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The title compound, C13H11BBrFO3, exists as an almost centrosymmetric dimer of two crystallographically independent molecules linked by hydrogen bonds. The B(OH)2 groups are slightly twisted from the plane of the benzene ring. There are intra- and inter­molecular hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806007720/bt2019sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806007720/bt2019Isup2.hkl
Contains datablock I

CCDC reference: 605232

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.049
  • wR factor = 0.113
  • Data-to-parameter ratio = 13.0

checkCIF/PLATON results

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Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.23 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8 PLAT480_ALERT_4_C Long H...A H-Bond Reported H2O' .. F1' .. 2.59 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2001); cell refinement: CrysAlis RED (Oxford Diffraction, 2001); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXL97.

3-Bromo-2-(2-fluorobenzyloxy)phenylboronic acid top
Crystal data top
C13H11BBrFO3F(000) = 648
Mr = 324.94Dx = 1.678 Mg m3
Triclinic, P1Melting point = 112.0–114.0 K
a = 4.0226 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 15.278 (2) ÅCell parameters from 10000 reflections
c = 21.685 (3) Åθ = 1.5–29.7°
α = 105.084 (11)°µ = 3.21 mm1
β = 90.026 (10)°T = 100 K
γ = 92.089 (11)°Needle, colourless
V = 1285.9 (3) Å30.53 × 0.07 × 0.05 mm
Z = 4
Data collection top
Oxford Diffraction KM-4-CCD
diffractometer
4521 independent reflections
Radiation source: fine-focus sealed tube2963 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.076
Detector resolution: 1024 pixels mm-1θmax = 25.0°, θmin = 2.9°
ω scansh = 44
Absorption correction: numerical
(CrysAlis RED; Oxford Diffraction, 2001)
k = 1818
Tmin = 0.522, Tmax = 0.857l = 2525
13268 measured reflections
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H-atom parameters constrained
S = 0.92 w = 1/[σ2(Fo2) + (0.05P)2]
where P = (Fo2 + 2Fc2)/3
4521 reflections(Δ/σ)max = 0.014
347 parametersΔρmax = 1.66 e Å3
156 restraintsΔρmin = 0.74 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
Br10.66925 (13)0.45022 (3)0.17811 (3)0.01804 (17)
