Crystal structure, Hirshfeld surface analysis and computational study of 2-chloro-N-[4-(methylsulfanyl)phenyl]acetamide

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 molecule, 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 interactions between inversion-related molecules 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.

Source: Acta Crystallographica Section E - March 30, 2020 Category: Chemistry Authors: Mongkholkeaw, S. Songsasen, A. Duangthongyou, T. Chainok, K. Suramitr, S. Wattanathana, W. Wannalerse, B. Tags: 4-methylthioaniline chloroacetyl chloride hydrogen bonds π – interactions crystal structure research communications Source Type: research