Crystal structure of 4-[(E)-(4-nitro-benzylidene)amino]phenol

Zeliha Atioʇlu; Mehmet Akkurt; Aliasghar Jarrahpour; Edris Ebrahimi; Orhan Büyükgüngör; W.T.A. Harrison

doi:10.1107/S2056989015000511

Crystal structure of 4-[(E)-(4-nitro-benzylidene)amino]phenol

Zeliha Atioʇlu, Mehmet Akkurt^*, Aliasghar Jarrahpour, Edris Ebrahimi, Orhan Büyükgüngör, W.T.A. Harrison (Editor)

^*Corresponding author for this work

Chemistry

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Abstract

The asymmetric unit of the title compound, C₁₃H₁₀N₂O₃, contains four independent molecules (I, II, III and IV). Molecule IV shows whole-molecule disorder over two sets of adjacent sites in a 0.669 (10):0.331 (10) ratio. The dihedral angles between the aromatic rings are 32.30 (13)° in molecule I, 2.24 (14)° in II, 41.61 (13)° in III, 5.0 (5)° in IV (major component) and 10.2 (3)° in IV (minor component). In the crystal, molecules are linked into layers lying parallel to (024) by C - H⋯O and O - H⋯O interactions. The layers interact by C - H⋯π and weak aromatic π-π stacking interactions [centroid-centroid distances = 3.8476 (16), 3.725 (3) and 3.733 (5) Å].

Original language	English
Pages (from-to)	o113-o114
Number of pages	2
Journal	Acta Crystallographica Section E: Structure Reports Online
Volume	71
Issue number	2
Early online date	17 Jan 2015
DOIs	https://doi.org/10.1107/S2056989015000511
Publication status	Published - 1 Feb 2015

Keywords

C - H⋯πinteractions
Crystal structure
Hydrogen bonding
Nitroaromatic compounds
Whole-molecule disorder
π-πstacking interactions

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Crystal structure of 4-[(E)-(4-nitrobenzylidene)amino]phenol
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title = "Crystal structure of 4-[(E)-(4-nitro-benzylidene)amino]phenol",

abstract = "The asymmetric unit of the title compound, C13H10N2O3, contains four independent molecules (I, II, III and IV). Molecule IV shows whole-molecule disorder over two sets of adjacent sites in a 0.669 (10):0.331 (10) ratio. The dihedral angles between the aromatic rings are 32.30 (13)° in molecule I, 2.24 (14)° in II, 41.61 (13)° in III, 5.0 (5)° in IV (major component) and 10.2 (3)° in IV (minor component). In the crystal, molecules are linked into layers lying parallel to (024) by C - H⋯O and O - H⋯O interactions. The layers interact by C - H⋯π and weak aromatic π-π stacking interactions [centroid-centroid distances = 3.8476 (16), 3.725 (3) and 3.733 (5) {\AA}].",

keywords = "C - H⋯πinteractions, Crystal structure, Hydrogen bonding, Nitroaromatic compounds, Whole-molecule disorder, π-πstacking interactions",

author = "Zeliha Atioʇlu and Mehmet Akkurt and Aliasghar Jarrahpour and Edris Ebrahimi and Orhan B{\"u}y{\"u}kg{\"u}ng{\"o}r and W.T.A. Harrison",

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). AJ and EE thank the Shiraz University Research Council for financial support.",

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AU - Atioʇlu, Zeliha

AU - Akkurt, Mehmet

AU - Jarrahpour, Aliasghar

AU - Ebrahimi, Edris

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). AJ and EE thank the Shiraz University Research Council for financial support.

PY - 2015/2/1

Y1 - 2015/2/1

N2 - The asymmetric unit of the title compound, C13H10N2O3, contains four independent molecules (I, II, III and IV). Molecule IV shows whole-molecule disorder over two sets of adjacent sites in a 0.669 (10):0.331 (10) ratio. The dihedral angles between the aromatic rings are 32.30 (13)° in molecule I, 2.24 (14)° in II, 41.61 (13)° in III, 5.0 (5)° in IV (major component) and 10.2 (3)° in IV (minor component). In the crystal, molecules are linked into layers lying parallel to (024) by C - H⋯O and O - H⋯O interactions. The layers interact by C - H⋯π and weak aromatic π-π stacking interactions [centroid-centroid distances = 3.8476 (16), 3.725 (3) and 3.733 (5) Å].

AB - The asymmetric unit of the title compound, C13H10N2O3, contains four independent molecules (I, II, III and IV). Molecule IV shows whole-molecule disorder over two sets of adjacent sites in a 0.669 (10):0.331 (10) ratio. The dihedral angles between the aromatic rings are 32.30 (13)° in molecule I, 2.24 (14)° in II, 41.61 (13)° in III, 5.0 (5)° in IV (major component) and 10.2 (3)° in IV (minor component). In the crystal, molecules are linked into layers lying parallel to (024) by C - H⋯O and O - H⋯O interactions. The layers interact by C - H⋯π and weak aromatic π-π stacking interactions [centroid-centroid distances = 3.8476 (16), 3.725 (3) and 3.733 (5) Å].

KW - C - H⋯πinteractions

KW - Crystal structure

KW - Hydrogen bonding

KW - Nitroaromatic compounds

KW - Whole-molecule disorder

KW - π-πstacking interactions

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Crystal structure of 4-[(E)-(4-nitro-benzylidene)amino]phenol

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