Crystal structure of (Z)-4-[1-(4-acetylanilino)ethyl-idene]-3-methyl-1-phenyl-1 H-pyrazol-5(4H)-one

Refaat M. Mahfouz; Zeynep Demircioglu; Mohamed S. Abbady; Orhan Büyükgüngör; W. T A Harrison

doi:10.1107/S2056989014026899

Crystal structure of (Z)-4-[1-(4-acetylanilino)ethyl-idene]-3-methyl-1-phenyl-1 H-pyrazol-5(4H)-one

Refaat M. Mahfouz, Zeynep Demircioglu^*, Mohamed S. Abbady, Orhan Büyükgüngör, W. T A Harrison (Editor)

^*Corresponding author for this work

Chemistry

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

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Abstract

In the solid state, the title compound, C₂₀H₁₉N₃O₂, adopts the keto-amine tautomeric form, with the H atom attached to the N atom, which participates in an intramolecular N - H⋯O hydrogen bond with an S(6) ring motif. The dihedral angles between the pyrazole ring and the phenyl and benzene rings are 3.69 (10) and 46.47 (9)°, respectively. In the crystal, molecules are linked by weak C - H⋯O hydrogen bonds, generating C(16) chains propagating in [301]. Weak aromatic π-π stacking interactions [centroid-centroid distances = 3.6123 (10) and 3.6665 (10) Å] link the chains into a three-dimensional network.

Original language	English
Pages (from-to)	94-96
Number of pages	3
Journal	Acta Crystallographica Section E: Structure Reports Online
Volume	71
Issue number	1
DOIs	https://doi.org/10.1107/S2056989014026899
Publication status	Published - 1 Jan 2015

Bibliographical note

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund).

Keywords

Crystal structure
Hydrogen bonding
Keto-amine tautomeric form
Pyrazolone derivatives
Schiff bases
π-πstacking interactions

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10.1107/S2056989014026899Licence: CC BY

Crystal structure of (Z)-4-[1-(4-acetylanilino)ethylidene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one
© 2015 Mahfouzet al. Licence: Creative Commons Attribution (CC-BY) https://creativecommons.org/licenses/by/4.0/
Final published version, 400 KBLicence: CC BY

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title = "Crystal structure of (Z)-4-[1-(4-acetylanilino)ethyl-idene]-3-methyl-1-phenyl-1 H-pyrazol-5(4H)-one",

abstract = "In the solid state, the title compound, C20H19N3O2, adopts the keto-amine tautomeric form, with the H atom attached to the N atom, which participates in an intramolecular N - H⋯O hydrogen bond with an S(6) ring motif. The dihedral angles between the pyrazole ring and the phenyl and benzene rings are 3.69 (10) and 46.47 (9)°, respectively. In the crystal, molecules are linked by weak C - H⋯O hydrogen bonds, generating C(16) chains propagating in [301]. Weak aromatic π-π stacking interactions [centroid-centroid distances = 3.6123 (10) and 3.6665 (10) {\AA}] link the chains into a three-dimensional network.",

keywords = "Crystal structure, Hydrogen bonding, Keto-amine tautomeric form, Pyrazolone derivatives, Schiff bases, π-πstacking interactions",

author = "Mahfouz, {Refaat M.} and Zeynep Demircioglu and Abbady, {Mohamed S.} and Orhan B{\"u}y{\"u}kg{\"u}ng{\"o}r and Harrison, {W. T A}",

note = "The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund).",

year = "2015",

month = jan,

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doi = "10.1107/S2056989014026899",

language = "English",

volume = "71",

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journal = "Acta Crystallographica Section E: Structure Reports Online",

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AU - Mahfouz, Refaat M.

AU - Demircioglu, Zeynep

AU - Abbady, Mohamed S.

AU - Büyükgüngör, Orhan

A2 - Harrison, W. T A

N1 - The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund).

PY - 2015/1/1

Y1 - 2015/1/1

N2 - In the solid state, the title compound, C20H19N3O2, adopts the keto-amine tautomeric form, with the H atom attached to the N atom, which participates in an intramolecular N - H⋯O hydrogen bond with an S(6) ring motif. The dihedral angles between the pyrazole ring and the phenyl and benzene rings are 3.69 (10) and 46.47 (9)°, respectively. In the crystal, molecules are linked by weak C - H⋯O hydrogen bonds, generating C(16) chains propagating in [301]. Weak aromatic π-π stacking interactions [centroid-centroid distances = 3.6123 (10) and 3.6665 (10) Å] link the chains into a three-dimensional network.

AB - In the solid state, the title compound, C20H19N3O2, adopts the keto-amine tautomeric form, with the H atom attached to the N atom, which participates in an intramolecular N - H⋯O hydrogen bond with an S(6) ring motif. The dihedral angles between the pyrazole ring and the phenyl and benzene rings are 3.69 (10) and 46.47 (9)°, respectively. In the crystal, molecules are linked by weak C - H⋯O hydrogen bonds, generating C(16) chains propagating in [301]. Weak aromatic π-π stacking interactions [centroid-centroid distances = 3.6123 (10) and 3.6665 (10) Å] link the chains into a three-dimensional network.

KW - Crystal structure

KW - Hydrogen bonding

KW - Keto-amine tautomeric form

KW - Pyrazolone derivatives

KW - Schiff bases

KW - π-πstacking interactions

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Crystal structure of (Z)-4-[1-(4-acetylanilino)ethyl-idene]-3-methyl-1-phenyl-1 H-pyrazol-5(4H)-one

Abstract

Bibliographical note

Keywords

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