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Crystal structures of (E)-2-((2-((pyridin-2-yl)hydrazonyl)methyl)phenolic compounds: different sets of classical hydrogen bonds, X–H···Y (X, Y = O, N)

  • Nathasha R. de L. Correira , Thais C.M. Noguiera , Alessandra C. Pinheiro , Marcus V.N. de Souza , James L. Wardell EMAIL logo and Solange M.S.V. Wardell
Published/Copyright: January 30, 2016
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Zeitschrift für Kristallographie - Crystalline Materials
From the journal Zeitschrift für Kristallographie - Crystalline Materials Volume 231 Issue 5

Abstract

Structures are reported of (E)-((2-((pyridin-2-yl)hydrazonyl)methyl)arene compounds, 2-aryl-CH=N–CH)-pyridine, 8, namely (aryl=2,4-(HO)2C6H3, 8a; 2,5-(HO)2C6H3, 8b, 2–HOC6H4, 8c, as the hemihydrate, [(8c)2·(H2O)], 2–HO–5–O2NC6H3, 8d; and 2,6-(MeO)2C6H3, 8e. Intramolecular O1–H1··· N2(hydrazonyl) hydrogen bonds are consistantly found in each of the hydroxy compounds, 8a–8d. However, a diverse array of classical intermolecular hydrogen bonds, X–H···Y (X or Y = O or N) are found in 8a–8e. Classical intermolecular hydrogen bonds in 8a are chain forming N3–HN3···O1 and O2–H2···N1(pyridinyl) intermolecular hydrogen bonds, while in the isomer, 8b, dimer forming N3–HN3···N1(pyridinyl) and chain forming O2–H2···O1(pyridinyl) hydrogen bonds are present. The hydrate molecule in [(8c)2·(H2O)] is involved in Ow–Hw···N1 intermolecular hydrogen bonding: also present in [(8c)2·(H2O)] are chain forming N3–HN3···O2 bonds. The only intermolecular classical hydrogen bonds present in 8d and 8e, are the dimer forming N3–HN3···N1(pyridinyl) bonds. Thus only compounds, 8b, 8d and 8e, exhibit dimer forming N3–HN3···N1(pyridinyl) hydrogen bonds, previously reported fora range of (aryl-CH=N–CH)-pyridine derivatives. The occurence of N3–HN3···N1(pyridinyl) hydrogen bonds in many (aryl-CH=N–CH)-pyridine derivatives demonstrates the importance of such hydrogen bonds. However, as found in 8a and [(8c)2·(H2O)], suitable sited donor substituents or the presence of solvate molecules can result in other classical hydrogen bonds being preferred.

Keywords: classical hydrogen bonds; pyridinylhydrazones; supramolecular arrays; X-ray crystallography
Corresponding author: James L. Wardell, FioCruz-Fundação Oswaldo Cruz, Instituto de Tecnologia em Fármacos-Far-Manguinhos, Rua Sizenando Nabuco, 100, Manguinhos, 21041-250 Rio de Janeiro, RJ, Brazil; and CHEMSOL, 1 Harcourt Road, Aberdeen AB15 5NY, Scotland, UK, E-mail:

Acknowledgments

The use of the NCS crystallographic service at Southampton and the valuable assistance of the staff there are gratefully acknowledged. JLW thanks FAPERJ and CNPq, Brazil for support.

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Supplemental Material

The online version of this article (DOI: 10.1515/zkri-2015-1910) offers supplementary material, available to authorized users.

Received: 2015-10-31
Accepted: 2016-1-9
Published Online: 2016-1-30
Published in Print: 2016-5-1

©2016 by De Gruyter

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https://doi.org/10.1515/zkri-2015-1910
Keywords for this article
classical hydrogen bonds; pyridinylhydrazones; supramolecular arrays; X-ray crystallography

Articles in the same Issue

  1. Frontmatter
  2. Graphical Synopsis
  3. Inorganic Crystal Structures
  4. β-K2Se2 and K2Se4: missing links in the binary system K-Se
  5. Debye function analysis of nanocrystalline gallium oxide γ-Ga2O3
  6. Crystal structure of the alluaudite Ag2Mn3(VO4)3
  7. Organic and Metalorganic Crystal Structures
  8. Crystal structures of (E)-2-((2-((pyridin-2-yl)hydrazonyl)methyl)phenolic compounds: different sets of classical hydrogen bonds, X–H···Y (X, Y = O, N)
  9. Syntheses, crystal structures and thermal properties of two novel isostructural Co(III) complexes with salophen ligand
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  11. Crystallographic Computing
  12. Discontinuous modulation functions and their application for analysis of modulated structures with the computing system JANA2006
  13. Corrigendum
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