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Crystal structure of ammonium 3'-azido-3'-de-oxy-thymidine-5'-amino-carbonyl-phospho-nate hemi-hydrate: an anti-HIV agent.

Jasko MV, Gurskaya GV, Kukhanova MK, Bushmarinov IS - Acta Crystallogr Sect E Struct Rep Online (2014)

Bottom Line: The asymmetric unit of the title compound, NH4 (+)·C11H14N6O7P(-)·0.5H2O, contains one 3'-azido-3'-de-oxy-thymidine-5'amino-carbonyl-phospho-nate (ACP-AZT) anion, half of an NH4 (+) cation lying on a twofold rotation axis and in another position, occupied with equal probabilities of 0.5, an NH4 (+) cation and a water mol-ecule.The pseudorotation parameters of ACP-AZT set it apart from previously studied AZT and thymidine.In the crystal, the various components are linked by N-H⋯O, O-H⋯O, N-H⋯N, C-H⋯O and C-H⋯N hydrogen bonds, forming a three-dimensional framework.

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Affiliation: Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, 119991, Vavilov St 32, Moscow, Russian Federation.

ABSTRACT
The asymmetric unit of the title compound, NH4 (+)·C11H14N6O7P(-)·0.5H2O, contains one 3'-azido-3'-de-oxy-thymidine-5'amino-carbonyl-phospho-nate (ACP-AZT) anion, half of an NH4 (+) cation lying on a twofold rotation axis and in another position, occupied with equal probabilities of 0.5, an NH4 (+) cation and a water mol-ecule. The amide group of the ACP-AZT anion is disordered (occupancy ratio 0.5:0.5), with one part forming an N-H⋯O (involving C=O⋯H4N(+)) hydrogen bond and the other an O-H⋯N (involving C-NH2⋯OH2) hydrogen bond with the components of the split NH4 (+)/H2O position. The pseudorotation parameters of ACP-AZT set it apart from previously studied AZT and thymidine. In the crystal, the various components are linked by N-H⋯O, O-H⋯O, N-H⋯N, C-H⋯O and C-H⋯N hydrogen bonds, forming a three-dimensional framework.

No MeSH data available.


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The hydrogen bonds involving the disordered water and ammonia mol­ecules in the crystal packing of ACP–AZT (see Table 1 ▶ for details). A fragment of the hypothetically ordered ‘supercell’ is shown.
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fig2: The hydrogen bonds involving the disordered water and ammonia mol­ecules in the crystal packing of ACP–AZT (see Table 1 ▶ for details). A fragment of the hypothetically ordered ‘supercell’ is shown.

Mentions: The C(O)NH2 group of ACP–AZT is disordered, one part forming a C=O⋯H4N+ hydrogen bond and the other a C—NH2⋯OH2 hydrogen bond with the components of the NH4+/H2O position (Table 1 ▶ and Fig. 2 ▶). In the crystal, the various components are linked by N—H⋯O, O—H⋯O, N—H⋯N, C—H⋯O and C—H⋯N hydrogen bonds (Table 1 ▶), forming a three-dimensional framework. The structure can be described by an ordered supercell doubled in the c direction (Fig. 2 ▶); however, this was not observed in the diffraction experiment.


Crystal structure of ammonium 3'-azido-3'-de-oxy-thymidine-5'-amino-carbonyl-phospho-nate hemi-hydrate: an anti-HIV agent.

Jasko MV, Gurskaya GV, Kukhanova MK, Bushmarinov IS - Acta Crystallogr Sect E Struct Rep Online (2014)

The hydrogen bonds involving the disordered water and ammonia mol­ecules in the crystal packing of ACP–AZT (see Table 1 ▶ for details). A fragment of the hypothetically ordered ‘supercell’ is shown.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4257306&req=5

fig2: The hydrogen bonds involving the disordered water and ammonia mol­ecules in the crystal packing of ACP–AZT (see Table 1 ▶ for details). A fragment of the hypothetically ordered ‘supercell’ is shown.
Mentions: The C(O)NH2 group of ACP–AZT is disordered, one part forming a C=O⋯H4N+ hydrogen bond and the other a C—NH2⋯OH2 hydrogen bond with the components of the NH4+/H2O position (Table 1 ▶ and Fig. 2 ▶). In the crystal, the various components are linked by N—H⋯O, O—H⋯O, N—H⋯N, C—H⋯O and C—H⋯N hydrogen bonds (Table 1 ▶), forming a three-dimensional framework. The structure can be described by an ordered supercell doubled in the c direction (Fig. 2 ▶); however, this was not observed in the diffraction experiment.

Bottom Line: The asymmetric unit of the title compound, NH4 (+)·C11H14N6O7P(-)·0.5H2O, contains one 3'-azido-3'-de-oxy-thymidine-5'amino-carbonyl-phospho-nate (ACP-AZT) anion, half of an NH4 (+) cation lying on a twofold rotation axis and in another position, occupied with equal probabilities of 0.5, an NH4 (+) cation and a water mol-ecule.The pseudorotation parameters of ACP-AZT set it apart from previously studied AZT and thymidine.In the crystal, the various components are linked by N-H⋯O, O-H⋯O, N-H⋯N, C-H⋯O and C-H⋯N hydrogen bonds, forming a three-dimensional framework.

View Article: PubMed Central - HTML - PubMed

Affiliation: Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, 119991, Vavilov St 32, Moscow, Russian Federation.

ABSTRACT
The asymmetric unit of the title compound, NH4 (+)·C11H14N6O7P(-)·0.5H2O, contains one 3'-azido-3'-de-oxy-thymidine-5'amino-carbonyl-phospho-nate (ACP-AZT) anion, half of an NH4 (+) cation lying on a twofold rotation axis and in another position, occupied with equal probabilities of 0.5, an NH4 (+) cation and a water mol-ecule. The amide group of the ACP-AZT anion is disordered (occupancy ratio 0.5:0.5), with one part forming an N-H⋯O (involving C=O⋯H4N(+)) hydrogen bond and the other an O-H⋯N (involving C-NH2⋯OH2) hydrogen bond with the components of the split NH4 (+)/H2O position. The pseudorotation parameters of ACP-AZT set it apart from previously studied AZT and thymidine. In the crystal, the various components are linked by N-H⋯O, O-H⋯O, N-H⋯N, C-H⋯O and C-H⋯N hydrogen bonds, forming a three-dimensional framework.

No MeSH data available.


Related in: MedlinePlus