Skip to main content Accessibility help
×
Home

Crystal structure of citalopram hydrobromide, C20H22FN2OBr

  • James A. Kaduk (a1), Kai Zhong (a2), Amy M. Gindhart (a2) and Thomas N. Blanton (a2)

Abstract

The crystal structure of citalopram hydrobromide has been solved and refined using synchrotron X-ray powder diffraction data, and optimized using density functional theory techniques. Citalopram hydrobromide crystallizes in space group P21/c (#14) with a = 10.766 45(6), b = 33.070 86(16), c = 10.892 85(5) Å, β = 90.8518(3)°, V = 3878.03(4) Å3, and Z = 8. N–H⋯Br hydrogen bonds are important to the structure, but the crystal energy is dominated by van der Waals attraction. The powder pattern was submitted to International Centre for Diffraction Data for inclusion in the Powder Diffraction File™.

Copyright

Corresponding author

a) Author to whom correspondence should be addressed. Electronic mail: kaduk@polycrystallography.com

References

Hide All
Allen, F. H. (2002). “The Cambridge Structural Database: a quarter of a million crystal structures and rising,” Acta Crystallogr. Sect. B: Struct. Sci. 58, 380388.
Altomare, A., Cuocci, C., Giacovazzo, C., Moliterni, A., Rizzi, R., Corriero, N., and Falcicchio, A. (2013). “EXPO2013: a kit of tools for phasing crystal structures from powder data”, J. Appl. Crystallogr. 46, 12311235.
Bernstein, J., Davis, R. E., Shimoni, L., and Chang, N. L. (1995). “Patterns in hydrogen bonding: functionality and graph set analysis in crystals,” Angew. Chem. Int. Ed. Engl. 34(15), 15551573.
Bogeso, K. P. and Lundbeck, H. (1987). “Novel Intermediate and Method for Its Preparation,” US Patent 4,650,884.
Bravais, A. (1866). Etudes Cristallographiques (Gauthier Villars, Paris).
Bruno, I. J., Cole, J. C., Kessler, M., Luo, J., Motherwell, W. D. S., Purkis, L. H., Smith, B. R., Taylor, R., Cooper, R. I., Harris, S. E., and Orpen, A. G. (2004). “Retrieval of crystallographically-derived molecular geometry information,” J. Chem. Inf. Sci. 44, 21332144.
Dassault Systèmes (2014). Materials Studio 8.0 (BIOVIA, San Diego, CA).
David, W. I. F., Shankland, K., van de Streek, J., Pidcock, E., Motherwell, W. D. S., and Cole, J. C. (2006). “DASH: a program for crystal structure determination from powder diffraction data,” J. Appl. Crystallogr. 39, 910915.
de Diego, H. L., Bond, A. D., and Dancer, R. J. (2011). “Formation of solid solutions between racemic and enantiomeric citalopram oxalate,” Chirality 23(5), 408416.
Donnay, J. D. H. and Harker, D. (1937). “A new law of crystal morphology extending the law of Bravais,” Amer. Mineral. 22, 446467.
Dovesi, R., Orlando, R., Civalleri, B., Roetti, C., Saunders, V. R., and Zicovich-Wilson, C. M. (2005). “CRYSTAL: a computational tool for the ab initio study of the electronic properties of crystals,” Z. Kristallogr. 220, 571573.
Etter, M. C. (1990). “Encoding and decoding hydrogen-bond patterns of organic compounds,” Acc. Chem. Res. 23(4), 120126.
Finger, L. W., Cox, D. E., and Jephcoat, A. P. (1994). “A correction for powder diffraction peak asymmetry due to axial divergence,” J. Appl. Crystallogr. 27(6), 892900.
Friedel, G. (1907). “Etudes sur la loi de Bravais,” Bull. Soc. Fr. Mineral. 30, 326455.
Gatti, C., Saunders, V. R., and Roetti, C. (1994). “Crystal-field effects on the topological properties of the electron-density in molecular crystals – the case of urea,” J. Chem. Phys. 101, 1068610696.
Harrison, W. T., Yathirajan, H. S., Bindya, S., and Anilkumar, H. G. (2007). “Escitalopram oxalate: co-existence of oxalate dianions and oxalic acid molecules in the same crystal,” Acta Crystallogr. Sect. C: Crystal Struct. Commun. 63(2), o129o131.
Hirshfeld, F. L. (1977). “Bonded-atom fragments for describing molecular charge densities,” Theor. Chem. Acta 44, 129138.
ICDD (2015), PDF-4+ 2014 (Database), edited by Dr. Soorya Kabekkodu, International Centre for Diffraction Data, Newtown Square, PA, USA.
Ikemoto, T., Arai, N., and Igi, M. (2001). “Citalopram hydrobromide crystal and method for crystallization thereof,” European Patent Application EP 1,152,000.
