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. 2012 Jan;68(Pt 1):o84.
doi: 10.1107/S1600536811052470. Epub 2011 Dec 10.

9-[(E)-2-(4,4,5,5-Tetra-methyl-1,3,2-dioxa-borolan-2-yl)ethen-yl]-9H-carbazole

Yuki Hatayama  1 , Tsunehisa Okuno
Affiliations

9-[(E)-2-(4,4,5,5-Tetra-methyl-1,3,2-dioxa-borolan-2-yl)ethen-yl]-9H-carbazole

Yuki Hatayama et al. Acta Crystallogr Sect E Struct Rep Online. 2012 Jan.

Abstract

The title compound, C(20)H(22)BNO(2), is a simple olefinic compound which carries both B and N atoms that are trans to one another. The π-conjugated system of the compound is considered to be isoelectronic with 1,3-butadiene. There are two independent mol-ecules in the asymmetric unit in which the environments around the boron atoms are essentially planar (r.m.s. deviations of 0.0032 and 0.0021 Å for the BO(2)C planes). The dihedral angles of the olefinic planes with the boron planes are 5.70 (11) and 9.74 (9)°, respectively, while the dihedral angles of the olefinic planes with the carbazole planes are 19.37 (3) and 10.74 (6)°. These dihedral angles are consistent with those in 9-ethenylcarbazole and an ethenylboronic ester derivative. The N-Csp(2), B-Csp(2) and C=C bond lengths suggest that the contribution of the canonical structure can be described as N(+)=C-C=B(-).

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Figures

Fig. 1.
Fig. 1.
The asymmetric unit of the title compound with atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres.
See this image and copyright information in PMC

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