Abstract
In the title compound, C9H10ClNOS, the amide functional group -C(=O)NH- adopts a trans conformation with the four atoms nearly coplanar. This conformation promotes the formation of a C(4) hydrogen-bonded chain propagating along the [010] direction. The central part of the mol-ecule, including the six-membered ring, the S and N atoms, is fairly planar (r.m.s. deviation of 0.014). The terminal methyl group and the C(=O)CH2 group are slightly deviating out-of-plane while the terminal Cl atom is almost in-plane. Hirshfeld surface analysis of the title compound suggests that the most significant contacts in the crystal are H⋯H, H⋯Cl/Cl⋯H, H⋯C/C⋯H, H⋯O/O⋯H and H⋯S/S⋯H. π-π inter-actions between inversion-related mol-ecules also contribute to the crystal packing. DFT calculations have been performed to optimize the structure of the title compound using the CAM-B3LYP functional and the 6-311 G(d,p) basis set. The theoretical absorption spectrum of the title compound was calculated using the TD-DFT method. The analysis of frontier orbitals revealed that the π-π* electronic transition was the major contributor to the absorption peak in the electronic spectrum.
Highlights
Methylthioanilines are a class of S- and N- heterocyclic compounds that are widely used in antimicrobial applications (Chatterjee et al, 2012; Martin et al, 2016; Das et al, 2017; Cross et al, 2018)
We report the synthesis and the solid state structure of 2-chloro-N-[4(methylsulfanyl)phenyl]acetamide, a methylthioaniline derivative
Hirshfeld surface analysis was used to investigate the interactions within the crystal structure and DFT calculations were performed to study the frontier molecular orbitals of the title compound and its electronic properties
Summary
Methylthioanilines are a class of S- and N- heterocyclic compounds that are widely used in antimicrobial applications (Chatterjee et al, 2012; Martin et al, 2016; Das et al, 2017; Cross et al, 2018). Metal–methylthioaniline complexes have been utilized in many applications including as homogeneous catalysts, organic semiconductors, antibacterial and antifungal drugs (Chen et al, 2019; Kumar et al, 2017; Mandal et al, 2018; Wang et al, 2009). We report the synthesis and the solid state structure of 2-chloro-N-[4(methylsulfanyl)phenyl]acetamide, a methylthioaniline derivative. Hirshfeld surface analysis was used to investigate the interactions within the crystal structure and DFT calculations were performed to study the frontier molecular orbitals of the title compound and its electronic properties. Symmetry code: (i) x þ 12; y; Àz þ 32
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