title: Supramolecular structures constructed by 3-(2-amino-6-chloropyrimidin-4-yl)-1,1-dimethylprop-2-yn-1-ol monohydrate and 3-[2-amino-6-(3-hydroxy-3,3-dimethylprop-1-yn-1-yl)pyrimidin-4-yl]-1,1-dimethylprop-2-yn-1-ol.
abstract: The molecule of 3-(2-amino-6-chloropyrimidin-4-yl)-1,1-dimethylprop-2-yn-1-ol monohydrate, C(9)H(10)ClN(3)O·H(2)O, (I), shows a very polarized molecular-electronic structure, while the polarization is slight for 3-[2-amino-6-(3-hydroxy-3,3-dimethylprop-1-yn-1-yl)pyrimidin-4-yl]-1,1-dimethylprop-2-yn-1-ol, C(14)H(17)N(3)O(2), (II). In the supramolecular structure of (I), a combination of hard N-H···N hydrogen bonds and soft C-H···N hydrogen bonds creates a molecular column. Aromatic π-π stackings between the pyrimidine rings stabilize the column with perpendicular and centroid-centroid distances of 3.283 (3) and 3.588 (1) Å, respectively. Short Cl···Cl contacts further link neighbouring molecular columns, creating a hydrophilic tube in which water molecules are fixed by various hydrogen bonds. In the packing of (II), a one-dimensional molecular chain is formed through several contacts involving hard N-H···O(N) and O-H···O(N) and soft C-H···O hydrogen bonds. Interchain O-H···O hydrogen bonds link the chains giving a two-dimensional stepped network. It is anticipated that study of the influence of hydrogen bonding on the patterns of base pairing and molecular packing in aminopyrimidine structures will shed significant light on nucleic acid structures as well as their functions.
authors: Department of Chemistry, Shandong Normal University, Jinan 250014, People's Republic of China.
authors: Yuan
authors: Y
authors: Cheng
authors: Lu-Sheng
authors: LS
authors: Chen
authors: Qi-Kui
authors: QK
authors: Liu
authors: Jun
authors: J
authors: Wu
authors: Dian-Shun
authors: DS
authors: Guo
mesh_terms: D020029:Base Pairing; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D008958:Models, Molecular; D015394:Molecular Structure; D009696:Nucleic Acids / Q000737:chemistry*; D020005:Propanols / Q000737:chemistry*; D011743:Pyrimidines / Q000737:chemistry*
chemical_list: C561860:3-(2-amino-6-(3-hydroxy-3,3-dimethylprop-1-yn-1-yl)pyrimidin-4-yl)-1,1-dimethylprop-2-yn-1-ol; C561861:3-(2-amino-6-chloropyrimidin-4-yl)-1,1-dimethylprop-2-yn-1-ol monohydrate; D009696:Nucleic Acids; D020005:Propanols; D011743:Pyrimidines