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Crystal structure of the chalcone (E)-3-(furan-2-yl)-1-phenylprop-2-en-1-one.

Vázquez-Vuelvas OF, Enríquez-Figueroa RA, García-Ortega H, Flores-Alamo M, Pineda-Contreras A - Acta Crystallogr E Crystallogr Commun (2015)

Bottom Line: The title chalcone derivative, C13H10O2, adopts an E conformation about the C=C double bond.The mol-ecule is composed of a furanyl and a phenyl ring, bridged by an α,β-unsaturated carbonyl system, which are inclined to one another by 24.07 (7)°.In the crystal, mol-ecules are connected by weak C-H⋯O hydrogen bonds involving the carbonyl O atom acting as a trifurcated acceptor and C-H⋯π inter-actions, forming ribbons extending along the c-axis direction.

View Article: PubMed Central - HTML - PubMed

Affiliation: Facultad de Ciencias Químicas, Universidad de Colima, Km 9 Carr. Colima-Coquimatlán s/n, Coquimatlán, Colima 28400, Mexico.

ABSTRACT
The title chalcone derivative, C13H10O2, adopts an E conformation about the C=C double bond. The mol-ecule is composed of a furanyl and a phenyl ring, bridged by an α,β-unsaturated carbonyl system, which are inclined to one another by 24.07 (7)°. In the crystal, mol-ecules are connected by weak C-H⋯O hydrogen bonds involving the carbonyl O atom acting as a trifurcated acceptor and C-H⋯π inter-actions, forming ribbons extending along the c-axis direction.

No MeSH data available.


Related in: MedlinePlus

The mol­ecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.
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fig1: The mol­ecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.

Mentions: The symmetry-independent mol­ecule adopts an E conformation corresponding to an α,β-unsaturated non-planar structure, which bridges the pair of aromatic groups (Fig. 1 ▶). The two main planar groups, the furanyl and the phenyl rings, form a dihedral angle of 24.07 (7)°. In this context, the mol­ecular structure can be considered, for descriptive purposes, as two fragments basically described by the furanyl acryloyl and the benzoyl moieties. The benzoyl group shows a non-planar structure and presents rotation when observing the C2—C1—C7—O2 torsion angle of 19.4 (2)°, denoting a marked deviation from planarity at the C1—C7 bond, a single bond with rotational freedom. This deviation from planarity has also been reported previously in the crystal structure of an (E)-3-(4-hy­droxy­phen­yl)-1-(4-meth­oxy­phen­yl)-prop-2-en-1-one derivative, when observing the analogous reported inter­planar angle shown in the respectively 4-meth­oxy­benzoyl moiety (Qiu et al., 2006 ▶). In the same manner, the furanyl acryloyl entity presents a quasi-planar structure indicated by the two small torsion angles O2—C7—C8—C9 [−5.4 (2)°] and C7—C8—C9—C10 [−176.31 (13)°], similar to the structure of the di­furanyl chalcone derivative (E)-1,3-di(2-fur­yl)-2-propen-1-one (Ocak Iskeleli et al., 2005b ▶). On the other hand, the mol­ecule inter­atomic linkage coincides with similar reported structures, specifically in the α,β-unsaturated entity of the title crystal (Harrison et al., 2006 ▶; Ocak Iskeleli et al., 2005a ▶,b ▶). As a result, the inter­atomic distances are in agreement with the conjugative nature, which is additionally supported by other described types of different weak inter­actions (vide infra) and also define the characteristic quasi-planar structure of chalcone derivatives.


Crystal structure of the chalcone (E)-3-(furan-2-yl)-1-phenylprop-2-en-1-one.

Vázquez-Vuelvas OF, Enríquez-Figueroa RA, García-Ortega H, Flores-Alamo M, Pineda-Contreras A - Acta Crystallogr E Crystallogr Commun (2015)

The mol­ecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4384596&req=5

fig1: The mol­ecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.
Mentions: The symmetry-independent mol­ecule adopts an E conformation corresponding to an α,β-unsaturated non-planar structure, which bridges the pair of aromatic groups (Fig. 1 ▶). The two main planar groups, the furanyl and the phenyl rings, form a dihedral angle of 24.07 (7)°. In this context, the mol­ecular structure can be considered, for descriptive purposes, as two fragments basically described by the furanyl acryloyl and the benzoyl moieties. The benzoyl group shows a non-planar structure and presents rotation when observing the C2—C1—C7—O2 torsion angle of 19.4 (2)°, denoting a marked deviation from planarity at the C1—C7 bond, a single bond with rotational freedom. This deviation from planarity has also been reported previously in the crystal structure of an (E)-3-(4-hy­droxy­phen­yl)-1-(4-meth­oxy­phen­yl)-prop-2-en-1-one derivative, when observing the analogous reported inter­planar angle shown in the respectively 4-meth­oxy­benzoyl moiety (Qiu et al., 2006 ▶). In the same manner, the furanyl acryloyl entity presents a quasi-planar structure indicated by the two small torsion angles O2—C7—C8—C9 [−5.4 (2)°] and C7—C8—C9—C10 [−176.31 (13)°], similar to the structure of the di­furanyl chalcone derivative (E)-1,3-di(2-fur­yl)-2-propen-1-one (Ocak Iskeleli et al., 2005b ▶). On the other hand, the mol­ecule inter­atomic linkage coincides with similar reported structures, specifically in the α,β-unsaturated entity of the title crystal (Harrison et al., 2006 ▶; Ocak Iskeleli et al., 2005a ▶,b ▶). As a result, the inter­atomic distances are in agreement with the conjugative nature, which is additionally supported by other described types of different weak inter­actions (vide infra) and also define the characteristic quasi-planar structure of chalcone derivatives.

Bottom Line: The title chalcone derivative, C13H10O2, adopts an E conformation about the C=C double bond.The mol-ecule is composed of a furanyl and a phenyl ring, bridged by an α,β-unsaturated carbonyl system, which are inclined to one another by 24.07 (7)°.In the crystal, mol-ecules are connected by weak C-H⋯O hydrogen bonds involving the carbonyl O atom acting as a trifurcated acceptor and C-H⋯π inter-actions, forming ribbons extending along the c-axis direction.

View Article: PubMed Central - HTML - PubMed

Affiliation: Facultad de Ciencias Químicas, Universidad de Colima, Km 9 Carr. Colima-Coquimatlán s/n, Coquimatlán, Colima 28400, Mexico.

ABSTRACT
The title chalcone derivative, C13H10O2, adopts an E conformation about the C=C double bond. The mol-ecule is composed of a furanyl and a phenyl ring, bridged by an α,β-unsaturated carbonyl system, which are inclined to one another by 24.07 (7)°. In the crystal, mol-ecules are connected by weak C-H⋯O hydrogen bonds involving the carbonyl O atom acting as a trifurcated acceptor and C-H⋯π inter-actions, forming ribbons extending along the c-axis direction.

No MeSH data available.


Related in: MedlinePlus