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Structure of the co-crystalline solid formed between 1,4-dichloronaphthalene-2,3-diol and dioxane

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Abstract

The 1,4-dichloro-(1) and 1,4-dibromo-(2) derivatives of naphthalene-2,3-diol crystallise in structures containing acetic acid or dioxane solvent molecules. X-ray crystallographic examination of the compound formed between1 and dioxane is reported here [(C10H6Cl2O2)2·(C4H8O2),P21/c,a=12.358(3),b=4.9930(7),c=19.167(4) Å,β=96.09(1)0,Z=2,R=0.035] and this structure is analysed in crystal engineering terms. The compound is a co-crystalline material involving two types of hydrogen bonding: one phenolic group participates in a

$$\begin{gathered} ...{\text{OH }}...{\text{OH }}...{\text{OH}} \hfill \\ {\text{ | | |}} \hfill \\ {\text{ Ar Ar Ar}} \hfill \\ \end{gathered} $$

chain, while the second phenolic group hydrogen bonds to a dioxane. Extension of the hydrogen bonding network through the second dioxane oxygen results in heavily corrugated layers. Neighbouring layers interact by a combination of aromatic face-face and edge-face interactions similar to a partial coronene-type γ packing to complete the structure.

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Authors and Affiliations

  1. School of Chemistry, The University of New South Wales, 2052, Sydney, Australia

    Paul D. Ahn, Roger Bishop, Donald C. Craig & Marcia L. Scudder

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  1. Paul D. Ahn
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  2. Roger Bishop
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  3. Donald C. Craig
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  4. Marcia L. Scudder
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Additional information

Supplementary Data relating to this article are deposited with the British Library as supplementary publication No. SUP 82184 (11 pages).

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Ahn, P.D., Bishop, R., Craig, D.C. et al. Structure of the co-crystalline solid formed between 1,4-dichloronaphthalene-2,3-diol and dioxane. J Incl Phenom Macrocycl Chem 20, 267–276 (1994). https://doi.org/10.1007/BF00708772

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  • DOI: https://doi.org/10.1007/BF00708772

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