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Structural study of three heteroaryl oximes, heteroaryl-N=OH: Compounds forming strong C3 molecular chains
John Nicolson Low (1)
, James Lewis Wardell (2) , Cristiane Franca da Costa (3) , Marcus Vicinius Nora Souza (4) , Ligia Rebelo Gomes (5,*) (1) Department of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen, AB24 3UE, Scotland
(2) Department of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen, AB24 3UE, Scotland
(3) Instituto de Tecnologia em Fármacos e Farmanguinhos, Fundação Oswaldo Cruz, 21041-250 Rio de Janeiro, Rio de Janeiro, Brazil
(4) Instituto de Tecnologia em Fármacos e Farmanguinhos, Fundação Oswaldo Cruz, 21041-250 Rio de Janeiro, Rio de Janeiro, Brazil
(5) FP-ENAS-Faculdade de Ciências de Saúde, Escola Superior de Saúde da UFP, Universidade Fernando Pessoa, Rua Carlos da Maia, 296, P-4200-150 Porto, Portugal
(*) Corresponding Author
Received: 14 May 2018 | Revised: 04 Jun 2018 | Accepted: 05 Jun 2018 | Published: 30 Sep 2018 | Issue Date: September 2018
Abstract
In order to further investigate the structural chemistry of oximes and to further establish the main structural arrangements adopted, we have determined the crystal structure of and carried out Hirshfeld surface calculations on three heteroaryl oximes, namely (Z)-thiophene-2-carbaldehyde oxime (1), (Z)-1H-pyrrole-2 carbaldehyde oxime (2) and (Z)-5-nitrofuran-2-carbaldehyde oxime (3). As confirmed by both techniques, the major intermolecular interactions in each compound are classical N—H···O hydrogen bonds, which link the molecules into C3 chains. Such an arrangement has been previous reported as an important aggregation mode for oximes. Secondary interactions, C—H···π and C—H···O interactions, in compounds 1 and 2, and interactions involving the nitro group oxygen atoms in compound 3 link the chains into three dimensional arrays.
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DOI: 10.5155/eurjchem.9.3.151-160.1734
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Funding information
Portuguese Foundation for Science and Technology (FCT) UID/Multi/04546/2013
Citations
[1]. Ligia R. Gomes, John N. Low, Tanja van Mourik, Herbert Früchtl, Marcus V.N. de Souza, Cristiane F. da Costa, James L. Wardell
Different substituent effects on the supramolecular arrays in some (E)-halo- and nitro-benzaldehyde oximes: confirmation of attractive π(C=N)···π(phenyl) interactions
Zeitschrift für Naturforschung B 74(4), 319, 2019
DOI: 10.1515/znb-2018-0222
[2]. Ligia R. Gomes, Marcus V. N. de Souza, Cristiane F. Da Costa, James L. Wardell, John Nicolson Low
Crystal structures and Hirshfeld surfaces of four methoxybenzaldehyde oxime derivatives, 2-MeO-XC6H3C=NOH (X = H and 2-, 3- and 4-MeO): different conformations and hydrogen-bonding patterns
Acta Crystallographica Section E Crystallographic Communications 74(11), 1553, 2018
DOI: 10.1107/S2056989018014020
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DOI Link: https://doi.org/10.5155/eurjchem.9.3.151-160.1734
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European Journal of Chemistry 2018, 9(3), 151-160 | doi: https://doi.org/10.5155/eurjchem.9.3.151-160.1734 | Get rights and content
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