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4-(2-Nitrobenzyl)-3-phenyl-3,4-dihydro-2H-1,4-benzoxazin-2-ol
The title compound, C(21)H(18)N(2)O(4), crystallizes with two independent molecules (A and B) in the asymmetric unit. In both molecules the oxazine ring has an envelope conformation with the hydroxyl-substituted C atom as the flap. The nitrobenzyl ring and the phenyl ring are almost normal to the...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2014
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4158540/ https://www.ncbi.nlm.nih.gov/pubmed/25249912 http://dx.doi.org/10.1107/S1600536814015645 |
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author | Chouguiat, Louisa Boulcina, Raouf Bouacida, Sofiane Merazig, Hocine Debache, Abdelmadjid |
author_facet | Chouguiat, Louisa Boulcina, Raouf Bouacida, Sofiane Merazig, Hocine Debache, Abdelmadjid |
author_sort | Chouguiat, Louisa |
collection | PubMed |
description | The title compound, C(21)H(18)N(2)O(4), crystallizes with two independent molecules (A and B) in the asymmetric unit. In both molecules the oxazine ring has an envelope conformation with the hydroxyl-substituted C atom as the flap. The nitrobenzyl ring and the phenyl ring are almost normal to the mean plane of the benzooxazine ring system with dihdral angles of 85.72 (15) and 82.69 (15)°, respectively, in molecule A, and 85.79 (15) and 87.72 (15)°, respectively, in molecule B. The main difference in the conformation of the two molecules concerns the dihedral angle between the nitrobenzyl ring and the phenyl ring, viz. 79.67 (18) in molecule A and 71.13 (18)° in molecule B. In the crystal, the A and B molecules are linked by an O—H⋯O hydrogen bond. These units are then linked via C—H⋯O hydrogen bonds, forming sheets lying parallel to (010). Further C—H⋯O hydrogen bonds link the sheets to form a three-dimensional network. There are also O—H⋯π and C—H⋯π interactions present, reinforcing the three-dimensional structure. |
format | Online Article Text |
id | pubmed-4158540 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-41585402014-09-23 4-(2-Nitrobenzyl)-3-phenyl-3,4-dihydro-2H-1,4-benzoxazin-2-ol Chouguiat, Louisa Boulcina, Raouf Bouacida, Sofiane Merazig, Hocine Debache, Abdelmadjid Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(21)H(18)N(2)O(4), crystallizes with two independent molecules (A and B) in the asymmetric unit. In both molecules the oxazine ring has an envelope conformation with the hydroxyl-substituted C atom as the flap. The nitrobenzyl ring and the phenyl ring are almost normal to the mean plane of the benzooxazine ring system with dihdral angles of 85.72 (15) and 82.69 (15)°, respectively, in molecule A, and 85.79 (15) and 87.72 (15)°, respectively, in molecule B. The main difference in the conformation of the two molecules concerns the dihedral angle between the nitrobenzyl ring and the phenyl ring, viz. 79.67 (18) in molecule A and 71.13 (18)° in molecule B. In the crystal, the A and B molecules are linked by an O—H⋯O hydrogen bond. These units are then linked via C—H⋯O hydrogen bonds, forming sheets lying parallel to (010). Further C—H⋯O hydrogen bonds link the sheets to form a three-dimensional network. There are also O—H⋯π and C—H⋯π interactions present, reinforcing the three-dimensional structure. International Union of Crystallography 2014-07-11 /pmc/articles/PMC4158540/ /pubmed/25249912 http://dx.doi.org/10.1107/S1600536814015645 Text en © Chouguiat et al. 2014 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 Chouguiat, Louisa Boulcina, Raouf Bouacida, Sofiane Merazig, Hocine Debache, Abdelmadjid 4-(2-Nitrobenzyl)-3-phenyl-3,4-dihydro-2H-1,4-benzoxazin-2-ol |
title | 4-(2-Nitrobenzyl)-3-phenyl-3,4-dihydro-2H-1,4-benzoxazin-2-ol |
title_full | 4-(2-Nitrobenzyl)-3-phenyl-3,4-dihydro-2H-1,4-benzoxazin-2-ol |
title_fullStr | 4-(2-Nitrobenzyl)-3-phenyl-3,4-dihydro-2H-1,4-benzoxazin-2-ol |
title_full_unstemmed | 4-(2-Nitrobenzyl)-3-phenyl-3,4-dihydro-2H-1,4-benzoxazin-2-ol |
title_short | 4-(2-Nitrobenzyl)-3-phenyl-3,4-dihydro-2H-1,4-benzoxazin-2-ol |
title_sort | 4-(2-nitrobenzyl)-3-phenyl-3,4-dihydro-2h-1,4-benzoxazin-2-ol |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4158540/ https://www.ncbi.nlm.nih.gov/pubmed/25249912 http://dx.doi.org/10.1107/S1600536814015645 |
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