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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.


Hirshfeld surface mapped over (a) dnorm highlighting the regions of C—H⋯O hydrogen bonding and (b) dnorm highlighting the region of C—H⋯N hydrogen bonding.
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fig5: Hirshfeld surface mapped over (a) dnorm highlighting the regions of C—H⋯O hydrogen bonding and (b) dnorm highlighting the region of C—H⋯N hydrogen bonding.

Mentions: To explore the weak inter­molecular inter­actions in (I), Hirshfeld surfaces and 2D fingerprint plots were generated using Crystal Explorer 3.1 to qu­antify the inter­molecular inter­actions (McKinnon et al., 2007 ▸; Spackman & Jayatilaka, 2009 ▸). Hirshfeld surfaces are produced through the partitioning of space within a crystal where the ratio of promol­ecule to procrystal electron density is equal to 0.5, generating continuous, non-overlapping surfaces which are widely used to visualize and study the significance of weak inter­actions in the mol­ecular packing (McKinnon et al., 2007 ▸). The Hirshfeld surface of title compound was mapped over dnorm, shape index and curvedness. The dnorm surface is the normalized function of di and de (Fig. 4 ▸a), with white-, red- and blue-coloured surfaces. The white surface indicates those contacts with distances equal to the sum of the van der Waals (vdW) radii, red indicates shorter contacts (< vdW radii) and blue the longer contact (> vdW radii). The Hirshfeld surface was also mapped over electrostatic potential (Fig. 4 ▸b) using a STO-3G basis set at the Hartee–Fock level of theory (Spackman & McKinnon, 2002 ▸; McKinnon et al., 2004 ▸). In the Hirshfeld surface, a pair of inter­actions between the aromatic C—H⋯O=C atoms can be seen as the bright-red area (1) in Fig. 5 ▸a. The 2D fingerprint plot analysis of the O⋯H inter­actions revealed significant hydrogen-bonding spikes (di = 1.3, de = 0.9 Å and de = 1.9, di = 2.6 Å); Fig. 6 ▸c.


Crystal structure and Hirshfeld surface analysis of ethyl 5-phenyl ­ isoxazole-3-carboxyl ­ ate
Hirshfeld surface mapped over (a) dnorm highlighting the regions of C—H⋯O hydrogen bonding and (b) dnorm highlighting the region of C—H⋯N hydrogen bonding.
© Copyright Policy - open-access
Related In: Results  -  Collection

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getmorefigures.php?uid=PMC5382615&req=5

fig5: Hirshfeld surface mapped over (a) dnorm highlighting the regions of C—H⋯O hydrogen bonding and (b) dnorm highlighting the region of C—H⋯N hydrogen bonding.
Mentions: To explore the weak inter­molecular inter­actions in (I), Hirshfeld surfaces and 2D fingerprint plots were generated using Crystal Explorer 3.1 to qu­antify the inter­molecular inter­actions (McKinnon et al., 2007 ▸; Spackman & Jayatilaka, 2009 ▸). Hirshfeld surfaces are produced through the partitioning of space within a crystal where the ratio of promol­ecule to procrystal electron density is equal to 0.5, generating continuous, non-overlapping surfaces which are widely used to visualize and study the significance of weak inter­actions in the mol­ecular packing (McKinnon et al., 2007 ▸). The Hirshfeld surface of title compound was mapped over dnorm, shape index and curvedness. The dnorm surface is the normalized function of di and de (Fig. 4 ▸a), with white-, red- and blue-coloured surfaces. The white surface indicates those contacts with distances equal to the sum of the van der Waals (vdW) radii, red indicates shorter contacts (< vdW radii) and blue the longer contact (> vdW radii). The Hirshfeld surface was also mapped over electrostatic potential (Fig. 4 ▸b) using a STO-3G basis set at the Hartee–Fock level of theory (Spackman & McKinnon, 2002 ▸; McKinnon et al., 2004 ▸). In the Hirshfeld surface, a pair of inter­actions between the aromatic C—H⋯O=C atoms can be seen as the bright-red area (1) in Fig. 5 ▸a. The 2D fingerprint plot analysis of the O⋯H inter­actions revealed significant hydrogen-bonding spikes (di = 1.3, de = 0.9 Å and de = 1.9, di = 2.6 Å); Fig. 6 ▸c.

View Article: PubMed Central - HTML - PubMed

ABSTRACT

The title compound, C12H11NO3, is an inter&shy;mediate used in the synthesis of many drug-like mol&shy;ecules. The mol&shy;ecule is almost planar, with the phenyl ring inclined to the isoxazole ring by 0.5&#8197;(1)&deg;. 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&mdash;C&mdash;C&mdash;N torsion angle of &minus;172.86&#8197;(18)&deg;. In the crystal, mol&shy;ecules are linked via pairs of C&mdash;H&#8943;O hydrogen bonds with the same acceptor atom, forming inversion dimers with two R21(7) ring motifs. The mol&shy;ecules stack in layers lying parallel to (10-3). Analysis using Hirshfeld surface generation and two-dimensional fingerprint plots explores the distribution of weak inter&shy;molecular inter&shy;actions in the crystal structure.

No MeSH data available.