[meso-Tetra­kis(4-heptyl­oxyphen­yl)porphyrinato]nickel(II)

Chen, L.; Zhao, H.-B.; Xie, Y.-J.; Yang, D.-L.; Wang, B.-Y.

doi:10.1107/S1600536810041942

Volume 66
Part 11
Page m1455
November 2010

Received 28 September 2010
Accepted 16 October 2010
Online 23 October 2010

Key indicators
Single-crystal X-ray study
T = 185 K
Mean (C-C) = 0.004 Å
R = 0.051
wR = 0.114
Data-to-parameter ratio = 14.8
Details

[meso-Tetrakis(4-heptyloxyphenyl)porphyrinato]nickel(II)

Liang Chen,^a Hong-Bin Zhao,^a,^b ^* Yu-Jia Xie,^a De-Liang Yang ^a and Bang-Ying Wang ^a

^aDepartment of Organic Chemistry, the College of Chemistry, Xiangtan University, Hunan 411105, People's Republic of China, and ^bEnvironmental Engineering, Dongguan University of Technology, Guangdong 523808, People's Republic of China
Correspondence e-mail: zhhbhanlf@163.com

In the title compound, [Ni(C₇₂H₈₄N₄O₄)], the four-coordinate Ni^II ion in the middle of the planar 24-membered porphyrin ring is located on a crystallograpic inversion center, with Ni-N distances of 1.946 (2)-1.951 (2) Å. The 4-heptyloxyphenyl groups are twisted with respect to the porphyrin mean plane, the dihedral angles being 88.5 (3) and 79.1 (2)°.

Related literature

For related structures, see: Scheidt (1977); Maclean et al. (1996); Jentzen et al. (1996). For background to porphyrins and metalloporphyrins, see: Kozaki et al. (2007); Kuciauskas et al. (1996); Suslick et al. (2005); Liu et al. (1985); Gross & Ini (1999); Wasielewski et al. (1993).

Experimental

Crystal data

[Ni(C₇₂H₈₄N₄O₄)]
M_r = 1128.14
Monoclinic, P 2₁ /c
a = 15.8843 (12) Å
b = 19.0602 (15) Å
c = 10.2398 (8) Å
= 91.221 (2)°
V = 3099.5 (4) Å³
Z = 2
Mo K radiation
= 0.37 mm^-1
T = 185 K
0.21 × 0.16 × 0.07 mm

Data collection

Bruker APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) T_min = 0.927, T_max = 0.975
14663 measured reflections
5469 independent reflections
3578 reflections with I > 2(I)
R_int = 0.062

Refinement

R[F² > 2(F²)] = 0.051
wR(F²) = 0.114
S = 0.96
5469 reflections
369 parameters
H-atom parameters constrained
_max = 0.36 e Å^-3
_min = -0.35 e Å^-3

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; 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: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FK2026 ).

Acknowledgements

This work was supported by National Analytical Research Center of Electrochemistry and Spectroscopy, Changchun Institute of Applied Chemistry, Changchun, China.

References

Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Gross, Z. & Ini, S. (1999). Org. Lett. 1, 2077-2080.
Jentzen, W., Turowska-Tyrk, I., Scheidt, W. R. & Shelnutt, J. A. (1996). Inorg. Chem. 35, 3559-3567.
Kozaki, M., Akita, K. & Okada, K. (2007). Org. Lett. 9, 1509-1592.
Kuciauskas, D., Lin, S., Seely, G. R., Moore, A. L., Moore, M. T. & Gust, D. (1996). J. Phys. Chem. 100, 15926-15932.
Liu, H. Y., Abdalmuhdi, I., Chang, C. K. & Anson, F. C. (1985). J. Phys. Chem. 89, 665-670.
Maclean, A. L., Foran, G. J., Kennedy, B. J., Turner, P. & Hambley, T. W. (1996). Aust. J. Chem. 49, 1273-1278.
Scheidt, W. R. (1977). Acc. Chem. Res. 10, 339-345.
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Suslick, K. S., Bhyrappa, P., Chou, J. H., Kosal, M. E., Nakagaki, S., Smithenry, D. W. & Wilson, S. R. (2005). Acc. Chem. Res. 38, 283-291.
Wasielewski, M. R., Gaines, G. L., Wiederrecht, G. P., Svec, W. A. & Niemczyk, M. P. (1993). J. Am. Chem. Soc. 115, 10442-10443.

metal-organic compounds