2,4-Dibutoxy-phenyl-boronic acid.

In the crystal of the title compound, C(14)H(23)BO(4), centrosymmetric dimers linked by pairs of O-H⋯O hydrogen bonds occur. The dimers are linked via C-H⋯O contacts, generating a two-dimensional array parallel to (12). These are inter-connected by weak O-H⋯O hydrogen bonds, as well as C-H⋯π inter-actions.

Related literature

For the structural characterization of related ortho-alk­oxy aryl­boronic acids, see: Dąbrowski et al. (2006 ▶, 2008 ▶); Luliński (2008 ▶); Yang et al. (2005 ▶).

Experimental

Crystal data

C14H23BO4

M = 266.13

Triclinic,

a = 5.3129 (8) Å

b = 11.3611 (13) Å

c = 13.7362 (17) Å

α = 112.747 (11)°

β = 94.311 (11)°

γ = 100.385 (11)°

V = 742.45 (17) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.65 × 0.20 × 0.09 mm

Data collection

Oxford Diffraction KM-4-CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction 2005 ▶) T min = 0.96, T max = 0.99

14053 measured reflections

3570 independent reflections

2633 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.095

S = 1.05

3570 reflections

180 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.23 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809023332/tk2482sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809023332/tk2482Isup2.hkl

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

C14H23BO4	V = 742.45 (17) Å3
Mr = 266.13	Z = 2
Triclinic, P1	F(000) = 288
Hall symbol: -P 1	Dx = 1.190 Mg m−3
a = 5.3129 (8) Å	Melting point: 369 K
b = 11.3611 (13) Å	Mo Kα radiation, λ = 0.71073 Å
c = 13.7362 (17) Å	µ = 0.08 mm−1
α = 112.747 (11)°	T = 100 K
β = 94.311 (11)°	Prismatic, colourless
γ = 100.385 (11)°	0.65 × 0.20 × 0.09 mm

Oxford Diffraction KM-4-CCD diffractometer	3570 independent reflections
Radiation source: fine-focus sealed tube	2633 reflections with I > 2σ(I)
graphite	Rint = 0.018
Detector resolution: 8.6479 pixels mm-1	θmax = 28.6°, θmin = 3.1°
ω scans	h = −7→7
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction 2005)	k = −15→15
Tmin = 0.96, Tmax = 0.99	l = −18→18
14053 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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0557P)2] where P = (Fo2 + 2Fc2)/3
3570 reflections	(Δ/σ)max = 0.001
180 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.23 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
C1	0.56253 (19)	0.61272 (9)	0.78929 (7)	0.0153 (2)
C2	0.72694 (19)	0.56726 (10)	0.84327 (8)	0.0170 (2)
H2	0.8262	0.5095	0.8031	0.020*
C3	0.75323 (19)	0.60219 (10)	0.95310 (8)	0.0171 (2)
H3	0.8666	0.5685	0.9869	0.021*
C4	0.60985 (19)	0.68740 (10)	1.01210 (7)	0.0155 (2)
C5	0.44559 (18)	0.73795 (9)	0.96259 (8)	0.0159 (2)
H5	0.3502	0.7974	1.0036	0.019*
C6	0.42293 (18)	0.70058 (9)	0.85288 (8)	0.0146 (2)
C7	0.14424 (19)	0.84955 (10)	0.85803 (8)	0.0167 (2)
H7A	0.2754	0.9274	0.9086	0.020*
H7B	0.0232	0.8190	0.8992	0.020*
C8	−0.00127 (19)	0.88312 (10)	0.77716 (8)	0.0169 (2)
H8A	−0.1220	0.8025	0.7244	0.020*
H8B	0.1239	0.9154	0.7382	0.020*
C9	−0.15422 (19)	0.98636 (10)	0.82756 (8)	0.0187 (2)
H9A	−0.0328	1.0699	0.8751	0.022*
H9B	−0.2692	0.9580	0.8717	0.022*
C10	−0.3170 (2)	1.00821 (11)	0.74256 (9)	0.0240 (2)
H10A	−0.4393	0.9259	0.6962	0.036*
H10B	−0.2032	1.0378	0.6996	0.036*
H10C	−0.4132	1.0750	0.7772	0.036*
C7'	0.79357 (19)	0.68855 (10)	1.17808 (8)	0.0173 (2)
H7A'	0.9734	0.7183	1.1687	0.021*
H7B'	0.7528	0.5918	1.1514	0.021*
C8'	0.7655 (2)	0.74945 (10)	1.29481 (8)	0.0192 (2)
H8A'	0.5885	0.7140	1.3037	0.023*
H8B'	0.7892	0.8454	1.3185	0.023*
C9'	0.9634 (2)	0.72152 (11)	1.36433 (8)	0.0244 (3)
H9A'	1.1400	0.7584	1.3560	0.029*
H9B'	0.9421	0.6255	1.3391	0.029*
C10'	0.9371 (3)	0.77900 (13)	1.48245 (9)	0.0378 (3)
H10D	0.7640	0.7414	1.4915	0.057*
H10E	0.9621	0.8743	1.5085	0.057*
H10F	1.0684	0.7582	1.5233	0.057*
O1	0.73656 (14)	0.51449 (8)	0.61804 (6)	0.0245 (2)
O2	0.34414 (15)	0.57844 (8)	0.60251 (6)	0.0253 (2)
O3	0.26778 (13)	0.74719 (7)	0.79858 (5)	0.01810 (17)
O4	0.61551 (13)	0.72922 (7)	1.12026 (5)	0.01908 (18)
B1	0.5445 (2)	0.56749 (11)	0.66526 (9)	0.0170 (2)
H1o	0.709 (3)	0.4847 (14)	0.5482 (13)	0.049 (4)*
H2o	0.231 (3)	0.6103 (14)	0.6371 (12)	0.051 (4)*

