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Crystal structure of (2 E )-3-[4-(di ­ methyl ­ amino) ­ phen ­ yl]-1-(thio ­ phen-2-yl)prop-2-en-1-one

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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)°. 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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Section of the crystal structures of (a) the title compound viewed along [100], and (b) the 3-(4-methyl­phen­yl)-1-(3-thien­yl)-2-propen-1-one compound (Li & Su, 1993 ▸) viewed along [001], showing the herringbone motif.
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fig9: Section of the crystal structures of (a) the title compound viewed along [100], and (b) the 3-(4-methyl­phen­yl)-1-(3-thien­yl)-2-propen-1-one compound (Li & Su, 1993 ▸) viewed along [001], showing the herringbone motif.

Mentions: In addition, a lock-and-key supra­molecular analysis between the neuraminidase enzyme, whose inhibition is believed to be a key point to block the influenza viral infection (Kinger et al., 2012 ▸), and the title compound was performed. The semi-empirical equilibrium energy of the title compound was obtained using the PM6 Hamiltonian and the experimental bond lengths were conserved. The calculated parameters were: heat of formation = 139.28 kJ mol−1, gradient normal = 0.62031, HOMO = −8.96 eV, LUMO = −0.866 eV and energy gap = 7.421 eV (Stewart, 2013 ▸). The rigid mol­ecular docking was carried out with the GOLD software (Jones et al., 1997 ▸) using the ChemPLP score function (Chen, 2015 ▸). The chalcone thio­phene derivative and the active site of the neuraminidase match (Fig. 7 ▸) and the structure–activity relationship can be assumed by the following observed inter­molecular inter­actions (H⋯A distance values given in Å): (ASN263)N—H⋯O1 (d = 1.796), (PRO245)C—H⋯Cg(thio­phene ring) (d = 2.829) and (AGR287)C—H⋯N1 (d = 2.620) (Fig. 8 ▸). More details about the in silico evaluation, with additional references, can be found in the Supporting Information. For the inter­molecular inter­actions, it is important to report that the H⋯Cg(thio­phene ring) contact is observed in the structure inter­pretation, by the centrosymmetric dimeric arrangement of the mol­ecules (Figs. 3 ▸ and 9 ▸), in the Hirshfeld surface analysis (Fig. 5 ▸) and in the mol­ecular docking evaluation (Fig. 8 ▸).


Crystal structure of (2 E )-3-[4-(di ­ methyl ­ amino) ­ phen ­ yl]-1-(thio ­ phen-2-yl)prop-2-en-1-one
Section of the crystal structures of (a) the title compound viewed along [100], and (b) the 3-(4-methyl­phen­yl)-1-(3-thien­yl)-2-propen-1-one compound (Li & Su, 1993 ▸) viewed along [001], showing the herringbone motif.
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fig9: Section of the crystal structures of (a) the title compound viewed along [100], and (b) the 3-(4-methyl­phen­yl)-1-(3-thien­yl)-2-propen-1-one compound (Li & Su, 1993 ▸) viewed along [001], showing the herringbone motif.
Mentions: In addition, a lock-and-key supra­molecular analysis between the neuraminidase enzyme, whose inhibition is believed to be a key point to block the influenza viral infection (Kinger et al., 2012 ▸), and the title compound was performed. The semi-empirical equilibrium energy of the title compound was obtained using the PM6 Hamiltonian and the experimental bond lengths were conserved. The calculated parameters were: heat of formation = 139.28 kJ mol−1, gradient normal = 0.62031, HOMO = −8.96 eV, LUMO = −0.866 eV and energy gap = 7.421 eV (Stewart, 2013 ▸). The rigid mol­ecular docking was carried out with the GOLD software (Jones et al., 1997 ▸) using the ChemPLP score function (Chen, 2015 ▸). The chalcone thio­phene derivative and the active site of the neuraminidase match (Fig. 7 ▸) and the structure–activity relationship can be assumed by the following observed inter­molecular inter­actions (H⋯A distance values given in Å): (ASN263)N—H⋯O1 (d = 1.796), (PRO245)C—H⋯Cg(thio­phene ring) (d = 2.829) and (AGR287)C—H⋯N1 (d = 2.620) (Fig. 8 ▸). More details about the in silico evaluation, with additional references, can be found in the Supporting Information. For the inter­molecular inter­actions, it is important to report that the H⋯Cg(thio­phene ring) contact is observed in the structure inter­pretation, by the centrosymmetric dimeric arrangement of the mol­ecules (Figs. 3 ▸ and 9 ▸), in the Hirshfeld surface analysis (Fig. 5 ▸) and in the mol­ecular docking evaluation (Fig. 8 ▸).

View Article: PubMed Central - HTML - PubMed

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)°. 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).

No MeSH data available.