Crystal structure of (2E)-3-[4-(dimethylamino)phenyl]-1-(thiophen-2-yl)prop-2-en-1-one

Author(s)

de Oliveira, Gabriela Porto ; Bresolin, Leandro ; Flores, Darlene Correia ; de Farias, Renan Lira ; de Oliveira, Adriano Bof

• Document type: Journal article
• Source: ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS; v. 73, p. 10-pg., 2017-04-01.

Abstract

The equimolar reaction between 4-(dimethylamino)benzaldehyde and 2-acetylthiophene in basic ethanolic solution yields the title compound, C15H15NOS, whose molecular structure matches the asymmetric unit. The molecule is not planar, the dihedral angle between the aromatic and the thiophene rings being 11.4 (2)degrees. In the crystal, molecules are linked by C-H center dot center dot center dot O and weak C-H center dot center dot center dot S interactions along [100], forming R-2(2)(8) rings, and by weak C-H center dot center dot center dot O interactions along [010], forming chains with a C(6) graph-set motif. In addition, molecules are connected into centrosymmetric dimers by weak C-H center dot center dot center dot pi interactions, as indicated by the Hirshfeld surface analysis. The most important contributions for the crystal structure are the H center dot center dot center dot H (46.50%) and H center dot center dot center dot C (23.40%) interactions. The crystal packing resembles a herringbone arrangement when viewed along [100]. A molecular docking calculation of the title compound with the neuraminidase enzyme was carried out. The enzyme shows (ASN263)N-H center dot center dot center dot O, (PRO245)C-H center dot center dot center dot Cg(thiophene ring) and (AGR287)C-H center dot center dot center dot N intermolecular interactions with the title compound. The crystal structure was refined as a two-component twin with a fractional contribution to the minor domain of 0.0181 (8). (AU)

• FAPESP's process: 15/12098-0 - Dinitrosyl complexes containing thiol and/or thiosemicarbazone : synthesis, characterization and treatment against cancer
• Grantee: José Clayston Melo Pereira
• Support Opportunities: Regular Research Grants