1′-Methyl-4′-(4-methyl­phen­yl)dispiro­[1-benzopyran-3(4H),3′-pyrrolidine-2′,3′′-indoline]-2,2′′-dione

Lakshmanan, D.; Murugavel, S.; Kannan, D.; Bakthadoss, M.

doi:10.1107/S1600536811051440

Volume 68
Part 1
Page o11
January 2012

Received 28 November 2011
Accepted 29 November 2011
Online 3 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R = 0.050
wR = 0.153
Data-to-parameter ratio = 24.2
Details

1'-Methyl-4'-(4-methylphenyl)dispiro[1-benzopyran-3(4H),3'-pyrrolidine-2',3''-indoline]-2,2''-dione

D. Lakshmanan,^a S. Murugavel,^b ^* D. Kannan ^c and M. Bakthadoss ^c ⁺

^aDepartment of Physics, C. Abdul Hakeem College of Engineering & Technology, Melvisharam, Vellore 632 509, India,^bDepartment of Physics, Thanthai Periyar Government Institute of Technology, Vellore 632 002, India, and ^cDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
Correspondence e-mail: smurugavel27@gmail.com

In the title compound, C₂₇H₂₄N₂O₃, the pyrroldine ring adopts a twist conformation, while the six-membered pyranone ring of the coumarin ring system is in a sofa conformation. In the crystal, pairs of N-HO hydrogen bonds link the molecules into inversion R₂²(8) dimers. These dimers are further connected via C-HO hydrogen bonds.

Related literature

For applications of pyrrolidine derivatives, see: Huryn et al. (1991); Suzuki et al. (1994); Waldmann (1995). For ring puckering parameters, see: Cremer & Pople (1975) and for asymmetry parameters, see: Duax et al. (1976). For closely related pyrrolidine structures, see: Selvanayagam et al. (2011); Ali et al. (2010). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₂₇H₂₄N₂O₃
M_r = 424.48
Monoclinic, P 2₁ /c
a = 10.4543 (3) Å
b = 14.6018 (4) Å
c = 14.7266 (4) Å
= 104.043 (2)°
V = 2180.85 (10) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 293 K
0.26 × 0.23 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.978, T_max = 0.985
30221 measured reflections
7055 independent reflections
4544 reflections with I > 2(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.050
wR(F²) = 0.153
S = 1.02
7055 reflections
291 parameters
H-atom parameters constrained
_max = 0.31 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2O1ⁱ	0.86	2.02	2.874 (1)	174
C5-H5BO3ⁱⁱ	0.96	2.59	3.407 (2)	143
Symmetry codes: (i) -x+2, -y+2, -z; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); 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: BT5735 ).

Acknowledgements

The authors thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help with the data collection.

References

Ali, M. A., Ismail, R., Tan, S. C., Yeap, C. S. & Fun, H.-K. (2010). Acta Cryst. E66, o2533-o2534.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Duax, W. L., Weeks, C. M. & Rohrer, D. C. (1976). Topics in Stereochemistry, Vol. 9, edited by E. L. Eliel & N. L. Allinger, pp. 271-383. New York: John Wiley.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Huryn, D. M., Trost, B. M. & Fleming, I. (1991). Comp. Org. Synth. 1, 64-74.
Selvanayagam, S., Ravikumar, K., Saravanan, P. & Raghunathan, R. (2011). Acta Cryst. E67, o751.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Suzuki, H., Aoyagi, S. & Kibayashi, C. (1994). Tetrahedron Lett. 35, 6119-6122.
Waldmann, H. (1995). Synlett. pp. 133-141.

organic compounds