Structural Chemistry

, Volume 21, Issue 1, pp 245–254 | Cite as

X-ray crystal structures of halogen containing nucleobase derivatives in unsolvated and DMSO solvated forms

Original Research


A series of halogenated nucleobase derivatives 14 is reported to yield solvent-free (2) and DMSO solvated crystals (1, 3, 4) on the crystallization from DMSO with one of them (4) containing an additional molecule of water. The molecular and crystal structures are described and comparatively discussed with reference to previous results on related compounds. The molecule of 1 is planar, molecules of 2 and 3 show syn alignment with reference to the heterocyclic ring and common C2′-endo conformation of the ribose residue, while 4 is also syn aligned but C4′-exo in the sugar conformation. The packing structures reveal typical aggregations created via networks of hydrogen bonds. These involve conventional N–H···N, N–H···O and O–H···O interactions between nucleobase and ribose units as well as solvent molecules, additionally supported by weak C–H···O contacts but excluding the participation of halogen···halogen interactions as well as halogen···heteroatom contacts in the supramolecular structure formation.


Nucleobase derivatives Halogen compounds DMSO solvates X-ray analysis Hydrogen bonding 


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Copyright information

© Springer Science+Business Media, LLC 2009

Authors and Affiliations

  1. 1.Institut für Organische ChemieTechnische Universität Bergakademie FreibergFreibergGermany

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