Crystal structure of bretylium tosylate (Bretylol®), C18H24BrNO3S

Wheatley, Austin M.; Kaduk, James A.; Gindhart, Amy M.; Blanton, Thomas N.

doi:10.1017/S088571561800060X

Crystal structure of bretylium tosylate (Bretylol®), C₁₈H₂₄BrNO₃S

Journal Article · Thu Sep 20 00:00:00 EDT 2018 · Powder Diffraction

DOI:https://doi.org/10.1017/S088571561800060X· OSTI ID:1484779

Wheatley, Austin M.; ; Gindhart, Amy M.; Blanton, Thomas N.

The crystal structure of bretylium tosylate has been solved and refined using synchrotron X-ray powder diffraction data, and optimized using density functional techniques. Bretylium tosylate crystallizes in space group C2/c(#15) with a= 32.6238(4), b= 12.40353(14),c= 9.93864(12) Å,β= 101.4676(10), V= 3941.39(5) Å³, and Z = 8. The sample exhibited visible decomposition in the X-ray beam. The unusual displacement ellipsoid of the Br atom probably indicates that the decomposition in the beam involves the Br atom. The crystal structure can be viewed as layered parallel to the bc plane. The layers are double, the center consisting of the cation/anion polar interactions and the outer surface of the double layers consists of hydrocarbon interactions. In the absence of normal hydrogen bond donors, the only hydrogen bonds in the bretylium tosylate structure are C–H…O hydrogen bonds. The powder pattern has been submitted to ICDD® for inclusion in the Powder Diffraction File™.

Research Organization:: Advanced Photon Source (APS), Argonne National Laboratory (ANL), Argonne, IL (US)

Sponsoring Organization:: INDUSTRY

OSTI ID:: 1484779

Journal Information:: Powder Diffraction, Journal Name: Powder Diffraction Journal Issue: 4 Vol. 33; ISSN 0885-7156

Publisher:: Cambridge University Press

Country of Publication:: United States

Language:: ENGLISH

References (23)

