Crystal structure of 3-(4-chlorophenoxy)-4-(2-nitrophenyl)azetidin-2-one with an unknown solvate

Sevim Türktekin Çelikesir; Mehmet Akkurt; Aliasghar Jarrahpour; Habib Allah Shafie; Ömer Çelik; W. T A Harrison

doi:10.1107/S2056989014025845

Crystal structure of 3-(4-chlorophenoxy)-4-(2-nitrophenyl)azetidin-2-one with an unknown solvate

Sevim Türktekin Çelikesir, Mehmet Akkurt^*, Aliasghar Jarrahpour, Habib Allah Shafie, Ömer Çelik, W. T A Harrison (Editor)

^*Corresponding author for this work

Chemistry

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

10 Downloads (Pure)

Abstract

In the title compound, C₁₅H₁₁ClN₂O₄, the central β-lactam ring is approximately planar [maximum deviation = 0.044 (2) Å for the N atom from the mean plane] and subtends dihedral angles of 61.17 (11) and 40.21 (12)°, respectively, with the nitro and chlorobenzene rings. Both substituents lie to the same side of the β-lactam core. In the crystal, N - H⋯O hydrogen bonds link the molecules into C(4) chains propagating in [010]. The chains are cross-linked by C - H⋯O and weak C - H⋯π interactions, generating a three-dimensional network. The solvent molecules were found to be highly disordered and their contribution to the scattering was removed with the SQUEEZE procedure in PLATON [Spek (2009). Acta Cryst. D65, 148-155], which indicated a solvent cavity of volume 318 Å³ containing approximately 114 electrons. These solvent molecules are not considered in the given chemical formula and other crystal data.

Original language	English
Pages (from-to)	o8-o9
Number of pages	2
Journal	Acta Crystallographica Section E: Structure Reports Online
Volume	71
Issue number	1
DOIs	https://doi.org/10.1107/S2056989014025845
Publication status	Published - 1 Jan 2015

Bibliographical note

Acknowledgements
The authors are indebted to the X-ray laboratory of Dicle University Scientific and Technological Applied and Research Center, Diyarbakir, Turkey, for use of the X-ray diffractometer. AJ and HAS thank the Shiraz University Research Council for financial support.

Keywords

C - H⋯πinteractions
C(4) chain
Crystal structure
Hydrogen bonding
Hydrogen bonds
N-unsubstituted 2-azetidinone
β-lactam ring

Access to Document

10.1107/S2056989014025845Licence: CC BY

Crystal structure of 3-(4-chlorophenoxy)-4-(2-nitrophenyl)azetidin-2-one with an unknown solvate
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. https://creativecommons.org/licenses/by/4.0/
Final published version, 332 KBLicence: CC BY

Cite this

@article{ca4912732ecd45cbbaf441dd9770d024,

title = "Crystal structure of 3-(4-chlorophenoxy)-4-(2-nitrophenyl)azetidin-2-one with an unknown solvate",

abstract = "In the title compound, C15H11ClN2O4, the central β-lactam ring is approximately planar [maximum deviation = 0.044 (2) {\AA} for the N atom from the mean plane] and subtends dihedral angles of 61.17 (11) and 40.21 (12)°, respectively, with the nitro and chlorobenzene rings. Both substituents lie to the same side of the β-lactam core. In the crystal, N - H⋯O hydrogen bonds link the molecules into C(4) chains propagating in [010]. The chains are cross-linked by C - H⋯O and weak C - H⋯π interactions, generating a three-dimensional network. The solvent molecules were found to be highly disordered and their contribution to the scattering was removed with the SQUEEZE procedure in PLATON [Spek (2009). Acta Cryst. D65, 148-155], which indicated a solvent cavity of volume 318 {\AA}3 containing approximately 114 electrons. These solvent molecules are not considered in the given chemical formula and other crystal data.",

keywords = "C - H⋯πinteractions, C(4) chain, Crystal structure, Hydrogen bonding, Hydrogen bonds, N-unsubstituted 2-azetidinone, β-lactam ring",

