A triclinic polymorph of methyl (3R,3′S)-1′,1′′-dimethyl-2,2′′-dioxodispiro­[indoline-3,2′-pyrrolidine-3′,3′′-indoline]-4′-carboxyl­ate

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

doi:10.1107/S160053681204706X

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 (C-C) = 0.002 Å
R = 0.051
wR = 0.158
Data-to-parameter ratio = 32.0
Details

A triclinic polymorph of methyl (3R,3'S)-1',1''-dimethyl-2,2''-dioxodispiro[indoline-3,2'-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, 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-HO and C-HO 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). 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).

Experimental

Crystal data

C₂₂H₂₁N₃O₄
M_r = 391.42
Triclinic, $[P \overline 1]$
a = 9.4418 (3) Å
b = 10.0132 (3) Å
c = 12.8861 (4) Å
= 67.465 (2)°
= 88.237 (2)°
= 62.842 (1)°
V = 985.68 (5) Å³
Z = 2
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
23829 measured reflections
8469 independent reflections
5108 reflections with I > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.051
wR(F²) = 0.158
S = 1.08
8469 reflections
265 parameters
H-atom parameters constrained
_max = 0.29 e Å^-3
_min = -0.27 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H3O1ⁱ	0.86	2.10	2.9107 (12)	157
C15-H15BO1ⁱⁱ	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); 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: 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.
Ganesh, G., Yuvaraj, P. S., Govindan, E., Reddy, B. S. R. & SubbiahPandi, A. (2012). Acta Cryst. E68, o2902-o2903.
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., Hemamalini, M. & Fun, H.-K. (2011). Acta Cryst. E67, o3125.

organic compounds