engleski

Whole-molecule disorder in the crystal structure of (1-adamantyl)methyl-1-adamantanecarboxylate

Two adamantyl esters, 1-(adamantyl)methyl-1-adamantanecarboxylate (1) and bis(1-adamantyl)methyl-1, 3-adamantanedicarboxylate (2) were prepared and characterized by spectroscopic methods [1]. Esters 1 and 2 were prepared in good yield by coupling of the corresponding acid chloride and 1-(hydroxymethyl)-adamantane in the presence of 4-(dimethylamino)pyridine at room temperature. The structure of ester 1 has been determined by single-crystal X-ray diffraction. The solid-state structure of 1 in the orthorhombic space group Pbcn [a = 18.129(2) Å , b = 9.9360(4) Å , c = 9.9744(7) Å ] shows four-fold whole-molecule disorder. The ester molecule occupies one of the two different sites, and at each site there is additional disorder over a crystallographic 2-fold rotation axis passing almost through O2 atom. The ester molecules are held together only by van der Waals interactions. This, together with the symmetry and metrics of the unit cell, allows the ” misorientation” of molecules thus resulting in the observed whole-molecule disorder in the crystal structure of 1.

Whole-molecule disorder; crystal structure; X-ray diffraction

nije evidentirano