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Volume 70 
Part 1 
Page m13  
January 2014  

Received 2 December 2013
Accepted 4 December 2013
Online 11 December 2013

Key indicators
Single-crystal X-ray study
T = 166 K
Mean [sigma](C-C) = 0.010 Å
R = 0.035
wR = 0.091
Data-to-parameter ratio = 24.4
Details
Open access

1-(Bromo­mercurio)ferrocene

aInstitut für Anorganische und Analytische Chemie, Universität Frankfurt, Max-von-Laue-Strasse 7, D-60438 Frankfurt am Main, Germany, and bInstitut für Organische Chemie und Chemische Biologie, Universität Frankfurt, Max-von-Laue-Strasse 7, D-60438 Frankfurt am Main, Germany
Correspondence e-mail: bats@chemie.uni-frankfurt.de

The asymmetric unit of the title compound, [Fe(C5H5)(C5H4BrHg)], contains two independent mol­ecules, A and B, in which the Hg-C bond lengths are 2.045 (6) and 2.046 (6) Å, the Hg-Br bond lengths are 2.4511 (9) and 2.4562 (7) Å, and the C-Hg-Br angles are 176.42 (17) and 177.32 (17)°. The two cyclo­penta­dienyl rings of mol­ecule A are eclipsed, while those of mol­ecule B are almost staggered. The HgBr groups are connected by inter­molecular Hg...Br contacts of 3.3142 (9)-3.4895 (11) Å, forming layers parallel to (001). These layers contain both four-membered (HgBr)2 and eight-membered (HgBr)4 rings. Ferrocene-ferrocene C-H...[pi] contacts connect the mol­ecular layers along the c-axis direction.

Related literature

For synthetic background, see: Fish & Rosenblum (1965[Fish, R. W. & Rosenblum, M. (1965). J. Org. Chem. 30, 1253-1254.]); Guillaneux & Kagan (1995[Guillaneux, D. & Kagan, H. B. (1995). J. Org. Chem. 60, 2502-2505.]). For chemical background, see: Lerner (2005[Lerner, H.-W. (2005). Coord. Chem. Rev. 249, 781-798.]). For related structures, see: Meyer-Wegner et al. (2012[Meyer-Wegner, F., Lerner, H.-W., Sinke, T. & Bolte, M. (2012). Acta Cryst. E68, m424.]); Hayashi et al. (2011[Hayashi, M., Bolte, M., Wagner, M. & Lerner, H.-W. (2011). Z. Anorg. Allg. Chem. 637, 646-649.]); Franz et al. (2011[Franz, D., Lerner, H.-W. & Bolte, M. (2011). Acta Cryst. E67, m1395.]); Wiberg et al. (1997[Wiberg, N., Amelunxen, K., Lerner, H.-W., Nöth, H., Appel, A., Knizek, J. & Polborn, K. (1997). Z. Anorg. Allg. Chem. 623, 1861-1870.], 2001[Wiberg, N., Niedermayer, W., Lerner, H.-W. & Bolte, M. (2001). Z. Anorg. Allg. Chem. 627, 1043-1047.]); Margraf et al. (2004[Margraf, G., Lerner, H.-W., Bolte, M. & Wagner, M. (2004). Z. Anorg. Allg. Chem. 630, 217-218.]); Sünkel & Kiessling (2001[Sünkel, K. & Kiessling, T. (2001). J. Organomet. Chem. 637, 796-799.]); Romanov et al. (2007[Romanov, A. S., Yakovenko, A. A., Antipin, M. Yu., Lindline, J. & Timofeeva, T. V. (2007). Acta Cryst. E63, m1297-m1299.]); Singh et al. (2005[Singh, G., Bali, S., Singh, A. K., Drake, J. E., Macdonald, C. L. B., Hursthouse, M. B. & Little, M. E. (2005). Inorg. Chim. Acta, 358, 912-918.]). For van der Waals radii, see: Bondi (1964[Bondi, A. (1964). J. Phys. Chem. 68, 441-451.]).

