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Crystal structure of nilotinib, C28H22F3N7O

Published online by Cambridge University Press:  14 August 2015

James A. Kaduk ,
Kai Zhong ,
Amy M. Gindhart  and
Thomas N. Blanton
James A. Kaduk*
Affiliation:
Illinois Institute of Technology, 3101 S. Dearborn St., Chicago, Illinois 60616
Kai Zhong
Affiliation:
ICDD, 12 Campus Blvd., Newtown Square, Pennsylvania 19073-3273
Amy M. Gindhart
Affiliation:
ICDD, 12 Campus Blvd., Newtown Square, Pennsylvania 19073-3273
Thomas N. Blanton
Affiliation:
ICDD, 12 Campus Blvd., Newtown Square, Pennsylvania 19073-3273
*
a)Author to whom correspondence should be addressed. Electronic mail: [email protected]
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Abstract

The crystal structure of nilotinib has been solved and refined using synchrotron X-ray powder diffraction data, and optimized using density functional techniques. Nilotinib crystallizes in space group P1 (#1) with a = 4.518 14(3), b = 10.638 01(5), c = 13.703 77(8) Å, α = 68.8607(4), β = 82.1486(5), γ = 84.1978(5)°, V = 607.62(1) Å3, and Z = 1. The most prominent feature of the structure is two strong hydrogen bonds. These form chains with a graph set C1,1(13); the chains run along [111]. Several weak C–H···O hydrogen bonds also contribute to the packing. The powder pattern has been submitted to ICDD for inclusion in future releases of the Powder Diffraction File™.

Keywords

nilotinibTasigna®powder diffractionRietveld refinementdensity functional theory
Type
Technical Articles
Information
Powder Diffraction , Volume 30 , Issue 3 , September 2015 , pp. 270 - 277
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Copyright
Copyright © International Centre for Diffraction Data 2015 

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References

Accelrys (2013). Materials Studio 7.0 (Accelrys Software Inc., San Diego, California).Google Scholar
Allen, F. H. (2002). “The Cambridge Structural Database: a quarter of a million crystal structures and rising,” Acta Crystallogr. B, Struct. Sci. 58, 380–388.Google Scholar
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
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.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.Google Scholar
Deremer, D. L., Ustun, C., and Natarajan, K. (2008). “Nilotinib: a second-generation tyrosine kinase inhibitor for the treatment of chronic myelogenous leukemia,” Clin. Ther. 30(11), 1956–1975.Google Scholar
Donnay, J. D. H. and Harker, D. (1937). “A new law of crystal morphology extending the law of Bravais,” Am. Mineral. 22, 446–467.Google Scholar
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, 571–573.Google Scholar
Etter, M. C. (1990). “Encoding and decoding hydrogen-bond patterns of organic compounds,” Acc. Chem. Res. 23(4), 120–126.CrossRefGoogle Scholar
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, 734–743.Google Scholar
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), 892–900.Google Scholar
Friedel, G. (1907). “Etudes sur la loi de Bravais,” Bull. Soc. Fr. Mineral. 30, 326–455.Google 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.Google Scholar
Hirshfeld, F. L. (1977). “Bonded-atom fragments for describing molecular charge densities,” Theor. Chem. Acta 44, 129–138.Google Scholar
ICDD (2014). PDF-4 + 2014 (Database), edited by Kabekkodu, S. (International Centre for Diffraction Data, Newtown Square, PA).Google Scholar
Larson, A. C. and Von Dreele, R. B. (2004). General Structure Analysis System (GSAS), (Report LAUR 86-784). Los Alamos, New Mexico: Los Alamos National Laboratory.Google Scholar
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. Synchrotron Radiat. 15(5), 427–432.Google Scholar
Louër, D. and Boultif, A. (2007). “Powder pattern indexing and the dichotomy algorithm,” Z. Kristallogr. Suppl. 2007, 191–196.CrossRefGoogle Scholar
McKinnon, J. J., Spackman, M. A., and Mitchell, A. S. (2004). “Novel tools for visualizing and exploring intermolecular interactions in molecular crystals,” Acta Crystallogr. B 60, 627–668.Google Scholar
Nada, R., Catlow, C. R. A., Pisani, and Orlando, R. (1993). “Ab initio Hartree-Fock perturbed-cluster study of neutral defects in LiF,” Model. Simul. Mater. Sci. Eng. 1, 165–187.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. Inf. 3, 33.Google 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 Crystallogr. B, Struct. Sci. 56(3), 455–465.CrossRefGoogle ScholarPubMed
Spackman, M. A. and Jayatilaka, D. (2009). “Hirshfeld surface analysis,” CrystEngComm. 11, 19–32.CrossRefGoogle Scholar
Stephens, P. W. (1999). “Phenomenological model of anisotropic peak broadening in powder diffraction,” J. Appl. Crystallogr. 32, 281–289.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.Google Scholar
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), 79–83.CrossRefGoogle 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 Crystallogr. B, Struct. Sci., Cryst. Eng. Mater. 70(6), 1020–1032.CrossRefGoogle ScholarPubMed
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.Google Scholar
Wavefunction, Inc. (2013). Spartan'14 Version 1.1.0 (Wavefunction Inc., Irvine, California).Google Scholar
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, Perth, Australia).Google Scholar
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