[Journal logo]

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 [sigma](C-C) = 0.003 Å
R = 0.049
wR = 0.147
Data-to-parameter ratio = 18.9
Details
Open access

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

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-H...O 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[Waldmann, H. (1995). Synlett, pp. 133-141.]). For related structures, see: Ganesh et al. (2012[Ganesh, G., Yuvaraj, P. S., Govindan, E., Reddy, B. S. R. & SubbiahPandi, A. (2012). Acta Cryst. E68, o2902-o2903.]); Narayanan et al. (2012[Narayanan, S., Srinivasan, T., Purushothaman, S., Raghunathan, R. & Velmurugan, D. (2012). Acta Cryst. E68, o3345.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C29H28N2O4

  • Mr = 468.53

  • Triclinic, [P \overline 1]

  • a = 9.4223 (3) Å

  • b = 10.5115 (3) Å

  • c = 14.1754 (5) Å

  • [alpha] = 70.235 (2)°

  • [beta] = 87.309 (3)°

  • [gamma] = 69.065 (2)°

  • V = 1229.67 (7) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) Tmin = 0.979, Tmax = 0.984

  • 22180 measured reflections

  • 5998 independent reflections

  • 4260 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.147

  • S = 1.01

  • 5998 reflections

  • 317 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.47 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C14-C19 ring.

D-H...A D-H H...A D...A D-H...A
N2-H2A...O2i 0.86 1.96 2.8105 (17) 170
C26-H26...Cg4ii 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[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 2012)[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]; software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


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.  [CrossRef] [ChemPort] [ISI]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Ganesh, G., Yuvaraj, P. S., Govindan, E., Reddy, B. S. R. & SubbiahPandi, A. (2012). Acta Cryst. E68, o2902-o2903.  [CSD] [CrossRef] [ChemPort] [details]
Narayanan, S., Srinivasan, T., Purushothaman, S., Raghunathan, R. & Velmurugan, D. (2012). Acta Cryst. E68, o3345.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Waldmann, H. (1995). Synlett, pp. 133-141.  [CrossRef]


Acta Cryst (2012). E68, o3344  [ doi:10.1107/S1600536812046132 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.