2-(1,3-Benzoxazol-2-ylsulfanyl)-1-phenylethanone

In the title compound, C15H11NO2S, a new thio-benzoxazole derivative, the dihedral angle between the benzoxazole ring and the phenyl ring is 9.91 (9)°. An interesting feature of the crystal structure is the short C⋯S [3.4858 (17) Å] contact, which is shorter than the sum of the van der Waals radii of these atoms. In the crystal structure, molecules are linked together by zigzag intermolecular C—H⋯N interactions into a column along the a axis. The crystal structure is further stabilized by intermolecular π–π interactions [centroid–centroid = 3.8048 (10) Å].

In the title compound, C 15 H 11 NO 2 S, a new thio-benzoxazole derivative, the dihedral angle between the benzoxazole ring and the phenyl ring is 9.91 (9) . An interesting feature of the crystal structure is the short CÁ Á ÁS [3.4858 (17) Å ] contact, which is shorter than the sum of the van der Waals radii of these atoms. In the crystal structure, molecules are linked together by zigzag intermolecular C-HÁ Á ÁN interactions into a column along the a axis. The crystal structure is further stabilized by intermolecularinteractions [centroidcentroid = 3.8048 (10) Å ].

D-HÁ
In the molecule of the title compound, (Fig. 1), a new thio-benzoxazole derivative, the dihedral angle between the benzoxazole ring and the phenyl ring is 9.91 (9)°. The interesting feature of the crystal structure is the short C6···S1 i [3.4858 (17) Å; (i) -1 + x, y, z] contact which is shorter than the sum of the van der Waals radii of these atoms. In the crystal structure, the molecules are linked together by a zig-zag intermolecular C-H···N interactions (Table 1) which packed into a column along the a axis (Fig. 2). The crystal structure is further stabilized by the intramolecular π-π interactions [Cg1···Cg2 i = 3.8048 (10) Å].

Experimental
Sodium carbonate (4.5 mmol) was added to a stirred solution of 2-mercaptobenzoxazole (3 mmol) in ethanol (15 mL) and water (15 mL) and stirred in room temperature for 30 min. α-Bromoacetophenone (3 mmol) was added to the reaction mixture and stirring was continued for 1h. The reaction was monitored by TLC and after 60 min. showed the complete disappearance of starting material. The reaction mixture was poured into 100 mL of 1M HCl containing 50 g of crushed ice. Figures Fig. 1. The molecular structure of the title compound, showing 40% probability displacement ellipsoids and the atomic numbering.

Special details
Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.