Reactions of pentaphenylantimony with 1,2,3,4-tetrahydroacridine-9-carboxylic and coumarin-3-carboxylic acids

Pentaphenylantimony reacts with 1,2,3,4-tetrahydroacridine-9-carboxylic and coumarin-3-carboxylic acids in benzene at room temperature to form tetraphenylantimony carboxylates Ph4SbOC(O)R, R = C13H12N (1), C9H5O2 (2), the structure of which has been determined by X-ray diffraction analysis (XRD). According to the X-ray diffraction data, the antimony atoms in molecules 1 and 2 have a distorted trigonal bipyramidal coordination with three phenyl substituents in the equatorial plane, the CSbO axial angles are 175.85(7)° and 177.6(6)°, the sum of the angles between equatorial bonds are 356.31(8)° and 356.5(6)°. The Sb-C equatorial bonds (2.112(2)-2.125(2) Å for 1 and 2.128(16)-2.131(16) Å for 2 are shorter than the axial ones (2.174(2) Å for 1 and 2.224(12) Å for 2. The Sb-O bond lengths (2.2793(18) Å in 1 and 2.204(13) Å in 2) exceed the sum of the covalent radii of antimony and oxygen atoms. It has been established that the geometric characteristics of the free coumarin-3-carboxylic acid molecule (3) and the acid residue included in complex 2 differ significantly. The X-ray diffraction data: a D8 Quest diffractometer from Bruker (MoKα radiation, λ = 0.71073 Å, graphite monochromator, at 293(2) K. [(1) C38H32NO2Sb, M = 656.40; monoclinic system, space group Р21/c; crystal size 0.48´0.23´0.18 mm; cell parameters: a = 9.063(4) Å, b = 15.911(8) Å, c = 21.495(11) Å; β = 94.719(16)°, V = 3089(3) Å3, Z = 4; rcalc = 1.411 g/cm3; m = 0.927 mm-1; F(000) = 1336.0; collection region for 2q: 5.66-62.12°; -13 ≤ h ≤ 10, -23 ≤ k ≤ 23, -31 ≤ l ≤ 31; total reflections 146090; independent reflections 9883 (Rint = 0.0591); GOOF = 1.052; R-factor is 0.0338; (2) C34H24O4Sb, M = 619.29; triclinic system, space group P-1; crystal size 0.61´0.42´0.29 mm; cell parameters: a = 9.533(4) Å, b = 10.560(4) Å, c = 16.397(6) Å; a = 97.431(13)°, β = 98.49(2)°, g = 108.962(12)°, V = 1516.1(9) Å3, Z = 2; rcalc = 1.357 g/cm3; m = 0.944 mm-1; F(000) = 624.0; collection region at 2q: 5.7-55.64°; -12 ≤ h ≤ 12, -13 ≤ k ≤ 13, -21 ≤ l ≤ 21; total reflections 19837; independent reflections 12162 (Rint = 0.0707); GOOF = 1.087; R-factor is 0.0543; (3) 3 C10H6O4, M = 190.15; monoclinic system, space group Р21/n; crystal size 0.11 ´ 0.24 ´ 0.29 mm; cell parameters: a = 11.390(6) Å, b = 5.534(3) Å, c = 13.890(8) Å; a = 90.00°, β = 106.33(3)°, g = 90.00°, V = 840.1(7) Å3, Z = 4; rcalc = 1.503 g/cm3; m = 0.118 mm -1; F(000) = 392.0; collection region at 2q: 6.12-55.04°; -14 ≤ h ≤ 14,7 ≤ k ≤ 7, -18 ≤ l ≤ 17; total reflections 23991; independent reflections 1917 (Rint = 0.0263); GOOF = 1.072; R-factor is 0.0406]. Keywords: pentaphenylantimony, 1,2,3,4-tetrahydroacridine-9-carboxylic acid, coumarin-3-carboxylic acid, tetraphenylantimony carboxylate, molecular structure, X-ray diffraction analysis