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Crystal structure of alfuzosin hydrochloride, C19H28N5O4Cl

Published online by Cambridge University Press:  31 August 2022

James A. Kaduk Open the ORCID record for James A. Kaduk [Opens in a new window]
James A. Kaduk*
Affiliation:
Illinois Institute of Technology, 3101 S. Dearborn St., Chicago, IL 60616, USA North Central College, 131 S. Loomis St., Naperville, IL 60540, USA
*
a)Author to whom correspondence should be addressed. Electronic mail: [email protected]
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Abstract

The crystal structure of anhydrous alfuzosin hydrochloride has been solved and refined using laboratory X-ray powder diffraction data and optimized using density functional theory techniques. Anhydrous alfuzosin hydrochloride crystallizes in space group P-1 with a = 9.3214(16), b = 9.3997(29), c = 12.6172(64) Å, α = 107.993(11), β = 100.386(9), γ = 90.229(6)°, V = 1032.1(10) Å3, and Z = 2 at ambient conditions. Thermal expansion is anisotropic, being 8× larger in the c-direction than in the other two. The crystal structure is characterized by a stack of planar fused rings along the b-axis, and layers of the more-corrugated portion of the molecule parallel to the ab-plane. There are two strong N–H⋯Cl hydrogen bonds, as well as seven C-H⋯Cl hydrogen bonds. The powder patterns have been submitted to ICDD for inclusion in the Powder Diffraction File™ (PDF®).

Keywords

alfuzosin hydrochlorideuroxatral®Rietveld refinementdensity functional theory
Type
New Diffraction Data
Information
Powder Diffraction , Volume 37 , Issue 3 , September 2022 , pp. 171 - 182
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Copyright
Copyright © The Author(s), 2022. Published by Cambridge University Press on behalf of International Centre for Diffraction Data

