Crystal structure of 9-methacryloylanthracene

Aditya Agrahari; Patrick O. Wagers; Steven M. Schildcrout; John Masnovi; Wiley J. Youngs; W. T A Harrison

doi:10.1107/S2056989015004090

Crystal structure of 9-methacryloylanthracene

Aditya Agrahari
, Patrick O. Wagers
, Steven M. Schildcrout
, John Masnovi^*
, Wiley J. Youngs
, W. T A Harrison (Editor)

^*Corresponding author for this work

Chemistry

Cleveland State University
University of Akron
Youngstown State University

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

8 Citations (Scopus)

15 Downloads (Pure)

Abstract

In the title compound, C₁₈H₁₄O, with systematic name 1-(anthracen-9-yl)-2-methylprop-2-en-1-one, the ketonic C atom lies 0.2030 (16) Å out of the anthryl-ring-system plane. The dihedral angle between the planes of the anthryl and methacryloyl moieties is 88.30 (3)° and the stereochemistry about the Csp² - Csp² bond in the side chain is transoid. In the crystal, the end rings of the anthryl units in adjacent molecules associate in parallel-planar orientations [shortest centroid-centroid distance = 3.6320 (7) Å]. A weak hydrogen bond is observed between an aromatic H atom and the O atom of a molecule displaced by translation in the a-axis direction, forming sheets of parallel-planar anthryl groups packing in this direction.

Original language	English
Pages (from-to)	357-359
Number of pages	3
Journal	Acta Crystallographica Section E: Structure Reports Online
Volume	71
Issue number	4
Early online date	11 Mar 2015
DOIs	https://doi.org/10.1107/S2056989015004090
Publication status	Published - 1 Apr 2015

Bibliographical note

The authors would like to thank the Graduate College and Chemistry Department at Cleveland State University for support, the Ohio Supercomputing Center for a grant of computer time, and the National Science Foundation (CHE-0840446) for funds used to purchase the Bruker APEXII DUO X-ray diffractometer used in this research.

Keywords

Acetylanthracene
Aldol
Crystal structure
Methylation
Stereochemistry

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10.1107/S2056989015004090Licence: CC BY

Crystal structure Final published version, 453 KBLicence: Other

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title = "Crystal structure of 9-methacryloylanthracene",

abstract = "In the title compound, C18H14O, with systematic name 1-(anthracen-9-yl)-2-methylprop-2-en-1-one, the ketonic C atom lies 0.2030 (16) {\AA} out of the anthryl-ring-system plane. The dihedral angle between the planes of the anthryl and methacryloyl moieties is 88.30 (3)° and the stereochemistry about the Csp2 - Csp2 bond in the side chain is transoid. In the crystal, the end rings of the anthryl units in adjacent molecules associate in parallel-planar orientations [shortest centroid-centroid distance = 3.6320 (7) {\AA}]. A weak hydrogen bond is observed between an aromatic H atom and the O atom of a molecule displaced by translation in the a-axis direction, forming sheets of parallel-planar anthryl groups packing in this direction.",

keywords = "Acetylanthracene, Aldol, Crystal structure, Methylation, Stereochemistry",

author = "Aditya Agrahari and Wagers, \{Patrick O.\} and Schildcrout, \{Steven M.\} and John Masnovi and Youngs, \{Wiley J.\} and Harrison, \{W. T A\}",

note = "The authors would like to thank the Graduate College and Chemistry Department at Cleveland State University for support, the Ohio Supercomputing Center for a grant of computer time, and the National Science Foundation (CHE-0840446) for funds used to purchase the Bruker APEXII DUO X-ray diffractometer used in this research.",

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doi = "10.1107/S2056989015004090",

language = "English",

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journal = "Acta Crystallographica Section E: Structure Reports Online",

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T1 - Crystal structure of 9-methacryloylanthracene

AU - Agrahari, Aditya

AU - Wagers, Patrick O.

AU - Schildcrout, Steven M.

AU - Masnovi, John

AU - Youngs, Wiley J.

A2 - Harrison, W. T A

N1 - The authors would like to thank the Graduate College and Chemistry Department at Cleveland State University for support, the Ohio Supercomputing Center for a grant of computer time, and the National Science Foundation (CHE-0840446) for funds used to purchase the Bruker APEXII DUO X-ray diffractometer used in this research.

PY - 2015/4/1

Y1 - 2015/4/1

N2 - In the title compound, C18H14O, with systematic name 1-(anthracen-9-yl)-2-methylprop-2-en-1-one, the ketonic C atom lies 0.2030 (16) Å out of the anthryl-ring-system plane. The dihedral angle between the planes of the anthryl and methacryloyl moieties is 88.30 (3)° and the stereochemistry about the Csp2 - Csp2 bond in the side chain is transoid. In the crystal, the end rings of the anthryl units in adjacent molecules associate in parallel-planar orientations [shortest centroid-centroid distance = 3.6320 (7) Å]. A weak hydrogen bond is observed between an aromatic H atom and the O atom of a molecule displaced by translation in the a-axis direction, forming sheets of parallel-planar anthryl groups packing in this direction.

AB - In the title compound, C18H14O, with systematic name 1-(anthracen-9-yl)-2-methylprop-2-en-1-one, the ketonic C atom lies 0.2030 (16) Å out of the anthryl-ring-system plane. The dihedral angle between the planes of the anthryl and methacryloyl moieties is 88.30 (3)° and the stereochemistry about the Csp2 - Csp2 bond in the side chain is transoid. In the crystal, the end rings of the anthryl units in adjacent molecules associate in parallel-planar orientations [shortest centroid-centroid distance = 3.6320 (7) Å]. A weak hydrogen bond is observed between an aromatic H atom and the O atom of a molecule displaced by translation in the a-axis direction, forming sheets of parallel-planar anthryl groups packing in this direction.

KW - Acetylanthracene

KW - Aldol

KW - Crystal structure

KW - Methylation

KW - Stereochemistry

UR - https://www.scopus.com/pages/publications/84928107503

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DO - 10.1107/S2056989015004090

M3 - Article

AN - SCOPUS:84928107503

SN - 1600-5368

VL - 71

SP - 357

EP - 359

JO - Acta Crystallographica Section E: Structure Reports Online

JF - Acta Crystallographica Section E: Structure Reports Online

IS - 4

ER -

Crystal structure of 9-methacryloylanthracene

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