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Volume 68 
Part 11 
Pages m1382-m1383  
November 2012  

Received 11 August 2012
Accepted 10 October 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.038
wR = 0.105
Data-to-parameter ratio = 19.2
Details
Open access

3'-Ferrocenylcarbonyl-1'-methyl-4'-phenylspiro[indeno[2,3-b]quinoxaline-11,2'-pyrrolidine]

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

In the title compound, [Fe(C5H5)(C31H24N3O)], the pyrrolidine ring makes a dihedral angle of 86.3 (3)° with the mean plane [r.m.s deviation = 0.074 (2) Å] of the indeno-quinoxaline ring system. The central pyrrolidine ring adopts a twist conformation and the two cyclopentadienyl rings adopt an eclipsed conformation. In the crystal, molecules are linked by weak C-H...N and C-H...[pi] interactions, propagating along the c and a axes, respectively.

Related literature

For the biological activity of ferrocene derivatives, see: Jaouen et al. (2004[Jaouen, G., Top, S., Vessireres, A., Leclercq, G., Vaissermann, J. & McGlinchey, M. J. (2004). Curr. Med. Chem. 11, 2505-2517.]); Biot et al. (2004[Biot, C., Dessolin, J., Richard, I. & Dive, D. (2004). J. Organomet. Chem. 689, 4678-4682.]); Fouda et al. (2007[Fouda, M. F. R., Abd-Elzaher, M. M., Abdelsamaia, R. A. & Labib, A. A. (2007). Appl. Organomet. Chem. 21, 613-625.]). For related structures, see: Satis Kumar et al. (2007[Satis Kumar, B. K., Gayathri, D., Velmurugan, D., Ravikumar, K. & Sureshbabu, A. R. (2007). Acta Cryst. E63, m1287-m1289.]); Gunasekaran et al. (2010[Gunasekaran, B., Kathiravan, S., Raghunathan, R. & Manivannan, V. (2010). Acta Cryst. E66, m1543.]); Vijayakumar et al. (2012[Vijayakumar, B., Gavaskar, D., Srinivasan, T., Raghunathan, R. & Velmurugan, D. (2012). Acta Cryst. E68, m1274.]). For puckering and asymmetry parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]); Nardelli (1983[Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.]).

[Scheme 1]

Experimental

Crystal data
  • [Fe(C5H5)(C31H24N3O)]

  • Mr = 575.47

  • Monoclinic, P 21 /n

  • a = 11.1008 (4) Å

  • b = 11.9156 (5) Å

  • c = 21.0511 (9) Å

  • [beta] = 90.944 (2)°

  • V = 2784.11 (19) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.58 mm-1

  • T = 293 K

  • 0.2 × 0.2 × 0.2 mm

Data collection
  • Bruker SMART APEX2 area-detector diffractometer

  • 26663 measured reflections

  • 7107 independent reflections

  • 4920 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.105

  • S = 1.00

  • 7107 reflections

  • 370 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C20-C25 ring.

D-H...A D-H H...A D...A D-H...A
C31-H31...N3i 0.98 2.45 3.430 (2) 176
C1-H1...Cg1ii 0.93 2.83 3.650 (2) 147
Symmetry codes: (i) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) -x+1, -y, -z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); 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: LX2263 ).


Acknowledgements

BV and DV thank the TBI X-ray Facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. BV thanks the University Grant Commission (UGC), Government of India, New Delhi, for a Meritorious Fellowship.

References

Biot, C., Dessolin, J., Richard, I. & Dive, D. (2004). J. Organomet. Chem. 689, 4678-4682.  [CrossRef] [ChemPort]
Bruker (2008). 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]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Fouda, M. F. R., Abd-Elzaher, M. M., Abdelsamaia, R. A. & Labib, A. A. (2007). Appl. Organomet. Chem. 21, 613-625.  [ISI] [CrossRef] [ChemPort]
Gunasekaran, B., Kathiravan, S., Raghunathan, R. & Manivannan, V. (2010). Acta Cryst. E66, m1543.  [CSD] [CrossRef] [details]
Jaouen, G., Top, S., Vessireres, A., Leclercq, G., Vaissermann, J. & McGlinchey, M. J. (2004). Curr. Med. Chem. 11, 2505-2517.  [ISI] [PubMed] [ChemPort]
Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.  [CrossRef] [details]
Satis Kumar, B. K., Gayathri, D., Velmurugan, D., Ravikumar, K. & Sureshbabu, A. R. (2007). Acta Cryst. E63, m1287-m1289.  [CSD] [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]
Vijayakumar, B., Gavaskar, D., Srinivasan, T., Raghunathan, R. & Velmurugan, D. (2012). Acta Cryst. E68, m1274.  [CrossRef] [details]


Acta Cryst (2012). E68, m1382-m1383   [ doi:10.1107/S1600536812042468 ]

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