Crystal structure and Hirshfeld surface analysis of (<i>E</i>)-3-(3-iodophenyl)-1-(4-iodophenyl)prop-2-en-1-one

Spruce, Kieran J; Hall, Charlie L.; Potticary, Jason; Pridmore, Natalie E.; Cremeens, Matthew E.; D’Ambruoso, Gemma D.; Matsumoto, Masaomi; Warren, Gabrielle I.; Warren, Stephen D.; Hall, Simon R.

doi:10.1107/s2056989019016402

Cited by 3 publications

(3 citation statements)

References 13 publications

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“…In both instances, no candidates were found to possess the chalcone motif. A previous study on a diiodochalcone (Ep5m) found an alternating IÁ Á ÁI XB channel motif (Spruce et al, 2020); however, these alternate between bond lengths of 3.981 and 4.940 Å , the latter is greater than the sum of the van der Waals radii and so is not classed as an XB (Desiraju et al, 2013). Despite the high prevalence of IÁ Á ÁI XB and iodine-functionalized chalcones, there were no previous examples of an iodine channel XB motif or of a linear IÁ Á ÁO 2 N donor-acceptor XB motif present in a small chalcone molecule.…”

Section: Database Searchesmentioning

confidence: 93%

Structural effects of halogen bonding in iodochalcones

Hamilton

Harris

Hall

et al. 2021

Acta Crystallogr Sect B

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The structures of three iodochalcones, functionalized with fluorine or a nitro group, have been investigated to explore the impact of different molecular electrostatic distributions on the halogen bonding within each crystal structure. The strongly withdrawing nitro group presented a switch of the halogen bond from a lateral to a linear motif. Surprisingly, this appears to be influenced by a net positive shift in charge distribution around the lateral edges of the σ-hole, making the lateral I...I bonding motif less preferable. A channel of amphoteric I...I type II halogen bonds is observed for a chalcone molecule, which was not previously reported in chalcones, alongside an example of the common synthon involving extended linear chains of I...O2N donor–acceptor halogen bonds. This work shows that halogenated chalcones may be an interesting target for developing halogen bonding as a significant tool within crystal engineering, a thus far underexplored area for this common structural motif.

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Section: Database Searchesmentioning

confidence: 93%

Structural effects of halogen bonding in iodochalcones

Hamilton

Harris

Hall

et al. 2021

Acta Crystallogr Sect B

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“…Four related compounds were found as a result of a search for the '(2E)-1,3-diphenylprop-2-en-1-one' unit in the Cambridge Structural Database (CSD, Version 5.42, update of September 2021; Groom et al, 2016), viz. CSD refcodes KOCZUA (Bindya et al, 2019), RUCKIM (Spruce et al, 2020)…”

Section: Database Surveymentioning

confidence: 99%

Crystal structure and Hirshfeld surface analysis of (2E)-1-(4-bromophenyl)-3-(2-methylphenyl)prop-2-en-1-one

Akkurt,

Naghiyev,

Khrustalev

et al. 2023

Acta Cryst E

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In the title compound, C16H13BrO, the planes of the aromatic rings are inclined at an angle of 23.49 (15)°, and the configuration about the C=C bond is E. In the crystal, the molecules are linked into chains by weak C—H...O interactions along the b axis. Successive chains form a zigzag structure along the c axis, and these chains are connected to each other by face-to-face π–π stacking interactions along the a axis. These layers, parallel to the (001) plane, are linked by van der Waals interactions, thus consolidating the crystal structure. Hirshfeld surface analysis showed that the most significant contacts in the structure are H...H (43.1%), C...H/H...C (17.4%), Br...H/H...Br (14.9%), C...C (11.9%) and O...H/H...O (9.8%).

