3-Carb-oxy-2-methoxy-phenyl-boronic acid.

The mol-ecular structure of the title compound, 3-COOH-2-CH(3)O-C(6)H(3)B(OH)(2) or C(8)H(9)BO(5), is stabilized in part due to the presence of an intra-molecular O-H⋯O hydrogen bond. In the crystal structure, mol-ecules are linked by inter-molecular O-H⋯O hydrogen bonds, generating a two-dimensional sheet structure aligned parallel to the (11) plane.

Related literature

For structures of other carboxy­phenyl­boronic acids, see: SeethaLekshmi & Pedireddi (2007 ▶); Soundararajan et al. (1993 ▶). For the application of carboxy­phenyl­boronic acids in crystal engineering, see: (Aakeröy et al., 2005 ▶; SeethaLekshmi & Pedireddi, 2006 ▶). For structural characterization of related ortho-alk­oxy aryl­boronic acids, see: Dabrowski et al. (2006 ▶); Dąbrowski et al. (2008 ▶); Yang et al. (2005 ▶). For the synthesis of the title compound, see: (Kurach et al., 2008 ▶).

Experimental

Crystal data

C8H9BO5

M = 195.96

Triclinic,

a = 4.8451 (5) Å

b = 7.7564 (7) Å

c = 12.1064 (9) Å

α = 79.476 (7)°

β = 79.575 (7)°

γ = 76.125 (8)°

V = 429.75 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 100 (2) K

0.32 × 0.20 × 0.14 mm

Data collection

Kuma KM4 CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction 2005 ▶) T min = 0.95, T max = 0.98

12229 measured reflections

2106 independent reflections

1526 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.101

S = 1.05

2106 reflections

163 parameters

All H-atom parameters refined

Δρmax = 0.35 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction (2005 ▶); cell refinement: CrysAlis RED (Oxford Diffraction (2005 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I. DOI: 10.1107/S1600536808029504/tk2303sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029504/tk2303Isup2.hkl

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

C8H9BO5	V = 429.75 (7) Å3
Mr = 195.96	Z = 2
Triclinic, P1	F(000) = 204
Hall symbol: -P 1	Dx = 1.514 Mg m−3
a = 4.8451 (5) Å	Melting point: 429-432 K K
b = 7.7564 (7) Å	Mo Kα radiation, λ = 0.71073 Å
c = 12.1064 (9) Å	µ = 0.12 mm−1
α = 79.476 (7)°	T = 100 K
β = 79.575 (7)°	Prismatic, colourless
γ = 76.125 (8)°	0.32 × 0.20 × 0.14 mm

Kuma KM4 CCD diffractometer	2106 independent reflections
Radiation source: fine-focus sealed tube	1526 reflections with I > 2σ(I)
graphite	Rint = 0.018
Detector resolution: 8.6479 pixels mm-1	θmax = 28.6°, θmin = 3.0°
ω scan	h = −6→6
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction 2005)	k = −10→10
Tmin = 0.95, Tmax = 0.98	l = −16→16
12229 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	All H-atom parameters refined
S = 1.05	w = 1/[σ^2^(Fo^2^) + (0.0643P)^2^] where P = (Fo^2^ + 2Fc^2^)/3
2106 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

