Anita Penkova, Pascal Retailleau, Ilia Manolov, "Crystal Structure of Poly[(acetone-O)-3-((3,4-dimethoxyphenyl)(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl)-(2-oxo-2H-chromen-4-olate)sodium]", Organic Chemistry International, vol. 2010, Article ID 564256, 7 pages, 2010. https://doi.org/10.1155/2010/564256
Crystal Structure of Poly[(acetone-O)-3-((3,4-dimethoxyphenyl)(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl)-(2-oxo-2H-chromen-4-olate)sodium]
Anita Penkova,1,2Pascal Retailleau,3 and Ilia Manolov4
1University of Southern California, Los Angeles, CA 90089-1453, USA
2Rostislaw Kaischew Institute of Physical Chemistry, BAS, Akad. G.Bonchev str., 1113 Sofia, Bulgaria
3Service de Cristallochimie, Institut de Chimie des Substances Naturelles—CNRS, UPR2301 Bât 27 - 1 Avenue de la Terrasse, 91198 Gif-sur-Yvette Cédex, France
4Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Medical University, 2, Dunav St., 1000 Sofia, Bulgaria
Academic Editor: Cyril Parkanyi
Received30 Oct 2009
Revised01 Mar 2010
Accepted20 Apr 2010
Published28 Jun 2010
The structure of Poly[(acetone-O)-3-((3,4-dimethoxyphenyl)(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl)-(2-oxo-2H-chromen-4-olate)sodium] was determined by X-ray crystallography. The compound crystallizes in an orthorhombic system and was characterized thus P , (2) Å, (3) Å, Å. , (10) Å3. The crystal structure was solved by direct methods and refined by full-matrix least-squares on to final values of and .
Biscoumarin derivatives possess anticoagulant, spasmolytic, bacteriostatic, and rodenticidal activities. Some of them can be used as herbicides. By chemical modifications (different substituents on the aromatic ring) it is possible to obtain a compound with good biological activity, but with lower toxicity and fewer side effects.
The title compound was synthesized from 3,3′-[(3,4-dimethoxyphenyl)-methylidene]-bis(4-hydroxy-2H-chromen-2-one) and water solution of sodium hydroxide at a molar ratio. This compound showed an effect on HIV replication in acutely infected cells by microtiter infection assay. The same substance demonstrated no impact on early stages of HIV-1 replication cycle . The transformation of the compound to sodium salt was a stage for synthesizing complex compounds with lanthanides.
We only succeeded in growing colourless thin needles for single-crystal X-ray diffraction analysis by slow evaporation of an ethanol/acetone solution. Crystallographic data collected at room temperature with an Enraf-Nonius KappaCCD diffractometer using graphite monochromated Mo- ( Å) radiation were therefore of limited diffraction quality (Table 1). The solid state structure of the molecule was nonetheless investigated satisfactorily from a chemical/crystallographical point of view.
Crystal system, space group
Orthorhombic, P 21 21 21
Unit cell dimensions
Å, = 90°
Å, = 90°
Å, = 90°
, Calculated density
4, 1.452 g/cm3
range for data collection
2.00 to 22.11°
Completeness to = 22.11
Semi-empirical from equivalents
Max. and min. transmission
0.99 and 0.86
Full-matrix least-squares on
1 = 0.0585, 2 = 0.1449/
indices (all data)
1 = 0.0774, 2 = 0.1556
Largest diff. peak and hole
0.256 and −0.385 e.Å-3
Crystal data and structure refinement for Compound 1.
Crystal unit-cell and orientation parameters were determined by the DENZO  auto indexing procedure, as implemented in the data collection monitoring program COLLECT . Intensities recorded up to a diffraction angle, , of 22.1° were also integrated by DENZO, scaled, and then reduced using SCALEPACK-HKL2000 , after postrefinement of the unit-cell parameters and absorption correction based on symmetry-equivalent and repeated reflections. The structure was solved by direct methods using SIR97 , and all of the nonhydrogen atoms were refined anisotropically by full-matrix least-squares on using SHELXL97 . All hydrogen atoms were located in difference electron-density maps, but refined as riding, with C–H = 0.93, 0.96, 0.97, and 0.98 Å for the aromatic, methyl, and methyne H atoms, respectively, O–H = 0.82 Å for hydroxyl H atoms, and with (H) (C) or 1.5 (methyl C). Crystallographic data and details of the data collection and structure refinements are listed in Table 1. The observed anisotropic thermal parameters, the calculated structure factors, and full lists of the bond distances, bond angles, torsion angles, and intermolecular H-bond interactions are given as supplementary material (Tables 2, 3, 4, 5, 6, 7, and 8). The bond lengths and bond angles are all within the expected ranges.
Atomic coordinates and equivalent isotropic displacement parameters (A2) for Compound 1. U(eq) is defined as one third of the trace of the orthogonalized tensor.