Synthesis and Structural Characterization of the 5-(2-Haloethyl)pyrimidines – Hydrogen-Bonded chains in α-(1-Carbamyliminomethylene)-γ-Butyrolactone
Abstract
:Introduction
Results and Discussion
Synthesis
X-ray crystal structure study
N1−C6 | 1.363(2) | O3−C7 | 1.2251(19) | |
N1−C7 | 1.3900(18) | C2−C3 | 1.453(2) | |
N2−C7 | 1.339(2) | C3−C6 | 1.333(2) | |
O1−C2 | 1.3417(17) | C3−C4 | 1.495(2) | |
O1−C5 | 1.450(2) | C4−C5 | 1.518(2) | |
O2−C2 | 1.2173(19) | |||
C6−N1−C7 | 121.43(13) | C2−C3−C4 | 108.73(12) | |
C2−O1−C5 | 110.77(12) | C3−C4−C5 | 102.74(13) | |
O2−C2−O1 | 120.86(14) | O1−C5−C4 | 107.73(12) | |
O2−C2−C3 | 129.10(15) | C3−C6−N1 | 125.09(13) | |
O1−C2−C3 | 110.02(12) | O3−C7−N2 | 124.88(15) | |
C6−C3−C2 | 121.18(13) | O3−C7−N1 | 121.05(15) | |
C6−C3−C4 | 130.00(14) | N2−C7−N1 | 114.07(13) |
D−H···A | D−H (Å) | H···A (Å) | D···A (Å) | D−H··· A |
---|---|---|---|---|
N1−H1···O2i | 0.85(2) | 2.06(2) | 2.869(2) | 158(2) |
N2−H2A···O2i | 0.90(2) | 2.16(2) | 2.974(2) | 150(2) |
N2−H2B···O3ii | 0.93(2) | 1.96(2) | 2.884(2) | 174(2) |
Experimental Section
General
Synthesis
Crystal structure determination of 2
Formula | C6H8N2O3 |
Formula weight | 156.14 |
Crystal system | monoclinic |
Space group | P 21/c |
Unit cell dimensions | |
a (Å) | 7.0522(8) |
b (Å) | 6.6691(6) |
c (Å) | 15.1031(16) |
β (o) | 94.869(9) |
V (Å3) | 707.76(13) |
Z | 4 |
Dcalc. (g cm-3) | 1.465 |
Absorption coefficient μ (mm-1) | 0.119 |
F(000) | 328 |
θ range (°) | 2.71 - 27.99 |
Index ranges | -9 ≤ h ≤ 9 |
-8 ≤ k ≤ 8 | |
-11 ≤ l ≤ 19 | |
Collected reflections No. | 2941 |
Independent reflections No. / Rint. | 1702 / 0.0231 |
Reflections No. I ≥ 2σ(I) | 1063 |
Refined parameters No. | 112 |
Goodness-of-fit on F2, S | 1.001 |
R [I ≥ 2σ(I)] / R [all data] | 0.0398 / 0.0783 |
wR [I ≥ 2σ(I)] / wR [all data] | 0.1061 / 0.1231 |
Max./min. electron density (e Å-3) | 0.189 / -0.141 |
Acknowledgements
References
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Gazivoda, T.; Raić-Malić, S.; Hergold-Brundić, A.; Cetina, M. Synthesis and Structural Characterization of the 5-(2-Haloethyl)pyrimidines – Hydrogen-Bonded chains in α-(1-Carbamyliminomethylene)-γ-Butyrolactone. Molecules 2008, 13, 2786-2795. https://doi.org/10.3390/molecules13112786
Gazivoda T, Raić-Malić S, Hergold-Brundić A, Cetina M. Synthesis and Structural Characterization of the 5-(2-Haloethyl)pyrimidines – Hydrogen-Bonded chains in α-(1-Carbamyliminomethylene)-γ-Butyrolactone. Molecules. 2008; 13(11):2786-2795. https://doi.org/10.3390/molecules13112786
Chicago/Turabian StyleGazivoda, Tatjana, Silvana Raić-Malić, Antonija Hergold-Brundić, and Mario Cetina. 2008. "Synthesis and Structural Characterization of the 5-(2-Haloethyl)pyrimidines – Hydrogen-Bonded chains in α-(1-Carbamyliminomethylene)-γ-Butyrolactone" Molecules 13, no. 11: 2786-2795. https://doi.org/10.3390/molecules13112786
APA StyleGazivoda, T., Raić-Malić, S., Hergold-Brundić, A., & Cetina, M. (2008). Synthesis and Structural Characterization of the 5-(2-Haloethyl)pyrimidines – Hydrogen-Bonded chains in α-(1-Carbamyliminomethylene)-γ-Butyrolactone. Molecules, 13(11), 2786-2795. https://doi.org/10.3390/molecules13112786