Crystal structure and Hirshfeld analysis of 3'-bromo-4-methylchalcone and 3'-cyano-4- methylchalcone

Zachary O Battaglia; Jordan T Kersten; Elise M Nicol; Paloma Whitworth; Kraig A Wheeler; Charlie L Hall; Jason Potticary; Victoria Hamilton; Simon R Hall; Gemma D’Ambruoso; Masaomi Matsumoto; Stephen D Warren; Matthew E Cremens

doi:10.1107/S2056989020011135

Crystal structure and Hirshfeld analysis of 3'-bromo-4-methylchalcone and 3'-cyano-4- methylchalcone

Zachary O Battaglia, Jordan T Kersten, Elise M Nicol, Paloma Whitworth, Kraig A Wheeler, Charlie L Hall, Jason Potticary, Victoria Hamilton, Simon R Hall, Gemma D’Ambruoso, Masaomi Matsumoto, Stephen D Warren, Matthew E Cremens

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Abstract

Two crystal structures of chalcones, or 1,3-diarylprop-2-en-1-ones, are
presented; both contain a methyl substitution on the 3-Ring, but differ on the
1-Ring, bromo versus cyano. The compounds are 30-bromo-4-methylchalcone
[systematic name: 1-(2-bromophenyl)-3-(4-methylphenyl)prop-2-en-1-one],
C16H13BrO, and 30-cyano-4-methylchalcone {systematic name: 2-[3-(4-methylphenyl)
prop-2-enoyl]benzonitrile}, C17H13NO. Both chalcones meaningfully
add to the large dataset of chalcone structures. The crystal structure of 30-cyano-
4-methylchalcone exhibits close contacts with the cyano nitrogen that do not
appear in previously reported disubstituted cyanochalcones, namely interactions
between the cyano nitrogen atom and a ring hydrogen atom as well as a methyl
hydrogen atom. The structure of 30-bromo-4-methylchalcone exhibits a type I
halogen bond, similar to that found in a previously reported structure for
4-bromo-30-methylchalcone.

Original language	English
Pages (from-to)	1496-1502
Number of pages	7
Journal	Acta Crystallographica Section E: Crystallographic Communications
Volume	E76
DOIs	https://doi.org/10.1107/S2056989020011135
Publication status	Accepted/In press - 25 Aug 2020

Research Groups and Themes

Inorganic & Materials

Keywords

crystal structure
chalcone
bromo
cyano
halogen bond
n-stacking
edge-to-face

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10.1107/S2056989020011135

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Battaglia, Z. O., Kersten, J. T., Nicol, E. M., Whitworth, P., Wheeler, K. A., Hall, C. L., Potticary, J., Hamilton, V., Hall, S. R., D’Ambruoso, G., Matsumoto, M., Warren, S. D., & Cremens, M. E. (Accepted/In press). Crystal structure and Hirshfeld analysis of 3'-bromo-4-methylchalcone and 3'-cyano-4- methylchalcone. Acta Crystallographica Section E: Crystallographic Communications, E76, 1496-1502. https://doi.org/10.1107/S2056989020011135

@article{1e4f88aeede54b2c88361cb572594c67,

title = "Crystal structure and Hirshfeld analysis of 3'-bromo-4-methylchalcone and 3'-cyano-4- methylchalcone",

abstract = "Two crystal structures of chalcones, or 1,3-diarylprop-2-en-1-ones, are presented; both contain a methyl substitution on the 3-Ring, but differ on the 1-Ring, bromo versus cyano. The compounds are 30-bromo-4-methylchalcone [systematic name: 1-(2-bromophenyl)-3-(4-methylphenyl)prop-2-en-1-one], C16H13BrO, and 30-cyano-4-methylchalcone \{systematic name: 2-[3-(4-methylphenyl) prop-2-enoyl]benzonitrile\}, C17H13NO. Both chalcones meaningfully add to the large dataset of chalcone structures. The crystal structure of 30-cyano- 4-methylchalcone exhibits close contacts with the cyano nitrogen that do not appear in previously reported disubstituted cyanochalcones, namely interactions between the cyano nitrogen atom and a ring hydrogen atom as well as a methyl hydrogen atom. The structure of 30-bromo-4-methylchalcone exhibits a type I halogen bond, similar to that found in a previously reported structure for 4-bromo-30-methylchalcone.",

keywords = "crystal structure, chalcone, bromo, cyano, halogen bond, n-stacking, edge-to-face",

