3-Fluoro­phenyl­boronic acid

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.

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

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Computing details

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

Crystal data

C6H6BFO2	F(000) = 288
Mr = 139.92	Dx = 1.434 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 5.7560 (12) Å	θ = 10–12°
b = 5.027 (1) Å	µ = 0.12 mm^−1
c = 22.402 (5) Å	T = 294 K
β = 91.19 (3)°	Block, white
V = 648.1 (2) Å^3	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer	868 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 26.0°, θmin = 1.8°
ω/2θ scans	h = −7→7
Absorption correction: ψ scan (North et al., 1968)	k = 0→6
Tmin = 0.965, Tmax = 0.988	l = 0→27
1265 measured reflections	3 standard reflections every 120 min
1265 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.084	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.189	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ^2(Fo^2) + (0.03P)^2 + 2P] where P = (Fo^2 + 2Fc^2)/3
1265 reflections	(Δ/σ)max < 0.001
97 parameters	Δρmax = 0.23 e Å^−3
2 restraints	Δρmin = −0.21 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
F	1.0010 (5)	−0.3535 (7)	0.15299 (15)	0.1001 (12)
O1	0.2372 (6)	−0.2302 (7)	0.03199 (16)	0.0796 (11)
H1	0.168 (8)	−0.216 (11)	−0.0018 (13)	0.091*
O2	0.1524 (6)	0.2182 (6)	0.04460 (17)	0.0776 (11)
H2	0.183 (9)	0.376 (5)	0.057 (2)	0.091*
B	0.2811 (9)	0.0000 (11)	0.0604 (3)	0.0645 (14)
C1	0.4737 (8)	0.1904 (10)	0.1573 (2)	0.0713 (14)
H1A	0.3539	0.3141	0.1589	0.086*
C2	0.6439 (8)	0.1902 (11)	0.2021 (2)	0.0775 (15)
H2B	0.6390	0.3143	0.2328	0.093*
C3	0.8199 (8)	0.0054 (10)	0.2008 (2)	0.0754 (15)
H3A	0.9338	0.0002	0.2308	0.090*
C4	0.8234 (8)	−0.1703 (10)	0.1543 (2)	0.0713 (14)
C5	0.6570 (7)	−0.1786 (10)	0.1093 (2)	0.0662 (12)
H5A	0.6638	−0.3063	0.0794	0.079*
C6	0.4775 (7)	0.0088 (9)	0.1096 (2)	0.0610 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F	0.0714 (18)	0.100 (2)	0.128 (3)	0.0319 (18)	−0.0243 (17)	0.001 (2)
O1	0.090 (2)	0.0527 (19)	0.094 (3)	0.0071 (18)	−0.044 (2)	−0.0045 (19)
O2	0.080 (2)	0.0468 (18)	0.104 (3)	0.0053 (17)	−0.0424 (19)	−0.0032 (19)
B	0.061 (3)	0.049 (3)	0.083 (4)	−0.001 (2)	−0.022 (3)	0.002 (3)
C1	0.063 (3)	0.057 (3)	0.094 (4)	0.002 (2)	−0.023 (2)	−0.003 (3)
C2	0.072 (3)	0.072 (3)	0.088 (3)	−0.001 (3)	−0.021 (3)	−0.013 (3)
C3	0.064 (3)	0.071 (3)	0.090 (4)	−0.005 (3)	−0.035 (3)	0.004 (3)
C4	0.055 (3)	0.064 (3)	0.094 (4)	0.008 (2)	−0.015 (2)	0.011 (3)
C5	0.061 (3)	0.062 (3)	0.075 (3)	0.006 (2)	−0.014 (2)	−0.002 (2)
C6	0.056 (2)	0.050 (2)	0.076 (3)	−0.001 (2)	−0.017 (2)	0.006 (2)

Geometric parameters (Å, º)

F—C4	1.377 (5)	C1—H1A	0.9300
O1—B	1.343 (6)	C2—C3	1.375 (7)
O1—H1	0.851 (19)	C2—H2B	0.9300
O2—B	1.366 (6)	C3—C4	1.365 (7)
O2—H2	0.855 (19)	C3—H3A	0.9300
B—C6	1.562 (6)	C4—C5	1.377 (6)
C1—C2	1.387 (6)	C5—C6	1.398 (6)
C1—C6	1.406 (6)	C5—H5A	0.9300
B—O1—H1	116 (4)	C4—C3—H3A	120.8
B—O2—H2	124 (4)	C2—C3—H3A	120.8
O1—B—O2	118.2 (4)	C3—C4—C5	123.9 (4)
O1—B—C6	119.0 (4)	C3—C4—F	118.1 (4)
O2—B—C6	122.7 (4)	C5—C4—F	118.0 (5)
C2—C1—C6	121.8 (5)	C4—C5—C6	118.6 (5)
C2—C1—H1A	119.1	C4—C5—H5A	120.7
C6—C1—H1A	119.1	C6—C5—H5A	120.7
C3—C2—C1	119.7 (5)	C5—C6—C1	117.6 (4)
C3—C2—H2B	120.2	C5—C6—B	120.1 (4)
C1—C2—H2B	120.2	C1—C6—B	122.1 (4)
C4—C3—C2	118.4 (4)
C6—C1—C2—C3	−1.1 (8)	C4—C5—C6—B	−178.0 (5)
C1—C2—C3—C4	1.2 (8)	C2—C1—C6—C5	1.5 (7)
C2—C3—C4—C5	−1.9 (8)	C2—C1—C6—B	177.4 (5)
C2—C3—C4—F	179.5 (5)	O1—B—C6—C5	23.3 (7)
C3—C4—C5—C6	2.4 (8)	O2—B—C6—C5	−156.1 (5)
F—C4—C5—C6	−179.0 (4)	O1—B—C6—C1	−152.5 (5)
C4—C5—C6—C1	−2.1 (7)	O2—B—C6—C1	28.1 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	0.85 (3)	2.06 (4)	2.796 (5)	144 (4)
O2—H2···O1^ii	0.86 (3)	2.08 (3)	2.831 (5)	145 (4)

Symmetry codes: (i) −x, −y, −z; (ii) x, y+1, z.