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Face-to-Face Stacking and Saddle Distortion of 5,10,15,20-Tetra(4-hydroxyphenyl)porphyrinatocopper(II) in Two New Solvates

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Abstract

The crystal structures of the methanol nitrobenzene sesquisolvate hemihydrate (1) and the 3.75-dimethyl sulfoxide solvate monohydrate (2) of 5,10,15,20-tetra(4-hydroxyphenyl)porphyrinatocopper(II) (CuTOHPP) are reported. Both 1 and 2 crystallise in the triclinic system with two molecules of the metalloporphyrin in the asymmetric unit (Z′ = 2). Compound 1 exhibits an extended two-dimensional hydrogen-bonded network in the crystal, whereas discrete hydrogen-bonded assemblies of CuTOHPP and solvent molecules are found in 2. Face-to-face stacking of the metalloporphyrin units and O–H⋯O hydrogen bonding interactions are identified as the most important solid-state organisational features in both 1 and 2. Saddle distortion of the metalloporphyrin units is encountered in both new solvates and there are no Cu⋯O interactions, despite four hydroxy groups on each porphyrin ligand and the presence of oxygen donor solvent molecules.

Graphical Abstract

The methanol nitrobenzene sesquisolvate hemihydrate and the 3.75-dimethyl sulfoxide solvate monohydrate of 5,10,15,20-tetra(4-hydroxyphenyl)porphyrinatocopper(II) both crystallise in the triclinic system with two molecules in the asymmetric unit (Z′ = 2), featuring face-to-face stacking of the saddle-distorted metalloporphyrin units.

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Notes

  1. The structure of CuTOHPP acetophenone tetrasolvate (CSD refcode: TEFREB) was described in the triclinic space group P1. There is, however, evidence that higher symmetry is present. The monoclinic space group C2 seems to be more appropriate than P1. A revised CIF has been submitted to The Cambridge Crystallographic Data Centre (CCDC: 1441615). Details are given in the supplementary material.

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Acknowledgements

We would like to thank Dr Wanning Hu for assistance in preparing the samples studied. The Deutsche Forschungsgemeinschaft (DFG) is acknowledged for financial support.

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Authors and Affiliations

  1. Lehrstuhl für Analytische Chemie, Ruhr-Universität Bochum, Universitätsstraße 150, 44780, Bochum, Germany

    Rüdiger W. Seidel

  2. Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470, Mülheim an der Ruhr, Germany

    Richard Goddard

  3. Institut für Anorganische Chemie, Rheinisch-Westfälische Technische Hochschule Aachen, Landoltweg 1, 52074, Aachen, Germany

    Iris M. Oppel

Authors
  1. Rüdiger W. Seidel
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  2. Richard Goddard
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  3. Iris M. Oppel
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Correspondence to Rüdiger W. Seidel.

Additional information

In memoriam Professor Teodor Silviu Balaban (1958–2016).

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Supplementary material 1 (DOCX 662 KB)

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Seidel, R.W., Goddard, R. & Oppel, I.M. Face-to-Face Stacking and Saddle Distortion of 5,10,15,20-Tetra(4-hydroxyphenyl)porphyrinatocopper(II) in Two New Solvates. J Chem Crystallogr 47, 187–197 (2017). https://doi.org/10.1007/s10870-017-0696-9

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  • DOI: https://doi.org/10.1007/s10870-017-0696-9

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