(1-Adamant­yl)(4-amino­phen­yl)methanol

In the racemic crystal of the title compound, C(17)H(23)NO, enanti­omers of the two crystallographically independent mol­ecules are linked into face-to-face RSdimers via inter­molecular O—H⋯N hydrogen bonds and π–π inter­actions with centroid–centroid distances of 3.7610 (2) Å. The mol­ecules adopt...

Descripción completa

Detalles Bibliográficos
Autores principales: Rouchal, Michal, Nečas, Marek, Vícha, Robert
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2009
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2977704/
https://www.ncbi.nlm.nih.gov/pubmed/21583840
http://dx.doi.org/10.1107/S1600536809012987
_version_ 1782191168292913152
author Rouchal, Michal
Nečas, Marek
Vícha, Robert
author_facet Rouchal, Michal
Nečas, Marek
Vícha, Robert
author_sort Rouchal, Michal
collection PubMed
description In the racemic crystal of the title compound, C(17)H(23)NO, enanti­omers of the two crystallographically independent mol­ecules are linked into face-to-face RSdimers via inter­molecular O—H⋯N hydrogen bonds and π–π inter­actions with centroid–centroid distances of 3.7610 (2) Å. The mol­ecules adopt slightly different conformations and contain an adamantane cage consisting of three fused cyclo­hexane rings in almost ideal chair conformations, with C—C—C angles varying within the range 107.2 (4)–111.4 (4)°. In the hydrogen-bonded pair, the benzene rings are almost coplanar, the dihedral angle between them being 1.29 (13)°. The mol­ecular packing in the crystal is stabilized by additional inter­molecular N—H⋯O hydrogen bonds.
format Text
id pubmed-2977704
institution National Center for Biotechnology Information
language English
publishDate 2009
publisher International Union of Crystallography
record_format MEDLINE/PubMed
spelling pubmed-29777042010-12-30 (1-Adamant­yl)(4-amino­phen­yl)methanol Rouchal, Michal Nečas, Marek Vícha, Robert Acta Crystallogr Sect E Struct Rep Online Organic Papers In the racemic crystal of the title compound, C(17)H(23)NO, enanti­omers of the two crystallographically independent mol­ecules are linked into face-to-face RSdimers via inter­molecular O—H⋯N hydrogen bonds and π–π inter­actions with centroid–centroid distances of 3.7610 (2) Å. The mol­ecules adopt slightly different conformations and contain an adamantane cage consisting of three fused cyclo­hexane rings in almost ideal chair conformations, with C—C—C angles varying within the range 107.2 (4)–111.4 (4)°. In the hydrogen-bonded pair, the benzene rings are almost coplanar, the dihedral angle between them being 1.29 (13)°. The mol­ecular packing in the crystal is stabilized by additional inter­molecular N—H⋯O hydrogen bonds. International Union of Crystallography 2009-04-10 /pmc/articles/PMC2977704/ /pubmed/21583840 http://dx.doi.org/10.1107/S1600536809012987 Text en © Rouchal et al. 2009 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
Rouchal, Michal
Nečas, Marek
Vícha, Robert
(1-Adamant­yl)(4-amino­phen­yl)methanol
title (1-Adamant­yl)(4-amino­phen­yl)methanol
title_full (1-Adamant­yl)(4-amino­phen­yl)methanol
title_fullStr (1-Adamant­yl)(4-amino­phen­yl)methanol
title_full_unstemmed (1-Adamant­yl)(4-amino­phen­yl)methanol
title_short (1-Adamant­yl)(4-amino­phen­yl)methanol
title_sort (1-adamant­yl)(4-amino­phen­yl)methanol
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2977704/
https://www.ncbi.nlm.nih.gov/pubmed/21583840
http://dx.doi.org/10.1107/S1600536809012987
work_keys_str_mv AT rouchalmichal 1adamantyl4aminophenylmethanol
AT necasmarek 1adamantyl4aminophenylmethanol
AT vicharobert 1adamantyl4aminophenylmethanol

Ejemplares similares