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Supramolecular architecture in azaheterocyclic phosphonates. III. Structures of an ethyl phosphonamidate and an ethyl phosphonate
Author(s) -
Pietrzak Anna,
Modranka Jakub,
Wojciechowski Jakub,
Janecki Tomasz,
Wolf Wojciech M.
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/s2053229618009609
Subject(s) - phosphonate , chemistry , supramolecular chemistry , hydrogen bond , isopropyl , molecule , crystallography , crystal structure , crystal (programming language) , topology (electrical circuits) , stereochemistry , organic chemistry , mathematics , combinatorics , computer science , programming language
The novel crystal structures of ethyl ( S )‐ P ‐(4‐oxo‐4 H ‐benzo[4,5]thiazolo[3,2‐ a ]pyrimidin‐3‐yl)‐ N ‐[( R )‐1‐phenylethyl]phosphonamidate, C 20 H 20 N 3 O 3 PS, I , and diethyl (4‐isopropyl‐2‐oxo‐3,4‐dihydro‐2 H ‐benzo[4,5]thiazolo[3,2‐ a ]pyrimidin‐3‐yl)phosphonate, C 18 H 25 N 2 O 4 PS, II , were characterized by X‐ray diffraction analysis. The crystal packing of I is dominated by two infinite stacks composed of symmetry‐independent molecules linked by distinctively different hydrogen‐bond systems. The structure of II shows a ladder packing topology similar to those observed in related phosphorylated azaheterocycles. Structural studies are supplemented by calculations on the interactions stabilizing the molecular assemblies using the PIXEL method. Additionally, fingerprint plots derived from the Hirshfeld surfaces were generated for each structure to characterize the crystal packing arrangements in detail. The aromaticities of the heterocyclic moieties have been investigated using HOMA and HOMHED parametrization and compared with structures reported previously.