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Crystal structure and Hirshfeld surface analysis of the anhydrous form of the nucleoside analogue entecavir
Author(s) -
Wang Xiaojuan,
Xu Hai-Jiang,
Jia Xue-Dong,
Yang Yan-Tao,
Zhang Xiao-Jian
Publication year - 2018
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229618002528
Subject(s) - anhydrous , entecavir , nucleoside , crystal structure , crystallography , surface (topology) , crystal (programming language) , nucleoside analogue , chemistry , materials science , stereochemistry , mathematics , computer science , geometry , biology , organic chemistry , virology , programming language , hepatitis b virus , virus , lamivudine
The nucleoside analogue entecavir {systematic name: 2‐amino‐9‐[(1 S ,3 R ,4 S )‐4‐hydroxy‐3‐hydroxymethyl‐2‐methylenecyclopentyl]‐1,9‐dihydro‐6 H ‐purin‐6‐one}, C 12 H 15 N 5 O 3 , is an antihepatitis B virus drug that has been approved in the US, EU and several countries worldwide. We report here the single‐crystal structure of the anhydrous form and compare it with that of the previously reported monohydrate form [Jiang & Liu (2009). Acta Cryst. E 65 , o2232]. Hirshfeld surface analysis has been employed to understand and visualize the subtle packing differences between the two crystalline forms. The results show that, compared to the previously reported hydrated form, the anhydrous crystal has significantly different intermolecular interactions and packing patterns.