Br1'0.16302 (13)0.52661 (4)0.32487 (3)0.02040 (17)
F10.4200 (9)0.0743 (2)0.18014 (16)0.0343 (9)
F1'0.0198 (9)0.9072 (2)0.30262 (17)0.0383 (9)
O10.0635 (10)0.1027 (2)0.0356 (2)0.0309 (10)
H1O0.09350.04660.04050.046*
O20.2289 (10)0.0821 (2)0.05303 (18)0.0230 (9)
H2O0.34580.11240.08380.035*
O30.4967 (8)0.2460 (2)0.13364 (17)0.0156 (8)
O1'0.1992 (10)0.9085 (2)0.53907 (18)0.0266 (10)
H1O'0.17490.96440.54210.040*
O2'0.0710 (10)0.9050 (2)0.44218 (18)0.0257 (10)
H2O'0.12400.86710.40840.039*
O3'0.1281 (8)0.7336 (2)0.36124 (17)0.0160 (8)
C10.4484 (12)0.3843 (3)0.1014 (3)0.0169 (12)
C20.3447 (12)0.4307 (3)0.0581 (3)0.0157 (12)
H20.38570.49430.06630.019*
C30.1820 (12)0.3832 (3)0.0034 (3)0.0179 (13)
H30.11060.41440.02650.021*
C40.1202 (12)0.2908 (3)0.0090 (3)0.0147 (12)
H40.00810.25940.04740.018*
C50.2195 (13)0.2427 (3)0.0340 (3)0.0148 (12)
C60.3826 (13)0.2914 (3)0.0902 (3)0.0164 (12)
C70.2811 (12)0.2550 (4)0.1890 (2)0.0160 (12)
H7A0.07770.21570.17700.019*
H7B0.21420.31860.20490.019*
C80.4709 (12)0.2272 (3)0.2399 (3)0.0154 (12)
C90.5897 (13)0.2886 (4)0.2952 (3)0.0184 (13)
H90.55890.35150.30050.022*
C100.7514 (13)0.2610 (4)0.3430 (3)0.0230 (14)
H100.82700.30460.38050.028*
C110.8026 (13)0.1700 (4)0.3357 (3)0.0214 (13)
H110.91490.15090.36820.026*
C120.6902 (14)0.1070 (4)0.2812 (3)0.0262 (15)
H120.72180.04410.27590.031*
C130.5319 (14)0.1370 (4)0.2349 (3)0.0233 (14)
C1'0.0120 (12)0.6037 (3)0.4000 (3)0.0167 (12)
C2'0.1468 (12)0.5645 (4)0.4457 (3)0.0174 (13)
H2'0.15560.50050.43890.021*
C3'0.2695 (12)0.6206 (4)0.5018 (3)0.0191 (13)
H3'0.36480.59460.53330.023*
C4'0.2530 (13)0.7140 (4)0.5118 (3)0.0185 (13)
H4'0.33380.75140.55060.022*
C5'0.1190 (13)0.7543 (4)0.4656 (3)0.0176 (13)
C6'0.0042 (12)0.6967 (3)0.4093 (3)0.0146 (12)
C7'0.1098 (12)0.7277 (4)0.3086 (3)0.0185 (13)
H7A'0.29440.76890.32340.022*
H7B'0.20430.66490.29340.022*
C8'0.0713 (12)0.7541 (3)0.2561 (3)0.0146 (12)
C9'0.2103 (12)0.6894 (4)0.2059 (3)0.0181 (13)
H9'0.19680.62730.20610.022*
C10'0.3669 (13)0.7142 (4)0.1559 (3)0.0226 (14)
H10'0.45770.66920.12190.027*
C11'0.3911 (13)0.8045 (4)0.1555 (3)0.0251 (14)
H11'0.49940.82170.12130.030*
C12'0.2584 (14)0.8698 (4)0.2048 (3)0.0289 (15)
H12'0.27260.93190.20470.035*
C13'0.1056 (14)0.8432 (4)0.2537 (3)0.0221 (13)
B10.1266 (16)0.1378 (4)0.0167 (3)0.0189 (15)
