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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 [sigma](C-C) = 0.004 Å
R = 0.047
wR = 0.132
Data-to-parameter ratio = 9.4
Details
Open access

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

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-H...N and C-H...O hydrogen bonds.

Related literature

For background to pyrrolidine derivatives, see: Raj et al. (2003[Raj, A. A., Raghunathan, R., SrideviKumari, M. R. & Raman, N. (2003). Bioorg. Med. Chem. 11, 407-419.]); Cordell (1981[Cordell, G. A. (1981). In Introduction to Alkaloids: A Biogenetic Approach. New York: Wiley International.]); Usha et al. (2005[Usha, G., Selvanayagam, S., Velmurugan, D., Ravikumar, K., Jaisankar, P. & Srinivasan, P. C. (2005). Acta Cryst. E61, o2227-o2229.]).

[Scheme 1]

Experimental

Crystal data
  • C21H20FN3O5

  • Mr = 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[alpha] radiation

  • [mu] = 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[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.979, Tmax = 0.981

  • 22124 measured reflections

  • 2551 independent reflections

  • 2355 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.132

  • S = 1.13

  • 2551 reflections

  • 271 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2A...N1i 0.86 2.34 3.127 (2) 152
C4-H4...O1i 0.93 2.42 3.223 (2) 145
C9-H9B...O1ii 0.97 2.49 3.314 (2) 142
C9-H9A...O4iii 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[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


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.  [ISI] [CrossRef] [ChemPort] [details]
Raj, A. A., Raghunathan, R., SrideviKumari, M. R. & Raman, N. (2003). Bioorg. Med. Chem. 11, 407-419.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Usha, G., Selvanayagam, S., Velmurugan, D., Ravikumar, K., Jaisankar, P. & Srinivasan, P. C. (2005). Acta Cryst. E61, o2227-o2229.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o278  [ doi:10.1107/S1600536813001578 ]

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