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Volume 69 
Part 12 
Page o1824  
December 2013  

Received 4 November 2013
Accepted 19 November 2013
Online 27 November 2013

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.002 Å
R = 0.030
wR = 0.075
Data-to-parameter ratio = 13.4
Details
Open access

Diethyl [4-(2,2':6',2''-terpyridine-4'-yl)phen­yl]phospho­nate

aDepartment of Chemistry, Faculty of Science, Masaryk University, Kotlarska 2, CZ-61137 Brno, Czech Republic, and bCentral European Institute of Technology (CEITEC), Masaryk University, 625 00 Brno, Czech Republic
Correspondence e-mail: jpinkas@chemi.muni.cz

The title compound, C25H24N3O3P, was obtained by catalytic phospho­nation of 4'-(4-bromphen­yl)-2,2':6',2''-terpyridine. The terpyridine moiety is nearly planar, the dihedral angles between the central and the outer rings being 4.06 (9) and 5.39 (9)°. The N atoms in the two pyridine rings are oriented nearly anti­periplanar to that of the central ring. The benzene ring is rotated out of the plane of the central ring of the terpyridine unit by 34.65 (6)°.

Related literature

Terpyridines (Heller & Schubert, 2003[Heller, M. & Schubert, U. S. (2003). Eur. J. Org. Chem. pp. 947-961.]) are frequently employed as tridentate chelating ligands for transition and rare earth metals forming very stable square planar mono- (Eryazici et al., 2008[Eryazici, I., Moorefield, C. N. & Newkome, G. R. (2008). Chem. Rev. 108, 1834-1895.]) or octa­hedral bis-complexes (Constable, 2007[Constable, E. C. (2007). Chem. Soc. Rev. 36, 246-253.], 2008[Constable, E. C. (2008). Coord. Chem. Rev. 252, 842-855.]). For related symmetrical 4'-substituted terpyridine derivatives, see: Hofmeier & Schubert (2004[Hofmeier, H. & Schubert, U. S. (2004). Chem. Soc. Rev. 33, 373-399.]); Andres & Schubert (2004[Andres, R. P. & Schubert, U. S. (2004). Adv. Mater. 16, 1043-1068.]).

[Scheme 1]

Experimental

Crystal data
  • C25H24N3O3P

  • Mr = 445.44

  • Monoclinic, P 21 /c

  • a = 12.5290 (4) Å

  • b = 13.0264 (4) Å

  • c = 14.5681 (5) Å

  • [beta] = 111.674 (3)°

  • V = 2209.53 (12) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.16 mm-1

  • T = 120 K

  • 0.40 × 0.40 × 0.30 mm

Data collection
  • Oxford Diffraction Xcalibur (Sapphire2) diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis RED and CrysAlis CCD. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.957, Tmax = 1.000

  • 23115 measured reflections

  • 3886 independent reflections

  • 2809 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.030

  • wR(F2) = 0.075

  • S = 1.02

  • 3886 reflections

  • 291 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.36 e Å-3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis RED and CrysAlis CCD. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis RED and CrysAlis CCD. Oxford Diffraction Ltd, Yarnton, England.]); data reduction: CrysAlis RED; 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: NC2320 ).


Acknowledgements

This work was supported by CEITEC-Central European Institute of Technology (CZ.1.05/1.1.00/02.0068) and GACR P207/11/0555.

References

Andres, R. P. & Schubert, U. S. (2004). Adv. Mater. 16, 1043-1068.  [Web of Science] [CrossRef] [ChemPort]
Constable, E. C. (2007). Chem. Soc. Rev. 36, 246-253.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Constable, E. C. (2008). Coord. Chem. Rev. 252, 842-855.  [Web of Science] [CrossRef] [ChemPort]
Eryazici, I., Moorefield, C. N. & Newkome, G. R. (2008). Chem. Rev. 108, 1834-1895.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Heller, M. & Schubert, U. S. (2003). Eur. J. Org. Chem. pp. 947-961.  [CrossRef]
Hofmeier, H. & Schubert, U. S. (2004). Chem. Soc. Rev. 33, 373-399.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Oxford Diffraction (2009). CrysAlis RED and CrysAlis CCD. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1824  [ doi:10.1107/S1600536813031541 ]

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