Structure of 6-acetoxycoumarin: topochemical photodimerization and analysis of acetoxy.acetoxy interactions in the solid state

Murthy, G. S.; Ramamurthy, V.; Venkatesan, Κ.

doi:10.1107/s0108270187006905

Cited by 8 publications

(5 citation statements)

References 10 publications

(12 reference statements)

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“…Structural details of several related aminocoumarin laser-dye compounds have been reported (Selladurai & Subramanian, 1992;Chirmakali, Sivakumar & Natarajan, 1989, 1990Chinnakali, Sivakumar, Natarajan & Mathews, 1992;Chinnakali, Selladurai, Sivakumar, Subramanian & Natarajan, 1990;Masilamani, Chandrasekar, Sivaram, Sivasankar & Natarajan, 1986;Messager & Delugeard, 1974;Murthy, Ramamurthy & Venkatesan, 1988).…”

Section: Commentmentioning

confidence: 99%

7-Amino-4-methylcoumarin

Jasinski¹,

Woudenberg²

1994

Acta Crystallogr C

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Section: Commentmentioning

confidence: 99%

7-Amino-4-methylcoumarin

Jasinski¹,

Woudenberg²

1994

Acta Crystallogr C

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“…A search of the Cambridge Structural Database (CSD, version 5.43; update 3, September 2022; Groom et al, 2016) for structures having a coumarin motif similar to that of I returned five hits for to the following molecules: 4-methyl-2-oxo-2H-1benzopyran-6-yl pyridine-2-carboxylate (CSD refcode ATOROT; Ji et al, 2016), 4-methyl-2-oxo-2H-1-benzopyran-6yl pyridine-3-carboxylate (ATORUZ; Ji et al, 2016), 4-methyl-2-oxo-2H-1-benzopyran-6-yl pyridine-4-carboxylate (ATOSAG; Ji et al, 2016), 6-acetoxycoumarin (GASXON; Murthy et al, 1988) and 4-methyl-2-oxo-2H-chromen-6-yl benzoate (YEFSOU; Ji et al, 2017). ATORUZ only features a C6-H6� � �O3 hydrogen bond because a methyl group is bonded to C9 (according to the numbering scheme of I).…”

Section: Database Surveymentioning

confidence: 99%

Synthesis, structure and Hirshfeld surface analysis of 2-oxo-2H-chromen-6-yl 4-tert-butylbenzoate: work carried out as part of the AFRAMED project

Kenfack Tsobnang,

Ziki,

Siaka

et al. 2024

Acta Crystallogr E Cryst Commun

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In the title compound, C20H18O4, the dihedral angle between the 2H-chromen-2-one ring system and the phenyl ring is 89.12 (5)°. In the crystal, the molecules are connected through C—H...O hydrogen bonds to generate [010] double chains that are reinforced by weak aromatic π–π stacking interactions. The unit-cell packing can be described as a tilted herringbone motif. The H...H, H...O/O...H, H...C/C...H and C...C contacts contribute 46.7, 24.2, 16.7 and 7.6%, respectively, to its Hirshfeld surface.

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“…This kind of reaction have been studied by different research group in similar compound as the cinnamic acid derivates. 16 In this reaction kinds, the spatial disposition (parallel) of the molecules and the distance between them, is fundamental for the dimerization phenomenon. 17 The scheme 2 shows the dimerization reaction.…”

Section: X-ray Diffractionmentioning

confidence: 99%

Structural Study of a New 1-(2-Thienyl)-3-(3-Methyl-2-Thienyl)-Propenone, in Situ Radiation-Induced Dimerization Products

Moreno

Contreras

Buljan

et al. 2010

J. Chil. Chem. Soc.

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The new conjugated system ("chalcone kind") reported herein, 1-(2-thienyl)-3-(3-methyl-2-thienyl)-propenone, C 12 H 10 OS 2 presents a monomeric molecular structure, and it most interesting aspects are to be found in it intermolecular interactions, of varied type (C-H···O, C-H···π, π···π) and strength. Some anomalies detected in the refinement process, however, provided evidence that an unexpected in-situ, radiation-induced dimerization reaction had taken place during data collection, with the starting and final products coexisting in a topotactic fashion. This effect is depended of structural packing; that is not all this kind of conjugated system presents this effect. The main factor is the distance between the double bonds of neighboring monomers (about 3 Å)

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Structure of 6-acetoxycoumarin: topochemical photodimerization and analysis of acetoxy.acetoxy interactions in the solid state

Cited by 8 publications

References 10 publications

7-Amino-4-methylcoumarin

7-Amino-4-methylcoumarin

Synthesis, structure and Hirshfeld surface analysis of 2-oxo-2H-chromen-6-yl 4-tert-butylbenzoate: work carried out as part of the AFRAMED project

Structural Study of a New 1-(2-Thienyl)-3-(3-Methyl-2-Thienyl)-Propenone, in Situ Radiation-Induced Dimerization Products

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