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ISSN: 2056-9890

Potassium tri­fluoro­[(Z)-3-meth­oxy­prop-1-en­yl]borate

aDepartment of Chemistry, Universidade Federal de São Carlos, 13565-905 São Carlos, SP, Brazil, bDepartamento de Farmácia, Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, São Paulo, SP, Brazil, and cInstituto de Química, Universidade Federal do Rio de Janeiro, RJ, Brazil
*Correspondence e-mail: julio@power.ufscar.br

(Received 30 October 2008; accepted 6 November 2008; online 13 November 2008)

In the title salt, K+·C4H7BF3O, the K atom is surrounded by six anions making close contacts through seven F [K⋯F = 2.779 (1)–3.048 (1) Å] and two O [K⋯O = 2.953 (2) and 3.127 (2) Å] atoms in a trivacant fac-vIC-9 icosa­hedral coordination geometry.

Related literature

For related structures, see: Caracelli et al. (2007[Caracelli, I., Stefani, H. A., Vieira, A. S., Machado, M. M. P. & Zukerman-Schpector, J. (2007). Z. Kristallogr. New Cryst. Struct. 222, 345-346.]); Stefani et al. (2006[Stefani, H. A., Cella, R., Zukerman-Schpector, J. & Caracelli, I. (2006). Z. Kristallogr. New Cryst. Struct. 221, 167-168.]); For related literature, see: Ruiz-Martínez et al. (2008[Ruiz-Martínez, A., Casanova, D. & Alvarez, S. (2008). Dalton Trans. pp. 2583-2591.]); Vieira et al. (2008[Vieira, A. S., Fiorante, P. F., Zukerman-Schpector, J., Alves, D., Botteselle, G. V. & Stefani, H. A. (2008). Tetrahedron, 64, 7234-7241.]).

[Scheme 1]

Experimental

Crystal data
  • K+·C4H7BF3O

  • Mr = 178.01

  • Monoclinic, P 21 /c

  • a = 10.882 (2) Å

  • b = 7.2668 (15) Å

  • c = 9.2317 (18) Å

  • β = 101.52 (3)°

  • V = 715.3 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.72 mm−1

  • T = 291 (2) K

  • 0.31 × 0.22 × 0.11 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2006[Bruker (2006). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.804, Tmax = 0.924

  • 16605 measured reflections

  • 1327 independent reflections

  • 1182 reflections with I > 2σ(I)

  • Rint = 0.059

Refinement
  • R[F2 > 2σ(F2)] = 0.027

  • wR(F2) = 0.072

  • S = 1.00

  • 1327 reflections

  • 92 parameters

  • H-atom parameters constrained

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.20 e Å−3

Data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: PHICHI (Duisenberg et al., 2000[Duisenberg, A. J. M., Hooft, R. W. W., Schreurs, A. M. M. & Kroon, J. (2000). J. Appl. Cryst. 33, 893-898.]); data reduction: EVAL-14 (CCD) (Duisenberg et al., 2003[Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229.]); program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


Comment top

Organic compounds of tellurium, such as Z-vinylic tellurides, are important synthetic precursors of organometallic molecules and organic salts and can be useful in the synthesis of new potassium vinyl trifluoroborate salts. Organotrifluoroborates represent an alternative to boronic acids, boronate esters, and organoboranes for use in the Suzuki-Miyaura reaction and other transition-metal-catalyzed cross-coupling reactions (Vieira et al. 2008). Following the ideas of Ruiz-Martínez et al. (2008) the geometry around the K+ ion can be described as a trivacant icosahedron, fac-vIC-9, a non spherical shape, as shown in Figure 2. The independent molecules in (I) are connected via C3···F2i = 3.214 (2) Å, C3—H3B···F2i = 137° (i = x - 1/2, -y + 3/2, z).

Related literature top

For related structures, see: Caracelli et al. (2007); Stefani et al.(2006); For related literature, see: Ruiz-Martínez et al. (2008); Vieira et al. (2008).

Experimental top

nBuLi (0.8 mmol) was added dropwise at 203 K to a solution of the appropriated Z-vinylic telluride (1 mmol) in Et2O (6 ml). The bath temperature was raised to 253 K. After 20 minutes B(OiPr)3 (1.0 mmol) was added at 233 K. After 1 h, a aqueous solution of KHF2 (4 mmol in 10 ml of water) was added to the reaction mixture. Then, the solvent and water were eliminated by evaporation. To the obtained solid hot acetone was added and the bulk reactional was filtered and dried, yielding 67% of (Z)-potassium vinyltrifluoroborate salt. Single crystals were obtained by slow evaporation from Et2O.

