Potassium [(1S)-1-azido-2-phenyl­eth­yl]trifluorido­borate

Lejon, T.; Gorovoy, A.S.; Khrustalev, V.N.

doi:10.1107/S1600536812030085

metal-organic compounds

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Volume 68| Part 8| August 2012| Page m1048

https://doi.org/10.1107/S1600536812030085

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Potassium [(1S)-1-azido-2-phenylethyl]trifluoridoborate

Tore Lejon,^a ^* Alexey S. Gorovoy ^a and Victor N. Khrustalev ^b

^aDepartment of Chemistry, Faculty of Science and Technology, University of Tromsø, N-9037 Tromsø, Norway, and ^bX-Ray Structural Centre, A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street, B-334, Moscow 119991, Russian Federation
^*Correspondence e-mail: tore.lejon@uit.no

(Received 27 June 2012; accepted 2 July 2012; online 10 July 2012)

The title compound, K⁺·C₈H₈BF₃N₃⁻, is a salt containing the chiral organic trifluoridoborate anion. The organic anions and potassium cations are tightly bound to each other by the coordination K—F [2.654 (3)–3.102 (3) Å] and K—N [2.951 (4)–3.338 (4) Å] interactions. Thus, the potassium cation adopts a nine-vertex coordination polyhedron, which can be described as a distorted monocapped tetragonal antiprism. In the crystal, the organic anions and potassium cations form layers parallel to (001). Weak C—H⋯π interactions between neighbouring phenyl rings further stabilize the crystal.

Related literature

For the Matteson homologation, see: Matteson & Kim (2002 ); Matteson et al. (2006 ). For related compounds, see: Matteson & Beedle (1987 ); Scriven & Turnbull (1988 ); Darses & Genet (2008 ); Huang et al. (2009 ).

Experimental

Crystal data

K⁺·C₈H₈BF₃N₃⁻
M_r = 253.08
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.052 (2) Å
b = 6.959 (2) Å
c = 25.120 (8) Å
V = 1057.9 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.52 mm⁻¹
T = 100 K
0.15 × 0.10 × 0.01 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.926, T_max = 0.995
10239 measured reflections
2075 independent reflections
1203 reflections with I > 2σ(I)
R_int = 0.060

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.081
S = 0.98
2075 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.40 e Å⁻³
Absolute structure: Flack (1983 ), 828 Friedel pairs
Flack parameter: 0.00 (8)

Table 1
Weak C—H⋯π interactions between neighbouring phenyl rings (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯C3ⁱ	0.95	2.93	3.528 (6)	122
C4—H4⋯C4ⁱ	0.95	2.98	3.823 (6)	149
C4—H4⋯C5ⁱ	0.95	3.08	3.974 (7)	158
C4—H4⋯C6ⁱ	0.95	3.13	3.841 (7)	133
C4—H4⋯C7ⁱ	0.95	3.09	3.556 (7)	112
C4—H4⋯C8ⁱ	0.95	2.98	3.382 (6)	107
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]$ .

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2001 ); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812030085/cv5318sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812030085/cv5318Isup2.hkl

checkCIF report

Comment top

The target compound was synthesized as part of our studies on the Matteson homologation and the synthesis of chiral amino boronates. It was accomplished using potassium or caesium bifluorides which have been shown to be useful reagents in the deprotection of boronic esters (Matteson & Kim, 2002; Matteson et al., 2006). However, organotrifluoridoborates are not only used for preservation and release of the boronic acid moiety, but also find application in different synthetic transformations (Darses & Genet, 2008). Moreover, organic azides have a rich chemistry and could prove important as building blocks in click chemistry (Scriven & Turnbull, 1988; Huang et al., 2009).

The title compound - potassium [(1S)-1-azido-2-phenyl-ethyl]-trifluoro-boranuide, C₈H₈BF₃KN₃ (I), is a salt containing the chiral organic trifluoridoborate anion (Figure 1). It crystallizes in the orthorhombic space group P2₁2₁2₁, with one crystallographically independent formula unit within the lattice cell. The asymmetrical C1 carbon atom has the S-configuration. The organic anions and potassium cations are tightly bound to each other by the coordination K—F [K1—F1 2.648 (3), K1—F1ⁱ 2.673 (3), K1—F2ⁱ 2.933 (3), K1—F2ⁱⁱ 2.685 (3), K1—F3ⁱⁱ 3.102 (3) and K1—F3ⁱⁱⁱ 2.654 (3) Å] and K—N [K1—N1 2.951 (4), K1—N3ⁱⁱⁱ 3.338 (4) and K1—N3^iv 3.020 (4) Å] interactions [symmetry codes: (i) -x, y + 1/2, -z + 3/2; (ii) x, y + 1, z; (iii) -x + 1, y + 1/2, -z + 3/2; (iv) x - 1, y + 1, z]. Thus, the potassium cation adopts the 9-vertex coordination polyhedron, which can be described as a distorted monocapped tetragonal antiprism (Figure 2).

In the crystal, the organic anions and potassium cations form the layers parallel to (001) (Figure 3). Moreover, the crystal packing is stabilized by the additional C4—H4···π interactions between the phenyl rings, with C4···Centroid^v distance of 3.418 (3) Å [symmetry code: (v) x - 1/2, -y + 1/2, -z + 2].

