Original scientific paper

(1-Adamantyl)methyl esters: whole-molecule disorder in the crystal structure of (1-adamantyl)methyl-1-adamantanecarboxylate

Dalibor Milić ; Laboratory of General and Inorganic Chemistry, Department of Chemistry, Faculty of Science, Horvatovac 102a, 10000 Zagreb, Croatia
Marija Alešković ; Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, POB 180, 10002 Zagreb, Croatia
Dubravka Matković-Čalogović orcid.org/0000-0003-4909-8312 ; Laboratory of General and Inorganic Chemistry, Department of Chemistry, Faculty of Science, Horvatovac 102a, 10000 Zagreb, Croatia
Kata Mlinarić-Majerski orcid.org/0000-0001-6282-1662 ; Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, POB 180, 10002 Zagreb, Croatia

Abstract

Two (1-adamantyl)methyl esters, (1-adamantyl)methyl-1-adamantanecarboxylate (1) and bis[(1-adamantyl)methyl]-1,3-adamantanedicarboxylate (2) were prepared in good yields and characterized by spectroscopic methods. The structure of 1 was determined by single-crystal X-ray diffraction structural analysis. The structure shows two kinds of whole-molecule disorder: the ester molecule statistically occupies two different sites in the crystal asymmetric unit with occupancies of 95 and 5 % (positional disorder), and at each of the sites there is additional disorder over a crystallographic 2-fold rotation axis (orientational disorder). Analysis of diffuse scattering patterns in the diffraction images revealed the positional disorder as stacking disorder of molecular layers with two-dimensional translational symmetry. In the absence of other, more directional interactions, the molecules in the crystal structure of 1 are held together only by van der Waals interactions which provide the rationale for the observed whole-molecule disorder.

Keywords

adamantane; (1-adamantyl)methyl esters; X-ray diffraction analysis; whole-molecule disorder; stacking disorder; diffuse scattering

Hrčak ID:

45630

URI

https://hrcak.srce.hr/45630

Publication date:

20.12.2009.

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