(2-Butoxy-phen-yl)boronic acid.

The title compound, 2-(CH(3)CH(2)CH(2)CH(2)O)C(6)H(4)B(OH)(2), exists as a centrosymmetric hydrogen-bonded dimer. Dimers are linked via C-H⋯π and π-π [with closest C⋯C contact of 3.540 (3) Å] inter-actions to produce a two-dimensional array.

Related literature

For related literature, see: Rettig & Trotter (1977 ▶). For the structures of related ortho-alkoxy­aryl­boronic acids, see: Dabrowski et al. (2006 ▶); Serwatowski et al. (2006 ▶); Yang et al. (2005 ▶).

Experimental

Crystal data

C10H15BO3

M = 194.03

Monoclinic,

a = 7.4809 (4) Å

b = 15.3510 (7) Å

c = 9.2824 (4) Å

β = 94.299 (4)°

V = 1062.98 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 102 (2) K

0.74 × 0.47 × 0.32 mm

Data collection

Kuma KM4 CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2005 ▶) T min = 0.92, T max = 0.97

9363 measured reflections

2419 independent reflections

1924 reflections with I > 2σ(I)

R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.096

S = 1.14

2419 reflections

188 parameters

All H-atom parameters refined

Δρmax = 0.35 e Å−3

Δρmin = −0.16 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/S1600536808000457/tk2240sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808000457/tk2240Isup2.hkl

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

C10H15BO3	F000 = 416
Mr = 194.03	Dx = 1.212 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7109 reflections
a = 7.4809 (4) Å	θ = 2.3–30.0º
b = 15.3510 (7) Å	µ = 0.09 mm−1
c = 9.2824 (4) Å	T = 102 (2) K
β = 94.299 (4)º	Prismatic, colourless
V = 1062.98 (9) Å3	0.74 × 0.47 × 0.32 mm
Z = 4

Kuma KM4 CCD diffractometer	2419 independent reflections
Radiation source: fine-focus sealed tube	1924 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.012
Detector resolution: 8.6479 pixels mm-1	θmax = 27.5º
T = 102(2) K	θmin = 2.7º
ω scans	h = −9→9
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2005)	k = −19→19
Tmin = 0.92, Tmax = 0.97	l = −12→11
9363 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	All H-atom parameters refined
R[F2 > 2σ(F2)] = 0.032	w = 1/[σ2(Fo2) + (0.0603P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.096	(Δ/σ)max < 0.001
S = 1.14	Δρmax = 0.35 e Å−3
2419 reflections	Δρmin = −0.16 e Å−3
188 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.015 (3)
Secondary atom site location: difference Fourier map

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 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
C1	0.22865 (11)	0.48929 (6)	0.46605 (10)	0.0187 (2)
C2	0.15354 (11)	0.42983 (6)	0.36299 (10)	0.0181 (2)
C3	0.12666 (12)	0.34464 (6)	0.41017 (11)	0.0213 (2)
C4	0.16761 (12)	0.31891 (6)	0.55234 (11)	0.0242 (2)
C5	0.23872 (12)	0.37970 (7)	0.65050 (10)	0.0244 (2)
C6	0.27140 (12)	0.46477 (6)	0.60865 (10)	0.0219 (2)
C7	0.32860 (12)	0.63751 (6)	0.51594 (10)	0.0196 (2)
C8	0.34388 (13)	0.72079 (6)	0.43222 (10)	0.0205 (2)
C9	0.42380 (14)	0.79405 (6)	0.52702 (11)	0.0236 (2)
C10	0.46998 (16)	0.87395 (7)	0.44072 (13)	0.0324 (3)
B1	0.09189 (13)	0.45600 (7)	0.20334 (11)	0.0189 (2)
O1	0.25505 (9)	0.57244 (4)	0.41655 (7)	0.02163 (19)
O2	0.10984 (9)	0.53922 (4)	0.15252 (7)	0.02530 (19)
O3	0.01624 (9)	0.39432 (4)	0.11431 (8)	0.0266 (2)
H2O	0.157 (2)	0.5714 (9)	0.2219 (17)	0.056 (4)*
H3O	−0.0232 (18)	0.4136 (9)	0.0250 (16)	0.055 (4)*
H3	0.0761 (15)	0.3037 (7)	0.3414 (12)	0.027 (3)*
H4	0.1452 (14)	0.2583 (7)	0.5786 (12)	0.028 (3)*
H5	0.2692 (15)	0.3638 (8)	0.7519 (13)	0.034 (3)*
H6	0.3221 (14)	0.5074 (7)	0.6758 (12)	0.029 (3)*
H7A	0.4484 (14)	0.6175 (7)	0.5556 (10)	0.022 (3)*
H7B	0.2485 (13)	0.6452 (7)	0.5943 (11)	0.019 (2)*
H8A	0.4243 (13)	0.7100 (6)	0.3536 (11)	0.022 (3)*
H8B	0.2185 (14)	0.7378 (7)	0.3876 (12)	0.026 (3)*
H9A	0.5375 (14)	0.7721 (7)	0.5801 (12)	0.027 (3)*
H9B	0.3361 (16)	0.8101 (7)	0.5990 (12)	0.030 (3)*
H10A	0.5591 (18)	0.8578 (8)	0.3676 (15)	0.052 (4)*
H10B	0.3595 (18)	0.8990 (8)	0.3852 (14)	0.045 (3)*
H10C	0.5225 (16)	0.9206 (8)	0.5042 (13)	0.045 (4)*

