Crystal structures of three functionalized chalcones: 4'-di-methyl-amino-3-nitro-chalcone, 3-di-methyl-amino-3'-nitrochalcone and 3'-nitro-chalcone

Charlie L Hall; Victoria Hamilton; Jason Potticary; Matthew E Cremeens; Natalie E Pridmore; Hazel A Sparkes; Gemma D D'ambruoso; Stephen D Warren; Masaomi Matsumoto; Simon R Hall

doi:10.1107/s2056989020011858

Crystal structures of three functionalized chalcones: 4'-di-methyl-amino-3-nitro-chalcone, 3-di-methyl-amino-3'-nitrochalcone and 3'-nitro-chalcone

Charlie L Hall, Victoria Hamilton, Jason Potticary, Matthew E Cremeens, Natalie E Pridmore, Hazel A Sparkes, Gemma D D'ambruoso, Stephen D Warren, Masaomi Matsumoto, Simon R Hall

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Abstract

The structure of three functionalized chalcones (1,3-di-aryl-prop-2-en-1-ones), containing combinations of nitro and di-methyl-amino functional groups, are presented, namely, 1-[4-(di-methyl-amino)-phen-yl]-3-(3-nitro-phen-yl)prop-2-en-1-one, C17H16N2O3, Gp8m, 3-[3-(di-methyl-amino)-phen-yl]-1-(3-nitro-phen-yl)prop-2-en-1-one, C17H16N2O3, Hm7m and 1-(3-nitro-phen-yl)-3-phenyl-prop-2-en-1-one, C15H11NO3, Hm1-. Each of the mol-ecules contains bonding motifs seen in previously solved crystal structures of functionalized chalcones, adding to the large dataset available for these small organic mol-ecules. The structures of all three of the title compounds contain similar bonding motifs, resulting in two-dimensional planes of mol-ecules formed via C-H⋯O hydrogen-bonding inter-actions involving the nitro- and ketone groups. The structure of Hm1- is very similar to the crystal structure of a previously solved isomer [Jing (2009 ▸). Acta Cryst. E65, o2510].

Original language	English
Pages (from-to)	1599-1604
Number of pages	6
Journal	Acta Crystallographica Section E: Crystallographic Communications
Volume	E76
DOIs	https://doi.org/10.1107/s2056989020011858
Publication status	Published - 1 Oct 2020

Keywords

chalcone
dimethylamino
nitro
crystal structure

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Hall, C. L., Hamilton, V., Potticary, J., Cremeens, M. E., Pridmore, N. E., Sparkes, H. A., D'ambruoso, G. D., Warren, S. D., Matsumoto, M., & Hall, S. R. (2020). Crystal structures of three functionalized chalcones: 4'-di-methyl-amino-3-nitro-chalcone, 3-di-methyl-amino-3'-nitrochalcone and 3'-nitro-chalcone. Acta Crystallographica Section E: Crystallographic Communications, E76, 1599-1604. https://doi.org/10.1107/s2056989020011858

@article{e2c2e3bdc36b4778a66736fa085adca2,

title = "Crystal structures of three functionalized chalcones: 4'-di-methyl-amino-3-nitro-chalcone, 3-di-methyl-amino-3'-nitrochalcone and 3'-nitro-chalcone",

abstract = "The structure of three functionalized chalcones (1,3-di-aryl-prop-2-en-1-ones), containing combinations of nitro and di-methyl-amino functional groups, are presented, namely, 1-[4-(di-methyl-amino)-phen-yl]-3-(3-nitro-phen-yl)prop-2-en-1-one, C17H16N2O3, Gp8m, 3-[3-(di-methyl-amino)-phen-yl]-1-(3-nitro-phen-yl)prop-2-en-1-one, C17H16N2O3, Hm7m and 1-(3-nitro-phen-yl)-3-phenyl-prop-2-en-1-one, C15H11NO3, Hm1-. Each of the mol-ecules contains bonding motifs seen in previously solved crystal structures of functionalized chalcones, adding to the large dataset available for these small organic mol-ecules. The structures of all three of the title compounds contain similar bonding motifs, resulting in two-dimensional planes of mol-ecules formed via C-H⋯O hydrogen-bonding inter-actions involving the nitro- and ketone groups. The structure of Hm1- is very similar to the crystal structure of a previously solved isomer [Jing (2009 ▸). Acta Cryst. E65, o2510].",

keywords = "chalcone, dimethylamino, nitro, crystal structure",

author = "Hall, {Charlie L} and Victoria Hamilton and Jason Potticary and Cremeens, {Matthew E} and Pridmore, {Natalie E} and Sparkes, {Hazel A} and D'ambruoso, {Gemma D} and Warren, {Stephen D} and Masaomi Matsumoto and Hall, {Simon R}",

