Crystal structure and absolute configuration of (3a R,3'a R,7a S,7'a S)-2,2,2',2'-tetra-methyl-3a,6,7,7a,3'a,6',7',7'a-octa-hydro-4,4'-bi[1,3-benzodioxol-yl], obtained from a Pd-catalyzed homocoupling reaction

Mario A Macías; Enrique Pandolfi; Valeria Schapiro; Gustavo P Silveira; Guilherme D Vilela; Leopoldo Suescun

doi:10.1107/S2056989016019927

Crystal structure and absolute configuration of (3a R,3'a R,7a S,7'a S)-2,2,2',2'-tetra-methyl-3a,6,7,7a,3'a,6',7',7'a-octa-hydro-4,4'-bi[1,3-benzodioxol-yl], obtained from a Pd-catalyzed homocoupling reaction

Acta Crystallogr E Crystallogr Commun. 2017 Jan 1;73(Pt 1):81-84. doi: 10.1107/S2056989016019927.

Authors

Mario A Macías¹, Enrique Pandolfi², Valeria Schapiro², Gustavo P Silveira³, Guilherme D Vilela³, Leopoldo Suescun⁴

Affiliations

¹ Departamento de Química, Universidad de los Andes, Carrera 1 No 18A-12, Bogotá, Colombia.
² Departamento de Química Orgánica, Facultad de Química, Universidad de la República, Montevideo, Uruguay.
³ Departamento de Química Orgánica, Instituto de Química, Universidade Federal do Rio Grande do Sul, Porto Alegre/RS, 91501-970, Brazil.
⁴ Cryssmat-Lab/Cátedra de Física/DETEMA, Universidad de la República, Montevideo, Uruguay.

Abstract

The absolute configuration, i.e. (3aR,3'aR,7aS,7'aS), of the title compound, C₁₈H₂₆O₄, synthesized via a palladium-catalyzed homocoupling reaction, was determined on the basis of the synthetic pathway and was confirmed by X-ray diffraction. The homocoupled mol-ecule is formed by two chemically identical moieties built up from two five- and six-membered fused rings. The supra-molecular assembly is controlled mainly by C-H⋯O inter-actions that lead to the formation of hydrogen-bonded chains of mol-ecules along the [001] direction, while weak dipolar inter-actions and van der Waals forces hold the chains together in the crystal structure.

Keywords: 1,3-benzodioxolyl; absolute configuration; crystal structure; homocoupling reaction; palladium-catalyzed.