Consistent Gaussian basis sets of triple-zeta valence with polarization quality for solid-state calculations Peintinger, Michael F.; Oliveira, Daniel Vilela; Bredow, Thomas Journal of Computational Chemistry, Vol. 34, Issue 6 https://doi.org/10.1002/jcc.23153	journal	October 2012
Phenomenological model of anisotropic peak broadening in powder diffraction Stephens, Peter W. Journal of Applied Crystallography, Vol. 32, Issue 2 https://doi.org/10.1107/S0021889898006001	journal	April 1999
Bonded-atom fragments for describing molecular charge densities Hirshfeld, F. L. Theoretica Chimica Acta, Vol. 44, Issue 2 https://doi.org/10.1007/BF00549096	journal	January 1977
Hirshfeld surface analysis Spackman, Mark A.; Jayatilaka, Dylan CrystEngComm, Vol. 11, Issue 1 https://doi.org/10.1039/B818330A	journal	January 2009
Crystal field effects on the topological properties of the electron density in molecular crystals: The case of urea Gatti, C.; Saunders, V. R.; Roetti, C. The Journal of Chemical Physics, Vol. 101, Issue 12 https://doi.org/10.1063/1.467882	journal	December 1994
EXPO2013 : a kit of tools for phasing crystal structures from powder data Altomare, Angela; Cuocci, Corrado; Giacovazzo, Carmelo Journal of Applied Crystallography, Vol. 46, Issue 4 https://doi.org/10.1107/S0021889813013113	journal	July 2013
C RYSTAL14 : A program for the ab initio investigation of crystalline solids Dovesi, Roberto; Orlando, Roberto; Erba, Alessandro International Journal of Quantum Chemistry, Vol. 114, Issue 19 https://doi.org/10.1002/qua.24658	journal	March 2014
Rietveld refinement of Debye–Scherrer synchrotron X-ray data from Al ₂ O ₃ Thompson, P.; Cox, D. E.; Hastings, J. B. Journal of Applied Crystallography, Vol. 20, Issue 2 https://doi.org/10.1107/S0021889887087090	journal	April 1987
Retrieval of Crystallographically-Derived Molecular Geometry Information Bruno, Ian J.; Cole, Jason C.; Kessler, Magnus Journal of Chemical Information and Computer Sciences, Vol. 44, Issue 6 https://doi.org/10.1021/ci049780b	journal	November 2004
Validation of molecular crystal structures from powder diffraction data with dispersion-corrected density functional theory (DFT-D) van de Streek, Jacco; Neumann, Marcus A. Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials, Vol. 70, Issue 6, p. 1020-1032 https://doi.org/10.1107/S2052520614022902	journal	December 2014
Bretylium Tosylate Carter, James E.; Amann, Anton H.; Baaske, David M. Analytical Profiles of Drug Substances https://doi.org/10.1016/S0099-5428(08)60136-7	book	January 1981
FOX , `free objects for crystallography': a modular approach to ab initio structure determination from powder diffraction Favre-Nicolin, Vincent; Černý, Radovan Journal of Applied Crystallography, Vol. 35, Issue 6 https://doi.org/10.1107/S0021889802015236	journal	November 2002
Chemical analysis by diffraction: the Powder Diffraction File™ Fawcett, T. G.; Kabekkodu, S. N.; Blanton, J. R. Powder Diffraction, Vol. 32, Issue 2 https://doi.org/10.1017/S0885715617000288	journal	June 2017
DASH : a program for crystal structure determination from powder diffraction data David, William I. F.; Shankland, Kenneth; van de Streek, Jacco Journal of Applied Crystallography, Vol. 39, Issue 6 https://doi.org/10.1107/S0021889806042117	journal	November 2006
EXPGUI , a graphical user interface for GSAS Toby, Brian H. Journal of Applied Crystallography, Vol. 34, Issue 2 https://doi.org/10.1107/S0021889801002242	journal	April 2001
The Cambridge Structural Database Groom, Colin R.; Bruno, Ian J.; Lightfoot, Matthew P. Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials, Vol. 72, Issue 2, p. 171-179 https://doi.org/10.1107/S2052520616003954	journal	April 2016
Mercury CSD 2.0 – new features for the visualization and investigation of crystal structures Macrae, Clare F.; Bruno, Ian J.; Chisholm, James A. Journal of Applied Crystallography, Vol. 41, Issue 2 https://doi.org/10.1107/S0021889807067908	journal	March 2008
A twelve-analyzer detector system for high-resolution powder diffraction Lee, Peter L.; Shu, Deming; Ramanathan, Mohan Journal of Synchrotron Radiation, Vol. 15, Issue 5 https://doi.org/10.1107/S0909049508018438	journal	July 2008
A correction for powder diffraction peak asymmetry due to axial divergence Finger, L. W.; Cox, D. E.; Jephcoat, A. P. Journal of Applied Crystallography, Vol. 27, Issue 6 https://doi.org/10.1107/S0021889894004218	journal	December 1994
Novel tools for visualizing and exploring intermolecular interactions in molecular crystals McKinnon, Joshua J.; Spackman, Mark A.; Mitchell, Anthony S. Acta Crystallographica Section B Structural Science, Vol. 60, Issue 6 https://doi.org/10.1107/S0108768104020300	journal	November 2004
New software for statistical analysis of Cambridge Structural Database data Sykes, Richard A.; McCabe, Patrick; Allen, Frank H. Journal of Applied Crystallography, Vol. 44, Issue 4 https://doi.org/10.1107/S0021889811014622	journal	June 2011
A dedicated powder diffraction beamline at the Advanced Photon Source: Commissioning and early operational results Wang, Jun; Toby, Brian H.; Lee, Peter L. Review of Scientific Instruments, Vol. 79, Issue 8 https://doi.org/10.1063/1.2969260	journal	August 2008
Crystal structure of atomoxetine hydrochloride (Strattera), C ₁₇ H ₂₂ NOCl Kaduk, James A.; Crowder, Cyrus E.; Zhong, Kai Powder Diffraction, Vol. 29, Issue 3 https://doi.org/10.1017/S0885715614000517	journal	June 2014

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Crystal structure of bretylium tosylate (Bretylol®), C₁₈H₂₄BrNO₃S