Novel One-Pot, Multicomponent Synthetic Strategy IRUꢀWKHꢀ6\QWKHVLVꢀRI
\UUROR>ꢁꢂꢃꢄa]benzimidazole and Pyrrolo[1,2-a]quinoxaline Derivatives
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a
b,c
d
c,e
b
Emilian Georgescu, Alina Nicolescu, Florentina Georgescu, Sergiu Shova, Florina Teodorescu,
c
b,c
Ana-Maria Macsim, Calin Deleanu. *
a
Research Center Oltchim, St. Uzinei 1, RO-240050 Ramnicu Valcea, Romania.
C. D. Nenitescu” Centre of Organic Chemistry, Roumanian Academy, Spl. Independentei 202-B, RO-060023 Bucharest, Romania.
b
“
c
“Petru Poni” Institute of Macromolecular Chemistry, Roumanian Academy, Aleea Grigore Ghica Voda 41-A, RO-700487 Iasi,
Romania.
d
Research Dept., Teso Spec S. R. L., Str. Muncii 53, RO-915200 Fundulea, Calarasi, Romania.
Institute of Chemistry, Academy of Sciences, Str. Academiei 3, MD-2028, Chisinau, Republic of Moldova.
e
E-mail: calin.deleanu@yahoo.com
Received: The date will be inserted once the manuscript is accepted.
Supporting Information
Materials and Methods.
X-Ray crystallographic measurements were carried out with an Oxford-Diffraction XCALIBUR E CCD diffractometer equipped with
graphite-monochromated Mo-KĮradiation. Single crystals were positioned at 40 mm from the detector and 346, 298 and 424 frames
were measured each for 150, 200 and 150 s over 1° scan width for 4a, 5c and 8c, respectively. The unit cell determination and data
[
1]
integration were carried out using the CrysAlis package of Oxford Diffraction. The structures were solved by direct methods using
[
2]
[3]
Olex2 and refined by full-matrix least-squares on F² with SHELXL-97. Atomic displacements for non-hydrogen, atoms were refined
using an anisotropic model. All H atoms were introduced in idealized positions (dCH = 0.96 Å) using the riding model with their
isotropic displacement parameters fixed at 120% of their riding atom. In the absence of significant anomalous scattering, the absolute
configuration for 4a and 5c structures could not be reliably determined. Friedel pairs were merged and any references to the Flack
parameter were removed. The 8c sample gave a weak diffraction and the resolution of the collected X-ray data has been estimated to be
1
.0 Å. Nevertheless the structure could be solved and electron density of the molecule was well defined allowing to determine the atomic
connectivity and to refine the model with anisotropic temperature factors. Trifluoracetic acid and water solvate molecules were found to
be severely disordered and their positional parameters were refined in combination with PART and SADI restraints using isotropic model
for non-H atoms. Taking into account these areas of possible solvent inclusion, the “Use solvent mask routine” subroutine of the Olex2
was used to account for the scattering from a disordered solvent molecule. As the result, the value of R1obs has been reduced from 0.1551
to 0.0995. The molecular plots were obtained using the Olex2 program.
X-ray crystallography
These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data
Centre, 12 Union Road, Cambridge CB2 1EZ, UK).
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a: C H N O , Mr = 420.45 g mol , size 0.40u0.02u0.02 mm , monoclinic, space group P2 , a = 4.5150(7) Å, b = 9.9297(13) Å, c =
2
7
2
0
2
3
1
3
-3
-1
2.904(4) Å, E = 91.867(14)q, V = 1026.3(3) Å , Z = 2, ȡcalcd = 1.361 g cm , ȝꢀMoKĮꢀꢁ ꢁ0.090 mm , F(000) = 440, 7599 reflections in
h(-4/5), k(-12/12), l(-28/28), measured in the range 3.56 d Ĭ d 51.98, T = 173 K, completeness Ĭmax=99.91%, 2156 independent
reflections, Rint = 0.1328, 290 parameters, 1 restraints, R1obs=0.0967, wR2obs = 0.1749, R1all = 0.1664, wR2all = 0.2003, GoF = 1.036,
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largest difference peak and hole: 0.34/-0.31 e A . CCDC – 980024.
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5
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c: C H F N O , Mr = 472.48 g mol , size 1.00u0.70u0.03 mm , triclinic, space group P-1, a = 7.1282(14) Å, b = 8.8913(18) Å, c =
28 22 2 2 3
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-3
-1
9.611(3) Å, Į = 102.928(15)q, E = 91.713(14)q, Ȗ = 106.364(17)q, V = 1156.6(4) Å , Z = 2, ȡ
= 1.357 g cm , ȝꢀMoKĮꢀꢁ ꢁ0.100 mm ,
calcd
F(000) = 492, 7429 reflections in h(-8/7), k(-10/10), l(-14/24), measured in the range 4.92 d Ĭ d 52.00, T = 173 K, completeness
Ĭmax=98.90%, 4479 independent reflections, Rint = 0.0722, 317 parameters, 0 restraints, R1obs=0.0694, wR2obs = 0.12038, R1all = 0.1547,
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wR2all = 0.1502, GoF = 0.939, largest difference peak and hole: 0.29/-0.32 e A . CCDC – 980025.
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3
8
c: C21.7H18.55F3.55N O , Mr = 455.59 g mol , size 0.50u0.05u0.05 mm , triclinic, space group P-1, a = 3.8246(5) Å, b = 13.713(2) Å, c
2 5.05
3
-3
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=
20.895(3) Å, Į = 104.754(14)q, E = 93.402(13)q, Ȗ = 90.436(12)q, V = 1057.6(3) Å , Z = 2, ȡcalcd = 1.431 g cm , ȝꢀMoKĮꢀꢁ ꢁ0.122 mm
F(000) = 470, 6743 reflections in h(-8/7), k(-12/15), l(-23/17), measured in the range 3.08 d Ĭ d 46.52, T = 160 K, completeness
1
,
Ĭmax=99.40%, 3031 independent reflections, Rint = 0.1099, 293 parameters, 14 restraints, R1obs=0.0995, wR2obs = 0.2308, R1all = 0.1667,
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wR2all = 0.2636, GoF = 0.959, largest difference peak and hole: 0.31/-0.27 e A . CCDC – 1036766.
Georgescu, Emilian
