified in the calculated Hirshfeld surface.
Computational chemistry indicates there is a significant energy, primarily electrostatic in nature, associated with the hydroxy-O—HO(hydroxy) hydrogen bonds. Dispersion forces are more important in the other identified but, weaker intermolecular contacts. |
| first_indexed | 2025-11-14T21:15:54Z |
| format | Article |
| id | sunway-1075 |
| institution | Sunway University |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T21:15:54Z |
| publishDate | 2019 |
| publisher | International Union of Crystallography |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | sunway-10752020-10-07T08:33:59Z http://eprints.sunway.edu.my/1075/ 2-Methyl-4-(4-nitrophenyl)but-3-yn-2-ol: crystal structure, Hirshfeld surface analysis and computational chemistry study Caracelli, Ignez Zukerman-Schpector, Julio Schwab, Ricardo S Silva, Everton M Jotani, Mukesh M. Tiekink, Edward R. T. * QD Chemistry The di-substituted acetylene residue in the title compound, C11H11NO3, is capped at either end by di-methylhydroxy and 4-nitrobenzene groups; the nitro substituent is close to co-planar with the ring to which it is attached [dihedral angle = 9.4 (3)]. The most prominent feature of the molecular packing is the formation, via hydroxy-O—HO(hydroxy) hydrogen bonds, of hexameric clusters about a site of symmetry 3. The aggregates are sustained by 12- membered {OH}6 synthons and have the shape of a flattened chair. The clusters are connected into a three-dimensional architecture by benzene-C—HO(nitro) interactions, involving both nitro-O atoms. The aforementioned interactions are readily identified in the calculated Hirshfeld surface. Computational chemistry indicates there is a significant energy, primarily electrostatic in nature, associated with the hydroxy-O—HO(hydroxy) hydrogen bonds. Dispersion forces are more important in the other identified but, weaker intermolecular contacts. International Union of Crystallography 2019-07-18 Article PeerReviewed text en cc_by_nc_4 http://eprints.sunway.edu.my/1075/1/Tiekink%202%20Methyl%204%20%20nitrophenyl%20Acta%20E75%202019%201232.pdf Caracelli, Ignez and Zukerman-Schpector, Julio and Schwab, Ricardo S and Silva, Everton M and Jotani, Mukesh M. and Tiekink, Edward R. T. * (2019) 2-Methyl-4-(4-nitrophenyl)but-3-yn-2-ol: crystal structure, Hirshfeld surface analysis and computational chemistry study. Acta Crystallographica Section E Crystallographic Communications, 75 (8). pp. 1232-1238. ISSN 2056-9890 (In Press) http://doi.org/10.1107/S2056989019010284 doi:10.1107/S2056989019010284 |
| spellingShingle | QD Chemistry Caracelli, Ignez Zukerman-Schpector, Julio Schwab, Ricardo S Silva, Everton M Jotani, Mukesh M. Tiekink, Edward R. T. * 2-Methyl-4-(4-nitrophenyl)but-3-yn-2-ol: crystal structure, Hirshfeld surface analysis and computational chemistry study |
| title | 2-Methyl-4-(4-nitrophenyl)but-3-yn-2-ol: crystal structure, Hirshfeld surface analysis and computational chemistry study |
| title_full | 2-Methyl-4-(4-nitrophenyl)but-3-yn-2-ol: crystal structure, Hirshfeld surface analysis and computational chemistry study |
| title_fullStr | 2-Methyl-4-(4-nitrophenyl)but-3-yn-2-ol: crystal structure, Hirshfeld surface analysis and computational chemistry study |
| title_full_unstemmed | 2-Methyl-4-(4-nitrophenyl)but-3-yn-2-ol: crystal structure, Hirshfeld surface analysis and computational chemistry study |
| title_short | 2-Methyl-4-(4-nitrophenyl)but-3-yn-2-ol: crystal structure, Hirshfeld surface analysis and computational chemistry study |
| title_sort | 2-methyl-4-(4-nitrophenyl)but-3-yn-2-ol: crystal structure, hirshfeld surface analysis and computational chemistry study |
| topic | QD Chemistry |
| url | http://eprints.sunway.edu.my/1075/ http://eprints.sunway.edu.my/1075/ http://eprints.sunway.edu.my/1075/ http://eprints.sunway.edu.my/1075/1/Tiekink%202%20Methyl%204%20%20nitrophenyl%20Acta%20E75%202019%201232.pdf |