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Volume 69 
Part 8 
Pages m433-m434  
August 2013  

Received 25 June 2013
Accepted 30 June 2013
Online 6 July 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.004 Å
R = 0.041
wR = 0.083
Data-to-parameter ratio = 19.1
Details
Open access

{2-[2,2-Bis(4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl-[kappa]N)propyl]pyridine}dichloridoiron(II)

aDipartimento di Ingegneria, Università di Napoli 'Parthenope', Centro Direzionale di Napoli, Isola C4, 80143 Napoli, Italy,bDipartimento di Scienze Chimiche, Università degli Studi di Napoli 'Federico II', Complesso di Monte S. Angelo, Via Cinthia, 80126 Napoli, Italy, and cDipartimento di Chimica e Biologia, Università degli Studi di Salerno, Via Giovanni Paolo II 132, 84084 Fisciano (Salerno), Italy
Correspondence e-mail: giuseppina.roviello@uniparthenope.it

The title compound,[FeCl2(C18H25N3O2)], has a distorted tetrahedral Cl2N2 coordination of the FeII atom as a result of the constraints imposed by the 2-[2,2-bis(4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl)propyl]pyridine ligand. The pyridine ring is almost perpendicular to the six-membered chelated ring containing the metal atom [dihedral angle between their mean planes = 88.5 (1)°].

Related literature

For the analogous bis(oxazoline)iron(II) complex, see: Ferro et al. (2007[Ferro, R., Milione, S., Bertolasi, V., Capacchione, C. & Grassi, A. (2007). Macromolecules, 40, 8544-8546.]). For active catalysts used in atom-transfer radical polymerization (ATRP) reactions, see: Matyjaszewski & Xia (2001[Matyjaszewski, K. & Xia, J. (2001). Chem. Rev. 101, 2921-2990.]); Kamigaito et al. (2001[Kamigaito, M., Ando, T. & Sawamoto, M. (2001). Chem. Rev. 101, 3689-3745.]); De Roma et al. (2011[De Roma, A., Yang, H.-J., Milione, S., Capacchione, C., Roviello, G. & Grassi, A. (2011). Inorg. Chem. Commun. 14, 542-544.]); Ferro et al. (2009[Ferro, R., Milione, S., Caruso, T. & Grassi, A. (2009). J. Mol. Catal. A: Chemical 307, 128-133.]). For similar salicylaldiminato complexes, see: O`Reilly et al. (2003[O`Reilly, R. K., Gibson, V. C., White, A. J. P. & Williams, D. J. (2003). J. Am. Chem. Soc. 125, 8450-8451.]). For structural data on metal complexes, see: Li, Lamberti, Mazzeo et al. (2012[Li, G., Lamberti, M., Mazzeo, M., Pappalardo, D., Roviello, G. & Pellecchia, C. (2012). Organometallics 31, 1180-1188.]); Li, Lamberti, Roviello et al. (2012[Li, G., Lamberti, M., Roviello, G. & Pellecchia, C. (2012). Organometallics 31, 6772-6778.]); Busico et al. (2006[Busico, V., Cipullo, R., Pellecchia, R., Ronca, S., Roviello, G. & Talarico, G. (2006). Proc. Natl. Acad. Sci. USA. 103, 15321-15326.]); D`Auria et al. (2012[D`Auria, I., Lamberti, M., Mazzeo, M., Milione, S., Roviello, G. & Pellecchia, C. (2012). Chem. Eur. J. 18, 2349-2360.]). For N-rich aromatic heterocycles, see: Carella et al. (2012[Carella, A., Borbone, F., Roviello, A., Roviello, G., Tuzi, A., Kravinsky, A., Shikler, R., Cantele, G. & Ninno, G. (2012). Dyes Pigments, 95, 116-125.]), Roviello et al. (2012[Roviello, G. N., Roviello, G., Musumeci, D., Bucci, E. M. & Pedone, C. (2012). Amino Acids 43, 1615-1623.]); Milione & Bertolasi (2011[Milione, S. & Bertolasi, V. (2011). Tetrahedron Lett. 52, 3570-3574.]).

