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

Vijayakumar, B.; Gavaskar, D.; Srinivasan, T.; Raghunathan, R.; Velmurugan, D.

doi:10.1107/S1600536812042468

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 (C-C) = 0.003 Å
R = 0.038
wR = 0.105
Data-to-parameter ratio = 19.2
Details

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

B. Vijayakumar,^a D. Gavaskar,^b T. Srinivasan,^a 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 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-HN 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); Biot et al. (2004); Fouda et al. (2007). For related structures, see: Satis Kumar et al. (2007); 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 /n
a = 11.1008 (4) Å
b = 11.9156 (5) Å
c = 21.0511 (9) Å
= 90.944 (2)°
V = 2784.11 (19) Å³
Z = 4
Mo K radiation
= 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(I)
R_int = 0.027

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.105
S = 1.00
7107 reflections
370 parameters
H-atom parameters constrained
_max = 0.34 e Å^-3
_min = -0.31 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C20-C25 ring.

D-HA	D-H	HA	DA	D-HA
C31-H31N3ⁱ	0.98	2.45	3.430 (2)	176
C1-H1Cg1ⁱⁱ	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); 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, 1997); 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: 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.
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
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.
Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.
Satis Kumar, B. K., Gayathri, D., Velmurugan, D., Ravikumar, K. & Sureshbabu, A. R. (2007). Acta Cryst. E63, m1287-m1289.
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, m1274.