Racemic mefloquinium chloro-difluoro-acetate: crystal structure and Hirshfeld surface analysis

Acta Crystallographica. Section E, Crystallographic Communications
James L WardellEdward R T Tiekink

Abstract

In the racemic title mol-ecular salt, C17H17F6N2O+·C2ClF2O3- (systematic name: 2-{[2,8-bis-(tri-fluoro-meth-yl)quinolin-4-yl](hy-droxy)meth-yl}piperidin-1-ium chloro-difluoro-acetate), the cation, which is protonated at the piperidine N atom, has the shape of the letter, L, with the piperidin-1-ium group being approximately orthogonal to the quinolinyl residue [the Cq-Cm-Cm-Na (q = quinolinyl; m = methine; a = ammonium) torsion angle is 177.79 (18)°]. An intra-molecular, charge-assisted ammonium-N-H⋯O(hydrox-yl) hydrogen bond ensures the hy-droxy-O and ammonium-N atoms lie to the same side of the mol-ecule [Oh-Cm-Cm-Na (h = hydrox-yl) = -59.7 (2)°]. In the crystal, charge-assisted hydroxyl-O-H⋯O-(carboxyl-ate) and ammonium-N+-H⋯O-(carboxyl-ate) hydrogen bonds generate a supra-molecular chain along [010]; the chain is consolidated by C-H⋯O inter-actions. Links between chains to form supra-molecular layers are of the type C-Cl⋯π(quinolinyl-C6) and the layers thus formed stack along the a-axis direction without directional inter-actions between them. The analysis of the calculated Hirshfeld surface points to the dominance of F⋯H contacts to the surface (40.8%) with significant contributions from F⋯F (10.5%) and C⋯F (7.0%) contacts.

References

Apr 1, 2006·Clinical Infectious Diseases : an Official Publication of the Infectious Diseases Society of America·Jason D MaguireJ Kevin Baird
Dec 25, 2007·Acta Crystallographica. Section A, Foundations of Crystallography·George M Sheldrick
Jan 26, 2008·Chemical Communications : Chem Comm·Joshua J McKinnonMark A Spackman
Jan 27, 2010·Acta Crystallographica. Section B, Structural Science·László Fábián, Carolyn Pratt Brock
Aug 22, 2013·Chemical Biology & Drug Design·Felipe A R RodriguesMarcus V N de Souza
Jan 9, 2015·Acta Crystallographica. Section C, Structural Chemistry·George M Sheldrick
Mar 4, 2015·Acta Crystallographica. Section C, Structural Chemistry·Ivan Bernal, Steven Watkins
Apr 7, 2016·Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials·Colin R GroomSuzanna C Ward
Jun 17, 2016·Acta Crystallographica. Section E, Crystallographic Communications·James L WardellEdward R T Tiekink
Nov 15, 2016·Acta Crystallographica. Section E, Crystallographic Communications·James L WardellEdward R T Tiekink

❮ Previous
Next ❯

Citations

Dec 24, 2018·Acta Crystallographica. Section E, Crystallographic Communications·James L WardellEdward R T Tiekink
Aug 17, 2019·Acta Crystallographica. Section E, Crystallographic Communications·James L WardellEdward R T Tiekink

❮ Previous
Next ❯

Methods Mentioned

BETA
NMR

Software Mentioned

CrystalExplorer3

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.

Related Papers

Acta Crystallographica. Section E, Structure Reports Online
Xiang-Xiang WuEdward R T Tiekink
Acta Crystallographica. Section E, Crystallographic Communications
Bhai R DevikaEdward R T Tiekink
Acta Crystallographica. Section E, Crystallographic Communications
Junita JamsariEdward R T Tiekink
© 2022 Meta ULC. All rights reserved