[2-(1,3-Benzothiazol-2-ylmethoxy)-5-bromophenyl](4-chlorophenyl)methanone

In the title compound, C21H13BrClNO2S, the dihedral angle between the planes of the benzothiazole and chlorophenylmethanone groups is 71.34 (6)°. In the crystal, weak C—H⋯N hydrogen bonds lead to dimer formation, whereas Br⋯Cl short contacts [3.4966 (11) Å] form infinite chains along the a-axis direction. Further, the C—H⋯O, C—H⋯π and π–π [centroid–centroid distance = 3.865 (2) Å] interactions stabilize the three-dimensional network.


Experimental
To a solution of (5-bromo-2-hydroxyphenyl)(4-chlorophenyl) methanone (1 mmol) and (2-chloromethyl)benzo[d]thiazole (1 mmol) in dry THF, dry potassium carbonate (1 mmol) was added and stirred at room temperature for 8 h. The reaction mixture was concentrated to remove the solvent, diluted with ethyl acetate, washed with water, brine solution and dried over anhydrous sodium sulfate. The organic layer was concentrated to yield a residue which was purified by column chromatography using ethyl acetate and n-hexane as eluent (7:3, Rf = 3/4) to afford the product in 64% as a brown solid (m. p. 450 K). Suitable crystals for single-crystal X-ray study were obtained from ethanol solvent using slow evaporation technique at room temperature.

Refinement
All H atoms were positioned geometrically and refined using a riding model with U iso (H)= 1.2 U eq (C).  (Nardelli, 1995).

Figure 1
Molecular structure shows the atom labelling scheme with displacement ellipsoids for non-H atoms at 50% probability level, hydrogen atoms are arbitrary circle.

Figure 2
The C-H···N hydrogen bond dimers and Br···Cl short contacts of infinite chains along a axis.  Sheets of three-dimensional network structure.  where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max = 0.001 Δρ max = 0.45 e Å −3 Δρ min = −0.43 e Å −3 Special details Experimental. CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq