Source of materialAll chemicals used for the preparation were of reagent grade quality. Experimental detailsAll the H atoms were located in a Fourier difference map. The aryl and amino H atoms were refined isotropically without restraints. The ethyl H atoms were constrained to ride in the rigid-body approximation (d(CH) = 0.97 Å and 0.96 Å, U iso (H) = 1.2 and 1.5U eq(C), respectively). DiscussionIn recent years, a special attention has been paid to thiourea and its derivatives [4,5]. Among these works, some were focused on the application of the thiourea derivatives [6]. It was reported that some unexpected coordination compounds and structures were obtained by the reaction with thiourea and copper(II) [7]. In the crystal structure of the title compound, there are two plane moieties, the p-Cl-phenyl ring and the six-membered ring formed by the intramolecular hydrogen bond (N1H1¢···O1; figure, top). The mean deviations for the two molecular planes are 0.011 Å and 0.036 Å, respectively, and the dihedral angle between them is 28.3°. The hydrogen-bonded six-membered ring structure is similar in the previous reports about the crystal structures containing thiourea [2,3]. A dimer of the title molecule ( figure, bottom) is formed by the intermolecular hydrogen bond N2H2¢···S1 similar to that reported before [3]. There is no hydrogen bond between the chlorine atom and NH, although the chlorine atom has a trend to form hydrogen bonds [1]. Apparently, the molecular conformation and the molecular packing are governed from sulfur and oxygen atoms rather than chlorine atom. Comparing the title structure with the similar crystal structures [1][2][3], there are no noticeable differences between main bond distances.

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