Polymorphic crystals of oxacalix[4]arene with 1,3-alternate conformations of S 4 and C 2 symmetry

Akiko Hori, Erina Betsugi, Yoshinori Ikumura, Kenji Yoza

Research output: Contribution to journalArticle

Abstract

Calix[4]arene and oxacalix[4]arene derivatives have eight possible conformations in the up and down directions of their four aromatic rings from the mean plane of a bridged central ring, the conformations of which determine the functionality of the host frameworks. Despite being a known compound for five decades, oxacalix[4]arene, C 24 H 16 O 4 , has not been characterized previously by crystallographic methods. It crystallizes from hexane/CH 2 Cl 2 solution to give two polymorphs, i.e. prismatic and block-shaped crystals as twisted 1,3-alternate structures with S 4 and C 2 symmetry, respectively. These were previously suggested as the prefered stable conformations by density functional theory (DFT) calculations.

Original languageEnglish
JournalActa Crystallographica Section C: Structural Chemistry
DOIs
Publication statusPublished - 2019 Jan 1

Fingerprint

Crystallization
Conformations
Crystals
rings
symmetry
crystals
Hexanes
methylidyne
density functional theory
Hexane
Polymorphism
Density functional theory
Derivatives

Keywords

  • calix[4]arene
  • crystal structure
  • DFT
  • oxacalix[4]arene
  • polymorphs

ASJC Scopus subject areas

  • Condensed Matter Physics
  • Physical and Theoretical Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

Cite this

Polymorphic crystals of oxacalix[4]arene with 1,3-alternate conformations of S 4 and C 2 symmetry . / Hori, Akiko; Betsugi, Erina; Ikumura, Yoshinori; Yoza, Kenji.

In: Acta Crystallographica Section C: Structural Chemistry, 01.01.2019.

Research output: Contribution to journalArticle

@article{43e81764a2054120a3ef022123f2aabe,
title = "Polymorphic crystals of oxacalix[4]arene with 1,3-alternate conformations of S 4 and C 2 symmetry",
abstract = "Calix[4]arene and oxacalix[4]arene derivatives have eight possible conformations in the up and down directions of their four aromatic rings from the mean plane of a bridged central ring, the conformations of which determine the functionality of the host frameworks. Despite being a known compound for five decades, oxacalix[4]arene, C 24 H 16 O 4 , has not been characterized previously by crystallographic methods. It crystallizes from hexane/CH 2 Cl 2 solution to give two polymorphs, i.e. prismatic and block-shaped crystals as twisted 1,3-alternate structures with S 4 and C 2 symmetry, respectively. These were previously suggested as the prefered stable conformations by density functional theory (DFT) calculations.",
keywords = "calix[4]arene, crystal structure, DFT, oxacalix[4]arene, polymorphs",
author = "Akiko Hori and Erina Betsugi and Yoshinori Ikumura and Kenji Yoza",
year = "2019",
month = "1",
day = "1",
doi = "10.1107/S2053229619001517",
language = "English",
journal = "Acta crystallographica. Section C, Structural chemistry",
issn = "2053-2296",
publisher = "John Wiley and Sons Inc.",

}

TY - JOUR

T1 - Polymorphic crystals of oxacalix[4]arene with 1,3-alternate conformations of S 4 and C 2 symmetry

AU - Hori, Akiko

AU - Betsugi, Erina

AU - Ikumura, Yoshinori

AU - Yoza, Kenji

PY - 2019/1/1

Y1 - 2019/1/1

N2 - Calix[4]arene and oxacalix[4]arene derivatives have eight possible conformations in the up and down directions of their four aromatic rings from the mean plane of a bridged central ring, the conformations of which determine the functionality of the host frameworks. Despite being a known compound for five decades, oxacalix[4]arene, C 24 H 16 O 4 , has not been characterized previously by crystallographic methods. It crystallizes from hexane/CH 2 Cl 2 solution to give two polymorphs, i.e. prismatic and block-shaped crystals as twisted 1,3-alternate structures with S 4 and C 2 symmetry, respectively. These were previously suggested as the prefered stable conformations by density functional theory (DFT) calculations.

AB - Calix[4]arene and oxacalix[4]arene derivatives have eight possible conformations in the up and down directions of their four aromatic rings from the mean plane of a bridged central ring, the conformations of which determine the functionality of the host frameworks. Despite being a known compound for five decades, oxacalix[4]arene, C 24 H 16 O 4 , has not been characterized previously by crystallographic methods. It crystallizes from hexane/CH 2 Cl 2 solution to give two polymorphs, i.e. prismatic and block-shaped crystals as twisted 1,3-alternate structures with S 4 and C 2 symmetry, respectively. These were previously suggested as the prefered stable conformations by density functional theory (DFT) calculations.

KW - calix[4]arene

KW - crystal structure

KW - DFT

KW - oxacalix[4]arene

KW - polymorphs

UR - http://www.scopus.com/inward/record.url?scp=85061494747&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85061494747&partnerID=8YFLogxK

U2 - 10.1107/S2053229619001517

DO - 10.1107/S2053229619001517

M3 - Article

JO - Acta crystallographica. Section C, Structural chemistry

JF - Acta crystallographica. Section C, Structural chemistry

SN - 2053-2296

ER -