Synthesis and Structures of Tetraphenylantimony Aroxides Ph4SbOAr (Ar = C6H3F2-2,4, C6H3F2-2,5, C6H3Cl-2-F-4)

The reactions of pentaphenylantimony with 2,4-difluoro-, 2,5-difluoro-, and 2-chloro-4-fluorophenol in a benzene–octane mixture of solvents afford tetraphenylantimony aroxides Ph4SbOC6H3F2-2,4 (I), Ph4SbOC6H3F2-2,5 (II), and Ph4SbOC6H3(Cl-2)(F-4) (III). According to the X-ray diffraction analysis data (CIF files CCDC nos. 1973286 (I), 1975709 (II), and 1973305 (III)), the antimony atoms in the compounds have the coordination of a distorted trigonal bipyramid with the aroxide oxygen atom in the axial position. The OSbС axial angles in compounds I–III are 177.86(6)°, 177.29(7)°, and 174.34(6)°, respectively. The geometric parameters of the molecules in compounds I–III are similar in the Sb−Ceq and Sb−O bond lengths (2.118(2)−2.127(2) and 2.1780(16) A in I; 2.122(2)−2.130(2) and 2.179(2) A in II; and 2.116(2)−2.119(2) and 2.1803(16) A in III). The structural organization in crystals of the compounds is due to weak hydrogen bonds involving F atoms and C–H∙∙∙π interactions. These interactions result in the organization of the molecules in the crystal of compound I into a three-dimensional network, paired chains are formed in compound II, and the molecules of compound III are organized into layers.