Conclusions
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1.
In urethane crystals, infinite chains of hydrogen bonds organize the urethane molecules into layers with two principal types of packing: “fir-tree” and “stacked.” The stacked packing sometimes leads to the formation of a quasiskeletal structure.
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2.
The geometry of the hydrogen bonds is governed by the packing of neighboring molecules.
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3.
The frequency of the stretching vibration band of the NH group in IR spectra cannot be used to judge the geometry of hydrogen bonds in crystalline urethanes, since the geometry is governed not only by the H...O interaction of the hydrogen bond N-H...O=C, but also by the total energy of intermolecular interaction.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1080–1084, May 1989.
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Atovmyan, E.G., Alimova, L.L. & Filipenko, O.S. Hydrogen bonding and crystal structure of urethanes. Russ Chem Bull 38, 976–980 (1989). https://doi.org/10.1007/BF00955428
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DOI: https://doi.org/10.1007/BF00955428