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Volume 69 
Part 9 
Page o1403  
September 2013  

Received 29 July 2013
Accepted 3 August 2013
Online 10 August 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.002 Å
R = 0.050
wR = 0.128
Data-to-parameter ratio = 20.0
Details
Open access

(E)-2-(1,1-Dicyclohexyl-3-phenylallyl)-5,5-dimethyl-1,3,2-dioxaborinane

aDepartment of Optometry, College of Applied Medical Sciences, King Saud University, PO Box 10219, Riyadh 11433, Saudi Arabia, and bSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, Wales
Correspondence e-mail: gelhiti@ksu.edu.sa, kariukib@cardiff.ac.uk

The crystal structure of the title compound, C26H39BO2, which contains no strong hydrogen bond donors, displays only long C-H...O contacts between inversion-related pairs of molecules. The structure contains layers rich in oxygen and boron parallel to the ac plane. The dioxaborinane ring adopts an envelope conformation with the C atom attached to the two methyl groups as the flap .

Related literature

For the synthesis and applications of allylboronic esters, see: Lombardo et al. (2002[Lombardo, M., Morganti, S., Tozzi, M. & Trombini, C. (2002). Eur. J. Org. Chem. pp. 2823-2830.]); Carosi & Hall (2007[Carosi, L. & Hall, D. G. (2007). Angew. Chem. Int. Ed. 46, 5913-5915.]); Althaus et al. (2010[Althaus, M., Mahmood, A., Suárez, J. R., Thomas, S. P. & Aggarwal, V. K. (2010). J. Am. Chem. Soc. 132, 4025-4028.]); Fandrick et al. (2010[Fandrick, K. R., Fandrick, D. R., Gao, J. J., Reeves, J. T., Tan, Z., Li, W., Song, J. J., Lu, B., Yee, N. K. & Senanayake, C. H. (2010). Org. Lett. 12, 3748-3751.]); Clary et al. (2011[Clary, J. W., Rettenmaier, T. J., Snelling, R., Bryks, W., Banwell, J., Wipke, W. T. & Singaram, B. (2011). J. Org. Chem. 76, 9602-9610.]); Hesse et al. (2012[Hesse, M. J., Butts, C. P., Willis, C. L. & Aggarwal, V. K. (2012). Angew. Chem. Int. Ed. 51, 12444-12448.]); Incerti-Pradillos et al. (2013[Incerti-Pradillos, C. A., Kabeshov, M. A. & Malkov, A. V. (2013). Angew. Chem. Int. Ed. 52, 5338-5341.]). For the X-ray structure of a boronic ester, see: Sopková-de Oliveira Santos et al. (2003[Sopková-de Oliveira Santos, J., Lancelot, J.-C., Bouillon, A. & Rault, S. (2003). Acta Cryst. C59, o111-o113.]).

[Scheme 1]

Experimental

Crystal data
  • C26H39BO2

  • Mr = 394.38

  • Triclinic, [P \overline 1]

  • a = 9.4967 (3) Å

  • b = 11.2837 (2) Å

  • c = 12.0297 (4) Å

  • [alpha] = 109.897 (2)°

  • [beta] = 96.388 (2)°

  • [gamma] = 102.048 (2)°

  • V = 1161.90 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 150 K

  • 0.38 × 0.30 × 0.28 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) Tmin = 0.975, Tmax = 0.981

  • 8277 measured reflections

  • 5287 independent reflections

  • 4303 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.128

  • S = 1.03

  • 5287 reflections

  • 264 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C22-H22B...O2i 0.99 2.69 3.5773 (18) 150
Symmetry code: (i) -x+1, -y, -z.

Data collection: COLLECT (Nonius, 2000[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994)[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]; program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP99 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and CHEMDRAW Ultra (Cambridge Soft, 2001[Cambridge Soft (2001). CHEMDRAW Ultra. Cambridge Soft Corporation, Cambridge, Massachusetts, USA.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GO2094 ).


Acknowledgements

The authors would like to extend their appreciation to the Deanship of Scientific Research at King Saud University for its funding for this research through the research group project RGP-VPP-239.

References

Althaus, M., Mahmood, A., Suárez, J. R., Thomas, S. P. & Aggarwal, V. K. (2010). J. Am. Chem. Soc. 132, 4025-4028.  [ISI] [CrossRef] [ChemPort] [PubMed]
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  [CrossRef] [details]
Cambridge Soft (2001). CHEMDRAW Ultra. Cambridge Soft Corporation, Cambridge, Massachusetts, USA.
Carosi, L. & Hall, D. G. (2007). Angew. Chem. Int. Ed. 46, 5913-5915.  [ISI] [CrossRef] [ChemPort]
Clary, J. W., Rettenmaier, T. J., Snelling, R., Bryks, W., Banwell, J., Wipke, W. T. & Singaram, B. (2011). J. Org. Chem. 76, 9602-9610.  [CSD] [CrossRef] [ChemPort] [PubMed]
Fandrick, K. R., Fandrick, D. R., Gao, J. J., Reeves, J. T., Tan, Z., Li, W., Song, J. J., Lu, B., Yee, N. K. & Senanayake, C. H. (2010). Org. Lett. 12, 3748-3751.  [ISI] [CrossRef] [ChemPort] [PubMed]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Hesse, M. J., Butts, C. P., Willis, C. L. & Aggarwal, V. K. (2012). Angew. Chem. Int. Ed. 51, 12444-12448.  [ISI] [CrossRef] [ChemPort]
Incerti-Pradillos, C. A., Kabeshov, M. A. & Malkov, A. V. (2013). Angew. Chem. Int. Ed. 52, 5338-5341.  [ChemPort]
Lombardo, M., Morganti, S., Tozzi, M. & Trombini, C. (2002). Eur. J. Org. Chem. pp. 2823-2830.  [CrossRef]
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Sopková-de Oliveira Santos, J., Lancelot, J.-C., Bouillon, A. & Rault, S. (2003). Acta Cryst. C59, o111-o113.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o1403  [ doi:10.1107/S1600536813021739 ]

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