	U11	U22	U33	U12	U13	U23
C1	0.0164 (4)	0.0187 (5)	0.0210 (5)	0.0035 (3)	0.0007 (3)	0.0005 (4)
C2	0.0152 (4)	0.0192 (5)	0.0200 (4)	0.0025 (3)	0.0009 (3)	0.0001 (4)
C3	0.0193 (5)	0.0195 (5)	0.0251 (5)	0.0011 (4)	0.0010 (4)	−0.0008 (4)
C4	0.0241 (5)	0.0203 (5)	0.0284 (5)	0.0027 (4)	0.0032 (4)	0.0056 (4)
C5	0.0242 (5)	0.0281 (5)	0.0209 (5)	0.0060 (4)	0.0012 (4)	0.0053 (4)
C6	0.0229 (5)	0.0233 (5)	0.0190 (5)	0.0035 (4)	−0.0016 (4)	−0.0015 (4)
C7	0.0212 (5)	0.0204 (5)	0.0167 (4)	0.0003 (3)	−0.0026 (4)	−0.0041 (4)
C8	0.0223 (5)	0.0216 (5)	0.0171 (5)	0.0011 (4)	−0.0020 (4)	−0.0013 (4)
C9	0.0306 (5)	0.0193 (5)	0.0200 (5)	0.0018 (4)	−0.0031 (4)	−0.0021 (4)
C10	0.0397 (6)	0.0234 (5)	0.0332 (6)	−0.0038 (5)	−0.0032 (5)	0.0012 (5)
B1	0.0179 (5)	0.0184 (5)	0.0205 (5)	0.0009 (4)	0.0011 (4)	−0.0009 (4)
O1	0.0289 (4)	0.0173 (4)	0.0176 (3)	−0.0030 (3)	−0.0047 (3)	−0.0005 (3)
O2	0.0369 (4)	0.0203 (4)	0.0176 (4)	−0.0063 (3)	−0.0057 (3)	−0.0002 (3)
O3	0.0363 (4)	0.0194 (4)	0.0225 (4)	−0.0020 (3)	−0.0090 (3)	−0.0008 (3)

