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The molecule of the title compound, C
5H
5BO
4, 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
CCDC reference: 255863
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (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
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
C5H5BO4 | F(000) = 288 |
Mr = 139.90 | Dx = 1.572 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4208 reflections |
a = 3.660 (1) Å | θ = 3.4–28.0° |
b = 14.252 (2) Å | µ = 0.13 mm−1 |
c = 11.447 (1) Å | T = 100 K |
β = 98.09 (1)° | Irregular, colourless |
V = 591.16 (19) Å3 | 0.20 × 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 tube | Rint = 0.031 |
Graphite monochromator | θmax = 28.0°, θmin = 3.4° |
Detector resolution: 1024 x 1024 with blocks 2 x 2 pixels mm-1 | h = −4→4 |
ω scans | k = −18→18 |
4208 measured reflections | l = −15→12 |
1419 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.043 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.106 | All 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 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
B1 | 0.4294 (6) | 0.36367 (14) | 0.54374 (16) | 0.0191 (4) | |
O1 | 0.2473 (4) | 0.39225 (9) | 0.43883 (11) | 0.0247 (3) | |
O2 | 0.6145 (4) | 0.42562 (8) | 0.62073 (10) | 0.0235 (3) | |
O3 | −0.0282 (4) | 0.10746 (8) | 0.33888 (10) | 0.0244 (3) | |
O4 | 0.5886 (3) | 0.22835 (8) | 0.68075 (10) | 0.0193 (3) | |
C1 | 0.4186 (4) | 0.25655 (11) | 0.57182 (14) | 0.0164 (3) | |
C2 | 0.2791 (5) | 0.17848 (11) | 0.51102 (14) | 0.0164 (3) | |
C3 | 0.3662 (5) | 0.09897 (12) | 0.58586 (15) | 0.0217 (4) | |
C4 | 0.5540 (5) | 0.13251 (12) | 0.68638 (15) | 0.0220 (4) | |
C5 | 0.0887 (5) | 0.17870 (12) | 0.39080 (14) | 0.0182 (4) | |
H1 | 0.301 (7) | 0.451 (2) | 0.421 (2) | 0.053 (8)* | |
H2 | 0.721 (7) | 0.4036 (18) | 0.689 (2) | 0.044 (7)* | |
H4 | 0.663 (5) | 0.1050 (13) | 0.7604 (17) | 0.021 (5)* | |
H3 | 0.298 (6) | 0.0356 (15) | 0.5676 (18) | 0.029 (5)* | |
H5 | 0.048 (5) | 0.2415 (15) | 0.3481 (17) | 0.027 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
B1 | 0.0215 (9) | 0.0182 (9) | 0.0164 (9) | −0.0010 (7) | −0.0016 (7) | 0.0012 (7) |
O1 | 0.0366 (7) | 0.0164 (6) | 0.0173 (6) | −0.0052 (5) | −0.0088 (5) | 0.0023 (5) |
O2 | 0.0348 (7) | 0.0164 (6) | 0.0156 (6) | −0.0041 (5) | −0.0091 (5) | 0.0027 (5) |
O3 | 0.0331 (7) | 0.0182 (6) | 0.0187 (6) | −0.0038 (5) | −0.0074 (5) | −0.0018 (5) |
O4 | 0.0257 (6) | 0.0172 (6) | 0.0132 (5) | −0.0019 (5) | −0.0034 (5) | 0.0010 (4) |
C1 | 0.0169 (8) | 0.0194 (8) | 0.0118 (7) | 0.0009 (6) | −0.0016 (6) | 0.0017 (6) |
C2 | 0.0168 (8) | 0.0172 (8) | 0.0146 (7) | 0.0011 (6) | 0.0001 (6) | 0.0000 (6) |
C3 | 0.0274 (9) | 0.0161 (8) | 0.0194 (8) | −0.0027 (7) | −0.0038 (7) | 0.0010 (6) |