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

Refinement. Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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	0.5522 (3)	0.79514 (18)	0.40716 (11)	0.0168 (3)
O2	0.77114 (19)	0.78932 (13)	0.46290 (7)	0.0247 (2)
O3	0.3223 (2)	0.93263 (13)	0.41255 (8)	0.0295 (3)
O4	0.20761 (17)	0.81061 (11)	0.23177 (7)	0.0181 (2)
C5	0.3211 (3)	0.92945 (19)	0.13926 (12)	0.0300 (3)
C6	0.2362 (2)	0.50663 (16)	0.11119 (9)	0.0165 (3)
O7	0.04150 (18)	0.65037 (11)	0.08598 (7)	0.0199 (2)
O8	0.27658 (18)	0.36943 (11)	0.06341 (7)	0.0216 (2)
C9	0.5714 (2)	0.63677 (16)	0.34035 (9)	0.0168 (3)
C10	0.3987 (2)	0.65025 (15)	0.25686 (9)	0.0147 (3)
C11	0.4152 (2)	0.50426 (15)	0.20035 (9)	0.0162 (3)
C12	0.6083 (3)	0.34441 (17)	0.22948 (10)	0.0200 (3)
C13	0.7810 (3)	0.32923 (17)	0.31153 (11)	0.0232 (3)
C14	0.7620 (3)	0.47419 (17)	0.36588 (10)	0.0204 (3)
H2	0.729 (4)	0.869 (2)	0.5008 (16)	0.052 (5)*
H3	0.204 (5)	0.903 (3)	0.3808 (19)	0.083 (7)*
H5A	0.506 (4)	0.956 (2)	0.1564 (13)	0.043 (4)*
H5B	0.187 (3)	1.040 (2)	0.1310 (13)	0.043 (4)*
H5C	0.361 (3)	0.8735 (19)	0.0712 (13)	0.031 (4)*
H8	−0.080 (4)	0.638 (2)	0.0276 (16)	0.067 (6)*
H12	0.612 (3)	0.245 (2)	0.1950 (12)	0.025 (4)*
H13	0.906 (3)	0.217 (2)	0.3314 (12)	0.030 (4)*
H14	0.878 (3)	0.4602 (18)	0.4239 (11)	0.024 (4)*

	U11	U22	U33	U12	U13	U23
B1	0.0178 (7)	0.0218 (7)	0.0127 (6)	−0.0063 (5)	−0.0035 (5)	−0.0036 (5)
O2	0.0229 (5)	0.0308 (5)	0.0255 (5)	−0.0031 (4)	−0.0095 (4)	−0.0147 (4)
O3	0.0305 (5)	0.0277 (5)	0.0376 (6)	0.0014 (4)	−0.0205 (4)	−0.0182 (4)
O4	0.0218 (4)	0.0159 (4)	0.0178 (4)	−0.0018 (3)	−0.0072 (3)	−0.0040 (3)
C5	0.0408 (8)	0.0200 (7)	0.0276 (7)	−0.0065 (6)	−0.0072 (6)	0.0031 (6)
C6	0.0174 (6)	0.0191 (6)	0.0147 (6)	−0.0076 (5)	−0.0012 (4)	−0.0034 (5)
O7	0.0212 (4)	0.0209 (5)	0.0201 (4)	−0.0022 (4)	−0.0103 (3)	−0.0048 (3)
O8	0.0280 (5)	0.0219 (5)	0.0193 (4)	−0.0088 (4)	−0.0060 (4)	−0.0069 (4)
C9	0.0156 (6)	0.0220 (6)	0.0139 (6)	−0.0063 (5)	−0.0025 (4)	−0.0023 (5)
C10	0.0146 (5)	0.0156 (6)	0.0142 (5)	−0.0042 (4)	−0.0012 (4)	−0.0024 (4)
C11	0.0167 (6)	0.0179 (6)	0.0149 (6)	−0.0062 (5)	−0.0007 (4)	−0.0028 (5)
C12	0.0215 (6)	0.0169 (6)	0.0222 (6)	−0.0051 (5)	−0.0012 (5)	−0.0045 (5)
C13	0.0210 (6)	0.0197 (6)	0.0257 (7)	−0.0013 (5)	−0.0036 (5)	0.0007 (5)
C14	0.0178 (6)	0.0273 (7)	0.0164 (6)	−0.0054 (5)	−0.0049 (5)	−0.0002 (5)

