4-Hydr­oxy-3-(1′-methyl-2-oxo-4′-phenyl­spiro­[indoline-3,2′-pyrrolidine]-3′-yl­carbon­yl)quinolin-2(1H)-one

Revathi, K.; Sankaran, M.; Ramesh, P.; Mohan, P.S.; Ponnuswamy, M.N.

doi:10.1107/S1600536810010500

Volume 66
Part 4
Page o952
April 2010

Received 15 March 2010
Accepted 20 March 2010
Online 27 March 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R = 0.040
wR = 0.119
Data-to-parameter ratio = 17.6
Details

4-Hydroxy-3-(1'-methyl-2-oxo-4'-phenylspiro[indoline-3,2'-pyrrolidine]-3'-ylcarbonyl)quinolin-2(1H)-one

K. Revathi,^a ⁺ M. Sankaran,^b P. Ramesh,^a P. S. Mohan ^b and M. N. Ponnuswamy ^a ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and ^bDepartment of Chemistry, School of Chemical Sciences, Bharathiar University, Coimbatore 641 046, India
Correspondence e-mail: mnpsy2004@yahoo.com

In the title compound, C₂₈H₂₃N₃O₄, the dihedral angle between the quinoline and indole ring systems is 29.30 (5)°. The pyrrolidine ring adopts a twist conformation. An intramolecular O-HO hydrogen bond generates an S(6) ring motif. A weak intramolecular C3-H3O3 interaction is also observed. In the crystal, molecules are linked by two sets of N-HO hydrogen bonds, forming centrosymmetric dimers containing two R₂²(8) ring motifs. The dimers are linked via C-H [pi] interactions.

Related literature

For general background to indole, quinoline and pyrrolidine derivatives, see: Amalraj et al. (2003); Cordell (1981); Suzuki et al. (1994). For puckering parameters, see: Cremer & Pople (1975). For asymmetry parameters, see: Nardelli (1983). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₂₈H₂₃N₃O₄
M_r = 465.49
Triclinic, $[P \overline 1]$
a = 9.6918 (3) Å
b = 11.0258 (3) Å
c = 12.9663 (4) Å
= 69.111 (1)°
= 72.044 (2)°
= 66.410 (1)°
V = 1163.93 (6) Å³
Z = 2
Mo K radiation
= 0.09 mm^-1
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) T_min = 0.982, T_max = 0.982
21655 measured reflections
5795 independent reflections
4635 reflections with I > 2(I)
R_int = 0.023

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.119
S = 1.03
5795 reflections
329 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.22 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg6 is the centroid of the C26-C31 ring.

D-HA	D-H	HA	DA	D-HA
O4-H4AO2	0.99 (2)	1.56 (2)	2.4840 (14)	155 (2)
N8-H8O3ⁱ	0.89 (2)	1.92 (2)	2.7837 (13)	165 (2)
N18-H18O1ⁱ	0.90 (2)	1.95 (2)	2.8497 (14)	177 (2)
C3-H3O3	0.98	2.21	2.7944 (13)	117
C21-H21Cg6ⁱⁱ	0.93	2.72	3.5360 (18)	147
Symmetry codes: (i) -x, -y+2, -z; (ii) -x+1, -y+2, -z.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI5061 ).

References

Amalraj, A., Raghunathan, R., Sridevi Kumari, M. R. & Raman, N. (2003). Bioorg. Med. Chem. 11, 407-419.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cordell, G. (1981). Introduction to Alkaloids: A Biogenic Approach. New York: Wiley International.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Suzuki, H., Aoyagi, S. & Kibayashi, C. (1994). Tetrahedron Lett. 35, 6119-6122.

organic compounds