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

Carlos Bustos, Luis Alvarez-Thon, Ricardo Baggio

Resultado de la investigación: Article

1 Cita (Scopus)

Resumen

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.

Idioma originalEnglish
Páginas (desde-hasta)1106-1113
Número de páginas8
PublicaciónActa Crystallographica Section C: Structural Chemistry
Volumen71
DOI
EstadoPublished - 1 ene 2015
Publicado de forma externa

Huella dactilar

hydrazine
Hydrazine
tetrahydrofuran
Propane
Pyrazoles
Crystals
Molecules
Electrons
hydrazines
propane
routes
interactions
inversions
preparation
crystals
molecules
electrons
4-nitrophenyl

ASJC Scopus subject areas

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

Citar esto

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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.",
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Structural aspects of two α-dihydrazones displaying a complete survey of intermolecular interactions. / Bustos, Carlos; Alvarez-Thon, Luis; Baggio, Ricardo.

En: Acta Crystallographica Section C: Structural Chemistry, Vol. 71, 01.01.2015, p. 1106-1113.

Resultado de la investigación: Article

TY - JOUR

T1 - Structural aspects of two α-dihydrazones displaying a complete survey of intermolecular interactions

AU - Bustos, Carlos

AU - Alvarez-Thon, Luis

AU - Baggio, Ricardo

PY - 2015/1/1

Y1 - 2015/1/1

N2 - 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.

AB - 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.

KW - crystal structure

KW - electron donor-acceptor (EDA) interactions

KW - ester

KW - hydrazines

KW - short O⋯O contacts

KW - substituted pyrazoles

KW - α-dihydrazones

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U2 - 10.1107/S2053229615021944

DO - 10.1107/S2053229615021944

M3 - Article

AN - SCOPUS:84948745199

VL - 71

SP - 1106

EP - 1113

JO - Acta crystallographica. Section C, Structural chemistry

JF - Acta crystallographica. Section C, Structural chemistry

SN - 2053-2296

ER -