In:
Acta Crystallographica Section E Crystallographic Communications, International Union of Crystallography (IUCr), Vol. 76, No. 2 ( 2020-02-01), p. 155-161
Abstract:
In the title compound, C 12 H 15 N 3 O 5 S, a trisubstituted thiourea derivative, the central CN 2 S chromophore is almost planar (r.m.s. deviation = 0.018 Å) and the pendant hydroxyethyl groups lie to either side of this plane. While to a first approximation the thione-S and carbonyl-O atoms lie to the same side of the molecule, the S—C—N—C torsion angle of −47.8 (2)° indicates a considerable twist. As one of the hydroxyethyl groups is orientated towards the thioamide residue, an intramolecular N—H...O hydrogen bond is formed which leads to an S (7) loop. A further twist in the molecule is indicated by the dihedral angle of 65.87 (7)° between the planes through the CN 2 S chromophore and the 4-nitrobenzene ring. There is a close match between the experimental and gas-phase, geometry-optimized (DFT) molecular structures. In the crystal, O—H...O and O—H...S hydrogen bonds give rise to supramolecular layers propagating in the ab plane. The connections between layers to consolidate the three-dimensional architecture are of the type C—H...O, C—H...S and nitro-O...π. The nature of the supramolecular association has been further analysed by a study of the calculated Hirshfeld surfaces, non-covalent interaction plots and computational chemistry, all of which point to the significant influence and energy of stabilization provided by the conventional hydrogen bonds.
Type of Medium:
Online Resource
ISSN:
2056-9890
DOI:
10.1107/S2056989019017328
DOI:
10.1107/S2056989019017328/hb7880sup1.cif
DOI:
10.1107/S2056989019017328/hb7880Isup2.hkl
Language:
Unknown
Publisher:
International Union of Crystallography (IUCr)
Publication Date:
2020
detail.hit.zdb_id:
2843762-7
detail.hit.zdb_id:
2041947-8
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