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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.


Graphical representation of the weak inter­molecular C—H⋯O, C—H⋯S and H⋯H inter­actions (dashed lines) in the crystal structure of the title compound. [Symmetry codes: (i) x + 1, y, z; (ii) −x − , y − , −z + .]
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fig2: Graphical representation of the weak inter­molecular C—H⋯O, C—H⋯S and H⋯H inter­actions (dashed lines) in the crystal structure of the title compound. [Symmetry codes: (i) x + 1, y, z; (ii) −x − , y − , −z + .]

Mentions: In the crystal, the mol­ecules are connected by very weak C13—H13⋯O1i and C14—H14⋯S1i hydrogen-bonding inter­actions (see Table 1 ▸ for symmetry codes), forming rings with an R22(8) graph-set motif. The R22(8) rings are the subunits of the periodic arrangement along [100] and one very weak H7⋯H2i contact is also observed [H⋯H = 2.26 Å]. The mol­ecular units are also linked by very weak C15—H15⋯O1ii links into chains along [010] with a C(6) graph-set motif (Fig. 2 ▸; Table 1 ▸). Additionally, the mol­ecules are connected into centrosymmetric dimers by very weak C—H⋯π inter­actions involving the thio­phene ring (Fig. 3 ▸; Table 1 ▸). The inter­molecular contacts are slightly longer than the sum of the van der Waals radii for the respective atoms (Bondi, 1964 ▸; Rowland & Taylor, 1996 ▸) and suggest weak inter­actions only.


Crystal structure of (2 E )-3-[4-(di ­ methyl ­ amino) ­ phen ­ yl]-1-(thio ­ phen-2-yl)prop-2-en-1-one
Graphical representation of the weak inter­molecular C—H⋯O, C—H⋯S and H⋯H inter­actions (dashed lines) in the crystal structure of the title compound. [Symmetry codes: (i) x + 1, y, z; (ii) −x − , y − , −z + .]
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC5382602&req=5

fig2: Graphical representation of the weak inter­molecular C—H⋯O, C—H⋯S and H⋯H inter­actions (dashed lines) in the crystal structure of the title compound. [Symmetry codes: (i) x + 1, y, z; (ii) −x − , y − , −z + .]
Mentions: In the crystal, the mol­ecules are connected by very weak C13—H13⋯O1i and C14—H14⋯S1i hydrogen-bonding inter­actions (see Table 1 ▸ for symmetry codes), forming rings with an R22(8) graph-set motif. The R22(8) rings are the subunits of the periodic arrangement along [100] and one very weak H7⋯H2i contact is also observed [H⋯H = 2.26 Å]. The mol­ecular units are also linked by very weak C15—H15⋯O1ii links into chains along [010] with a C(6) graph-set motif (Fig. 2 ▸; Table 1 ▸). Additionally, the mol­ecules are connected into centrosymmetric dimers by very weak C—H⋯π inter­actions involving the thio­phene ring (Fig. 3 ▸; Table 1 ▸). The inter­molecular contacts are slightly longer than the sum of the van der Waals radii for the respective atoms (Bondi, 1964 ▸; Rowland & Taylor, 1996 ▸) and suggest weak inter­actions only.

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.