1-Phenyl-2-(1H-1,2,4-triazol-1-yl)ethanone

In the molecule of the title compound, C10H9N3O, the triazole and phenyl rings are nearly perpendicular to each other, with a dihedral angle of 88.72 (4)°. In the crystal structure, intermolecular C—H⋯O and C—H⋯N hydrogen bonds link the molecules. There are C—H⋯π contacts between the 1,2,4-triazole rings, and between the phenyl and 1,2,4-triazole rings, and there is a weak π–π contact between the 1,2,4-triazole and phenyl rings [centroid-to-centroid distance = 4.547 (1) Å].

[1]  R. Hale,et al.  Cyclization of 1,2,4-triazenes to 1,2,4-triazoles using oxidizing reagents—NaClO, Ca(ClO)2, Dess–Martin periodinane and Ley's TPAP/NMO , 2001 .

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

[3]  N. Blaton,et al.  cis-2-sec-Butyl-4-{4-[4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-1-piperazinyl]phenyl}-2,4-dihydro-3H-1,2,4-triazol-3-one (Itraconazole) , 1996 .

[4]  Anthony L. Spek,et al.  Journal of , 1993 .

[5]  H. Dai,et al.  Synthesis and biological activities of new 1H-1,2,4-triazole derivatives containing ferrocenyl moiety , 2006 .

[6]  Tuncer Hökelek,et al.  2-(1H-Benzimidazol-1-yl)-1-phenylethanone , 2008, Acta crystallographica. Section E, Structure reports online.

[7]  T. Hökelek,et al.  2-(1H-benzimidazol-1-yl)-1-phenylethanone oxime , 2007 .

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

[9]  B. Kalluraya,et al.  Synthesis, characterisation and antifungal activity of some N-bridged heterocycles derived from 3-(3-bromo-4-methoxyphenyl)-4-amino-5-mercapto-1,2,4-triazole. , 1996, Farmaco.

[10]  N. Blaton,et al.  The Crystal Structure of 1‐{2,4‐Dichloro‐β‐ [(2,4‐Dichloro‐Benzyl)Oxy] Phenethyl} Imidazole Hemihydrate: Miconazole. 1/2 H2O , 2010 .

[11]  G. Bodey,et al.  Azole antifungal agents. , 1992, Clinical infectious diseases : an official publication of the Infectious Diseases Society of America.

[12]  A. Freer,et al.  Structure of econazole , 1986 .

[13]  Khouloud A. Alkhamis,et al.  Preparation and crystal characterization of a polymorph, a monohydrate, and an ethyl acetate solvate of the antifungal fluconazole. , 2004, Journal of pharmaceutical sciences.

[14]  Z. Sui,et al.  SAR studies of diaryltriazoles against bacterial two-component regulatory systems and their antibacterial activities. , 1998, Bioorganic & medicinal chemistry letters.

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

[16]  N. Blaton,et al.  cis-1-Acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-1-imidazolylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine: ketoconazole. A crystal structure with disorder , 1979 .

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