Crystal structure of 2-[4-(4-chlorophen-yl)-1-(4-methoxyphenyl)-2-oxoazetidin-3-yl]benzo[de]isoquinoline-1, 3-dione dimethyl sulfoxide monosolvate

Ísmail Çelik, Mehmet Akkurt*, Aliasghar Jarrahpour, Javad Ameri Rad, Ömer Çelik, W. T A Harrison (Editor)

*Corresponding author for this work

Research output: Contribution to journalArticle

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Abstract

In the title solvated compound, C28H19N2O4C2H6OS, the central β-lactam ring is almost planar (r.m.s. deviation = 0.002 Å). It makes dihedral angles of 1.92 (11), 83.23 (12) and 74.90 (10)° with the methoxy- and chlorophenyl rings and the ring plane of the 1H-benzo[de]isoquinoline-1, 3(2H)-dione group [maximum deviation = 0.089 (1)], respectively. An intramolecular C - H⋯O hydrogen bond closes an S(6) ring and helps to establish the near coplanarity of the β-lactam and methoxybenzene rings. In the crystal, the components are linked by C - H⋯O hydrogen bonds, C - H⋯π=i interactions and aromatic π-π stacking interactions [centroid-to-centroid distances = 3.6166 (10) and 3.7159 (10) Å], resulting in a three-dimensional network, The dimethyl sulfoxide solvent molecule is disordered over two sets of sites in a 0.847 (2):0.153 (2) ratio.

Original languageEnglish
Pages (from-to)o129-o130
Number of pages2
JournalActa Crystallographica Section E: Structure Reports Online
Volume71
Issue number2
Early online date28 Jan 2015
DOIs
Publication statusPublished - 1 Feb 2015

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Lactams
Dimethyl sulfoxide
Dione
Dimethyl Sulfoxide
Hydrogen bonds
Crystal structure
crystal structure
rings
Dihedral angle
centroids
Crystals
Molecules
hydrogen bonds
coplanarity
deviation
dihedral angle
isoquinoline
interactions
crystals
molecules

Keywords

  • 1 H-benzo[de]isoquinoline-1,3(2H)-dione group
  • Azetidin-2-ones
  • Crystal structure
  • Disorder
  • -lactam ring

ASJC Scopus subject areas

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

Cite this

Crystal structure of 2-[4-(4-chlorophen-yl)-1-(4-methoxyphenyl)-2-oxoazetidin-3-yl]benzo[de]isoquinoline-1, 3-dione dimethyl sulfoxide monosolvate. / Çelik, Ísmail; Akkurt, Mehmet; Jarrahpour, Aliasghar; Rad, Javad Ameri; Çelik, Ömer; Harrison, W. T A (Editor).

In: Acta Crystallographica Section E: Structure Reports Online, Vol. 71, No. 2, 01.02.2015, p. o129-o130.

Research output: Contribution to journalArticle

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abstract = "In the title solvated compound, C28H19N2O4C2H6OS, the central β-lactam ring is almost planar (r.m.s. deviation = 0.002 {\AA}). It makes dihedral angles of 1.92 (11), 83.23 (12) and 74.90 (10)° with the methoxy- and chlorophenyl rings and the ring plane of the 1H-benzo[de]isoquinoline-1, 3(2H)-dione group [maximum deviation = 0.089 (1)], respectively. An intramolecular C - H⋯O hydrogen bond closes an S(6) ring and helps to establish the near coplanarity of the β-lactam and methoxybenzene rings. In the crystal, the components are linked by C - H⋯O hydrogen bonds, C - H⋯π=i interactions and aromatic π-π stacking interactions [centroid-to-centroid distances = 3.6166 (10) and 3.7159 (10) {\AA}], resulting in a three-dimensional network, The dimethyl sulfoxide solvent molecule is disordered over two sets of sites in a 0.847 (2):0.153 (2) ratio.",
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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 JAR thank the Shiraz University Research Council for financial support (grant No. 93-GR–SC-23).",
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AU - Çelik, Ísmail

AU - Akkurt, Mehmet

AU - Jarrahpour, Aliasghar

AU - Rad, Javad Ameri

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 JAR thank the Shiraz University Research Council for financial support (grant No. 93-GR–SC-23).

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N2 - In the title solvated compound, C28H19N2O4C2H6OS, the central β-lactam ring is almost planar (r.m.s. deviation = 0.002 Å). It makes dihedral angles of 1.92 (11), 83.23 (12) and 74.90 (10)° with the methoxy- and chlorophenyl rings and the ring plane of the 1H-benzo[de]isoquinoline-1, 3(2H)-dione group [maximum deviation = 0.089 (1)], respectively. An intramolecular C - H⋯O hydrogen bond closes an S(6) ring and helps to establish the near coplanarity of the β-lactam and methoxybenzene rings. In the crystal, the components are linked by C - H⋯O hydrogen bonds, C - H⋯π=i interactions and aromatic π-π stacking interactions [centroid-to-centroid distances = 3.6166 (10) and 3.7159 (10) Å], resulting in a three-dimensional network, The dimethyl sulfoxide solvent molecule is disordered over two sets of sites in a 0.847 (2):0.153 (2) ratio.

AB - In the title solvated compound, C28H19N2O4C2H6OS, the central β-lactam ring is almost planar (r.m.s. deviation = 0.002 Å). It makes dihedral angles of 1.92 (11), 83.23 (12) and 74.90 (10)° with the methoxy- and chlorophenyl rings and the ring plane of the 1H-benzo[de]isoquinoline-1, 3(2H)-dione group [maximum deviation = 0.089 (1)], respectively. An intramolecular C - H⋯O hydrogen bond closes an S(6) ring and helps to establish the near coplanarity of the β-lactam and methoxybenzene rings. In the crystal, the components are linked by C - H⋯O hydrogen bonds, C - H⋯π=i interactions and aromatic π-π stacking interactions [centroid-to-centroid distances = 3.6166 (10) and 3.7159 (10) Å], resulting in a three-dimensional network, The dimethyl sulfoxide solvent molecule is disordered over two sets of sites in a 0.847 (2):0.153 (2) ratio.

KW - 1 H-benzo[de]isoquinoline-1,3(2H)-dione group

KW - Azetidin-2-ones

KW - Crystal structure

KW - Disorder

KW - -lactam ring

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