1-(3-Bromopropoxy)-4-chlorobenzene

In the molecule of the title compound, C8H8BrClO, the Cl atom lies slightly out of the aromatic ring plane [displacement = 0.072 (3) Å]. In the crystal structure, a π–π contact between the phenyl rings [centroid–centroid distance = 3.699 (3) Å] may stabilize the structure. There also exists a C—H⋯π contact between the methylene group and the chlorophenyl ring.

In the molecule of the title compound, C 8 H 8 BrClO, the Cl atom lies slightly out of the aromatic ring plane [displacement = 0.072 (3) Å ]. In the crystal structure, acontact between the phenyl rings [centroid-centroid distance = 3.699 (3) Å ] may stabilize the structure. There also exists a C-HÁ Á Á contact between the methylene group and the chlorophenyl ring.

S1. Comment
Omoconazole has a high antifungal activity and a broad spectrum (Zirngibl et al., 1988). As part of our ongoing studies in this area, we report herein the crystal structure of the title compound.
In the molecule of the title compound ( Fig. 1) the bond lengths (Allen et al., 1987) and angles are within normal ranges.
Ring A (C3-C8) is, of course, planar, and the Cl atom lies slightly out of the ring plane [0.072 (3)  In the crystal structure, the π-π contact between the phenyl rings, Cg1-Cg1 i [symmetry code: (i) -x, 1 -y, -z, where Cg1 is centroid of the ring A (C3-C8)] may stabilize the structure, with centroid-centroid distance of 3.699 (3) Å. There also exists a C-H···π contact (Table 1) between the methylene group and the chlorophenyl ring.

S2. Experimental
Phenol (47.0 g, 0.5 mol), CuCl 2 (147.4 g, 1.1 mol) and hydrochloric acid (350 ml, 8.5 mol/L) were mixed in a threenecked flask equipped with a reflux condenser and a magnetic stirrer. The solution was stirred at 383 K for 10 h, and then cooled to room temperature. Subsequently the reaction mixture was extracted with toluene for three times, and then the extracts were dried and the solvents were completely stripped by evaporation. After isolated by column chromatography (silica), p-chlorophenol was obtained (yield; 44.8 g, 75%) (Menini & Gusevskaya, 2006). p-Chlorophenol (26.0 g, 0.2 mol) was dissolved with stirring in water (30 ml) containing sodium hydroxide (9.0 g, 0.23 mol) and added dropwise to excess refluxing ethylene dibromide (74.8 g, 0.4 mol). The reaction mixture was heated under reflux for 6 h, cooled and extracted into ether (3 x 150 ml). The combined organic extracts were washed with water, dried over Na 2 S0 4 , filtered and evaporated to dryness to yield an oil. Fractionation under reduced pressure yielded p-chlorophenoxyethyl bromide as a colorless oil, then cooled to give the title compound as colorless solid (yield; 27.6 g, 57%) (Baggaley & Watts, 1982).
Crystals suitable for X-ray analysis were obtained by slow evaporation of an petroleum ether solution.

S3. Refinement
H atoms were positioned geometrically, with C-H = 0.93 and 0.97 Å for aromatic and methylene H, respectively, and constrained to ride on their parent atoms with U iso (H) = 1.2U eq (C).  The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% 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.