note = "{\textcopyright} Hall et al. 2020.",

year = "2020",

month = oct,

day = "1",

doi = "10.1107/s2056989020011858",

language = "English",

volume = "E76",

pages = "1599--1604",

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

issn = "2056-9890",

publisher = "John Wiley & Sons, Ltd.",

}

Hall, CL, Hamilton, V, Potticary, J, Cremeens, ME, Pridmore, NE, Sparkes, HA, D'ambruoso, GD, Warren, SD, Matsumoto, M & Hall, SR 2020, 'Crystal structures of three functionalized chalcones: 4'-di-methyl-amino-3-nitro-chalcone, 3-di-methyl-amino-3'-nitrochalcone and 3'-nitro-chalcone', Acta Crystallographica Section E: Crystallographic Communications, vol. E76, pp. 1599-1604. https://doi.org/10.1107/s2056989020011858

Crystal structures of three functionalized chalcones: 4'-di-methyl-amino-3-nitro-chalcone, 3-di-methyl-amino-3'-nitrochalcone and 3'-nitro-chalcone. / Hall, Charlie L; Hamilton, Victoria; Potticary, Jason et al.
In: Acta Crystallographica Section E: Crystallographic Communications, Vol. E76, 01.10.2020, p. 1599-1604.

Research output: Contribution to journal › Article (Academic Journal) › peer-review

TY - JOUR

T1 - Crystal structures of three functionalized chalcones

T2 - 4'-di-methyl-amino-3-nitro-chalcone, 3-di-methyl-amino-3'-nitrochalcone and 3'-nitro-chalcone

AU - Hall, Charlie L

AU - Hamilton, Victoria

AU - Potticary, Jason

AU - Cremeens, Matthew E

AU - Pridmore, Natalie E

AU - Sparkes, Hazel A

AU - D'ambruoso, Gemma D

AU - Warren, Stephen D

AU - Matsumoto, Masaomi

AU - Hall, Simon R

PY - 2020/10/1

Y1 - 2020/10/1

N2 - The structure of three functionalized chalcones (1,3-di-aryl-prop-2-en-1-ones), containing combinations of nitro and di-methyl-amino functional groups, are presented, namely, 1-[4-(di-methyl-amino)-phen-yl]-3-(3-nitro-phen-yl)prop-2-en-1-one, C17H16N2O3, Gp8m, 3-[3-(di-methyl-amino)-phen-yl]-1-(3-nitro-phen-yl)prop-2-en-1-one, C17H16N2O3, Hm7m and 1-(3-nitro-phen-yl)-3-phenyl-prop-2-en-1-one, C15H11NO3, Hm1-. Each of the mol-ecules contains bonding motifs seen in previously solved crystal structures of functionalized chalcones, adding to the large dataset available for these small organic mol-ecules. The structures of all three of the title compounds contain similar bonding motifs, resulting in two-dimensional planes of mol-ecules formed via C-H⋯O hydrogen-bonding inter-actions involving the nitro- and ketone groups. The structure of Hm1- is very similar to the crystal structure of a previously solved isomer [Jing (2009 ▸). Acta Cryst. E65, o2510].

AB - The structure of three functionalized chalcones (1,3-di-aryl-prop-2-en-1-ones), containing combinations of nitro and di-methyl-amino functional groups, are presented, namely, 1-[4-(di-methyl-amino)-phen-yl]-3-(3-nitro-phen-yl)prop-2-en-1-one, C17H16N2O3, Gp8m, 3-[3-(di-methyl-amino)-phen-yl]-1-(3-nitro-phen-yl)prop-2-en-1-one, C17H16N2O3, Hm7m and 1-(3-nitro-phen-yl)-3-phenyl-prop-2-en-1-one, C15H11NO3, Hm1-. Each of the mol-ecules contains bonding motifs seen in previously solved crystal structures of functionalized chalcones, adding to the large dataset available for these small organic mol-ecules. The structures of all three of the title compounds contain similar bonding motifs, resulting in two-dimensional planes of mol-ecules formed via C-H⋯O hydrogen-bonding inter-actions involving the nitro- and ketone groups. The structure of Hm1- is very similar to the crystal structure of a previously solved isomer [Jing (2009 ▸). Acta Cryst. E65, o2510].

KW - chalcone

KW - dimethylamino

KW - nitro

KW - crystal structure

U2 - 10.1107/s2056989020011858

DO - 10.1107/s2056989020011858

M3 - Article (Academic Journal)

C2 - 33117572

SN - 2056-9890

VL - E76

SP - 1599

EP - 1604

JO - Acta Crystallographica Section E: Crystallographic Communications

JF - Acta Crystallographica Section E: Crystallographic Communications

ER -

Crystal structures of three functionalized chalcones: 4'-di-methyl-amino-3-nitro-chalcone, 3-di-methyl-amino-3'-nitrochalcone and 3'-nitro-chalcone

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Keywords

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