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Volume 69 
Part 9 
Page o1433  
September 2013  

Received 5 August 2013
Accepted 8 August 2013
Online 14 August 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.050
wR = 0.138
Data-to-parameter ratio = 21.1
Details
Open access

1',1''-Dimethyl-4'-phenyldispiro[11H-indeno[1,2-b]quinoxaline-11,2'-pyrrolidine-3',3''-piperidin]-4''-one

aDepartment of Physics, The Madura College, Madurai 625 011, India,bDepartment of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, India, and cDepartment of Food Science and Technology, University of Ruhuna, Mapalana, Kamburupitiya 81100, Sri Lanka
Correspondence e-mail: plakshmannilantha@ymail.com

In the title compound, C30H28N4O, the central pyrrolidine ring adopts an envelope conformation with the CH2 C atom as the flap. The quinoxaline and indene ring systems are planar, with r.m.s. deviations of 0.0165 and 0.0181 Å, respectively. The pyrrolidine ring mean plane forms dihedral angles of 88.84 (1) and 86.14 (1)° with the quinoxaline and indene ring systems, respectively. A weak intramolecular C-H...N interaction is observed. In the crystal, C-H...O interactions lead to helical supramolecular chains along the b axis having a C(9) motif.

Related literature

For the importance of spiro compounds, see: Kobayashi et al. (1991[Kobayashi, J., Tsuda, M., Agemi, K. & Vacelet, J. (1991). Tetrahedron, 47, 6617-6622.]); James et al. (1991[James, D., Kunze, H. B. & Faulker, D. (1991). J. Nat. Prod. 54, 1137-1140.]). For the importance of pyrrolidine derivatives, see: Amal Raj et al. (2003[Amal Raj, A., Raghunathan, R., Sridevi Kumari, M. R. & Raman, N. (2003). Bioorg. Med. Chem. 11, 407-409.]). For conformation analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For a related structure, see: Selvanayagam et al. (2011[Selvanayagam, S., Sridhar, B., Ravikumar, K., Saravanan, P. & Raghunathan, R. (2011). Acta Cryst. E67, o629.]). For hydrogen-bond motifs, 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
  • C30H28N4O

  • Mr = 460.56

  • Monoclinic, P 21 /c

  • a = 13.4470 (6) Å

  • b = 8.4557 (4) Å

  • c = 20.8580 (9) Å

  • [beta] = 90.195 (2)°

  • V = 2371.62 (19) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 293 K

  • 0.21 × 0.19 × 0.18 mm

Data collection
  • Bruker Kappa APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.]) Tmin = 0.967, Tmax = 0.974

  • 28395 measured reflections

  • 6662 independent reflections

  • 4394 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.138

  • S = 1.02

  • 6662 reflections

  • 316 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C41-H41B...N3 0.97 2.39 2.9475 (18) 116
C9-H9...O1i 0.93 2.53 3.3564 (18) 148
Symmetry code: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin,USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5246 ).


Acknowledgements

JS and RAN thank the management of Madura College for their encouragement and support. RRK thanks theDST, New Delhi, for funds under the fast-track scheme (No. SR/FT/CS-073/2009)

References

Amal Raj, A., Raghunathan, R., Sridevi Kumari, M. R. & Raman, N. (2003). Bioorg. Med. Chem. 11, 407-409.  [PubMed]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin,USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
James, D., Kunze, H. B. & Faulker, D. (1991). J. Nat. Prod. 54, 1137-1140.  [CrossRef] [PubMed] [ChemPort] [ISI]
Kobayashi, J., Tsuda, M., Agemi, K. & Vacelet, J. (1991). Tetrahedron, 47, 6617-6622.  [CrossRef] [ChemPort] [ISI]
Selvanayagam, S., Sridhar, B., Ravikumar, K., Saravanan, P. & Raghunathan, R. (2011). Acta Cryst. E67, o629.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1433  [ doi:10.1107/S160053681302223X ]

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