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- Title
Structural aspects of two α-dihydrazones displaying a complete survey of intermolecular interactions.
- Authors
Bustos, Carlos; Alvarez-Thon, Luis; Baggio, Ricardo
- Abstract
The compounds (2′ E,2′ E)-2,2′-(propane-1,2-diylidene)bis[1-(2-nitrophenyl)hydrazine], C15H14N6O4, (I), and (2 Z,3 Z)-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.
- Subjects
HYDRAZONES; INTERMOLECULAR interactions; PYRAZOLES
- Publication
Acta Crystallographica Section C: Structural Chemistry, 2015, Vol 71, Issue 12, p1106
- ISSN
2053-2296
- Publication type
Article
- DOI
10.1107/S2053229615021944