4-Ferrocenyl-1-methyl-3-benzoyl­spiro­[pyrrolidine-2,11′-indeno­[1,2-b]quinoxaline]

Vijayakumar, B.; Sureshbabu, A.R.; Gavaskar, D.; Raghunathan, R.; Velmurugan, D.

doi:10.1107/S1600536812048349

Volume 68
Part 12
Pages m1576-m1577
December 2012

Received 17 November 2012
Accepted 25 November 2012
Online 30 November 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R = 0.036
wR = 0.106
Data-to-parameter ratio = 18.7
Details

4-Ferrocenyl-1-methyl-3-benzoylspiro[pyrrolidine-2,11'-indeno[1,2-b]quinoxaline]

B. Vijayakumar,^a A. R. Sureshbabu,^b D. Gavaskar,^b R. Raghunathan ^b and D. Velmurugan ^a ^*

^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 adopts a twist conformation. The pyrrolidine ring is almost perpendicular to the indenoquinoxaline ring system, making a dihedral angle of 84.44 (5)°. The cyclopentadienyl rings of the ferrocene moiety adopt an eclipsed conformation. The crystal packing features weak C-HN and C-H [pi] interactions.

Related literature

For the biological activity of ferrocene derivatives, see: Jaouen et al. (2004); Biot et al. (2004); Fouda et al. (2007). For related structures, see: Kamala et al. (2009); Gunasekaran et al. (2010); Vijayakumar et al. (2012); For puckering and asymmetry parameters, see: Cremer & Pople (1975); Nardelli (1983).

Experimental

Crystal data

[Fe(C₅H₅)(C₃₁H₂₄N₃O)]
M_r = 575.47
Monoclinic, P 2₁ /c
a = 10.8091 (18) Å
b = 12.326 (2) Å
c = 20.989 (3) Å
= 100.654 (8)°
V = 2748.2 (8) Å³
Z = 4
Mo K radiation
= 0.58 mm^-1
T = 293 K
0.2 × 0.2 × 0.2 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) T_min = 0.890, T_max = 0.890
27206 measured reflections
6927 independent reflections
5624 reflections with I > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.036
wR(F²) = 0.106
S = 1.01
6927 reflections
371 parameters
H-atom parameters constrained
_max = 0.30 e Å^-3
_min = -0.44 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C20-C24 ring.

D-HA	D-H	HA	DA	D-HA
C25-H25N3	0.93	2.55	3.351 (2)	144
C35-H35Cg3ⁱ	0.93	2.83	3.616 (2)	143
Symmetry code: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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: BT6861 ).

Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. BV also thanks the University Grants 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.
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Fouda, M. F. R., Abd-Elzaher, M. M., Abdelsamaia, R. A. & Labib, A. A. (2007). Appl. Organomet. Chem. 21, 613-625.
Gunasekaran, B., Kathiravan, S., Raghunathan, R. & Manivannan, V. (2010). Acta Cryst. E66, m1543.
Jaouen, G., Top, S., Vessireres, A., Leclercq, G., Vaissermann, J. & McGlinchey, M. J. (2004). Curr. Med. Chem. 11, 2505-2517.
Kamala, E. T. S., Nirmala, S., Sudha, L., Kathiravan, S. & Raghunathan, R. (2009). Acta Cryst. E65, m687-m688.
Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Vijayakumar, B., Gavaskar, D., Srinivasan, T., Raghunathan, R. & Velmurugan, D. (2012). Acta Cryst. E68, m1382-m1383.

metal-organic compounds