2,2′-[(4-Ethoxyphenyl)methylene]bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one)

Sureshbabu, N.; Sughanya, V.

doi:10.1107/s1600536812033934

Cited by 4 publications

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“…It is of interest to note that several arylmethylene bis(3-hydroxy-5,5-dimethylcyclohex-2en-1-one) derivatives have been crystallographically analyzed. [13][14][15][16][17][18][19][20] It is known that the crystal packing is predominantly controlled by strong intermolecular hydrogen bonds such as O/N−H • • • O/N due to the presence of strong donor and acceptor atoms. 21,22 Moreover, the weak intermolecular interactions such as C−H • • • O/N, 23,24 C−H • • • halogens, 25,26 C−H • • • π 27 and π • • • π 28 interactions can also interplay a crucial role in controlling the crystal packing in the absence of strong donors and acceptors.…”

Section: Introductionmentioning

confidence: 99%

Quantitative analysis of intermolecular interactions in 2,2’-((4-bromophenyl)methylene)bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one): insights from crystal structure, PIXEL, Hirshfeld surfaces and QTAIM analysis

et al. 2018

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The crystallographic study of 2,2'-((4-bromophenyl)methylene)bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1one) reveals that the compound crystallizes in the centrosymmetric space group P2 1 /c. In the solid state, the structure of the title compound exhibits two strong intramolecular O−H • • • O hydrogen bonding interactions. Further, molecules of the title compound are self-assembled by weak intermolecular C−H • • • O, π • • • π and H • • • H and C−H • • • Br contacts. Various intermolecular interaction that exist in the crystal structure and their energetics are quantified using PIXEL, DFT and QTAIM analyses. Six different motifs are identified from the PIXEL calculation. Lattice energy calculation suggests that the dispersion energy has the highest contribution for the crystal formation. The relative contributions of various intermolecular contacts in the title compound and its closely related analogs are evaluated using Hirshfeld surface analysis and the decomposed fingerprint plots. The common packing features exist between the title compound and its related analogs are identified. The quantitative molecular electrostatic potential surface diagram depicts the potential binding sites which are in good agreement with the crystal structure of the title compound. The structures of title compound in gas and solvent phases are compared with the experimental structure and reveals that they are superimposed very well. The vibrational modes of the monomer and four most stabilized dimers are characterized using both the experimental and DFT calculations. The UV-Vis spectrum is calculated using time dependent-DFT (TD-DFT) method and compared with experimental spectrum. The results indicate that the calculated energy of absorbance and oscillator strength correlate well with the experimental data.

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Section: Introductionmentioning

confidence: 99%

Quantitative analysis of intermolecular interactions in 2,2’-((4-bromophenyl)methylene)bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one): insights from crystal structure, PIXEL, Hirshfeld surfaces and QTAIM analysis

et al. 2018

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Investigation of 9-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)-3,3-dimethyl-2,3,4,9-tetrahydro-1H-xanthen-1-one: Crystal structure, AIM and NBO analysis

Udayakumar

Kothandapani

Ganesan

et al. 2017

Journal of Molecular Structure

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2,2′-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one)

Sughanya¹,

Sureshbabu²

2012

Acta Cryst E

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In the title compound, C24H29BrO6, the dihedral angle between the cyclohexenone mean planes is 57.63 (2)° while the dihedral angles between the benzene ring and the cyclohexenone mean planes are 58.42 (2) and 69.08 (3)°. The two cyclohexenone rings both show an envelope conformation, with the C atom bearing two methyl groups as the flap atom in each ring. Two intramolecular O—H⋯O hydrogen bonds occur. In the crystal, molecules are linked via pairs of O—H⋯O hydrogen bonds, forming inversion dimers.

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2,2′-[(4-Ethoxyphenyl)methylene]bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one)

Abstract: In the title compound, C25H32O5, the two cyclohexenone rings have envelope conformations with the C atom bearing two methyl groups as the flap atom in each ring. Relatively strong intramolecular O—H⋯O hydrogen bonds are observed.

Cited by 4 publications

References 11 publications

Quantitative analysis of intermolecular interactions in 2,2’-((4-bromophenyl)methylene)bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one): insights from crystal structure, PIXEL, Hirshfeld surfaces and QTAIM analysis

Quantitative analysis of intermolecular interactions in 2,2’-((4-bromophenyl)methylene)bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one): insights from crystal structure, PIXEL, Hirshfeld surfaces and QTAIM analysis

Investigation of 9-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)-3,3-dimethyl-2,3,4,9-tetrahydro-1H-xanthen-1-one: Crystal structure, AIM and NBO analysis

2,2′-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one)

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2,2′-[(4-Ethoxyphenyl)methylene]bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one)

Abstract: In the title compound, C25H32O5, the two cyclo­hexenone rings have envelope conformations with the C atom bearing two methyl groups as the flap atom in each ring. Relatively strong intra­molecular O—H⋯O hydrogen bonds are observed.

Cited by 4 publications

References 11 publications

Quantitative analysis of intermolecular interactions in 2,2’-((4-bromophenyl)methylene)bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one): insights from crystal structure, PIXEL, Hirshfeld surfaces and QTAIM analysis

Quantitative analysis of intermolecular interactions in 2,2’-((4-bromophenyl)methylene)bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one): insights from crystal structure, PIXEL, Hirshfeld surfaces and QTAIM analysis

Investigation of 9-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)-3,3-dimethyl-2,3,4,9-tetrahydro-1H-xanthen-1-one: Crystal structure, AIM and NBO analysis

2,2′-[(3-Bromo-4-hydroxy-5-methoxyphenyl)methylidene]bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one)

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Abstract: In the title compound, C25H32O5, the two cyclohexenone rings have envelope conformations with the C atom bearing two methyl groups as the flap atom in each ring. Relatively strong intramolecular O—H⋯O hydrogen bonds are observed.