Crystal structures of five 6-mercaptopurine derivatives
The crystal structures of five 6-mercaptopurine derivatives, viz. 2-[(9-acetyl-9H-purin-6-yl)sulfanyl]-1-(3-methoxyphenyl)ethan-1-one (1), C16H14N4O3S, 2-[(9-acetyl-9H-purin-6-yl)sulfanyl]-1-(4-methoxyphenyl)ethan-1-one (2), C16H14N4O3S, 2-[(9-acetyl-9H-purin-6-yl)sulfanyl]-1-(4-chlorophenyl)ethan-1...
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doaj-2a52fd2055c7414683acabbb1925f2bc2020-11-24T23:51:05ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902016-03-0172330731310.1107/S2056989016001833hb7562Crystal structures of five 6-mercaptopurine derivativesLígia R. Gomes0John Nicolson Low1Diogo Magalhães e Silva2Fernando Cagide3Fernanda Borges4FP–ENAS–Faculdade de Ciências de Saúde, Escola Superior de Saúde da UFP, Universidade Fernando Pessoa, Rua Carlos da Maia, 296, P-4200-150 Porto, PortugalDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, ScotlandCIQ/Departamento de Quιmica e Bioquιmica, Faculdade de Ciências, Universidade do Porto, 4169-007 Porto, PortugalCIQ/Departamento de Quιmica e Bioquιmica, Faculdade de Ciências, Universidade do Porto, 4169-007 Porto, PortugalCIQ/Departamento de Quιmica e Bioquιmica, Faculdade de Ciências, Universidade do Porto, 4169-007 Porto, PortugalThe crystal structures of five 6-mercaptopurine derivatives, viz. 2-[(9-acetyl-9H-purin-6-yl)sulfanyl]-1-(3-methoxyphenyl)ethan-1-one (1), C16H14N4O3S, 2-[(9-acetyl-9H-purin-6-yl)sulfanyl]-1-(4-methoxyphenyl)ethan-1-one (2), C16H14N4O3S, 2-[(9-acetyl-9H-purin-6-yl)sulfanyl]-1-(4-chlorophenyl)ethan-1-one (3), C15H11ClN4O2S, 2-[(9-acetyl-9H-purin-6-yl)sulfanyl]-1-(4-bromophenyl)ethan-1-one (4), C15H11BrN4O2S, and 1-(3-methoxyphenyl)-2-[(9H-purin-6-yl)sulfanyl]ethan-1-one (5), C14H12N4O2S. Compounds (2), (3) and (4) are isomorphous and accordingly their molecular and supramolecular structures are similar. An analysis of the dihedral angles between the purine and exocyclic phenyl rings show that the molecules of (1) and (5) are essentially planar but that in the case of the three isomorphous compounds (2), (3) and (4), these rings are twisted by a dihedral angle of approximately 38°. With the exception of (1) all molecules are linked by weak C—H...O hydrogen bonds in their crystals. There is π–π stacking in all compounds. A Cambridge Structural Database search revealed the existence of 11 deposited compounds containing the 1-phenyl-2-sulfanylethanone scaffold; of these, only eight have a cyclic ring as substituent, the majority of these being heterocycles.http://scripts.iucr.org/cgi-bin/paper?S2056989016001833crystal structuremercaptopurinessupramolecular structure |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Lígia R. Gomes John Nicolson Low Diogo Magalhães e Silva Fernando Cagide Fernanda Borges |
spellingShingle |
Lígia R. Gomes John Nicolson Low Diogo Magalhães e Silva Fernando Cagide Fernanda Borges Crystal structures of five 6-mercaptopurine derivatives Acta Crystallographica Section E: Crystallographic Communications crystal structure mercaptopurines supramolecular structure |
author_facet |
Lígia R. Gomes John Nicolson Low Diogo Magalhães e Silva Fernando Cagide Fernanda Borges |
author_sort |
Lígia R. Gomes |
title |
Crystal structures of five 6-mercaptopurine derivatives |
title_short |
Crystal structures of five 6-mercaptopurine derivatives |
title_full |
Crystal structures of five 6-mercaptopurine derivatives |
title_fullStr |
Crystal structures of five 6-mercaptopurine derivatives |
title_full_unstemmed |
Crystal structures of five 6-mercaptopurine derivatives |
title_sort |
crystal structures of five 6-mercaptopurine derivatives |
publisher |
International Union of Crystallography |
series |
Acta Crystallographica Section E: Crystallographic Communications |
issn |
2056-9890 |
publishDate |
2016-03-01 |
description |
The crystal structures of five 6-mercaptopurine derivatives, viz. 2-[(9-acetyl-9H-purin-6-yl)sulfanyl]-1-(3-methoxyphenyl)ethan-1-one (1), C16H14N4O3S, 2-[(9-acetyl-9H-purin-6-yl)sulfanyl]-1-(4-methoxyphenyl)ethan-1-one (2), C16H14N4O3S, 2-[(9-acetyl-9H-purin-6-yl)sulfanyl]-1-(4-chlorophenyl)ethan-1-one (3), C15H11ClN4O2S, 2-[(9-acetyl-9H-purin-6-yl)sulfanyl]-1-(4-bromophenyl)ethan-1-one (4), C15H11BrN4O2S, and 1-(3-methoxyphenyl)-2-[(9H-purin-6-yl)sulfanyl]ethan-1-one (5), C14H12N4O2S. Compounds (2), (3) and (4) are isomorphous and accordingly their molecular and supramolecular structures are similar. An analysis of the dihedral angles between the purine and exocyclic phenyl rings show that the molecules of (1) and (5) are essentially planar but that in the case of the three isomorphous compounds (2), (3) and (4), these rings are twisted by a dihedral angle of approximately 38°. With the exception of (1) all molecules are linked by weak C—H...O hydrogen bonds in their crystals. There is π–π stacking in all compounds. A Cambridge Structural Database search revealed the existence of 11 deposited compounds containing the 1-phenyl-2-sulfanylethanone scaffold; of these, only eight have a cyclic ring as substituent, the majority of these being heterocycles. |
topic |
crystal structure mercaptopurines supramolecular structure |
url |
http://scripts.iucr.org/cgi-bin/paper?S2056989016001833 |
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