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Volume 69 
Part 12 
Page o1818  
December 2013  

Received 12 November 2013
Accepted 20 November 2013
Online 23 November 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.034
wR = 0.097
Data-to-parameter ratio = 21.6
Details
Open access

2-Meth­oxy-3-(tri­methyl­sil­yl)phenyl­boronic acid

aPhysical Chemistry Department, Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland
Correspondence e-mail: serek@ch.pw.edu.pl

The mol­ecular structure of the title compound, C10H17BO3Si, features an intra­molecular O-H...O hydrogen bond; the boronic group group has an exo-endo conformation. In the crystal, the mol­ecules inter­act with each other by O-H...O hydrogen bonds, producing centrosymmetric dimers that are linked by weak [pi]-[pi] stacking inter­actions featuring specific short B...C contacts [e.g. 3.372 (2) Å], forming an infinite columnar structure aligned along the a-axis direction.

Related literature

For structures of related ortho-alk­oxy aryl­boronic acids, see: Cyranski et al. (2012[Cyranski, M. K., Klimentowska, P., Rydzewska, A., Serwatowski, J., Sporzynski, A. & Stepien, D. K. (2012). CrystEngComm, 14, 6282-6294.]). For binding energies of other boronic acid dimers, see: Cyranski et al. (2008[Cyranski, M. K., Jezierska, A., Klimentowska, P., Panek, J. J. & Sporzynski, A. (2008). J. Phys. Org. Chem. 21, 472-482.]); Durka et al. (2012[Durka, K., Jarzembska, K. N., Kaminski, R., Lulinski, S., Serwatowski, J. & Wozniak, K. (2012). Cryst. Growth Des. 12, 3720-3734.]). For the PIXEL program, see Gavezzotti (2003[Gavezzotti, A. (2003). CrystEngComm, 5, 429-438.]). For the synthesis, see: Durka et al. (2010[Durka, K., Górka, J., Kurach, P., Lulinski, S. & Serwatowski, J. (2010). J. Organomet. Chem. 695, 2635-2643.]).

[Scheme 1]

Experimental

Crystal data
  • C10H17BO3Si

  • Mr = 224.14

  • Monoclinic, P 21 /n

  • a = 9.1832 (11) Å

  • b = 9.7082 (10) Å

  • c = 14.1415 (16) Å

  • [beta] = 104.26 (1)°

  • V = 1221.9 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.18 mm-1

  • T = 100 K

  • 0.16 × 0.12 × 0.10 mm

Data collection
  • Bruker APEXII diffractometer

  • Absorption correction: multi-scan (Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.744, Tmax = 0.780

  • 11175 measured reflections

  • 2939 independent reflections

  • 2154 reflections with I > 2[sigma](I)

  • Rint = 0.029

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

  • wR(F2) = 0.097

  • S = 1.02

  • 2939 reflections

  • 136 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.36 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2...O1 0.84 2.04 2.7532 (14) 142
O3-H3...O2i 0.84 1.97 2.8051 (14) 175
Symmetry code: (i) -x+2, -y+2, -z.

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and SORTAV (Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg, 2005[Brandenburg, K. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5273 ).


Acknowledgements

The X-ray measurements were undertaken in the Crystallographic Unit of the Physical Chemistry Laboratory at the Chemistry Department of the University of Warsaw. This work was supported by the Warsaw University of Technology. The support by Aldrich Chemical Co., Milwaukee, WI, USA, through continuous donation of chemicals and equipment is gratefully acknowledged.

References

Blessing, R. H. (1995). Acta Cryst. A51, 33-38.  [CrossRef] [IUCr Journals]
Brandenburg, K. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cyranski, M. K., Jezierska, A., Klimentowska, P., Panek, J. J. & Sporzynski, A. (2008). J. Phys. Org. Chem. 21, 472-482.
Cyranski, M. K., Klimentowska, P., Rydzewska, A., Serwatowski, J., Sporzynski, A. & Stepien, D. K. (2012). CrystEngComm, 14, 6282-6294.
Durka, K., Górka, J., Kurach, P., Lulinski, S. & Serwatowski, J. (2010). J. Organomet. Chem. 695, 2635-2643.  [CSD] [CrossRef] [ChemPort]
Durka, K., Jarzembska, K. N., Kaminski, R., Lulinski, S., Serwatowski, J. & Wozniak, K. (2012). Cryst. Growth Des. 12, 3720-3734.  [CSD] [CrossRef] [ChemPort]
Gavezzotti, A. (2003). CrystEngComm, 5, 429-438.  [Web of Science] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1818  [ doi:10.1107/S1600536813031656 ]

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