[Scheme 1]

Experimental

Crystal data
  • [FeCl2(C18H25N3O2)]

  • Mr = 442.16

  • Monoclinic, P 21 /c

  • a = 10.102 (2) Å

  • b = 13.925 (3) Å

  • c = 14.764 (2) Å

  • [beta] = 105.27 (1)°

  • V = 2003.5 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 1.04 mm-1

  • T = 173 K

  • 0.20 × 0.10 × 0.10 mm

Data collection
  • Bruker-Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.820, Tmax = 0.903

  • 16483 measured reflections

  • 4578 independent reflections

  • 3033 reflections with I > 2[sigma](I)

  • Rint = 0.054

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.083

  • S = 1.01

  • 4578 reflections

  • 240 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Data collection: COLLECT (Nonius, 1999[Nonius (1999). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000[Duisenberg, A. J. M., Hooft, R. W. W., Schreurs, A. M. M. & Kroon, J. (2000). J. Appl. Cryst. 33, 893-898.]); data reduction: EVALCCD (Duisenberg et al., 2003[Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229.]); 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: 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: GG2121 ).


Acknowledgements

The authors thank the Centro Interdipartimentale di Metodologie Chimico-Fisiche, Università degli Studi di Napoli "Federico II" for X-ray facilities.

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.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Busico, V., Cipullo, R., Pellecchia, R., Ronca, S., Roviello, G. & Talarico, G. (2006). Proc. Natl. Acad. Sci. USA. 103, 15321-15326.  [CSD] [CrossRef] [PubMed] [ChemPort]
Carella, A., Borbone, F., Roviello, A., Roviello, G., Tuzi, A., Kravinsky, A., Shikler, R., Cantele, G. & Ninno, G. (2012). Dyes Pigments, 95, 116-125.  [CSD] [CrossRef] [ChemPort]
D`Auria, I., Lamberti, M., Mazzeo, M., Milione, S., Roviello, G. & Pellecchia, C. (2012). Chem. Eur. J. 18, 2349-2360.
De Roma, A., Yang, H.-J., Milione, S., Capacchione, C., Roviello, G. & Grassi, A. (2011). Inorg. Chem. Commun. 14, 542-544.  [Web of Science] [CrossRef] [ChemPort]
Duisenberg, A. J. M., Hooft, R. W. W., Schreurs, A. M. M. & Kroon, J. (2000). J. Appl. Cryst. 33, 893-898.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Ferro, R., Milione, S., Bertolasi, V., Capacchione, C. & Grassi, A. (2007). Macromolecules, 40, 8544-8546.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Ferro, R., Milione, S., Caruso, T. & Grassi, A. (2009). J. Mol. Catal. A: Chemical 307, 128-133.
Kamigaito, M., Ando, T. & Sawamoto, M. (2001). Chem. Rev. 101, 3689-3745.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Li, G., Lamberti, M., Mazzeo, M., Pappalardo, D., Roviello, G. & Pellecchia, C. (2012). Organometallics 31, 1180-1188.  [CSD] [CrossRef] [ChemPort]
Li, G., Lamberti, M., Roviello, G. & Pellecchia, C. (2012). Organometallics 31, 6772-6778.  [CrossRef] [ChemPort]
Matyjaszewski, K. & Xia, J. (2001). Chem. Rev. 101, 2921-2990.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Milione, S. & Bertolasi, V. (2011). Tetrahedron Lett. 52, 3570-3574.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Nonius (1999). COLLECT. Nonius BV, Delft, The Netherlands.
O`Reilly, R. K., Gibson, V. C., White, A. J. P. & Williams, D. J. (2003). J. Am. Chem. Soc. 125, 8450-8451.
Roviello, G. N., Roviello, G., Musumeci, D., Bucci, E. M. & Pedone, C. (2012). Amino Acids 43, 1615-1623.  [Web of Science] [CSD] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, m433-m434   [ doi:10.1107/S1600536813018047 ]

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