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Volume 67 
Part 2 
Pages o308-o309  
February 2011  

Received 20 December 2010
Accepted 24 December 2010
Online 8 January 2011

[sj5084sup1]
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Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.007 Å
R = 0.075
wR = 0.162
Data-to-parameter ratio = 9.6
Details
Open access

1-[2-(4-Nitrophenyl)-5-(5-phenyl-1,2-oxazol-3-yl)-1,2,3,4-tetrahydroquinolin-4-yl]pyrrolidin-2-one

Margarita Gutierrez,a Luis Astudillo,a Luisa Quesada,a Iván Britob* and Matías López-Rodríguezc

aInstituto de Quimica de Recursos Naturales, Universidad de Talca, Casilla 747, Talca, Chile,bDepartamento de Química, Facultad de Ciencias Básicas, Universidad de Antofagasta, Casilla 170, Antofagasta - Chile, and cInstituto de Bio-Orgánica 'Antonio González', Universidad de La Laguna, Astrofísico Francisco Sánchez N°2, La Laguna, Tenerife, Spain.
Correspondence e-mail: ivanbritob@yahoo.com

The title compound, (I) C28H24N4O4, is the trans diastereoisomer of the compound 1-[2-(4-nitrophenyl)-6-(5-phenyl-3-isoxazolyl)-1,2,3,4-tetrahydro-4-quinolinyl]-2-pyrrolidinone monohydrate, (II) [Gutierrez et al. (2011[Gutierrez, M., Vallejos, G., Fernández, C., Cárdenas, A. & Brito, I. (2011). Acta Cryst. E67, o175-o176.]). Acta Cryst. E67, o175-o176]. The most obvious differences between the diastereoisomers are the dihedral angles between the isoxazole ring and the benzene and phenyl rings [47.0 (2); 56.4 (2) and 33.3 (2); 11.0 (2)°, respectively, for (II) 75.4 (2) and 5.8 (3), respectively, for (I)]. In the crystal of (I), the molecules are linked by N-H...O interactions into a chain along [001] with graph-set notation C(8).

Related literature

For details of nitrogen-containing heterocyclic compounds, see: Sankaran et al. (2010[Sankaran, M., Kumarasamy, C., Chokkalingam, U. & Mohan, P. S. (2010). Bioorg. Med. Chem. Lett. 20, 7147-7151.]) and for their pharmacological activity, see: Shi et al. (2008[Shi, A., Nguyen, T. A., Battina, K. S., Rana, S., Takemoto, J. D., Chiang, K. P. & Hua, D. (2008). Bioorg. Med. Chem. Lett. 18, 3364-3368.]); Lunniss et al. (2009[Lunniss, J. C., Cooper, W. J. A., Eldred, D. C., Kranz, M., Lindvall, M., Lucas, S. F., Neu, M., Preston, A., Ranshaw, E. L., Redgrave, J. A., Robinson, E. J., Shimpley, J. T., Solanke, E. Y., Somers, O. D. & Wiseman, O. J. (2009). Bioorg. Med. Chem. Lett. 19, 1380-1385.]); He et al. (2005[He, F.-J., Yun, L.-H., Yang, R.-F., Xiao, Z.-Y., Cheng, J.-P., Zhou, W.-X. & Zhang, Y.-X. (2005). Bioorg. Med. Chem. Lett. 15, 2980-2985.]); Eswaran et al. (2010[Eswaran, S., Adhikari, V. A., Pal, K. N. & Chowdhury, H. I. (2010). Bioorg. Med. Chem. 20, 1040-1044.]). For reactions of isoxazoles, see: Taldone et al. (2008[Taldone, T., Gozman, A., Maharaj, R. & Chiosis, G. (2008). Curr. Opin. Pharmacol. 8, 370-374.]); Narlawar et al. (2008[Narlawar, R., Pickhardt, M., Leuchtenberger, S., Baumann, K., Krause, S., Dyrks, T., Weggen, S., Mandelkow, E. & Schmidt, B. (2008). Chem. Med. Chem. 3, 165-172.]); Velaparthi et al. (2008[Velaparthi, S., Brunsteiner, M., Uddin, R., Wan, B., Franzblau, S. G. & Petukhov, P. A. (2008). J. Med. Chem. 51, 1999-2002.]); Rizzi et al. (2008[Rizzi, L., Dallanoce, C., Matera, C., Magrone, P., Pucci, L., Gotti, C., Clementi, F. & De Amici, M. (2008). Bioorg. Med. Chem. Lett. 18, 4651-4654.]); Lautens & Roy (2000[Lautens, M. & Roy, A. (2000). Org. Lett. 2, 555-557.]); Broggini et al. (2005[Broggini, G., Chiesa, K., De Marchi, I., Martinelli, M., Pilati, T. & Zecchi, G. (2005). Tetrahedron, 61, 3525-3531.]); Kotera et al. (1970[Kotera, K., Takano, Y., Matsuura, A. & Kitahonoki, K. (1970). Tetrahedron, 26, 539-556.]). For applications of compounds possessing the quinoline system as drugs and pharmaceuticals, see: Kalita et al. (2006[Kalita, P., Baruah, B. & Bhuyan, P. (2006). Tetrahedron Lett. 47, 7779-7782.]). For syntheses of quinolines, see: Kouznetsov et al. (2005[Kouznetsov, V. V., Vargas, L. Y. & Melendez, C. C. (2005). Curr. Org. Chem. 9, 141-161.]). For the trans diastereoisomer of the title compound, see: Gutierrez et al. (2011[Gutierrez, M., Vallejos, G., Fernández, C., Cárdenas, A. & Brito, I. (2011). Acta Cryst. E67, o175-o176.]). For graph-set motifs see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]) and for puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.])

