An exploration of O—H...O and C—H...π interactions in a long-chain-ester-substituted phenylphenol: methyl 10-[4-(4-hydroxyphenyl)phenoxy]decanoate

Abstract

An understanding of the driving forces resulting in crystallization vs organogel formation is essential to the development of modern soft materials. In the molecular structure of the title compound, methyl 10-[4-(4-hydroxyphenyl)phenoxy]decanoate (MBO10Me), C23H30O4, the aromatic rings of the biphenyl group are canted by 6.6 (2)° and the long-chain ester group has an extended conformation. In the crystal, molecules are linked by O—H...O hydrogen bonds, forming chains along [10\overline{3}]. The chains are linked by C—H...O hydrogen bonds, forming layers parallel to the ac plane. The layers are linked by C—H...π interactions, forming a three-dimensional supramolecular structure. The extended structure exhibits a lamellar sheet arrangement of molecules stacking along the b-axis direction. Each molecule has six nearest neighbors and the seven-molecule bundles stack to form a columnar superstructure. Interaction energies within the bundles are dominated by dispersion forces, whereas intercolumnar interactions have a greater electrostatic component.

Keywords

• crystal structure
• Hirshfeld surface
• energy framework
• interaction energy
• hydrogen bonds
• C—H...π interactions