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Synthesis and crystal structure of 1-hydroxy-8-methyl-9H-carbazole-2-carbaldehyde
Two crystallographically independent molecules are present in the asymmetric unit of the title compound, C(14)H(11)NO(2), with virtually identical geometries. The carbazole units are planar. The hydroxy group at position 1, carbaldehyde group at position 2, and methyl group at position 8 (with the...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8423023/ https://www.ncbi.nlm.nih.gov/pubmed/34584751 http://dx.doi.org/10.1107/S2056989021007210 |
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author | Thiruvalluvar, Aravazhi Amalan Sridharan, M. Rajendra Prasad, K. J. Zeller, M. |
author_facet | Thiruvalluvar, Aravazhi Amalan Sridharan, M. Rajendra Prasad, K. J. Zeller, M. |
author_sort | Thiruvalluvar, Aravazhi Amalan |
collection | PubMed |
description | Two crystallographically independent molecules are present in the asymmetric unit of the title compound, C(14)H(11)NO(2), with virtually identical geometries. The carbazole units are planar. The hydroxy group at position 1, carbaldehyde group at position 2, and methyl group at position 8 (with the exception of two H atoms) are coplanar with the attached benzene rings. The dihedral angle between the two benzene rings is 2.20 (9)° in molecule A and 2.01 (9)° in molecule B. The pyrrole ring makes dihedral angles of 0.82 (10) and 1.40 (10)° [0.84 (10) and 1.18 (10)° in molecule B] with the (–CH(3))-substituted and (–OH and –CHO) substituted benzene rings, respectively. The molecular structure is stabilized by the intramolecular O—H⋯O hydrogen bonds, while the crystal structure features N—H⋯O and C—H⋯O hydrogen bonds. A range of π–π contacts further stabilizes the crystal structure. |
format | Online Article Text |
id | pubmed-8423023 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-84230232021-09-27 Synthesis and crystal structure of 1-hydroxy-8-methyl-9H-carbazole-2-carbaldehyde Thiruvalluvar, Aravazhi Amalan Sridharan, M. Rajendra Prasad, K. J. Zeller, M. Acta Crystallogr E Crystallogr Commun Jerry P. Jasinski tribute Two crystallographically independent molecules are present in the asymmetric unit of the title compound, C(14)H(11)NO(2), with virtually identical geometries. The carbazole units are planar. The hydroxy group at position 1, carbaldehyde group at position 2, and methyl group at position 8 (with the exception of two H atoms) are coplanar with the attached benzene rings. The dihedral angle between the two benzene rings is 2.20 (9)° in molecule A and 2.01 (9)° in molecule B. The pyrrole ring makes dihedral angles of 0.82 (10) and 1.40 (10)° [0.84 (10) and 1.18 (10)° in molecule B] with the (–CH(3))-substituted and (–OH and –CHO) substituted benzene rings, respectively. The molecular structure is stabilized by the intramolecular O—H⋯O hydrogen bonds, while the crystal structure features N—H⋯O and C—H⋯O hydrogen bonds. A range of π–π contacts further stabilizes the crystal structure. International Union of Crystallography 2021-07-16 /pmc/articles/PMC8423023/ /pubmed/34584751 http://dx.doi.org/10.1107/S2056989021007210 Text en © Thiruvalluvar et al. 2021 https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. |
spellingShingle | Jerry P. Jasinski tribute Thiruvalluvar, Aravazhi Amalan Sridharan, M. Rajendra Prasad, K. J. Zeller, M. Synthesis and crystal structure of 1-hydroxy-8-methyl-9H-carbazole-2-carbaldehyde |
title | Synthesis and crystal structure of 1-hydroxy-8-methyl-9H-carbazole-2-carbaldehyde |
title_full | Synthesis and crystal structure of 1-hydroxy-8-methyl-9H-carbazole-2-carbaldehyde |
title_fullStr | Synthesis and crystal structure of 1-hydroxy-8-methyl-9H-carbazole-2-carbaldehyde |
title_full_unstemmed | Synthesis and crystal structure of 1-hydroxy-8-methyl-9H-carbazole-2-carbaldehyde |
title_short | Synthesis and crystal structure of 1-hydroxy-8-methyl-9H-carbazole-2-carbaldehyde |
title_sort | synthesis and crystal structure of 1-hydroxy-8-methyl-9h-carbazole-2-carbaldehyde |
topic | Jerry P. Jasinski tribute |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8423023/ https://www.ncbi.nlm.nih.gov/pubmed/34584751 http://dx.doi.org/10.1107/S2056989021007210 |
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