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In the crystal structure of the title compound, C6H8B2O4, centrosymmetric 1,4-phenyl­enediboronic acid mol­ecules are linked by characteristic hydrogen bonding of B(OH)2 groups. Primary association involves the formation of centrosymmetric cyclic dimers which leads to the formation of linear chains; these, in turn, associate by secondary hydrogen bonding, via unit-cell translations in the a axis direction, to form sheets.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804016150/lh6237sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804016150/lh6237Isup2.hkl
Contains datablock I

CCDC reference: 248778

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.050
  • wR factor = 0.135
  • Data-to-parameter ratio = 11.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 3.09
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: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: SHELXTL (Bruker, 2000).

1,4-phenylenediboronic acid top
Crystal data top
C6H8B2O4Z = 1
Mr = 165.74F(000) = 86
Triclinic, P1Dx = 1.479 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 4.989 (3) ÅCell parameters from 1056 reflections
b = 5.305 (3) Åθ = 4.0–27.3°
c = 7.368 (4) ŵ = 0.12 mm1
α = 104.429 (10)°T = 293 K
β = 97.886 (9)°Block, colorless
γ = 93.797 (10)°0.45 × 0.39 × 0.21 mm
V = 186.05 (19) Å3
Data collection top
Bruker SMART CCD
diffractometer
678 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.036
Graphite monochromatorθmax = 26.0°, θmin = 2.9°
φ and ω scansh = 66
1948 measured reflectionsk = 66
728 independent reflectionsl = 99
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H atoms treated by a mixture of independent and constrained refinement
S = 1.21 w = 1/[σ2(Fo2) + (0.0588P)2 + 0.0474P]
where P = (Fo2 + 2Fc2)/3
728 reflections(Δ/σ)max = 0.015
61 parametersΔρmax = 0.20 e Å3
2 restraintsΔρmin = 0.23 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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 2.8907 (0.0055) x + 3.4759 (0.0048) y + 3.1489 (0.0069) z = 1.7035 (0.0077)

* -0.0006 (0.0011) C1 * 0.0006 (0.0012) C2 * 0.0006 (0.0012) C3 * 0.0006 (0.0011) C1_$3 * -0.0006 (0.0012) C2_$3 * -0.0006 (0.0012) C3_$3

Rms deviation of fitted atoms = 0.0006

- 0.1036 (0.0006) x + 4.5317 (0.0111) y + 2.0448 (0.0276) z = 2.7972 (0.0142)

Angle to previous plane (with approximate e.s.d.) = 35.32 (0.23)

* -0.1493 (0.0011) B1 * 0.1645 (0.0010) O1 * -0.1707 (0.0011) O2 * -0.0457 (0.0008) B1_$2 * 0.2682 (0.0016) O1_$2 * -0.0671 (0.0006) O2_$2

Rms deviation of fitted atoms = 0.1618

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
B10.5089 (4)0.2811 (4)0.6978 (3)0.0326 (5)
O10.7500 (3)0.3719 (3)0.6621 (2)0.0469 (5)
H100.724 (6)0.462 (4)0.584 (3)0.070*
O20.2790 (3)0.3196 (3)0.59002 (18)0.0404 (5)
H200.133 (3)0.282 (5)0.627 (3)0.061*
C10.5028 (3)0.1325 (3)0.8561 (2)0.0314 (5)
C20.2858 (4)0.0455 (4)0.8539 (3)0.0372 (5)
H20.13900.07820.75570.045*
C30.7174 (4)0.1757 (4)1.0057 (3)0.0366 (5)
H30.86600.29451.01130.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
B10.0341 (11)0.0395 (11)0.0315 (10)0.0064 (8)0.0075 (8)0.0209 (8)
O10.0311 (8)0.0718 (10)0.0567 (9)0.0071 (6)0.0094 (6)0.0500 (8)
O20.0297 (7)0.0607 (9)0.0437 (8)0.0042 (6)0.0064 (6)0.0373 (7)
C10.0322 (10)0.0371 (10)0.0325 (10)0.0073 (7)0.0086 (7)0.0203 (7)
C20.0334 (9)0.0478 (11)0.0350 (10)0.0011 (8)0.0028 (7)0.0249 (8)
C30.0320 (9)0.0447 (11)0.0394 (10)0.0038 (7)0.0030 (8)0.0258 (8)
Geometric parameters (Å, º) top
B1—O11.349 (3)C1—C21.384 (3)
B1—O21.360 (2)C1—C31.390 (3)
B1—C11.564 (2)C2—C3i1.381 (3)
O1—H100.84 (2)C2—H20.9300
O2—H200.841 (17)C3—H30.9300
O1—B1—O2117.70 (15)C3—C1—B1120.74 (17)
O1—B1—C1119.67 (16)C3i—C2—C1121.44 (17)
O2—B1—C1122.62 (16)C3i—C2—H2119.3
B1—O1—H10110 (2)C1—C2—H2119.3
B1—O2—H20114.9 (17)C2i—C3—C1121.23 (17)
C2—C1—C3117.33 (15)C2i—C3—H3119.4
C2—C1—B1121.92 (16)C1—C3—H3119.4
O1—B1—C1—C2155.2 (2)C3—C1—C2—C3i0.2 (3)
O2—B1—C1—C223.5 (3)B1—C1—C2—C3i179.96 (16)
O1—B1—C1—C324.9 (3)C2—C1—C3—C2i0.2 (3)
O2—B1—C1—C3156.33 (19)B1—C1—C3—C2i179.96 (16)
Symmetry code: (i) x+1, y, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H10···O2ii0.84 (2)1.93 (2)2.761 (2)172 (3)
O2—H20···O1iii0.84 (2)2.04 (1)2.781 (2)148 (2)
Symmetry codes: (ii) x+1, y+1, z+1; (iii) x1, y, z.
 

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