author = "{\c C}elikesir, {Sevim T{\"u}rktekin} and Mehmet Akkurt and Aliasghar Jarrahpour and Shafie, {Habib Allah} and {\"O}mer {\c C}elik and Harrison, {W. T A}",

note = "Acknowledgements The authors are indebted to the X-ray laboratory of Dicle University Scientific and Technological Applied and Research Center, Diyarbakir, Turkey, for use of the X-ray diffractometer. AJ and HAS thank the Shiraz University Research Council for financial support. ",

year = "2015",

month = jan,

day = "1",

doi = "10.1107/S2056989014025845",

language = "English",

volume = "71",

pages = "o8--o9",

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

issn = "1600-5368",

publisher = "International Union of Crystallography",

number = "1",

}

TY - JOUR

T1 - Crystal structure of 3-(4-chlorophenoxy)-4-(2-nitrophenyl)azetidin-2-one with an unknown solvate

AU - Çelikesir, Sevim Türktekin

AU - Akkurt, Mehmet

AU - Jarrahpour, Aliasghar

AU - Shafie, Habib Allah

AU - Çelik, Ömer

A2 - Harrison, W. T A

N1 - Acknowledgements The authors are indebted to the X-ray laboratory of Dicle University Scientific and Technological Applied and Research Center, Diyarbakir, Turkey, for use of the X-ray diffractometer. AJ and HAS thank the Shiraz University Research Council for financial support.

PY - 2015/1/1

Y1 - 2015/1/1

N2 - In the title compound, C15H11ClN2O4, the central β-lactam ring is approximately planar [maximum deviation = 0.044 (2) Å for the N atom from the mean plane] and subtends dihedral angles of 61.17 (11) and 40.21 (12)°, respectively, with the nitro and chlorobenzene rings. Both substituents lie to the same side of the β-lactam core. In the crystal, N - H⋯O hydrogen bonds link the molecules into C(4) chains propagating in [010]. The chains are cross-linked by C - H⋯O and weak C - H⋯π interactions, generating a three-dimensional network. The solvent molecules were found to be highly disordered and their contribution to the scattering was removed with the SQUEEZE procedure in PLATON [Spek (2009). Acta Cryst. D65, 148-155], which indicated a solvent cavity of volume 318 Å3 containing approximately 114 electrons. These solvent molecules are not considered in the given chemical formula and other crystal data.

AB - In the title compound, C15H11ClN2O4, the central β-lactam ring is approximately planar [maximum deviation = 0.044 (2) Å for the N atom from the mean plane] and subtends dihedral angles of 61.17 (11) and 40.21 (12)°, respectively, with the nitro and chlorobenzene rings. Both substituents lie to the same side of the β-lactam core. In the crystal, N - H⋯O hydrogen bonds link the molecules into C(4) chains propagating in [010]. The chains are cross-linked by C - H⋯O and weak C - H⋯π interactions, generating a three-dimensional network. The solvent molecules were found to be highly disordered and their contribution to the scattering was removed with the SQUEEZE procedure in PLATON [Spek (2009). Acta Cryst. D65, 148-155], which indicated a solvent cavity of volume 318 Å3 containing approximately 114 electrons. These solvent molecules are not considered in the given chemical formula and other crystal data.

KW - C - H⋯πinteractions

KW - C(4) chain

KW - Crystal structure

KW - Hydrogen bonding

KW - Hydrogen bonds

KW - N-unsubstituted 2-azetidinone

KW - β-lactam ring

UR - http://www.scopus.com/inward/record.url?scp=84928129062&partnerID=8YFLogxK

U2 - 10.1107/S2056989014025845

DO - 10.1107/S2056989014025845

M3 - Article

AN - SCOPUS:84928129062

SN - 1600-5368

VL - 71

SP - o8-o9

JO - Acta Crystallographica Section E: Structure Reports Online

JF - Acta Crystallographica Section E: Structure Reports Online

IS - 1

ER -

Crystal structure of 3-(4-chlorophenoxy)-4-(2-nitrophenyl)azetidin-2-one with an unknown solvate

Abstract

Bibliographical note

Keywords

Access to Document

Other files and links

Fingerprint

Cite this