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Salt forms of sulfadiazine with alkali metal and organic cations
Author(s) -
Campbell Gemma,
Fisher Rebecca,
Kennedy Alan R.,
King Nathan L. C.,
Spiteri Rebecca
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/s205322961800414x
Subject(s) - chemistry , deprotonation , protonation , alkali metal , aniline , medicinal chemistry , sulfonyl , coordination polymer , crystallography , hydrazone , crystal structure , stereochemistry , inorganic chemistry , ion , organic chemistry , alkyl
The structures of four salt forms of sulfadiazine (SDH) with alkali metal cations are presented. Three contain the deprotonated SD anion (C 10 H 9 N 4 O 2 S). These are the discrete complex diaqua{4‐[(pyrimidin‐2‐ylazanidyl‐κ N 1 )sulfonyl‐κ O ]aniline}lithium(I), [Li(SD)(H 2 O) 2 ], (I), and the coordination polymers poly[{μ 3 ‐4‐[(pyrimidin‐2‐ylazanidyl)sulfonyl]aniline}sodium(I)], [Na(SD)] n , (II), and poly[diaqua{μ 3 ‐4‐[(pyrimidin‐2‐ylazanidyl)sulfonyl]aniline}potassium(I)], [K(SD)(H 2 O) 2 ] n , (III). Na complex (II) is a three‐dimensional coordination polymer, whilst K complex (III) has two crystallographically independent [K(SD)(H 2 O) 2 ] units per asymmetric unit ( Z ′ = 2) and gives a two‐dimensional coordination polymer whose layers propagate parallel to the crystallographic ab plane. The different bonding modes of the SD anion in these three complexes is discussed. Structure (IV) contains protonated SDH 2 cations {4‐[(pyrimidin‐2‐yl)sulfamoyl]anilinium, C 10 H 11 N 4 O 2 S} and the Orange G dianion [OG, 7‐oxo‐8‐(phenylhydrazinylidene)naphthalene‐1,3‐disulfonate, C 16 H 10 N 2 O 7 S 2 ], namely, 4‐[(pyrimidin‐2‐yl)sulfamoyl]anilinium tetraaqua[7‐oxo‐8‐(phenylhydrazinylidene)naphthalene‐1,3‐disulfonato]sodium(I) sesquihydrate, (SDH 2 )[Na(OG)(H 2 O) 4 ]·1.5H 2 O. The [Na(OG)(H 2 O) 4 ] 2 dimers have antiparallel naphthyl ring structures joined through two Na centres that bond to the hydrazone anions through the O atoms of the ketone and sulfonate substituents. The structures of the salts formed on reaction of SDH with 2‐aminopyridine and ethanolamine are also presented as 2‐aminopyridinium 4‐[(pyrimidin‐2‐ylazanidyl)sulfonyl]aniline, [C 5 H 7 N 2 ][SD], (V), and ethanolaminium 4‐[(pyrimidin‐2‐ylazanidyl)sulfonyl]aniline monohydrate, [HOCH 2 CH 2 NH 3 ][SD]·H 2 O, (VI), respectively. Structure (V) features a heterodimeric R 2 2 (8) hydrogen‐bond motif between the cation and the anion, whilst structure (VI) has a tetrameric core of two cations linked by a central R 2 2 (10) hydrogen‐bonded motif which supports two anions linked to this core by R 3 3 (8) motifs.