[5,10,15,20-Tetrakis (4-methoxyphenyl)-porphyrinato] zinc dichloromethane disolvate Page: 1
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supplementary materials
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Acta Cryst. (2013). E69, m471 [doi:10.1107/S1600536813019338]
[5,10,15,20-Tetrakis(4-methoxyphenyl)porphyrinato]zinc dichloromethane
disolvate
Sean McGill, Vladimir N. Nesterov and Stephanie L. Gould
Comment
While in pursuit of understanding zinc porphyrin coordination to alkyl alcohol solvents through the central zinc atom, we
sought to crystallize zinc 5,10,15,20-tetrakis(p-methoxyphenyl)porphyrin with octanol. The resulting deep red crystals
did not contain any octanol coordination, but contained a well ordered porphyrin structure with dichloromethane solvent
molecules. The crystal structure of the title compound is presented herein.
The title porphyrin (Fig. 1) has a zinc atom located on a center of inversion and hence the exact center of the mean-
plane of the 24 other Non-H atoms with a r.m.s. deviation of the fitted atom = 0.0288A. The p-methoxy-substituted
benzene rings form dihedral angles of 59.38 (6) (C11-C16) and 66.77 (6) (C17-C22) with the porphyrin mean plane.
The crystal packing (Fig. 2) is characterized by close contacts between the Zn" ion with two symmetry related molecules
(-x+1, y-1/2, -z+1/2 and x, -y+3/2, z+1/2) through the oxygen atoms of a methoxy-phenyl group (Zn--O = 2.694 (2)A)
forming a two-dimensional network parallel to (100). This distance is smaller than the sum of corresponding Van der
Waals radii of atoms 2.910 A (Bondi, 1964). There are some reports of Zn--O coordination bonds in porphyrins (Bhuyan
& Sarkar, 2011; Adilov & Thalladi, 2007; Teo et al., 2003). These reports indicate a bond distance shorter than what is
found in the title compound.
Experimental
The synthesis of the title Zn complex was carried out according literature procedures (Adler et al., 1967). Dark red
crystals were grown by liquid diffusion of 1 ml octanol into a 3 ml dichloromethane solution containing 20 mg of zinc
5,10,15,20-tetrakis- (p-methoxyphenyl)porphyrin.
Refinement
All H atoms attached to C atoms were placed in idealized positions (C-H = 0.95-0.99 A) and allowed to ride on their
parent atoms. All H atoms were constrained so that U, (H) were equal to 1.2Ueq or 1.5Ueq of their respective parent
atoms.
Computing details
Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (Bruker, 2007); data reduction: SAINT (Bruker, 2007);
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 (Sheldrick, 2008).Acta Cryst. (2013). E69, m471 sup-i
sup-1
Acta Cryst. (2013). E69, m471
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McGill, Sean; Nesterov, Vladimir N. & Gould, Stephanie L. [5,10,15,20-Tetrakis (4-methoxyphenyl)-porphyrinato] zinc dichloromethane disolvate, article, July 24, 2013; [Chester, England]. (https://digital.library.unt.edu/ark:/67531/metadc333041/m1/2/: accessed April 16, 2024), University of North Texas Libraries, UNT Digital Library, https://digital.library.unt.edu; crediting UNT College of Arts and Sciences.