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Volume 69 
Part 2 
Page o235  
February 2013  

Received 22 December 2012
Accepted 5 January 2013
Online 12 January 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.038
wR = 0.103
Data-to-parameter ratio = 13.9
Details
Open access

rac-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 pyrrolidine ring adopts a twisted conformation and the other five-membered rings adopt envelope conformations with the spiro C atoms as the flap atoms. The naphthalene ring system of the dihydroacenaphthylene group forms dihedral angles of 89.2 (9) and 75.5 (6)° with the pyrrolidine and indole rings, respectively. The pyrrolidine ring makes a dihedral angle of 80.1 (9)° with the indole ring. In the crystal, molecules are linked by weak C-H...O hydrogen bonds, forming chains along the b-axis direction.

Related literature

For the biological activity of naphthalene derivatives, see: Wiltz et al. (1998[Wiltz, B. A., Henderson, G. & Chen, J. (1998). Environ. Entomol. 27, 936-940.]); Wright et al. (2000[Wright, M. S., Lax, A. R., Henderson, G. & Chen, J. A. (2000). Mycologia, 92, 42-45.]); Varma et al. (1994[Varma, A., Kolli, B. K., Paul, J., Saxena, S. & Konig, H. (1994). FEMS Microbiol. Rev. 15, 9-28.]). 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 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

  • Monoclinic, P 21 /c

  • a = 15.4839 (4) Å

  • b = 9.5832 (2) Å

  • c = 15.6375 (4) Å

  • [beta] = 115.184 (1)°

  • V = 2099.81 (9) Å3

  • Z = 4

  • 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 = 0.977, Tmax = 0.983

  • 19264 measured reflections

  • 4057 independent reflections

  • 3017 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.103

  • S = 1.03

  • 4057 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
C10-H10...O2i 0.93 2.60 3.268 (2) 130
Symmetry code: (i) [x, -y+{\script{3\over 2}}, 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 (Bruker, 2008[Bruker (2008). APEX2, SADABS 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 (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: LX2278 ).


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]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Varma, A., Kolli, B. K., Paul, J., Saxena, S. & Konig, H. (1994). FEMS Microbiol. Rev. 15, 9-28.  [ChemPort]
Wei, A. C., Ali, M. A., Choon, T. S., Arshad, S. & Razak, I. A. (2012). Acta Cryst. E68, o1340-o1341.  [CSD] [CrossRef] [details]
Wiltz, B. A., Henderson, G. & Chen, J. (1998). Environ. Entomol. 27, 936-940.  [ChemPort]
Wright, M. S., Lax, A. R., Henderson, G. & Chen, J. A. (2000). Mycologia, 92, 42-45.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o235  [ doi:10.1107/S1600536813000470 ]

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