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

Gutierrez, M.; Vallejos, G.; Fernández, C.; Cárdenas, A.; Brito, I.

doi:10.1107/S1600536810052463

Volume 67
Part 1
Pages o175-o176
January 2011

Received 6 December 2010
Accepted 14 December 2010
Online 18 December 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R = 0.098
wR = 0.240
Data-to-parameter ratio = 16.8
Details

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

Margarita Gutierrez,^a Gabriel Vallejos,^b Carlos Fernández,^a Alejandro Cárdenas ^c and Iván Brito ^d ^*

^aInstituto de Química de Recursos Naturales, Universidad de Talca, Casilla 747, Talca, Chile,^bInstituto de Química, Universidad Austral de Chile, Valdivia, Chile,^cDepartamento de Física, Facultad de Ciencias Básicas, Universidad de Antofagasta, Casilla 170, Antofagasta, Chile, and ^dDepartamento de Química, Facultad de Ciencias Básicas, Universidad de Antofagasta, Casilla 170, Antofagasta, Chile
Correspondence e-mail: ivanbritob@yahoo.com

The title compound, C₂₈H₂₄N₄O₄·H₂O, crystallizes with two organic molecules and two solvent water molecules in the asymmetric unit. The most obvious difference between the molecules is the torsion 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]. Another important difference is observed in the rotation of the nitro group with respect to the phenyl groups [3.5 (6) and 31.1 (6)°]. The pyrrolidinone fragment is cis oriented with respect to the 4-nitrophenyl fragment. In the crystal, molecules are linked into centrosymmetric R₄²(8) and R₄⁴(20) motifs by O-HO and N-HO interactions.

Related literature

For pharmacological activity of quinoline, see: Shi et al. (2008); Lunniss et al. (2009); He et al. (2005); Eswaran et al. (2010). For the synthesis and medicinal uses of quinolines, see: Kalita et al. (2006); Kouznetsov et al. (2005); Sankaran et al. (2010). For reactions of isoxazoles see: Taldone et al. (2008); Narlawar et al. (2008); Velaparthi et al. (2008); Rizzi et al. (2008); Lautens & Roy (2000); Broggini et al. (2005); Kotera et al. (1970). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₂₈H₂₄N₄O₄·H₂O
M_r = 498.53
Triclinic, $[P \overline 1]$
a = 13.516 (8) Å
b = 14.193 (6) Å
c = 14.987 (11) Å
= 70.151 (10)°
= 79.62 (2)°
= 69.700 (9)°
V = 2530 (3) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 293 K
0.39 × 0.17 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer
21159 measured reflections
11596 independent reflections
7891 reflections with I > 2(I)
R_int = 0.090

Refinement

R[F² > 2(F²)] = 0.098
wR(F²) = 0.240
S = 1.16
11596 reflections
691 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.34 e Å^-3
_min = -0.33 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1W-H1WAO4ⁱ	0.83 (7)	2.07 (7)	2.904 (5)	173 (6)
O1W-H1WBO4ⁱⁱ	1.03 (8)	1.87 (8)	2.877 (5)	167 (6)
O2W-H2WBO7	0.97 (8)	1.80 (9)	2.754 (5)	165 (8)
N6-H6NO2Wⁱⁱⁱ	0.83 (4)	2.13 (4)	2.958 (5)	179 (5)
O2W-H2WAO1W	0.80 (6)	2.09 (6)	2.883 (6)	175 (6)
Symmetry codes: (i) x-1, y, z+1; (ii) -x+1, -y, -z+1; (iii) -x, -y+1, -z+1.

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: OM2389 ).

Acknowledgements

LAS thanks FONDECYT (project No. 1100481) and PBCT ADI-38. We 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.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Broggini, G., Chiesa, K., De Marchi, I., Martinelli, M., Pilati, T. & Zecchi, G. (2005). Tetrahedron, 61, 3525-3531.
Eswaran, S., Adhikari, V. A., Pal, K. N. & Chowdhury, H. I. (2010). Bioorg. Med. Chem. 20, 1040-1044.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
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.
Kalita, P., Baruah, B. & Bhuyan, P. (2006). Tetrahedron Lett. 47, 7779-7782.
Kotera, K., Takano, Y., Matsuura, A. & Kitahonoki, K. (1970). Tetrahedron, 26, 539-556.
Kouznetsov, V. V., Vargas, L. Y. & Melendez, C. C. (2005). Curr. Org. Chem. 9, 141-161.
Lautens, M. & Roy, A. (2000). Org. Lett. 2, 555-557.
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.
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.
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.
Sankaran, M., Kumarasamy, C., Chokkalingam, U. & Mohan, P. S. (2010). Bioorg. Med. Chem. Lett. 20, 7147-7151.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
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.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Taldone, T., Gozman, A., Maharaj, R. & Chiosis, G. (2008). Curr. Opin. Pharmacol. 8, 370-374.
Velaparthi, S., Brunsteiner, M., Uddin, R., Wan, B., Franzblau, S. G. & Petukhov, P. A. (2008). J. Med. Chem. 51, 1999-2002.

organic compounds