(2,4,6-Trimethyl­phen­yl)boronic acid–triphenyl­phosphine oxide (1/1)

Roşca, S.; Olaru, M.; Raţ, C.I.

doi:10.1107/S1600536811051609

Volume 68
Part 1
Page o31
January 2012

Received 20 November 2011
Accepted 30 November 2011
Online 7 December 2011

Key indicators
Single-crystal X-ray study
T = 297 K
Mean (C-C) = 0.006 Å
R = 0.083
wR = 0.186
Data-to-parameter ratio = 15.3
Details

(2,4,6-Trimethylphenyl)boronic acid-triphenylphosphine oxide (1/1)

Sorin Rosca,^a Marian Olaru ^a and Ciprian I. Rat ^a ^*

^aUniversitatea Babes-Bolyai, Facultatea de Chimie si Inginerie Chimicã, 11 Arany Janos, 400028 Cluj-Napoca, Romania
Correspondence e-mail: ciprian.rat@ubbcluj.ro

In the crystal structure of the title compound, C₉H₁₃BO₂·C₁₈H₁₅OP, there are O-HO hydrogen bonds between the O atom of triphenylphosphine oxide and one hydroxy group of the boronic acid. Boronic acid molecules form inversion-related hydrogen-bonded dimers in an R₂²(8) motif. The structure is consolidated by intermolecular C-HO bonds and C-H [pi] interactions.

Related literature

For applications of boronic acids, see: Suzuki (2011); Yang et al. (2011); Furukawa & Yaghi (2009). For recently reported structures of triphenylphosphine oxide and triphenylphosphine oxide hemihydrate, see: Sivaramkrishna et al. (2007); Ng (2009). For structures of related boronic acids, see: Filthaus et al. (2008), Cyranski et al. (2008); Rettig & Trotter (1977).

Experimental

Crystal data

C₉H₁₃BO₂·C₁₈H₁₅OP
M_r = 442.27
Monoclinic, P 2₁ /c
a = 12.218 (4) Å
b = 12.339 (4) Å
c = 16.983 (5) Å
= 95.651 (5)°
V = 2548.0 (14) Å³
Z = 4
Mo K radiation
= 0.13 mm^-1
T = 297 K
0.52 × 0.45 × 0.42 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000) T_min = 0.934, T_max = 0.947
23787 measured reflections
4486 independent reflections
3727 reflections with I > 2(I)
R_int = 0.052

Refinement

R[F² > 2(F²)] = 0.083
wR(F²) = 0.186
S = 1.19
4486 reflections
294 parameters
H-atom parameters constrained
_max = 0.40 e Å^-3
_min = -0.32 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C19-C24 benzene ring.

D-HA	D-H	HA	DA	D-HA
O2-H2AO1	0.82	1.84	2.645 (3)	168
O3-H3AO2ⁱ	0.82	1.99	2.795 (4)	169
C4-H4O1ⁱⁱ	0.93	2.41	3.326 (4)	167
C6-H6Cg4	0.93	2.88	3.728 (4)	152
C15-H15Cg4ⁱⁱⁱ	0.93	2.69	3.602 (5)	168
Symmetry codes: (i) -x+1, -y, -z; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) x+1, y, z.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2009); software used to prepare material for publication: publCIF (Westrip, 2010) and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2368 ).

Acknowledgements

This work was supported by the National University Research Council (CNCS) of Romania (project TE295/2010). We thank Dr Albert Soran for the crystallographic measurements and data refinement.

References

Brandenburg, K. (2009). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2000). SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2001). SAINT-Plus. 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.
Filthaus, M., Oppel, I. M. & Bettinger, H. F. (2008). Org. Biomol. Chem. 6, 1201-1207.
Furukawa, H. & Yaghi, O. M. (2009). J. Am. Chem. Soc. 131, 8875-8883.
Ng, S. W. (2009). Acta Cryst. E65, o1431.
Rettig, S. J. & Trotter, J. (1977). Can. J. Chem. 55, 3071-3075.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sivaramkrishna, A., Su, H. & Moss, J. R. (2007). Private communication (refcode TPEPHO13). CCDC, Cambridge, England.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Suzuki, A. (2011). Angew. Chem. Int. Ed. 50, 6722-6737.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.
Yang, X., Chen, Y., Jin, S. & Binghe, W. (2011). Artificial Receptors for Chemical Sensors, edited by V. Mirsky & A. Yatsimirsky, pp. 169-190. Weinheim: Wiley-VCH.

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