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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).

No MeSH data available.


A graphical representation of the Hirshfeld surface (dnorm) for the title compound. The surface is drawn with transparency and all atoms are labelled. The surface regions with strongest inter­molecular inter­actions for atoms H2, H15 and O1 are shown in magenta.
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fig4: A graphical representation of the Hirshfeld surface (dnorm) for the title compound. The surface is drawn with transparency and all atoms are labelled. The surface regions with strongest inter­molecular inter­actions for atoms H2, H15 and O1 are shown in magenta.

Mentions: The Hirshfeld surface analysis (Hirshfeld, 1977 ▸) of the crystal structure suggests that the contribution of the H⋯H inter­molecular inter­actions to the crystal packing amounts to 46.50% and the contribution of the H⋯C inter­actions amounts to 23.40%. Other important inter­molecular contacts for the cohesion of the structure are (values given in %): H⋯O = 10.80 and H⋯S = 10.00. Graphical representations of the Hirshfeld surface with transparency and labelled atoms (Figs. 4 ▸ and 5 ▸) indicate, in a magenta colour, the locations of the strongest inter­molecular contacts, e.g. the H2, H7, H13, H15 and O1 atoms. The C—H⋯π inter­action is also well represented in the Hirshfeld surface (for details, compare Figs. 3 ▸ and 5 ▸). The H⋯H, H⋯C, H⋯O and H⋯S contributions to the crystal packing are shown as a Hirshfeld surface two-dimensional fingerprint plot with cyan dots. The de (y axis) and di (x axis) values are the closest external and inter­nal distances (values given in Å) from given points on the Hirshfeld surface contacts (Fig. 6 ▸; Wolff et al., 2012 ▸).


Crystal structure of (2 E )-3-[4-(di ­ methyl ­ amino) ­ phen ­ yl]-1-(thio ­ phen-2-yl)prop-2-en-1-one
A graphical representation of the Hirshfeld surface (dnorm) for the title compound. The surface is drawn with transparency and all atoms are labelled. The surface regions with strongest inter­molecular inter­actions for atoms H2, H15 and O1 are shown in magenta.
© Copyright Policy - open-access
Related In: Results  -  Collection

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fig4: A graphical representation of the Hirshfeld surface (dnorm) for the title compound. The surface is drawn with transparency and all atoms are labelled. The surface regions with strongest inter­molecular inter­actions for atoms H2, H15 and O1 are shown in magenta.
Mentions: The Hirshfeld surface analysis (Hirshfeld, 1977 ▸) of the crystal structure suggests that the contribution of the H⋯H inter­molecular inter­actions to the crystal packing amounts to 46.50% and the contribution of the H⋯C inter­actions amounts to 23.40%. Other important inter­molecular contacts for the cohesion of the structure are (values given in %): H⋯O = 10.80 and H⋯S = 10.00. Graphical representations of the Hirshfeld surface with transparency and labelled atoms (Figs. 4 ▸ and 5 ▸) indicate, in a magenta colour, the locations of the strongest inter­molecular contacts, e.g. the H2, H7, H13, H15 and O1 atoms. The C—H⋯π inter­action is also well represented in the Hirshfeld surface (for details, compare Figs. 3 ▸ and 5 ▸). The H⋯H, H⋯C, H⋯O and H⋯S contributions to the crystal packing are shown as a Hirshfeld surface two-dimensional fingerprint plot with cyan dots. The de (y axis) and di (x axis) values are the closest external and inter­nal distances (values given in Å) from given points on the Hirshfeld surface contacts (Fig. 6 ▸; Wolff et al., 2012 ▸).

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.