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References

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, 1231–1235.CrossRefGoogle Scholar
Anumula, R. R., Alla, S., Madivada, L. R., and Gilla, G. (2007). “Alfuzosin hydrochloride polymorphs,” US patent application US 2007/0049756 A1.Google Scholar
Ashour, S., Chehna, M. F., and Bayram, R. (2006). “Spectrophotometric determination of alfuzosin HCl in pharmaceutical formulations with some sulphonephthalein dyes,” Int. J. Biomed. Sci.: IJBS 2, 273–278.Google ScholarPubMed
Barr, G., Dong, W., and Gilmore, C. J. (2004). “High-throughput powder diffraction. IV. Cluster validation using silhouettes and fuzzy clustering,” J. Appl. Cryst. 37, 874–882.CrossRefGoogle Scholar
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), 1555–1573.CrossRefGoogle Scholar
Borrega, R. and Kitamura, S. (1996). “Alfuzosin hydrochloride dihydrate,” U.S. patent 5,545,738.Google Scholar
Bravais, A. (1866). Etudes Cristallographiques (Gauthier Villars, Paris).Google Scholar
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, 2133–2144.CrossRefGoogle ScholarPubMed
Crystal Impact – Dr. H. Putz & Dr. K. Brandenburg. (2022). Diamond – crystal and molecular structure visualization. Kreuzherrenstr. 102, 53227 Bonn, Germany. Available at: https://www.crystalimpact.de/diamond.Google Scholar
Dassault Systèmes (2021). Materials Studio 2021 (BIOVIA, San Diego, CA).Google Scholar
Donnay, J. D. H., and Harker, D. (1937). “A new law of crystal morphology extending the law of Bravais,” Am. Mineral. 22, 446–447.Google Scholar
Dovesi, R., Erba, A., Orlando, R., Zicovich-Wilson, C. M., Civalleri, B., Maschio, L., Rerat, M., Casassa, S., Baima, J., Salustro, S., and Kirtman, B. (2018). “WIREs comput,” Mol. Sci. 8, e1360.Google Scholar
Etter, M. C. (1990). “Encoding and decoding hydrogen-bond patterns of organic compounds,” Acc. Chem. Res. 23(4), 120–126.CrossRefGoogle Scholar
Friedel, G. (1907). “Etudes sur la loi de Bravais,” Bull. Soc. Fr. Mineral 30, 326–455.Google Scholar
Gates-Rector, S. and Blanton, T. (2019). “The powder diffraction file: a quality materials characterization database,” Powd. Diffr. 39(4), 352–360.CrossRefGoogle Scholar
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, 10686–10696.CrossRefGoogle Scholar
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, 171–179.CrossRefGoogle ScholarPubMed
Hirshfeld, F. L. (1977). “Bonded-atom fragments for describing molecular charge densities,” Theor. Chem. Acta 44, 129–138.CrossRefGoogle Scholar
Joshi, N. S., Ramam, B. P., and Rao, K. E. (2006). “Process for the preparation of alfuzosin and salts thereof and novel crystalline forms of alfuzosin,” International patent application WO 2006/090268 A2.Google Scholar
Kim, S., Chen, J., Cheng, T., Gindulyte, A., He, J., He, S., Li, Q., Shoemaker, B. A., Thiessen, P. A., Yu, B., Zaslavsky, L., Zhang, J., and Bolton, E. E. (2019). “Pubchem 2019 update: improved access to chemical data,” Nucleic Acids Res. 47(D1), D1102–D1109. doi:10.1093/nar/gky1033.CrossRefGoogle ScholarPubMed
Kresse, G. and Furthmüller, J. (1996). “Efficiency of Ab-initio total energy calculations for metals and semiconductors using a plane-wave basis set,” Comput. Mater. Sci. 6, 15–50.CrossRefGoogle Scholar
Macrae, C. F., Sovago, I., Cottrell, S. J., Galek, P. T. A., McCabe, P., Pidcock, E., Platings, M., Shields, G. P., Stevens, J. S., Towler, M., and Wood, P. A. (2020). “Mercury 4.0: from visualization to design and prediction,” J. Appl. Crystallogr. 53, 226–235.CrossRefGoogle ScholarPubMed
Materials Design (2016). MedeA 2.20.4 (Materials Design Inc., Angel Fire, NM).Google Scholar
MDI (2021). JADE Pro Version 8.1 (Computer Software) (Materials Data, Livermore, CA, USA).Google Scholar
O'Boyle, N., Banck, M., James, C. A., Morley, C., Vandermeersch, , and Hutchison, G. R. (2011). “Open babel: an open chemical toolbox,” J. Chem. Informatics 3, 33. doi:10.1186/1758-2946-3-33.Google ScholarPubMed
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, 451–459.CrossRefGoogle ScholarPubMed
Satyanarayana Reddy, M., Kishore Kumar, M., Kondal Reddy, B., and Venkatesh, M. (2007). “An improved and industrial process for the preparation of alfuzosin hydrochloride and its novel properties,” International patent application WO 2007/063556 A2.CrossRefGoogle Scholar
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 Cryst. Sec. B: struct. Sci. 56(3), 455–465.CrossRefGoogle ScholarPubMed
Silk Scientific (2013). UN-SCAN-IT 7.0 (Silk Scientific Corporation, Orem, UT).Google Scholar
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, 882–886.CrossRefGoogle Scholar
Toby, B. H. and Von Dreele, R. B. (2013). “GSAS II: the genesis of a modern open source all purpose crystallography software package,” J. Appl. Crystallogr. 46, 544–549.CrossRefGoogle Scholar
Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Spackman, P. R., Jayatilaka, D., and Spackman, M. A. (2017). CrystalExplorer17 (University of Western Australia). Available at: http://hirshfeldsurface.net.Google Scholar
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 Cryst. Sect. B: Struct. Sci., Cryst. Eng. Mater. 70(6), 1020–1032.CrossRefGoogle Scholar
Vickers, M. (2009). ICDD private communication; PDF entry 00-060-1193.Google Scholar
Wavefunction, Inc. (2020). Spartan ‘18 Version 1.4.5, Wavefunction Inc., 18401 Von Karman Ave., Suite 370, Irvine CA 92612.Google Scholar