3′-[Hy­droxy(4-oxo-4H-chromen-3-yl)meth­yl]-2-oxospiro­[indoline-3,2′-pyrrolidine]-3′-carbonitrile

Govindan, E.; SakthiMurugesan, K.; SubbiahPandi, A.; Yuvaraj, P.; Reddy, B.S.R.

doi:10.1107/S1600536811053098

Volume 68
Part 1
Pages o136-o137
January 2012

Received 12 October 2011
Accepted 9 December 2011
Online 17 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R = 0.039
wR = 0.106
Data-to-parameter ratio = 17.7
Details

3'-[Hydroxy(4-oxo-4H-chromen-3-yl)methyl]-2-oxospiro[indoline-3,2'-pyrrolidine]-3'-carbonitrile

E. Govindan,^a K. SakthiMurugesan,^a A. SubbiahPandi,^a ^* P. Yuvaraj ^b and Boreddy S. R. Reddy ^b

^aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, and ^bIndustrial Chemistry Laboratory, Central Leather Research Institute, Adyar, Chennai 600 020, India
Correspondence e-mail: a_sp59@yahoo.in

In the title compound, C₂₃H₁₉N₃O₄, the pyran ring adopts a half-chair conformation, while the pyrrolidine (with a C atom as the flap atom) and the five-membered ring in the indoline (with a C atom as the flap atom) ring system adopt slight envelope conformations. The pyrrolidine ring makes dihedral angles of 83.3 (1) and 60.4 (1)° with the mean plane through all non-H atoms of the indoline and chromene ring systems, respectively. In the crystal, molecules are connected by two unique N-HO and O-HO hydrogen-bonding interactions, which form centrosymmetric patterns described by graph-set motifs R₂²(18) and R₂²(14). These two motifs combine to form a hydrogen-bonded chain which propagates in the a-axis direction. The crystal structure is also stablized by C-HO interactions and by aromatic [pi] - [pi] stacking interactions between the pyran and benzene rings of neighbouring molecules [centroid-centroid distance = 3.755 (1) Å and slippage = 1.371 (2) Å].

Related literature

For general background to the biological use of pyrrolidine derivatives, see: Pettersson et al. (2011); Bello et al. (2010). For ring puckering parameters, see: Cremer & Pople (1975) and for asymmetry parameters, see: Nardelli (1983). For the structure of another pyrrolidine derivatie, see: Selvanayagam et al. (2011).

Experimental

Crystal data

C₂₃H₁₉N₃O₄
M_r = 401.41
Triclinic, $[P \overline 1]$
a = 9.3483 (7) Å
b = 10.2256 (9) Å
c = 10.9080 (9) Å
= 71.832 (5)°
= 88.309 (5)°
= 78.248 (5)°
V = 969.32 (14) Å³
Z = 2
Mo K radiation
= 0.10 mm^-1
T = 293 K
0.20 × 0.20 × 0.19 mm

Data collection

Bruker APEXII CCD area detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.981, T_max = 0.982
17643 measured reflections
4841 independent reflections
3374 reflections with I > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.106
S = 1.02
4841 reflections
273 parameters
H-atom parameters constrained
_max = 0.22 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2AO2ⁱ	0.86	2.01	2.8479 (14)	164
O3-H3AO4ⁱⁱ	0.82	1.97	2.7631 (14)	164
C23-H23O3ⁱⁱⁱ	0.93	2.58	3.2761 (18)	133
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y+1, -z+1; (iii) x-1, y, z.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); 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, 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: NK2121 ).

Acknowledgements

The authors thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection.

References

Bello, C., Cea, M., Dal Bello, G., Garuti, A., Rocco, I., Cirmena, G., Moran, E., Nahimana, A., Duchosal, M. A., Fruscione, F., Pronzato, P., Grossi, F., Patrone, F., Ballestro, A., Dupuis, M., Sordat, B., Nencioni, A. & Vogel, P. (2010). Bioorg. Med. Chem. 18, 3320-3334.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.
Pettersson, M., Campbell, B. M., Dounary, A. B., Gray, D. L., Xie, L., O'Donnell, C. J., Stratman, N. C., Zoski, K., Drummond, E., Bora, G., Probert, A. & Whisman, T. (2011). Bioorg. Med. Chem. Lett. 21, 865-868.
Selvanayagam, S., Sridhar, B., Ravikumar, K., Saravanan, P. & Raghunathan, R. (2011). Acta Cryst. E67, o629.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.