Structural aspects of two α-dihydrazones displaying a complete survey of intermolecular interactions

Carlos Bustos, Luis Alvarez-Thon, Ricardo Baggio

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

The compounds (2'E,2'E)-2,2'-(propane-1,2-diylidene)bis[1-(2-nitrophenyl)hydrazine], C15H14N6O4, (I), and (2Z,3Z)-ethyl 3-[2-(2-nitrophenyl)hydrazinylidene]-2-[2-(4-nitrophenyl)hydrazinylidene]butanoate tetrahydrofuran hemisolvate, C18H18N6O6·0.5C4H8O, (II), are puzzling outliers deviating from a general synthetic route aimed at the preparation of substituted pyrazoles. Possible reasons for this outcome, which is exceptional in an otherwise firmly established synthetic procedure, are analyzed. Compound (I) is unsolvated, while compound (II) crystallizes with a tetrahydrofuran solvent molecule lying on an inversion centre. The ethoxycarbonyl chain of (II), in turn, appears disordered into two equally populated (50%) moieties. In both structures, a plethora of different commonly occurring weak intermolecular interactions [viz. π(phenyl)⋯π(phenyl), π(C=N)⋯π(C=N), π(phenyl)⋯π(C=N), N - H⋯O and C - H⋯O] appear responsible for the crystal stability. Much less common are the short O(nitro)⋯O(nitro) contacts which are observed in the structure of (I), an example of unusual 'electron donor-acceptor' (EDA) interactions.

Original languageEnglish
Pages (from-to)1106-1113
Number of pages8
JournalActa Crystallographica Section C: Structural Chemistry
Volume71
DOIs
Publication statusPublished - 1 Jan 2015
Externally publishedYes

Keywords

  • crystal structure
  • electron donor-acceptor (EDA) interactions
  • ester
  • hydrazines
  • short O⋯O contacts
  • substituted pyrazoles
  • α-dihydrazones

ASJC Scopus subject areas

  • Condensed Matter Physics
  • Physical and Theoretical Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

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