4′-[2-(Trifluoro­meth­yl)phen­yl]-2,2′:6′,2′′-terpyridine

Ledwaba, P.; Munro, O.Q.; Stewart, K.

doi:10.1107/S1600536809002384

Volume 65
Part 2
Pages o376-o377
February 2009

Received 14 January 2009
Accepted 19 January 2009
Online 23 January 2009

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.052
wR = 0.148
Data-to-parameter ratio = 12.4
Details

4'-[2-(Trifluoromethyl)phenyl]-2,2':6',2''-terpyridine

Peter Ledwaba,^a Orde Q. Munro ^a and Kirsty Stewart ^a ^*

^aSchool of Chemical and Physical Sciences, University of KwaZulu-Natal, Scottsville 3209, South Africa
Correspondence e-mail: stewart@ukzn.ac.za

The title compound, C₂₂H₁₄F₃N₃, is a versatile tridentate N-donor ligand consisting of a terpyridyl (terpy) molecule substituted in the 4'-position by a phenyl group, itself substituted in an ortho-position by a bulky trifluoromethyl group. The phenyl ring is twisted as a result of steric interactions involving the bulky trifluoromethyl substituent. This is reflected in the dihedral angle between the mean plane through the C atoms of the phenyl ring and the terpyridyl unit being 69.2 (1)°. The crystal structure contains no short van der Waals contacts. However, the terpy units stack in a head-to-tail orientation perpendicular to the c axis. The structure is is loosely stabilized by [pi] - [pi] interactions between the terminal pyridine rings of adjacent molecules along the stack. The perpendicular distance between the mean planes through the terpy moieties of adjacent molecules is 3.4 (1) Å.

Related literature

For related structures, see: Bessel et al. (1992); Brandt et al. (1954); Dwyer & Mellor (1964); Field et al. (2002); Gillard (1983); Lindoy & Livingstone (1967); Morgan & Burstall (1932, 1934, 1938); Serpone et al. (1983); Storrier et al. (1997). For background, see Constable et al. (1990, 1992); Hunter & Sanders (1990); Kröhnke (1976); Thummel & Jahng (1985).

Experimental

Crystal data

C₂₂H₁₄F₃N₃
M_r = 377.36
Triclinic, $[P \overline 1]$
a = 7.767 (5) Å
b = 10.923 (3) Å
c = 11.748 (3) Å
= 75.64 (2)°
= 74.03 (4)°
= 72.93 (4)°
V = 900.8 (7) Å³
Z = 2
Mo K radiation
= 0.11 mm^-1
T = 293 (2) K
0.60 × 0.30 × 0.30 mm

Data collection

Oxford Diffraction Xcalibur2 CCD diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2003 $[Oxford Diffraction (2003). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.930, T_max = 0.969
3953 measured reflections
3155 independent reflections
2840 reflections with I > 2(I)
R_int = 0.032

Refinement

R[F² > 2(F²)] = 0.052
wR(F²) = 0.148
S = 1.06
3155 reflections
254 parameters
H-atom parameters constrained
_max = 0.43 e Å^-3
_min = -0.32 e Å^-3

Data collection: CrysAlis CCD (Oxford Diffraction, 2003 $[Oxford Diffraction (2003). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2003 $[Oxford Diffraction (2003). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2469 ).

Acknowledgements

The authors acknowledge financial support from the South African National Research Foundation and the Department of Labour. We also extend our appreciation to Professor John Field for helpful discussions and guidance.

References

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organic compounds