Refinement top

The H atoms were refined in the riding-model approximation, with C—H = 0.93–0.97Å and Uiso(H) = 1.5Ueq(methyl C) or 1.2Ueq(remaining C).

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: PHICHI (Duisenberg et al., 2000); data reduction: EVAL14 (CCD) (Duisenberg et al., 2003); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound showing atom labelling scheme and displacement ellipsoids at the 50% probability level (arbitrary spheres for the H atoms).
[Figure 2] Fig. 2. The trivacant icosahedron, fac-vIC-9, around the K+ ion. Symmetry operations: i = 1 - x, y - 1/2, 1/2 - z; ii = 1 - x, y - 1, -z; iii = 1 - x, y + 1/2, 1/2 - z; iv = 1 - x, -2 - y, -z; v = x, -3/2 - y, z - 1/2; vi = x, -3/2 - y, 1/2 + z.
Potassium trifluoro[(Z)-3-methoxyprop-1-enyl]borate top
Crystal data top
K+·C4H7BF3OF(000) = 360
Mr = 178.01Dx = 1.653 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9536 reflections
a = 10.882 (2) Åθ = 2.3–21.8°
b = 7.2668 (15) ŵ = 0.72 mm1
c = 9.2317 (18) ÅT = 291 K
β = 101.52 (3)°Block, colourless
V = 715.3 (3) Å30.31 × 0.22 × 0.11 mm
Z = 4
Data collection top
Enraf–Nonius KappaCCD
diffractometer
1327 independent reflections
Radiation source: fine-focus sealed tube1182 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.059
ϕ and ω scansθmax = 25.5°, θmin = 4.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2006)
h = 1313
Tmin = 0.804, Tmax = 0.924k = 88
16605 measured reflectionsl = 1111
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)] = 0.027Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0364P)2 + 0.2723P]
where P = (Fo2 + 2Fc2)/3
1327 reflections(Δ/σ)max < 0.001
92 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.21 e Å3
Crystal data top
K+·C4H7BF3OV = 715.3 (3) Å3
Mr = 178.01Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.882 (2) ŵ = 0.72 mm1
b = 7.2668 (15) ÅT = 291 K
c = 9.2317 (18) Å0.31 × 0.22 × 0.11 mm
β = 101.52 (3)°
Data collection top
Enraf–Nonius KappaCCD
diffractometer
1327 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2006)
1182 reflections with I > 2σ(I)
Tmin = 0.804, Tmax = 0.924Rint = 0.059
16605 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0270 restraints
wR(F2) = 0.072H-atom parameters constrained
S = 1.00Δρmax = 0.25 e Å3
1327 reflectionsΔρmin = 0.21 e Å3
92 parameters
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
B0.64509 (18)0.7960 (2)0.0837 (2)0.0305 (4)
C10.77652 (16)0.7044 (2)0.16327 (19)0.0371 (4)
H10.81430.75690.2530.045*
C20.83849 (15)0.5637 (2)0.11809 (19)0.0352 (4)
H20.91230.52540.17980.042*
C30.79730 (17)0.4641 (2)0.02438 (18)0.0379 (4)
H3A0.8630.47220.08140.045*
H3B0.72330.52420.08060.045*
C40.8776 (2)0.1624 (3)0.0361 (3)0.0588 (6)
H4A0.85390.03490.03040.088*
H4B0.93370.18570.02990.088*
H4C0.91860.19160.13540.088*
F10.63816 (10)0.84405 (14)0.06632 (11)0.0438 (3)
F20.61847 (9)0.95573 (12)0.16043 (10)0.0396 (3)
F30.54238 (9)0.67152 (13)0.08481 (11)0.0384 (3)
K0.40701 (3)0.83116 (5)0.27917 (4)0.03619 (15)
O0.76899 (12)0.27319 (17)0.00483 (16)0.0469 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
B0.0374 (9)0.0264 (9)0.0288 (9)0.0009 (7)0.0095 (7)0.0035 (7)
C10.0362 (9)0.0389 (9)0.0344 (8)0.0009 (7)0.0030 (7)0.0085 (7)
C20.0304 (8)0.0362 (9)0.0376 (9)0.0027 (7)0.0034 (7)0.0001 (7)
C30.0488 (10)0.0295 (9)0.0353 (9)0.0089 (7)0.0080 (7)0.0018 (7)
C40.0504 (12)0.0335 (10)0.0867 (17)0.0095 (9)0.0005 (11)0.0073 (10)
F10.0508 (6)0.0504 (6)0.0312 (5)0.0058 (5)0.0104 (4)0.0054 (4)
F20.0477 (6)0.0291 (5)0.0412 (6)0.0057 (4)0.0064 (4)0.0077 (4)
F30.0359 (5)0.0332 (5)0.0454 (6)0.0032 (4)0.0059 (4)0.0007 (4)
K0.0380 (2)0.0316 (2)0.0396 (2)0.00022 (14)0.00919 (16)0.00628 (15)
O0.0390 (7)0.0293 (6)0.0682 (9)0.0014 (5)0.0007 (6)0.0024 (6)
Geometric parameters (Å, º) top
B—F11.415 (2)C2—H20.9300
B—F21.4198 (19)C3—O1.440 (2)
B—F31.440 (2)C3—H3A0.9700
B—C11.615 (3)C3—H3B0.9700
B—K3.450 (2)C4—O1.417 (2)
C1—C21.337 (2)C4—H4A0.9600
C1—H10.9300C4—H4B0.9600
C2—C31.490 (2)C4—H4C0.9600
F1—B—F2108.08 (13)O—C3—H3A109.0
F1—B—F3105.82 (13)C2—C3—H3A109.0
F2—B—F3105.89 (13)O—C3—H3B109.0
F1—B—C1114.59 (15)C2—C3—H3B109.0
F2—B—C1111.11 (13)H3A—C3—H3B107.8
F3—B—C1110.86 (13)O—C4—H4A109.5
C2—C1—B129.00 (15)O—C4—H4B109.5
C2—C1—H1115.5H4A—C4—H4B109.5
B—C1—H1115.5O—C4—H4C109.5
C1—C2—C3124.44 (15)H4A—C4—H4C109.5
C1—C2—H2117.8H4B—C4—H4C109.5
C3—C2—H2117.8C4—O—C3113.13 (14)
O—C3—C2113.05 (14)
F1—B—C1—C250.8 (3)B—C1—C2—C32.2 (3)
F2—B—C1—C2173.64 (17)C1—C2—C3—O116.83 (19)
F3—B—C1—C268.9 (2)C2—C3—O—C476.3 (2)

