N-(Ferrocenylmethyl)­dodecan-1-amine

Sun, L.-Z.; An, W.; Zhang, H.-C.; Xin, F.-F.; Hao, A.-Y.

doi:10.1107/S1600536810005155

Volume 66
Part 3
Page m301
March 2010

Received 23 January 2010
Accepted 9 February 2010
Online 13 February 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.037
wR = 0.112
Data-to-parameter ratio = 21.5
Details

N-(Ferrocenylmethyl)dodecan-1-amine

Li-Zhen Sun,^a Wei An,^a Hua-Cheng Zhang,^a Fei-Fei Xin ^a and Ai-You Hao ^a ^*

^aSchool of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China
Correspondence e-mail: haoay@sdu.edu.cn

The title compound, [Fe(C₅H₅)(C₁₈H₃₂N)], was synthesized by the amination of ferrocenecarbaldehyde. In the complex, the two cyclopentadienyl (Cp) rings are almost parallel with a dihedral angle of 1.36 (8)°, and are separated by a centroid-centroid distance of 3.299 (2) Å. In the crystal, adjacent molecules are linked into a one-dimensional supramolecular structure via weak C-H [pi] interactions between the Cp ring H atom and the Cp ring.

Related literature

For the applications of ferrocene in drug design, see: Atteke et al. (2003); Baramee et al. (2006). For linear ferrocene compounds in supramolecular chemisty, see: Zhang et al. (2010). For a related structure, see: Zheng & Liu (2009).

Experimental

Crystal data

[Fe(C₅H₅)(C₁₈H₃₂N)]
M_r = 383.39
Monoclinic, P 2₁ /c
a = 26.7005 (6) Å
b = 8.0549 (2) Å
c = 10.0069 (2) Å
= 97.534 (1)°
V = 2133.60 (8) Å³
Z = 4
Mo K radiation
= 0.71 mm^-1
T = 293 K
0.30 × 0.26 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.815, T_max = 0.881
20623 measured reflections
4900 independent reflections
3892 reflections with I > 2(I)
R_int = 0.021

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.112
S = 1.09
4900 reflections
228 parameters
H-atom parameters constrained
_max = 0.44 e Å^-3
_min = -0.37 e Å^-3

Table 1
Selected bond lengths (Å)

C14-Fe1	2.0502 (16)
C15-Fe1	2.0501 (18)
C16-Fe1	2.038 (2)
C17-Fe1	2.0295 (18)
C18-Fe1	2.0398 (18)
C19-Fe1	2.038 (2)
C20-Fe1	2.0350 (17)
C21-Fe1	2.0375 (18)
C22-Fe1	2.0398 (18)
C23-Fe1	2.0347 (19)

Table 2
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C19-C23 ring.

D-HA	D-H	HA	DA	D-HA
C18-H18Cg1ⁱ	0.98	2.96	3.870 (2)	155
Symmetry code: (i) $[x, -y+{\script{5\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2280 ).

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.
Atteke, C., Me Ndong, J. M., Aubouy, A., Maciejewski, L., Brocard, J., Lebibi, J. & Deloron, P. (2003). J. Antimicrob. Chemother. 51, 1021-1024.
Baramee, A., Coppin, A., Mortuaire, M., Pelinski, L., Tomavoc, S. & Brocard, J. (2006). Bioorg. Med. Chem. 14, 1294-1302.
Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2007). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Zhang, H., An, W., Liu, Z., Hao, A., Hao, J., Shen, J., Zhao, X., Sun, H. & Sun, L. (2010). Carbohydr. Res. 345, 87-96.
Zheng, X.-L. & Liu, J.-T. (2009). Acta Cryst. E65, m432.

metal-organic compounds