Skip to main content Accessibility help
×
Home

Crystal structure of terazosin hydrochloride dihydrate (Hytrin®), C19H26N5O4Cl(H2O)2

  • Austin M. Wheatley (a1), James A. Kaduk (a1) (a2), Martin Vickers (a3), Amy M. Gindhart (a4), Joseph G. Sunzeri (a4) and Thomas N. Blanton (a4)...

Abstract

The crystal structure of terazosin hydrochloride dihydrate has been solved and refined using synchrotron X-ray powder diffraction data, and optimized using density functional techniques. Terazosin hydrochloride dihydrate crystallizes in space group P-1 (#2) with a = 10.01402(4), b = 10.89995(4), c = 11.85357(4) Å, α = 89.5030(3), β = 71.8503(3), γ = 66.5632(2)°, V = 1118.143(8) Å3, and Z = 2. The terazosin cation occurs in an extended conformation. The crystal structure is dominated by hydrogen bonds. The most notable are the O–H···Cl from the water molecules to the chloride anion and N–H···Cl from the protonated ring nitrogen to the chloride. The amino group donates protons to each of the two water molecules. The powder pattern has been submitted to ICDD® 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
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.
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.
Cannata, V., Ferrario, T., and Galbiati, B. (1999). “Process for the Production of the Form I of the Terazosin Monohydrochloride Anhydrous,” US Patent 5856482 (ALFA Chemicals Italiana S.R.L.).
Dassault Systèmes (2016). Materials Studio 2017R2 (BIOVIA, San Diego, CA).
Donnay, J. D. H. and Harker, D. (1937). “A new law of crystal morphology extending the law of Bravais,” Am. Mineral. 22, 446447.
Dovesi, R., Orlando, R., Erba, A., Zicovich-Wilson, C. M., Civalleri, B., Casassa, S., Maschio, L., Ferrabone, M., De La Pierre, M., D-Arco, P., Noël, Y., Causà, M., and Kirtman, B. (2014). “CRYSTAL14: a program for the ab initio investigation of crystalline solids,” Int. J. Quantum Chem. 114, 12871317.
Etter, M. C. (1990). “Encoding and decoding hydrogen-bond patterns of organic compounds,” Acc. Chem. Res. 23(4), 120126.
Favre-Nicolin, V. and Černý, R. (2002). FOX, “Free Objects for crystallography: a modular approach to ab initio structure determination from powder diffraction,” J. Appl. Crystallogr. 35, 734743.
Fawcett, T. G., Kabekkodu, S. N., Blanton, J. R., and Blanton, T. N. (2017). “Chemical analysis by diffraction: the Powder Diffraction File™,” Powder Diffr. 32(2), 6371.
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.
Groom, C. R., Bruno, I. J., Lightfoot, M. P., and Ward, S. C. (2016). “The Cambridge Structural Database,” Acta Crystallogr. Sect. B Struct. Sci. Cryst. Eng. Mater. 72, 171179.
Hirshfeld, F. L. (1977). “Bonded-atom fragments for describing molecular charge densities,” Theor. Chem. Acta 44, 129138.
ICDD (2017). PDF-4 + 2018 (Database), edited by Kabekkodu, S. (International Centre for Diffraction Data, Newtown Square, PA, USA).
Kaduk, J. A. (2002). “Use of the Inorganic Crystal Structure Database as a problem solving tool,” Acta Crystallogr. Sect. B Struct. Sci. 58, 370379.
Kaduk, J. A., Crowder, C. E., Zhong, K., Fawcett, T. G., and Suchomel, M. R. (2014). “Crystal structure of atomoxetine hydrochloride (Strattera), C17H22NOCl,” Powder Diffr. 29(3), 269273.
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. Synch. 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 60, 627668.
Meyer, G. A. and Bauer, J. F. (1994). “Terazosin polymorph and pharmaceutical composition,” US Patent 5,294,615.
O'Boyle, N., Banck, M., James, C. A., Morley, C., Vandermeersch, T., and Hutchison, G. R. (2011). “Open Babel: an open chemical toolbox,” J. Chem. Inform. 3, 33
Peintinger, M. F., Vilela Oliveira, D., and Bredow, T. (2013). “Consistent Gaussian basis sets of triple-zeta valence with polarization quality for solid-state calculations,” J. Comput. Chem. 34, 451459.
Rammohan, A. and Kaduk, J. A. (2018). “Crystal structures of alkali metal (Group 1) citrate salts,” Acta Crystallogr. B Struct. Sci. Cryst. Eng. Mat., 74, 239252.
Roteman, R. (1979). “1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-(2-tetrahydrofuroyl) piperazine hydrochloride dihydrate,” US Patent 4,251,532.
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. Cryst. Eng. Mater. 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. Inst. 79, 085105.
Wavefunction, Inc. (2017). Spartan ‘16 Version 2.0.1, Wavefunction Inc., 18401 Von Karman Ave., Suite 370, Irvine CA 92612.
Wheatley, A. M. and Kaduk, J. A. (2018). “Crystal structures of ammonium citrates,” manuscript in preparation.
Wolff, S. K., Grimwood, D. J., McKinnon, M. J., Turner, M. J., Jayatilaka, D., and Spackman, M. A. (2012). Crystal Explorer Version 3.1 (University of Western Australia).

Keywords

Type Description Title
UNKNOWN
Supplementary materials

Wheatley et al. supplementary material
Wheatley et al. supplementary material 1

 Unknown (2.7 MB)
2.7 MB
UNKNOWN
Supplementary materials

Wheatley et al. supplementary material
Wheatley et al. supplementary material 1

 Unknown (4 KB)
4 KB

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