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Crystal structures of 2-(4-nitrophenyl)-3-phenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one and 2-(2-nitrophenyl)-3-phenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one
The crystal structures are reported of the isomeric compounds 2-(4-nitrophenyl)-3-phenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one, (I), and 2-(2-nitrophenyl)-3-phenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one, (II), both C(20)H(14)N(2)O(3)S, being the para-nitro and ortho-nitro forms, respectivel...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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International Union of Crystallography
2015
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4438845/ https://www.ncbi.nlm.nih.gov/pubmed/26029403 http://dx.doi.org/10.1107/S2056989015004545 |
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author | Yennawar, Hemant Cali, Aaron S. Xie, Yiwen Silverberg, Lee J. |
author_facet | Yennawar, Hemant Cali, Aaron S. Xie, Yiwen Silverberg, Lee J. |
author_sort | Yennawar, Hemant |
collection | PubMed |
description | The crystal structures are reported of the isomeric compounds 2-(4-nitrophenyl)-3-phenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one, (I), and 2-(2-nitrophenyl)-3-phenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one, (II), both C(20)H(14)N(2)O(3)S, being the para-nitro and ortho-nitro forms, respectively, the meta-form of which is known [Yennawar et al. (2013). Acta Cryst. E69, o1679]. The six-membered thiazone ring fused with a benzene ring displays a screw-boat conformation with a total puckering amplitude of 0.627 (1) Å in (I), and a near screw-boat conformation with a total puckering amplitude of 0.600 (1) Å in (II). The dihedral angles between the planes of the substituent nitrophenyl and phenyl and rings with the benzene ring of the parent benzothiazone moiety are 75.93 (5) and 82.61 (5)° [in (I)], and 76.79 (6) and 71.66 (6)° [in (II)]. Weak intermolecular C—H⋯O hydrogen-bonding interactions between aromatic H-atom donors and both a nitro-O atom and a thiazone O-atom acceptor in (I) and a thiazone O atom in (II) are present, forming in (I) a centrosymmetric 22-membered cyclic dimer which is extended through a similar inversion-related 14-membered cyclic hydrogen-bonding association into a zigzag chain structure extending along c. In (II), a single intermolecular C—H⋯O hydrogen bond gives a chain structure extending along b. In addition, weak C—H⋯π interactions are present in both structures [minimum C⋯ring-centroid separations = 3.630 (2) and 3.581 (2) Å, respectively]. |
format | Online Article Text |
id | pubmed-4438845 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-44388452015-05-30 Crystal structures of 2-(4-nitrophenyl)-3-phenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one and 2-(2-nitrophenyl)-3-phenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one Yennawar, Hemant Cali, Aaron S. Xie, Yiwen Silverberg, Lee J. Acta Crystallogr E Crystallogr Commun Research Communications The crystal structures are reported of the isomeric compounds 2-(4-nitrophenyl)-3-phenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one, (I), and 2-(2-nitrophenyl)-3-phenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one, (II), both C(20)H(14)N(2)O(3)S, being the para-nitro and ortho-nitro forms, respectively, the meta-form of which is known [Yennawar et al. (2013). Acta Cryst. E69, o1679]. The six-membered thiazone ring fused with a benzene ring displays a screw-boat conformation with a total puckering amplitude of 0.627 (1) Å in (I), and a near screw-boat conformation with a total puckering amplitude of 0.600 (1) Å in (II). The dihedral angles between the planes of the substituent nitrophenyl and phenyl and rings with the benzene ring of the parent benzothiazone moiety are 75.93 (5) and 82.61 (5)° [in (I)], and 76.79 (6) and 71.66 (6)° [in (II)]. Weak intermolecular C—H⋯O hydrogen-bonding interactions between aromatic H-atom donors and both a nitro-O atom and a thiazone O-atom acceptor in (I) and a thiazone O atom in (II) are present, forming in (I) a centrosymmetric 22-membered cyclic dimer which is extended through a similar inversion-related 14-membered cyclic hydrogen-bonding association into a zigzag chain structure extending along c. In (II), a single intermolecular C—H⋯O hydrogen bond gives a chain structure extending along b. In addition, weak C—H⋯π interactions are present in both structures [minimum C⋯ring-centroid separations = 3.630 (2) and 3.581 (2) Å, respectively]. International Union of Crystallography 2015-03-25 /pmc/articles/PMC4438845/ /pubmed/26029403 http://dx.doi.org/10.1107/S2056989015004545 Text en © Yennawar et al. 2015 http://creativecommons.org/licenses/by/2.0/uk/ 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.http://creativecommons.org/licenses/by/2.0/uk/ |
spellingShingle | Research Communications Yennawar, Hemant Cali, Aaron S. Xie, Yiwen Silverberg, Lee J. Crystal structures of 2-(4-nitrophenyl)-3-phenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one and 2-(2-nitrophenyl)-3-phenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one |
title | Crystal structures of 2-(4-nitrophenyl)-3-phenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one and 2-(2-nitrophenyl)-3-phenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one |
title_full | Crystal structures of 2-(4-nitrophenyl)-3-phenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one and 2-(2-nitrophenyl)-3-phenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one |
title_fullStr | Crystal structures of 2-(4-nitrophenyl)-3-phenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one and 2-(2-nitrophenyl)-3-phenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one |
title_full_unstemmed | Crystal structures of 2-(4-nitrophenyl)-3-phenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one and 2-(2-nitrophenyl)-3-phenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one |
title_short | Crystal structures of 2-(4-nitrophenyl)-3-phenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one and 2-(2-nitrophenyl)-3-phenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one |
title_sort | crystal structures of 2-(4-nitrophenyl)-3-phenyl-2,3-dihydro-4h-1,3-benzothiazin-4-one and 2-(2-nitrophenyl)-3-phenyl-2,3-dihydro-4h-1,3-benzothiazin-4-one |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4438845/ https://www.ncbi.nlm.nih.gov/pubmed/26029403 http://dx.doi.org/10.1107/S2056989015004545 |
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