Received 29 August 2012
aDepartment of Chemistry, Faculty of Science and Technology, University of Tromsø, N-9037 Tromsø, Norway, and bX-ray Structural Centre, A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street B-334, Moscow 119991, Russian Federation
Correspondence e-mail: firstname.lastname@example.org
The molecule of the title compound, C16H21BO2, comprises a chiral fused tricyclic system containing five-membered (1,3,2-dioxaborolane), six-membered (cyclohexane) and four-membered (cyclobutane) rings. The 1,3,2-dioxaborolane ring is almost planar (r.m.s. deviation = 0.035 Å), and the syn H and Me substituents at this ring are in an eclipsed conformation. The cyclohexane and cyclobutane rings adopt sofa and butterfly conformations, respectively. The B atom has a trigonal-planar configuration (sum of the bond angles = 360.0°). The phenyl ring is practically coplanar with the 1,3,2-dioxaborolane ring [dihedral angle between the ring planes = 1.96 (8)°]. The absolute structure was determined from the known configuration of (+)-pinanediol which was used in the synthesis. In the crystal, weak C-H(Ph) interactions occur.
For the Matteson homologation reaction, see: Matteson et al. (1983); Matteson (1989). For 2-substituted (+)-pinanediolboronates, see: Carmès et al. (2000); Caselli et al. (2003); Morandi et al. (2003, 2005).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FB2267 ).
The Norwegian Research Council is acknowledged for research grant 166742.
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