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The molecule of the title compound, C5H5BO4, is almost planar with the boronic acid group inclined to the furan ring by 3.7 (1)°. DFT (density functional theory) calculations at the B3LYP/6-311+G** level of theory (with no imaginary frequencies) were used to approximate the influence of hydrogen bonding on the molecular geometry and have confirmed the planarity of the mol­ecule. No significant differences in geometrical parameters in the solid state and in the gas phase are associated with the presence of the O—H...O intermolecular hydrogen-bonding network. The crystal packing is characterized by O—H...O hydrogen-bonded dimers, which are additionally linked by O—H...O, as well as C—H...O interactions, resulting in the formation of a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804023293/su6141sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804023293/su6141Isup2.hkl
Contains datablock I

CCDC reference: 255863

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.043
  • wR factor = 0.106
  • Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.34
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2002); cell refinement: CrysAlis RED (Oxford Diffraction, 2002); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

3-Formyl-2-furanboronic acid top
Crystal data top
C5H5BO4F(000) = 288
Mr = 139.90Dx = 1.572 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4208 reflections
a = 3.660 (1) Åθ = 3.4–28.0°
b = 14.252 (2) ŵ = 0.13 mm1
c = 11.447 (1) ÅT = 100 K
β = 98.09 (1)°Irregular, colourless
V = 591.16 (19) Å30.20 × 0.15 × 0.15 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur
diffractometer
1143 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.031
Graphite monochromatorθmax = 28.0°, θmin = 3.4°
Detector resolution: 1024 x 1024 with blocks 2 x 2 pixels mm-1h = 44
ω scansk = 1818
4208 measured reflectionsl = 1512
1419 independent 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)] = 0.043Hydrogen site location: difference Fourier map
wR(F2) = 0.106All H-atom parameters refined
S = 1.08 w = 1/[σ2(Fo2) + (0.042P)2 + 0.3322P]
where P = (Fo2 + 2Fc2)/3
1419 reflections(Δ/σ)max < 0.001
111 parametersΔρmax = 0.25 e Å3
0 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
B10.4294 (6)0.36367 (14)0.54374 (16)0.0191 (4)
O10.2473 (4)0.39225 (9)0.43883 (11)0.0247 (3)
O20.6145 (4)0.42562 (8)0.62073 (10)0.0235 (3)
O30.0282 (4)0.10746 (8)0.33888 (10)0.0244 (3)
O40.5886 (3)0.22835 (8)0.68075 (10)0.0193 (3)
C10.4186 (4)0.25655 (11)0.57182 (14)0.0164 (3)
C20.2791 (5)0.17848 (11)0.51102 (14)0.0164 (3)
C30.3662 (5)0.09897 (12)0.58586 (15)0.0217 (4)
C40.5540 (5)0.13251 (12)0.68638 (15)0.0220 (4)
C50.0887 (5)0.17870 (12)0.39080 (14)0.0182 (4)
H10.301 (7)0.451 (2)0.421 (2)0.053 (8)*
H20.721 (7)0.4036 (18)0.689 (2)0.044 (7)*
H40.663 (5)0.1050 (13)0.7604 (17)0.021 (5)*
