Crystal structure of (3,5-di-chloro-2-hy-droxy-phen-yl){1-[(naphthalen-1-yl)carbon-yl]-1H-pyrazol-4-yl}methanone.

Yoshinobu Ishikawa,Yuya Motohashi

doi:10.1107/s1600536814024684

Yoshinobu Ishikawa, Yuya Motohashi

Open Access

https://doi.org/10.1107/s1600536814024684

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Abstract

The title compound, C21H12Cl2N2O3, is a 1,4-diaroyl pyrazole derivative and has three aromatic rings. The dihedral angles between the naphthalene ring system and the pyrazole ring, the pyrazole and phenyl rings and the naphthalene ring system and the phenyl ring are 49.44 (13), 49.87 (16) and 0.58 (11)°, respectively. The phenolic proton forms an intra-molecular O-H⋯O hydrogen bond with an adjacent carbonyl O atom. In the crystal, the mol-ecules are linked through stacking inter-actions between the pyrazole rings [centroid-centroid distances = 3.546 (3)] and between the naphthalene ring system and the phenyl ring [centroid-centroid distances = 3.609 (4) Å] along the a-axis direction. The mol-ecules are further connected through C-H⋯O hydrogen bonds, forming inversion dimers.

Highlights

The title compound, C21H12Cl2N2O3, is a 1,4-diaroyl pyrazole derivative and has three aromatic rings
The dihedral angles between the naphthalene ring system and the pyrazole ring, the pyrazole and phenyl rings and the naphthalene ring system and the phenyl ring are 49.44 (13), 49.87 (16) and 0.58 (11), respectively
3-Formylchromones are used as diverse building blocks (Ali et al, 2013), and their Schiff base derivatives have attracted much attention in medicinal chemistry (Nawrot-Modranka et al, 2006; Khan et al, 2009; Wang et al, 2008; Tu et al, 2013; Gaspar et al, 2014)

Summary

Chemical context

3-Formylchromones are used as diverse building blocks (Ali et al, 2013), and their Schiff base derivatives have attracted much attention in medicinal chemistry (Nawrot-Modranka et al, 2006; Khan et al, 2009; Wang et al, 2008; Tu et al, 2013; Gaspar et al, 2014). We have recently reported the crystal structures of such Schiff base compounds (Ishikawa & Watanabe, 2014a,b,c,d), which were prepared from condensation reactions of 3-formylchromones with arylhydrazides. Crystallographic analysis revealed that the structure of the orange crystals obtained from crystallization of the white solid prepared from the condensation reaction of 6,8dibromo-3-formylchromone (Ishikawa, 2014) with 1-naphthohydrazide is a 1,4-diaroyl pyrazole (Ishikawa & Motohashi, 2014)

Structural commentary

Supramolecular features

Database survey

Synthesis and crystallization

Refinement