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

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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 languageEnglish
Pages (from-to)o8-o9
Number of pages2
JournalActa Crystallographica Section E: Structure Reports Online
Volume71
Issue number1
DOIs
Publication statusPublished - 1 Jan 2015

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Lactams
Crystal structure
crystal structure
Molecules
molecules
Crystals
chlorobenzenes
rings
Dihedral angle
crystals
dihedral angle
Hydrogen bonds
Scattering
hydrogen bonds
deviation
Atoms
cavities
Electrons
scattering
atoms

Keywords

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

ASJC Scopus subject areas

  • Condensed Matter Physics
  • Materials Science(all)
  • Chemistry(all)

Cite this

Crystal structure of 3-(4-chlorophenoxy)-4-(2-nitrophenyl)azetidin-2-one with an unknown solvate. / Çelikesir, Sevim Türktekin; Akkurt, Mehmet; Jarrahpour, Aliasghar; Shafie, Habib Allah; Çelik, Ömer; Harrison, W. T A (Editor).

In: Acta Crystallographica Section E: Structure Reports Online, Vol. 71, No. 1, 01.01.2015, p. o8-o9.

Research output: Contribution to journalArticle

Çelikesir, Sevim Türktekin ; Akkurt, Mehmet ; Jarrahpour, Aliasghar ; Shafie, Habib Allah ; Çelik, Ömer ; Harrison, W. T A (Editor). / Crystal structure of 3-(4-chlorophenoxy)-4-(2-nitrophenyl)azetidin-2-one with an unknown solvate. In: Acta Crystallographica Section E: Structure Reports Online. 2015 ; Vol. 71, No. 1. pp. o8-o9.
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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.",
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AU - Çelik, Ömer

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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.

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