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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 [sigma](C-C) = 0.004 Å
R = 0.025
wR = 0.062
Data-to-parameter ratio = 19.0
Details
Open access

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

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[Bai, Y., Zhang, G. Q., Dang, D. B., Qi, Z. Y. & Zhang, L. (2011). Z. Naturforsch. Teil B, 66, 549-552.]); Ballester et al. (2003[Ballester, L., Gil, A. M., Gutierrez, A., Perpinan, M. F., Sanchez, A. E., Fonari, M., Suwinska, K. & Belsky, V. (2003). Eur. J. Inorg. Chem. pp. 3034-3041.]); Blake et al. (2004[Blake, A. J., Caltagirone, C., Lippolis, V., Schröder, M. & Wilson, C. (2004). Acta Cryst. E60, m20-m21.]); Broomsgrove et al. (2010[Broomsgrove, A. E. J., Addy, D. A., Di Paolo, A., Morgan, I. R., Bresner, C., Chislett, V., Fallis, I. A., Thompson, A. L., Vidovic, D. & Aldridge, S. (2010). Inorg. Chem. 49, 157-173.]); Chohan et al. (1997[Chohan, Z. H., Howie, R. A., Wardell, J. L., Wilkens, R. & Doidge-Harrison, S. M. S. V. (1997). Polyhedron, 16, 2689-2696.]); Deck et al. (2000[Deck, P. A., Lane, M. J., Montgomery, J. L., Slebodnick, C. & Fronczek, F. R. (2000). Organometallics, 19, 1013-1024.]); Ferguson et al. (1994[Ferguson, G., Gallagher, J. F., Glidewell, C. & Zakaria, C. M. (1994). Acta Cryst. B50, 146-150.]); Herbstein & Kapon (2008[Herbstein, F. H. & Kapon, M. (2008). Struct. Chem. 19, 679-682.]); Hong et al. (2005[Hong, J., Tang, L.-F., Yang, Z., Zhai, Y.-P. & Nan, M. (2005). Transition Met. Chem. 30, 439-444.]); Hosmane et al. (1998[Hosmane, N. S., Franken, A., Zhang, G., Srivastava, R. R., Smith, R. Y. & Spielvogel, B. F. (1998). Main Group Met. Chem. 21, 319-324.]); Hu et al. (2004[Hu, J., Barbour, L. J. & Gokel, G. W. (2004). New J. Chem. 28, 907-911.]); Li et al. (2009[Li, Z., Liu, B., Xu, H., Xue, G., Hu, H., Fu, F. & Wang, J. (2009). J. Organomet. Chem. 694, 2210-2216.]); Malezieux et al. (1994[Malezieux, B., Gruselle, M., Troitskaya, L. L., Sokolov, V. I. & Vaissermann, J. (1994). Organometallics, 13, 2979-2986.]); Pullen et al. (1998[Pullen, A. E., Faulmann, C., Pokhodnya, K. I., Cassoux, P. & Tokumoto, M. (1998). Inorg. Chem. 37, 6714-6720.]); Reynes et al. (2002[Reynes, O., Moutet, J.-C., Pecaut, J., Royal, G. & Saint-Aman, E. (2002). New J. Chem. 26, 9-12.]); Selvapalam et al. (2007[Selvapalam, N., Kim, H., Sobransingh, D., Kaifer, A. E., Liu, S., Isaacs, L., Chen, W., Moghaddam, S., Gilson, M. K., Kim, K. & Inoue, Y. (2007). Proc. Natl Acad. Sci. USA, 104, 20737-20742.]); Sharma et al. (2006[Sharma, P., Lopez, J. G., Ortega, C., Rosas, N., Cabrera, A., Alvarez, C., Toscano, A. & Reyes, E. (2006). Inorg. Chem. Commun. 9, 82-85.]); Veya & Kochi (1995[Veya, P. L. & Kochi, J. K. (1995). J. Organomet. Chem. 488, C4-C8.]); Volkov et al. (2003[Volkov, O., Rath, N. P. & Barton, L. (2003). J. Organomet. Chem. 680, 212-217.], 2005[Volkov, O., Hu, C., Kolle, V. & Paetzold, P. (2005). Z. Anorg. Allg. Chem. 631, 1909-1911.], 2006[Volkov, O., Paetzold, P. & Hu, C. (2006). Z. Anorg. Allg. Chem. 632, 945-948.]); Xu et al. (2010[Xu, H., Zhang, L., Li, Z., Li, Z., Hu, H. & Xue, G. (2010). J. Cluster Sci. 21, 211-221.]); Yongmao et al. (1982[Yongmao, Z., Zhaoping, C., Zhiwei, C., Kezhen, P., Jiaxi, L., Guomin, Z. & Hong, Z. (1982). Jiegou Huaxue, 1, 45-46.]); Zhuji et al. (1982[Zhuji, F., Kezhen, P., Jiaxi, L., Guomin, Z. & Hong, Z. (1982). Jiegou Huaxue, 1, 57-59.]). For their use in chemistry, see: Routaboul et al. (2005[Routaboul, L., Vincendeau, S., Daran, J.-C. & Manoury, E. (2005). Tetrahedron Asymmetry, 16, 2685-2690.], 2007[Routaboul, L., Vincendeau, S., Turrin, C.-O., Caminade, A.-M., Majoral, J.-P., Daran, J.-C. & Manoury, E. (2007). J. Organomet. Chem. 692, 1064-1073.]); Mateus et al. (2006[Mateus, N., Routaboul, L., Daran, J.-C. & Manoury, E. (2006). J. Organomet. Chem. 691, 2297-2310.]); Le Roux et al. (2007[Le Roux, E., Malacea, R., Manoury, E., Poli, R., Gonsalvi, L. & Peruzzini, M. (2007). Adv. Synth. Catal. 349, 1064-1073.]); Diab et al. (2008[Diab, L., Gouygou, M., Manoury, E., Kalck, P. & Urrutigoïty, M. (2008). Tetrahedron Lett. 49, 5186-5189.]); Audin et al. (2010[Audin, C., Daran, J.-C., Deydier, E., Manoury, E. & Poli, R. (2010). C. R. Chim. 13, 890-899.]); Debono et al. (2010[Debono, N., Labande, A., Manoury, E., Daran, J.-C. & Poli, R. (2010). Organometallics, 29, 1879-1882.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • [Fe(C5H5)(C21H24NPS)]I·CHCl3

