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Crystal structure of metronidazolium tetra-chlorido-aurate(III).

Quinlivan PJ, Wu JS, Upmacis RK - Acta Crystallogr E Crystallogr Commun (2015)

Bottom Line: In the cation, the nitro group is essentially coplanar with the imidazole ring, as indicated by an O N-C=C torsion angle of -0.2 (4)°, while the hy-droxy-ethyl group is in a coiled conformation, with an O(H)-C-C-N torsion angle of 62.3 (3)°.In the crystal, the anion and cation are linked by an inter-molecular O-H⋯Cl hydrogen bond.In addition, the N-H group of the metronidazolium ion serves as a hydrogen-bond donor to the O atom of the hy-droxy-ethyl group of a symmetry-related mol-ecule, leading to the formation of chains along [010].

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry, Columbia University, New York, NY 10027, USA.

ABSTRACT
Metronidazole (MET) [systematic names: 1-(2-hy-droxy-eth-yl)-2-methyl-5-nitro-1H-imidazole and 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethanol] is a medication that is used to treat infections from a variety of anaerobic organisms. As with other imidazole derivatives, metronidazole is also susceptible to protonation. However, there are few reports of the structures of metronidazolium derivatives. In the title compound, (C6H10N3O3)[AuCl4] [systematic name: 1-(2-hy-droxy-eth-yl)-2-methyl-5-nitro-1H-imidazol-3-ium tetra-chlorido-aur-ate(III)], the asymmetric unit consists of a metronidazolium cation, [H(MET)](+), and a tetra-chlorido-aurate(III) anion, [AuCl4](-), in which the Au(III) ion is in a slightly distorted square-planar coordination environment. In the cation, the nitro group is essentially coplanar with the imidazole ring, as indicated by an O N-C=C torsion angle of -0.2 (4)°, while the hy-droxy-ethyl group is in a coiled conformation, with an O(H)-C-C-N torsion angle of 62.3 (3)°. In the crystal, the anion and cation are linked by an inter-molecular O-H⋯Cl hydrogen bond. In addition, the N-H group of the metronidazolium ion serves as a hydrogen-bond donor to the O atom of the hy-droxy-ethyl group of a symmetry-related mol-ecule, leading to the formation of chains along [010].

No MeSH data available.


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Part of the crystal structure showing a hydrogen-bonded chain (open bonds) along [010].
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fig2: Part of the crystal structure showing a hydrogen-bonded chain (open bonds) along [010].

Mentions: In the crystal, the N—H group of the metronidazolium ion serves as a hydrogen-bond donor to the oxygen atom of the hy­droxy­ethyl group of a symmetry-related mol­ecule, forming a chain along [010] in which each O—H group is O—H⋯Cl hydrogen bonded to a [AuCl4]− ion (Table 1 ▸ and Fig. 2 ▸). The N⋯O distance of 2.729 (3) Å associated with the hydrogen bond is comparable to that observed for metronidazole [2.816 (2) Å] (Blaton et al., 1979 ▸; Galván-Tejada et al., 2002 ▸). However, an important difference between the hydrogen bonds in metronidazole and metronidazolium is that the alcohol O—H group is the hydrogen-bond donor for metronidazole (i.e. O—H⋯N), while the N—H group is the hydrogen-bond donor for metronidazolium (i.e. N—H⋯O).


Crystal structure of metronidazolium tetra-chlorido-aurate(III).

Quinlivan PJ, Wu JS, Upmacis RK - Acta Crystallogr E Crystallogr Commun (2015)

Part of the crystal structure showing a hydrogen-bonded chain (open bonds) along [010].
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4518979&req=5

fig2: Part of the crystal structure showing a hydrogen-bonded chain (open bonds) along [010].
Mentions: In the crystal, the N—H group of the metronidazolium ion serves as a hydrogen-bond donor to the oxygen atom of the hy­droxy­ethyl group of a symmetry-related mol­ecule, forming a chain along [010] in which each O—H group is O—H⋯Cl hydrogen bonded to a [AuCl4]− ion (Table 1 ▸ and Fig. 2 ▸). The N⋯O distance of 2.729 (3) Å associated with the hydrogen bond is comparable to that observed for metronidazole [2.816 (2) Å] (Blaton et al., 1979 ▸; Galván-Tejada et al., 2002 ▸). However, an important difference between the hydrogen bonds in metronidazole and metronidazolium is that the alcohol O—H group is the hydrogen-bond donor for metronidazole (i.e. O—H⋯N), while the N—H group is the hydrogen-bond donor for metronidazolium (i.e. N—H⋯O).

Bottom Line: In the cation, the nitro group is essentially coplanar with the imidazole ring, as indicated by an O N-C=C torsion angle of -0.2 (4)°, while the hy-droxy-ethyl group is in a coiled conformation, with an O(H)-C-C-N torsion angle of 62.3 (3)°.In the crystal, the anion and cation are linked by an inter-molecular O-H⋯Cl hydrogen bond.In addition, the N-H group of the metronidazolium ion serves as a hydrogen-bond donor to the O atom of the hy-droxy-ethyl group of a symmetry-related mol-ecule, leading to the formation of chains along [010].

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry, Columbia University, New York, NY 10027, USA.

ABSTRACT
Metronidazole (MET) [systematic names: 1-(2-hy-droxy-eth-yl)-2-methyl-5-nitro-1H-imidazole and 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethanol] is a medication that is used to treat infections from a variety of anaerobic organisms. As with other imidazole derivatives, metronidazole is also susceptible to protonation. However, there are few reports of the structures of metronidazolium derivatives. In the title compound, (C6H10N3O3)[AuCl4] [systematic name: 1-(2-hy-droxy-eth-yl)-2-methyl-5-nitro-1H-imidazol-3-ium tetra-chlorido-aur-ate(III)], the asymmetric unit consists of a metronidazolium cation, [H(MET)](+), and a tetra-chlorido-aurate(III) anion, [AuCl4](-), in which the Au(III) ion is in a slightly distorted square-planar coordination environment. In the cation, the nitro group is essentially coplanar with the imidazole ring, as indicated by an O N-C=C torsion angle of -0.2 (4)°, while the hy-droxy-ethyl group is in a coiled conformation, with an O(H)-C-C-N torsion angle of 62.3 (3)°. In the crystal, the anion and cation are linked by an inter-molecular O-H⋯Cl hydrogen bond. In addition, the N-H group of the metronidazolium ion serves as a hydrogen-bond donor to the O atom of the hy-droxy-ethyl group of a symmetry-related mol-ecule, leading to the formation of chains along [010].

No MeSH data available.


Related in: MedlinePlus