Bis[4-(chloroacetyl)phenyl] ether

The title compound, C16H12Cl2O3, crystallizes with two independent molecules in the asymmetric unit. The dihedral angles between the planes of the benzene rings in the two independent molecules are 68.65 (2) and 68.47 (3)°. The short distance of 3.899 (5) Å between the centroids of the benzene rings of neighbouring molecules indicate π–π interactions. The crystal structure is stabilized by a network of intermolecular C—H⋯O hydrogen bonds.


Bis[4-(chloroacetyl)phenyl] ether
Fan-Lei Meng and Liang-Zhong Xu S1. Comment The title compound, was obtained unintentionally as an intermediate for the synthesis of Triazole compounds. Triazole compounds had been found to show wide spread biological activities. Many of them had been developed and used as fungicides, plant growth regulators and medicine. (Fujimoto & Quinn, 1988) we report here the crystal structure of (I).
The title compound, crystallizes in space group with two independent molecules in the asymmetric unit (Figs. 1,2). All bond lengths and angles are normal and in a good agreement with those reported previously (Grossert et al., 1984). The angles of C6-O2-C9 and C22-O15-C25 in the two independent molecules are 119.06 (2) and 120.07 (3)°.
However, the two benzene rings are not coplanar planar. The dihedral angles between the planes of benzene rings in the two independent molecules are 68.65 (2) and 68.47 (3)°. π-π stacking interactions are present in the structure. The crystal structure is stabilized by a network of hydrogen bonds and van der Waals interations.

S2. Experimental
A mixture of 1-phenoxybenzene(5.0 mmol) and anhydrous aluminium chloride were added to a solution of 50 mL of dry dichloromethane in a flask equipped with stirrer and reflux condenser. Chloroacetyl chloride (10.0 mmol) was slowly added from a dropping-funnel to the boiling mixture during 30 minutes After this addition, the reaction mixture was heated with strring for two hours at boiling. The mixture was poured into ice-water and extracted with dichloromethane.
The extract was dried over anhydrous magnesium sulfate, and dichloromethane was distilled off. The residue was purified by a column chromatography to obtain the title compound (10.1 g, yield 62%). (Edward & Sibelle, 1963). Single crystals suitable for X-ray measurement were obtained by recrystallization from petroleum ether at room temperature.

S3. Refinement
All H atoms were found on difference maps, H atoms were placed in calculated positions, with C-H = 0.93 or 0.97Å, and included in the final cycles of refinement using a riding model, with U iso (H) = 1.2 times U eq (C).

Figure 1
View of the first molecule of the title compound (I), with displacement ellipsoids drawn at the 50% probability level.

Figure 2
View of the second molecule of the title compound (I), with displacement ellipsoids drawn at the 50% probability level.
where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max = 0.002 Δρ max = 0.64 e Å −3 Δρ min = −0.71 e Å −3 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.  0.0175 (7) 0.0171 (7) 0.0184 (7) 0.0019 (6)