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2-[4-(Piperidin-1-yl)-5H-chromeno[2,3-d]pyrimidin-2-yl]phenol

In the title compound, C(22)H(21)N(3)O(2), the pyrimidine ring is essentially planar [maximum deviation = 0.018 (2) Å] and forms dihedral angles of 22.70 (8) and 0.97 (7)°, respectively, with the fused benzene ring and the hy­droxy-substituted benzene ring. The piperidine ring has a chair conformati...

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Autores principales: Sharma, Naresh, Brahmachari, Goutam, Das, Suvankar, Kant, Rajni, Gupta, Vivek K.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3998607/
https://www.ncbi.nlm.nih.gov/pubmed/24826150
http://dx.doi.org/10.1107/S1600536814005625
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author Sharma, Naresh
Brahmachari, Goutam
Das, Suvankar
Kant, Rajni
Gupta, Vivek K.
author_facet Sharma, Naresh
Brahmachari, Goutam
Das, Suvankar
Kant, Rajni
Gupta, Vivek K.
author_sort Sharma, Naresh
collection PubMed
description In the title compound, C(22)H(21)N(3)O(2), the pyrimidine ring is essentially planar [maximum deviation = 0.018 (2) Å] and forms dihedral angles of 22.70 (8) and 0.97 (7)°, respectively, with the fused benzene ring and the hy­droxy-substituted benzene ring. The piperidine ring has a chair conformation and the pyran ring has a flattened twist-boat conformation. The hy­droxy group was refined as disordered over two sets of sites in a 0.702 (4):0.298 (4) ratio. The disorder corresponds to a rotation of approxomiately 180° about the C—C bond connecting the phenol group to the pyrimidine ring and hence, both the major and minor components of disorder form intra­molecular O—H⋯N hydrogen bonds. In the crystal, pairs of weak C—H⋯π inter­actions form inversion dimers. In addition, π–π inter­actions are observed between the pyrimidine ring and the hy­droxy-substituted benzene ring [centroid–centroid separation = 3.739 (2) Å].
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spelling pubmed-39986072014-05-13 2-[4-(Piperidin-1-yl)-5H-chromeno[2,3-d]pyrimidin-2-yl]phenol Sharma, Naresh Brahmachari, Goutam Das, Suvankar Kant, Rajni Gupta, Vivek K. Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound, C(22)H(21)N(3)O(2), the pyrimidine ring is essentially planar [maximum deviation = 0.018 (2) Å] and forms dihedral angles of 22.70 (8) and 0.97 (7)°, respectively, with the fused benzene ring and the hy­droxy-substituted benzene ring. The piperidine ring has a chair conformation and the pyran ring has a flattened twist-boat conformation. The hy­droxy group was refined as disordered over two sets of sites in a 0.702 (4):0.298 (4) ratio. The disorder corresponds to a rotation of approxomiately 180° about the C—C bond connecting the phenol group to the pyrimidine ring and hence, both the major and minor components of disorder form intra­molecular O—H⋯N hydrogen bonds. In the crystal, pairs of weak C—H⋯π inter­actions form inversion dimers. In addition, π–π inter­actions are observed between the pyrimidine ring and the hy­droxy-substituted benzene ring [centroid–centroid separation = 3.739 (2) Å]. International Union of Crystallography 2014-03-15 /pmc/articles/PMC3998607/ /pubmed/24826150 http://dx.doi.org/10.1107/S1600536814005625 Text en © Sharma 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 Organic Papers
Sharma, Naresh
Brahmachari, Goutam
Das, Suvankar
Kant, Rajni
Gupta, Vivek K.
2-[4-(Piperidin-1-yl)-5H-chromeno[2,3-d]pyrimidin-2-yl]phenol
title 2-[4-(Piperidin-1-yl)-5H-chromeno[2,3-d]pyrimidin-2-yl]phenol
title_full 2-[4-(Piperidin-1-yl)-5H-chromeno[2,3-d]pyrimidin-2-yl]phenol
title_fullStr 2-[4-(Piperidin-1-yl)-5H-chromeno[2,3-d]pyrimidin-2-yl]phenol
title_full_unstemmed 2-[4-(Piperidin-1-yl)-5H-chromeno[2,3-d]pyrimidin-2-yl]phenol
title_short 2-[4-(Piperidin-1-yl)-5H-chromeno[2,3-d]pyrimidin-2-yl]phenol
title_sort 2-[4-(piperidin-1-yl)-5h-chromeno[2,3-d]pyrimidin-2-yl]phenol
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3998607/
https://www.ncbi.nlm.nih.gov/pubmed/24826150
http://dx.doi.org/10.1107/S1600536814005625
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