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

The molecule of 3‐(2‐amino‐6‐chloropyrimidin‐4‐yl)‐1,1‐dimethylprop‐2‐yn‐1‐ol monohydrate, C9H10ClN3O·H2O, (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...

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Published in:Acta crystallographica. Section C, Crystal structure communications Crystal structure communications, 2011-07, Vol.67 (7), p.o244-o248
Main Authors: Cheng, Yuan, Chen, Lu-Sheng, Liu, Qi-Kui, Wu, Jun, Guo, Dian-Shun
Format: Article
Language:English
Subjects:
Base Pairing
Chemical compounds
Crystal structure
Crystallography
Crystallography, X-Ray
Hydrogen Bonding
Hydrogen bonds
Models, Molecular
Molecular Structure
Molecules
Nucleic Acids - chemistry
Propanols - chemistry
Pyrimidines - chemistry
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Summary:The molecule of 3‐(2‐amino‐6‐chloropyrimidin‐4‐yl)‐1,1‐dimethylprop‐2‐yn‐1‐ol monohydrate, C9H10ClN3O·H2O, (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, C14H17N3O2, (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.
ISSN:0108-2701
1600-5759
DOI:10.1107/S0108270111019895