Acta Crystallographica Section B

Structural Science

Volume 60, Part 1 (February 2004)

Acta Cryst. (2004). B60, 76-89 [doi:10.1107/S0108768103024856]

Symmetrically 4,6-disubstituted 2-aminopyrimidines and 2-amino-5-nitrosopyrimidines: interplay of molecular, molecular-electronic and supramolecular structures

A. Quesada, A. Marchal, M. Melguizo, J. N. Low and C. Glidewell

Abstract: The structures of six symmetrically 4,6-disubstituted 2-aminopyrimidines, four of them containing a 5-nitroso substituent, have been determined. The nitroso compounds, in particular, exhibit polarized molecular-electronic structures leading to extensive charge-assisted hydrogen bonding. The intermolecular interactions observed include hard hydrogen bonds of N-HN and N-HO types together with O-HO and O-HN types in 2-amino-4,6-bis(2-hydroxyethylamino)-5-nitrosopyrimidine; soft hydrogen bonds of the C-HO type in both 2-amino-4,6-bis(morpholino)-5-nitrosopyrimidine (3) and 2-amino-4,6-bis(benzylamino)-5-nitrosopyrimidine (4), and of the C-H [bold pi] (arene) type in both 2-amino-4,6-bis(piperidino)pyrimidine (1) and 2-amino-5-nitroso-4,6-bis(3-pyridylmethoxy)pyrimidine (5); and aromatic stacking interactions in 2-amino-5-nitroso-4,6-bis(3-pyridylmethoxy)pyrimidine. The supramolecular structures formed by the hard hydrogen bonds are finite, zero-dimensional in (1), one-dimensional in 2-amino-4,6-bis(3-pyridylmethoxy)pyrimidine (2), two-dimensional in both (3) and (4), and three-dimensional in both (5) and 2-amino-4,6-bis(2-hydroxyethylamino)-5-nitrosopyrimidine.

Online 21 January 2004


	Structure factor file (CIF format) (152.1 kbytes) Contains datablock I

	Structure factor file (CIF format) (481.6 kbytes) Contains datablock 267

	Structure factor file (CIF format) (151.9 kbytes) Contains datablock 258

	Structure factor file (CIF format) (177.4 kbytes) Contains datablock 329

	Structure factor file (CIF format) (99.7 kbytes) Contains datablock V

	Structure factor file (CIF format) (116.3 kbytes) Contains datablock 264

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