[2,2′-Iminodiethanolato(2−)-κ3 O,N,O′][4-(methoxycarbonylmethyl)phenyl]boron

The title compound, C13H18BNO4, was readily obtained from the reaction of methyl 4-boronobenzene acetate with ethanolamine. A combination of intermolecular N—H⋯O hydrogen bonds and C—H⋯π interactions leads to the pairwise association of molecules.

Data collection: CrystalClear (Rigaku, 2002); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: publCIF (Westrip, 2010). also widespread in synthetic chemistry and this is due mainly to the pioneering work of H. C. Brown and coworkers and Suzuki and his coworkers (Miyaura & Suzuki, 1995). Corey, Bakshi and Shibata (Corey et al., 1987) discovered that a chrial oxazaborolidine ("CBS" reagent) which contains both boron-nitrogen and boron-oxygen bonds was capable of effecting enantioselective reduction of prochiral ketones, imines, and oximes to produce chiral alcohols, amines, and amino alcohols in excellent yields and ee's. Corey's group has also shown that chiral oxazaborolidine-aluminium bromide complexes (Liu et al. 2007) are also effective catalysts for enantioselective Diels-Alder reactions. In principle, oxazaborolidines are derived from reactions of a boronic acid and aminoalcohols and a less well known application of oxazaborolidines is to facilitate the conversion of a pinacolatoborane, by mild acid-catalysis (Jung & Lazarova, 1999), to the corresponding boronic acid, a key step for cupric acetate promoted coupling of an arylboronic acids with phenols (Chan et al., 1998;Evans et al., 1998;Lam et al. 1998).
There has been only one reported X-ray crystallographic study of the structure of a diethanolamine ester of a phenylboronic acid (1) (Rettig & Trotter, 1975 )]phenylboron) was measured on a diffractometer with Cu K a radiation and it was revealed to be non-centrosymmetric and in the P2 1 space group. The absolute configuration of the enatiomorphic crystal was determined in this study. In connection with our own work (Wang & Georghiou, 2002), crystals of (2), the corresponding diethanolamine ester of the 4-boronic acid derivative of methyl phenylacetate, were obtained and the structure of the molecule is reported here.

Refinement
H atoms were found in difference Fourier maps and subsequently placed in idealized positions with constrained distances and with U iso (H) values set to either 1.2Ueq or 1.5Ueq of the attached atom. They were refined on a riding model. All nonhydrogen atoms were refined anisotropically. This crystal was a weak anomalous scatterer collected with MoKa radiation, therefore, Friedel mates were merged (MERG 4) and absolute configuration was not determined. Fig. 1. The molecular structure of (2), with atom labels and 50% probability displacement ellipsoids for non-H atoms.   as those based on F, and R-factors based on ALL data will be even larger.

Figures
The crystal was a weak anomalous scatterer collected with Mo Kα radiation. Friedel mates were merged (MERG 4) and the absolute configuration was not determined.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq O1 1.00908 (