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Crystal structure and Hirshfeld surface analysis of ethyl 5-phenyl ­ isoxazole-3-carboxyl ­ ate

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ABSTRACT

The title compound, C12H11NO3, is an inter­mediate used in the synthesis of many drug-like mol­ecules. The mol­ecule is almost planar, with the phenyl ring inclined to the isoxazole ring by 0.5 (1)°. The ester moiety has an extended conformation and is almost in the same plane with respect to the isoxazole ring, as indicated by the O—C—C—N torsion angle of −172.86 (18)°. In the crystal, mol­ecules are linked via pairs of C—H⋯O hydrogen bonds with the same acceptor atom, forming inversion dimers with two R21(7) ring motifs. The mol­ecules stack in layers lying parallel to (10-3). Analysis using Hirshfeld surface generation and two-dimensional fingerprint plots explores the distribution of weak inter­molecular inter­actions in the crystal structure.

No MeSH data available.


The mol­ecular structure of compound (I), with the atom labelling and displacement ellipsoid drawn at the 50% probability level.
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fig1: The mol­ecular structure of compound (I), with the atom labelling and displacement ellipsoid drawn at the 50% probability level.

Mentions: The mol­ecular structure of the title compound, (I), is illus­trated in Fig. 1 ▸. The mol­ecule consists of three almost flat units: the phenyl ring, the isoxazole ring and the ester. The phenyl (C1–C6) and isoxazole (O1/N1/C7–C9) rings are almost coplanar, as indicated by the torsion angle C5—C6—C7—O1 = 0.1 (3)°. The ester unit has an extended conformation and is almost in the same plane as the isoxazole ring, as indicated by the torsion angle O2—C10—C9—N1 = −172.86 (18)°.


Crystal structure and Hirshfeld surface analysis of ethyl 5-phenyl ­ isoxazole-3-carboxyl ­ ate
The mol­ecular structure of compound (I), with the atom labelling and displacement ellipsoid drawn at the 50% probability level.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC5382615&req=5

fig1: The mol­ecular structure of compound (I), with the atom labelling and displacement ellipsoid drawn at the 50% probability level.
Mentions: The mol­ecular structure of the title compound, (I), is illus­trated in Fig. 1 ▸. The mol­ecule consists of three almost flat units: the phenyl ring, the isoxazole ring and the ester. The phenyl (C1–C6) and isoxazole (O1/N1/C7–C9) rings are almost coplanar, as indicated by the torsion angle C5—C6—C7—O1 = 0.1 (3)°. The ester unit has an extended conformation and is almost in the same plane as the isoxazole ring, as indicated by the torsion angle O2—C10—C9—N1 = −172.86 (18)°.

View Article: PubMed Central - HTML - PubMed

ABSTRACT

The title compound, C12H11NO3, is an inter­mediate used in the synthesis of many drug-like mol­ecules. The mol­ecule is almost planar, with the phenyl ring inclined to the isoxazole ring by 0.5 (1)°. The ester moiety has an extended conformation and is almost in the same plane with respect to the isoxazole ring, as indicated by the O—C—C—N torsion angle of −172.86 (18)°. In the crystal, mol­ecules are linked via pairs of C—H⋯O hydrogen bonds with the same acceptor atom, forming inversion dimers with two R21(7) ring motifs. The mol­ecules stack in layers lying parallel to (10-3). Analysis using Hirshfeld surface generation and two-dimensional fingerprint plots explores the distribution of weak inter­molecular inter­actions in the crystal structure.

No MeSH data available.