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Volume 69 
Part 6 
Pages o825-o826  
June 2013  

Received 26 March 2013
Accepted 27 April 2013
Online 4 May 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.041
wR = 0.125
Data-to-parameter ratio = 18.1
Details
Open access

Methyl 5''-chloro-1',1''-dimethyl-2,2''-dioxodispiro[indoline-3,2'-pyrrolidine-3',3''-indoline]-4'-carboxylate

aDepartment of Physics, S.M.K. Fomra Institute of Technology, Thaiyur, Chennai 603 103, India,bIndustrial Chemistry Laboratory, Central Leather Research Institute, Adyar, Chennai 600 020, India, and cDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India
Correspondence e-mail: a_sp59@yahoo.in

In the title compound, C22H20ClN3O4, the central pyrrolidine ring adopts an envelope conformation on the N atom. The indolinone systems are individually roughly planar, with maximum deviations from their mean planes of 0.130 Å for the spiro C atom of the indolinone unit and 0.172 Å for the carbonyl C atom of the 5-chloro-1-methylindolinone unit. They make dihedral angles of 77.7 (8) and 86.1 (8)° with the mean plane through the central pyrrolidine ring. In the crystal, molecules are linked by N-H...O hydrogen bonds supported by C-H...O contacts into chains along the ab diagonal. The structure also features C-H...O hydrogen bonds, forming R22(8) and R22(16) rings and generating a three-dimensional array.

Related literature

For the biological activity of spiro-pyrrolidine derivatives, see: Obniska et al. (2003[Obniska, J., Pawlowski, M., Kolaczkowski, M., Czopek, A., Duszynska, B., Klodzinska, A., Tatarczynska, E. & Chojnacka-Wójcik, E. (2003). Pol. J. Pharmacol. 55, 553-557.]); Peddi et al. (2004[Peddi, S., Roth, B. L., Glennon, R. A. & Westkaemper, R. B. (2004). Bioorg. Med. Chem. Lett. 14, 2279-2283.]); Kaminski & Obniska (2008[Kaminski, K. & Obniska, J. (2008). Acta Pol. Pharm. 65, 457-465.]); Stylianakis et al. (2003[Stylianakis, I., Kolocouris, A., Kolocouris, N., Fytas, G., Foscolos, G. B., Padalko, E., Neyts, J. & De Clercq, E. (2003). Bioorg. Med. Chem. Lett. 13, 1699-1703.]); Waldmann (1995[Waldmann, H. (1995). Synlett, pp. 133-141.]). For the use of optically active pyrrolidines as intermediates, chiral ligands or auxiliaries in controlled asymmetric synthesis, see: Suzuki et al. (1994[Suzuki, H., Aoyagi, S. & Kibayashi, C. (1994). Tetrahedron Lett. 35, 6119-6122.]); Huryn et al. (1991[Huryn, D. M., Trost, B. M. & Fleming, I. (1991). C. Org. Synth. 1, 64-74.]). For related structures, see: Ganesh et al. (2012[Ganesh, G., Yuvaraj, P. S., Govindan, E., Reddy, B. S. R. & SubbiahPandi, A. (2012). Acta Cryst. E68, o2902-o2903.]); Wei et al. (2011[Wei, A. C., Ali, M. A., Choon, T. S., Hemamalini, M. & Fun, H.-K. (2011). Acta Cryst. E67, o3125.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]) and for hydrogen-bond motifs see Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C22H20ClN3O4

  • Mr = 425.86

  • Monoclinic, P 21 /n

  • a = 9.2543 (4) Å

  • b = 18.1387 (7) Å

  • c = 12.5147 (5) Å

  • [beta] = 105.026 (2)°

  • V = 2028.90 (14) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.22 mm-1

  • T = 293 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker APEXII CCD area detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker. (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.936, Tmax = 0.957

  • 18586 measured reflections

  • 5021 independent reflections

  • 3789 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.125

  • S = 1.06

  • 5021 reflections

  • 278 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.33 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3...O1i 0.85 (2) 2.18 (2) 2.9112 (18) 143.3 (18)
C15-H15...O1i 0.93 2.46 3.156 (2) 132
C22-H22B...O3ii 0.96 2.56 3.324 (2) 137
C5-H5...O3ii 0.93 2.61 3.499 (2) 160
C9-H9...O3iii 0.98 2.54 3.224 (2) 127
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) -x+1, -y, -z; (iii) -x, -y, -z.

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 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: SJ5312 ).


Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and BioPhysics, University of Madras, Chennai, India, for the data collection.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
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] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Ganesh, G., Yuvaraj, P. S., Govindan, E., Reddy, B. S. R. & SubbiahPandi, A. (2012). Acta Cryst. E68, o2902-o2903.  [CSD] [CrossRef] [ChemPort] [details]
Huryn, D. M., Trost, B. M. & Fleming, I. (1991). C. Org. Synth. 1, 64-74.
Kaminski, K. & Obniska, J. (2008). Acta Pol. Pharm. 65, 457-465.  [PubMed] [ChemPort]
Obniska, J., Pawlowski, M., Kolaczkowski, M., Czopek, A., Duszynska, B., Klodzinska, A., Tatarczynska, E. & Chojnacka-Wójcik, E. (2003). Pol. J. Pharmacol. 55, 553-557.  [PubMed] [ChemPort]
Peddi, S., Roth, B. L., Glennon, R. A. & Westkaemper, R. B. (2004). Bioorg. Med. Chem. Lett. 14, 2279-2283.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Stylianakis, I., Kolocouris, A., Kolocouris, N., Fytas, G., Foscolos, G. B., Padalko, E., Neyts, J. & De Clercq, E. (2003). Bioorg. Med. Chem. Lett. 13, 1699-1703.  [CrossRef] [PubMed] [ChemPort]
Suzuki, H., Aoyagi, S. & Kibayashi, C. (1994). Tetrahedron Lett. 35, 6119-6122.  [CrossRef] [ChemPort] [ISI]
Waldmann, H. (1995). Synlett, pp. 133-141.  [CrossRef]
Wei, A. C., Ali, M. A., Choon, T. S., Hemamalini, M. & Fun, H.-K. (2011). Acta Cryst. E67, o3125.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o825-o826   [ doi:10.1107/S1600536813011501 ]

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