1-(2,6-Dichlorobenzoyl)-3-(3-methoxyphenyl)thiourea

The two aromatic rings in the title compound, C15H12Cl2N2O2S, enclose a dihedral angle of 37.49 (6)°. The molecule exists in the solid state in its thione form with typical thiourea C—S and C—O bonds lengths, as well as shortened C—N bonds. An intramolecular N—H⋯O hydrogen bond stabilizes the molecular conformation. In the crystal, molecules are connected by N—H⋯O and N—H⋯S hydrogen bonds, forming chains running along the a axis.

A view of compound (I), is shown in Fig 1. The N-C bonds differ significantly from one another but are short in comparison with the typical value for an N-C single bond (1.479 A°), and the C1-S1 bond is slightly shorter than a C-S double bond (1.681 A°), indicating partial electron delocalization in the N-C(S)-N(H)-C(O) structural segment. These distances are similar to those usually found in other substituted thioureas [Khawar Rauf et al., 2006a, 2006b, 2006c, 2007 Cambridge Structural Database, Version 5.28 (Allen, 2002)]. The dihedral angle between the aromatic rings is 37.49 (6)°, and the corresponding angles with the thiourea plane are 81.41 (7)° for the C11-C16 ring and 44.12 (7)° for the C21-C26 ring.
The thiocarbonyl and carbonyl groups are almost coplanar, as reflected by the O1-C2-N2-C1 and C2-N2-C1-N1 torsion angles. This is associated with the intramolecular N-H···O hydrogen bond (Table 1), forming a six-membered ring commonly observed in this class of compounds. In the crystal packing of (I), intermolecular N-H···S and N-H···O hydrogen bonds link the molecules into chains running along the a axis (Table 1, Fig. 2).

Experimental
Freshly prepared 2,6-Dichlorobenzoylisothiocyanate (2.32 g, 10 mmol) was added in acetone (30 ml) and stirred for 10 minutes. Afterwards neat 3-methoxyaniline (1.23 g, 10 mmol) was added and the resulting mixture was stirred for 1 h.The reaction mixture was then poured into acidified (pH 4) water and stirred well. The solid product was separated and washed with deionized water and purified by recrystallization from methanol/ 1,1-dichloromethane (1:1 v/v) to give fine crystals of the title compound (I), with an overall yield of 88%. Full spectroscopic and physical characterization will be reported elsewhere.

Refinement
Hydrogen atoms bonded to C were included in calculated positions and refined as riding on their parent C atom with C-H = 0.95 Å U iso (H) = 1.2U(C eq ) or C-H = 0.98 Å and U iso (H) = 1.5U(C eq ), respectively, for aromatic and methyl C atoms.
The methyl group is disordered over two positions with site occupation factors 0.76 (3) and 0.24 (3). For refinement the supplementary materials sup-2 O-C methyl and C aromatic ··· C methyl distances were restrained to be equal with an effective standard deviation of 0.02 Å. H atoms bonded to N were refined freely. Fig. 1. Molecular structure of (I) with the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bond is shown as dashed lines.