Methyl 4′-(4-fluoro­phen­yl)-1′-methyl-3′-nitro­methyl-2-oxospiro­[indoline-3,2′-pyrrolidine]-3′-carboxyl­ate

Revathi, B.K.; Sathya, S.; Usha, G.; Murugan, G.; Bakthadoss, M.

doi:10.1107/S1600536813001578

Volume 69
Part 2
Page o278
February 2013

Received 2 January 2013
Accepted 16 January 2013
Online 23 January 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.047
wR = 0.132
Data-to-parameter ratio = 9.4
Details

Methyl 4'-(4-fluorophenyl)-1'-methyl-3'-nitromethyl-2-oxospiro[indoline-3,2'-pyrrolidine]-3'-carboxylate

B. K. Revathi,^a S. Sathya,^a G. Usha,^a ^* G. Murugan ^b and M. Bakthadoss ^b

^aPost Graduate and Research Department of Physics, Queen Mary's College, Chennai-4, Tamilnadu, India, and ^bDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai-25, Tamilnadu, India
Correspondence e-mail: guqmc@yahoo.com

In the title compound, C₂₁H₂₀FN₃O₅, the the pyrrolidine ring makes dihedral angles of 84.91 (6) and 62.38 (7)° with the oxindole unit and the fluorophenyl ring, respectively. The pyrrolidine ring assumes an envelope conformation with the spiro C atom as the flap. The crystal packing features weak N-HN and C-HO hydrogen bonds.

Related literature

For background to pyrrolidine derivatives, see: Raj et al. (2003); Cordell (1981); Usha et al. (2005).

Experimental

Crystal data

C₂₁H₂₀FN₃O₅
M_r = 413.40
Orthorhombic, P n a 2₁
a = 8.0265 (5) Å
b = 25.7011 (15) Å
c = 9.7763 (6) Å
V = 2016.8 (2) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 293 K
0.20 × 0.18 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004) T_min = 0.979, T_max = 0.981
22124 measured reflections
2551 independent reflections
2355 reflections with I > 2(I)
R_int = 0.022

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.132
S = 1.13
2551 reflections
271 parameters
1 restraint
H-atom parameters constrained
_max = 0.30 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2AN1ⁱ	0.86	2.34	3.127 (2)	152
C4-H4O1ⁱ	0.93	2.42	3.223 (2)	145
C9-H9BO1ⁱⁱ	0.97	2.49	3.314 (2)	142
C9-H9AO4ⁱⁱⁱ	0.97	2.51	3.443 (3)	160
Symmetry codes: (i) $[-x, -y, z-{\script{1\over 2}}]$ ; (ii) $[-x, -y, z+{\script{1\over 2}}]$ ; (iii) x+1, y, z.

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); 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: BH2472 ).

Acknowledgements

The authors thank Professor D. Velmurugan (Centre for Advanced Study in Crystallography and Biophysics, University of Madras) for providing data collection and computer facilities.

References

Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cordell, G. A. (1981). In Introduction to Alkaloids: A Biogenetic Approach. New York: Wiley International.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Raj, A. A., Raghunathan, R., SrideviKumari, M. R. & Raman, N. (2003). Bioorg. Med. Chem. 11, 407-419.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Usha, G., Selvanayagam, S., Velmurugan, D., Ravikumar, K., Jaisankar, P. & Srinivasan, P. C. (2005). Acta Cryst. E61, o2227-o2229.