(4-Carbamoylphen­yl)boronic acid

Apostolova, M.D.; Nikolova, R.P.; Shivachev, B.L.

doi:10.1107/S1600536810014789

Volume 66
Part 6
Page o1273
June 2010

Received 15 February 2010
Accepted 22 April 2010
Online 8 May 2010

Key indicators
Single-crystal X-ray study
T = 290 K
Mean () = 0.000 Å
Disorder in main residue
R = 0.053
wR = 0.148
Data-to-parameter ratio = 14.4
Details

(4-Carbamoylphenyl)boronic acid

Margarita D. Apostolova,^a Rositsa P. Nikolova ^b and Boris L. Shivachev ^b ^*

^aInstitute of Molecular Biology "Acad. R. Tsanev", Bulgarian Academy of Sciences, Acad G. Bonchev Str. Building 21, 1113 Sofia, Bulgaria, and ^bCentral Laboratory of Mineralogy and Crystallography, Bulgarian Academy of Sciences, Acad G. Bonchev Str. Building 107, 1113 Sofia, Bulgaria
Correspondence e-mail: blshivachev@gmail.com

In the title compound, C₇H₈BNO₃, the molecule lies on an inversion center leading to a statistical disorder of the B(OH)₂ and CONH₂ groups. In the crystal structure, molecules are linked by N-HO and O-HO hydrogen bonds, forming sheets parallel to the bc plane. The B(OH)₂ and CONH₂ groups are twisted out of the mean plane of the benzene ring by 23.9 (5) and 24.6 (6)°, respectively.

Related literature

For general background to the use of boronic acids in organic synthesis, as pharmaceutical agents and in crystal engineering see: Miyaura & Suzuki (1995); Suzuki (1999); Adams & Kauffman (2004); Barth et al. (2005); Minkkilä et al. (2008); Maly et al. (2006); Desiraju (1995); James et al. (2006).. For related structures, see: Cobbledick & Small (1972); Rodríguez-Cuamatzi et al. (2004). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₇H₈BNO₃
M_r = 164.95
Triclinic, $[P \overline 1]$
a = 4.997 (2) Å
b = 5.351 (2) Å
c = 7.2967 (16) Å
= 103.912 (13)°
= 98.69 (2)°
= 93.136 (14)°
V = 186.36 (11) Å³
Z = 1
Mo K radiation
= 0.11 mm^-1
T = 290 K
0.27 × 0.25 × 0.25 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
2155 measured reflections
1078 independent reflections
755 reflections with I > 2(I)
R_int = 0.054
3 standard reflections every 120 min intensity decay: 2%

Refinement

R[F² > 2(F²)] = 0.053
wR(F²) = 0.148
S = 1.03
1078 reflections
75 parameters
88 restraints
H-atom parameters constrained
_max = 0.28 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O2ⁱ	0.82	1.96	2.77 (2)	167
O2-H2AO1ⁱⁱ	0.82	2.05	2.79 (2)	149
O2-H2AO3ⁱⁱⁱ	0.82	2.00	2.73 (2)	149
N1-H1AO3^iv	0.86	2.14	2.97 (3)	160.7
N1-H1BO1^v	0.86	2.30	2.97 (2)	135.7
N1-H1BO3^vi	0.86	2.18	2.90 (2)	140.8
Symmetry codes: (i) -x, -y-1, -z+1; (ii) x+1, y, z; (iii) -x+1, -y, -z; (iv) -x, -y+1, -z-1; (v) -x-1, -y, -z; (vi) x-1, y, z.

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Bruno et al., 2002); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2998 ).

Acknowledgements

The authors wish to acknowledge NSFB grants RNI09/01 and DOO2/305.

References

Adams, J. & Kauffman, M. (2004). Cancer Investig. 22, 304-311.
Barth, R. F., Coderre, J. A., Gra, M., Vicente, H. & Blue, T. E. (2005). Clin. Cancer Res. 11, 3987-4002.
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Cobbledick, R. E. & Small, R. W. H. (1972). Acta Cryst. B28, 2893-2896.
Desiraju, G. R. (1995). Angew. Chem. Int. Ed. 34, 2311-2327.
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Maly, K. E., Malek, N., Fournier, J.-H., Rodríguez-Cuamatzi, P., Maris, Th. & Wuest, J. D. (2006). Pure Appl. Chem. 78, 1305-1321.
Minkkilä, A., Saario, S. M., Käsnänen, H., Leppänen, J., Poso, A. & Nevalainen, T. (2008). J. Med. Chem. 51, 7057-7060.
Miyaura, N. & Suzuki, A. (1995). Chem. Rev. 95, 2457-2483.
Rodríguez-Cuamatzi, P., Vargas-Díaz, G., Maris, T., Wuest, J. D. & Höpfl, H. (2004). Acta Cryst. E60, o1316-o1318.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Suzuki, A. (1999). J. Organomet. Chem. 576, 147-168.

organic compounds