9-(4-Hydroxy-3,5-dimethoxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1<i>H</i>-xanthene-1,8(2<i>H</i>)-dione

Sughanya, V.; Sureshbabu, N.

doi:10.1107/s1600536812010410

Cited by 6 publications

(2 citation statements)

References 10 publications

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“…The reaction mixture was allowed to cool to 298-301 K and the resulting intermediate compound, 2,2 0 -[(3-bromo-4-hydroxy-5-methoxyphenyl)methylene]bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one) was filtered and dried (m.p. 491 K, 3.4 mmol, yield: 85%) (Sughanya & Sureshbabu, 2012b). In the second stage, about 0.50 g (1.04 mmol) of this intermediate were dissolved in 20 ml of ethanol.…”

Section: Synthesis and Crystallizationmentioning

confidence: 99%

Crystal structure, Hirshfeld surface and frontier molecular orbital analysis of 9-(3-bromo-4-hydroxy-5-methoxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione

Babu¹,

Sughanya²,

Praveenkumar³

et al. 2021

Acta Cryst E

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In the fused ring system of the title compound, C24H27BrO5, the mean plane and maximum deviations of the central pyran ring are 0.0384 (2) and 0.0733 (2) Å, respectively. The cyclohexenone rings both adopt envelope conformations with the tetra-substituted C atoms as flap atoms, whereas the central pyran ring adopts a flattened boat conformation. The central pyran and phenyl substituent rings are almost perpendicular to each other, making a dihedral angle of 89.71 (2)°. In the crystal, pairs of molecules are linked via O—H...O hydrogen bonds, forming inversion dimers with an R 2 2(20) ring motif. A Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H...H (50.6%), O...H/H...O (22.9%) and C...H/H...C (11.1%) contacts. Quantum chemical calculations for the frontier molecular orbitals were undertaken to determine the chemical reactivity of the title compound.

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Section: Synthesis and Crystallizationmentioning

confidence: 99%

Crystal structure, Hirshfeld surface and frontier molecular orbital analysis of 9-(3-bromo-4-hydroxy-5-methoxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione

Babu¹,

Sughanya²,

Praveenkumar³

et al. 2021

Acta Cryst E

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“…For their pharmaceutical properties, see: Dimmock et al (1988); Lambert et al (1997); Poupelin et al (1978); Hideo (1981); Selvanayagam et al (1996). For bond-length data, see: Allen et al (1987) Mehdi et al (2011);Sughanya & Sureshbabu (2012). For ring conformation analysis, see : Cremer & Pople (1975).…”

Section: Related Literaturementioning

confidence: 99%

9-(2,4-Dinitrophenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione

Sureshbabu

Sughanya

2013

Acta Cryst E

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Key indicators: single-crystal X-ray study; T = 296 K; mean (C-C) = 0.002 Å; R factor = 0.052; wR factor = 0.159; data-to-parameter ratio = 25.4.In the title compound, C 23 H 24 N 2 O 7 , the central 4H-pyran ring adopts a flattened boat conformation, whereas both cyclohexenone rings adopt envelope conformations, the C atom bearing the dimethyl substituent being the flap atom in each case. The mean and maximum deviation of the pyran ring are 0.0379 (4) and 0.0605 (3) Å . The mean plane of the pyran ring and the dinitrobenzene ring make a dihedral angle of 85.88 (2) . Related literature

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Camphor sulfonic acid catalyzed one-pot pseudo three-component synthesis of a series of 1,8-dioxo-octahydroxanthenes and comparative crystal structures investigations and Hirshfeld surface analysis of five such derivatives

Banerjee¹,

Kaur²,

Sharma³

et al. 2023

Res Chem Intermed

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9-(4-Hydroxy-3,5-dimethoxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione

Cited by 6 publications

References 10 publications

Crystal structure, Hirshfeld surface and frontier molecular orbital analysis of 9-(3-bromo-4-hydroxy-5-methoxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione

Crystal structure, Hirshfeld surface and frontier molecular orbital analysis of 9-(3-bromo-4-hydroxy-5-methoxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione

9-(2,4-Dinitrophenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione

Camphor sulfonic acid catalyzed one-pot pseudo three-component synthesis of a series of 1,8-dioxo-octahydroxanthenes and comparative crystal structures investigations and Hirshfeld surface analysis of five such derivatives

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