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Volume 69 
Part 8 
Page o1214  
August 2013  

Received 1 July 2013
Accepted 3 July 2013
Online 6 July 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.122
Data-to-parameter ratio = 22.6
Details
Open access

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

aPost Graduate & Research Department of Physics, Agurchand Manmull Jain College, Chennai 600 114, India, and bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: seshadri_pr@yahoo.com

In the title compound, C27H25ClN2O3, the methylpyrrolidine ring adopts an envelope conformation with the N atom at the flap. The mean plane of the pyrrolidine ring makes dihedral angles of 82.1 (1), 84.4 (1) and 79.8 (1)°, respectively, with the adjacent benzene ring, the mean plane of the indoline ring system and the phenyl ring. The molecular structure is stabilized by intramolecular C-H...O hydrogen bonds. In the crystal, molecules are linked into chains along [101] by N-H...O hydrogen bonds. C-H...[pi] interactions are observed between the chains.

Related literature

For the biological activity of pyrrolidine-containing compounds and their use in catalysis, see: Witherup et al. (1995[Witherup, K., Ranson, R. W., Graham, A. C., Barnard, A. M., Salvatore, M. J., Limma, W. C., Anderson, P. S., Pitzenberger, S. M. & Varga, S. L. (1995). J. Am. Chem. Soc. 117, 6682-6685.]). For the biological activity of oxindole derivatives, see: Glover et al. (1998[Glover, V., Halket, J. M., Watkins, P. J., Clow, A., Goodwin, B. L. & Sandler, M. (1998). J. Neurochem. 51, 656-659.]). For puckering and asymmetry parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]); Nardelli (1983[Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.]).

[Scheme 1]

Experimental

Crystal data
  • C27H25ClN2O3

  • Mr = 460.94

  • Monoclinic, P 21 /n

  • a = 13.0887 (6) Å

  • b = 14.0869 (7) Å

  • c = 13.3521 (7) Å

  • [beta] = 113.524 (2)°

  • V = 2257.25 (19) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.20 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). SADABS. Bruker AXS Ins., Madison, Wisconsin, USA.]) Tmin = 0.953, Tmax = 0.960

  • 29103 measured reflections

  • 6735 independent reflections

  • 4875 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.122

  • S = 0.98

  • 6735 reflections

  • 298 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.33 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C11-C16 ring.

D-H...A D-H H...A D...A D-H...A
N2-H2A...O2i 0.86 2.06 2.9004 (15) 164
C5-H5...O1 0.93 2.31 3.168 (2) 153
C18-H18A...O1 0.97 2.54 3.2469 (18) 130
C24-H24...O3 0.93 2.47 3.1650 (19) 132
C23-H23...Cg3ii 0.93 2.77 3.600 (2) 149
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5288 ).


Acknowledgements

The authors thank Dr Babu Varghese, SAIF, IIT-Madras, India, for the data collection.

References

Bruker (2004). SADABS. Bruker AXS Ins., Madison, Wisconsin, USA.
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Glover, V., Halket, J. M., Watkins, P. J., Clow, A., Goodwin, B. L. & Sandler, M. (1998). J. Neurochem. 51, 656-659.  [CrossRef] [Web of Science]
Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.  [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Witherup, K., Ranson, R. W., Graham, A. C., Barnard, A. M., Salvatore, M. J., Limma, W. C., Anderson, P. S., Pitzenberger, S. M. & Varga, S. L. (1995). J. Am. Chem. Soc. 117, 6682-6685.  [CrossRef] [Web of Science]


Acta Cryst (2013). E69, o1214  [ doi:10.1107/S1600536813018424 ]

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