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Volume 69 
Part 7 
Page m378  
July 2013  

Received 1 June 2013
Accepted 5 June 2013
Online 12 June 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.003 Å
R = 0.028
wR = 0.076
Data-to-parameter ratio = 17.8
Details
Open access

2-Ferrocenyl-3-nitro-2H-chromene

aPost Graduate and Research Department of Physics, Agurchand Manmull Jain College, Chennai 600 114, India, and bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: seshadri_pr@yahoo.com

In the title compound, [Fe(C5H5)(C14H10NO3)], the cyclopentadienyl rings are in an eclipsed conformation and the pyran ring adopts a half-chair conformation. The mean plane of the pyran ring makes dihedral angles of 79.33 (1) and 80.73 (1)°, respectively, with the substituted and unsubstituted cyclopentadienyl rings. In the crystal, pairs of C-H...O hydrogen bonds link the molecules into inversion dimers with R22(16) motifs.

Related literature

For the biological activity of ferrocenyl derivatives, see: 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.]); 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.]); Edwards et al. (1975[Edwards, E. I., Epton, R. & Marr, G. (1975). J. Organomet. Chem. 85, C23-C25.]). For conformational analysis and puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For related structures, see: Zora et al. (2006[Zora, M., Açikgöz, C., Tumay, T. A., Odabasoglu, M. & Büyükgüngör, O. (2006). Acta Cryst. C62, m327-m330.]); Paramasivam et al. (2013[Paramasivam, S., Purushothaman, S., Seshadri, P. R. & Raghunathan, R. (2013). Acta Cryst. E69, m144.]). 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)(C14H10NO3)]

  • Mr = 361.17

  • Monoclinic, P 21 /c

  • a = 10.047 (5) Å

  • b = 19.317 (5) Å

  • c = 8.135 (5) Å

  • [beta] = 96.667 (5)°

  • V = 1568.1 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.98 mm-1

  • T = 298 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 Ins., Madison, Wisconsin, USA.]) Tmin = 0.752, Tmax = 0.822

  • 14295 measured reflections

  • 3878 independent reflections

  • 3320 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.028

  • wR(F2) = 0.076

  • S = 1.01

  • 3878 reflections

  • 218 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C16-H16...O3i 0.93 2.55 3.390 (3) 150
Symmetry code: (i) -x+2, -y, -z+1.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Ins., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Ins., 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.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5279 ).


Acknowledgements

The authors acknowledge the Technology Business Incubator (TBI), CAS in Crystallography, University of Madras, Chennai, India, for the data collection.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
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 Ins., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Edwards, E. I., Epton, R. & Marr, G. (1975). J. Organomet. Chem. 85, C23-C25.  [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Fouda, M. F. R., Abd-Elzaher, M. M., Abdelsamaia, R. A. & Labib, A. A. (2007). Appl. Organomet. Chem. 21, 613-625.  [Web of Science] [CrossRef] [ChemPort]
Jaouen, G., Top, S., Vessireres, A., Leclercq, G., Vaissermann, J. & & McGlinchey, M. J. (2004). Curr. Med. Chem. 11, 2505-2517.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Paramasivam, S., Purushothaman, S., Seshadri, P. R. & Raghunathan, R. (2013). Acta Cryst. E69, m144.  [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Zora, M., Açikgöz, C., Tumay, T. A., Odabasoglu, M. & Büyükgüngör, O. (2006). Acta Cryst. C62, m327-m330.  [CSD] [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, m378  [ doi:10.1107/S1600536813015730 ]

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