Crystal structure of (1S,2R,6R,7R,8S,12S)-4,10,17-triphenyl-15-thia-4,10-diazapentacyclo[5.5.5.01,16.02,6.08,12]heptadeca-13,16-diene-3,5,9,11-tetrone p-xylene hemisolvate

Wayland E. Noland; Neil J. Kroll; Matthew P. Huisenga; Ruixian A. Yue; Simon B. Lang; Nathan D. Klein; Kenneth J. Tritch

doi:10.1107/S1600536814025094

Crystal structure of (1S,2R,6R,7R,8S,12S)-4,10,17-triphenyl-15-thia-4,10-diazapentacyclo[5.5.5.0^1,16.0^2,6.0^8,12]heptadeca-13,16-diene-3,5,9,11-tetrone p-xylene hemisolvate

Wayland E. Noland, Neil J. Kroll, Matthew P. Huisenga, Ruixian A. Yue, Simon B. Lang, Nathan D. Klein, Kenneth J. Tritch

Chemistry (Twin Cities)

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

1 Scopus citations

Abstract

The title tetrone compound, C₃₂H₂₂N₂O₄S· 0.5C₈H₁₀, is the major product (50% yield) of an attempted Diels-Alder reaction of 2-(α-styryl)thiophene with N-phenylmaleimide (2 equivalents) in toluene. Recrystallization of the resulting powder from p-xylene gave the title hemisolvate; the p-xylene molecule is located about an inversion center. In the crystal, the primary tetrone contacts are between a carbonyl O atom and the four flagpole H atoms of the bicyclo[2.2.2]octene core, forming chains along [001].

Original language	English (US)
Pages (from-to)	550-554
Number of pages	5
Journal	Acta Crystallographica Section E: Structure Reports Online
Volume	70
Issue number	12
DOIs	https://doi.org/10.1107/S1600536814025094
State	Published - Dec 1 2014

Bibliographical note

Publisher Copyright:
© 2014.

Keywords

autoxidation
crystal structure
cycloaddition
double addition
thiophene

Publisher link

10.1107/S1600536814025094

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Noland, W. E., Kroll, N. J., Huisenga, M. P., Yue, R. A., Lang, S. B., Klein, N. D., & Tritch, K. J. (2014). Crystal structure of (1S,2R,6R,7R,8S,12S)-4,10,17-triphenyl-15-thia-4,10-diazapentacyclo[5.5.5.0^1,16.0^2,6.0^8,12]heptadeca-13,16-diene-3,5,9,11-tetrone p-xylene hemisolvate. Acta Crystallographica Section E: Structure Reports Online, 70(12), 550-554. https://doi.org/10.1107/S1600536814025094

Crystal structure of (1S,2R,6R,7R,8S,12S)-4,10,17-triphenyl-15-thia-4,10-diazapentacyclo[5.5.5.0^1,16.0^2,6.0^8,12]heptadeca-13,16-diene-3,5,9,11-tetrone p-xylene hemisolvate. / Noland, Wayland E.; Kroll, Neil J.; Huisenga, Matthew P. et al.
In: Acta Crystallographica Section E: Structure Reports Online, Vol. 70, No. 12, 01.12.2014, p. 550-554.

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

Noland, WE, Kroll, NJ, Huisenga, MP, Yue, RA, Lang, SB, Klein, ND & Tritch, KJ 2014, 'Crystal structure of (1S,2R,6R,7R,8S,12S)-4,10,17-triphenyl-15-thia-4,10-diazapentacyclo[5.5.5.0^1,16.0^2,6.0^8,12]heptadeca-13,16-diene-3,5,9,11-tetrone p-xylene hemisolvate', Acta Crystallographica Section E: Structure Reports Online, vol. 70, no. 12, pp. 550-554. https://doi.org/10.1107/S1600536814025094

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title = "Crystal structure of (1S,2R,6R,7R,8S,12S)-4,10,17-triphenyl-15-thia-4,10-diazapentacyclo[5.5.5.01,16.02,6.08,12]heptadeca-13,16-diene-3,5,9,11-tetrone p-xylene hemisolvate",

abstract = "The title tetrone compound, C32H22N2O4S· 0.5C8H10, is the major product (50% yield) of an attempted Diels-Alder reaction of 2-(α-styryl)thiophene with N-phenylmaleimide (2 equivalents) in toluene. Recrystallization of the resulting powder from p-xylene gave the title hemisolvate; the p-xylene molecule is located about an inversion center. In the crystal, the primary tetrone contacts are between a carbonyl O atom and the four flagpole H atoms of the bicyclo[2.2.2]octene core, forming chains along [001].",

keywords = "autoxidation, crystal structure, cycloaddition, double addition, thiophene",

author = "Noland, {Wayland E.} and Kroll, {Neil J.} and Huisenga, {Matthew P.} and Yue, {Ruixian A.} and Lang, {Simon B.} and Klein, {Nathan D.} and Tritch, {Kenneth J.}",

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T1 - Crystal structure of (1S,2R,6R,7R,8S,12S)-4,10,17-triphenyl-15-thia-4,10-diazapentacyclo[5.5.5.01,16.02,6.08,12]heptadeca-13,16-diene-3,5,9,11-tetrone p-xylene hemisolvate

AU - Noland, Wayland E.

AU - Kroll, Neil J.

AU - Huisenga, Matthew P.

AU - Yue, Ruixian A.

AU - Lang, Simon B.

AU - Klein, Nathan D.

AU - Tritch, Kenneth J.

PY - 2014/12/1

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N2 - The title tetrone compound, C32H22N2O4S· 0.5C8H10, is the major product (50% yield) of an attempted Diels-Alder reaction of 2-(α-styryl)thiophene with N-phenylmaleimide (2 equivalents) in toluene. Recrystallization of the resulting powder from p-xylene gave the title hemisolvate; the p-xylene molecule is located about an inversion center. In the crystal, the primary tetrone contacts are between a carbonyl O atom and the four flagpole H atoms of the bicyclo[2.2.2]octene core, forming chains along [001].

AB - The title tetrone compound, C32H22N2O4S· 0.5C8H10, is the major product (50% yield) of an attempted Diels-Alder reaction of 2-(α-styryl)thiophene with N-phenylmaleimide (2 equivalents) in toluene. Recrystallization of the resulting powder from p-xylene gave the title hemisolvate; the p-xylene molecule is located about an inversion center. In the crystal, the primary tetrone contacts are between a carbonyl O atom and the four flagpole H atoms of the bicyclo[2.2.2]octene core, forming chains along [001].

KW - autoxidation

KW - crystal structure

KW - cycloaddition

KW - double addition

KW - thiophene

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