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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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A crystal packing view of the title compound. Intra­molecular O—H⋯O and inter­molecular C—H⋯O hydrogen bonds are represented by black and red dashed lines, respectively.
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fig3: A crystal packing view of the title compound. Intra­molecular O—H⋯O and inter­molecular C—H⋯O hydrogen bonds are represented by black and red dashed lines, respectively.

Mentions: The mol­ecules are linked along the a-axis through stacking inter­actions between inversion-related pyrazole rings, and between the naphthalene ring system and the phenyl ring of an inversion-related molecule [centroid–centroid distances = 3.546 (3) and 3.609 (4) Å, respectively; symmetry code: –x + 1, –y + 1, –z]. The mol­ecules are further connected through inter­molecular C—H⋯O hydrogen bonds (Table 1 ▶), forming inversion dimers, as shown in Fig. 3 ▶. Type I halogen⋯halogen contacts between the chlorine atoms, which is seen in the crystal structure of the starting material, 6,8-di­chloro-3-formyl­chromone (Ishikawa & Motohashi, 2013 ▶), are not observed.


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)

A crystal packing view of the title compound. Intra­molecular O—H⋯O and inter­molecular C—H⋯O hydrogen bonds are represented by black and red dashed lines, respectively.
© Copyright Policy - open-access
Related In: Results  -  Collection

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

fig3: A crystal packing view of the title compound. Intra­molecular O—H⋯O and inter­molecular C—H⋯O hydrogen bonds are represented by black and red dashed lines, respectively.
Mentions: The mol­ecules are linked along the a-axis through stacking inter­actions between inversion-related pyrazole rings, and between the naphthalene ring system and the phenyl ring of an inversion-related molecule [centroid–centroid distances = 3.546 (3) and 3.609 (4) Å, respectively; symmetry code: –x + 1, –y + 1, –z]. The mol­ecules are further connected through inter­molecular C—H⋯O hydrogen bonds (Table 1 ▶), forming inversion dimers, as shown in Fig. 3 ▶. Type I halogen⋯halogen contacts between the chlorine atoms, which is seen in the crystal structure of the starting material, 6,8-di­chloro-3-formyl­chromone (Ishikawa & Motohashi, 2013 ▶), are not observed.

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