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
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 biphen...
Main Authors: | , , |
---|---|
Format: | Article |
Language: | English |
Published: |
International Union of Crystallography
2018-05-01
|
Series: | Acta Crystallographica Section E: Crystallographic Communications |
Subjects: | |
Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989017016589 |
id |
doaj-81cbb27009be426db1d1f63b61201ab3 |
---|---|
record_format |
Article |
spelling |
doaj-81cbb27009be426db1d1f63b61201ab32020-11-25T00:11:01ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902018-05-0174559459910.1107/S2056989017016589su5401An exploration of O—H...O and C—H...π interactions in a long-chain-ester-substituted phenylphenol: methyl 10-[4-(4-hydroxyphenyl)phenoxy]decanoateDavid K. Geiger0H. Cristina Geiger1Dominic L. Morell2Department of Chemistry, SUNY-College at Geneseo, Geneseo, NY 14454, USADepartment of Chemistry, SUNY-College at Geneseo, Geneseo, NY 14454, USADepartment of Chemistry, SUNY-College at Geneseo, Geneseo, NY 14454, USAAn 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.http://scripts.iucr.org/cgi-bin/paper?S2056989017016589crystal structureHirshfeld surfaceenergy frameworkinteraction energyhydrogen bondsC—H...π interactions |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
David K. Geiger H. Cristina Geiger Dominic L. Morell |
spellingShingle |
David K. Geiger H. Cristina Geiger Dominic L. Morell 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 Acta Crystallographica Section E: Crystallographic Communications crystal structure Hirshfeld surface energy framework interaction energy hydrogen bonds C—H...π interactions |
author_facet |
David K. Geiger H. Cristina Geiger Dominic L. Morell |
author_sort |
David K. Geiger |
title |
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 |
title_short |
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 |
title_full |
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 |
title_fullStr |
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 |
title_full_unstemmed |
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 |
title_sort |
exploration of o—h...o and c—h...π interactions in a long-chain-ester-substituted phenylphenol: methyl 10-[4-(4-hydroxyphenyl)phenoxy]decanoate |
publisher |
International Union of Crystallography |
series |
Acta Crystallographica Section E: Crystallographic Communications |
issn |
2056-9890 |
publishDate |
2018-05-01 |
description |
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. |
topic |
crystal structure Hirshfeld surface energy framework interaction energy hydrogen bonds C—H...π interactions |
url |
http://scripts.iucr.org/cgi-bin/paper?S2056989017016589 |
work_keys_str_mv |
AT davidkgeiger anexplorationofohoandchpinteractionsinalongchainestersubstitutedphenylphenolmethyl1044hydroxyphenylphenoxydecanoate AT hcristinageiger anexplorationofohoandchpinteractionsinalongchainestersubstitutedphenylphenolmethyl1044hydroxyphenylphenoxydecanoate AT dominiclmorell anexplorationofohoandchpinteractionsinalongchainestersubstitutedphenylphenolmethyl1044hydroxyphenylphenoxydecanoate AT davidkgeiger explorationofohoandchpinteractionsinalongchainestersubstitutedphenylphenolmethyl1044hydroxyphenylphenoxydecanoate AT hcristinageiger explorationofohoandchpinteractionsinalongchainestersubstitutedphenylphenolmethyl1044hydroxyphenylphenoxydecanoate AT dominiclmorell explorationofohoandchpinteractionsinalongchainestersubstitutedphenylphenolmethyl1044hydroxyphenylphenoxydecanoate |
_version_ |
1725405629919526912 |