Crystal structure of (5-{3-[(1,4,7,10,13-penta-oxa-16-aza-cyclo-octa-decan-16-yl)carbonyl-amino]-phen-yl}-10,15,20-tri-phenyl-porphyrinato)cobalt(II).

Qi Wu,Jianfeng Li,Mingrui He

doi:10.1107/s2056989017007745

Abstract

In the title compound, [Co(C57H52N6O6)], the central CoII atom is coordinated by four pyrrole N atoms of the porphyrin core and one O atom of the crown ether. The complex has a distorted porphyrin core, with mean absolute core-atom displacements of 0.14 (10) (Ca), 0.20 (10) (Cb), 0.24 (4) (Cm) and 0.18 (10) Å (Cav), respectively. The axial Co-O bond length is 2.3380 (15) and the average Co-Np bond length is 1.968 (5) Å. Intra-molecular N-H⋯O and inter-molecular C-H⋯π inter-actions are observed.

Highlights

In the title compound, [Co(C57H52N6O6)], the central CoII atom is coordinated by four pyrrole N atoms of the porphyrin core and one O atom of the crown ether
There have been some reports on the single-crystal structures of crown etherporphyrinates, including chlorido[52-N-(4-aza-18-crown-6)methyl-54,104,154,20 4-tetra-tert-butyl-56-methyl-5,10,15,20tetraphenylporphyrinato]iron(III) (Dürr et al, 2007), 5,15{2,20 -[3,30 -(1,4,10,13-tetraoxa-7,16- diazacyclooctadecan-7,16diyl)dipropionamido]phenyl}-2,8,12,18-tetraethyl-3,7,13,17tetramethylporphyrin and the corresponding zinc(II)
In the crystal of the title compound (Fig. 1), the asymmetric unit contains one five-coordinate single-crowned porphyrin in which the oxygen atom (O3) of the crown ether ligates to the central cobalt(II) atom

Summary

Chemical context

Crown ether-porphyrinates have been developed to mimic the active site of the cytochrome c oxidase. There have been some reports on the single-crystal structures of crown etherporphyrinates, including chlorido[52-N-(4-aza-18-crown-6)methyl-54 ,104,154,20 4-tetra-tert-butyl-56-methyl-5,10,15,20tetraphenylporphyrinato]iron(III) (Dürr et al, 2007), 5,15{2,20 -[3,30 -(1,4,10,13-tetraoxa-7,16- diazacyclooctadecan-7,16diyl)dipropionamido]phenyl}-2,8,12,18-tetraethyl-3,7,13,17tetramethylporphyrin and the corresponding zinc(II). Compounds (Comte et al, 1998), 1,4,10,13-tetraoxa-7,16-diazacyclooctadecane-7,16-dicarboxylic acid{2,20-[10,20-bis-(3,5dimethoxyphenyl)porphyrin- -5,15-diyl]diphenyl}diamide and the corresponding zinc(II) and lead(II) compounds (Halime et al, 2007), aqua{5,15,10,20-bis[bis(2-(1,10-diaza-18crown-6-1,10-diyl)carbonylaminophenyl]porphyrinato}zinc(II) (Michaudet et al, 2000). The crystal structure of a cobalt(II) porphyrin complex, (5-{3-[(1,4,7,10,13-pentaoxa-16-azacyclooctadecan-16-yl)carbonylamino]phenyl}10,15,20-triphenylporphyrinato)cobalt(II), is reported. The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level

Structural commentary

Supramolecular features

Synthesis and crystallization

Refinement