On substituted pyrazole derivatives. II. (E)-1-(4-{[1-(4-Fluorophenyl)-3,5-dimethyl-1H-pyrazol-4-yl]diazenyl}phenyl)ethanone and (E)-1-(4-chlorophenyl)-3,5-dimethyl-4-[2-(2-nitrophenyl)diazenyl]-1H-pyrazole

Carlos Bustos; Luis Alvarez-Thon; Tania Oportus; Angela Mesías-Salazar; Ricardo Baggio

doi:10.1107/S2053229614024619

On substituted pyrazole derivatives. II. (E)-1-(4-{[1-(4-Fluorophenyl)-3,5-dimethyl-1H-pyrazol-4-yl]diazenyl}phenyl)ethanone and (E)-1-(4-chlorophenyl)-3,5-dimethyl-4-[2-(2-nitrophenyl)diazenyl]-1H-pyrazole

Carlos Bustos
, Luis Alvarez-Thon
, Tania Oportus
, Angela Mesías-Salazar
, Ricardo Baggio

Research output: Contribution to journal › Article › peer-review

1 Scopus citations

Abstract

The molecular structures of (E)-1-(4-{[1-(4-fluorophenyl)-3,5-dimethyl-1H-pyrazol-4-yl]diazenyl}phenyl)ethanone, C19H17FN4O, (III), and (E)-1-(4-chlorophenyl)-3,5-dimethyl-4-[2-(2-nitrophenyl)diazenyl]-1H-pyrazole, C17H14ClN5O2, (IV), prepared by reaction of the corresponding β-diketohydrazones with substituted arylhydrazines in acid media, are nonplanar, with the planes of the lateral phenyl rings forming dihedral angles with that of the central pyrazole ring varying from 2.71(7) to 45.22(7)°. The crystal structures are supported by C - H⋯O, C - H⋯π and π-π weak intermolecular interactions together with some unusual trifurcated C - Cl⋯Cl - C contacts, which are discussed in detail.

Original language	English
Pages (from-to)	53-58
Number of pages	6
Journal	Acta Crystallographica Section C: Structural Chemistry
Volume	71
DOIs	https://doi.org/10.1107/S2053229614024619
State	Published - 1 Jan 2015
Externally published	Yes

Keywords

crystal structure
pharmaceutical compounds
substituted pyrazoles
trifurcated C - Cl⋯Cl - C interactions
weakly bound supramolecular structures

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10.1107/S2053229614024619

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Bustos, C., Alvarez-Thon, L., Oportus, T., Mesías-Salazar, A., & Baggio, R. (2015). On substituted pyrazole derivatives. II. (E)-1-(4-{[1-(4-Fluorophenyl)-3,5-dimethyl-1H-pyrazol-4-yl]diazenyl}phenyl)ethanone and (E)-1-(4-chlorophenyl)-3,5-dimethyl-4-[2-(2-nitrophenyl)diazenyl]-1H-pyrazole. Acta Crystallographica Section C: Structural Chemistry, 71, 53-58. https://doi.org/10.1107/S2053229614024619

@article{6a71617aab7b434193fb2321cf4cd076,

title = "On substituted pyrazole derivatives. II. (E)-1-(4-\{[1-(4-Fluorophenyl)-3,5-dimethyl-1H-pyrazol-4-yl]diazenyl\}phenyl)ethanone and (E)-1-(4-chlorophenyl)-3,5-dimethyl-4-[2-(2-nitrophenyl)diazenyl]-1H-pyrazole",

abstract = "The molecular structures of (E)-1-(4-\{[1-(4-fluorophenyl)-3,5-dimethyl-1H-pyrazol-4-yl]diazenyl\}phenyl)ethanone, C19H17FN4O, (III), and (E)-1-(4-chlorophenyl)-3,5-dimethyl-4-[2-(2-nitrophenyl)diazenyl]-1H-pyrazole, C17H14ClN5O2, (IV), prepared by reaction of the corresponding β-diketohydrazones with substituted arylhydrazines in acid media, are nonplanar, with the planes of the lateral phenyl rings forming dihedral angles with that of the central pyrazole ring varying from 2.71(7) to 45.22(7)°. The crystal structures are supported by C - H⋯O, C - H⋯π and π-π weak intermolecular interactions together with some unusual trifurcated C - Cl⋯Cl - C contacts, which are discussed in detail.",

keywords = "crystal structure, pharmaceutical compounds, substituted pyrazoles, trifurcated C - Cl⋯Cl - C interactions, weakly bound supramolecular structures",

author = "Carlos Bustos and Luis Alvarez-Thon and Tania Oportus and Angela Mes{\'i}as-Salazar and Ricardo Baggio",

note = "Publisher Copyright: {\textcopyright} 2015 International Union of Crystallography.",

year = "2015",

month = jan,

day = "1",

doi = "10.1107/S2053229614024619",

language = "English",

volume = "71",

pages = "53--58",

journal = "Acta Crystallographica Section C: Structural Chemistry",

issn = "2053-2296",

}

Bustos, C, Alvarez-Thon, L, Oportus, T, Mesías-Salazar, A & Baggio, R 2015, 'On substituted pyrazole derivatives. II. (E)-1-(4-{[1-(4-Fluorophenyl)-3,5-dimethyl-1H-pyrazol-4-yl]diazenyl}phenyl)ethanone and (E)-1-(4-chlorophenyl)-3,5-dimethyl-4-[2-(2-nitrophenyl)diazenyl]-1H-pyrazole', Acta Crystallographica Section C: Structural Chemistry, vol. 71, pp. 53-58. https://doi.org/10.1107/S2053229614024619