H30.298 (6)0.0356 (15)0.5676 (18)0.029 (5)*
H50.048 (5)0.2415 (15)0.3481 (17)0.027 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
B10.0215 (9)0.0182 (9)0.0164 (9)0.0010 (7)0.0016 (7)0.0012 (7)
O10.0366 (7)0.0164 (6)0.0173 (6)0.0052 (5)0.0088 (5)0.0023 (5)
O20.0348 (7)0.0164 (6)0.0156 (6)0.0041 (5)0.0091 (5)0.0027 (5)
O30.0331 (7)0.0182 (6)0.0187 (6)0.0038 (5)0.0074 (5)0.0018 (5)
O40.0257 (6)0.0172 (6)0.0132 (5)0.0019 (5)0.0034 (5)0.0010 (4)
C10.0169 (8)0.0194 (8)0.0118 (7)0.0009 (6)0.0016 (6)0.0017 (6)
C20.0168 (8)0.0172 (8)0.0146 (7)0.0011 (6)0.0001 (6)0.0000 (6)
C30.0274 (9)0.0161 (8)0.0194 (8)0.0027 (7)0.0038 (7)0.0010 (6)
C40.0274 (9)0.0175 (8)0.0191 (8)0.0006 (7)0.0039 (7)0.0033 (7)
C50.0193 (8)0.0176 (8)0.0165 (8)0.0004 (6)0.0019 (6)0.0001 (6)
Geometric parameters (Å, º) top
B1—O11.352 (2)C1—C21.372 (2)
B1—O21.359 (2)C2—C31.429 (2)
B1—C11.562 (3)C2—C51.452 (2)
O1—H10.89 (3)C3—C41.342 (2)
O2—H20.88 (3)C3—H30.95 (2)
O3—C51.223 (2)C4—H40.967 (19)
O4—C11.3731 (18)C5—H51.02 (2)
O4—C41.374 (2)
O1—B1—O2121.25 (16)C3—C2—C5127.34 (15)
O1—B1—C1116.99 (15)C4—C3—C2106.00 (15)
O2—B1—C1121.75 (15)C4—C3—H3127.8 (13)
B1—O1—H1113.3 (17)C2—C3—H3126.2 (13)
B1—O2—H2117.5 (17)C3—C4—O4110.69 (14)
C1—O4—C4107.49 (12)C3—C4—H4134.8 (12)
C2—C1—O4108.18 (14)O4—C4—H4114.5 (11)
C2—C1—B1134.95 (14)O3—C5—C2123.17 (15)
O4—C1—B1116.85 (13)O3—C5—H5118.5 (11)
C1—C2—C3107.64 (14)C2—C5—H5118.3 (11)
C1—C2—C5124.99 (15)
C4—O4—C1—C20.21 (18)O4—C1—C2—C5178.05 (15)
C4—O4—C1—B1178.79 (15)B1—C1—C2—C50.7 (3)
O1—B1—C1—C24.4 (3)C1—C2—C3—C40.5 (2)
O2—B1—C1—C2175.31 (19)C5—C2—C3—C4177.68 (17)
O1—B1—C1—O4176.94 (15)C2—C3—C4—O40.6 (2)
O2—B1—C1—O43.4 (2)C1—O4—C4—C30.5 (2)
O4—C1—C2—C30.15 (19)C1—C2—C5—O3179.09 (17)
B1—C1—C2—C3178.89 (19)C3—C2—C5—O31.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O40.88 (3)2.54 (3)2.899 (2)105 (2)
C5—H5···O11.02 (2)2.45 (2)3.133 (2)123 (1)
O1—H1···O2i0.89 (3)1.86 (3)2.749 (2)177 (3)
O2—H2···O3ii0.88 (3)1.84 (3)2.693 (2)164 (2)
C3—H3···O3iii0.95 (2)2.56 (2)3.351 (2)140 (2)
C5—H5···O4iv1.02 (2)2.40 (2)3.106 (2)125 (1)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y+1/2, z+1/2; (iii) x, y, z+1; (iv) x1, y+1/2, z1/2.
Selected geometric data (Å, °) for (I) top
X–rayDFT
B1–O11.352 (2)1.363
B1–O21.359 (2)1.365
B1–C11.562 (3)1.558
O3–C51.223 (2)1.214
O4–C11.373 (2)1.375
O4–C41.374 (2)1.366
C1–C21.372 (2)1.378
C2–C31.429 (2)1.435
C2–C51.452 (2)1.471
C3–C41.342 (2)1.355
O1–B1–O2121.3 (2)119.87
O1–B1–C1117.0 (2)119.04
O2–B1–C1121.8 (2)121.13
C1–O4–C4107.5 (1)107.99
C2–C1–O4108.2 (1)108.25
C2–C1–B1135.0 (1)136.09
O4–C1–B1116.9 (1)115.65
C1–C2–C3107.6 (1)107.21
C1–C2–C5125.0 (2)126.55
C3–C2–C5127.3 (2)126.24
C4–C3–C2106.0 (2)105.99
C3–C4–O4110.7 (1)110.56
O3–C5–C2123.2 (2)123.03
O1–B1–C1–C24.4 (3)0.00
O2–B1–C1–C2-175.3 (2)-180.00
O1–B1–C1–O4-176.9 (2)-180.00
O2–B1–C1–O43.4 (2)0.00
 

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