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Crystal structure of (4R,5S,6R)-6-azido-5-benz-yloxy-3,3,4-tri-fluoro-azepan-1-ium 2,2,2-tri-fluoro-acetate from synchrotron data.

Patel AR, Bhadbhade MM, Liu F - Acta Crystallogr E Crystallogr Commun (2015)

Bottom Line: The seven-membered rings adopt different conformations with the principal differences occurring in the CF2CHFCH2 segments of the ring systems.The geminal F atoms on the quaternary C atom exhibit essentially identical bond angles [109 (2) and 106 (2)°] in the two independent mol-ecules.The two mol-ecules associate as a dimeric unit via two C-H⋯F inter-actions.

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Affiliation: Department of Chemistry and Biomolecular Sciences, Macquarie University, Sydney, NSW 2109, Australia.

ABSTRACT
The structure of the title compound, C15H16F6N4O3, was determined using synchrotron radiation on an extremely small crystal (0.015 × 0.01 × 0.01 mm). Although the diffraction was weak, leading to high residuals and a poor data-to-parameter ratio, the data allowed ready solution and refinement to reveal the entire structure. The solid-state structure is in accordance with the absolute configuration assigned based on that of the known starting material. The compound comprises a highly substituted seven-membered N-heterocyclic cation and a tri-fluoro-methane-sulfonate counter-anion. The title compound crystallizes with two independent cations (A and B) and anions (C and D) in the asymmetric unit. Two geminal F atoms, a single F atom, a benzyl ether and an azide group are substituted on consecutive C atoms between the NH2 and CH2 units of the azepan-1-ium ring system. The seven-membered rings adopt different conformations with the principal differences occurring in the CF2CHFCH2 segments of the ring systems. The geminal F atoms on the quaternary C atom exhibit essentially identical bond angles [109 (2) and 106 (2)°] in the two independent mol-ecules. The two mol-ecules associate as a dimeric unit via two C-H⋯F inter-actions. An extensive series of N-H⋯O, N-H⋯F, C-H⋯O, C-H⋯N, C-H⋯F and C-H⋯π contacts generate a three-dimensional network with cations and anions linked into ABCD repeat columns along a.

No MeSH data available.


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Conformations and torsion angles of the seven-membered rings of mol­ecules A and B.
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fig3: Conformations and torsion angles of the seven-membered rings of mol­ecules A and B.

Mentions: The two mol­ecules differ significantly in their seven-membered ring conformations, in particular around C2 and C3 with significantly different torsion angles, Fig. 3 ▸, where the mol­ecules are involved in making dimeric contacts. Torsion angles within the two rings are shown in Fig. 3 ▸.


Crystal structure of (4R,5S,6R)-6-azido-5-benz-yloxy-3,3,4-tri-fluoro-azepan-1-ium 2,2,2-tri-fluoro-acetate from synchrotron data.

Patel AR, Bhadbhade MM, Liu F - Acta Crystallogr E Crystallogr Commun (2015)

Conformations and torsion angles of the seven-membered rings of mol­ecules A and B.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4645019&req=5

fig3: Conformations and torsion angles of the seven-membered rings of mol­ecules A and B.
Mentions: The two mol­ecules differ significantly in their seven-membered ring conformations, in particular around C2 and C3 with significantly different torsion angles, Fig. 3 ▸, where the mol­ecules are involved in making dimeric contacts. Torsion angles within the two rings are shown in Fig. 3 ▸.

Bottom Line: The seven-membered rings adopt different conformations with the principal differences occurring in the CF2CHFCH2 segments of the ring systems.The geminal F atoms on the quaternary C atom exhibit essentially identical bond angles [109 (2) and 106 (2)°] in the two independent mol-ecules.The two mol-ecules associate as a dimeric unit via two C-H⋯F inter-actions.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry and Biomolecular Sciences, Macquarie University, Sydney, NSW 2109, Australia.

ABSTRACT
The structure of the title compound, C15H16F6N4O3, was determined using synchrotron radiation on an extremely small crystal (0.015 × 0.01 × 0.01 mm). Although the diffraction was weak, leading to high residuals and a poor data-to-parameter ratio, the data allowed ready solution and refinement to reveal the entire structure. The solid-state structure is in accordance with the absolute configuration assigned based on that of the known starting material. The compound comprises a highly substituted seven-membered N-heterocyclic cation and a tri-fluoro-methane-sulfonate counter-anion. The title compound crystallizes with two independent cations (A and B) and anions (C and D) in the asymmetric unit. Two geminal F atoms, a single F atom, a benzyl ether and an azide group are substituted on consecutive C atoms between the NH2 and CH2 units of the azepan-1-ium ring system. The seven-membered rings adopt different conformations with the principal differences occurring in the CF2CHFCH2 segments of the ring systems. The geminal F atoms on the quaternary C atom exhibit essentially identical bond angles [109 (2) and 106 (2)°] in the two independent mol-ecules. The two mol-ecules associate as a dimeric unit via two C-H⋯F inter-actions. An extensive series of N-H⋯O, N-H⋯F, C-H⋯O, C-H⋯N, C-H⋯F and C-H⋯π contacts generate a three-dimensional network with cations and anions linked into ABCD repeat columns along a.

No MeSH data available.


Related in: MedlinePlus