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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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The asymmetric unit of the title compound, shown with 20% probability displacement ellipsoids. The O3—H3⋯Cl3 hydrogen bond is shown as an open bond.
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fig1: The asymmetric unit of the title compound, shown with 20% probability displacement ellipsoids. The O3—H3⋯Cl3 hydrogen bond is shown as an open bond.

Mentions: The asymmetric unit of [H(MET)][AuCl4] consists of a metronidazolium cation, [H(MET)]+, hydrogen-bonded to a square-planar tetra­chlorido­aurate(III) anion, [AuCl4]−, by an O—H⋯Cl hydrogen bond as illustrated in Fig. 1 ▸. The O3⋯Cl3 distance of 3.169 (2) Å is comparable to the values in other tetra­chlorido­aurate(III) derivatives that exhibit O—H⋯Cl hydrogen bonds. As an illustration, bis­{2-[(2-hy­droxy­eth­yl)imino­meth­yl]phenolato}gold(III) tetra­chlorido­aurate(III) possesses an O—H⋯Cl hydrogen bond between a hy­droxy­ethyl group and [AuCl4]−, with an O(H)⋯Cl distance of 3.365 Å (Nockemann et al., 2007 ▸). For further reference, the average O⋯Cl distance in compounds that have O—H⋯Cl inter­actions is 3.196 (3) Å (Steiner, 2002 ▸). The nitro group is almost coplanar with the imidazole ring, as indicated by an O1—N3—C2—C1 torsion angle of −0.2 (4)°, while the hy­droxy­ethyl group exhibits an O3—C6—C5—N2 torsion angle of 62.3 (3)°, describing a coiled conformation.


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

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

The asymmetric unit of the title compound, shown with 20% probability displacement ellipsoids. The O3—H3⋯Cl3 hydrogen bond is shown as an open bond.
© Copyright Policy - open-access
Related In: Results  -  Collection

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

fig1: The asymmetric unit of the title compound, shown with 20% probability displacement ellipsoids. The O3—H3⋯Cl3 hydrogen bond is shown as an open bond.
Mentions: The asymmetric unit of [H(MET)][AuCl4] consists of a metronidazolium cation, [H(MET)]+, hydrogen-bonded to a square-planar tetra­chlorido­aurate(III) anion, [AuCl4]−, by an O—H⋯Cl hydrogen bond as illustrated in Fig. 1 ▸. The O3⋯Cl3 distance of 3.169 (2) Å is comparable to the values in other tetra­chlorido­aurate(III) derivatives that exhibit O—H⋯Cl hydrogen bonds. As an illustration, bis­{2-[(2-hy­droxy­eth­yl)imino­meth­yl]phenolato}gold(III) tetra­chlorido­aurate(III) possesses an O—H⋯Cl hydrogen bond between a hy­droxy­ethyl group and [AuCl4]−, with an O(H)⋯Cl distance of 3.365 Å (Nockemann et al., 2007 ▸). For further reference, the average O⋯Cl distance in compounds that have O—H⋯Cl inter­actions is 3.196 (3) Å (Steiner, 2002 ▸). The nitro group is almost coplanar with the imidazole ring, as indicated by an O1—N3—C2—C1 torsion angle of −0.2 (4)°, while the hy­droxy­ethyl group exhibits an O3—C6—C5—N2 torsion angle of 62.3 (3)°, describing a coiled conformation.

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