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The title compound, C6H6BFO2, is a versatile building block in organic synthesis. In the crystal structure, inter­molecular O—H...O hydrogen bonds link the mol­ecules into dimers, which may be effective in the stabilization of the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806034763/hk2115sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806034763/hk2115Isup2.hkl
Contains datablock I

CCDC reference: 624725

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.084
  • wR factor = 0.189
  • Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT030_ALERT_1_C _diffrn_reflns_number .LE. _reflns_number_total ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.27 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

3-Fluorophenylboronic acid top
Crystal data top
C6H6BFO2F(000) = 288
Mr = 139.92Dx = 1.434 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 5.7560 (12) Åθ = 10–12°
b = 5.027 (1) ŵ = 0.12 mm1
c = 22.402 (5) ÅT = 294 K
β = 91.19 (3)°Block, white
V = 648.1 (2) Å30.30 × 0.20 × 0.10 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer
868 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.000
Graphite monochromatorθmax = 26.0°, θmin = 1.8°
ω/2θ scansh = 77
Absorption correction: ψ scan
(North et al., 1968)
k = 06
Tmin = 0.965, Tmax = 0.988l = 027
1265 measured reflections3 standard reflections every 120 min
1265 independent reflections intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.084Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.189H atoms treated by a mixture of independent and constrained refinement
S = 0.97 w = 1/[σ2(Fo2) + (0.03P)2 + 2P]
where P = (Fo2 + 2Fc2)/3
1265 reflections(Δ/σ)max < 0.001
97 parametersΔρmax = 0.23 e Å3
2 restraintsΔρmin = 0.21 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F1.0010 (5)0.3535 (7)0.15299 (15)0.1001 (12)
O10.2372 (6)0.2302 (7)0.03199 (16)0.0796 (11)
H10.168 (8)0.216 (11)0.0018 (13)0.091*
O20.1524 (6)0.2182 (6)0.04460 (17)0.0776 (11)
H20.183 (9)0.376 (5)0.057 (2)0.091*
B0.2811 (9)0.0000 (11)0.0604 (3)0.0645 (14)
C10.4737 (8)0.1904 (10)0.1573 (2)0.0713 (14)
H1A0.35390.31410.15890.086*
C20.6439 (8)0.1902 (11)0.2021 (2)0.0775 (15)
H2B0.63900.31430.23280.093*
C30.8199 (8)0.0054 (10)0.2008 (2)0.0754 (15)
H3A0.93380.00020.23080.090*
C40.8234 (8)0.1703 (10)0.1543 (2)0.0713 (14)
C50.6570 (7)0.1786 (10)0.1093 (2)0.0662 (12)
H5A0.66380.30630.07940.079*
C60.4775 (7)0.0088 (9)0.1096 (2)0.0610 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F0.0714 (18)0.100 (2)0.128 (3)0.0319 (18)0.0243 (17)0.001 (2)
O10.090 (2)0.0527 (19)0.094 (3)0.0071 (18)0.044 (2)0.0045 (19)
O20.080 (2)0.0468 (18)0.104 (3)0.0053 (17)0.0424 (19)0.0032 (19)
B0.061 (3)0.049 (3)0.083 (4)0.001 (2)0.022 (3)0.002 (3)
C10.063 (3)0.057 (3)0.094 (4)0.002 (2)0.023 (2)0.003 (3)
C20.072 (3)0.072 (3)0.088 (3)0.001 (3)0.021 (3)0.013 (3)
C30.064 (3)0.071 (3)0.090 (4)0.005 (3)0.035 (3)0.004 (3)
C40.055 (3)0.064 (3)0.094 (4)0.008 (2)0.015 (2)0.011 (3)
C50.061 (3)0.062 (3)0.075 (3)0.006 (2)0.014 (2)0.002 (2)
C60.056 (2)0.050 (2)0.076 (3)0.001 (2)0.017 (2)0.006 (2)
Geometric parameters (Å, º) top
F—C41.377 (5)C1—H1A0.9300
O1—B1.343 (6)C2—C31.375 (7)
O1—H10.851 (19)C2—H2B0.9300
O2—B1.366 (6)C3—C41.365 (7)
O2—H20.855 (19)C3—H3A0.9300
B—C61.562 (6)C4—C51.377 (6)
C1—C21.387 (6)C5—C61.398 (6)
C1—C61.406 (6)C5—H5A0.9300
B—O1—H1116 (4)C4—C3—H3A120.8
B—O2—H2124 (4)C2—C3—H3A120.8
O1—B—O2118.2 (4)C3—C4—C5123.9 (4)
O1—B—C6119.0 (4)C3—C4—F118.1 (4)
O2—B—C6122.7 (4)C5—C4—F118.0 (5)
C2—C1—C6121.8 (5)C4—C5—C6118.6 (5)
C2—C1—H1A119.1C4—C5—H5A120.7
C6—C1—H1A119.1C6—C5—H5A120.7
C3—C2—C1119.7 (5)C5—C6—C1117.6 (4)
C3—C2—H2B120.2C5—C6—B120.1 (4)
C1—C2—H2B120.2C1—C6—B122.1 (4)
C4—C3—C2118.4 (4)
C6—C1—C2—C31.1 (8)C4—C5—C6—B178.0 (5)
C1—C2—C3—C41.2 (8)C2—C1—C6—C51.5 (7)
C2—C3—C4—C51.9 (8)C2—C1—C6—B177.4 (5)
C2—C3—C4—F179.5 (5)O1—B—C6—C523.3 (7)
C3—C4—C5—C62.4 (8)O2—B—C6—C5156.1 (5)
F—C4—C5—C6179.0 (4)O1—B—C6—C1152.5 (5)
C4—C5—C6—C12.1 (7)O2—B—C6—C128.1 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.85 (3)2.06 (4)2.796 (5)144 (4)
O2—H2···O1ii0.86 (3)2.08 (3)2.831 (5)145 (4)
Symmetry codes: (i) x, y, z; (ii) x, y+1, z.
 

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