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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.


The mol­ecular structure of the title compound, showing displacement ellipsoids drawn at the 40% probability level.
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fig1: The mol­ecular structure of the title compound, showing displacement ellipsoids drawn at the 40% probability level.

Mentions: In the crystal structure of the title compound, a chalcone-thio­phene derivative, the asymmetric unit contains one crystallographically independent mol­ecule (Fig. 1 ▸). The mol­ecule is not planar: the r.m.s deviations from the mean plane of the non–H atoms range from −0.158 (3) Å for C3 to 0.1318 (15) Å for S1 and the dihedral angle between the benzene and thio­phene rings amounts to 11.4 (2)°. In addition, the plane through the amino group atoms (C7/C8/N1) is rotated by 9.7 (6)° with respect to the plane of the aromatic ring. Finally, the mol­ecule shows the E configuration about the C9—C10 bond.


Crystal structure of (2 E )-3-[4-(di ­ methyl ­ amino) ­ phen ­ yl]-1-(thio ­ phen-2-yl)prop-2-en-1-one
The mol­ecular structure of the title compound, showing displacement ellipsoids drawn at the 40% probability level.
© Copyright Policy - open-access
Related In: Results  -  Collection

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

fig1: The mol­ecular structure of the title compound, showing displacement ellipsoids drawn at the 40% probability level.
Mentions: In the crystal structure of the title compound, a chalcone-thio­phene derivative, the asymmetric unit contains one crystallographically independent mol­ecule (Fig. 1 ▸). The mol­ecule is not planar: the r.m.s deviations from the mean plane of the non–H atoms range from −0.158 (3) Å for C3 to 0.1318 (15) Å for S1 and the dihedral angle between the benzene and thio­phene rings amounts to 11.4 (2)°. In addition, the plane through the amino group atoms (C7/C8/N1) is rotated by 9.7 (6)° with respect to the plane of the aromatic ring. Finally, the mol­ecule shows the E configuration about the C9—C10 bond.

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.