B1'0.0826 (16)0.8609 (4)0.4818 (3)0.0176 (14)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0163 (3)0.0166 (3)0.0190 (3)0.0009 (2)0.0001 (2)0.0007 (2)
Br1'0.0201 (3)0.0183 (3)0.0203 (3)0.0036 (2)0.0013 (3)0.0002 (2)
F10.059 (2)0.0155 (17)0.027 (2)0.0038 (16)0.0161 (18)0.0044 (16)
F1'0.061 (3)0.0241 (19)0.031 (2)0.0093 (17)0.0081 (19)0.0076 (17)
O10.043 (3)0.020 (2)0.029 (3)0.007 (2)0.016 (2)0.005 (2)
O20.040 (3)0.015 (2)0.014 (2)0.0024 (17)0.0088 (19)0.0046 (17)
O30.018 (2)0.0163 (19)0.015 (2)0.0055 (15)0.0066 (17)0.0076 (16)
O1'0.044 (3)0.016 (2)0.019 (2)0.0006 (19)0.011 (2)0.0028 (18)
O2'0.043 (3)0.017 (2)0.016 (2)0.0028 (19)0.006 (2)0.0013 (18)
O3'0.019 (2)0.021 (2)0.010 (2)0.0001 (16)0.0018 (16)0.0067 (16)
C10.010 (3)0.019 (3)0.020 (3)0.001 (2)0.004 (2)0.003 (2)
C20.011 (3)0.010 (3)0.026 (3)0.003 (2)0.001 (2)0.004 (2)
C30.011 (3)0.012 (3)0.030 (4)0.004 (2)0.002 (3)0.005 (3)
C40.012 (3)0.023 (3)0.010 (3)0.002 (2)0.000 (2)0.007 (2)
C50.018 (3)0.018 (3)0.009 (3)0.001 (2)0.006 (2)0.004 (2)
C60.016 (3)0.020 (3)0.017 (3)0.004 (2)0.008 (2)0.011 (3)
C70.011 (3)0.028 (3)0.012 (3)0.001 (2)0.002 (2)0.011 (3)
C80.012 (3)0.022 (3)0.014 (3)0.000 (2)0.004 (2)0.009 (2)
C90.019 (3)0.018 (3)0.019 (3)0.006 (2)0.006 (3)0.005 (3)
C100.020 (3)0.033 (3)0.017 (3)0.001 (3)0.002 (3)0.009 (3)
C110.018 (3)0.036 (4)0.015 (3)0.002 (3)0.004 (3)0.014 (3)
C120.030 (4)0.019 (3)0.036 (4)0.004 (3)0.000 (3)0.018 (3)
C130.026 (3)0.029 (3)0.016 (3)0.003 (3)0.000 (3)0.008 (3)
C1'0.010 (3)0.019 (3)0.019 (3)0.003 (2)0.003 (2)0.001 (2)
C2'0.018 (3)0.019 (3)0.014 (3)0.003 (2)0.003 (3)0.004 (2)
C3'0.012 (3)0.022 (3)0.029 (4)0.003 (2)0.006 (3)0.017 (3)
C4'0.014 (3)0.032 (3)0.009 (3)0.003 (2)0.000 (2)0.006 (3)
C5'0.014 (3)0.021 (3)0.016 (3)0.002 (2)0.000 (2)0.003 (3)
C6'0.009 (3)0.020 (3)0.015 (3)0.000 (2)0.002 (2)0.005 (2)
C7'0.008 (3)0.031 (3)0.017 (3)0.006 (2)0.001 (2)0.006 (3)
C8'0.009 (3)0.022 (3)0.014 (3)0.002 (2)0.003 (2)0.008 (2)
C9'0.012 (3)0.027 (3)0.016 (3)0.002 (2)0.002 (2)0.009 (3)
C10'0.023 (3)0.038 (4)0.007 (3)0.003 (3)0.004 (3)0.005 (3)
C11'0.019 (3)0.045 (4)0.013 (3)0.002 (3)0.003 (3)0.012 (3)
C12'0.032 (4)0.025 (3)0.035 (4)0.009 (3)0.005 (3)0.017 (3)
C13'0.025 (3)0.022 (3)0.021 (3)0.001 (3)0.001 (3)0.008 (3)
B10.022 (4)0.021 (3)0.015 (4)0.002 (3)0.001 (3)0.007 (3)
B1'0.021 (4)0.022 (3)0.013 (4)0.005 (3)0.001 (3)0.010 (3)
