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Volume 69 
Part 3 
Page o441  
March 2013  

Received 22 January 2013
Accepted 19 February 2013
Online 23 February 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.047
wR = 0.135
Data-to-parameter ratio = 17.3
Details
Open access

A diastereomer of methyl (1R,3'S)-1',1''-dimethyl-2,2''-dioxo-2H-dispiro[acenaphthylene-1,2'-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, C26H22N2O4, the central pyrrolidine ring adopts a twist conformation and the cyclopentane ring of the dihydroacenapthylene group adopts an envelope conformation with the spiro C atom as the flap. The naphthalene ring system of the dihydroacenaphthylene group forms dihedral angles of 83.4 (9) and 61.3 (7)°, respectively, with the mean planes of the pyrrolidine and indole rings. The crystal packing is stabilized by intermolecular C-H...O hydrogen bonds. The title compound is a diastereomer of a previously reported structure.

Related literature

For background literature and the previously reported diastereomer, see: Ganesh et al. (2013[Ganesh, G., Yuvaraj, P. S., Divakara, C., Reddy, B. S. R. & SubbiahPandi, A. (2013). Acta Cryst. E69, o235.]). For a related structure, see: Wei et al. (2012[Wei, A. C., Ali, M. A., Choon, T. S., Arshad, S. & Razak, I. A. (2012). Acta Cryst. E68, o1340-o1341.]). For information on ring conformations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C26H22N2O4

  • Mr = 426.46

  • Orthorhombic, P b c n

  • a = 27.2997 (15) Å

  • b = 9.7923 (6) Å

  • c = 15.8557 (10) Å

  • V = 4238.7 (4) Å3

  • Z = 8

  • 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, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.978, Tmax = 0.983

  • 23813 measured reflections

  • 5039 independent reflections

  • 3022 reflections with I > 2[sigma](I)

  • Rint = 0.033

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

  • wR(F2) = 0.135

  • S = 1.02

  • 5039 reflections

  • 292 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C1-H1B...O3i 0.96 2.48 3.299 (3) 143
C20-H20...O3ii 0.93 2.59 3.403 (3) 146
Symmetry codes: (i) [x, -y, z-{\script{1\over 2}}]; (ii) [-x+1, y, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT; 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: BT6885 ).


Acknowledgements

ASP thanks the University Grants Commission, India, for a Minor research Project.

References

Bruker (2008). APEX2, SADABS 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., Divakara, C., Reddy, B. S. R. & SubbiahPandi, A. (2013). Acta Cryst. E69, o235.  [CrossRef] [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., Arshad, S. & Razak, I. A. (2012). Acta Cryst. E68, o1340-o1341.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o441  [ doi:10.1107/S1600536813004868 ]

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