1730
J Chem Crystallogr (2011) 41:1729–1736
The results from X-ray diffraction have been compared
124.46, 128.35, 129.12, 129.77, 130.95, 131.63, 139.44,
147.96, 154.21, 167.19 (C=S), 191.65 (C=O).
to those obtained from ab initio DFT and HF calculations,
finding a good agreement with the structure determined
from the single-crystal measurements.
X-Ray Structure Determination
A yellow prismatic crystal with approximate dimensions of
0.20 9 0.15 9 0.10 mm was selected for data collection.
The X-ray diffraction data were collected on a Kappa CCD
Nonius diffractometer. Reflection data were measured at
298 K using graphite monochromated Mo Ka radiation
Experiment and Computational Methods
Synthesis
˚
The title compound was prepared by reaction of N-aryl-
rhodanine (0.01 M), aldehyde (0.01 M), 5 mL of acetic
acid and sodium acetate (0.02 M) in a 150 mL boiling
flask. Then 2 mL of triethylamine are added to this mix-
ture. The system is refluxed for 4 h, forming a yellow solid.
The crystals obtained are filtered and recrystallized in
ethanol. Synthesis of the compound was performed as
follows (Fig. 1).
(k = 0.71073 A). Intensities for 4080 reflections were
measured with indices -11 \ h \ 11, -12 \ k \ 11,
-15 \ l \ 15. The structure was determined by consider-
ing 2591 reflections with I ꢁ 4rðIÞ. The structure was
solved by direct methods using the SHELXS-97 [7].
A Fourier synthesis revealed the complete structure, which
was refined by full-matrix least squares. All non-H atoms
refined anisotropically. The positions of the H atoms bon-
ded to C atoms were calculated. The H atoms were located
from a difference Fourier map and included in the refine-
ment with the isotropic temperature factor of the carrier
atom. The final least-squares cycle using SHELXL-97 [8]
gave R = 0.05 for the observed reflections with S = 0.95,
Spectral Analysis
All reagents and solvents for synthesis and spectroscopic
studies were commercially available and used as received
without further purification. The IR spectra was recorded
on a JASCO 4200 FT-IR spectrometer as a KBr pellet. The
1H and 13C NMR spectra were measured in CDCl3 with a
BRUKER Ac DPX-200 (300 MHz) spectrometer at 25 °C.
3
3
˚
˚
(Dq)min = -0.425 e/A , (Dq)max = 0.219 e/A . An ORTEP
[9] view of the molecular structure with the atomic num-
bering is shown in Fig. 2. Atomic scattering factors for
heavy atoms were taken from International Tables for
X-ray Crystallography [10] while the factors for H were
Spectral Data of ARNO
(Z)-5-(4-nitrobenzyliden)-3-N(2-ethoxyphenyl)-2-thioxo-
thiazolidin-4-one (2g, yield 75%, yellow solid, M.p.
210 °C). IR (KBr, cm-1): 3407 broad band, 3035 (C–N),
1710 (C=O),1256 (C=S).
1H NMR, (CDCl3, 300 MHz) d (ppm) J (Hz): 1, 42 (t,
3H, –O–CH2–CH3, J3 = 6.97), 4.06 (oct, 1H, J2 = 2.2,
J3 = 6.95) (–O–CH2–CH3), 4.11 (oct, 1H, J2 = 2.2;
J3 = 6.95), (–O–CH2–CH3), 7.53–7.08 (m, 4H), 7.71 (d,
2H, J = 8.75) 7.79 (s, 1H, –CH=C–), 8.53 (d, 2H,
J = 8.80).
Fig. 2 General view of molecule with atomic numbering scheme
(thermal ellipsoids drawn at 50% probability). H atoms are shown as
small spheres of arbitrary radii
13C NMR, (CDCl3, 300 MHz) d (ppm): 14.17 (O–CH2–
CH3), 64.43 (–O–CH2–CH3), 113.48, 121.00, 123.26,
Fig. 1 Preparation and chemical structure of (Z)-5-(4-nitrobenzyliden)-3-N(2-ethoxyphenyl)-2-thioxo-thiazolidin-4-one (ARNO). Reagents and
conditions: (a) ClCH2CO2H, 70 °C; (b) NO2C6H4CHO, CH3COOH, CH3COONa, 90 °C
123
Benhalima, Nadia
