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
Autor(a) principal: | |
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Data de Publicação: | 2018 |
Outros Autores: | , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | http://hdl.handle.net/10284/8176 |
Resumo: | The crystal structures of four (E)-meth-oxy-benzaldehyde oxime derivatives, namely (2-meth-oxy-benzaldehyde oxime, 1, 2,3-di-meth-oxy-benzaldehyde oxime, 2, 4-di-meth-oxy-benzaldehyde oxime, 3, and 2,5-di-meth-oxy-benzaldehyde oxime, 4, are discussed. The arrangements of the 2-meth-oxy group and the H atom of the oxime unit are s-cis in compounds 1-3, but in both independent mol-ecules of compound 4, the arrangements are s-trans. There is also a difference in the conformation of the two mol-ecules in 4, involving the orientations of the 2- and 5-meth-oxy groups. The primary inter-molecular O-H(oxime)⋯O(hy-droxy) hydrogen bonds generate C(3) chains in 1 and 2. In contrast, in compound 3, the O-H(oxime)⋯O(hy-droxy) hydrogen bonds generate symmetric R22(6) dimers. A more complex dimer is generated in 4 from the O-H(oxime)⋯O(hy-droxy) and C-H(2-meth-oxy)⋯O(hy-droxy) hydrogen bonds. In all cases, further inter-actions, C-H⋯O and C-H⋯π or π-π, generate three-dimensional arrays. Hirshfeld surface and fingerprint analyses are discussed. |
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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 patternsCrystal structureOxime derivativeHydrogen bondingThe crystal structures of four (E)-meth-oxy-benzaldehyde oxime derivatives, namely (2-meth-oxy-benzaldehyde oxime, 1, 2,3-di-meth-oxy-benzaldehyde oxime, 2, 4-di-meth-oxy-benzaldehyde oxime, 3, and 2,5-di-meth-oxy-benzaldehyde oxime, 4, are discussed. The arrangements of the 2-meth-oxy group and the H atom of the oxime unit are s-cis in compounds 1-3, but in both independent mol-ecules of compound 4, the arrangements are s-trans. There is also a difference in the conformation of the two mol-ecules in 4, involving the orientations of the 2- and 5-meth-oxy groups. The primary inter-molecular O-H(oxime)⋯O(hy-droxy) hydrogen bonds generate C(3) chains in 1 and 2. In contrast, in compound 3, the O-H(oxime)⋯O(hy-droxy) hydrogen bonds generate symmetric R22(6) dimers. A more complex dimer is generated in 4 from the O-H(oxime)⋯O(hy-droxy) and C-H(2-meth-oxy)⋯O(hy-droxy) hydrogen bonds. In all cases, further inter-actions, C-H⋯O and C-H⋯π or π-π, generate three-dimensional arrays. Hirshfeld surface and fingerprint analyses are discussed.International Union of CrystallographyRepositório Institucional da Universidade Fernando PessoaGomes, Ligia R.Souza, Marcus V. N. deDa Costa, Cristiane F.Wardell, James L.Low, John Nicolson2019-10-24T18:51:35Z2018-01-01T00:00:00Z2018-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10284/8176engGomes, L. R., de Souza, M., Da Costa, C. F., Wardell, J. L., & Low, J. N. (2018). Crystal structures and Hirshfeld surfaces of four meth-oxy-benzaldehyde 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(Pt 11), 1553–1560. doi:10.1107/S20569890180140202056-989010.1107/S2056989018014020info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2022-09-06T02:07:33Zoai:bdigital.ufp.pt:10284/8176Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T15:45:03.899062Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse |
dc.title.none.fl_str_mv |
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 |
title |
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 |
spellingShingle |
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 Gomes, Ligia R. Crystal structure Oxime derivative Hydrogen bonding |
title_short |
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 |
title_full |
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 |
title_fullStr |
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 |
title_full_unstemmed |
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 |
title_sort |
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 |
author |
Gomes, Ligia R. |
author_facet |
Gomes, Ligia R. Souza, Marcus V. N. de Da Costa, Cristiane F. Wardell, James L. Low, John Nicolson |
author_role |
author |
author2 |
Souza, Marcus V. N. de Da Costa, Cristiane F. Wardell, James L. Low, John Nicolson |
author2_role |
author author author author |
dc.contributor.none.fl_str_mv |
Repositório Institucional da Universidade Fernando Pessoa |
dc.contributor.author.fl_str_mv |
Gomes, Ligia R. Souza, Marcus V. N. de Da Costa, Cristiane F. Wardell, James L. Low, John Nicolson |
dc.subject.por.fl_str_mv |
Crystal structure Oxime derivative Hydrogen bonding |
topic |
Crystal structure Oxime derivative Hydrogen bonding |
description |
The crystal structures of four (E)-meth-oxy-benzaldehyde oxime derivatives, namely (2-meth-oxy-benzaldehyde oxime, 1, 2,3-di-meth-oxy-benzaldehyde oxime, 2, 4-di-meth-oxy-benzaldehyde oxime, 3, and 2,5-di-meth-oxy-benzaldehyde oxime, 4, are discussed. The arrangements of the 2-meth-oxy group and the H atom of the oxime unit are s-cis in compounds 1-3, but in both independent mol-ecules of compound 4, the arrangements are s-trans. There is also a difference in the conformation of the two mol-ecules in 4, involving the orientations of the 2- and 5-meth-oxy groups. The primary inter-molecular O-H(oxime)⋯O(hy-droxy) hydrogen bonds generate C(3) chains in 1 and 2. In contrast, in compound 3, the O-H(oxime)⋯O(hy-droxy) hydrogen bonds generate symmetric R22(6) dimers. A more complex dimer is generated in 4 from the O-H(oxime)⋯O(hy-droxy) and C-H(2-meth-oxy)⋯O(hy-droxy) hydrogen bonds. In all cases, further inter-actions, C-H⋯O and C-H⋯π or π-π, generate three-dimensional arrays. Hirshfeld surface and fingerprint analyses are discussed. |
publishDate |
2018 |
dc.date.none.fl_str_mv |
2018-01-01T00:00:00Z 2018-01-01T00:00:00Z 2019-10-24T18:51:35Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://hdl.handle.net/10284/8176 |
url |
http://hdl.handle.net/10284/8176 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Gomes, L. R., de Souza, M., Da Costa, C. F., Wardell, J. L., & Low, J. N. (2018). Crystal structures and Hirshfeld surfaces of four meth-oxy-benzaldehyde 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(Pt 11), 1553–1560. doi:10.1107/S2056989018014020 2056-9890 10.1107/S2056989018014020 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf |
dc.publisher.none.fl_str_mv |
International Union of Crystallography |
publisher.none.fl_str_mv |
International Union of Crystallography |
dc.source.none.fl_str_mv |
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Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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