Hydrogen bonding in 2-amino-4,6-dimethoxypyrimidine, 2-benzylamino-4,6-bis(benzyloxy)pyrimidine and 2-amino-4,6-bis(N-pyrrolidino)pyrimidine: chains of fused rings and a centrosymmetric dimer.
Molecules of 2-amino-4,6-dimethoxypyrimidine, C(6)H(9)N(3)O(2), (I), are linked by two N-H.N hydrogen bonds [H.N 2.23 and 2.50 A, N.N 3.106 (2) and 3.261 (2) A, and N-H.N 171 and 145 degrees ] into a chain of fused rings, where alternate rings are generated by centres of inversion and twofold rotation axes. Adjacent chains are linked by aromatic pi-pi-stacking interactions to form a three-dimensional framework. In 2-benzylamino-4,6-bis(benzyloxy)pyrimidine, C(25)H(23)N(3)O(2), (II), the molecules are linked into centrosymmetric R(2)(2)(8) dimers by paired N-H.N hydrogen bonds [H.N 2.13 A, N.N 2.997 (2) A and N-H.N 170 degrees ]. Molecules of 2-amino-4,6-bis(N-pyrrolidino)pyrimidine, C(12)H(19)N(5), (III), are linked by two N-H.N hydrogen bonds [H.N 2.34 and 2.38 A, N.N 3.186 (2) and 3.254 (2) A, and N-H.N 163 and 170 degrees ] into a chain of fused rings similar to that in (I).
Low
John N
JN
Department of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland.
Quesada
Antonio
A
Marchal
Antonio
A
Melguizo
Manuel
M
Nogueras
Manuel
M
Glidewell
Christopher
C
D018360:Crystallography, X-Ray; D004260:DNA Repair / Q000187:drug effects; D019281:Dimerization; D006801:Humans; D006860:Hydrogen Bonding; D008958:Models, Molecular; D008968:Molecular Conformation; D019853:O(6)-Methylguanine-DNA Methyltransferase / Q000037:antagonists & inhibitors; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
D011743:Pyrimidines; D019853:O(6)-Methylguanine-DNA Methyltransferase