Abstract
In the title compound, C12H15N3O5S, a tris-ubstituted thio-urea derivative, the central CN2S chromophore is almost planar (r.m.s. deviation = 0.018 Å) and the pendant hy-droxy-ethyl 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 mol-ecule, the S-C-N-C torsion angle of -47.8 (2)° indicates a considerable twist. As one of the hy-droxy-ethyl groups is orientated towards the thio-amide residue, an intra-molecular N-H⋯O hydrogen bond is formed which leads to an S(7) loop. A further twist in the mol-ecule is indicated by the dihedral angle of 65.87 (7)° between the planes through the CN2S chromophore and the 4-nitro-benzene ring. There is a close match between the experimental and gas-phase, geometry-optimized (DFT) mol-ecular structures. In the crystal, O-H⋯O and O-H⋯S hydrogen bonds give rise to supra-molecular 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 supra-molecular association has been further analysed by a study of the calculated Hirshfeld surfaces, non-covalent inter-action plots and computational chemistry, all of which point to the significant influence and energy of stabilization provided by the conventional hydrogen bonds.
Highlights
In a continuation of our on-going work on these molecules and their metal complexes (Selvakumaran, Ng et al, 2011; Selvakumaran, Karvembu et al, 2011; Gunasekaran et al, 2017; Tan, Azizan et al, 2019), we describe the synthesis, spectroscopic characterization and X-ray crystallographic investigation of (I)
An approximate syn relationship is established between the thione-S and carbonyl-O atoms. Even though they lie to the same side of the molecule, the S1—C1—N2—C6 torsion angle of À47.8 (2) is consistent with a significant twist in the molecule about the C1—N2 bond; the O3—C6—N2— C1 torsion angle is À3.6 (2)
The hydroxyethyl groups lie to either side of the CN2S plane (r.m.s. deviation = 0.017 A )
Summary
In addition to accepting C—HÁ Á ÁO interactions, nitro groups are known to form nitro-N—OÁ Á Á(aryl) interactions (Huang et al, 2008) as well as participate as donors and acceptors in -hole interactions (Bauzaet al., 2014). Compound (I) is an example of a tri-substituted thiourea molecule, H2NC( S)NH2, whereby three of the four hydrogen atoms have been substituted to yield 4-NO2C6H4C( O)N(H)C( S)N(CH2CH2OH)2 Such N,N0-di(alkyl/aryl)-N0-benzoylthiourea derivatives have a carbonyl group connected to the thiourea framework and offer opportunities for rich coordination chemistry as these molecules feature both hard (oxygen) and soft (sulfur) donor atoms along with nitrogen donors and a variety of coordination modes have been observed. Over and above these considerations, there are continuing investigations into their biological potential, such as anti-microbial (Gemili et al, 2017; Binzet et al, 2018; Saeed et al, 2018), anti-cancer (Peng et al, 2016; Barolli et al, 2017; Jeyalakshmi et al, 2019) and anti-mycobacterium tuberculosis (Plutın et al, 2016) agents.
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