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Volume 68 
Part 12 
Pages o3468-o3469  
December 2012  

Received 30 October 2012
Accepted 15 November 2012
Online 28 November 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.051
wR = 0.158
Data-to-parameter ratio = 32.0
Details
Open access

A triclinic polymorph of methyl (3R,3'S)-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, C22H21N3O4, the central pyrrolidine ring adopts a C-envelope conformation with a C atom 0.6593 (13) Å displaced from the mean plane formed by the remaining ring atoms. The indoline ring systems (r.m.s. devisations of 0.0356 and 0.0547 Å) are almost perpendicular to the mean plane of the pyrrolidine ring, making dihedral angles of 89.7 (6) and 82.5 (6)°. The acetate group attached to the pyrrolidine ring assumes an extended conformation. In the crystal,N-H...O and C-H...O hydrogen bonds connect adjacent molecules, forming an infinite tape extending along [1-1-1]. The crystal packing is further consolidated by strong [pi]-[pi] interactions with a centroid-centroid distance of 3.2585 (8) Å. The title compound is a polymorph of previously reported monoclinic structure [Ganesh et al. (2012[Ganesh, G., Yuvaraj, P. S., Govindan, E., Reddy, B. S. R. & SubbiahPandi, A. (2012). Acta Cryst. E68, o2902-o2903.]). Acta Cryst. E68, o2902-o2903].

Related literature

For background literature and the previously reported polymorph, see: Ganesh et al. (2008). For a related structure, see: Wei et al. (2011[Wei, A. C., Ali, M. A., Choon, T. S., Hemamalini, M. & Fun, H.-K. (2011). Acta Cryst. E67, o3125.]).

[Scheme 1]

Experimental

Crystal data
  • C22H21N3O4

  • Mr = 391.42

  • Triclinic, [P \overline 1]

  • a = 9.4418 (3) Å

  • b = 10.0132 (3) Å

  • c = 12.8861 (4) Å

  • [alpha] = 67.465 (2)°

  • [beta] = 88.237 (2)°

  • [gamma] = 62.842 (1)°

  • V = 985.68 (5) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.25 × 0.22 × 0.19 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.978, Tmax = 0.983

  • 23829 measured reflections

  • 8469 independent reflections

  • 5108 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.158

  • S = 1.08

  • 8469 reflections

  • 265 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3...O1i 0.86 2.10 2.9107 (12) 157
C15-H15B...O1ii 0.96 2.47 3.363 (2) 155
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+1, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. 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 (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: PV2603 ).


Acknowledgements

The authors thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection. ASP thanks the University Grants Commission, India, for a Minor Research Project.

References

Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
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]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Wei, A. C., Ali, M. A., Choon, T. S., Hemamalini, M. & Fun, H.-K. (2011). Acta Cryst. E67, o3125.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o3468-o3469   [ doi:10.1107/S160053681204706X ]

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