[Scheme 1]

Experimental

Crystal data

  • C28H24N4O4

  • Mr = 480.51

  • Hexagonal, P 61

  • a = 20.753 (3) Å

  • c = 10.446 (2) Å

  • V = 3896.2 (11) Å3

  • Z = 6

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 293 K

  • 0.20 × 0.20 × 0.18 mm
Data collection

  • Nonius KappaCCD area-detector diffractometer

  • 5951 measured reflections

  • 3144 independent reflections

  • 2646 reflections with I > 2[sigma](I)

  • Rint = 0.026
Refinement

  • R[F2 > 2[sigma](F2)] = 0.075

  • wR(F2) = 0.162

  • S = 1.22

  • 3144 reflections

  • 329 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2N...O4i 0.87 (3) 1.99 (3) 2.859 (6) 180 (5)
Symmetry code: (i) [y, -x+y, z-{\script{1\over 6}}].

Data collection: COLLECT (Nonius, 2000[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York; Academic Press.]); data reduction: DENZO-SMN; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5084 ).

Acknowledgements

LAS thanks FONDECYT (project No. 1100481) and PBCT ADI-38. We also thank the Spanish Research Council (CSIC) for providing us with a free-of-charge licence for the CSD system.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [ISI] [CrossRef] [ChemPort] [details]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Broggini, G., Chiesa, K., De Marchi, I., Martinelli, M., Pilati, T. & Zecchi, G. (2005). Tetrahedron, 61, 3525-3531.  [CrossRef] [ChemPort]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Eswaran, S., Adhikari, V. A., Pal, K. N. & Chowdhury, H. I. (2010). Bioorg. Med. Chem. 20, 1040-1044.  [ChemPort]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Gutierrez, M., Vallejos, G., Fernández, C., Cárdenas, A. & Brito, I. (2011). Acta Cryst. E67, o175-o176.  [CrossRef] [details]
He, F.-J., Yun, L.-H., Yang, R.-F., Xiao, Z.-Y., Cheng, J.-P., Zhou, W.-X. & Zhang, Y.-X. (2005). Bioorg. Med. Chem. Lett. 15, 2980-2985.  [CrossRef] [PubMed] [ChemPort]
Kalita, P., Baruah, B. & Bhuyan, P. (2006). Tetrahedron Lett. 47, 7779-7782.  [CrossRef] [ChemPort]
Kotera, K., Takano, Y., Matsuura, A. & Kitahonoki, K. (1970). Tetrahedron, 26, 539-556.  [CrossRef] [ChemPort]
Kouznetsov, V. V., Vargas, L. Y. & Melendez, C. C. (2005). Curr. Org. Chem. 9, 141-161.  [CrossRef] [ChemPort]
Lautens, M. & Roy, A. (2000). Org. Lett. 2, 555-557.  [CrossRef] [PubMed] [ChemPort]
Lunniss, J. C., Cooper, W. J. A., Eldred, D. C., Kranz, M., Lindvall, M., Lucas, S. F., Neu, M., Preston, A., Ranshaw, E. L., Redgrave, J. A., Robinson, E. J., Shimpley, J. T., Solanke, E. Y., Somers, O. D. & Wiseman, O. J. (2009). Bioorg. Med. Chem. Lett. 19, 1380-1385.  [CrossRef] [PubMed] [ChemPort]
Narlawar, R., Pickhardt, M., Leuchtenberger, S., Baumann, K., Krause, S., Dyrks, T., Weggen, S., Mandelkow, E. & Schmidt, B. (2008). Chem. Med. Chem. 3, 165-172.  [PubMed] [ChemPort]
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York; Academic Press.
Rizzi, L., Dallanoce, C., Matera, C., Magrone, P., Pucci, L., Gotti, C., Clementi, F. & De Amici, M. (2008). Bioorg. Med. Chem. Lett. 18, 4651-4654.  [CrossRef] [PubMed] [ChemPort]
Sankaran, M., Kumarasamy, C., Chokkalingam, U. & Mohan, P. S. (2010). Bioorg. Med. Chem. Lett. 20, 7147-7151.  [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shi, A., Nguyen, T. A., Battina, K. S., Rana, S., Takemoto, J. D., Chiang, K. P. & Hua, D. (2008). Bioorg. Med. Chem. Lett. 18, 3364-3368.  [CrossRef] [PubMed] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Taldone, T., Gozman, A., Maharaj, R. & Chiosis, G. (2008). Curr. Opin. Pharmacol. 8, 370-374.  [ISI] [CrossRef] [PubMed] [ChemPort]
Velaparthi, S., Brunsteiner, M., Uddin, R., Wan, B., Franzblau, S. G. & Petukhov, P. A. (2008). J. Med. Chem. 51, 1999-2002.  [ISI] [CrossRef] [PubMed] [ChemPort]

Acta Cryst (2011). E67, o308-o309   [ doi:10.1107/S1600536810054048 ]

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