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Crystal structure of 3-[4-(1-methyl­eth­yl)phen­yl]-1-(naphthalen-2-yl)prop-2-en-1-one

The title compound, C(22)H(20)O, was synthesized by reacting 4-iso­propyl­benzaldehyde with 2-acetonaphtone by aldolic condensation under Claisen–Schmidt conditions. The mol­ecule consists of a naphthalene group and a benzene ring with a pendant isopropyl moiety, both rings bound by a propenone link...

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Autores principales: Assia, Sid, Amel, Messai, Nouara, Ziani, Mahieddine, Mokhtari, Kaddour, Lamara
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4186083/
https://www.ncbi.nlm.nih.gov/pubmed/25309196
http://dx.doi.org/10.1107/S1600536814017528
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author Assia, Sid
Amel, Messai
Nouara, Ziani
Mahieddine, Mokhtari
Kaddour, Lamara
author_facet Assia, Sid
Amel, Messai
Nouara, Ziani
Mahieddine, Mokhtari
Kaddour, Lamara
author_sort Assia, Sid
collection PubMed
description The title compound, C(22)H(20)O, was synthesized by reacting 4-iso­propyl­benzaldehyde with 2-acetonaphtone by aldolic condensation under Claisen–Schmidt conditions. The mol­ecule consists of a naphthalene group and a benzene ring with a pendant isopropyl moiety, both rings bound by a propenone linker. The naphthalene ring system is almost planar [maximum deviation from the least-squares plane = 0.026 (10) Å] and subtends a dihedral angle of 52.31 (4)° with the benzene ring. The propenone linker, in turn, deviates slightly more from planarity [maximum deviation = 0.125 (18) Å] and has its least-squares plane oriented midway the former two, at 25.62 (6) and 28.02 (5)° from the naphthalene ring system and the benzene ring, respectively. Finally, the isopropyl group presents its CC(2) plane almost perpendicular to the benzene ring, at 85.30 (4)°. No significant hydrogen bonding or π–π stacking inter­actions are found in the crystal structure.
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spelling pubmed-41860832014-10-12 Crystal structure of 3-[4-(1-methyl­eth­yl)phen­yl]-1-(naphthalen-2-yl)prop-2-en-1-one Assia, Sid Amel, Messai Nouara, Ziani Mahieddine, Mokhtari Kaddour, Lamara Acta Crystallogr Sect E Struct Rep Online Data Reports The title compound, C(22)H(20)O, was synthesized by reacting 4-iso­propyl­benzaldehyde with 2-acetonaphtone by aldolic condensation under Claisen–Schmidt conditions. The mol­ecule consists of a naphthalene group and a benzene ring with a pendant isopropyl moiety, both rings bound by a propenone linker. The naphthalene ring system is almost planar [maximum deviation from the least-squares plane = 0.026 (10) Å] and subtends a dihedral angle of 52.31 (4)° with the benzene ring. The propenone linker, in turn, deviates slightly more from planarity [maximum deviation = 0.125 (18) Å] and has its least-squares plane oriented midway the former two, at 25.62 (6) and 28.02 (5)° from the naphthalene ring system and the benzene ring, respectively. Finally, the isopropyl group presents its CC(2) plane almost perpendicular to the benzene ring, at 85.30 (4)°. No significant hydrogen bonding or π–π stacking inter­actions are found in the crystal structure. International Union of Crystallography 2014-08-16 /pmc/articles/PMC4186083/ /pubmed/25309196 http://dx.doi.org/10.1107/S1600536814017528 Text en © Assia et al. 2014 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Data Reports
Assia, Sid
Amel, Messai
Nouara, Ziani
Mahieddine, Mokhtari
Kaddour, Lamara
Crystal structure of 3-[4-(1-methyl­eth­yl)phen­yl]-1-(naphthalen-2-yl)prop-2-en-1-one
title Crystal structure of 3-[4-(1-methyl­eth­yl)phen­yl]-1-(naphthalen-2-yl)prop-2-en-1-one
title_full Crystal structure of 3-[4-(1-methyl­eth­yl)phen­yl]-1-(naphthalen-2-yl)prop-2-en-1-one
title_fullStr Crystal structure of 3-[4-(1-methyl­eth­yl)phen­yl]-1-(naphthalen-2-yl)prop-2-en-1-one
title_full_unstemmed Crystal structure of 3-[4-(1-methyl­eth­yl)phen­yl]-1-(naphthalen-2-yl)prop-2-en-1-one
title_short Crystal structure of 3-[4-(1-methyl­eth­yl)phen­yl]-1-(naphthalen-2-yl)prop-2-en-1-one
title_sort crystal structure of 3-[4-(1-methyl­eth­yl)phen­yl]-1-(naphthalen-2-yl)prop-2-en-1-one
topic Data Reports
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4186083/
https://www.ncbi.nlm.nih.gov/pubmed/25309196
http://dx.doi.org/10.1107/S1600536814017528
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