B1—O2	1.3443 (15)	C6—C11	1.4971 (16)
B1—O3	1.3461 (16)	O7—H8	1.03 (2)
B1—C9	1.5661 (17)	C9—C14	1.3933 (17)
O2—H2	0.802 (19)	C9—C10	1.3993 (16)
O3—H3	0.84 (2)	C10—C11	1.4059 (16)
O4—C10	1.3813 (14)	C11—C12	1.3931 (17)
O4—C5	1.4317 (15)	C12—C13	1.3825 (18)
C5—H5A	1.029 (17)	C12—H12	0.938 (15)
C5—H5B	0.942 (17)	C13—C14	1.3799 (18)
C5—H5C	0.968 (15)	C13—H13	0.955 (15)
C6—O8	1.2607 (13)	C14—H14	0.951 (14)
C6—O7	1.3044 (14)
O2—B1—O3	119.64 (11)	C14—C9—B1	119.41 (10)
O2—B1—C9	118.18 (11)	C10—C9—B1	122.49 (10)
O3—B1—C9	122.16 (10)	O4—C10—C9	118.38 (10)
B1—O2—H2	109.5 (13)	O4—C10—C11	120.37 (10)
B1—O3—H3	104.3 (15)	C9—C10—C11	121.25 (11)
C10—O4—C5	113.51 (10)	C12—C11—C10	118.37 (10)
O4—C5—H5A	110.1 (9)	C12—C11—C6	116.96 (10)
O4—C5—H5B	109.1 (10)	C10—C11—C6	124.66 (10)
H5A—C5—H5B	107.3 (13)	C13—C12—C11	121.05 (11)
O4—C5—H5C	108.6 (9)	C13—C12—H12	120.4 (9)
H5A—C5—H5C	110.3 (13)	C11—C12—H12	118.5 (9)
H5B—C5—H5C	111.4 (13)	C14—C13—C12	119.70 (12)
O8—C6—O7	122.02 (10)	C14—C13—H13	121.3 (9)
O8—C6—C11	119.10 (10)	C12—C13—H13	118.9 (9)
O7—C6—C11	118.88 (10)	C13—C14—C9	121.55 (11)
C6—O7—H8	114.0 (10)	C13—C14—H14	118.6 (8)
C14—C9—C10	118.08 (11)	C9—C14—H14	119.8 (8)
O2—B1—C9—C14	18.65 (16)	O4—C10—C11—C6	0.00 (17)
O3—B1—C9—C14	−159.62 (11)	C9—C10—C11—C6	179.25 (10)
O2—B1—C9—C10	−162.83 (11)	O8—C6—C11—C12	−3.26 (16)
O3—B1—C9—C10	18.89 (18)	O7—C6—C11—C12	176.22 (10)
C5—O4—C10—C9	93.35 (12)	O8—C6—C11—C10	177.57 (10)
C5—O4—C10—C11	−87.38 (13)	O7—C6—C11—C10	−2.95 (16)
C14—C9—C10—O4	179.50 (10)	C10—C11—C12—C13	−0.30 (18)
B1—C9—C10—O4	0.96 (16)	C6—C11—C12—C13	−179.52 (11)
C14—C9—C10—C11	0.24 (17)	C11—C12—C13—C14	0.18 (19)
B1—C9—C10—C11	−178.30 (10)	C12—C13—C14—C9	0.16 (19)
O4—C10—C11—C12	−179.16 (10)	C10—C9—C14—C13	−0.37 (17)
C9—C10—C11—C12	0.09 (17)	B1—C9—C14—C13	178.22 (10)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3i	0.802 (19)	1.96 (2)	2.7572 (13)	172.6 (18)
O3—H3···O4	0.84 (2)	2.06 (2)	2.7283 (12)	136.8 (19)
O3—H3···O2ii	0.84 (2)	2.45 (2)	3.0538 (14)	130.2 (19)
O7—H8···O8iii	1.03 (2)	1.60 (2)	2.6255 (11)	177.0 (16)

B1—O2	1.3443 (15)
B1—O3	1.3461 (16)
B1—C9	1.5661 (17)
C6—O8	1.2607 (13)
C6—O7	1.3044 (14)

O2—B1—C9—C14	18.65 (16)
C5—O4—C10—C9	93.35 (12)
O8—C6—C11—C10	177.57 (10)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3i	0.802 (19)	1.96 (2)	2.7572 (13)	172.6 (18)
O3—H3⋯O4	0.84 (2)	2.06 (2)	2.7283 (12)	136.8 (19)
O3—H3⋯O2ii	0.84 (2)	2.45 (2)	3.0538 (14)	130.2 (19)
O7—H8⋯O8iii	1.03 (2)	1.60 (2)	2.6255 (11)	177.0 (16)

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