Geometric parameters (Å, º) top
Br1—C11.906 (6)C9—C101.385 (7)
Br1'—C1'1.897 (5)C9—H90.9500
F1—C131.381 (6)C10—C111.381 (7)
F1'—C13'1.353 (6)C10—H100.9500
O1—B11.346 (7)C11—C121.380 (8)
O1—H1O0.8400C11—H110.9500
O2—B11.375 (7)C12—C131.373 (8)
O2—H2O0.8400C12—H120.9500
O3—C61.394 (6)C1'—C6'1.381 (7)
O3—C71.461 (6)C1'—C2'1.386 (7)
O1'—B1'1.358 (7)C2'—C3'1.395 (7)
O1'—H1O'0.8400C2'—H2'0.9500
O2'—B1'1.359 (7)C3'—C4'1.386 (7)
O2'—H2O'0.8400C3'—H3'0.9500
O3'—C6'1.403 (6)C4'—C5'1.404 (7)
O3'—C7'1.471 (6)C4'—H4'0.9500
C1—C21.386 (7)C5'—C6'1.397 (7)
C1—C61.391 (7)C5'—B1'1.575 (8)
C2—C31.371 (7)C7'—C8'1.487 (7)
C2—H20.9500C7'—H7A'0.9900
C3—C41.379 (7)C7'—H7B'0.9900
C3—H30.9500C8'—C13'1.377 (7)
C4—C51.394 (7)C8'—C9'1.398 (7)
C4—H40.9500C9'—C10'1.382 (7)
C5—C61.401 (7)C9'—H9'0.9500
C5—B11.579 (8)C10'—C11'1.382 (8)
C7—C81.499 (7)C10'—H10'0.9500
C7—H7A0.9900C11'—C12'1.380 (8)
C7—H7B0.9900C11'—H11'0.9500
C8—C131.386 (7)C12'—C13'1.370 (8)
C8—C91.389 (7)C12'—H12'0.9500
B1—O1—H1O109.5C6'—C1'—C2'120.6 (5)
B1—O2—H2O109.5C6'—C1'—Br1'121.0 (4)
C6—O3—C7113.0 (4)C2'—C1'—Br1'118.3 (4)
B1'—O1'—H1O'109.5C1'—C2'—C3'118.9 (5)
B1'—O2'—H2O'109.5C1'—C2'—H2'120.5
C6'—O3'—C7'112.5 (4)C3'—C2'—H2'120.5
C2—C1—C6120.7 (5)C4'—C3'—C2'120.4 (5)
C2—C1—Br1119.1 (4)C4'—C3'—H3'119.8
C6—C1—Br1120.1 (4)C2'—C3'—H3'119.8
C3—C2—C1118.9 (5)C3'—C4'—C5'121.1 (5)
C3—C2—H2120.6C3'—C4'—H4'119.5
C1—C2—H2120.6C5'—C4'—H4'119.5
C2—C3—C4121.1 (5)C6'—C5'—C4'117.5 (5)
C2—C3—H3119.4C6'—C5'—B1'123.7 (5)
C4—C3—H3119.4C4'—C5'—B1'118.7 (5)
C3—C4—C5121.1 (5)C1'—C6'—C5'121.5 (5)
C3—C4—H4119.5C1'—C6'—O3'118.9 (5)
C5—C4—H4119.5C5'—C6'—O3'119.7 (4)
C4—C5—C6117.8 (5)O3'—C7'—C8'108.0 (4)
C4—C5—B1117.3 (5)O3'—C7'—H7A'110.1
C6—C5—B1124.9 (5)C8'—C7'—H7A'110.1
C1—C6—O3119.6 (5)O3'—C7'—H7B'110.1
C1—C6—C5120.4 (5)C8'—C7'—H7B'110.1
O3—C6—C5119.9 (4)H7A'—C7'—H7B'108.4
O3—C7—C8108.1 (4)C13'—C8'—C9'116.7 (5)
O3—C7—H7A110.1C13'—C8'—C7'121.8 (5)
C8—C7—H7A110.1C9'—C8'—C7'121.5 (5)
O3—C7—H7B110.1C10'—C9'—C8'121.2 (5)
C8—C7—H7B110.1C10'—C9'—H9'119.4
H7A—C7—H7B108.4C8'—C9'—H9'119.4
C13—C8—C9115.6 (5)C11'—C10'—C9'119.8 (5)
C13—C8—C7121.3 (5)C11'—C10'—H10'120.1
C9—C8—C7123.1 (5)C9'—C10'—H10'120.1
C10—C9—C8122.1 (5)C12'—C11'—C10'120.2 (5)
C10—C9—H9119.0C12'—C11'—H11'119.9
C8—C9—H9119.0C10'—C11'—H11'119.9
C11—C10—C9119.8 (6)C13'—C12'—C11'118.7 (5)
