Formation of isolated guest dimers vs. host-guest coordination. X-Ray crystal structures of four carboxylic acid inclusion compounds formed by roof-shaped and scissor-like host molecules

Abstract

The crystal structures of the inclusion compounds oftrans-9,10-dihydro-9,10-ethano-anthracene-11,12-dicarboxylic acid host (1) with formic acid (1a), acetic acid (1b), and propionic acid (1c) as guests, and of the coordinatoclathrate of the 1,1′-binaphthyl-2,2′-dicarboxylic acid host (2) with acetic acid as guest (2b) have been studied by single crystal X-ray diffraction. These studies show that inclusion of small carboxylic acids by carboxylic acid hosts like1 and2 results in formation of isolated, hydrogen-bonded guest dimers. Additional H-bond contacts between host and guest carboxylic groups are only formed in cases1a and2b. The dimeric acidic guest units are sitting in the cavities of the host or host-guest framework and have no other interactions than those of a weak Van der Waals' type with the neighbouring molecules. Crystal data:1·formic acid (1:2): triclinic (PĪ),a = 11.6769(6),b = 9.4067(4),c = 9.0020(4) A,a = 81.522(4), β = 100.310(6), γ = 104.208(6)°,Z = 2,R = 0.048 for 2392 reflections;1·acetic acid (1:1): monoclinic (P21/n),a = 9.717(2),b = 14.462(2),c = 13.038(3)A, β = 104.27(1)°,Z=4,R=0.046 for 3042 observations;1·propionic acid (1:1): monoclinic (P21/n),a = 9.897(4),b = 14.671(7),c = 13.284(7) A, β = 105.92(6)°,Z = 4,R = 0.056 for 2302 reflections;2·acetic acid (2:3): triclinic (PĪ),a = 12.746(1),b = 17.781(2),c = 11.010(1) A, α = 105.606(4), β = 112.992(8), γ = 81.175(6)°,Z = 2,R = 0.067 for 4375 observations.