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

What is it about?

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)°. In the crystal, mol­ecules are linked by C—H⋯O and weak C—H⋯S inter­actions along [100], forming R22(8) rings, and by weak C—H⋯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⋯π inter­actions, as indicated by the Hirshfeld surface analysis. The most important contributions for the crystal structure are the H⋯H (46.50%) and H⋯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⋯O, (PRO245)C—H⋯Cg(thio­phene ring) and (AGR287)C—H⋯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).

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