A diastereomer of methyl (1R,3′S)-1′,1′′-dimethyl-2,2′′-dioxo-2H-dispiro­[ace­naphthyl­ene-1,2′-pyrrolidine-3′,3′′-indoline]-4′-carboxyl­ate

Ganesh, G.; Yuvaraj, P.S.; Kannan, P.S.; Reddy, B.S.R.; SubbiahPandi, A.

doi:10.1107/S1600536813004868

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 (C-C) = 0.003 Å
R = 0.047
wR = 0.135
Data-to-parameter ratio = 17.3
Details

A diastereomer of methyl (1R,3'S)-1',1''-dimethyl-2,2''-dioxo-2H-dispiro[acenaphthylene-1,2'-pyrrolidine-3',3''-indoline]-4'-carboxylate

Gnanavelu Ganesh,^a PanneerSelvam Yuvaraj,^b Piskala Subburaman Kannan,^a Boreddy Siva Rami Reddy ^b and Arunachalathevar SubbiahPandi ^c ^*

^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-HO 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). For a related structure, see: Wei et al. (2012). For information on ring conformations, see: Cremer & Pople (1975).

Experimental

Crystal data

C₂₆H₂₂N₂O₄
M_r = 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 radiation
= 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) T_min = 0.978, T_max = 0.983
23813 measured reflections
5039 independent reflections
3022 reflections with I > 2(I)
R_int = 0.033

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.135
S = 1.02
5039 reflections
292 parameters
H-atom parameters constrained
_max = 0.17 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C1-H1BO3ⁱ	0.96	2.48	3.299 (3)	143
C20-H20O3ⁱⁱ	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); cell refinement: SAINT; data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

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.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Ganesh, G., Yuvaraj, P. S., Divakara, C., Reddy, B. S. R. & SubbiahPandi, A. (2013). Acta Cryst. E69, o235.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Wei, A. C., Ali, M. A., Choon, T. S., Arshad, S. & Razak, I. A. (2012). Acta Cryst. E68, o1340-o1341.

organic compounds