C11—C10—H10120.1C13'—C12'—H12'120.6
C9—C10—H10120.1C11'—C12'—H12'120.6
C12—C11—C10119.9 (5)F1'—C13'—C12'118.9 (5)
C12—C11—H11120.1F1'—C13'—C8'117.7 (5)
C10—C11—H11120.1C12'—C13'—C8'123.4 (5)
C13—C12—C11118.6 (5)O1—B1—O2119.4 (5)
C13—C12—H12120.7O1—B1—C5117.9 (5)
C11—C12—H12120.7O2—B1—C5122.7 (5)
C12—C13—F1118.9 (5)O1'—B1'—O2'120.1 (5)
C12—C13—C8124.0 (6)O1'—B1'—C5'117.4 (5)
F1—C13—C8117.1 (5)O2'—B1'—C5'122.4 (5)
C6—C1—C2—C31.4 (8)C3'—C4'—C5'—C6'0.2 (8)
Br1—C1—C2—C3179.1 (4)C3'—C4'—C5'—B1'175.5 (5)
C1—C2—C3—C40.2 (8)C2'—C1'—C6'—C5'2.5 (8)
C2—C3—C4—C50.4 (8)Br1'—C1'—C6'—C5'177.1 (4)
C3—C4—C5—C60.3 (7)C2'—C1'—C6'—O3'178.7 (5)
C3—C4—C5—B1178.0 (5)Br1'—C1'—C6'—O3'1.6 (7)
C2—C1—C6—O3178.4 (4)C4'—C5'—C6'—C1'2.0 (8)
Br1—C1—C6—O33.8 (6)B1'—C5'—C6'—C1'173.4 (5)
C2—C1—C6—C52.0 (8)C4'—C5'—C6'—O3'179.2 (4)
Br1—C1—C6—C5179.8 (4)B1'—C5'—C6'—O3'5.4 (8)
C7—O3—C6—C181.5 (6)C7'—O3'—C6'—C1'79.9 (6)
C7—O3—C6—C5102.1 (5)C7'—O3'—C6'—C5'101.3 (5)
C4—C5—C6—C11.5 (7)C6'—O3'—C7'—C8'170.8 (4)
B1—C5—C6—C1179.0 (5)O3'—C7'—C8'—C13'87.3 (6)
C4—C5—C6—O3177.8 (4)O3'—C7'—C8'—C9'93.9 (6)
B1—C5—C6—O34.7 (8)C13'—C8'—C9'—C10'1.5 (8)
C6—O3—C7—C8164.3 (4)C7'—C8'—C9'—C10'177.4 (5)
O3—C7—C8—C1373.5 (6)C8'—C9'—C10'—C11'0.8 (8)
O3—C7—C8—C9108.1 (5)C9'—C10'—C11'—C12'0.2 (8)
C13—C8—C9—C101.5 (8)C10'—C11'—C12'—C13'0.5 (9)
C7—C8—C9—C10177.0 (5)C11'—C12'—C13'—F1'178.9 (5)
C8—C9—C10—C110.9 (8)C11'—C12'—C13'—C8'1.3 (9)
C9—C10—C11—C120.5 (8)C9'—C8'—C13'—F1'178.4 (5)
C10—C11—C12—C130.7 (8)C7'—C8'—C13'—F1'2.7 (8)
C11—C12—C13—F1179.8 (5)C9'—C8'—C13'—C12'1.7 (8)
C11—C12—C13—C81.4 (9)C7'—C8'—C13'—C12'177.2 (5)
C9—C8—C13—C121.7 (8)C4—C5—B1—O14.9 (8)
C7—C8—C13—C12176.8 (5)C6—C5—B1—O1172.5 (5)
C9—C8—C13—F1179.4 (5)C4—C5—B1—O2175.7 (5)
C7—C8—C13—F12.1 (8)C6—C5—B1—O26.8 (9)
C6'—C1'—C2'—C3'1.1 (8)C6'—C5'—B1'—O1'178.6 (5)
Br1'—C1'—C2'—C3'178.6 (4)C4'—C5'—B1'—O1'3.2 (8)
C1'—C2'—C3'—C4'0.7 (8)C6'—C5'—B1'—O2'1.3 (9)
C2'—C3'—C4'—C5'1.2 (8)C4'—C5'—B1'—O2'174.1 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···O2i0.841.972.803 (5)172
O2—H2O···O30.842.112.830 (5)143
O2—H2O···F10.842.332.895 (5)125
O1—H1O···O2ii0.841.972.800 (5)172
O2—H2O···O30.842.032.764 (5)146
O2—H2O···F10.842.593.057 (5)116
Symmetry codes: (i) x, y, z; (ii) x, y+2, z+1.
 

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