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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...

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Autores principales: Yennawar, Hemant, Cali, Aaron S., Xie, Yiwen, Silverberg, Lee J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2015
Materias:
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].
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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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