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; H. Ishida

doi:10.1107/S2056989015007136

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[12.3.1.0^1,5.0^6,11]octadeca-14,16-dien-10-yl benzoate

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

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	490-493
Number of pages	4
Journal	Acta Crystallographica Section E: Structure Reports Online
Volume	71
Issue number	5
DOIs	https://doi.org/10.1107/S2056989015007136
Publication status	Published - May 1 2015

Keywords

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

ASJC Scopus subject areas

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

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10.1107/S2056989015007136

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Oishi, T., Fukaya, K., Yamaguchi, Y., Sugai, T., Watanabe, A., Sato, T., Chida, N., & Ishida, H. (2015). 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[12.3.1.0^1,5.0^6,11]octadeca-14,16-dien-10-yl benzoate. Acta Crystallographica Section E: Structure Reports Online, 71(5), 490-493. https://doi.org/10.1107/S2056989015007136

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[12.3.1.0^1,5.0^6,11]octadeca-14,16-dien-10-yl benzoate. / Oishi, Takeshi; Fukaya, Keisuke; Yamaguchi, Yu; Sugai, Tomoya; Watanabe, Ami; Sato, Takaaki; Chida, Noritaka; Ishida, H.

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

Research output: Contribution to journal › Article › peer-review

Oishi, T, Fukaya, K, Yamaguchi, Y, Sugai, T, Watanabe, A, Sato, T, Chida, N & Ishida, H 2015, '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[12.3.1.0^1,5.0^6,11]octadeca-14,16-dien-10-yl benzoate', Acta Crystallographica Section E: Structure Reports Online, vol. 71, no. 5, pp. 490-493. https://doi.org/10.1107/S2056989015007136

Oishi T, Fukaya K, Yamaguchi Y, Sugai T, Watanabe A, Sato T et al. 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[12.3.1.0^1,5.0^6,11]octadeca-14,16-dien-10-yl benzoate. Acta Crystallographica Section E: Structure Reports Online. 2015 May 1;71(5):490-493. https://doi.org/10.1107/S2056989015007136

Oishi, Takeshi ; Fukaya, Keisuke ; Yamaguchi, Yu ; Sugai, Tomoya ; Watanabe, Ami ; Sato, Takaaki ; Chida, Noritaka ; Ishida, H. / 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[12.3.1.0^1,5.0^6,11]octadeca-14,16-dien-10-yl benzoate. In: Acta Crystallographica Section E: Structure Reports Online. 2015 ; Vol. 71, No. 5. pp. 490-493.

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title = "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",

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.",

keywords = "C - H⋯π interactions, Crystal structure, Hydrogen bonding, Hydrogen bonds, Paclitaxel, Taxane skeleton",

author = "Takeshi Oishi and Keisuke Fukaya and Yu Yamaguchi and Tomoya Sugai and Ami Watanabe and Takaaki Sato and Noritaka Chida and H. Ishida",

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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, H.

PY - 2015/5/1

Y1 - 2015/5/1

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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