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Crystal structures of three N-(3-acetyl­phen­yl)quinoline-2-carboxamides

In the title compounds, N-(5-acetyl-2-methyl­phen­yl)quinoline-2-carboxamide [C(19)H(16)N(2)O(2), (I)], N-(5-acetyl-2-bromo­phen­yl)quinoline-2-carboxamide [C(18)H(13)BrN(2)O(2), (II)] and N-(5-acetyl-2-ethynylphen­yl)quinoline-2-carboxamide [C(20)H(14)N(2)O(2), (III)], the quinoline ring system is...

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Autores principales: Peña-Solórzano, Diana, König, Burkhard, Sierra, Cesar A., Ochoa-Puentes, Cristian
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5458296/
https://www.ncbi.nlm.nih.gov/pubmed/28638631
http://dx.doi.org/10.1107/S2056989017006272
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author Peña-Solórzano, Diana
König, Burkhard
Sierra, Cesar A.
Ochoa-Puentes, Cristian
author_facet Peña-Solórzano, Diana
König, Burkhard
Sierra, Cesar A.
Ochoa-Puentes, Cristian
author_sort Peña-Solórzano, Diana
collection PubMed
description In the title compounds, N-(5-acetyl-2-methyl­phen­yl)quinoline-2-carboxamide [C(19)H(16)N(2)O(2), (I)], N-(5-acetyl-2-bromo­phen­yl)quinoline-2-carboxamide [C(18)H(13)BrN(2)O(2), (II)] and N-(5-acetyl-2-ethynylphen­yl)quinoline-2-carboxamide [C(20)H(14)N(2)O(2), (III)], the quinoline ring system is essentially planar and forms a dihedral angles of 3.68 (5) (I), 5.59 (7) (II) and 1.87 (6)° (III) with the acetyl-substituted ring. The mol­ecular structures of (I) and (III) each feature an intra­molecular N—H⋯N hydrogen bond, forming an S(5) ring, while in (II) an intra­molecular bifurcated N—H⋯(N,Br) hydrogen bond forms two S(5) rings. In the crystals, weak C—H⋯O hydrogen bonds link mol­ecules of (I) into C(7) chains long [010], mol­ecules of (II) into chains of R (2) (2)(8) rings along [110] and mol­ecules of (III) into C(8) chains along [010]. In (I), there are no significant π–π stacking inter­actions under 4 Å, but in both (II) and (III), π–π inter­actions link the weak hydrogen-bonded chains into layers parallel to (001) [centroid–centroid disttances of 3.748 (1) Å in (II) and 3.577 (1), 3.784 (1) and 3.780 (1) Å in (III)].
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spelling pubmed-54582962017-06-21 Crystal structures of three N-(3-acetyl­phen­yl)quinoline-2-carboxamides Peña-Solórzano, Diana König, Burkhard Sierra, Cesar A. Ochoa-Puentes, Cristian Acta Crystallogr E Crystallogr Commun Research Communications In the title compounds, N-(5-acetyl-2-methyl­phen­yl)quinoline-2-carboxamide [C(19)H(16)N(2)O(2), (I)], N-(5-acetyl-2-bromo­phen­yl)quinoline-2-carboxamide [C(18)H(13)BrN(2)O(2), (II)] and N-(5-acetyl-2-ethynylphen­yl)quinoline-2-carboxamide [C(20)H(14)N(2)O(2), (III)], the quinoline ring system is essentially planar and forms a dihedral angles of 3.68 (5) (I), 5.59 (7) (II) and 1.87 (6)° (III) with the acetyl-substituted ring. The mol­ecular structures of (I) and (III) each feature an intra­molecular N—H⋯N hydrogen bond, forming an S(5) ring, while in (II) an intra­molecular bifurcated N—H⋯(N,Br) hydrogen bond forms two S(5) rings. In the crystals, weak C—H⋯O hydrogen bonds link mol­ecules of (I) into C(7) chains long [010], mol­ecules of (II) into chains of R (2) (2)(8) rings along [110] and mol­ecules of (III) into C(8) chains along [010]. In (I), there are no significant π–π stacking inter­actions under 4 Å, but in both (II) and (III), π–π inter­actions link the weak hydrogen-bonded chains into layers parallel to (001) [centroid–centroid disttances of 3.748 (1) Å in (II) and 3.577 (1), 3.784 (1) and 3.780 (1) Å in (III)]. International Union of Crystallography 2017-05-05 /pmc/articles/PMC5458296/ /pubmed/28638631 http://dx.doi.org/10.1107/S2056989017006272 Text en © Peña-Solórzano et al. 2017 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
Peña-Solórzano, Diana
König, Burkhard
Sierra, Cesar A.
Ochoa-Puentes, Cristian
Crystal structures of three N-(3-acetyl­phen­yl)quinoline-2-carboxamides
title Crystal structures of three N-(3-acetyl­phen­yl)quinoline-2-carboxamides
title_full Crystal structures of three N-(3-acetyl­phen­yl)quinoline-2-carboxamides
title_fullStr Crystal structures of three N-(3-acetyl­phen­yl)quinoline-2-carboxamides
title_full_unstemmed Crystal structures of three N-(3-acetyl­phen­yl)quinoline-2-carboxamides
title_short Crystal structures of three N-(3-acetyl­phen­yl)quinoline-2-carboxamides
title_sort crystal structures of three n-(3-acetyl­phen­yl)quinoline-2-carboxamides
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5458296/
https://www.ncbi.nlm.nih.gov/pubmed/28638631
http://dx.doi.org/10.1107/S2056989017006272
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