16α-Hydroxyfriedelin and 3-Oxo-16-methylfriedel-16-ene as Building Blocks: Crystal Structure and Hirshfeld Surfaces Decoding Intermolecular Contacts

Author:

Corrêa Rodrigo S.12,Duarte Lucienir P.3,Silva Grácia D. F.3,de Oliveira Djalma M.4,Ellena Javier5,Doriguetto Antônio C.1

Affiliation:

1. Laboratório de Cristalografia, Instituto de Química, Universidade Federal de Alfenas (UNIFAL-MG), 37130-000 Alfenas, MG, Brazil

2. Departamento de Química, Universidade Federal de São Carlos (UFSCar), 13561-901 São Carlos, SP, Brazil

3. Departamento de Química, ICEx, Universidade Federal de Minas Gerais (UFMG), 31270-901 Belo Horizonte, MG, Brazil

4. Departamento de Química e Exatas, Universidade Estadual do Sudoeste de Bahia (UESB), 45206-190 Jequié, BA, Brazil

5. Departamento de Física e Informática, Instituto de Física de São Carlos (USP), 13560-970 São Carlos, SP, Brazil

Abstract

In this paper the importance of C–HO intermolecular hydrogen bonds and van der Waals forces in crystal packing stabilization of 16α-hydroxyfriedelin (1) and 3-oxo-16-methylfriedel-16-ene (2) is described. Compound 1 is a natural product isolated from the hexane extract of Salacia elliptica branches, whereas compound 2 is obtained from compound 1 after dehydration accompanied by methyl migration of C-17 to C-16. The single-crystal X-ray diffraction experiments for 1 and 2 were carried out at 150 K, and the crystallographic study demonstrated that these compounds crystallize in noncentrosymmetric space groups, with 1 showing an orthorhombic P212121 space group and 2 a monoclinic P21 one. Compounds 1 and 2 are composed of five fused six-membered rings presenting a chair conformation, except for the central ring of 2, which adopts a half-chair conformation. In addition, the intra- and intermolecular parameters were studied using CCDC MOGUL analyses and Hirshfeld surfaces.

Publisher

Hindawi Limited

Subject

Computer Networks and Communications,Hardware and Architecture,Software

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