2-(3-Methylphenyl)-1,2-benzoselenazol-3(2H)-one

Liyun Wang,Zhiqiang Guo,Xuehong Wei,Ying Xu

doi:10.1107/s2414314617005326

Abstract

In the title ebselen derivative, C14H11NOSe, the nine-membered benzisoselenazolyl ring system is approximately planar (r.m.s. deviation = 0.021 Å). The dihedral angle between its mean plane and that of the 3-methylphenyl ring is 5.37 (11)°. The five-membered isoselenazolyl ring is severely strained at the Se atom: Se—N = 1.889 (2) Å, Se—Car= 1.882 (3) Å and N—Se—Car= 83.30 (10)°. In the crystal, molecules are linked by C—H...O hydrogen bonds and short intermolecular Se...O contacts of 2.6917 (19) Å, forming chains along thec-axis direction. Neighbouring molecules are linked by offset π–π interactions [intercentroid distance = 3.535 (2) Å]. The chains are also linked by C—H...π interactions, forming a three-dimensional structure.

Highlights

In the title ebselen derivative, C14H11NOSe, the nine-membered benzisoselenazolyl ring system is approximately planar (r.m.s. deviation = 0.021 A )
Molecules are linked by C—HÁ Á ÁO hydrogen bonds and short intermolecular SeÁ Á ÁO contacts of 2.6917 (19) A, forming chains along the c-axis direction
We report on the synthesis and crystal structure of the 3-methylphenyl derivative of ebselen

Summary

Structure description

Ebselen (systematic name: 2-phenyl-1,2-benzoselenazol-3-one) is a synthetic organoselenium drug which has been reported to exhibit anti-inflammatory, anti-oxidant and cytoprotective activity (Mugesh & Singh, 2000; Mugesh et al, 2001a,b). The dihedral angle between its mean plane and the 3-methylphenyl ring is 5.37 (11). This value is much smaller than that reported for N-(2-methylphenyl)-1,2-benzoselenazol-3(2H)-one (Zhu et al, 2013) in which the 2-methylphenyl ring is inclined to the benzisoselenazolyl ring system by 78.15 (11). Molecules are linked by C—HÁ Á ÁO hydrogen bonds, and short Se1Á Á ÁOi contacts of 2.6917 (19) A [symmetry code: (i) x, Ày + 12, z À 12], forming chains along the c-axis direction (Table 1 and Fig. 2). Neighbouring molecules are linked by offset – interactions [Cg2Á Á ÁCg4i = 3.535 (2) A , Cg2 and Cg4 are the centroids of rings C1–C6 and Se1/N1/C8–C14, respectively, = 5.37 (11), interplanar distances = 3.499 (1) and 3.466 (1) A , slippage = 0.693 A ; symmetry code: (i) x, y À 1, z]. Cg2 and Cg3 are the centroids of rings C1–C6 and C9–C14, respectively

Bruker SMART CCD areadetector

Synthesis and crystallization

Data collection

Special details