rac-{[2-(Diphenyl­thio­phosphan­yl)ferrocen­yl]meth­yl}trimethyl­ammonium iodide chloro­form monosolvate

Karpous, A.; Voitenko, Z.; Daran, J.-C.; Manoury, E.

doi:10.1107/S1600536812046053

Volume 68
Part 12
Pages m1490-m1491
December 2012

Received 12 October 2012
Accepted 7 November 2012
Online 17 November 2012

Key indicators
Single-crystal X-ray study
T = 180 K
Mean (C-C) = 0.004 Å
R = 0.025
wR = 0.062
Data-to-parameter ratio = 19.0
Details

rac-{[2-(Diphenylthiophosphanyl)ferrocenyl]methyl}trimethylammonium iodide chloroform monosolvate

Andrei Karpous,^a Zoia Voitenko,^b Jean-Claude Daran ^a ^* and Eric Manoury ^a

^aCNRS, LCC, 205 route de Narbonne, BP 44099, F-31077, Toulouse Cedex 4, France, and ^bUniversity Taras Shevchenko, Vladimirska st 64, 01033 Kiev, Ukraine
Correspondence e-mail: daran@lcc-toulouse.fr

The title compound, [Fe(C₅H₅)(C₂₁H₂₄NPS)]I·CHCl₃, is built up from a (ferrocenylmethyl)trimethylammonium cation, a iodine anion and a chloroform solvent molecule, all residing in general positions. The N atom of the ammonium group is displaced by 1.182 (2) Å from the plane of the substituted cyclopentadienyl (Cp) ring towards the Fe atom, whereas the C atom attached to the same Cp ring is slightly below this plane by -0.128 (2) Å. These deviations might result from weak agostic interactions between the two H atoms of the CH₂ group and the Fe atom.

Related literature

For related structures containing the (ferrocenyl)trimethylammonium framework, see: Bai et al. (2011); Ballester et al. (2003); Blake et al. (2004); Broomsgrove et al. (2010); Chohan et al. (1997); Deck et al. (2000); Ferguson et al. (1994); Herbstein & Kapon (2008); Hong et al. (2005); Hosmane et al. (1998); Hu et al. (2004); Li et al. (2009); Malezieux et al. (1994); Pullen et al. (1998); Reynes et al. (2002); Selvapalam et al. (2007); Sharma et al. (2006); Veya & Kochi (1995); Volkov et al. (2003, 2005, 2006); Xu et al. (2010); Yongmao et al. (1982); Zhuji et al. (1982). For their use in chemistry, see: Routaboul et al. (2005, 2007); Mateus et al. (2006); Le Roux et al. (2007); Diab et al. (2008); Audin et al. (2010); Debono et al. (2010). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental

Crystal data

[Fe(C₅H₅)(C₂₁H₂₄NPS)]I·CHCl₃
M_r = 720.65
Monoclinic, P 2₁ /c
a = 17.4056 (6) Å
b = 12.1843 (3) Å
c = 14.9389 (5) Å
= 110.632 (4)°
V = 2964.97 (18) Å³
Z = 4
Mo K radiation
= 1.96 mm^-1
T = 180 K
0.49 × 0.18 × 0.10 mm

Data collection

Agilent Xcalibur (Sapphire1, long nozzle) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) T_min = 0.574, T_max = 1.0
31103 measured reflections
6065 independent reflections
5385 reflections with I > 2(I)
R_int = 0.034

Refinement

R[F² > 2(F²)] = 0.025
wR(F²) = 0.062
S = 1.08
6065 reflections
319 parameters
H-atom parameters constrained
_max = 0.62 e Å^-3
_min = -0.61 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C24-H24CI1	0.98	3.05	4.001 (3)	163
C100-H100I1	1.00	2.93	3.810 (3)	147

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RN2109 ).

Acknowledgements

AK thanks the Ministry of Education, Science, Youth and Sports of Ukraine for funding his stay at the LCC.

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