C1—O1	1.3758 (11)	C7—H7B	0.983 (10)
C1—C6	1.3902 (13)	C8—C9	1.5223 (13)
C1—C2	1.4083 (13)	C8—H8A	0.994 (10)
C2—C3	1.3984 (13)	C8—H8B	1.030 (10)
C2—B1	1.5710 (13)	C9—C10	1.5189 (14)
C3—C4	1.3895 (13)	C9—H9A	1.009 (11)
C3—H3	0.954 (11)	C9—H9B	1.001 (12)
C4—C5	1.3825 (14)	C10—H10A	1.017 (14)
C4—H4	0.980 (10)	C10—H10B	1.017 (13)
C5—C6	1.3895 (14)	C10—H10C	0.990 (13)
C5—H5	0.982 (12)	B1—O3	1.3526 (12)
C6—H6	0.962 (12)	B1—O2	1.3718 (12)
C7—O1	1.4408 (10)	O2—H2O	0.864 (16)
C7—C8	1.5050 (13)	O3—H3O	0.909 (15)
C7—H7A	0.992 (10)
O1—C1—C6	122.72 (9)	C7—C8—C9	111.76 (7)
O1—C1—C2	115.75 (8)	C7—C8—H8A	108.1 (6)
C6—C1—C2	121.53 (9)	C9—C8—H8A	108.3 (6)
C3—C2—C1	116.92 (8)	C7—C8—H8B	108.7 (6)
C3—C2—B1	119.71 (8)	C9—C8—H8B	110.6 (6)
C1—C2—B1	123.30 (8)	H8A—C8—H8B	109.3 (8)
C4—C3—C2	122.46 (9)	C10—C9—C8	112.75 (8)
C4—C3—H3	119.8 (6)	C10—C9—H9A	108.1 (6)
C2—C3—H3	117.8 (6)	C8—C9—H9A	108.4 (6)
C5—C4—C3	118.72 (9)	C10—C9—H9B	109.8 (6)
C5—C4—H4	122.8 (6)	C8—C9—H9B	108.6 (6)
C3—C4—H4	118.5 (6)	H9A—C9—H9B	109.1 (9)
C4—C5—C6	121.15 (9)	C9—C10—H10A	110.0 (7)
C4—C5—H5	120.9 (7)	C9—C10—H10B	111.4 (7)
C6—C5—H5	118.0 (7)	H10A—C10—H10B	107.6 (11)
C5—C6—C1	119.20 (9)	C9—C10—H10C	111.5 (7)
C5—C6—H6	121.8 (7)	H10A—C10—H10C	108.8 (10)
C1—C6—H6	119.0 (7)	H10B—C10—H10C	107.4 (10)
O1—C7—C8	107.37 (7)	O3—B1—O2	119.28 (8)
O1—C7—H7A	108.3 (6)	O3—B1—C2	118.50 (8)
C8—C7—H7A	110.7 (6)	O2—B1—C2	122.22 (8)
O1—C7—H7B	109.4 (6)	C1—O1—C7	119.14 (7)
C8—C7—H7B	110.7 (6)	B1—O2—H2O	108.7 (10)
H7A—C7—H7B	110.3 (8)	B1—O3—H3O	114.9 (9)
O1—C1—C2—C3	179.49 (7)	C2—C1—C6—C5	−0.21 (14)
C6—C1—C2—C3	−1.00 (13)	O1—C7—C8—C9	−179.00 (7)
O1—C1—C2—B1	−3.50 (13)	C7—C8—C9—C10	170.24 (9)
C6—C1—C2—B1	176.01 (8)	C3—C2—B1—O3	−1.04 (13)
C1—C2—C3—C4	1.34 (13)	C1—C2—B1—O3	−177.97 (8)
B1—C2—C3—C4	−175.78 (8)	C3—C2—B1—O2	177.95 (8)
C2—C3—C4—C5	−0.45 (14)	C1—C2—B1—O2	1.02 (14)
C3—C4—C5—C6	−0.84 (14)	C6—C1—O1—C7	−0.53 (12)
C4—C5—C6—C1	1.16 (14)	C2—C1—O1—C7	178.98 (8)
O1—C1—C6—C5	179.27 (8)	C8—C7—O1—C1	179.46 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O1	0.864 (16)	1.900 (16)	2.6547 (9)	145.1 (13)
O3—H3O···O2i	0.909 (15)	1.870 (15)	2.7776 (9)	175.8 (13)
C7—H7A···C1ii	0.992 (10)	2.939 (10)	3.8346 (12)	150.7 (8)
C7—H7A···C2ii	0.992 (10)	3.103 (10)	4.0850 (12)	170.7 (8)
C7—H7A···C6ii	0.992 (10)	2.965 (10)	3.6436 (13)	126.5 (7)

Table 1

Hydrogen-bond and C—H⋯π geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯O1	0.864 (16)	1.900 (16)	2.6547 (9)	145.1 (13)
O3—H3O⋯O2i	0.909 (15)	1.870 (15)	2.7776 (9)	175.8 (13)
C7—H7A⋯C1ii	0.992 (10)	2.939 (10)	3.8346 (12)	150.7 (8)
C7—H7A⋯C2ii	0.992 (10)	3.103 (10)	4.0850 (12)	170.7 (8)
C7—H7A⋯C6ii	0.992 (10)	2.965 (10)	3.6436 (13)	126.5 (7)

Symmetry codes: (i) ; (ii) .