Experimental details

Crystal data
Chemical formulaK+·C4H7BF3O
Mr178.01
Crystal system, space groupMonoclinic, P21/c
Temperature (K)291
a, b, c (Å)10.882 (2), 7.2668 (15), 9.2317 (18)
β (°) 101.52 (3)
V3)715.3 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.72
Crystal size (mm)0.31 × 0.22 × 0.11
Data collection
DiffractometerEnraf–Nonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2006)
Tmin, Tmax0.804, 0.924
No. of measured, independent and
observed [I > 2σ(I)] reflections
16605, 1327, 1182
Rint0.059
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.027, 0.072, 1.00
No. of reflections1327
No. of parameters92
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.25, 0.21

Computer programs: COLLECT (Nonius, 1998), PHICHI (Duisenberg et al., 2000), EVAL14 (CCD) (Duisenberg et al., 2003), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

 

Acknowledgements

We thank FAPESP (07/59404–2 to HAS and 08/02531–5 to JZS), CNPq (300613/2007 to HAS and 307121/2006–0 to JZS) and CAPES for financial support.

References

First citationAltomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationBruker (2006). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationCaracelli, I., Stefani, H. A., Vieira, A. S., Machado, M. M. P. & Zukerman-Schpector, J. (2007). Z. Kristallogr. New Cryst. Struct. 222, 345–346.  CAS Google Scholar
First citationDuisenberg, A. J. M., Hooft, R. W. W., Schreurs, A. M. M. & Kroon, J. (2000). J. Appl. Cryst. 33, 893–898.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationDuisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220–229.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
First citationNonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.  Google Scholar
First citationRuiz-Martínez, A., Casanova, D. & Alvarez, S. (2008). Dalton Trans. pp. 2583–2591.  Web of Science CrossRef Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationStefani, H. A., Cella, R., Zukerman-Schpector, J. & Caracelli, I. (2006). Z. Kristallogr. New Cryst. Struct. 221, 167–168.  CAS Google Scholar
First citationVieira, A. S., Fiorante, P. F., Zukerman-Schpector, J., Alves, D., Botteselle, G. V. & Stefani, H. A. (2008). Tetrahedron, 64, 7234–7241.  Web of Science CSD CrossRef CAS Google Scholar

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ISSN: 2056-9890
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