3-{(E)-[1-(2-Hydroxyphenyl)ethylidene]amino}-1-(2-methylphenyl)thiourea

Abstract

In the title thiourea derivative, C16H17N3OS, the hydroxy- and methyl-substituted benzene rings form dihedral angles of 9.62 (12) and 55.69 (6)°, respectively, with the central CN3S chromophore (r.m.s. deviation = 0.0117 Å). An intramolecular O—H...N hydrogen bond ensures the coplanarity of the central atoms. The H atoms of the NH groups are syn and the conformation about the N=C double bond [1.295 (4) Å] is E. In the crystal, helical supramolecular chains sustained primarily by N—H...S hydrogen bonds are found. Additional stabilization is provided by C—H...π and π–π [ring centroid(hydroxybenzene)...ring centroid(methylbenzene) = 3.8524 (18) Å] interactions.