  • Mr = 720.65

  • Monoclinic, P 21 /c

  • a = 17.4056 (6) Å

  • b = 12.1843 (3) Å

  • c = 14.9389 (5) Å

  • [beta] = 110.632 (4)°

  • V = 2964.97 (18) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.574, Tmax = 1.0

  • 31103 measured reflections

  • 6065 independent reflections

  • 5385 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.025

  • wR(F2) = 0.062

  • S = 1.08

  • 6065 reflections

  • 319 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.62 e Å-3

  • [Delta][rho]min = -0.61 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C24-H24C...I1 0.98 3.05 4.001 (3) 163
C100-H100...I1 1.00 2.93 3.810 (3) 147

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR97 (Altomare et al., 1999[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.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.]) and ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


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.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
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.  [ISI] [CrossRef] [ChemPort] [details]
Audin, C., Daran, J.-C., Deydier, E., Manoury, E. & Poli, R. (2010). C. R. Chim. 13, 890-899.  [CrossRef] [ChemPort]
Bai, Y., Zhang, G. Q., Dang, D. B., Qi, Z. Y. & Zhang, L. (2011). Z. Naturforsch. Teil B, 66, 549-552.  [CrossRef] [ChemPort]
Ballester, L., Gil, A. M., Gutierrez, A., Perpinan, M. F., Sanchez, A. E., Fonari, M., Suwinska, K. & Belsky, V. (2003). Eur. J. Inorg. Chem. pp. 3034-3041.  [ISI] [CSD] [CrossRef]
Blake, A. J., Caltagirone, C., Lippolis, V., Schröder, M. & Wilson, C. (2004). Acta Cryst. E60, m20-m21.  [CSD] [CrossRef] [details]
Broomsgrove, A. E. J., Addy, D. A., Di Paolo, A., Morgan, I. R., Bresner, C., Chislett, V., Fallis, I. A., Thompson, A. L., Vidovic, D. & Aldridge, S. (2010). Inorg. Chem. 49, 157-173.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
Chohan, Z. H., Howie, R. A., Wardell, J. L., Wilkens, R. & Doidge-Harrison, S. M. S. V. (1997). Polyhedron, 16, 2689-2696.  [CrossRef] [ChemPort] [ISI]
Debono, N., Labande, A., Manoury, E., Daran, J.-C. & Poli, R. (2010). Organometallics, 29, 1879-1882.  [CSD] [CrossRef] [ChemPort]
Deck, P. A., Lane, M. J., Montgomery, J. L., Slebodnick, C. & Fronczek, F. R. (2000). Organometallics, 19, 1013-1024.  [CrossRef] [ChemPort]
Diab, L., Gouygou, M., Manoury, E., Kalck, P. & Urrutigoïty, M. (2008). Tetrahedron Lett. 49, 5186-5189.  [ISI] [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Ferguson, G., Gallagher, J. F., Glidewell, C. & Zakaria, C. M. (1994). Acta Cryst. B50, 146-150.  [CrossRef] [ISI] [details]
Herbstein, F. H. & Kapon, M. (2008). Struct. Chem. 19, 679-682.  [ISI] [CSD] [CrossRef] [ChemPort]
