Synthesis and structural features of tris(4-fluorophenyl)antimony dipropiolate

Abstract

The interaction of tris(4-fluorophenylantimony) with propionic acid in the presence of cumene hydroperoxide (molar ratio 1:2:1) in ether gave tris(4-fluorophenyl)antimony dipropiolate (1), yielding 90%; the compound was identified by IR spectroscopy and X-ray structural analysis. The X-ray diffraction was performed on a D8 QUEST Bruker diffractometer. The crystallographic characteristics of the unit cell of the compound are as follows: monoclinic space group C2/c, a = 21.35(3), b = 8.290(7), c = 15.933(13) Å, β = 128.33(3), V = 2212(4) Å3, Z = 4, ρcalc = 1.637 g/cm3,  = 1.300 mm1, F(000) = 1072.0, crystal size 0.36  0.28  0.13 mm, data collection range for 2θ, deg: 6.5257, index range –28 ≤ h ≤ 28, –11 ≤ k ≤ 11, –21 ≤ l ≤ 19, number of measured reflections 27834, number of independent reflections 2802, Rint = 0.0254, GOOF = 1.078, number of parameters 286, R1 = 0.0162, wR2 = 0.0401. According to the X-ray diffraction data, the antimony atoms in the compound have a distorted trigonal-bipyramidal coordination with the oxygen atoms of the carboxylate groups in axial positions. All ligands are disordered in the structure. The CSbO axial angle is 175.9(2)º. The sum of the CSbC equatorial angles is 357.1(9)º, the Sb–Ceq distances [2.109(7), 2.117(5), 2.146(5) Å] are significantly shorter than the Sb–O bond lengths [2.244(4) Å]. The organization of molecules in the crystal of compound 1 is due to the F∙∙∙H hydrogen bonds (2.25 Å) and CH∙∙∙π-interactions of the rings of the aryl and carboxyl ligands. Complete tables of atomic coordinates, bond lengths, and bond angles have been deposited with the Cambridge Crystallographic Data Center (No. 2421858; deposit@ccdc.cam.ac.uk or http://www.ccdc.cam.ac.uk/data_request/cif).