author = "Battaglia, \{Zachary O\} and Kersten, \{Jordan T\} and Nicol, \{Elise M\} and Paloma Whitworth and Wheeler, \{Kraig A\} and Hall, \{Charlie L\} and Jason Potticary and Victoria Hamilton and Hall, \{Simon R\} and Gemma D{\textquoteright}Ambruoso and Masaomi Matsumoto and Warren, \{Stephen D\} and Cremens, \{Matthew E\}",

year = "2020",

month = aug,

day = "25",

doi = "10.1107/S2056989020011135",

language = "English",

volume = "E76",

pages = "1496--1502",

journal = "Acta Crystallographica Section E: Crystallographic Communications",

issn = "2056-9890",

publisher = "International Union of Crystallography",

}

Battaglia, ZO, Kersten, JT, Nicol, EM, Whitworth, P, Wheeler, KA, Hall, CL, Potticary, J, Hamilton, V, Hall, SR, D’Ambruoso, G, Matsumoto, M, Warren, SD & Cremens, ME 2020, 'Crystal structure and Hirshfeld analysis of 3'-bromo-4-methylchalcone and 3'-cyano-4- methylchalcone', Acta Crystallographica Section E: Crystallographic Communications, vol. E76, pp. 1496-1502. https://doi.org/10.1107/S2056989020011135

TY - JOUR

T1 - Crystal structure and Hirshfeld analysis of 3'-bromo-4-methylchalcone and 3'-cyano-4- methylchalcone

AU - Battaglia, Zachary O

AU - Kersten, Jordan T

AU - Nicol, Elise M

AU - Whitworth, Paloma

AU - Wheeler, Kraig A

AU - Hall, Charlie L

AU - Potticary, Jason

AU - Hamilton, Victoria

AU - Hall, Simon R

AU - D’Ambruoso, Gemma

AU - Matsumoto, Masaomi

AU - Warren, Stephen D

AU - Cremens, Matthew E

PY - 2020/8/25

Y1 - 2020/8/25

N2 - Two crystal structures of chalcones, or 1,3-diarylprop-2-en-1-ones, are presented; both contain a methyl substitution on the 3-Ring, but differ on the 1-Ring, bromo versus cyano. The compounds are 30-bromo-4-methylchalcone [systematic name: 1-(2-bromophenyl)-3-(4-methylphenyl)prop-2-en-1-one], C16H13BrO, and 30-cyano-4-methylchalcone {systematic name: 2-[3-(4-methylphenyl) prop-2-enoyl]benzonitrile}, C17H13NO. Both chalcones meaningfully add to the large dataset of chalcone structures. The crystal structure of 30-cyano- 4-methylchalcone exhibits close contacts with the cyano nitrogen that do not appear in previously reported disubstituted cyanochalcones, namely interactions between the cyano nitrogen atom and a ring hydrogen atom as well as a methyl hydrogen atom. The structure of 30-bromo-4-methylchalcone exhibits a type I halogen bond, similar to that found in a previously reported structure for 4-bromo-30-methylchalcone.

AB - Two crystal structures of chalcones, or 1,3-diarylprop-2-en-1-ones, are presented; both contain a methyl substitution on the 3-Ring, but differ on the 1-Ring, bromo versus cyano. The compounds are 30-bromo-4-methylchalcone [systematic name: 1-(2-bromophenyl)-3-(4-methylphenyl)prop-2-en-1-one], C16H13BrO, and 30-cyano-4-methylchalcone {systematic name: 2-[3-(4-methylphenyl) prop-2-enoyl]benzonitrile}, C17H13NO. Both chalcones meaningfully add to the large dataset of chalcone structures. The crystal structure of 30-cyano- 4-methylchalcone exhibits close contacts with the cyano nitrogen that do not appear in previously reported disubstituted cyanochalcones, namely interactions between the cyano nitrogen atom and a ring hydrogen atom as well as a methyl hydrogen atom. The structure of 30-bromo-4-methylchalcone exhibits a type I halogen bond, similar to that found in a previously reported structure for 4-bromo-30-methylchalcone.

KW - crystal structure

KW - chalcone

KW - bromo

KW - cyano

KW - halogen bond

KW - n-stacking

KW - edge-to-face

U2 - 10.1107/S2056989020011135

DO - 10.1107/S2056989020011135

M3 - Article (Academic Journal)

C2 - 32939307

SN - 2056-9890

VL - E76

SP - 1496

EP - 1502

JO - Acta Crystallographica Section E: Crystallographic Communications

JF - Acta Crystallographica Section E: Crystallographic Communications

ER -

Crystal structure and Hirshfeld analysis of 3'-bromo-4-methylchalcone and 3'-cyano-4- methylchalcone

Abstract

Research Groups and Themes

Keywords

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