Crystal structure of 5-tert-butyl-10,15,20-triphenylporphyrin

Crystal structure of 5-tert-butyl-10,15,20-triphenylporphyrin

In the title free base porphyrin, C42H34N4, the neighbouring N...N distances in the center of the ring vary from 2.818 (8) to 2.998 (8) Å and the phenyl rings are tilted from the 24-atom mean plane at angles varying between 62.42 (2)–71.63 (2)°. The NH groups are involved in intramolecular bifurcate...

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Main Authors: Keith J. Flanagan, Ebrahim Mohamed Mothi, Lisa Kötzner, Mathias O. Senge
Format: Article
Language:English
Published: International Union of Crystallography 2016-02-01
Series:Acta Crystallographica Section E: Crystallographic Communications
Subjects:
crystal structure
unsymmetrical porphyrins
free base porphyrin
non-planar porphyrins.
Online Access:http://scripts.iucr.org/cgi-bin/paper?S2056989016000025
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spelling doaj-69d1bde5829e48e58feddce0b5bc1ba02020-11-24T22:29:36ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902016-02-0172212813210.1107/S2056989016000025su5266Crystal structure of 5-tert-butyl-10,15,20-triphenylporphyrinKeith J. Flanagan0Ebrahim Mohamed Mothi1Lisa Kötzner2Mathias O. Senge3School of Chemistry, SFI Tetrapyrrole Laboratory, Trinity Biomedical Sciences Institute, 152-160 Pearse Street, Trinity College Dublin, The University of Dublin, Dublin 2, IrelandCentre for Scientific and Applied Research, PSN College of Engineering and Technology, Melathediyoor, Tirunelveli 627 152, IndiaSchool of Chemistry, SFI Tetrapyrrole Laboratory, Trinity Biomedical Sciences Institute, 152-160 Pearse Street, Trinity College Dublin, The University of Dublin, Dublin 2, IrelandSchool of Chemistry, SFI Tetrapyrrole Laboratory, Trinity Biomedical Sciences Institute, 152-160 Pearse Street, Trinity College Dublin, The University of Dublin, Dublin 2, IrelandIn the title free base porphyrin, C42H34N4, the neighbouring N...N distances in the center of the ring vary from 2.818 (8) to 2.998 (8) Å and the phenyl rings are tilted from the 24-atom mean plane at angles varying between 62.42 (2)–71.63 (2)°. The NH groups are involved in intramolecular bifurcated N—H...(N,N) hydrogen bonds. The Ca—Cm—Ca angles vary slightly for the phenyl rings, between 124.19 (18)–126.17 (18)°. The largest deviation from the mean plane of the 24-atom macrocycle is associated with the meso carbon at the substituted tert-butyl position, which is displaced from the mean plane by 0.44 (2) Å. The free base porphyrin is characterized by a significant degree of ruffled (B1u) distortion with contributions from domed (A2u) and wave [Eg(y) and Eg(x)] modes. In the crystal, molecules are linked by a number of weak C—H...π interactions, forming a three-dimensional framework. The structure was refined as a two-component inversion twin.http://scripts.iucr.org/cgi-bin/paper?S2056989016000025crystal structureunsymmetrical porphyrinsfree base porphyrinnon-planar porphyrins.
collection DOAJ
language English
format Article
sources DOAJ
author Keith J. Flanagan
Ebrahim Mohamed Mothi
Lisa Kötzner
Mathias O. Senge
spellingShingle Keith J. Flanagan
Ebrahim Mohamed Mothi
Lisa Kötzner
Mathias O. Senge
Crystal structure of 5-tert-butyl-10,15,20-triphenylporphyrin
Acta Crystallographica Section E: Crystallographic Communications
crystal structure
unsymmetrical porphyrins
free base porphyrin
non-planar porphyrins.
author_facet Keith J. Flanagan
Ebrahim Mohamed Mothi
Lisa Kötzner
Mathias O. Senge
author_sort Keith J. Flanagan
title Crystal structure of 5-tert-butyl-10,15,20-triphenylporphyrin
title_short Crystal structure of 5-tert-butyl-10,15,20-triphenylporphyrin
title_full Crystal structure of 5-tert-butyl-10,15,20-triphenylporphyrin
title_fullStr Crystal structure of 5-tert-butyl-10,15,20-triphenylporphyrin
title_full_unstemmed Crystal structure of 5-tert-butyl-10,15,20-triphenylporphyrin
title_sort crystal structure of 5-tert-butyl-10,15,20-triphenylporphyrin
publisher International Union of Crystallography
series Acta Crystallographica Section E: Crystallographic Communications
issn 2056-9890
publishDate 2016-02-01
description In the title free base porphyrin, C42H34N4, the neighbouring N...N distances in the center of the ring vary from 2.818 (8) to 2.998 (8) Å and the phenyl rings are tilted from the 24-atom mean plane at angles varying between 62.42 (2)–71.63 (2)°. The NH groups are involved in intramolecular bifurcated N—H...(N,N) hydrogen bonds. The Ca—Cm—Ca angles vary slightly for the phenyl rings, between 124.19 (18)–126.17 (18)°. The largest deviation from the mean plane of the 24-atom macrocycle is associated with the meso carbon at the substituted tert-butyl position, which is displaced from the mean plane by 0.44 (2) Å. The free base porphyrin is characterized by a significant degree of ruffled (B1u) distortion with contributions from domed (A2u) and wave [Eg(y) and Eg(x)] modes. In the crystal, molecules are linked by a number of weak C—H...π interactions, forming a three-dimensional framework. The structure was refined as a two-component inversion twin.
topic crystal structure
unsymmetrical porphyrins
free base porphyrin
non-planar porphyrins.
url http://scripts.iucr.org/cgi-bin/paper?S2056989016000025
work_keys_str_mv AT keithjflanagan crystalstructureof5tertbutyl101520triphenylporphyrin
AT ebrahimmohamedmothi crystalstructureof5tertbutyl101520triphenylporphyrin
AT lisakotzner crystalstructureof5tertbutyl101520triphenylporphyrin
AT mathiasosenge crystalstructureof5tertbutyl101520triphenylporphyrin
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