Larson, A. C. and Von Dreele, R. B. (2004). General Structure Analysis System, (GSAS), (Los Alamos National Laboratory Report LAUR 86-784).
Lee, P. L., Shu, D., Ramanathan, M., Preissner, C., Wang, J., Beno, M. A., Von Dreele, R. B., Ribaud, L., Kurtz, C., Antao, S. M., Jiao, X., and Toby, B. H. (2008). “A twelve-analyzer detector system for high-resolution powder diffraction,” J. Synchroton Radiat. 15(5), 427432.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J., and Wood, P. A. (2008). “Mercury CSD 2.0 – new features for the visualization and investigation of crystal structures,” J. Appl. Crystallogr. 41, 466470.
McKinnon, J. J., Spackman, M. A., and Mitchell, A. S. (2004). “Novel tools for visualizing and exploring intermolecular interactions in molecular crystals,” Acta Crystallogr. Sect. B: Struct. Sci. 60, 627668.
Nada, R., Catlow, C. R. A., Pisani, C., and Orlando, R. (1993). “Ab initio Hartree-Fock perturbed-cluster study of neutral defects in LiF,” Model. Simul. Mater. Sci. Eng. 1, 165187.
O'Boyle, N., Banck, M., James, C. A., Morley, C., Vandermeersch, , and Hutchison, G. R. (2011). “Open babel: an open chemical toolbox,” J. Chem. Inf., 3, 33. doi: 10.1186/1758-2946-3-33.
Peintinger, M. F., Vilela Oliveira, D., and Bredow, T. (2012). “Consistent gaussian basis sets of triple-zeta valence with polarization quality for solid-state calculations,” J. Comput. Chem. 34(6), 451459. doi: 10.1002/jcc.23153
Shields, G. P., Raithby, P. R., Allen, F. H., and Motherwell, W. S. (2000). “The assignment and validation of metal oxidation states in the Cambridge Structural Database,” Acta Crystallogr. Sect. B: Struct. Sci. 56(3), 455465.
Spackman, M. A. and Jayatilaka, D. (2009). “Hirshfeld surface analysis,” CrystEngComm 11, 1932.
Stephens, P. W. (1999). “Phenomenological model of anisotropic peak broadening in powder diffraction,” J. Appl. Crystallogr. 32, 281289.
Sykes, R. A., McCabe, P., Allen, F. H., Battle, G. M., Bruno, I. J., and Wood, P. A. (2011). “New software for statistical analysis of Cambridge Structural Database data,” J. Appl. Crystallogr. 44, 882886.
Thompson, P., Cox, D. E., and Hastings, J. B. (1987). “Rietveld refinement of Debye–Scherrer synchrotron X-ray data from Al2O3 ,” J. Appl. Crystallogr. 20(2), 7983.
Toby, B. H. (2001). “EXPGUI, a graphical user interface for GSAS,” J. Appl. Crystallogr. 34, 210213.
van de Streek, J. and Neumann, M. A. (2014). “Validation of molecular crystal structures from powder diffraction data with dispersion-corrected density functional theory (DFT-D),” Acta Crystallogr. Sect. B: Struct. Sci. 70(6), 10201032.
Wang, J., Toby, B. H., Lee, P. L., Ribaud, L., Antao, S. M., Kurtz, C., Ramanathan, M., Von Dreele, R. B., and Beno, M. A. (2008). “A dedicated powder diffraction beamline at the Advanced Photon Source: commissioning and early operational results,” Rev. Sci. Instrum. 79, 085105.
Wavefunction, Inc. (2013). Spartan ‘14 Version 1.1.0, Wavefunction Inc., 18401 Von Karman Ave., Suite 370, Irvine CA 92612.
Wolff, S. K., Grimwood, D. J., McKinnon, M. J., Turner, M. J., Jayatilaka, D., and Spackman, M. A. (2012). CrystalExplorer Version 3.1 (University of Western Australia).

Keywords

Related content

Powered by UNSILO
Type Description Title
UNKNOWN
Supplementary materials

Kaduk supplementary material
Kaduk supplementary material 1

 Unknown (45 KB)
45 KB
UNKNOWN
Supplementary materials

Kaduk supplementary material
Kaduk supplementary material 2

 Unknown (662 KB)
662 KB
UNKNOWN
Supplementary materials

Kaduk supplementary material
Kaduk supplementary material 3

 Unknown (12 KB)
12 KB

Crystal structure of citalopram hydrobromide, C20H22FN2OBr

  • James A. Kaduk (a1), Kai Zhong (a2), Amy M. Gindhart (a2) and Thomas N. Blanton (a2)

Metrics

Full text views

Total number of HTML views: 0
Total number of PDF views: 0 *
Loading metrics...

Abstract views

Total abstract views: 0 *
Loading metrics...

* Views captured on Cambridge Core between <date>. This data will be updated every 24 hours.

Usage data cannot currently be displayed.