3-(2-Bromoacetyl)phenyl benzoate

In the title compound, C15H11BrO3, the dihedral angle between the benzene rings is 72.59 (6)°. In the crystal, pairs of C—H⋯π contacts form inversion dimers. Additional C—H⋯O hydrogen bonds generate R 2 1(6) ring motifs and stack these dimers along the b axis. Short intermolecular Br⋯O contacts of 3.254 (3) Å are also observed and link the stacks into a three-dimensional network.

In the title compound, C 15 H 11 BrO 3 , the dihedral angle between the benzene rings is 72.59 (6) . In the crystal, pairs of C-HÁ Á Á contacts form inversion dimers. Additional C-HÁ Á ÁO hydrogen bonds generate R 2 1 (6) ring motifs and stack these dimers along the b axis. Short intermolecular BrÁ Á ÁO contacts of 3.254 (3) Å are also observed and link the stacks into a three-dimensional network.  et al. (1956). For hydrogen-bond motifs, see: Bernstein et al. (1995) Experimental Crystal data  Table 1 Hydrogen-bond geometry (Å , ).
Oral phenylephrine is extensively metabolized by monoamine oxidase (Naoto et al., 2008), an enzyme that is present in the gastrointestinal tract and in the liver. Therefore, compared to intravenous pseudoephedrine, it has a reduced and variable bioavailability, only up to 38% (Shwu-Jiuan & Mei-Hua, 1984;Jaakko & Erkki, 1959). Because phenylephrine is a directly selective α-adrenergic receptor agonist, it does not cause the release of endogenous noradrenaline, as pseudoephedrine does. Therefore, phenylephrine is less likely to cause side effects such as central nervous system stimulation, insomnia, anxiety, irritability, and restlessness (Junichi et al., 1956). Phenylephrine's effectiveness as a decongestant stems from its vasoconstriction of nasal blood vessels, thereby decreasing blood flow to the sinusoidal vessels, leading to decreased mucosal edema (D′Amico et al., 1956).

Experimental
All the chemicals used were of analytical reagent grade and were used directly without further purification. The title compound was synthesized according to an already reported method (Shwu-Jiuan & Mei-Hua, 1984). The crude product was recrystallized from an ethanol/chloroform mixture, to give colourless crystals in 78% yield.

Refinement
All H atoms were positioned geometrically, with C-H = 0.93 Å for aromatic H and C-H = 0.97 Å for methylene H and refined using a riding model with U iso (H) = 1.2U eq (C) for aromatic and methylene H.   Crystal packing along b axis for the title compound with hydrogen bonds drawn as dashed lines. 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