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2-(7,8-Diphenyl-1H-imidazo[4,5-f]quinoxalin-2-yl)phenol methanol disolvate

The title compound, C(27)H(18)N(4)O·2CH(4)O, is a unsymmetrically substituted quinoxaline. An intra­molecular O—H⋯N hydrogen bond involving the hydr­oxy and imino groups generates an S(6) ring motif. Inter­molecular C—H⋯O and N—H⋯O hydrogen bonds form an R (2) (1)(7) ring motif involving a methanol...

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Detalles Bibliográficos
Autores principales: Fun, Hoong-Kun, Kia, Reza, Raithby, Paul R.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2008
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2960492/
https://www.ncbi.nlm.nih.gov/pubmed/21201724
http://dx.doi.org/10.1107/S1600536808025269
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author Fun, Hoong-Kun
Kia, Reza
Raithby, Paul R.
author_facet Fun, Hoong-Kun
Kia, Reza
Raithby, Paul R.
author_sort Fun, Hoong-Kun
collection PubMed
description The title compound, C(27)H(18)N(4)O·2CH(4)O, is a unsymmetrically substituted quinoxaline. An intra­molecular O—H⋯N hydrogen bond involving the hydr­oxy and imino groups generates an S(6) ring motif. Inter­molecular C—H⋯O and N—H⋯O hydrogen bonds form an R (2) (1)(7) ring motif involving a methanol O atom and two H atoms of the imidazole and benzene rings, respectively. The latter links neighbouring mol­ecules into one-dimensional extended chains along the a axis. The two benzene rings are inclined towards each other, as indicated by the dihedral angle of 52.13 (10)°. The phenol ring is almost coplanar with the basic quinoxaline unit, making a dihedral angle of 2.43 (6)°. The short distances between the centroids of the five- and six-membered rings prove the existence of π–π inter­actions [centroid–centroid distances = 3.5234 (9)–3.7885 (10) Å]. The crystal structure is stabilized by intra­molecular O—H⋯N, inter­molecular O—H⋯O, N—H⋯O and C—H⋯O (× 2) hydrogen bonds and weak inter­molecular C—H⋯π and π–π inter­actions.
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spelling pubmed-29604922010-12-30 2-(7,8-Diphenyl-1H-imidazo[4,5-f]quinoxalin-2-yl)phenol methanol disolvate Fun, Hoong-Kun Kia, Reza Raithby, Paul R. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(27)H(18)N(4)O·2CH(4)O, is a unsymmetrically substituted quinoxaline. An intra­molecular O—H⋯N hydrogen bond involving the hydr­oxy and imino groups generates an S(6) ring motif. Inter­molecular C—H⋯O and N—H⋯O hydrogen bonds form an R (2) (1)(7) ring motif involving a methanol O atom and two H atoms of the imidazole and benzene rings, respectively. The latter links neighbouring mol­ecules into one-dimensional extended chains along the a axis. The two benzene rings are inclined towards each other, as indicated by the dihedral angle of 52.13 (10)°. The phenol ring is almost coplanar with the basic quinoxaline unit, making a dihedral angle of 2.43 (6)°. The short distances between the centroids of the five- and six-membered rings prove the existence of π–π inter­actions [centroid–centroid distances = 3.5234 (9)–3.7885 (10) Å]. The crystal structure is stabilized by intra­molecular O—H⋯N, inter­molecular O—H⋯O, N—H⋯O and C—H⋯O (× 2) hydrogen bonds and weak inter­molecular C—H⋯π and π–π inter­actions. International Union of Crystallography 2008-08-13 /pmc/articles/PMC2960492/ /pubmed/21201724 http://dx.doi.org/10.1107/S1600536808025269 Text en © Fun et al. 2008 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
Fun, Hoong-Kun
Kia, Reza
Raithby, Paul R.
2-(7,8-Diphenyl-1H-imidazo[4,5-f]quinoxalin-2-yl)phenol methanol disolvate
title 2-(7,8-Diphenyl-1H-imidazo[4,5-f]quinoxalin-2-yl)phenol methanol disolvate
title_full 2-(7,8-Diphenyl-1H-imidazo[4,5-f]quinoxalin-2-yl)phenol methanol disolvate
title_fullStr 2-(7,8-Diphenyl-1H-imidazo[4,5-f]quinoxalin-2-yl)phenol methanol disolvate
title_full_unstemmed 2-(7,8-Diphenyl-1H-imidazo[4,5-f]quinoxalin-2-yl)phenol methanol disolvate
title_short 2-(7,8-Diphenyl-1H-imidazo[4,5-f]quinoxalin-2-yl)phenol methanol disolvate
title_sort 2-(7,8-diphenyl-1h-imidazo[4,5-f]quinoxalin-2-yl)phenol methanol disolvate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2960492/
https://www.ncbi.nlm.nih.gov/pubmed/21201724
http://dx.doi.org/10.1107/S1600536808025269
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