Crystal structure of (±)-(1SR,5SR,6SR,7SR,10SR,-11 SR,13SR)-13-benzyloxy-7-methoxymethoxy-11,15,18,18-tetramethyl-3-oxo-2,4-dioxatetra-cyclo[12.3.1.01,5.06,11]octadeca-14,16-dien-10-yl benzoate

Takeshi Oishi, Keisuke Fukaya, Yu Yamaguchi, Tomoya Sugai, Ami Watanabe, Takaaki Sato, Noritaka Chida, Hiroyuki Ishida

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

In the title compound, C36H42O8, the dioxolane ring adopts a twist conformation; the two adjacent C atoms deviate alternately from the mean plane of other atoms by - 0.287 (5) and 0.174 (5) Å. The cyclohexane, cyclohexadiene and central cyclooctane rings show chair, half-chair and boat-chair forms, respectively. As a result of the strained ring system, the tetrasubsituted olefin in the cyclohexadiene is skewed from an ideal planar structure. In the crystal, C - H⋯O hydrogen bonds connect the molecules into a sheet parallel to (100). The sheets are further linked by other weak C - H⋯O and C - H⋯π interactions, forming a three-dimensional network.

Original languageEnglish
Pages (from-to)490-493
Number of pages4
JournalActa Crystallographica Section E: Structure Reports Online
Volume71
Issue number5
DOIs
Publication statusPublished - May 1 2015

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Benzoates
seats
Crystal structure
Atoms
crystal structure
rings
Alkenes
Boats
Cyclohexane
Olefins
Conformations
Hydrogen bonds
planar structures
boats
cyclohexane
Crystals
alkenes
Molecules
atoms
hydrogen bonds

Keywords

  • C - H⋯π interactions
  • Crystal structure
  • Hydrogen bonding
  • Hydrogen bonds
  • Paclitaxel
  • Taxane skeleton

ASJC Scopus subject areas

  • Condensed Matter Physics
  • Materials Science(all)
  • Chemistry(all)

Cite this

Crystal structure of (±)-(1SR,5SR,6SR,7SR,10SR,-11 SR,13SR)-13-benzyloxy-7-methoxymethoxy-11,15,18,18-tetramethyl-3-oxo-2,4-dioxatetra-cyclo[12.3.1.01,5.06,11]octadeca-14,16-dien-10-yl benzoate. / Oishi, Takeshi; Fukaya, Keisuke; Yamaguchi, Yu; Sugai, Tomoya; Watanabe, Ami; Sato, Takaaki; Chida, Noritaka; Ishida, Hiroyuki.

In: Acta Crystallographica Section E: Structure Reports Online, Vol. 71, No. 5, 01.05.2015, p. 490-493.

Research output: Contribution to journalArticle

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abstract = "In the title compound, C36H42O8, the dioxolane ring adopts a twist conformation; the two adjacent C atoms deviate alternately from the mean plane of other atoms by - 0.287 (5) and 0.174 (5) {\AA}. The cyclohexane, cyclohexadiene and central cyclooctane rings show chair, half-chair and boat-chair forms, respectively. As a result of the strained ring system, the tetrasubsituted olefin in the cyclohexadiene is skewed from an ideal planar structure. In the crystal, C - H⋯O hydrogen bonds connect the molecules into a sheet parallel to (100). The sheets are further linked by other weak C - H⋯O and C - H⋯π interactions, forming a three-dimensional network.",
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AU - Oishi, Takeshi

AU - Fukaya, Keisuke

AU - Yamaguchi, Yu

AU - Sugai, Tomoya

AU - Watanabe, Ami

AU - Sato, Takaaki

AU - Chida, Noritaka

AU - Ishida, Hiroyuki

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N2 - In the title compound, C36H42O8, the dioxolane ring adopts a twist conformation; the two adjacent C atoms deviate alternately from the mean plane of other atoms by - 0.287 (5) and 0.174 (5) Å. The cyclohexane, cyclohexadiene and central cyclooctane rings show chair, half-chair and boat-chair forms, respectively. As a result of the strained ring system, the tetrasubsituted olefin in the cyclohexadiene is skewed from an ideal planar structure. In the crystal, C - H⋯O hydrogen bonds connect the molecules into a sheet parallel to (100). The sheets are further linked by other weak C - H⋯O and C - H⋯π interactions, forming a three-dimensional network.

AB - In the title compound, C36H42O8, the dioxolane ring adopts a twist conformation; the two adjacent C atoms deviate alternately from the mean plane of other atoms by - 0.287 (5) and 0.174 (5) Å. The cyclohexane, cyclohexadiene and central cyclooctane rings show chair, half-chair and boat-chair forms, respectively. As a result of the strained ring system, the tetrasubsituted olefin in the cyclohexadiene is skewed from an ideal planar structure. In the crystal, C - H⋯O hydrogen bonds connect the molecules into a sheet parallel to (100). The sheets are further linked by other weak C - H⋯O and C - H⋯π interactions, forming a three-dimensional network.

KW - C - H⋯π interactions

KW - Crystal structure

KW - Hydrogen bonding

KW - Hydrogen bonds

KW - Paclitaxel

KW - Taxane skeleton

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