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Volume 68 
Part 11 
Page o3103  
November 2012  

Received 29 August 2012
Accepted 5 October 2012
Online 13 October 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.034
wR = 0.092
Data-to-parameter ratio = 16.5
Details
Open access

(3aS,4S,6S,7aR)-Hexahydro-3a,5,5-trimethyl-2-phenyl-4,6-methano-1,3,2-benzodioxaborole

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: tore.lejon@uit.no

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...[pi](Ph) interactions occur.

Related literature

For the Matteson homologation reaction, see: Matteson et al. (1983[Matteson, D. S., Ray, R., Rocks, R. R. & Tsai, D. J. S. (1983). Organometallics, 2, 1536-1543.]); Matteson (1989[Matteson, D. S. (1989). Chem. Rev. 89, 1535-1551.]). For 2-substituted (+)-pinanediolboronates, see: Carmès et al. (2000)[Carmès, L., Carreaux, F. & Carboni, B. (2000). J. Org. Chem. 65, 5403-5408.]; Caselli et al. (2003[Caselli, E., Danieli, C., Morandi, S., Bonfiglio, B., Forni, A. & Prati, F. (2003). Org. Lett. 5, 4863-4866.]); Morandi et al. (2003[Morandi, F., Caselli, E., Morandi, S., Focia, P. J., Blásquez, J., Shoichet, B. K. & Prati, F. (2003). J. Am. Chem. Soc. 125, 685-695.], 2005[Morandi, S., Caselli, E., Forni, A., Bucciarelli, M., Torre, G. & Prati, F. (2005). Tetrahedron Asymmetry, 16, 2918-2926.]).

[Scheme 1]

Experimental

Crystal data
  • C16H21BO2

  • Mr = 256.14

  • Orthorhombic, P 21 21 21

  • a = 8.4974 (3) Å

  • b = 11.8566 (4) Å

  • c = 13.9580 (4) Å

  • V = 1406.27 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 100 K

  • 0.25 × 0.22 × 0.18 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.981, Tmax = 0.986

  • 21778 measured reflections

  • 2905 independent reflections

  • 2717 reflections with I > 2[sigma](I)

  • Rint = 0.037

Refinement
  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.092

  • S = 1.05

  • 2905 reflections

  • 176 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C12-C17 phenyl ring

D-H...A D-H H...A D...A D-H...A
C8-H8A...Cgi 0.99 2.94 3.7532 (13) 140
C11-H11A...Cgii 0.98 2.97 3.9481 (13) 174
Symmetry codes: (i) x-1, y, z; (ii) [-x+{\script{1\over 2}}, -y+1, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2. Bruker AXS, Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2001[Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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 ).


Acknowledgements

The Norwegian Research Council is acknowledged for research grant 166742.

References

Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). APEX2. Bruker AXS, Madison, Wisconsin, USA.
Carmès, L., Carreaux, F. & Carboni, B. (2000). J. Org. Chem. 65, 5403-5408.  [PubMed]
Caselli, E., Danieli, C., Morandi, S., Bonfiglio, B., Forni, A. & Prati, F. (2003). Org. Lett. 5, 4863-4866.  [ISI] [CrossRef] [PubMed] [ChemPort]
Matteson, D. S. (1989). Chem. Rev. 89, 1535-1551.  [CrossRef] [ChemPort] [ISI]
Matteson, D. S., Ray, R., Rocks, R. R. & Tsai, D. J. S. (1983). Organometallics, 2, 1536-1543.  [CrossRef] [ChemPort]
Morandi, S., Caselli, E., Forni, A., Bucciarelli, M., Torre, G. & Prati, F. (2005). Tetrahedron Asymmetry, 16, 2918-2926.  [ISI] [CrossRef] [ChemPort]
Morandi, F., Caselli, E., Morandi, S., Focia, P. J., Blásquez, J., Shoichet, B. K. & Prati, F. (2003). J. Am. Chem. Soc. 125, 685-695.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3103  [ doi:10.1107/S1600536812041712 ]

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