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Influence of hydrogen bonds on the molecular structure and conformations of two (C30H48O2) pentacyclic triterpene isomers

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Abstract

The structural study of two (C30H48O2) pentacyclic triterpene (PCTT) isomers is presented. These terpenes, known as 30-hydroxy-lup-20(29)-en-3-one (1) and (11α)-11-hydroxy-lup-20(29)-en-3-one (2), were isolated from Maytenus imbricata Mart. Ex Reissek (Celastraceae). The molecular structure of 1 and 2 differs in the position of the hydroxyl group. Both compounds crystallize in non-centrosymmetric space groups with two molecules in the asymmetric unit. The crystal structure of 1 shows a triclinic P1 space group (a = 9.5518(1) Å, b = 9.7083(1) Å, c = 14.4696(2) Å, α = 93.832(1)°, β = 102.833(1)°, and γ = 103.307(1)°), while compound 2 crystallizes in a monoclinic P21 one (a = 13.4439(16) Å, b = 14.4463(14) Å, c = 13.5224(9) Å and β = 99.703(8)°). The two molecules independent by symmetry of 1 differ slightly due to the presence of static disorder in oxygen atoms. In addition, the intermolecular geometries of 1 and 2 were analysed, and in each isomer the crystal packing is stabilized by O-H…O intermolecular hydrogen bonds and van der Waals forces.

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Authors and Affiliations

  1. Instituto de Química, Universidade Federal de Alfenas — UNIFAL-MG, 37130-000, Alfenas, MG, Brazil

    R. S. Corrêa & A. C. Doriguetto

  2. Departamento de Química, ICEX, Universidade Federal de Minas Gerais — UFMG, 31270-901, Belo Horizonte, MG, Brazil

    S. R. Souza e Silva, L. P. Duarte & G. D. F. Silva

  3. Departamento de Química, Universidade Federal de Viçosa, 36570-000, Viçosa, MG, Brazil

    L. C. A. Barbosa

  4. Departamento de Física e Informática, Instituto de Física de São Carlos — USP, 13560-970, São Carlos, SP, Brazil

    J. Ellena

Authors
  1. R. S. Corrêa
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  2. S. R. Souza e Silva
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  3. L. P. Duarte
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  4. G. D. F. Silva
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  5. L. C. A. Barbosa
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  6. J. Ellena
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  7. A. C. Doriguetto
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Correspondence to A. C. Doriguetto.

Additional information

Original Russian Text Copyright © 2012 by R. S. Corrêa, S. R. Souza e Silva, L. P. Duarte, G. D. F. Silva, L. C. A. Barbosa, J. Ellena, and A. C. Doriguetto

The text was submitted by the authors in English. Zhurnal Strukturnoi Khimii, Vol. 53, No. 1, pp. 160–166, January–February, 2012.

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Corrêa, R.S., Souza e Silva, S.R., Duarte, L.P. et al. Influence of hydrogen bonds on the molecular structure and conformations of two (C30H48O2) pentacyclic triterpene isomers. J Struct Chem 53, 156–163 (2012). https://doi.org/10.1134/S0022476612010210

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