Organic Chemistry International

Organic Chemistry International / 2010 / Article

Research Article | Open Access

Volume 2010 |Article ID 564256 | https://doi.org/10.1155/2010/564256

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]

Academic Editor: Cyril Parkanyi
Received30 Oct 2009
Revised01 Mar 2010
Accepted20 Apr 2010
Published28 Jun 2010

Abstract

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 [1]. 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.


Identification codeCompound 1

Empirical formulaC30H25NaO10
Formula weight552.49
Temperature293(2) K
Wavelength.71069 A
Crystal system, space groupOrthorhombic, P 21 21 21
Unit cell dimensions  Å, = 90°
 Å, = 90°
 Å, = 90°
Volume2535.9(10) Å3
, Calculated density4, 1.452 g/cm3
Absorption coefficient0.124 mm−1
(000)1152
Crystal size  mm3
range for data collection2.00 to 22.11°
Limiting indices ,   , 
Reflections collected/unique14591/1822
Completeness to = 22.1199.6%
Absorption correctionSemi-empirical from equivalents
Max. and min. transmission0.99 and 0.86
Refinement methodFull-matrix least-squares on
Data/restraints/parameters1822/23/365
Goodness-of-fit on 1.146
Final indices 1 = 0.0585, 2 = 0.1449/
indices (all data) 1 = 0.0774, 2 = 0.1556
Extinction coefficient0.008(2)
Largest diff. peak and hole0.256 and −0.385 e.Å-3
CCDC723527

Crystal unit-cell and orientation parameters were determined by the DENZO [1] auto indexing procedure, as implemented in the data collection monitoring program COLLECT [2]. Intensities recorded up to a diffraction angle, , of 22.1° were also integrated by DENZO, scaled, and then reduced using SCALEPACK-HKL2000 [2], 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 [3], and all of the nonhydrogen atoms were refined anisotropically by full-matrix least-squares on using SHELXL97 [4]. 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.


U(eq)

Na1
O2
O3
O5
O7
O4
O1′
O1
O2′
O3′
C10
C13
C12
C11
C2
C16
C15
C14
C8A
C3
C1
C8
C7
C6
C17
C5
C4A
C2′
C4
C18
C19
C3′
C4′
C5′
C6′
C7′
C8′
C4A′
C8A′
C9


Na1–O22.267(7)C16–C151.391(10)
Na1–O2′2.323(7)C16–C1i1.541(11)
Na1–O72.347(9)C15–C141.376(11)
Na1–O52.414(6)C8A–C4A1.384(11)
Na1–O42.481(7)C8A–C81.388(11)
Na1–O3iv2.775(6)C3–C41.377(10)
O2–C21.206(9)C3–C11.521(10)
O3–C41.314(9)C1–C3′1.520(10)
O3–Na1ii2.775(6)C1–C16v1.541(11)
O5–C131.376(9)C8–C71.367(12)
O5–C101.439(10)C7–C61.418(13)
O7–C171.202(15)C6–C51.371(11)
O4–C121.378(9)C17–C191.435(13)
O4–C91.404(9)C17–C181.436(12)
O1′–C8A′1.376(9)C5–C4A1.388(11)
O1′–C2′1.395(9)C4A–C41.455(11)
O1–C8A1.356(9)C2′–C3′1.429(10)
O1–C21.406(9)C3′–C4′1.375(10)
O2′–C2′1.198(9)C4′–C4A′1.471(11)
O3′–C4′1.306(9)C5′–C6′1.394(12)
C13–C141.357(10)C5′–C4A′1.397(11)
C13–C121.407(10)C6′–C7′1.408(13)
C12–C111.385(10)C7′–C8′1.364(12)
C11–C161.379(10)C8′–C8A′1.390(11)
C2–C31.429(11)C4A′–C8A′1.371(11)


O2–Na1–O7174.5(3)O1–C8A–C4A121.7(7)
O2′–Na1–O790.9(3)O1–C8A–C8116.5(8)
O2–Na1–O586.9(2)C4A–C8A–C8121.8(8)
O2′–Na1–O5153.6(3)C4–C3–C2120.7(8)
O7–Na1–O597.2(3)C4–C3–C1124.4(7)
O2–Na1–O4100.4(2)C2–C3–C1114.9(7)
O2′–Na1–O492.7(2)C3′–C1–C3115.0(6)
O7–Na1–O484.8(3)C3′–C1–C16v115.3(6)
O5–Na1–O463.33(19)C3–C1–C16v113.8(6)
O2–Na1–O3iv94.2(2)C7–C8–C8A120.0(9)
O2′–Na1–O3iv100.4(2)C8–C7–C6118.9(8)
O7–Na1–O3iv81.2(3)C5–C6–C7120.2(8)
O5–Na1–O3iv105.6(2)O7–C17–C19113.5(14)
O4–Na1–O3iv160.9(2)O7–C17–C18126.2(15)
C2–O2–Na1152.5(5)C19–C17–C18120.2(15)
C4–O3–Na1ii147.8(5)C6–C5–C4A121.0(8)
C13–O5–C10116.8(7)C8A–C4A–C5118.0(7)
C13–O5–Na1123.0(5)C8A–C4A–C4118.7(7)
C10–O5–Na1117.5(5)C5–C4A–C4123.2(7)
C17–O7–Na1134.9(11)O2′–C2′–O1′113.6(7)
C12–O4–C9118.3(6)O2′–C2′–C3′127.9(7)
C12–O4–Na1120.0(4)O1′–C2′–C3′118.4(7)
C9–O4–Na1121.2(5)O3–C4–C3123.6(7)
C8A′–O1′–C2′121.1(6)O3–C4–C4A117.4(7)
C8A–O1–C2121.4(7)C3–C4–C4A119.0(7)
C2′–O2′–Na1148.4(5)C4′–C3′–C2′120.9(7)
C14–C13–O5126.7(7)C4′–C3′–C1122.3(7)
C14–C13–C12119.0(7)C2′–C3′–C1116.7(7)
O5–C13–C12114.3(7)O3′–C4′–C3′125.7(7)
O4–C12–C11124.5(7)O3′–C4′–C4A′115.7(7)
O4–C12–C13115.6(7)C3′–C4′–C4A′118.6(7)
C11–C12–C13119.8(7)C6′–C5′–C4A′119.7(8)
C16–C11–C12121.3(7)C5′–C6′–C7′118.9(9)
O2–C2–O1113.4(7)C8′–C7′–C6′121.7(9)
O2–C2–C3128.3(8)C7′–C8′–C8A′118.1(9)
O1–C2–C3118.3(8)C8A′–C4A′–C5′119.3(7)
C11–C16–C15117.3(7)C8A′–C4A′–C4′118.8(7)
C11–C16–C1i123.6(6)C5′–C4A′–C4′121.9(7)
C15–C16–C1i118.8(7)C4A′–C8A′–O1′121.7(7)
C14–C15–C16122.0(7)C4A′–C8A′–C8′122.2(8)
C13–C14–C15120.5(7)O1′–C8A′–C8′116.1(7)

Symmetry transformations used to generate equivalent atoms: i: , , ; ii: , , ; iv: , , ; v: , , .

U11U22U33U23U13U12

Na1
O2
O3
O5
O7
O4
O1′
O1
O2′
O3′
C10
C13
C12
C11
C2
C16
C15
C14
C8A
C3
C1
C8
C7
C6
C17
C5
C4A
C2′
C4
C18
C19
C3′
C4′
C5′
C6′
C7′
C8′
C4A′
C8A′
C9


U(eq)

H3
H10A