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Volume 70 
Part 1 
Page o73  
January 2014  

Received 11 December 2013
Accepted 13 December 2013
Online 18 December 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.123
Data-to-parameter ratio = 15.5
Details
Open access

2,6-Bis[1-(2,4,6-tri­methyl­phenyl­imino)­eth­yl]pyridine

aDepartment of Chemistry, University of Warwick, Gibbet Hill Road, Coventry CV4 7AL, England
Correspondence e-mail: a.b.chaplin@warwick.ac.uk

In the title mol­ecule, C27H31N3, the imine C=N groups are orientated anti to the pyridine N atom, with N-C-C-N torsion angles of -164.91 (11) and -170.53 (10)°. In the crystal, mol­ecules are connected by weak C-H...N and C-H...[pi] inter­actions parallel to the b axis.

Related literature

For representative examples of the organometallic and catalytic chemistry of dimino­pyridine complexes, see: Britovsek et al. (1999[Britovsek, G. J. P., Bruce, M., Gibson, V. C., Kimberley, B. S., Maddox, P. J., Mastroianni, S., McTavish, S. J., Redshaw, C., Solan, G. A., Strömberg, S., White, A. J. P. & Williams, D. J. (1999). J. Am. Chem. Soc. 121, 8728-8740.]); Dias et al. (2001[Dias, E. L., Brookhart, M. & White, P. S. (2001). Chem. Commun. pp. 423-424.]); Liu et al. (2009[Liu, P., Zhou, L., Li, X. & He, R. (2009). J. Organomet. Chem. 694, 2290-2294.]); Wieder et al. (2011[Wieder, N. L., Carroll, P. J. & Berry, D. H. (2011). Organometallics, 30, 2125-2136.]); Darmon et al. (2012[Darmon, J. M., Stieber, S. C. E., Sylvester, K. T., Fernández, I., Lobkovsky, E., Semproni, S. P., Bill, E., Wieghardt, K., DeBeer, S. & Chirik, P. J. (2012). J. Am. Chem. Soc. 134, 17125-17137.]). For the synthesis of 2,6-bis­[1-(2,4,6-tri­methyl­phenyl­imino)­eth­yl]pyridine, see: Britovsek et al. (1999[Britovsek, G. J. P., Bruce, M., Gibson, V. C., Kimberley, B. S., Maddox, P. J., Mastroianni, S., McTavish, S. J., Redshaw, C., Solan, G. A., Strömberg, S., White, A. J. P. & Williams, D. J. (1999). J. Am. Chem. Soc. 121, 8728-8740.]).

[Scheme 1]

Experimental

Crystal data
  • C27H31N3

  • Mr = 397.55

  • Triclinic, [P \overline 1]

  • a = 8.2098 (3) Å

  • b = 11.4125 (4) Å

  • c = 13.0619 (4) Å

  • [alpha] = 79.224 (3)°

  • [beta] = 77.066 (3)°

  • [gamma] = 76.645 (3)°

  • V = 1148.65 (7) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 0.52 mm-1

  • T = 150 K

  • 0.5 × 0.4 × 0.3 mm

Data collection
  • Oxford Diffraction Xcalibur (Ruby, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.]) Tmin = 0.679, Tmax = 1.000

  • 12720 measured reflections

  • 4330 independent reflections

  • 4028 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.123

  • S = 1.04

  • 4330 reflections

  • 279 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the (N1,C2-C6) ring.

D-H...A D-H H...A D...A D-H...A
C26-H26...N9i 0.95 2.64 3.5522 (18) 162
C28-H28B...Cg1ii 0.98 2.91 3.6715 (16) 135
Symmetry codes: (i) x+1, y-1, z; (ii) x+1, y, z.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5280 ).


Acknowledgements

We gratefully acknowledge financial support from the Royal Society (ABC) and the University of Warwick.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.
Britovsek, G. J. P., Bruce, M., Gibson, V. C., Kimberley, B. S., Maddox, P. J., Mastroianni, S., McTavish, S. J., Redshaw, C., Solan, G. A., Strömberg, S., White, A. J. P. & Williams, D. J. (1999). J. Am. Chem. Soc. 121, 8728-8740.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Darmon, J. M., Stieber, S. C. E., Sylvester, K. T., Fernández, I., Lobkovsky, E., Semproni, S. P., Bill, E., Wieghardt, K., DeBeer, S. & Chirik, P. J. (2012). J. Am. Chem. Soc. 134, 17125-17137.  [Web of Science] [CSD] [CrossRef] [ChemPort] [PubMed]
Dias, E. L., Brookhart, M. & White, P. S. (2001). Chem. Commun. pp. 423-424.  [CSD] [CrossRef]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Liu, P., Zhou, L., Li, X. & He, R. (2009). J. Organomet. Chem. 694, 2290-2294.  [CSD] [CrossRef] [ChemPort]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Wieder, N. L., Carroll, P. J. & Berry, D. H. (2011). Organometallics, 30, 2125-2136.  [CSD] [CrossRef] [ChemPort]


Acta Cryst (2014). E70, o73  [ doi:10.1107/S1600536813033801 ]

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