A new monoclinic polymorph of N-(3-methylphenyl)ethoxycarbothioamide: Crystal structure and Hirshfeld surface analysis

Abstract

The title compound, C 10 H 13 NOS, is a second monoclinic polymorph (space group P2 1 /c, Z′ = 2) of the previously reported C2/c (Z = 1) polymorph [Tadbuppa & Tiekink (2005). Z. Kristallogr. New Cryst. Struct. 220, 395-396]. Two independent molecules comprise the asymmetric unit of the new polymorph and each of these exists as a thioamide-thione tautomer. In each molecule, the central CNOS chromophore is strictly planar [r.m.s. deviations = 0.0003 and 0.0015Å] and forms dihedral angles of 6.17(5) and 20.78(5) with the N-bound 3-tolyl rings, thereby representing the major difference between the molecules. The thione-S and thioamide-N-H atoms are syn in each molecule and this facilitates the formation of an eight-membered thioamide {SCNH} 2 synthon between them; the dimeric aggregates are consolidated by pairwise 3-tolyl-C-HS interactions. In the extended structure, supramolecular layers parallel to (102) are formed via a combination of 3-tolyl-C-H(3-tolyl) and weak-interactions [inter-centroid distance between 3-tolyl rings = 3.8535(12)Å]. An analysis of the Hirshfeld surfaces calculated for both polymorphs reveals the near equivalence of one of the independent molecules of the P2 1 /c form to that in the C2/c form.