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Volume 69 
Part 9 
Page m500  
September 2013  

Received 1 August 2013
Accepted 12 August 2013
Online 17 August 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.034
wR = 0.094
Data-to-parameter ratio = 15.2
Details
Open access

6-Ferrocenoyl-7-phenylspiro[hexahydropyrrolo[1,2-c][1,3]thiazole-5,11'-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)(C32H24N3OS)], both the thiazolidine ring and the pyrrolidine ring adopt an envelope conformation, with the S atom and the phenyl-bearing C atom, respectively, as the flaps. The thiazolidine ring mean plane makes a dihedral angle of 59.08 (11)° with the pyrrolidine ring mean plane, which in turn makes a dihedral angle of 83.40 (10)° with the cyclopentane ring, indicating that the latter two rings are almost orthogonal to one another. In the crystal, a pair of C-H...O hydrogen bonds link the molecules forming inversion dimers. The dimers are linked via [pi]-[pi] interactions [centroid-centroid distance = 3.7764 (10) Å] involving the quinoxaline moieties forming chains propagating along [1-10].

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.]).

[Scheme 1]

Experimental

Crystal data
  • [Fe(C5H5)(C32H24N3OS)]

  • Mr = 619.55

  • Triclinic, [P \overline 1]

  • a = 9.5687 (3) Å

  • b = 10.0175 (3) Å

  • c = 17.1768 (5) Å

  • [alpha] = 80.367 (2)°

  • [beta] = 75.430 (1)°

  • [gamma] = 65.293 (1)°

  • V = 1444.02 (8) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.63 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 = 0.833, Tmax = 0.884

  • 21307 measured reflections

  • 5884 independent reflections

  • 5158 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.094

  • S = 1.02

  • 5884 reflections

  • 388 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.33 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C25-H25...O1i 0.93 2.58 3.371 (3) 143
Symmetry code: (i) -x, -y+1, -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: SU2630 ).


Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. SS and DV thank the UGC (SAP-CAS) for the departmental facilities. SS also thanks UGC 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, 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  [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, m500  [ doi:10.1107/S1600536813022605 ]

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