Crystal structure of (3,5-dichloro-2-hydroxyphenyl){1-[(naphthalen-1-yl)carbonyl]-1H-pyrazol-4-yl}methanone
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 (...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2014-12-01
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| Series: | Acta Crystallographica Section E |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S1600536814024684 |
| _version_ | 1818488263581630464 |
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| author | Yoshinobu Ishikawa Yuya Motohashi |
| author_facet | Yoshinobu Ishikawa Yuya Motohashi |
| author_sort | Yoshinobu Ishikawa |
| collection | DOAJ |
| description | 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 intramolecular O—H...O hydrogen bond with an adjacent carbonyl O atom. In the crystal, the molecules are linked through stacking interactions 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 molecules are further connected through C—H...O hydrogen bonds, forming inversion dimers. |
| first_indexed | 2024-12-10T16:48:41Z |
| format | Article |
| id | doaj.art-dd451d6b9ff34e60873f055eb573f636 |
| institution | Directory Open Access Journal |
| issn | 1600-5368 |
| language | English |
| last_indexed | 2024-12-10T16:48:41Z |
| publishDate | 2014-12-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E |
| spelling | doaj.art-dd451d6b9ff34e60873f055eb573f6362022-12-22T01:40:58ZengInternational Union of CrystallographyActa Crystallographica Section E1600-53682014-12-01701252252410.1107/S1600536814024684hb7275Crystal structure of (3,5-dichloro-2-hydroxyphenyl){1-[(naphthalen-1-yl)carbonyl]-1H-pyrazol-4-yl}methanoneYoshinobu Ishikawa0Yuya Motohashi1School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, JapanSchool of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, JapanThe 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 intramolecular O—H...O hydrogen bond with an adjacent carbonyl O atom. In the crystal, the molecules are linked through stacking interactions 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 molecules are further connected through C—H...O hydrogen bonds, forming inversion dimers.http://scripts.iucr.org/cgi-bin/paper?S1600536814024684crystal structurediaroyl pyrazolecyclizationstacking interactionC—H...O hydrogen bonding |
| spellingShingle | Yoshinobu Ishikawa Yuya Motohashi Crystal structure of (3,5-dichloro-2-hydroxyphenyl){1-[(naphthalen-1-yl)carbonyl]-1H-pyrazol-4-yl}methanone Acta Crystallographica Section E crystal structure diaroyl pyrazole cyclization stacking interaction C—H...O hydrogen bonding |
| title | Crystal structure of (3,5-dichloro-2-hydroxyphenyl){1-[(naphthalen-1-yl)carbonyl]-1H-pyrazol-4-yl}methanone |
| title_full | Crystal structure of (3,5-dichloro-2-hydroxyphenyl){1-[(naphthalen-1-yl)carbonyl]-1H-pyrazol-4-yl}methanone |
| title_fullStr | Crystal structure of (3,5-dichloro-2-hydroxyphenyl){1-[(naphthalen-1-yl)carbonyl]-1H-pyrazol-4-yl}methanone |
| title_full_unstemmed | Crystal structure of (3,5-dichloro-2-hydroxyphenyl){1-[(naphthalen-1-yl)carbonyl]-1H-pyrazol-4-yl}methanone |
| title_short | Crystal structure of (3,5-dichloro-2-hydroxyphenyl){1-[(naphthalen-1-yl)carbonyl]-1H-pyrazol-4-yl}methanone |
| title_sort | crystal structure of 3 5 dichloro 2 hydroxyphenyl 1 naphthalen 1 yl carbonyl 1h pyrazol 4 yl methanone |
| topic | crystal structure diaroyl pyrazole cyclization stacking interaction C—H...O hydrogen bonding |
| url | http://scripts.iucr.org/cgi-bin/paper?S1600536814024684 |
| work_keys_str_mv | AT yoshinobuishikawa crystalstructureof35dichloro2hydroxyphenyl1naphthalen1ylcarbonyl1hpyrazol4ylmethanone AT yuyamotohashi crystalstructureof35dichloro2hydroxyphenyl1naphthalen1ylcarbonyl1hpyrazol4ylmethanone |