ss-NMR and single-crystal X-ray diffraction in the elucidation of a new polymorph of bischalcone (1E,4E)-1,5-bis(4-fluorophenyl)penta-1,4-dien-3-one.
Acta Crystallogr C Struct Chem
; 75(Pt 6): 694-701, 2019 Jun 01.
Article
em En
| MEDLINE
| ID: mdl-31166921
We report a new polymorph of (1E,4E)-1,5-bis(4-fluorophenyl)penta-1,4-dien-3-one, C17H12F2O. Contrary to the precedent literature polymorph with Z' = 3, our polymorph has one half molecule in the asymmetric unit disordered over two 50% occupancy sites. Each site corresponds to one conformation around the single bond vicinal to the carbonyl group (so-called anti or syn). The other half of the bischalcone is generated by twofold rotation symmetry, giving rise to two half-occupied and overlapping molecules presenting both anti and syn conformations in their open chain. Such a disorder allows for distinct patterns of intermolecular C-H...O contacts involving the carbonyl and anti-oriented ß-C-H groups, which is reflected in three 13C NMR chemical shifts for the carbonyl C atom. Here, we have also assessed the cytotoxicity of three symmetric bischalcones through their in vitro antitumour potential against three cancer cell lines. Cytotoxicity assays revealed that this biological property increases as halogen electronegativity increases.
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01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
Acta Crystallogr C Struct Chem
Ano de publicação:
2019
Tipo de documento:
Article
País de afiliação:
Brasil
País de publicação:
Reino Unido