Cargando…
Different classical hydrogen-bonding patterns in three salicylaldoxime derivatives, 2-HO-4-XC(6)H(3)C=NOH (X = Me, OH and MeO)
The crystal structures of three salicyaldoxime compounds, namely 2-hydroxy-4-methylbenzaldehyde oxime, C(8)H(9)NO(2), 1, 2,4-dihydroxybenzaldehyde oxime, C(7)H(7)NO(3), 2, and 2-hydroxy-4-methoxybenzaldehyde oxime, C(8)H(9)NO(3), 3, are discussed. In each compound, the hydroxyl groups are ess...
Autores principales: | , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2018
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6176434/ https://www.ncbi.nlm.nih.gov/pubmed/30319806 http://dx.doi.org/10.1107/S2056989018013361 |
_version_ | 1783361701405523968 |
---|---|
author | Gomes, Ligia R. de Souza, Marcus V. N. Da Costa, Cristiane F. Wardell, James L. Low, John Nicolson |
author_facet | Gomes, Ligia R. de Souza, Marcus V. N. Da Costa, Cristiane F. Wardell, James L. Low, John Nicolson |
author_sort | Gomes, Ligia R. |
collection | PubMed |
description | The crystal structures of three salicyaldoxime compounds, namely 2-hydroxy-4-methylbenzaldehyde oxime, C(8)H(9)NO(2), 1, 2,4-dihydroxybenzaldehyde oxime, C(7)H(7)NO(3), 2, and 2-hydroxy-4-methoxybenzaldehyde oxime, C(8)H(9)NO(3), 3, are discussed. In each compound, the hydroxyl groups are essentially coplanar with their attached phenyl group. The interplanar angles between the C=N—O moieties of the oxime unit and their attached phenyl rings are 0.08 (9), 1.08 (15) and 6.65 (15)° in 1, 2 and 3, respectively. In all three molecules, the 2-hydroxy group forms an intramolecular O—H⋯N(oxime) hydrogen bond. In compound (1), intermolecular O—H(oxime)⋯O(hydroxyl) hydrogen bonds generate R (2) (2)(14) dimers, related by inversion centres. In compound 2, intermolecular O—H(oxime)⋯O(4-hydroxy) hydrogen bonds generate C9 chains along the b-axis direction, while O—H(4-hydroxyl)⋯O(2-hydroxyl) interactions form zigzag C6 spiral chains along the c-axis direction, generated by a screw axis at 1, y, 1/4: the combination of the two chains provides a bimolecular sheet running parallel to the b axis, which lies between 0–1/2 c and 1/2–1 c. In compound 3, similar C9 chains, along the b-axis direction are generated by O—H(oxime)⋯O(4-methoxy) hydrogen bonds. Further weaker, C—H⋯π (in 1), π–π (in 2) and both C—H⋯π and π–π interactions (in 3) further cement the three-dimensional structures. Hirshfeld surface and fingerprint analyses are discussed. |
format | Online Article Text |
id | pubmed-6176434 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-61764342018-10-12 Different classical hydrogen-bonding patterns in three salicylaldoxime derivatives, 2-HO-4-XC(6)H(3)C=NOH (X = Me, OH and MeO) Gomes, Ligia R. de Souza, Marcus V. N. Da Costa, Cristiane F. Wardell, James L. Low, John Nicolson Acta Crystallogr E Crystallogr Commun Research Communications The crystal structures of three salicyaldoxime compounds, namely 2-hydroxy-4-methylbenzaldehyde oxime, C(8)H(9)NO(2), 1, 2,4-dihydroxybenzaldehyde oxime, C(7)H(7)NO(3), 2, and 2-hydroxy-4-methoxybenzaldehyde oxime, C(8)H(9)NO(3), 3, are discussed. In each compound, the hydroxyl groups are essentially coplanar with their attached phenyl group. The interplanar angles between the C=N—O moieties of the oxime unit and their attached phenyl rings are 0.08 (9), 1.08 (15) and 6.65 (15)° in 1, 2 and 3, respectively. In all three molecules, the 2-hydroxy group forms an intramolecular O—H⋯N(oxime) hydrogen bond. In compound (1), intermolecular O—H(oxime)⋯O(hydroxyl) hydrogen bonds generate R (2) (2)(14) dimers, related by inversion centres. In compound 2, intermolecular O—H(oxime)⋯O(4-hydroxy) hydrogen bonds generate C9 chains along the b-axis direction, while O—H(4-hydroxyl)⋯O(2-hydroxyl) interactions form zigzag C6 spiral chains along the c-axis direction, generated by a screw axis at 1, y, 1/4: the combination of the two chains provides a bimolecular sheet running parallel to the b axis, which lies between 0–1/2 c and 1/2–1 c. In compound 3, similar C9 chains, along the b-axis direction are generated by O—H(oxime)⋯O(4-methoxy) hydrogen bonds. Further weaker, C—H⋯π (in 1), π–π (in 2) and both C—H⋯π and π–π interactions (in 3) further cement the three-dimensional structures. Hirshfeld surface and fingerprint analyses are discussed. International Union of Crystallography 2018-09-25 /pmc/articles/PMC6176434/ /pubmed/30319806 http://dx.doi.org/10.1107/S2056989018013361 Text en © Gomes et al. 2018 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/2.0/uk/ |
spellingShingle | Research Communications Gomes, Ligia R. de Souza, Marcus V. N. Da Costa, Cristiane F. Wardell, James L. Low, John Nicolson Different classical hydrogen-bonding patterns in three salicylaldoxime derivatives, 2-HO-4-XC(6)H(3)C=NOH (X = Me, OH and MeO) |
title | Different classical hydrogen-bonding patterns in three salicylaldoxime derivatives, 2-HO-4-XC(6)H(3)C=NOH (X = Me, OH and MeO) |
title_full | Different classical hydrogen-bonding patterns in three salicylaldoxime derivatives, 2-HO-4-XC(6)H(3)C=NOH (X = Me, OH and MeO) |
title_fullStr | Different classical hydrogen-bonding patterns in three salicylaldoxime derivatives, 2-HO-4-XC(6)H(3)C=NOH (X = Me, OH and MeO) |
title_full_unstemmed | Different classical hydrogen-bonding patterns in three salicylaldoxime derivatives, 2-HO-4-XC(6)H(3)C=NOH (X = Me, OH and MeO) |
title_short | Different classical hydrogen-bonding patterns in three salicylaldoxime derivatives, 2-HO-4-XC(6)H(3)C=NOH (X = Me, OH and MeO) |
title_sort | different classical hydrogen-bonding patterns in three salicylaldoxime derivatives, 2-ho-4-xc(6)h(3)c=noh (x = me, oh and meo) |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6176434/ https://www.ncbi.nlm.nih.gov/pubmed/30319806 http://dx.doi.org/10.1107/S2056989018013361 |
work_keys_str_mv | AT gomesligiar differentclassicalhydrogenbondingpatternsinthreesalicylaldoximederivatives2ho4xc6h3cnohxmeohandmeo AT desouzamarcusvn differentclassicalhydrogenbondingpatternsinthreesalicylaldoximederivatives2ho4xc6h3cnohxmeohandmeo AT dacostacristianef differentclassicalhydrogenbondingpatternsinthreesalicylaldoximederivatives2ho4xc6h3cnohxmeohandmeo AT wardelljamesl differentclassicalhydrogenbondingpatternsinthreesalicylaldoximederivatives2ho4xc6h3cnohxmeohandmeo AT lowjohnnicolson differentclassicalhydrogenbondingpatternsinthreesalicylaldoximederivatives2ho4xc6h3cnohxmeohandmeo |