	U11	U22	U33	U12	U13	U23
C1	0.0172 (5)	0.0154 (5)	0.0130 (5)	0.0038 (4)	0.0023 (4)	0.0053 (4)
C2	0.0199 (5)	0.0166 (5)	0.0144 (5)	0.0070 (4)	0.0038 (4)	0.0049 (4)
C3	0.0201 (5)	0.0188 (5)	0.0150 (5)	0.0080 (4)	0.0012 (4)	0.0083 (4)
C4	0.0180 (5)	0.0172 (5)	0.0106 (5)	0.0029 (4)	0.0018 (4)	0.0057 (4)
C5	0.0166 (5)	0.0166 (5)	0.0140 (5)	0.0060 (4)	0.0034 (4)	0.0045 (4)
C6	0.0140 (5)	0.0160 (5)	0.0149 (5)	0.0036 (4)	0.0005 (4)	0.0077 (4)
C7	0.0188 (5)	0.0176 (5)	0.0137 (5)	0.0084 (4)	0.0033 (4)	0.0045 (4)
C8	0.0179 (5)	0.0190 (5)	0.0155 (5)	0.0068 (4)	0.0027 (4)	0.0078 (4)
C9	0.0197 (5)	0.0185 (5)	0.0188 (5)	0.0073 (4)	0.0044 (4)	0.0071 (4)
C10	0.0232 (6)	0.0251 (6)	0.0264 (6)	0.0108 (5)	0.0040 (4)	0.0111 (5)
C7'	0.0198 (5)	0.0211 (5)	0.0133 (5)	0.0087 (4)	0.0019 (4)	0.0079 (4)
C8'	0.0244 (6)	0.0222 (5)	0.0126 (5)	0.0093 (4)	0.0038 (4)	0.0069 (4)
C9'	0.0322 (6)	0.0298 (6)	0.0145 (5)	0.0136 (5)	0.0032 (4)	0.0097 (5)
C10'	0.0571 (9)	0.0448 (8)	0.0151 (6)	0.0230 (7)	0.0018 (5)	0.0117 (5)
O1	0.0283 (4)	0.0359 (5)	0.0108 (4)	0.0177 (4)	0.0041 (3)	0.0064 (3)
O2	0.0296 (4)	0.0386 (5)	0.0122 (4)	0.0227 (4)	0.0060 (3)	0.0081 (3)
O3	0.0230 (4)	0.0218 (4)	0.0117 (3)	0.0131 (3)	0.0022 (3)	0.0057 (3)
O4	0.0248 (4)	0.0248 (4)	0.0107 (3)	0.0120 (3)	0.0029 (3)	0.0076 (3)
B1	0.0229 (6)	0.0161 (6)	0.0125 (5)	0.0067 (5)	0.0026 (5)	0.0053 (4)

