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. 2012 Aug 1;68(Pt 8):o2429-30.
doi: 10.1107/S1600536812029650. Epub 2012 Jul 10.

Methyl 2-(5,5-dimethyl-1,3,2-dioxa-borinan-2-yl)-4-nitro-benzoate

S F Jenkinson, A L Thompson, M I Simone

Methyl 2-(5,5-dimethyl-1,3,2-dioxa-borinan-2-yl)-4-nitro-benzoate

S F Jenkinson et al. Acta Crystallogr Sect E Struct Rep Online. .

Abstract

The six-membered boronate ester ring of the title compound, C(13)H(16)BNO(6), adopts an envelope conformation with the C atom bearing the dimethyl substituents at the flap. The O-B-C-C torsion angles between the boronate group and the benzene ring are 72.5 (2) and 81.0 (2)°. The 4-nitro-benzoate unit adopts a slightly twisted conformation, with dihedral angles between the benzene ring and the nitrate and methyl ester groups of 17.5 (2) and 14.4 (3)°, respectively. In the crystal, inversion-related pairs of mol-ecules show weak π-π stacking inter-actions [centroid-centroid distance = 4.0585 (9) Å and inter-planar spacing = 3.6254 (7) Å].

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Figures

Fig. 1.
Fig. 1.
The title compound with displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms are shown as spheres of arbitary radius.
Fig. 2.
Fig. 2.
Packing diagram of the title compound projected along the b-axis.
Fig. 3.
Fig. 3.
Synthesis of sterically hindered boronate ester 2 from the aryl bromide 1.
See this image and copyright information in PMC

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