Salt forms of sulfadiazine with alkali metal and organic cations

Gemma Campbell, Rebecca Fisher, Alan R. Kennedy, Nathan L. C. King, Rebecca Spiteri

Research output: Contribution to journalArticle

Abstract

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.
LanguageEnglish
Pages472-479
Number of pages8
JournalActa Crystallographica Section C: Structural Chemistry
Volume74
Issue number4
DOIs
Publication statusPublished - 15 Mar 2018

Fingerprint

Alkali Metals
Sulfadiazine
Alkali metals
alkali metals
Anions
Cations
Negative ions
Salts
Positive ions
anions
salts
cations
coordination polymers
Polymers
Ethanolamines
Hydrazones
Naphthols
Naphthol
hydrazones
Ethanolamine

Keywords

  • crystal structure
  • active pharmaceutical ingredients
  • salt selection
  • sulfadiazine
  • sulfa drugs

Cite this

Campbell, Gemma ; Fisher, Rebecca ; Kennedy, Alan R. ; King, Nathan L. C. ; Spiteri, Rebecca. / Salt forms of sulfadiazine with alkali metal and organic cations. In: Acta Crystallographica Section C: Structural Chemistry. 2018 ; Vol. 74, No. 4. pp. 472-479.
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abstract = "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.",
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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 journalArticle

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 -