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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.

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

A view of the complete asymmetric unit consisting of two mol­ecules of (1) and two tri­fluoro­methane­sulfonate anions. In this and subsequent figures, hydrogen bonds are drawn as dashed lines.
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fig2: A view of the complete asymmetric unit consisting of two mol­ecules of (1) and two tri­fluoro­methane­sulfonate anions. In this and subsequent figures, hydrogen bonds are drawn as dashed lines.

Mentions: An alternative ORTEP view, Fig. 2 ▸, shows the asymmetric unit with association between A and B mol­ecules via two C—H⋯F inter­actions to form dimers. The asymmetric unit is completed by the two triflate anions C and D. These are variously linked in an A to C and B to D fashion by N—H⋯O, N—H⋯F, C—H⋯O and C—H⋯F hydrogen bonds, Table 1 ▸.


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)

A view of the complete asymmetric unit consisting of two mol­ecules of (1) and two tri­fluoro­methane­sulfonate anions. In this and subsequent figures, hydrogen bonds are drawn as dashed lines.
© Copyright Policy - open-access
Related In: Results  -  Collection

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

fig2: A view of the complete asymmetric unit consisting of two mol­ecules of (1) and two tri­fluoro­methane­sulfonate anions. In this and subsequent figures, hydrogen bonds are drawn as dashed lines.
Mentions: An alternative ORTEP view, Fig. 2 ▸, shows the asymmetric unit with association between A and B mol­ecules via two C—H⋯F inter­actions to form dimers. The asymmetric unit is completed by the two triflate anions C and D. These are variously linked in an A to C and B to D fashion by N—H⋯O, N—H⋯F, C—H⋯O and C—H⋯F hydrogen bonds, Table 1 ▸.

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