On substituted pyrazole derivatives. II. (E)-1-(4-{[1-(4-Fluorophenyl)-3,5-dimethyl-1H-pyrazol-4-yl]diazenyl}phenyl)ethanone and (E)-1-(4-chlorophenyl)-3,5-dimethyl-4-[2-(2-nitrophenyl)diazenyl]-1H-pyrazole. / Bustos, Carlos; Alvarez-Thon, Luis; Oportus, Tania et al.
In: Acta Crystallographica Section C: Structural Chemistry, Vol. 71, 01.01.2015, p. 53-58.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - On substituted pyrazole derivatives. II. (E)-1-(4-{[1-(4-Fluorophenyl)-3,5-dimethyl-1H-pyrazol-4-yl]diazenyl}phenyl)ethanone and (E)-1-(4-chlorophenyl)-3,5-dimethyl-4-[2-(2-nitrophenyl)diazenyl]-1H-pyrazole

AU - Bustos, Carlos

AU - Alvarez-Thon, Luis

AU - Oportus, Tania

AU - Mesías-Salazar, Angela

AU - Baggio, Ricardo

PY - 2015/1/1

Y1 - 2015/1/1

N2 - The molecular structures of (E)-1-(4-{[1-(4-fluorophenyl)-3,5-dimethyl-1H-pyrazol-4-yl]diazenyl}phenyl)ethanone, C19H17FN4O, (III), and (E)-1-(4-chlorophenyl)-3,5-dimethyl-4-[2-(2-nitrophenyl)diazenyl]-1H-pyrazole, C17H14ClN5O2, (IV), prepared by reaction of the corresponding β-diketohydrazones with substituted arylhydrazines in acid media, are nonplanar, with the planes of the lateral phenyl rings forming dihedral angles with that of the central pyrazole ring varying from 2.71(7) to 45.22(7)°. The crystal structures are supported by C - H⋯O, C - H⋯π and π-π weak intermolecular interactions together with some unusual trifurcated C - Cl⋯Cl - C contacts, which are discussed in detail.

AB - The molecular structures of (E)-1-(4-{[1-(4-fluorophenyl)-3,5-dimethyl-1H-pyrazol-4-yl]diazenyl}phenyl)ethanone, C19H17FN4O, (III), and (E)-1-(4-chlorophenyl)-3,5-dimethyl-4-[2-(2-nitrophenyl)diazenyl]-1H-pyrazole, C17H14ClN5O2, (IV), prepared by reaction of the corresponding β-diketohydrazones with substituted arylhydrazines in acid media, are nonplanar, with the planes of the lateral phenyl rings forming dihedral angles with that of the central pyrazole ring varying from 2.71(7) to 45.22(7)°. The crystal structures are supported by C - H⋯O, C - H⋯π and π-π weak intermolecular interactions together with some unusual trifurcated C - Cl⋯Cl - C contacts, which are discussed in detail.

KW - crystal structure

KW - pharmaceutical compounds

KW - substituted pyrazoles

KW - trifurcated C - Cl⋯Cl - C interactions

KW - weakly bound supramolecular structures

UR - https://www.scopus.com/pages/publications/84937420908

U2 - 10.1107/S2053229614024619

DO - 10.1107/S2053229614024619

M3 - Article

AN - SCOPUS:84937420908

SN - 2053-2296

VL - 71

SP - 53

EP - 58

JO - Acta Crystallographica Section C: Structural Chemistry

JF - Acta Crystallographica Section C: Structural Chemistry

ER -

Bustos C, Alvarez-Thon L, Oportus T, Mesías-Salazar A, Baggio R. On substituted pyrazole derivatives. II. (E)-1-(4-{[1-(4-Fluorophenyl)-3,5-dimethyl-1H-pyrazol-4-yl]diazenyl}phenyl)ethanone and (E)-1-(4-chlorophenyl)-3,5-dimethyl-4-[2-(2-nitrophenyl)diazenyl]-1H-pyrazole. Acta Crystallographica Section C: Structural Chemistry. 2015 Jan 1;71:53-58. doi: 10.1107/S2053229614024619

On substituted pyrazole derivatives. II. (E)-1-(4-{[1-(4-Fluorophenyl)-3,5-dimethyl-1H-pyrazol-4-yl]diazenyl}phenyl)ethanone and (E)-1-(4-chlorophenyl)-3,5-dimethyl-4-[2-(2-nitrophenyl)diazenyl]-1H-pyrazole

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