Crystal structures of five 6-mercaptopurine derivatives

• Type: Article in International Scientific Journal
• Date: 2016

Authors

Gomes, LR (Author) Other; Low, JN (Author) Other; Silva, DME (Author) Other; Fernando Cagide (Author) FCUP; Fernanda Borges (Author) FCUP

Journal

Title: Acta Crystallographica Section E: Crystallographic Communications

Vol. 72

Pages: 307-+

Publisher: International Union of Crystallography

Indexing

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Other information

Authenticus ID: P-00K-8VE

DOI: 10.1107/s2056989016001833

Abstract (EN): 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 degrees. With the exception of (1) all molecules are linked by weak C-H center dot center dot center dot O hydrogen bonds in their crystals. There is pi-pi 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.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 27