Hong, J., Tang, L.-F., Yang, Z., Zhai, Y.-P. & Nan, M. (2005). Transition Met. Chem. 30, 439-444.  [ISI] [CSD] [CrossRef] [ChemPort]
Hosmane, N. S., Franken, A., Zhang, G., Srivastava, R. R., Smith, R. Y. & Spielvogel, B. F. (1998). Main Group Met. Chem. 21, 319-324.  [CrossRef] [ChemPort]
Hu, J., Barbour, L. J. & Gokel, G. W. (2004). New J. Chem. 28, 907-911.  [ISI] [CSD] [CrossRef] [ChemPort]
Le Roux, E., Malacea, R., Manoury, E., Poli, R., Gonsalvi, L. & Peruzzini, M. (2007). Adv. Synth. Catal. 349, 1064-1073.
Li, Z., Liu, B., Xu, H., Xue, G., Hu, H., Fu, F. & Wang, J. (2009). J. Organomet. Chem. 694, 2210-2216.  [CSD] [CrossRef] [ChemPort]
Malezieux, B., Gruselle, M., Troitskaya, L. L., Sokolov, V. I. & Vaissermann, J. (1994). Organometallics, 13, 2979-2986.  [CrossRef] [ChemPort]
Mateus, N., Routaboul, L., Daran, J.-C. & Manoury, E. (2006). J. Organomet. Chem. 691, 2297-2310.  [CSD] [CrossRef] [ChemPort]
Pullen, A. E., Faulmann, C., Pokhodnya, K. I., Cassoux, P. & Tokumoto, M. (1998). Inorg. Chem. 37, 6714-6720.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Reynes, O., Moutet, J.-C., Pecaut, J., Royal, G. & Saint-Aman, E. (2002). New J. Chem. 26, 9-12.  [ISI] [CSD] [CrossRef] [ChemPort]
Routaboul, L., Vincendeau, S., Daran, J.-C. & Manoury, E. (2005). Tetrahedron Asymmetry, 16, 2685-2690.  [ISI] [CrossRef] [ChemPort]
Routaboul, L., Vincendeau, S., Turrin, C.-O., Caminade, A.-M., Majoral, J.-P., Daran, J.-C. & Manoury, E. (2007). J. Organomet. Chem. 692, 1064-1073.  [CSD] [CrossRef] [ChemPort]
Selvapalam, N., Kim, H., Sobransingh, D., Kaifer, A. E., Liu, S., Isaacs, L., Chen, W., Moghaddam, S., Gilson, M. K., Kim, K. & Inoue, Y. (2007). Proc. Natl Acad. Sci. USA, 104, 20737-20742.  [PubMed]
Sharma, P., Lopez, J. G., Ortega, C., Rosas, N., Cabrera, A., Alvarez, C., Toscano, A. & Reyes, E. (2006). Inorg. Chem. Commun. 9, 82-85.  [ISI] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Veya, P. L. & Kochi, J. K. (1995). J. Organomet. Chem. 488, C4-C8.  [CrossRef] [ChemPort]
Volkov, O., Hu, C., Kolle, V. & Paetzold, P. (2005). Z. Anorg. Allg. Chem. 631, 1909-1911.  [CSD] [CrossRef] [ChemPort]
Volkov, O., Paetzold, P. & Hu, C. (2006). Z. Anorg. Allg. Chem. 632, 945-948.  [CSD] [CrossRef] [ChemPort]
Volkov, O., Rath, N. P. & Barton, L. (2003). J. Organomet. Chem. 680, 212-217.  [CSD] [CrossRef] [ChemPort]
Xu, H., Zhang, L., Li, Z., Li, Z., Hu, H. & Xue, G. (2010). J. Cluster Sci. 21, 211-221.  [ISI] [CSD] [CrossRef] [ChemPort]
Yongmao, Z., Zhaoping, C., Zhiwei, C., Kezhen, P., Jiaxi, L., Guomin, Z. & Hong, Z. (1982). Jiegou Huaxue, 1, 45-46.
Zhuji, F., Kezhen, P., Jiaxi, L., Guomin, Z. & Hong, Z. (1982). Jiegou Huaxue, 1, 57-59.


Acta Cryst (2012). E68, m1490-m1491   [ doi:10.1107/S1600536812046053 ]

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