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Volume 69 
Part 9 
Pages m512-m513  
September 2013  

Received 8 August 2013
Accepted 16 August 2013
Online 23 August 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.006 Å
R = 0.053
wR = 0.137
Data-to-parameter ratio = 15.6
Details
Open access

2-(4-Bromobenzoyl)-1-ferrocenylspiro[11H-pyrrolidizine-3,11'-indeno[1,2-b]quinoxaline]

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

In the title compound, [Fe(C5H5)(C33H25BrN3O)], the fused four-ring system, 11H-indeno[1,2-b]quinoxaline is essentially planar, with a maximum deviation of 0.087 (3) Å from the least-squares plane of the attached benzene ring. The pyrrolidine rings adopt envelope conformation and make a dihedral angle of 51.76 (19)° with each other. The cyclopentadiene rings of the ferrocenyl moiety have an eclipsed conformation. The Br atom deviates by 0.0190 (9) Å from the attached benzene ring. The molecular structure features an intramolecular C-H...N interaction, which generates an S(8) ring motif. The crystal packing features C-H...O interactions, which generate R22(18) centrosymmetric dimers, as well as C-H...[pi] interactions.

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 a related structure, see: Vijayakumar et al. (2012[Vijayakumar, B., Gavaskar, D., Srinivasan, T., Raghunathan, R. & Velmurugan, D. (2012). Acta Cryst. E68, m1382-m1383.]). For graph-set notation, 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
  • [Fe(C5H5)(C33H25BrN3O)]

  • Mr = 680.41

  • Triclinic, [P \overline 1]

  • a = 9.3668 (3) Å

  • b = 9.9785 (3) Å

  • c = 18.6303 (5) Å

  • [alpha] = 89.724 (1)°

  • [beta] = 75.967 (1)°

  • [gamma] = 63.236 (1)°

  • V = 1497.37 (8) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 1.88 mm-1

  • T = 293 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.603, Tmax = 0.706

  • 22634 measured reflections

  • 6177 independent reflections

  • 5078 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.053

  • wR(F2) = 0.137

  • S = 1.04

  • 6177 reflections

  • 397 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 1.87 e Å-3

  • [Delta][rho]min = -1.63 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C29-C33, C9-C15 and N1/N2/C1/C6/C7/C11 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C28-H28...N2 0.93 2.56 3.358 (5) 145
C13-H13...O1i 0.93 2.58 3.318 (4) 137
C4-H4...Cg1ii 0.93 2.69 3.580 (4) 159
C17-H17B...Cg2iii 0.97 2.84 3.743 (4) 155
C36-H36...Cg3iv 0.98 2.70 3.486 (5) 137
Symmetry codes: (i) -x+1, -y, -z+2; (ii) -x+1, -y+1, -z+1; (iii) -x+1, -y+1, -z+2; (iv) x-1, y, z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. 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 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); 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: PV2643 ).


Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. SS, KG and DV thank the UGC (SAP-CAS) for the departmental facilties. SS also thanks the UGC for a meritorious fellowship.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Biot, C., Dessolin, J., Richard, I. & Dive, D. (2004). J. Organomet. Chem. 689, 4678-4682.  [CrossRef] [ChemPort]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [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]
Jaouen, G., Top, S., Vessireres, A., Leclercq, G., Vaissermann, J. & McGlinchey, M. J. (2004). Curr. Med. Chem. 11, 2505-2517.  [ISI] [CrossRef] [PubMed] [ChemPort]
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]
Vijayakumar, B., Gavaskar, D., Srinivasan, T., Raghunathan, R. & Velmurugan, D. (2012). Acta Cryst. E68, m1382-m1383.  [CSD] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, m512-m513   [ doi:10.1107/S1600536813023064 ]

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