Crystal structures and Hirshfeld surface analysis of four 1,4-bis(methoxyphenyl)-2,3-diazabuta-1,3-dienes: comparisons of the intermolecular interactions in related compounds
Author:
Gomes Ligia R.12, Low John N.3, Correira Nathasha R. de L.4, Noguiera Thais C.M.4, Pinheiro Alessandra C.4, de Souza Marcus V.N.4, Wardell James L.34, Wardell Solange M.S.V.5
Affiliation:
1. FP-ENAS-Faculdade de Ciências de Saúde, Escola Superior de Saúde da UFP, Universidade Fernando Pessoa , Rua Carlos da Maia, 296 , Porto P-4200-150 , Portugal 2. REQUIMTE, Departamento de Química e Bioquímica , Faculdade de Ciências da Universidade do Porto , Rua do Campo Alegre, 687 , Porto P-4169-007 , Portugal 3. Department of Chemistry , University of Aberdeen , Old Aberdeen, AB24 3UE, Scotland , UK 4. FioCruz-Fundação Oswaldo Cruz, Instituto de Tecnologia em Fármacos-Far-Manguinhos , Rua Sizenando Nabuco, 100, Manguinhos , Rio de Janeiro 21041-250, RJ , Brazil 5. CHEMSOL , 1 Harcourt Road , Aberdeen AB15 5NY , Scotland , UK
Abstract
Abstract
The crystal structures of four azines, namely 1-3-bis(4-methoxyphenyl)-2,3-diaza-1,4-butadiene, 1, 1,3-bis(2,3-dimethoxyphenyl)-2,3-diaza-1,4-butadiene, 2, 1,3-bis(2-hydroxy-3-methoxyphenyl)-2,3-diaza-1,4-butadiene, 3, and 1,3-bis(2-hydroxy-4-methoxyphenyl)-2,3-diaza-1,4-butadiene, 4, are reported. Molecules of 3 and 4, and both independent molecules of 2, Mol A and Mol B, possess inversion centers. The central C=N–N=C units in each molecule is planar with an (E,E) conformation. The intermolecular interactions found in the four compounds are C–H···O, C–H–N, C–H---π and π---π interactions. However, there is no consistent set of intermolecular interactions for the four compounds. Compound, 1, has a two-dimensional undulating sheet structure, generated from C–H···O and C–H···N intermolecular hydrogen bonds. The only recognized intermolecular interaction in 2 is a C–H···O hydrogen bond, which results in a zig-zag chain of alternating molecules, Mol A and Mol B. While 3 forms a puckered sheet of molecules, solely via C–H···π interactions, its isomeric compound, 4, has a more elaborate three-dimensional structure generated from a combination of C–H···O hydrogen bonds, C–H···π and π···π interactions.
The findings in this study, based on both PLATON and Hirshfeld approaches, for the four representative compounds match well the reported structural findings in the literature of related compounds, which are based solely on geometric parameters.
Publisher
Walter de Gruyter GmbH
Subject
Inorganic Chemistry,Condensed Matter Physics,General Materials Science
Reference51 articles.
1. J. Safari, S. Gandomi-Ravandi, Structure, synthesis and application of azines: a historical perspective. RSC Adv. 2014, 4, 46224–46249.10.1039/C4RA04870A 2. V. Arun, K. R. Sankaran, Characterization and Computational analysis of unsymmetrical azines, Can. Chem. Trans. 2015, 3, 319–326. 3. Y. Wan, Q. Li, Light-driven chiral molecular switches or motors in liquid crystals, Adv. Mater. 2012, 24, 1926–1945.10.1002/adma.201200241 4. J.-L. Yang, J. Rui, X. Xu, Y.-Q. Yang, J. Su, H.-J. Xu, Y.-Y. Wang, N. Sun, S. Wang, Fluorescence staining of salicylaldehyde azine, and applications in the determination of potassium tert-butoxide. RSC Adv. 2016, 6, 30636.10.1039/C6RA01035K 5. E. Serdiuk, A. D. Roshal, Exploring double proton transfer: a review on photochemical features of compounds with two proton-transfer sites. Dyes Pigm.2017, 138, 223–244.10.1016/j.dyepig.2016.11.028
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