C1—C2	1.3932 (13)	C9—H9B	0.9900
C1—C6	1.4140 (13)	C10—H10A	0.9800
C1—B1	1.5674 (14)	C10—H10B	0.9800
C2—C3	1.3923 (13)	C10—H10C	0.9800
C2—H2	0.9500	C7'—O4	1.4379 (11)
C3—C4	1.3879 (14)	C7'—C8'	1.5123 (14)
C3—H3	0.9500	C7'—H7A'	0.9900
C4—O4	1.3697 (11)	C7'—H7B'	0.9900
C4—C5	1.3955 (13)	C8'—C9'	1.5237 (14)
C5—C6	1.3875 (13)	C8'—H8A'	0.9900
C5—H5	0.9500	C8'—H8B'	0.9900
C6—O3	1.3736 (11)	C9'—C10'	1.5251 (15)
C7—O3	1.4392 (11)	C9'—H9A'	0.9900
C7—C8	1.5105 (13)	C9'—H9B'	0.9900
C7—H7A	0.9900	C10'—H10D	0.9800
C7—H7B	0.9900	C10'—H10E	0.9800
C8—C9	1.5217 (13)	C10'—H10F	0.9800
C8—H8A	0.9900	O1—B1	1.3577 (13)
C8—H8B	0.9900	O1—H1o	0.876 (16)
C9—C10	1.5241 (14)	O2—B1	1.3727 (13)
C9—H9A	0.9900	O2—H2o	0.839 (15)
C2—C1—C6	116.20 (8)	C9—C10—H10B	109.5
C2—C1—B1	119.80 (8)	H10A—C10—H10B	109.5
C6—C1—B1	123.99 (9)	C9—C10—H10C	109.5
C3—C2—C1	123.36 (9)	H10A—C10—H10C	109.5
C3—C2—H2	118.3	H10B—C10—H10C	109.5
C1—C2—H2	118.3	O4—C7'—C8'	107.43 (8)
C4—C3—C2	118.41 (9)	O4—C7'—H7A'	110.2
C4—C3—H3	120.8	C8'—C7'—H7A'	110.2
C2—C3—H3	120.8	O4—C7'—H7B'	110.2
O4—C4—C3	124.59 (9)	C8'—C7'—H7B'	110.2
O4—C4—C5	114.68 (8)	H7A'—C7'—H7B'	108.5
C3—C4—C5	120.73 (9)	C7'—C8'—C9'	111.40 (8)
C6—C5—C4	119.37 (9)	C7'—C8'—H8A'	109.3
C6—C5—H5	120.3	C9'—C8'—H8A'	109.3
C4—C5—H5	120.3	C7'—C8'—H8B'	109.3
O3—C6—C5	122.81 (8)	C9'—C8'—H8B'	109.3
O3—C6—C1	115.27 (8)	H8A'—C8'—H8B'	108.0
C5—C6—C1	121.91 (8)	C8'—C9'—C10'	112.88 (9)
O3—C7—C8	106.65 (8)	C8'—C9'—H9A'	109.0
O3—C7—H7A	110.4	C10'—C9'—H9A'	109.0
C8—C7—H7A	110.4	C8'—C9'—H9B'	109.0
O3—C7—H7B	110.4	C10'—C9'—H9B'	109.0
C8—C7—H7B	110.4	H9A'—C9'—H9B'	107.8
H7A—C7—H7B	108.6	C9'—C10'—H10D	109.5
C7—C8—C9	113.05 (8)	C9'—C10'—H10E	109.5
C7—C8—H8A	109.0	H10D—C10'—H10E	109.5
C9—C8—H8A	109.0	C9'—C10'—H10F	109.5
C7—C8—H8B	109.0	H10D—C10'—H10F	109.5
C9—C8—H8B	109.0	H10E—C10'—H10F	109.5
