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Volume 69 
Part 9 
Page o1466  
September 2013  

Received 13 August 2013
Accepted 15 August 2013
Online 23 August 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.042
wR = 0.124
Data-to-parameter ratio = 13.9
Details
Open access

1',1''-Dimethyl-4'-(4-methylphenyl)dispiro[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, C31H30N4O, the central pyrrolidine ring adopts an envelope conformation with the methylene C atom being the flap. The quinoxaline and indane rings are each planar, having r.m.s. deviations of 0.030 and 0.050 Å, respectively. The pyrrolidine ring mean plane forms dihedral angles of 88.25 (1) and 83.76 (1)° with the quinoxaline and indane rings, respectively. Intramolecular C-H...O and C-H...N interactions are observed. In the crystal, C-H...[pi] interactions lead to helical supramolecular chains along the b-axis direction.

Related literature

For the importance of pyrrolidine compounds, see: Witherup et al. (1995[Witherup, K., Ranson, R. W., Graham, A. C., Barnard, A. M., Salvatore, M. J., Limma, W. C., Anderson, P. S., Pitzenberger, S. M. & Varga, S. L. (1995). J. Am. Chem. Soc. 117, 6682-6685.]). For the importance of heterocycles with piperidine sub-structures, see: El-Subbagh et al. (2000[El-Subbagh, H. I., Abu-Zaid, S. M., Mahran, M. A., Badria, F. A. & Al-Obaid, A. M. (2000). J. Med. Chem. 43, 2915-2921.]); Dimmock et al. (2001[Dimmock, J. R., Padmanilayam, M. P., Puthucode, R. N., Nazarali, A. J., Motaganahalli, N. L., Zello, G. A., Quail, J. W., Oloo, E. O., Kraatz, H. B., Prisciak, J. S., Allen, T. M., Santos, C. L., Balzarini, J., De Clercq, E. & Manavathu, E. K. (2001). J. Med. Chem. 44, 586-593.]); Lee et al. (2001[Lee, H. K., Chun, J. S. & Pak, C. S. (2001). Tetrahedron Lett. 42, 3483-3486.]). For additional conformation analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C31H30N4O

  • Mr = 474.59

  • Monoclinic, C 2/c

  • a = 22.3183 (7) Å

  • b = 14.4411 (5) Å

  • c = 17.2474 (6) Å

  • [beta] = 116.547 (2)°

  • V = 4972.8 (3) Å3

  • Z = 8

  • 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

  • 22517 measured reflections

  • 4550 independent reflections

  • 3034 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.124

  • S = 1.04

  • 4550 reflections

  • 327 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.12 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3...O1 0.98 2.36 2.804 (2) 107
C41-H41B...N3 0.97 2.39 2.980 (2) 119
C11-H11...Cg1i 0.93 2.94 3.692 (2) 139
Symmetry code: (i) [x, -y-1, 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: TK5247 ).


Acknowledgements

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

References

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]
Dimmock, J. R., Padmanilayam, M. P., Puthucode, R. N., Nazarali, A. J., Motaganahalli, N. L., Zello, G. A., Quail, J. W., Oloo, E. O., Kraatz, H. B., Prisciak, J. S., Allen, T. M., Santos, C. L., Balzarini, J., De Clercq, E. & Manavathu, E. K. (2001). J. Med. Chem. 44, 586-593.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
El-Subbagh, H. I., Abu-Zaid, S. M., Mahran, M. A., Badria, F. A. & Al-Obaid, A. M. (2000). J. Med. Chem. 43, 2915-2921.  [ISI] [CrossRef] [PubMed] [ChemPort]
Lee, H. K., Chun, J. S. & Pak, C. S. (2001). Tetrahedron Lett. 42, 3483-3486.  [ISI] [CrossRef] [ChemPort]
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]
Witherup, K., Ranson, R. W., Graham, A. C., Barnard, A. M., Salvatore, M. J., Limma, W. C., Anderson, P. S., Pitzenberger, S. M. & Varga, S. L. (1995). J. Am. Chem. Soc. 117, 6682-6685.  [CrossRef] [ChemPort] [ISI]


Acta Cryst (2013). E69, o1466  [ doi:10.1107/S1600536813022964 ]

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