4′-Methyl-1H-14′,19′-dioxa-4′-aza­spiro­[indole-3,5′-tetra­cyclo­[18.4.0.02,6.08,13]tetra­cosa­ne]-1′(24′),8′,10′,12′,20′,22′-hexa­ene-2,7′(3H)-dione

Narayanan, S.; Srinivasan, T.; Purushothaman, S.; Raghunathan, R.; Velmurugan, D.

doi:10.1107/S1600536812046132

Volume 68
Part 12
Page o3344
December 2012

Received 23 October 2012
Accepted 8 November 2012
Online 14 November 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.049
wR = 0.147
Data-to-parameter ratio = 18.9
Details

4'-Methyl-1H-14',19'-dioxa-4'-azaspiro[indole-3,5'-tetracyclo[18.4.0.0^2,6.0^8,13]tetracosane]-1'(24'),8',10',12',20',22'-hexaene-2,7'(3H)-dione

Sibi Narayanan,^a Thothadri Srinivasan,^a Santhanagopalan Purushothaman,^b Raghavachary Raghunathan ^b and Devadasan Velmurugan ^a ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: shirai2011@gmail.com

In the title compound, C₂₉H₂₈N₂O₄, the indoline ring system is essentially planar, with a maximum deviation of 0.027 (2) Å; the carbonyl O atom lies 0.102 (1) Å out of the least-squares plane of the indole ring. The pyrrolidine ring adopts a C-envelope conformation, with a C atom displaced by 0.643 (2) Å from the mean plane formed by the remaining ring atoms. The pyrrolidine ring makes a dihedral angle of 86.1 (8)° with the indoline ring system. In the crystal, N-HO hydrogen bonds result in the formation of cyclic centrosymmetric dimers [R₂²(8)]. C-H [pi] interactions also occur, leading to a chain along the b-axis direction. There is a rather weak [pi] - [pi] electron interaction between the pyrrazole and benzene rings, with a centroid-centroid distance of 3.765 (1) Å.

Related literature

For background to natural and synthetic pharmacologically active pyrrolidines, see: Waldmann (1995). For related structures, see: Ganesh et al. (2012); Narayanan et al. (2012). For graph-set notation, see: Bernstein et al. (1995).

Experimental

Crystal data

C₂₉H₂₈N₂O₄
M_r = 468.53
Triclinic, $[P \overline 1]$
a = 9.4223 (3) Å
b = 10.5115 (3) Å
c = 14.1754 (5) Å
= 70.235 (2)°
= 87.309 (3)°
= 69.065 (2)°
V = 1229.67 (7) 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; Sheldrick, 2008) T_min = 0.979, T_max = 0.984
22180 measured reflections
5998 independent reflections
4260 reflections with I > 2(I)
R_int = 0.027

Refinement

R[F² > 2(F²)] = 0.049
wR(F²) = 0.147
S = 1.01
5998 reflections
317 parameters
H-atom parameters constrained
_max = 0.47 e Å^-3
_min = -0.27 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C14-C19 ring.

D-HA	D-H	HA	DA	D-HA
N2-H2AO2ⁱ	0.86	1.96	2.8105 (17)	170
C26-H26Cg4ⁱⁱ	0.93	2.91	3.617 (3)	134
Symmetry codes: (i) -x, -y+2, -z+1; (ii) -x, -y+2, -z.

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: PV2600 ).

Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. SN thanks the University Grant Commission (UGC), Government of India, New Delhi, for a Meritorious Fellowship under the SAP programme.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
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.
Narayanan, S., Srinivasan, T., Purushothaman, S., Raghunathan, R. & Velmurugan, D. (2012). Acta Cryst. E68, o3345.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Waldmann, H. (1995). Synlett, pp. 133-141.