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“…The relative ease of synthesis, the ability to modify the aromatic ring substituents, and the biological activity of some chalcone molecules has sparked interest in their use as a starting point for future pharmaceuticals (Gomes et al, 2017;Zhuang et al, 2017). The straightforward synthesis combined with the ability to modify the ring substituents also makes chalcones an ideal system to study the effects of ring substitution on crystal packing (Battaglia et al, 2020;Hall et al, 2020a,b;Hamilton et al, 2021;Spruce et al, 2020). This article compares the molecular orientation and packing of two newly crystallized chalcone molecules.…”

Section: Introductionmentioning

confidence: 99%

Crystal structures, Hirshfeld analysis, and energy framework analysis of two differently 3′-substituted 4-methylchalcones: 3′-(N=CHC₆H₄-p-CH₃)-4-methylchalcone and 3′-(NHCOCH₃)-4-methylchalcone

Battaglia¹,

Kersten²,

Nicol³

et al. 2023

Acta Crystallogr C

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Two crystal structures of chalcones, or 1,3-diarylprop-2-en-1-ones, are presented; both contain a p-methyl substitution on the 3-Ring, but differ with respect to the m-substitution on the 1-Ring. Their systematic names are (2E)-3-(4-methylphenyl)-1-(3-{[(4-methylphenyl)methylidene]amino}phenyl)prop-2-en-1-one (C24H21NO) and N-{3-[(2E)-3-(4-methylphenyl)prop-2-enoyl]phenyl}acetamide (C18H17NO2), which are abbreviated as 3′-(N=CHC6H4-p-CH3)-4-methylchalcone and 3′-(NHCOCH3)-4-methylchalcone, respectively. Both chalcones represent the first reported acetamide-substituted and imino-substituted chalcone crystal structures, adding to the robust library of chalcone structures within the Cambridge Structural Database. The crystal structure of 3′-(N=CHC6H4-p-CH3)-4-methylchalcone exhibits close contacts between the enone O atom and the substituent arene ring, in addition to C...C interactions between the substituent arene rings. The structure of 3′-(NHCOCH3)-4-methylchalcone exhibits a unique interaction between the enone O atom and the 1-Ring substituent, contributing to its antiparallel crystal packing. In addition, both structures exhibit π-stacking, which occurs between the 1-Ring and R-Ring for 3′-(N=CHC6H4-p-CH3)-4-methylchalcone, and between the 1-Ring and 3-Ring for 3′-(NHCOCH3)-4-methylchalcone.

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Crystal structure and Hirshfeld surface analysis of (E)-3-(3-iodophenyl)-1-(4-iodophenyl)prop-2-en-1-one

Cited by 3 publications

References 13 publications

Structural effects of halogen bonding in iodochalcones

Structural effects of halogen bonding in iodochalcones

Crystal structure and Hirshfeld surface analysis of (2E)-1-(4-bromophenyl)-3-(2-methylphenyl)prop-2-en-1-one

Crystal structures, Hirshfeld analysis, and energy framework analysis of two differently 3′-substituted 4-methylchalcones: 3′-(N=CHC₆H₄-p-CH₃)-4-methylchalcone and 3′-(NHCOCH₃)-4-methylchalcone

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Crystal structure and Hirshfeld surface analysis of (E)-3-(3-iodophenyl)-1-(4-iodophenyl)prop-2-en-1-one

Cited by 3 publications

References 13 publications

Structural effects of halogen bonding in iodochalcones

Structural effects of halogen bonding in iodochalcones

Crystal structure and Hirshfeld surface analysis of (2E)-1-(4-bromophenyl)-3-(2-methylphenyl)prop-2-en-1-one

Crystal structures, Hirshfeld analysis, and energy framework analysis of two differently 3′-substituted 4-methylchalcones: 3′-(N=CHC6H4-p-CH3)-4-methylchalcone and 3′-(NHCOCH3)-4-methylchalcone

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Crystal structures, Hirshfeld analysis, and energy framework analysis of two differently 3′-substituted 4-methylchalcones: 3′-(N=CHC₆H₄-p-CH₃)-4-methylchalcone and 3′-(NHCOCH₃)-4-methylchalcone