[Scheme 1]

Experimental

Crystal data
  • [FeHgBr(C5H5)(C5H4)]

  • Mr = 465.52

  • Triclinic, [P \overline 1]

  • a = 7.6484 (14) Å

  • b = 9.5715 (17) Å

  • c = 14.394 (3) Å

  • [alpha] = 75.120 (12)°

  • [beta] = 87.548 (12)°

  • [gamma] = 83.298 (12)°

  • V = 1011.3 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 20.49 mm-1

  • T = 166 K

  • 0.65 × 0.28 × 0.05 mm

Data collection
  • Siemens SMART 1K CCD diffractometer

  • Absorption correction: numerical (SHELXTL; Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) Tmin = 0.010, Tmax = 0.361

  • 16880 measured reflections

  • 5759 independent reflections

  • 4942 reflections with I > 2[sigma](I)

  • Rint = 0.081

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.091

  • S = 1.10

  • 5759 reflections

  • 236 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 2.78 e Å-3

  • [Delta][rho]min = -1.93 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C6-C10 and C16-C20 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C3-H3A...Cg2iv 0.95 2.91 3.794 (8) 156
C19-H19A...Cg1iii 0.95 2.78 3.618 (8) 148
Symmetry codes: (iii) -x+1, -y+1, -z+1; (iv) x, y, z-1.

Data collection: SMART (Siemens, 1995[Siemens (1995). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SMART; data reduction: SAINT (Siemens, 1995[Siemens (1995). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2322 ).


References

Bondi, A. (1964). J. Phys. Chem. 68, 441-451.  [CrossRef] [ChemPort] [Web of Science]
Fish, R. W. & Rosenblum, M. (1965). J. Org. Chem. 30, 1253-1254.  [CrossRef] [ChemPort]
Franz, D., Lerner, H.-W. & Bolte, M. (2011). Acta Cryst. E67, m1395.  [CSD] [CrossRef] [IUCr Journals]
Guillaneux, D. & Kagan, H. B. (1995). J. Org. Chem. 60, 2502-2505.  [CrossRef] [ChemPort]
Hayashi, M., Bolte, M., Wagner, M. & Lerner, H.-W. (2011). Z. Anorg. Allg. Chem. 637, 646-649.  [CSD] [CrossRef] [ChemPort]
Lerner, H.-W. (2005). Coord. Chem. Rev. 249, 781-798.  [Web of Science] [CrossRef] [ChemPort]
Margraf, G., Lerner, H.-W., Bolte, M. & Wagner, M. (2004). Z. Anorg. Allg. Chem. 630, 217-218.  [CSD] [CrossRef] [ChemPort]
Meyer-Wegner, F., Lerner, H.-W., Sinke, T. & Bolte, M. (2012). Acta Cryst. E68, m424.  [CSD] [CrossRef] [IUCr Journals]
Romanov, A. S., Yakovenko, A. A., Antipin, M. Yu., Lindline, J. & Timofeeva, T. V. (2007). Acta Cryst. E63, m1297-m1299.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Siemens (1995). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Singh, G., Bali, S., Singh, A. K., Drake, J. E., Macdonald, C. L. B., Hursthouse, M. B. & Little, M. E. (2005). Inorg. Chim. Acta, 358, 912-918.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Sünkel, K. & Kiessling, T. (2001). J. Organomet. Chem. 637, 796-799.
Wiberg, N., Amelunxen, K., Lerner, H.-W., Nöth, H., Appel, A., Knizek, J. & Polborn, K. (1997). Z. Anorg. Allg. Chem. 623, 1861-1870.  [CSD] [CrossRef] [ChemPort]
Wiberg, N., Niedermayer, W., Lerner, H.-W. & Bolte, M. (2001). Z. Anorg. Allg. Chem. 627, 1043-1047.  [CSD] [CrossRef] [ChemPort]


Acta Cryst (2014). E70, m13  [ doi:10.1107/S1600536813032923 ]

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