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

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 0.0015 Å] 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—H⋯S inter­actions. In the extended structure, supra­molecular layers parallel to (102) are formed via a combination of 3-tolyl-C—H⋯π(3-tol­yl) and weak π–π 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.