(2Z)-3-(4-Fluoroanilino)-1-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)but-2-en-1-one

Abdullah M Asiri,Hassan M Faidallah,Edward R T Tiekink,Seik Weng Ng

doi:10.1107/s1600536812006514

Abdullah M Asiri, Hassan M Faidallah + Show 2 more

Open Access

https://doi.org/10.1107/s1600536812006514

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Abstract

The central carbonyl group in the title compound, C20H18FN3O2, forms amine–hydroxy N—H⋯O and hydroxy–hydroxy O—H⋯O hydrogen bonds, leading to two S(6) rings. The N-bound phenyl ring is coplanar with the five-membered ring to which it is attached [dihedral angle = 6.27 (10)°], but an overall twist in the molecule is evident, the dihedral angle between the terminal phenyl and benzene rings being 27.30 (10)°. Molecules aggregate into a three-dimensional architecture via C—H⋯F, C—H⋯O and C—H⋯π interactions.

Highlights

The central carbonyl group in the title compound, C20H18FN3O2, forms amine–hydroxy N—H O and hydroxy–hydroxy O—H O hydrogen bonds, leading to two
H atoms treated by a mixture of independent and constrained refinement max = 0.25 e Å3
The N-bound phenyl ring is coplanar with the fivemembered ring to which it is attached [dihedral angle =

Summary

Agilent SuperNova Dual diffractometer with an Atlas detector

H atoms treated by a mixture of independent and constrained refinement max = 0.25 e Å3. R factor = 0.055; wR factor = 0.123; data-to-parameter ratio = 15.8. The central carbonyl group in the title compound, C20H18FN3O2, forms amine–hydroxy N—H O and hydroxy–hydroxy O—H O hydrogen bonds, leading to two. The N-bound phenyl ring is coplanar with the fivemembered ring to which it is attached [dihedral angle =. 6.27 (10) ], but an overall twist in the molecule is evident, the dihedral angle between the terminal phenyl and benzene rings being 27.30 (10). Molecules aggregate into a three-dimensional architecture via C—H F, C—H O and C—H interactions. Cg1 is the centroid of the C15–C20 benzene ring. Symmetry codes: (i) x; y þ 32; z 12; (ii) x; y þ 12; z þ 32; (iii) x; y þ 12; z þ 12. Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010)

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Crystal data

Mirror monochromator