(4-Carbamoylphen-yl)boronic acid.

In the title compound, C(7)H(8)BNO(3), the mol-ecule lies on an inversion center leading to a statistical disorder of the B(OH)(2) and CONH(2) groups. In the crystal structure, mol-ecules are linked by N-H⋯O and O-H⋯O hydrogen bonds, forming sheets parallel to the bc plane. The B(OH)(2) and CONH(2) 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 = 164.95

Triclinic,

a = 4.997 (2) Å

b = 5.351 (2) Å

c = 7.2967 (16) Å

α = 103.912 (13)°

β = 98.69 (2)°

γ = 93.136 (14)°

V = 186.36 (11) Å3

Z = 1

Mo Kα radiation

μ = 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 > 2σ(I)

R int = 0.054

3 standard reflections every 120 min intensity decay: 2%

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.148

S = 1.03

1078 reflections

75 parameters

88 restraints

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.23 e Å−3

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 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810014789/lh2998sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014789/lh2998Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C7H8BNO3	Z = 1
Mr = 164.95	F(000) = 86
Triclinic, P1	Dx = 1.470 Mg m−3
Hall symbol: -P 1	Melting point: not measured K
a = 4.997 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 5.351 (2) Å	Cell parameters from 22 reflections
c = 7.2967 (16) Å	θ = 18.0–19.8°
α = 103.912 (13)°	µ = 0.11 mm−1
β = 98.69 (2)°	T = 290 K
γ = 93.136 (14)°	Prismatic, colorless
V = 186.36 (11) Å3	0.27 × 0.25 × 0.25 mm

Enraf–Nonius CAD-4 diffractometer	Rint = 0.054
Radiation source: fine-focus sealed tube	θmax = 30.0°, θmin = 2.9°
graphite	h = −7→7
Non–profiled ω/2θ scans	k = −7→7
2155 measured reflections	l = −10→10
1078 independent reflections	3 standard reflections every 120 min
755 reflections with I > 2σ(I)	intensity decay: 2%

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0786P)2 + 0.0033P] where P = (Fo2 + 2Fc2)/3
1078 reflections	(Δ/σ)max = 0.001
75 parameters	Δρmax = 0.28 e Å−3
88 restraints	Δρmin = −0.23 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq	Occ. (<1)
B1	−0.001 (3)	−0.298 (2)	0.2892 (18)	0.0268 (10)	0.50
O1	−0.243 (3)	−0.393 (3)	0.318 (3)	0.0399 (19)	0.50
H1	−0.2184	−0.4584	0.4092	0.060*	0.50
O2	0.236 (2)	−0.334 (2)	0.404 (2)	0.0351 (15)	0.50
H2A	0.3669	−0.3158	0.3510	0.053*	0.50
C1	0.0096 (17)	0.113 (2)	−0.1593 (16)	0.0246 (10)	0.50
C2	−0.2061 (18)	−0.068 (2)	−0.1647 (17)	0.0314 (10)	0.50
H2	−0.3512	−0.1021	−0.2661	0.038*	0.50
C3	−0.207 (2)	−0.197 (2)	−0.0217 (17)	0.0314 (10)	0.50
H3	−0.3529	−0.3166	−0.0282	0.038*	0.50
C4	0.0069 (18)	−0.150 (2)	0.1318 (16)	0.0246 (10)	0.50
C5	0.2219 (19)	0.029 (2)	0.1375 (17)	0.0314 (10)	0.50
H5	0.3670	0.0634	0.2389	0.038*	0.50
C6	0.223 (2)	0.158 (2)	−0.0057 (17)	0.0314 (10)	0.50
H6	0.3685	0.2776	0.0010	0.038*	0.50
C7	0.016 (2)	0.256 (2)	−0.3128 (15)	0.0268 (10)	0.50
O3	0.237 (3)	0.341 (3)	−0.344 (3)	0.0399 (19)	0.50
N1	−0.212 (3)	0.283 (3)	−0.415 (3)	0.0351 (15)	0.50
H1A	−0.2112	0.3606	−0.5051	0.042*	0.50
H1B	−0.3631	0.2237	−0.3916	0.042*	0.50

