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X-ray diffraction data of 4-phenyl-6-(trifluoromethyl)-3,4-dihydroquinolin-2(1H)-one and its synthetic precursor N-[4-(trifluoromethyl)phenyl]cinnamamide

Published online by Cambridge University Press:  10 June 2016

Jose H. Quintana Mendoza ,
J. A. Henao ,
Carlos E. Rondón Flórez ,
Carlos E. Puerto Galvis  and
Vladimir V. Kouznetsov
Jose H. Quintana Mendoza
Affiliation:
Grupo de Investigación en Química Estructural (GIQUE), Escuela de Química, Facultad de Ciencias, Universidad Industrial de Santander, A.A. 678, Carrera 27, Calle 9 Ciudadela Universitaria, Bucaramanga, Colombia
J. A. Henao*
Affiliation:
Grupo de Investigación en Química Estructural (GIQUE), Escuela de Química, Facultad de Ciencias, Universidad Industrial de Santander, A.A. 678, Carrera 27, Calle 9 Ciudadela Universitaria, Bucaramanga, Colombia
Carlos E. Rondón Flórez
Affiliation:
Laboratorio de Química Orgánica y Biomolecular (LQOBio), Universidad Industrial de Santander, Parque Tecnológico Guatiguará, Km 2 vía refugio, Piedecuesta, A.A. 678, Bucaramanga, Colombia
Carlos E. Puerto Galvis
Affiliation:
Laboratorio de Química Orgánica y Biomolecular (LQOBio), Universidad Industrial de Santander, Parque Tecnológico Guatiguará, Km 2 vía refugio, Piedecuesta, A.A. 678, Bucaramanga, Colombia
Vladimir V. Kouznetsov
Affiliation:
Laboratorio de Química Orgánica y Biomolecular (LQOBio), Universidad Industrial de Santander, Parque Tecnológico Guatiguará, Km 2 vía refugio, Piedecuesta, A.A. 678, Bucaramanga, Colombia
*
a)Author to whom correspondence should be addressed. Electronic mail: jahenao@uis.edu.co
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Abstract

The title compound, the 4-phenyl-6-(trifluoromethyl)-3,4-dihydroquinolin-2(1H)-one (4) with chemical formula: (C16H12F3NO), was synthesized from N-[4-(trifluoromethyl)phenyl]cinnamamide (3), chemical formula: (C16H12F3NO), through an intramolecular cyclization mediated by triflic acid. Preliminary molecular characterization of both compounds was performed by Fourier transform infrared spectroscopy, gas chromatography mass spectrometry, and nuclear magnetic resonance spectroscopy (1H, 13C); crystallographic characterization was completed by X-ray diffraction of polycrystalline samples. The title compound 4 crystallized in a monoclinic system and unit-cell parameters are reported [a = 16.002 (3), b = 5.170 (1), c = 17.733 (3) Å, β = 111.11 (2)°, unit-cell volume V = 1368.5 (3) Å3, Z = 4] P21/c (No. 14) space group; the title compound 3 crystallized in a monoclinic system and unit-cell parameters are reported [a = 12.902 (2), b = 5.144 (1), c = 20.513 (5) Å, β = 91.67 (2)°, unit-cell volume V = 1360.7 (4) Å3, Z = 4] P21/c (No. 14) space group.

Keywords

cinnamamides2-quinolinonesintramolecular cyclizationX-ray powder diffraction data
Type
New Diffraction Data
Information
Powder Diffraction , Volume 31 , Issue 3 , September 2016 , pp. 233 - 239
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Copyright
Copyright © International Centre for Diffraction Data 2016 

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References

Boultif, A. and Loüer, D. (2004). “Powder pattern indexing with the dichotomy method”, J. Appl. Crystallogr. 37, 724–731.CrossRefGoogle Scholar
de Wolff, P. M. (1968). “A simplified criterion for the reliability of a powder pattern indexing”, J. Appl. Crystallogr. 1, 108–113.CrossRefGoogle Scholar
Dong, C. (1999). “PowderX: windows-95-based program for powder X-ray diffraction data processing”, J. Appl. Crystallogr. 32, 838.CrossRefGoogle Scholar
Joseph, B., Darro, F., Behard, A., Lesur, B., Collignon, F., Decaestecker, C., Frydman, A., Guillaumet, G. and Kiss, R. (2002). “3-Aryl-2-quinolone derivatives: synthesis and characterization of in vitro and in vivo antitumor effects with emphasis on a new therapeutical target connected with cell migration”, J. Med. Chem. 45, 2543–2555.CrossRefGoogle ScholarPubMed
Kadnikov, D. V. and Larock, R. C. (2004). “Synthesis of 2-quinolones via palladium-catalyzed carbonylative annulation of internal alkynes by N-substituted o-iodoanilines”, J. Org. Chem. 69, 6772–6780.CrossRefGoogle ScholarPubMed
Lanigan, R. M., Starkov, P. and Sheppard, T. D. (2013). “Direct synthesis of amides from carboxylic acids and amines using B(OCH2CF3)3 ”, J. Org. Chem. 78, 4512–4523.CrossRefGoogle ScholarPubMed
Laugier, J. and Bochu, B. (2002). CHEKCELL. “LMGP-Suite Suite of Programs for the interpretation of X-ray. Experiments,” ENSP/Laboratoire des Matériaux et du Génie Physique, BP 46. 38042 Saint Martin d'Hères, France. http://www.inpg.fr/LMGP and http://www.ccp14.ac.uk/tutorial/lmgp/.Google Scholar
Lee-Manion, A. M., Price, R. K., Strain, J. J., Dimberg, L. H., Sunnerheim, K. and Welch, R. W. (2009). “ In vitro antioxidant activity and antigenotoxic effects of avenanthramides and related Compounds”, J. Agric. Food Chem. 57, 10619–10624.CrossRefGoogle ScholarPubMed
Mighell, A. D., Hubbard, C. R. and Stalick, J. K. (1981). “NBS* AIDS80: A FORTRAN program for crystallographic data evaluation”, National Bureau of Standards (USA), Technical Note 1141.CrossRefGoogle Scholar
Rachinger, W. A. (1948). “A correction for the α 1 α 2 doublet in the measurement of widths of X-ray diffraction lines”, J. Sci. Instrum. 25, 254.CrossRefGoogle Scholar
Roughley, S. D. and Jordan, A. M. (2011). “The medicinal chemist's toolbox: an analysis of reactions used in the pursuit of drug candidates”, J. Med. Chem. 54, 3451–3479.CrossRefGoogle ScholarPubMed
Savitzky, A. and Golay, M. J. (1964). “Smoothing and differentiation of data by simplified least squares procedures”, Anal. Chem. 36, 1627–1639.CrossRefGoogle Scholar
Smith, G. S. and Snyder, R. L. (1979). “ F N : A criterion for rating powder diffraction patterns and evaluating the reliability of powder-pattern indexing”, J. Appl. Crystallogr. 12, 60–65.CrossRefGoogle Scholar
Sonneveld, E. J. and Visser, J. W. (1975). “Automatic collection of powder data from photographs”, J. Appl. Crystallogr. 8, 1–7.CrossRefGoogle Scholar
Wang, W., Peng, X., Qin, X., Zhao, X., Ma, C., Tung, C-H. and Xu, Z. (2015). “Synthesis of quinolinones with palladium-catalyzed oxidative annulation between acrylamides and arynes”, J. Org. Chem. 80, 2835–2841.CrossRefGoogle ScholarPubMed
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