rac-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.; Divakara, C.; Reddy, B.S.R.; SubbiahPandi, A.

doi:10.1107/S1600536813000470

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 (C-C) = 0.002 Å
R = 0.038
wR = 0.103
Data-to-parameter ratio = 13.9
Details

rac-Methyl (1R,3'S)-1',1''-dimethyl-2,2''-dioxo-2H-dispiro[acenaphthylene-1,2'-pyrrolidine-3',3''-indoline]-4'-carboxylate

G. Ganesh,^a Panneer Selvam Yuvaraj,^b Chinthalapuri Divakara,^b Boreddy S. R. Reddy ^b and A. 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 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-HO hydrogen bonds, forming chains along the b-axis direction.

Related literature

For the biological activity of naphthalene derivatives, see: Wiltz et al. (1998); Wright et al. (2000); Varma et al. (1994). For a related structure, see: Wei et al. (2012). For ring conformations, see: Cremer & Pople (1975).

Experimental

Crystal data

C₂₆H₂₂N₂O₄
M_r = 426.46
Monoclinic, P 2₁ /c
a = 15.4839 (4) Å
b = 9.5832 (2) Å
c = 15.6375 (4) Å
= 115.184 (1)°
V = 2099.81 (9) Å³
Z = 4
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 = 0.977, T_max = 0.983
19264 measured reflections
4057 independent reflections
3017 reflections with I > 2(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.103
S = 1.03
4057 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
C10-H10O2ⁱ	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); cell refinement: SAINT (Bruker, 2008); 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: 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.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Varma, A., Kolli, B. K., Paul, J., Saxena, S. & Konig, H. (1994). FEMS Microbiol. Rev. 15, 9-28.
Wei, A. C., Ali, M. A., Choon, T. S., Arshad, S. & Razak, I. A. (2012). Acta Cryst. E68, o1340-o1341.
Wiltz, B. A., Henderson, G. & Chen, J. (1998). Environ. Entomol. 27, 936-940.
Wright, M. S., Lax, A. R., Henderson, G. & Chen, J. A. (2000). Mycologia, 92, 42-45.

organic compounds