Structure of 2-(2,6-dimethoxyphenyl)-7-hydroxy-4H-1-benzopyran-4-one (7-hydroxy-2',6'-dimethoxyflavone)

Wallet, Jean‐Claude; Gaydou, E. M.; Espinosa, Enrique; Osorno, Oscar; Molins, E.; Miravitlles, C.

doi:10.1107/s0108270191006285

Cited by 6 publications

(4 citation statements)

References 5 publications

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“…The former values are comparable to those of 62.2(1) ° in 6-hydroxy-2',3'-dimethoxyflavone (Wallet, Gaydou, Mas, Molins & Miravitlles, 1993) and 68.2 ° in 7-hydroxy-U,6 ~dimethoxyflavone (Wallet, Gaydou, Espinosa, Osorno, Molins & Miravitlles, 1992). The dihydroxyphenyl [dimethoxyphenyl for (II)] and 3-methyl-2-butenyl groups are not coplanar with the benzopyranone in either molecule; the torsion angles C3---C2---C1'--C2 ~ and C4---C3--C11--C12 are 67.9(4) and 74.3(4), and 85.5(2) and 96.4 (2) ° in (I) and (II), respectively.…”

Section: O• O [~Och3supporting

confidence: 72%

Morusin and Morusin Dimethyl Ether

Uchida¹,

Mizutani²,

Ohshima³

et al. 1996

Acta Crystallogr C

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Section: O• O [~Och3supporting

confidence: 72%

Morusin and Morusin Dimethyl Ether

Uchida¹,

Mizutani²,

Ohshima³

et al. 1996

Acta Crystallogr C

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“…1992; Wallet et al 1992Wallet et al , 1993. The lengthening of the double bond C4=O4 [1⋅252(2) Å] is due to strong intra- Table 3.…”

Section: Compound IImentioning

confidence: 99%

X-ray study of weak interactions in two flavonoids

et al. 2007

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X-ray diffraction studies were carried out on single crystals of two flavonoids, viz. 5-hydroxy-6,7,4′-trimethoxyflavone, C 18 H 16 O 6 , (I) and 5-hydroxy-3,7,4′-trimethoxyflavone, C 18 H 16 O 6 , (II). Crystal structures of both the flavonoids were solved by direct methods and refined by full-matrix least-squares procedures. In both the molecules, the benzopyran moiety is planar. The dihedral angle between the phenyl ring and the benzopyran portion is 5⋅50(4)° in (I) and 29⋅11(5)° in (II). In (I), the crystal packing is influenced by O-H…O hydrogen bonds, and weak C-H…O and π…π interactions whereas in (II) the crystal structure is stabilized by the presence of four intermolecular short contacts of the type C-H…O. There is also one C-H…π hydrogen bond with H… centroid distance of < 2⋅7 Å. The molecules are further stabilized by π-π interactions.

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“…The relative contribution of the different interactions to the Hirshfeld surface was calculated for the title compounds as well as a number of substituted chromones (Fig. 8) available in the CSD (ref-codes GIRWAG, 39 REBHEM 40 for 5, 7-substitution and GODJUF, 41 SIMNAE, 42 TAJSAY, 43 VOKVIA, 44 XAHPUR, 45 YAXDUW 46 for 2,7substitution) which offers some insight into the effect of different substituents on the chromone backbone. With different substituents at the 5,7-and 2,7-position, the contribution of H/H interactions to the Hirshfeld Surface increases steadily up to well over 52% in 2 with a corresponding decrease in the contribution to 35% in GIRWAG.…”

Section: Crystal Structure Descriptionmentioning

confidence: 99%

“…37 Therefore, the chromone moieties in one single molecule give the possibility of achieving novel bioactive compounds. A search of the Cambridge Structural Database (version 5.31, November CSD 2009 release) 38 with both benzopyran ring moiety unsubstituted and different substitution yielded 343 hits (excluding duplicate structure determinations), 335 had different substitutions but only 2 (CSD ref-codes GIRWAG, 39 REBHEM 40 ) of which had 5,7-substitution, with the remaining 6 (CSD ref-codes GODJUF, 41 SIMNAE, 42 TAJSAY, 43 VOK-VIA, 44 XAHPUR, 45 YAXDUW 46 ) containing different substituent groups at the 2,7-positions. A symmetrical substitution at the 5,7-and 2,7-positions is, however, yet to be reported.…”

Section: Introductionmentioning

confidence: 99%