(5,15-Dianthracen-9-yl-10,20-dihexyl­porphyrinato)nickel(II): a planar nickel(II) porphyrin

Senge, M.O.; Davis, M.

doi:10.1107/S1600536810021434

Volume 66
Part 7
Page m790
July 2010

Received 3 June 2010
Accepted 4 June 2010
Online 16 June 2010

Key indicators
Single-crystal X-ray study
T = 118 K
Mean (C-C) = 0.003 Å
R = 0.039
wR = 0.087
Data-to-parameter ratio = 13.1
Details

(5,15-Dianthracen-9-yl-10,20-dihexylporphyrinato)nickel(II): a planar nickel(II) porphyrin

Mathias O. Senge ^a ^* and Mia Davis ^a

^aSFI Tetrapyrrole Laboratory, School of Chemistry, Trinity College Dublin, Dublin 2, Ireland
Correspondence e-mail: sengem@tcd.ie

The title compound, [Ni(C₆₀H₅₂N₄)], is an example of a meso tetrasubstituted nickel(II) porphyrin with both meso aryl and alkyl residues. The molecule exhibits a planar macrocycle with an average deviation of the 24 macrocycle atoms from their least-squares plane ( [Delta] 24) of 0.01 Å and an average Ni-N bond length of 1.960 (2) Å. The Ni^II atom lies on a center of inversion. The structure presents a rare example for a planar nickel(II) porphyrin, as meso-substituted nickel(II) porphyrins with either only meso-aryl or with meso-alkyl residues typically exhibit a ruffled conformation.

Related literature

For the conformation of porphyrins, see: Senge (2006). For porphyrins with mixed meso substituents, see: Senge et al. (2010). For Ni(II) porphyrin structures, see: Fleischer et al. (1964); Gallucci et al. (1982); Hoard (1973); Lee & Scheidt (1987); Senge et al. (1999, 2000) and Runge et al. (1999). For anthracenyl porphyrins see: Volz & Schäffer (1985); Davis et al. (2008); Sooambar et al. (2009). For the handling of the crystals, see: Hope (1994).

Experimental

Crystal data

[Ni(C₆₀H₅₂N₄)]
M_r = 887.77
Triclinic, $[P \overline 1]$
a = 7.797 (3) Å
b = 9.387 (3) Å
c = 15.285 (5) Å
= 97.246 (6)°
= 91.222 (4)°
= 91.402 (6)°
V = 1109.1 (7) Å³
Z = 1
Mo K radiation
= 0.48 mm^-1
T = 118 K
0.50 × 0.20 × 0.05 mm

Data collection

Rigaku Saturn724 diffractometer
17330 measured reflections
3875 independent reflections
3233 reflections with I > 2(I)
R_int = 0.070

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.087
S = 1.00
3875 reflections
296 parameters
H-atom parameters constrained
_max = 0.37 e Å^-3
_min = -0.40 e Å^-3

Table 1
Selected bond lengths (Å)

Ni-N22	1.9570 (17)
Ni-N21	1.9632 (17)

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2783 ).

Acknowledgements

This work was supported by a grant from Science Foundation Ireland (SFI P.I. 09/IN.1/B2650).

References

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