Crystal structure, Hirshfeld surface analysis and computational study of 2-chloro-N-[4-(methyl-sulfan-yl)phen-yl]acetamide.

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. ?-? 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 ?-?* electronic transition was the major contributor to the absorption peak in the electronic spectrum.

SUBMITTER: Mongkholkeaw S 

PROVIDER: S-EPMC7133040 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature