3-(4-Chlorophenoxy)-1-(4-methoxyphenyl)-4-(4-nitrophenyl)azetidin-2-one

In the title compound, C22H17ClN2O5, the nearly planar four-membered β-lactam ring [maximum deviation of 0.016 (1) for the N atom] makes dihedral angles of 53.07 (9), 73.19 (9) and 6.61 (9)° with the chloro-, nitro- and methoxybenzene rings, respectively. The crystal structure is stabilized by C—H⋯O hydrogen bonds, a weak C—H⋯π interaction and a π–π stacking interaction [centroid–centroid distance = 3.6513 (8) Å] between the methoxybenzene rings of inversion-related molecules.

[1]  Seid Ali Torabi Badrabady,et al.  3-(2,4-Dichlorophenoxy)-1-(4-methoxyphenyl)-4-(3-nitrophenyl)azetidin-2-one , 2010, Acta crystallographica. Section E, Structure reports online.

[2]  A. Jarrahpour,et al.  Efficient one-pot synthesis of 2-azetidinones from acetic acid derivatives and imines using methoxymethylene-N,N-dimethyliminium salt , 2010 .

[3]  良二 上田.  J. Appl. Cryst.の発刊に際して , 1970 .

[4]  Louis J. Farrugia,et al.  WinGX suite for small-molecule single-crystal crystallography , 1999 .

[5]  A. Jarrahpour,et al.  4-(9-Anthryl)-1-(2,4-dimethoxyphenyl)spiro[azetidine-3,9′-xanthen]-2-one , 2009, Acta crystallographica. Section E, Structure reports online.

[6]  A. Jarrahpour,et al.  4-(9-Anthryl)-1-(4-methoxyphenyl)spiro[azetidin-3,9′-xanthen]-2-one , 2008, Acta crystallographica. Section E, Structure reports online.

[7]  D. Khalili,et al.  Synthesis of some mono- and bis-spiro-β-lactams of benzylisatin , 2007 .

[8]  Louis J. Farrugia,et al.  ORTEP-3 for Windows - a version of ORTEP-III with a Graphical User Interface (GUI) , 1997 .

[9]  G. Sheldrick.  A short history of SHELX. , 2008, Acta crystallographica. Section A, Foundations of crystallography.

[10]  Mehmet Akkurt,et al.  4-(9-Anthryl)-1-(1-naphthyl)spiro[azetidine-3,9′-xanthen]-2-one n-hexane hemisolvate , 2008, Acta crystallographica. Section E, Structure reports online.

[11]  Anthony L. Spek,et al.  Structure validation in chemical crystallography , 2009, Acta crystallographica. Section D, Biological crystallography.

[12]  A. Jarrahpour,et al.  Synthesis of novel N-sulfonyl monocyclic beta-lactams as potential antibacterial agents. , 2006, Molecules.

[13]  M. Koketsu,et al.  Synthesis of selenium-containing bicyclic beta-lactams via alkene metathesis. , 2009, Organic & biomolecular chemistry.

[14]  Seid Ali Torabi Badrabady,et al.  (3R*,4R*)-1-(4-Chlorophenyl)-4-[2-hydroxy-3-(morpholinomethyl)phenyl]-3-phenoxyazetidin-2-one , 2011, Acta crystallographica. Section E, Structure reports online.

[15]  A. Jarrahpour,et al.  4-(9-Anthryl)-1-(3-bromophenyl)spiro[azetidine-3,9′-xanthen]-2-one , 2009, Acta crystallographica. Section E, Structure reports online.

[16]  S. Yalcin,et al.  4-(9-Anthryl)-1-(2-methoxyphenyl)spiro[azetidin-3,9′-xanthen]-2-one , 2009, Acta crystallographica. Section E, Structure reports online.

[17]  F. Becker,et al.  Synthesis of anticancer β-lactams: mechanism of action , 2004 .