Coumarin 314

Yip, B. C.; Fun, H. K.; Sivakumar, K.; Zhou, Z. Y.; Shawkataly, Omar bin; Teoh, S. G.

doi:10.1107/s010827019401317x

Cited by 8 publications

(12 citation statements)

References 1 publication

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“…2) shows that the molecules are stacked in layers .parallel to (103), with an interlayer spacing of 3.428 A. This distance is shorter than that observed in the packing of the rigidized aminocoumarins, which are normally stacked with an interlayer distance of ca 3.6 ,~, (Yip et al, 1994). …”

Section: Commentmentioning

confidence: 91%

Coumarin 311

Yip¹,

YAW²,

Ong³

et al. 1995

Acta Crystallogr C

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Section: Commentmentioning

confidence: 91%

Coumarin 311

Yip¹,

YAW²,

Ong³

et al. 1995

Acta Crystallogr C

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“…The ORTEP diagram along with the atom labeling of the molecules in the respective forms are displayed in Figure 1. The detailed discussion on geometrical analyses of the yellow 10 and the orange 11 forms based on X-ray diffraction data collected at room temperature are already reported in the literature. Although the report on the yellow form points out the higher thermal parameters of atom O20, no disorder was considered for this atom.…”

Section: Resultsmentioning

confidence: 99%

“…The title compound was purchased as fine powder from Aldrich. The crystallization of coumarin 314 from a mixture of chloroform and ethanol, as described by Yip et al, 10 resulted in several yellow-colored crystals with "block" type morphology. The cell-checking experiments on these yellow crystals revealed that these are of the original known form, the yellow form.…”

Section: Experimental and Theoretical Sectionmentioning

confidence: 99%

“…The cell-checking experiments on these yellow crystals revealed that these are of the original known form, the yellow form. 10 Several attempts were made with the coumarin 314 from Aldrich to grow the crystals of the known orange form in ethanol solution as reported earlier, 11 but every time very small or flat crystals of the yellow form appeared. Similar crystals were found even with different solvents such as acetone, ethyl acetate, ether, etc.…”

Section: Experimental and Theoretical Sectionmentioning

confidence: 99%

“…A wide variety of pharmacological activities, such as antiviral 4 and antimicrobial activity, 5 are exhibited by coumarin derivatives, and they form the basic building block in the well-known antibiotic novobiocin. 6 Coumarin dyes such as coumarin 138, 7 coumarin 152, 8 coumarin 153, 9 and coumarin 314 10,11 are found to exist in two different crystalline forms. The phenomenon, existence of a crystal structure in more than one crystalline form, is known as polymorphism.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Experimental and Theoretical Charge Density Analysis of Polymorphic Structures: The Case of Coumarin 314 Dye

Munshi

Jelsch

Hathwar

et al. 2010

Crystal Growth & Design

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Experimental charge density distributions in two known conformational polymorphs (orange and yellow) of coumarin 314 dye are analyzed based on multipole modeling of X-ray diffraction data collected at 100 K. The experimental results are compared with the charge densities derived from multipole modeling of theoretical structure factors obtained from periodic quantum calculation with density functional theory (DFT) method and B3LYP/6-31G(d,p) level of theory. The presence of disorder at the carbonyl oxygen atom of ethoxycarbonyl group in the yellow form, which was not identified earlier, is addressed here. The investigation of intermolecular interactions, based on Hirshfeld surface analysis and topological properties via quantum theory of atoms in molecule and total electrostatic interaction energies, revealed significant differences between the polymorphs. The differences of electrostatic nature in these two polymorphic forms were unveiled via construction of threedimensional deformation electrostatic potential maps plotted over the molecular surfaces. The lattice energies evaluated from ab initio calculations on the two polymorphic forms indicate that the yellow form is likely to be the most favorable thermodynamically. The dipole moments derived from experimental and theoretical charge densities and also from Lorentz tensor approach are compared with the single-molecule dipole moments. In each case, the differences of dipole moments between the polymorphs are identified.

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Determining the Three‐Dimensional Electronic Transition Dipole Moment Orientation: Influence of an Isomeric Mixture

et al. 2010

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A new mixed experimental and theoretical approach for determining the exact three-dimensional orientation of electronic transition dipole moments (tdms) within the molecular frame is discussed. Results of applying this method on Chlorophyll a and the dye Coumarin 314 (C314) are presented. For C314 the possible influence of a mixture of E- and Z-isomers in the sample on the determined electronic tdm is investigated. Moreover, the robustness of the method is investigated with the C314 data.

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Coumarin 314

Cited by 8 publications

References 1 publication

Coumarin 311

Coumarin 311

Experimental and Theoretical Charge Density Analysis of Polymorphic Structures: The Case of Coumarin 314 Dye

Determining the Three‐Dimensional Electronic Transition Dipole Moment Orientation: Influence of an Isomeric Mixture

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