Abstract
Language | English |
---|---|
Pages | 472-479 |
Number of pages | 8 |
Journal | Acta Crystallographica Section C: Structural Chemistry |
Volume | 74 |
Issue number | 4 |
DOIs | |
Publication status | Published - 15 Mar 2018 |
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Keywords
- crystal structure
- active pharmaceutical ingredients
- salt selection
- sulfadiazine
- sulfa drugs
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Salt forms of sulfadiazine with alkali metal and organic cations. / Campbell, Gemma; Fisher, Rebecca; Kennedy, Alan R.; King, Nathan L. C.; Spiteri, Rebecca.
In: Acta Crystallographica Section C: Structural Chemistry, Vol. 74, No. 4, 15.03.2018, p. 472-479.Research output: Contribution to journal › Article
TY - JOUR
T1 - Salt forms of sulfadiazine with alkali metal and organic cations
AU - Campbell, Gemma
AU - Fisher, Rebecca
AU - Kennedy, Alan R.
AU - King, Nathan L. C.
AU - Spiteri, Rebecca
PY - 2018/3/15
Y1 - 2018/3/15
N2 - The structures of four salt forms of sulfadiazine (SDH) with alkali metal cations are presented. Three contain the deprotonated SD anion. These are the discrete complex [Li(SD)(OH2)2], (I), and the coordination polymers [Na(SD)]n, (II), and [K(SD)(OH2)2]n, (III). The Na complex (II) is a three-dimensional coordination polymer whilst the K complex (III) has two crystallographically independent [K(SD)(OH2)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 SDH2 cations and the Orange G (OG), C16H10N2O7S2, dianion in a structure with formula [SDH2]2[Na(OG)(OH2)4]2·3H2O. The [Na(OG)(OH2)4]2 dimers have antiparallel naphthol 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 [C5H7N2][SD], (V), and [HOCH2CH2NH3][SD]·H2O, (VI), respectively. Structure (V) features a heterodimeric R2 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 R2 2(10) hydrogen bonded motif which supports two anions linked to this core by R3 3(8) motifs.
AB - The structures of four salt forms of sulfadiazine (SDH) with alkali metal cations are presented. Three contain the deprotonated SD anion. These are the discrete complex [Li(SD)(OH2)2], (I), and the coordination polymers [Na(SD)]n, (II), and [K(SD)(OH2)2]n, (III). The Na complex (II) is a three-dimensional coordination polymer whilst the K complex (III) has two crystallographically independent [K(SD)(OH2)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 SDH2 cations and the Orange G (OG), C16H10N2O7S2, dianion in a structure with formula [SDH2]2[Na(OG)(OH2)4]2·3H2O. The [Na(OG)(OH2)4]2 dimers have antiparallel naphthol 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 [C5H7N2][SD], (V), and [HOCH2CH2NH3][SD]·H2O, (VI), respectively. Structure (V) features a heterodimeric R2 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 R2 2(10) hydrogen bonded motif which supports two anions linked to this core by R3 3(8) motifs.
KW - crystal structure
KW - active pharmaceutical ingredients
KW - salt selection
KW - sulfadiazine
KW - sulfa drugs
UR - http://onlinelibrary.wiley.com/journal/10.1107/S20532296
U2 - 10.1107/S205322961800414
DO - 10.1107/S205322961800414
M3 - Article
VL - 74
SP - 472
EP - 479
JO - Acta Crystallographica Section C: Structural Chemistry
T2 - Acta Crystallographica Section C: Structural Chemistry
JF - Acta Crystallographica Section C: Structural Chemistry
SN - 2053-2296
IS - 4
ER -