4-Chlorobenzothioamide

Abstract

In the title compound, C7H6ClNS, the dihedral angle between the aromatic ring and the thio­amide fragment is 28.1 (2)°. The structure features a π-stacking inter­action between the aromatic rings with a slight offset of the rings, giving a centroid–centroid separation of 3.7942 (2) Å. There are inter­molecular hydrogen-bonding inter­actions between the amino group and the S atoms.

Crystal Landscape of Primary Aromatic Thioamides

“…A polymorphic screen was performed using evaporative crystallization from a range of different solvents (details are provided in the Supporting Information). There was no evidence of polymorphism for all the thioamides investigated in this study except for thioamide 14 , for which we observed a new polymorph with no evidence of the previously reported polymorph . A more comprehensive polymorphic screen may identify new polymorphs of these thioamides.…”

“…The third set of interactions observed is the centrosymmetric R 2 2 (8) dimer with an offset C(4) chain formed between neighboring thioamides, as observed in 12 , 13 , and 14α . Because the dimers are offset, the ladder motif is not formed (Figure ).…”

“…In the case of 5 , only twinned crystals could be obtained from a variety of solvents and thus a method described by Chetina was used to grow crystals suitable for X-ray diffraction. The crystal structures of compounds 2 , 3 , 8 , 12 , 14α , and 15 have been previously described. The structures of 2 and 15 were redetermined in this study and found to be consistent with the literature.…”

4-Methylbenzenecarbothioamide

“…1), the bond distances and angles agree with the corresponding bond distances and angles reported in closely related compounds (Khan et al, 2009a;2009b;2009c;Jian et al, 2006;Ali et al, 2010). In the title compound, the mean-plane of the carbothioamide group (S1/N1/C7) is slightly twisted with respect to the mean-plane of the phenyl ring (C1-C6), making a dihedral angle of 17.03 (10)°.…”

“…In addition, they are important ligands in the field of coordination chemistry (Lebana et al, 2008). In continuation to our work on thioamides (Khan et al, 2009a;2009b;2009c;Ali et al, 2010), we have synthesized 4-methylbenzenecarbothioamide, (I). In this article we report the crystal structure of the title compound.…”