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9-Chloro-1-methyl-7-phenyl-5,6-dihydro-13H-indolo[3,2-c]acridine

The title compound, C(26)H(19)ClN(2), is a 5,6-dihydro-13H-indolo[3,2-c]acridine prepared by condensation of a 2,3,4,9-tetra­hydro-1H-carbazol-1-one with 2-amino­benzophenone. The crystals undergo a destructive phase change upon cooling at varying temperatures between 270 and 200 K, depending on coo...

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Detalles Bibliográficos
Autores principales: Sridharan, Makuteswaran, Rajendra Prasad, Karnam J., Zeller, Matthias
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2009
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2977744/
https://www.ncbi.nlm.nih.gov/pubmed/21583880
http://dx.doi.org/10.1107/S1600536809013737
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author Sridharan, Makuteswaran
Rajendra Prasad, Karnam J.
Zeller, Matthias
author_facet Sridharan, Makuteswaran
Rajendra Prasad, Karnam J.
Zeller, Matthias
author_sort Sridharan, Makuteswaran
collection PubMed
description The title compound, C(26)H(19)ClN(2), is a 5,6-dihydro-13H-indolo[3,2-c]acridine prepared by condensation of a 2,3,4,9-tetra­hydro-1H-carbazol-1-one with 2-amino­benzophenone. The crystals undergo a destructive phase change upon cooling at varying temperatures between 270 and 200 K, depending on cooling rate and disturbance by vibration, thus indicating supercooling of the metastable room-temperature structure at lower temperature. The overall planarity of the indolo[3,2-c]acridine part of the mol­ecule is inter­rupted by the saturated ethyl­ene group, and the planes of the two halves exhibit a dihedral angle of 22.05 (6)° with each other while themselves being essentially planar. Packing is dominated by C—H⋯π inter­actions. No classical hydrogen bonds or stacking inter­actions are observed.
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spelling pubmed-29777442010-12-30 9-Chloro-1-methyl-7-phenyl-5,6-dihydro-13H-indolo[3,2-c]acridine Sridharan, Makuteswaran Rajendra Prasad, Karnam J. Zeller, Matthias Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(26)H(19)ClN(2), is a 5,6-dihydro-13H-indolo[3,2-c]acridine prepared by condensation of a 2,3,4,9-tetra­hydro-1H-carbazol-1-one with 2-amino­benzophenone. The crystals undergo a destructive phase change upon cooling at varying temperatures between 270 and 200 K, depending on cooling rate and disturbance by vibration, thus indicating supercooling of the metastable room-temperature structure at lower temperature. The overall planarity of the indolo[3,2-c]acridine part of the mol­ecule is inter­rupted by the saturated ethyl­ene group, and the planes of the two halves exhibit a dihedral angle of 22.05 (6)° with each other while themselves being essentially planar. Packing is dominated by C—H⋯π inter­actions. No classical hydrogen bonds or stacking inter­actions are observed. International Union of Crystallography 2009-04-18 /pmc/articles/PMC2977744/ /pubmed/21583880 http://dx.doi.org/10.1107/S1600536809013737 Text en © Sridharan 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
Sridharan, Makuteswaran
Rajendra Prasad, Karnam J.
Zeller, Matthias
9-Chloro-1-methyl-7-phenyl-5,6-dihydro-13H-indolo[3,2-c]acridine
title 9-Chloro-1-methyl-7-phenyl-5,6-dihydro-13H-indolo[3,2-c]acridine
title_full 9-Chloro-1-methyl-7-phenyl-5,6-dihydro-13H-indolo[3,2-c]acridine
title_fullStr 9-Chloro-1-methyl-7-phenyl-5,6-dihydro-13H-indolo[3,2-c]acridine
title_full_unstemmed 9-Chloro-1-methyl-7-phenyl-5,6-dihydro-13H-indolo[3,2-c]acridine
title_short 9-Chloro-1-methyl-7-phenyl-5,6-dihydro-13H-indolo[3,2-c]acridine
title_sort 9-chloro-1-methyl-7-phenyl-5,6-dihydro-13h-indolo[3,2-c]acridine
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2977744/
https://www.ncbi.nlm.nih.gov/pubmed/21583880
http://dx.doi.org/10.1107/S1600536809013737
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