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Crystal structures and Hirshfeld surfaces of differently substituted (E)-N′-benzyl­idene-N-methyl-2-(thio­phen-2-yl)acetohydrazides

The syntheses and crystal structures of (E)-N′-(3-cyano­benzyl­idene)-N-methyl-2-(thio­phen-2-yl)acetohydrazide, C(15)H(13)N(3)OS, (I), and (E)-N′-(4-meth­oxy­benzyl­idene)-N-methyl-2-(thio­phen-2-yl)acetohydrazide, C(15)H(16)N(2)O(2)S, (II), with different substituents in the meta and para position...

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Autores principales: Cardoso, Laura N. F., Noguiera, Thais C. M., Kaiser, Carlos R., Wardell, James L., de Souza, Marcus V. N., Harrison, William T. A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5683480/
https://www.ncbi.nlm.nih.gov/pubmed/29152340
http://dx.doi.org/10.1107/S2056989017014384
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author Cardoso, Laura N. F.
Noguiera, Thais C. M.
Kaiser, Carlos R.
Wardell, James L.
de Souza, Marcus V. N.
Harrison, William T. A.
author_facet Cardoso, Laura N. F.
Noguiera, Thais C. M.
Kaiser, Carlos R.
Wardell, James L.
de Souza, Marcus V. N.
Harrison, William T. A.
author_sort Cardoso, Laura N. F.
collection PubMed
description The syntheses and crystal structures of (E)-N′-(3-cyano­benzyl­idene)-N-methyl-2-(thio­phen-2-yl)acetohydrazide, C(15)H(13)N(3)OS, (I), and (E)-N′-(4-meth­oxy­benzyl­idene)-N-methyl-2-(thio­phen-2-yl)acetohydrazide, C(15)H(16)N(2)O(2)S, (II), with different substituents in the meta and para position of the benzene ring are described. Compounds (I) and (II) both crystallize with two mol­ecules in the asymmetric unit, with generally similar conformations [r.m.s. overlay fits for (I) and (II) of 0.334 and 0.280 Å, respectively] that approximate to L-shapes. The thio­phene rings in (I) are well ordered, whereas those in (II) exhibit ‘flip’ rotational disorder [occupancies 0.662 (2) and 0.338 (2) for mol­ecule 1, and 0.549 (3) and 0.451 (3) for mol­ecule 2]. The packing for (I) features short C—H⋯O inter­actions arising from the C—H grouping adjacent to the cyanide group and C—H⋯N(c) (c = cyanide) links arising from the methine groups to generate [110] double chains. Weak C—H⋯π inter­actions inter­link the chains into a three-dimensional network. The packing for (II) features numerous C—H⋯O and C—H⋯π inter­actions arising from different donor groups to generate a three-dimensional network. Hirshfeld fingerprint plots indicate significant differences in the percentage contact surfaces for (I) and (II).
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spelling pubmed-56834802017-11-17 Crystal structures and Hirshfeld surfaces of differently substituted (E)-N′-benzyl­idene-N-methyl-2-(thio­phen-2-yl)acetohydrazides Cardoso, Laura N. F. Noguiera, Thais C. M. Kaiser, Carlos R. Wardell, James L. de Souza, Marcus V. N. Harrison, William T. A. Acta Crystallogr E Crystallogr Commun Research Communications The syntheses and crystal structures of (E)-N′-(3-cyano­benzyl­idene)-N-methyl-2-(thio­phen-2-yl)acetohydrazide, C(15)H(13)N(3)OS, (I), and (E)-N′-(4-meth­oxy­benzyl­idene)-N-methyl-2-(thio­phen-2-yl)acetohydrazide, C(15)H(16)N(2)O(2)S, (II), with different substituents in the meta and para position of the benzene ring are described. Compounds (I) and (II) both crystallize with two mol­ecules in the asymmetric unit, with generally similar conformations [r.m.s. overlay fits for (I) and (II) of 0.334 and 0.280 Å, respectively] that approximate to L-shapes. The thio­phene rings in (I) are well ordered, whereas those in (II) exhibit ‘flip’ rotational disorder [occupancies 0.662 (2) and 0.338 (2) for mol­ecule 1, and 0.549 (3) and 0.451 (3) for mol­ecule 2]. The packing for (I) features short C—H⋯O inter­actions arising from the C—H grouping adjacent to the cyanide group and C—H⋯N(c) (c = cyanide) links arising from the methine groups to generate [110] double chains. Weak C—H⋯π inter­actions inter­link the chains into a three-dimensional network. The packing for (II) features numerous C—H⋯O and C—H⋯π inter­actions arising from different donor groups to generate a three-dimensional network. Hirshfeld fingerprint plots indicate significant differences in the percentage contact surfaces for (I) and (II). International Union of Crystallography 2017-10-13 /pmc/articles/PMC5683480/ /pubmed/29152340 http://dx.doi.org/10.1107/S2056989017014384 Text en © Cardoso 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
Cardoso, Laura N. F.
Noguiera, Thais C. M.
Kaiser, Carlos R.
Wardell, James L.
de Souza, Marcus V. N.
Harrison, William T. A.
Crystal structures and Hirshfeld surfaces of differently substituted (E)-N′-benzyl­idene-N-methyl-2-(thio­phen-2-yl)acetohydrazides
title Crystal structures and Hirshfeld surfaces of differently substituted (E)-N′-benzyl­idene-N-methyl-2-(thio­phen-2-yl)acetohydrazides
title_full Crystal structures and Hirshfeld surfaces of differently substituted (E)-N′-benzyl­idene-N-methyl-2-(thio­phen-2-yl)acetohydrazides
title_fullStr Crystal structures and Hirshfeld surfaces of differently substituted (E)-N′-benzyl­idene-N-methyl-2-(thio­phen-2-yl)acetohydrazides
title_full_unstemmed Crystal structures and Hirshfeld surfaces of differently substituted (E)-N′-benzyl­idene-N-methyl-2-(thio­phen-2-yl)acetohydrazides
title_short Crystal structures and Hirshfeld surfaces of differently substituted (E)-N′-benzyl­idene-N-methyl-2-(thio­phen-2-yl)acetohydrazides
title_sort crystal structures and hirshfeld surfaces of differently substituted (e)-n′-benzyl­idene-n-methyl-2-(thio­phen-2-yl)acetohydrazides
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5683480/
https://www.ncbi.nlm.nih.gov/pubmed/29152340
http://dx.doi.org/10.1107/S2056989017014384
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