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

Ishikawa Y, Motohashi Y - Acta Crystallogr Sect E Struct Rep Online (2014)

Bottom Line: 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.

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Affiliation: School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan.

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.

No MeSH data available.


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Reaction scheme for the title compound.
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fig1: Reaction scheme for the title compound.

Mentions: The reaction of 6,8-di­chloro-3-formyl­chromone (Ishikawa & Motohashi, 2013 ▶) with 1-naphtho­ylhydrazide in benzene gave yellow solids, and orange crystals were obtained from an ethyl acetate/acetone solution of the yellow solids (Fig. 1 ▶). The crystallographic analysis revealed that the structure of the orange crystals is a 1,4-diaroyl pyrazole, as shown in Fig. 2 ▶, which should be thermodynamically more stable than that of the yellow solids. 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 intra­molecular O–H⋯O hydrogen bond with the adjacent carbonyl O2 atom. The conformation of the title compound is almost identical to that of our previously reported 1,4-diaroyl pyrazole derivative (Ishikawa & Motohashi, 2014 ▶).


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

Ishikawa Y, Motohashi Y - Acta Crystallogr Sect E Struct Rep Online (2014)

Reaction scheme for the title compound.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4257447&req=5

fig1: Reaction scheme for the title compound.
Mentions: The reaction of 6,8-di­chloro-3-formyl­chromone (Ishikawa & Motohashi, 2013 ▶) with 1-naphtho­ylhydrazide in benzene gave yellow solids, and orange crystals were obtained from an ethyl acetate/acetone solution of the yellow solids (Fig. 1 ▶). The crystallographic analysis revealed that the structure of the orange crystals is a 1,4-diaroyl pyrazole, as shown in Fig. 2 ▶, which should be thermodynamically more stable than that of the yellow solids. 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 intra­molecular O–H⋯O hydrogen bond with the adjacent carbonyl O2 atom. The conformation of the title compound is almost identical to that of our previously reported 1,4-diaroyl pyrazole derivative (Ishikawa & Motohashi, 2014 ▶).

Bottom Line: 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.

View Article: PubMed Central - HTML - PubMed

Affiliation: School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan.

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.

No MeSH data available.


Related in: MedlinePlus