	U11	U22	U33	U12	U13	U23
B1	0.0340 (13)	0.027 (3)	0.024 (2)	0.0062 (15)	0.0098 (12)	0.011 (2)
O1	0.0295 (7)	0.054 (5)	0.048 (4)	0.002 (2)	0.0081 (18)	0.035 (4)
O2	0.0282 (18)	0.046 (4)	0.0412 (16)	0.006 (2)	0.0081 (15)	0.029 (3)
C1	0.0301 (11)	0.028 (3)	0.020 (3)	0.0076 (11)	0.0089 (11)	0.0097 (19)
C2	0.0331 (11)	0.038 (3)	0.024 (3)	−0.0005 (12)	−0.0004 (12)	0.0137 (19)
C3	0.0329 (11)	0.034 (3)	0.030 (3)	−0.0018 (12)	0.0048 (12)	0.015 (2)
C4	0.0301 (11)	0.028 (3)	0.020 (3)	0.0076 (11)	0.0089 (11)	0.0097 (19)
C5	0.0331 (11)	0.038 (3)	0.024 (3)	−0.0005 (12)	−0.0004 (12)	0.0137 (19)
C6	0.0329 (11)	0.034 (3)	0.030 (3)	−0.0018 (12)	0.0048 (12)	0.015 (2)
C7	0.0340 (13)	0.027 (3)	0.024 (2)	0.0062 (15)	0.0098 (12)	0.011 (2)
O3	0.0295 (7)	0.054 (5)	0.048 (4)	0.002 (2)	0.0081 (18)	0.035 (4)
N1	0.0282 (18)	0.046 (4)	0.0412 (16)	0.006 (2)	0.0081 (15)	0.029 (3)

B1—O1	1.351 (8)	C3—C4	1.391 (8)
B1—O2	1.393 (8)	C3—H3	0.9300
B1—C4	1.546 (6)	C4—C5	1.391 (8)
O1—H1	0.8200	C5—C6	1.384 (8)
O2—H2A	0.8200	C5—H5	0.9300
C1—C6	1.388 (8)	C6—H6	0.9300
C1—C2	1.397 (8)	C7—O3	1.246 (7)
C1—C7	1.505 (6)	C7—N1	1.298 (7)
C2—C3	1.384 (8)	N1—H1A	0.8600
C2—H2	0.9300	N1—H1B	0.8600
O1—B1—O2	118.9 (15)	C5—C4—B1	122.2 (8)
O1—B1—C4	119.4 (13)	C6—C5—C4	120.8 (5)
O2—B1—C4	121.6 (12)	C6—C5—H5	119.6
C6—C1—C2	117.8 (5)	C4—C5—H5	119.6
C6—C1—C7	120.0 (7)	C5—C6—C1	121.2 (6)
C2—C1—C7	122.2 (7)	C5—C6—H6	119.4
C3—C2—C1	121.1 (5)	C1—C6—H6	119.4
C3—C2—H2	119.5	O3—C7—N1	120.8 (16)
C1—C2—H2	119.5	O3—C7—C1	120.4 (13)
C2—C3—C4	120.8 (5)	N1—C7—C1	118.8 (13)
C2—C3—H3	119.6	C7—N1—H1A	120.0
C4—C3—H3	119.6	C7—N1—H1B	120.0
C3—C4—C5	118.2 (5)	H1A—N1—H1B	120.0
C3—C4—B1	119.5 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.82	1.96	2.77 (2)	167
O2—H2A···O1ii	0.82	2.05	2.79 (2)	149
O2—H2A···O3iii	0.82	2.00	2.73 (2)	149
N1—H1A···O3iv	0.86	2.14	2.97 (3)	160.7
N1—H1B···O1v	0.86	2.30	2.97 (2)	135.7
N1—H1B···O3vi	0.86	2.18	2.90 (2)	140.8

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.82	1.96	2.77 (2)	167
O2—H2A⋯O1ii	0.82	2.05	2.79 (2)	149
O2—H2A⋯O3iii	0.82	2.00	2.73 (2)	149
N1—H1A⋯O3iv	0.86	2.14	2.97 (3)	160.7
N1—H1B⋯O1v	0.86	2.30	2.97 (2)	135.7
N1—H1B⋯O3vi	0.86	2.18	2.90 (2)	140.8

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .