3-Amino-phenyl-boronic acid monohydrate.

In the title compound, C(6)H(8)BNO(2)·H(2)O, the almost planar boronic acid mol-ecules (r.m.s. deviation = 0.044 Å) form inversion dimers, linked by pairs of O-H⋯O hydrogen bonds. The water mol-ecules link these dimers into [100] chains by way of O-H⋯O hydrogen bonds, and N-H⋯O links generate (100) sheets.

Related literature

For background to the synthesis, structures and applications of phenyl­boronic acid derivatives, see: Barba & Betanzos (2007 ▶); Barba et al. (2004 ▶, 2006 ▶); Bernstein et al. (1995 ▶); Christinat et al. (2008 ▶); Dreos et al. (2002 ▶); Fujita et al. (2008 ▶); Höpfl (2002 ▶); Hall (2005 ▶); Lulinski et al. (2007 ▶); Miyaura & Suzuki (1995 ▶); Severin (2009 ▶); Shinkai et al. (2001 ▶); Smith et al. (2008 ▶); Zhang et al. (2007 ▶).

Experimental

Crystal data

C6H8BNO2·H2O

M = 154.96

Monoclinic,

a = 7.1211 (8) Å

b = 13.8548 (15) Å

c = 7.8475 (8) Å

β = 100.663 (2)°

V = 760.88 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.44 × 0.38 × 0.34 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.89, T max = 1.00

7077 measured reflections

1341 independent reflections

1258 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.088

S = 1.03

1341 reflections

124 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.17 e Å−3

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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810015655/hb5409sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015655/hb5409Isup2.hkl

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

C6H8BNO2·H2O	F(000) = 328
Mr = 154.96	Dx = 1.353 Mg m−3
Monoclinic, P21/c	Melting point: 368 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.1211 (8) Å	Cell parameters from 4929 reflections
b = 13.8548 (15) Å	θ = 2.9–28.3°
c = 7.8475 (8) Å	µ = 0.11 mm−1
β = 100.663 (2)°	T = 100 K
V = 760.88 (14) Å3	Block, colourless
Z = 4	0.44 × 0.38 × 0.34 mm

Bruker SMART APEX CCD diffractometer	1341 independent reflections
Radiation source: fine-focus sealed tube	1258 reflections with I > 2σ(I)
graphite	Rint = 0.022
Detector resolution: 8.3 pixels mm-1	θmax = 25.0°, θmin = 2.9°
phi and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −16→16
Tmin = 0.89, Tmax = 1.00	l = −9→9
7077 measured reflections

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0487P)2 + 0.3165P] where P = (Fo2 + 2Fc2)/3
1341 reflections	(Δ/σ)max < 0.001
124 parameters	Δρmax = 0.29 e Å−3
6 restraints	Δρmin = −0.17 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
B1	0.5617 (2)	0.06346 (10)	0.24383 (18)	0.0160 (3)
N1	1.02034 (15)	0.15487 (8)	0.78329 (14)	0.0186 (3)
H1A	1.030 (2)	0.1547 (11)	0.8942 (3)	0.022 (4)*
H1B	1.0986 (18)	0.1138 (9)	0.753 (2)	0.029 (4)*
O1	0.71516 (12)	0.03223 (7)	0.17614 (11)	0.0180 (2)
H1'	0.682 (3)	0.0084 (12)	0.0767 (10)	0.038 (5)*
O2	0.38624 (12)	0.05950 (6)	0.13944 (11)	0.0179 (2)
H2'	0.2917 (15)	0.0828 (12)	0.175 (2)	0.036 (5)*
C1	0.60035 (17)	0.10356 (8)	0.43486 (16)	0.0151 (3)
C2	0.78720 (17)	0.10598 (8)	0.52950 (16)	0.0158 (3)
H2	0.8881	0.0809	0.4786	0.019*
C3	0.82923 (17)	0.14429 (8)	0.69650 (16)	0.0151 (3)
C4	0.68011 (18)	0.17961 (9)	0.77225 (16)	0.0171 (3)
H4	0.7062	0.2051	0.8866	0.021*
C5	0.49436 (18)	0.17741 (9)	0.68042 (16)	0.0181 (3)
H5	0.3935	0.2018	0.7322	0.022*
C6	0.45380 (17)	0.13999 (9)	0.51337 (16)	0.0163 (3)
H6	0.3257	0.1391	0.4519	0.020*
O31	0.05437 (12)	0.14588 (7)	0.17821 (12)	0.0199 (2)
H31A	0.048 (3)	0.2022 (5)	0.217 (2)	0.041 (5)*
H31B	−0.0485 (14)	0.1179 (12)	0.186 (2)	0.040 (5)*

	U11	U22	U33	U12	U13	U23
B1	0.0179 (7)	0.0120 (7)	0.0181 (7)	−0.0012 (5)	0.0037 (6)	0.0013 (5)
N1	0.0161 (6)	0.0235 (6)	0.0156 (6)	0.0018 (4)	0.0016 (4)	−0.0009 (4)
O1	0.0155 (5)	0.0228 (5)	0.0152 (5)	0.0002 (4)	0.0017 (3)	−0.0049 (4)
O2	0.0143 (5)	0.0221 (5)	0.0172 (5)	0.0019 (4)	0.0026 (4)	−0.0047 (4)
C1	0.0174 (6)	0.0110 (6)	0.0171 (6)	−0.0019 (5)	0.0034 (5)	0.0016 (5)
C2	0.0167 (6)	0.0137 (6)	0.0179 (6)	0.0010 (5)	0.0058 (5)	0.0014 (5)
C3	0.0164 (6)	0.0126 (6)	0.0158 (6)	−0.0008 (5)	0.0019 (5)	0.0030 (5)
C4	0.0206 (7)	0.0153 (6)	0.0156 (6)	−0.0012 (5)	0.0038 (5)	−0.0013 (5)
C5	0.0177 (6)	0.0159 (6)	0.0219 (7)	0.0011 (5)	0.0072 (5)	−0.0007 (5)
C6	0.0135 (6)	0.0157 (6)	0.0190 (6)	−0.0015 (5)	0.0013 (5)	0.0004 (5)
O31	0.0154 (5)	0.0228 (5)	0.0219 (5)	0.0007 (4)	0.0045 (4)	−0.0031 (4)

B1—O2	1.3623 (17)	C2—C3	1.3941 (18)
B1—O1	1.3707 (17)	C2—H2	0.9500
B1—C1	1.5745 (18)	C3—C4	1.3980 (18)
N1—C3	1.4122 (16)	C4—C5	1.3846 (18)
N1—H1A	0.860 (3)	C4—H4	0.9500
N1—H1B	0.860 (13)	C5—C6	1.3894 (18)
O1—H1'	0.840 (10)	C5—H5	0.9500
O2—H2'	0.840 (13)	C6—H6	0.9500
C1—C2	1.3991 (17)	O31—H31A	0.842 (9)
C1—C6	1.4005 (18)	O31—H31B	0.841 (12)
O2—B1—O1	117.55 (11)	C2—C3—C4	119.02 (11)
O2—B1—C1	124.48 (11)	C2—C3—N1	120.86 (11)
O1—B1—C1	117.95 (11)	C4—C3—N1	119.91 (11)
C3—N1—H1A	112.3 (11)	C5—C4—C3	119.91 (11)
C3—N1—H1B	114.4 (11)	C5—C4—H4	120.0
H1A—N1—H1B	109.9 (15)	C3—C4—H4	120.0
B1—O1—H1'	112.2 (13)	C4—C5—C6	120.73 (11)
B1—O2—H2'	119.1 (12)	C4—C5—H5	119.6
C2—C1—C6	118.08 (11)	C6—C5—H5	119.6
C2—C1—B1	119.71 (11)	C5—C6—C1	120.52 (11)
C6—C1—B1	122.19 (11)	C5—C6—H6	119.7
C3—C2—C1	121.72 (11)	C1—C6—H6	119.7
C3—C2—H2	119.1	H31A—O31—H31B	107.4 (18)
C1—C2—H2	119.1
O2—B1—C1—C2	−178.77 (11)	C1—C2—C3—N1	−173.67 (11)
O1—B1—C1—C2	−0.23 (17)	C2—C3—C4—C5	−0.90 (18)
O2—B1—C1—C6	−0.64 (19)	N1—C3—C4—C5	173.96 (11)
O1—B1—C1—C6	177.90 (11)	C3—C4—C5—C6	0.28 (18)
C6—C1—C2—C3	−0.73 (18)	C4—C5—C6—C1	0.13 (18)
B1—C1—C2—C3	177.47 (11)	C2—C1—C6—C5	0.08 (18)
C1—C2—C3—C4	1.14 (18)	B1—C1—C6—C5	−178.07 (11)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1'···O2i	0.84 (1)	1.92 (1)	2.7583 (13)	174 (2)
N1—H1A···O31ii	0.86 (1)	2.21 (1)	3.0661 (15)	177 (1)
N1—H1B···O1iii	0.86 (1)	2.43 (1)	3.1854 (15)	147 (1)
O2—H2'···O31	0.84 (1)	1.91 (1)	2.7159 (13)	161 (2)
O31—H31A···N1iv	0.84 (1)	2.07 (1)	2.9040 (15)	173 (2)
O31—H31B···O1v	0.84 (1)	2.05 (1)	2.8810 (13)	170 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1′⋯O2i	0.84 (1)	1.92 (1)	2.7583 (13)	174 (2)
N1—H1A⋯O31ii	0.86 (1)	2.21 (1)	3.0661 (15)	177 (1)
N1—H1B⋯O1iii	0.86 (1)	2.43 (1)	3.1854 (15)	147 (1)
O2—H2′⋯O31	0.84 (1)	1.91 (1)	2.7159 (13)	161 (2)
O31—H31A⋯N1iv	0.84 (1)	2.07 (1)	2.9040 (15)	173 (2)
O31—H31B⋯O1v	0.84 (1)	2.05 (1)	2.8810 (13)	170 (2)

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