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Crystal structure of (E)-2-[(2-bromopyridin-3-yl)methylidene]-6-methoxy-3,4-dihydronaphthalen-1(2H)-one and 3-[(E)-(6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalen-2-ylidene)methyl]pyridin-2(1H)-one
The title compounds C(17)H(14)BrNO(2), (I), and C(17)H(15)NO(3), (II), were obtained from the reaction of 6-methoxy-3,4-dihydro-2H-naphthalen-1-one and 2-bromonicotinaldehyde in ethanol. Compound (I) was the expected product and compound (II) was the oxidation product from air exposure. In the cr...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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International Union of Crystallography
2016
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4992914/ https://www.ncbi.nlm.nih.gov/pubmed/27555939 http://dx.doi.org/10.1107/S2056989016009300 |
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author | Zingales, Sarah K. Moore, Morgan E. Goetz, Andrew D. Padgett, Clifford W. |
author_facet | Zingales, Sarah K. Moore, Morgan E. Goetz, Andrew D. Padgett, Clifford W. |
author_sort | Zingales, Sarah K. |
collection | PubMed |
description | The title compounds C(17)H(14)BrNO(2), (I), and C(17)H(15)NO(3), (II), were obtained from the reaction of 6-methoxy-3,4-dihydro-2H-naphthalen-1-one and 2-bromonicotinaldehyde in ethanol. Compound (I) was the expected product and compound (II) was the oxidation product from air exposure. In the crystal structure of compound (I), there are no short contacts or hydrogen bonds. The structure does display π–π interactions between adjacent benzene rings and adjacent pyridyl rings. Compound (II) contains two independent molecules, A and B, in the asymmetric unit; both are non-planar, the dihedral angles between the methoxybenzene and 1H-pyridin-2-one mean planes being 35.07 (9)° in A and 35.28 (9)°in B. In each molecule, the 1H-pyridin-2-one unit participates in intermolecular N—H⋯O hydrogen bonding to another molecule of the same type (A to A or B to B). The structure also displays π–π interactions between the pyridyl and the benzene rings of non-equivalent molecules (viz., A to B and B to A). |
format | Online Article Text |
id | pubmed-4992914 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-49929142016-08-23 Crystal structure of (E)-2-[(2-bromopyridin-3-yl)methylidene]-6-methoxy-3,4-dihydronaphthalen-1(2H)-one and 3-[(E)-(6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalen-2-ylidene)methyl]pyridin-2(1H)-one Zingales, Sarah K. Moore, Morgan E. Goetz, Andrew D. Padgett, Clifford W. Acta Crystallogr E Crystallogr Commun Research Communications The title compounds C(17)H(14)BrNO(2), (I), and C(17)H(15)NO(3), (II), were obtained from the reaction of 6-methoxy-3,4-dihydro-2H-naphthalen-1-one and 2-bromonicotinaldehyde in ethanol. Compound (I) was the expected product and compound (II) was the oxidation product from air exposure. In the crystal structure of compound (I), there are no short contacts or hydrogen bonds. The structure does display π–π interactions between adjacent benzene rings and adjacent pyridyl rings. Compound (II) contains two independent molecules, A and B, in the asymmetric unit; both are non-planar, the dihedral angles between the methoxybenzene and 1H-pyridin-2-one mean planes being 35.07 (9)° in A and 35.28 (9)°in B. In each molecule, the 1H-pyridin-2-one unit participates in intermolecular N—H⋯O hydrogen bonding to another molecule of the same type (A to A or B to B). The structure also displays π–π interactions between the pyridyl and the benzene rings of non-equivalent molecules (viz., A to B and B to A). International Union of Crystallography 2016-06-14 /pmc/articles/PMC4992914/ /pubmed/27555939 http://dx.doi.org/10.1107/S2056989016009300 Text en © Zingales et al. 2016 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 Zingales, Sarah K. Moore, Morgan E. Goetz, Andrew D. Padgett, Clifford W. Crystal structure of (E)-2-[(2-bromopyridin-3-yl)methylidene]-6-methoxy-3,4-dihydronaphthalen-1(2H)-one and 3-[(E)-(6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalen-2-ylidene)methyl]pyridin-2(1H)-one |
title | Crystal structure of (E)-2-[(2-bromopyridin-3-yl)methylidene]-6-methoxy-3,4-dihydronaphthalen-1(2H)-one and 3-[(E)-(6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalen-2-ylidene)methyl]pyridin-2(1H)-one |
title_full | Crystal structure of (E)-2-[(2-bromopyridin-3-yl)methylidene]-6-methoxy-3,4-dihydronaphthalen-1(2H)-one and 3-[(E)-(6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalen-2-ylidene)methyl]pyridin-2(1H)-one |
title_fullStr | Crystal structure of (E)-2-[(2-bromopyridin-3-yl)methylidene]-6-methoxy-3,4-dihydronaphthalen-1(2H)-one and 3-[(E)-(6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalen-2-ylidene)methyl]pyridin-2(1H)-one |
title_full_unstemmed | Crystal structure of (E)-2-[(2-bromopyridin-3-yl)methylidene]-6-methoxy-3,4-dihydronaphthalen-1(2H)-one and 3-[(E)-(6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalen-2-ylidene)methyl]pyridin-2(1H)-one |
title_short | Crystal structure of (E)-2-[(2-bromopyridin-3-yl)methylidene]-6-methoxy-3,4-dihydronaphthalen-1(2H)-one and 3-[(E)-(6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalen-2-ylidene)methyl]pyridin-2(1H)-one |
title_sort | crystal structure of (e)-2-[(2-bromopyridin-3-yl)methylidene]-6-methoxy-3,4-dihydronaphthalen-1(2h)-one and 3-[(e)-(6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalen-2-ylidene)methyl]pyridin-2(1h)-one |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4992914/ https://www.ncbi.nlm.nih.gov/pubmed/27555939 http://dx.doi.org/10.1107/S2056989016009300 |
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