H8A—C8—H8B	107.8	B1—O1—H1o	113.8 (9)
C8—C9—C10	111.28 (8)	B1—O2—H2o	113.1 (10)
C8—C9—H9A	109.4	C6—O3—C7	119.23 (7)
C10—C9—H9A	109.4	C4—O4—C7'	117.93 (7)
C8—C9—H9B	109.4	O1—B1—O2	118.73 (9)
C10—C9—H9B	109.4	O1—B1—C1	118.07 (9)
H9A—C9—H9B	108.0	O2—B1—C1	123.20 (9)
C9—C10—H10A	109.5
C6—C1—C2—C3	1.25 (15)	C7—C8—C9—C10	−174.85 (9)
B1—C1—C2—C3	−179.69 (9)	O4—C7'—C8'—C9'	−175.14 (8)
C1—C2—C3—C4	−0.48 (15)	C7'—C8'—C9'—C10'	−178.76 (10)
C2—C3—C4—O4	179.58 (9)	C5—C6—O3—C7	6.91 (13)
C2—C3—C4—C5	−0.72 (15)	C1—C6—O3—C7	−172.13 (8)
O4—C4—C5—C6	−179.21 (8)	C8—C7—O3—C6	177.59 (8)
C3—C4—C5—C6	1.07 (15)	C3—C4—O4—C7'	3.91 (14)
C4—C5—C6—O3	−179.22 (9)	C5—C4—O4—C7'	−175.81 (8)
C4—C5—C6—C1	−0.24 (14)	C8'—C7'—O4—C4	178.89 (8)
C2—C1—C6—O3	178.18 (8)	C2—C1—B1—O1	−17.36 (14)
B1—C1—C6—O3	−0.84 (14)	C6—C1—B1—O1	161.62 (10)
C2—C1—C6—C5	−0.88 (14)	C2—C1—B1—O2	162.36 (10)
B1—C1—C6—C5	−179.89 (9)	C6—C1—B1—O2	−18.66 (16)
O3—C7—C8—C9	177.25 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O2i	0.876 (16)	1.889 (17)	2.7649 (11)	178.9 (14)
O2—H2o···O3	0.839 (15)	2.129 (15)	2.7469 (10)	130.3 (13)
O2—H2o···O1ii	0.839 (15)	2.610 (15)	3.2205 (12)	130.7 (12)
C10—H10C···O4iii	0.98	2.60	3.5739 (15)	173 (1)
C9'—H9B'···O1iv	0.99	2.71	3.4314 (17)	130 (1)
C7—H7B···Cgv	0.99	2.74	3.6237 (12)	149
C7'—H7B'···Cgvi	0.99	2.80	3.7109 (12)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯O2i	0.876 (16)	1.889 (17)	2.7649 (11)	178.9 (14)
O2—H2o⋯O3	0.839 (15)	2.129 (15)	2.7469 (10)	130.3 (13)
O2—H2o⋯O1ii	0.839 (15)	2.610 (15)	3.2205 (12)	130.7 (12)
C10—H10C⋯O4iii	0.98	2.60	3.5739 (15)	173 (1)
C9′—H9B′⋯O1iv	0.99	2.71	3.4314 (17)	130 (1)
C7—H7B⋯Cgvi	0.99	2.74	3.6237 (12)	149
C7′—H7B′⋯Cgvii	0.99	2.80	3.7109 (12)	153

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) . Cg is the centroid of the C1–C6 ring.