2-(1,3-Benzothiazol-2-ylsulfanyl)-N-(2-methylphenyl)acetamide

In the title molecule, C16H14N2OS2, the benzene ring and the benzo[d]thiazole mean plane form a dihedral angle of 75.5 (1)°. The acetamide group is twisted by 47.7 (1)° from the attached benzene ring. In the crystal, molecules related by translation along the a axis are linked into chains through N—H⋯O hydrogen bonds.

In the title molecule, C 16 H 14 N 2 OS 2 , the benzene ring and the benzo[d]thiazole mean plane form a dihedral angle of 75.5 (1) . The acetamide group is twisted by 47.7 (1) from the attached benzene ring. In the crystal, molecules related by translation along the a axis are linked into chains through N-HÁ Á ÁO hydrogen bonds.   Table 1 Hydrogen-bond geometry (Å , ). (2) 168 (2) Symmetry code: (i) x þ 1; y; z.
The molecular structure of title compound and the atom-mumbering scheme are shown in Fig. 1 The acetamide group is twisted at 47.7 (1)° from the attached benzene ring. C1 atom attached to the benzene ring is coplanar to the benzene ring with an r.m.s deviation of 0.0046 Å. As a result of π-π conjugation, the C sp 2 -S bond [S1-C10 = 1.745 (2) Å] is significantly shorter than the C sp 3 -S bond [S1-C9 = 1.812 (2)  The crystal structure is stablized by the intermolecular N-H···O hydrogen bond (Table 1) interaction.

Experimental
The title compound was synthesized by the reaction of the benzo[d]thiazol-2-thiol with 2-methylphenyl carbamic chloride in the refluxing ethanol. Crystals of (I) suitable for single-crystal X-ray analysis were grown by slow evaporation of a solution in chloroform-ethanol (1:1).

Refinement
Atom H1 attached to N atom was located on a difference map and refined isotropically. Other H atoms were positioned geometrically (C-H = 0.95-0.99 Å), and refined as riding, with U iso (H) = 1.2-1.5U eq (C).  View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 60% probability level.

Special details
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.