C4 | 0.0274 (9) | 0.0175 (8) | 0.0191 (8) | −0.0006 (7) | −0.0039 (7) | 0.0033 (7) |
C5 | 0.0193 (8) | 0.0176 (8) | 0.0165 (8) | 0.0004 (6) | −0.0019 (6) | −0.0001 (6) |
Geometric parameters (Å, º) top
B1—O1 | 1.352 (2) | C1—C2 | 1.372 (2) |
B1—O2 | 1.359 (2) | C2—C3 | 1.429 (2) |
B1—C1 | 1.562 (3) | C2—C5 | 1.452 (2) |
O1—H1 | 0.89 (3) | C3—C4 | 1.342 (2) |
O2—H2 | 0.88 (3) | C3—H3 | 0.95 (2) |
O3—C5 | 1.223 (2) | C4—H4 | 0.967 (19) |
O4—C1 | 1.3731 (18) | C5—H5 | 1.02 (2) |
O4—C4 | 1.374 (2) | | |
| | | |
O1—B1—O2 | 121.25 (16) | C3—C2—C5 | 127.34 (15) |
O1—B1—C1 | 116.99 (15) | C4—C3—C2 | 106.00 (15) |
O2—B1—C1 | 121.75 (15) | C4—C3—H3 | 127.8 (13) |
B1—O1—H1 | 113.3 (17) | C2—C3—H3 | 126.2 (13) |
B1—O2—H2 | 117.5 (17) | C3—C4—O4 | 110.69 (14) |
C1—O4—C4 | 107.49 (12) | C3—C4—H4 | 134.8 (12) |
C2—C1—O4 | 108.18 (14) | O4—C4—H4 | 114.5 (11) |
C2—C1—B1 | 134.95 (14) | O3—C5—C2 | 123.17 (15) |
O4—C1—B1 | 116.85 (13) | O3—C5—H5 | 118.5 (11) |
C1—C2—C3 | 107.64 (14) | C2—C5—H5 | 118.3 (11) |
C1—C2—C5 | 124.99 (15) | | |
| | | |
C4—O4—C1—C2 | 0.21 (18) | O4—C1—C2—C5 | −178.05 (15) |
C4—O4—C1—B1 | −178.79 (15) | B1—C1—C2—C5 | 0.7 (3) |
O1—B1—C1—C2 | 4.4 (3) | C1—C2—C3—C4 | −0.5 (2) |
O2—B1—C1—C2 | −175.31 (19) | C5—C2—C3—C4 | 177.68 (17) |
O1—B1—C1—O4 | −176.94 (15) | C2—C3—C4—O4 | 0.6 (2) |
O2—B1—C1—O4 | 3.4 (2) | C1—O4—C4—C3 | −0.5 (2) |
O4—C1—C2—C3 | 0.15 (19) | C1—C2—C5—O3 | 179.09 (17) |
B1—C1—C2—C3 | 178.89 (19) | C3—C2—C5—O3 | 1.2 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O4 | 0.88 (3) | 2.54 (3) | 2.899 (2) | 105 (2) |
C5—H5···O1 | 1.02 (2) | 2.45 (2) | 3.133 (2) | 123 (1) |
O1—H1···O2i | 0.89 (3) | 1.86 (3) | 2.749 (2) | 177 (3) |
O2—H2···O3ii | 0.88 (3) | 1.84 (3) | 2.693 (2) | 164 (2) |
C3—H3···O3iii | 0.95 (2) | 2.56 (2) | 3.351 (2) | 140 (2) |
C5—H5···O4iv | 1.02 (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) x−1, −y+1/2, z−1/2. |
Selected geometric data (Å, °) for (I) top | X–ray | DFT |
B1–O1 | 1.352 (2) | 1.363 |
B1–O2 | 1.359 (2) | 1.365 |
B1–C1 | 1.562 (3) | 1.558 |
O3–C5 | 1.223 (2) | 1.214 |
O4–C1 | 1.373 (2) | 1.375 |
O4–C4 | 1.374 (2) | 1.366 |
C1–C2 | 1.372 (2) | 1.378 |
C2–C3 | 1.429 (2) | 1.435 |
C2–C5 | 1.452 (2) | 1.471 |
C3–C4 | 1.342 (2) | 1.355 |
| | |
O1–B1–O2 | 121.3 (2) | 119.87 |
O1–B1–C1 | 117.0 (2) | 119.04 |
O2–B1–C1 | 121.8 (2) | 121.13 |
C1–O4–C4 | 107.5 (1) | 107.99 |
C2–C1–O4 | 108.2 (1) | 108.25 |
C2–C1–B1 | 135.0 (1) | 136.09 |
O4–C1–B1 | 116.9 (1) | 115.65 |
C1–C2–C3 | 107.6 (1) | 107.21 |
C1–C2–C5 | 125.0 (2) | 126.55 |
C3–C2–C5 | 127.3 (2) | 126.24 |
C4–C3–C2 | 106.0 (2) | 105.99 |
C3–C4–O4 | 110.7 (1) | 110.56 |
O3–C5–C2 | 123.2 (2) | 123.03 |
O1–B1–C1–C2 | 4.4 (3) | 0.00 |
O2–B1–C1–C2 | -175.3 (2) | -180.00 |
O1–B1–C1–O4 | -176.9 (2) | -180.00 |
O2–B1–C1–O4 | 3.4 (2) | 0.00 |
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