2-Methyl-4-(4-nitrophenyl)but-3-yn-2-ol: crystal structure, Hirshfeld surface analysis and computational chemistry study

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)

Tiekink 2 Methyl 4 nitrophenyl Acta E75 2019 1232.pdf - Accepted Version
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Official URL: http://doi.org/10.1107/S2056989019010284


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.

Item Type: Article
Uncontrolled Keywords: crystal structure; acetylene; hydrogen bonding; Hirshfeld surface analysis; NCI plots; computational chemistry.
Subjects: Q Science > QD Chemistry
Divisions: Others > Non Sunway Academics
Sunway University > School of Engineering and Technology [formerly School of Science and Technology until 2020] > Research Centre for Crystalline Materials moved to SMLS wef 2021
Depositing User: Dr Janaki Sinnasamy
Related URLs:
Date Deposited: 29 Jul 2019 09:20
Last Modified: 07 Oct 2020 08:33
URI: http://eprints.sunway.edu.my/id/eprint/1075

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