Related literature top

For the Matteson homologation, see: Matteson & Kim (2002); Matteson et al. (2006). For related compounds, see: Matteson & Beedle (1987); Scriven & Turnbull (1988); Darses & Genet (2008); Huang et al. (2009).

Experimental top

The initial 2-[(1S)-1-azido-2-phenyl-ethyl]-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborole was obtained according to the procedure described earlier (Matteson & Beedle, 1987). A saturated water solution of potassium bifluoride (2.4 g, 30 mmol) was added drop wise to a solution of 2-[(1S)-1-azido-2-phenyl-ethyl]-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborole (1.0 g, 3 mmol) in methanol (25 ml) at room temperature (Figure 4). The reaction mixture was stirred for 24 h. Then, the solvents were evaporated under reduced pressure (Attention! Hydrogen fluoride). The residue was washed with pentane and re-crystallized from hot methanol to give I as colourless crystals. Yield is 0.6 g (77%). ¹H NMR (400 MHz, D₂O, 293 K): δ = 7.57–7.12 (m, 5H), 2.94 (dd, J = 14.2, 3.3 Hz, 1H), 2.84 (m, 1H), 2.71 (m, 1H). ¹³C NMR (101 MHz, D₂O, 293 K): δ = 141.68, 128.84, 128.51, 126.10, 35.55. ¹⁹F NMR (376 MHz, D₂O, 293 K): δ = -145.40 (s).

Structure description top

For the Matteson homologation, see: Matteson & Kim (2002); Matteson et al. (2006). For related compounds, see: Matteson & Beedle (1987); Scriven & Turnbull (1988); Darses & Genet (2008); Huang et al. (2009).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Independent part of the crystal structure of I. Displacement ellipsoids are shown at the 50% probability level.
	Fig. 2. The coordination environment of potassium cation [symmetry codes: (i) -x, y + 1/2, -z + 3/2; (ii) x, y + 1, z; (iii) -x + 1, y + 1/2, -z + 3/2; (iv) x - 1, y + 1, z].
	Fig. 3. The layers in I parallel to (001).
	Fig. 4. Reaction of 2-[(1S)-1-azido-2-phenyl-ethyl]-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborole with potassium bifluoride.

Potassium [(1S)-1-azido-2-phenylethyl]trifluoridoborate top

Crystal data top

K⁺·C₈H₈BF₃N₃⁻	F(000) = 512
M_r = 253.08	D_x = 1.589 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 546 reflections
a = 6.052 (2) Å	θ = 3.2–18.5°
b = 6.959 (2) Å	µ = 0.52 mm⁻¹
c = 25.120 (8) Å	T = 100 K
V = 1057.9 (6) Å³	Plate, colourless
Z = 4	0.15 × 0.10 × 0.01 mm

Data collection top

Bruker APEXII CCD diffractometer	2075 independent reflections
Radiation source: fine-focus sealed tube	1203 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.060
φ and ω scans	θ_max = 26.0°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −7→7
T_min = 0.926, T_max = 0.995	k = −8→8
10239 measured reflections	l = −30→30

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.050	H-atom parameters constrained
wR(F²) = 0.081	w = 1/[σ²(F_o²) + (0.0191P)²] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max < 0.001
2075 reflections	Δρ_max = 0.33 e Å⁻³
145 parameters	Δρ_min = −0.40 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 828 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (8)

Crystal data top

K⁺·C₈H₈BF₃N₃⁻	V = 1057.9 (6) Å³
M_r = 253.08	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.052 (2) Å	µ = 0.52 mm⁻¹
b = 6.959 (2) Å	T = 100 K
c = 25.120 (8) Å	0.15 × 0.10 × 0.01 mm

Data collection top

Bruker APEXII CCD diffractometer	2075 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	1203 reflections with I > 2σ(I)
T_min = 0.926, T_max = 0.995	R_int = 0.060
10239 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	H-atom parameters constrained
wR(F²) = 0.081	Δρ_max = 0.33 e Å⁻³
S = 0.98	Δρ_min = −0.40 e Å⁻³
2075 reflections	Absolute structure: Flack (1983), 828 Friedel pairs
145 parameters	Absolute structure parameter: 0.00 (8)
0 restraints

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	U_iso*/U_eq
K1	0.19352 (19)	0.92096 (16)	0.77175 (5)	0.0230 (3)
N1	0.4374 (7)	0.6992 (6)	0.85281 (14)	0.0243 (11)
N2	0.6381 (7)	0.7035 (6)	0.84172 (15)	0.0224 (11)
N3	0.8199 (7)	0.7267 (7)	0.83058 (14)	0.0296 (11)
C1	0.3397 (8)	0.5009 (6)	0.86075 (17)	0.0187 (12)
H1	0.1992	0.5194	0.8811	0.022*
C2	0.4850 (8)	0.3714 (6)	0.89471 (16)	0.0206 (13)
H2A	0.4156	0.2427	0.8965	0.025*
H2B	0.6294	0.3564	0.8766	0.025*
C3	0.5268 (8)	0.4407 (6)	0.95126 (18)	0.0167 (11)
C4	0.3648 (8)	0.4141 (7)	0.99013 (17)	0.0215 (12)
H4	0.2286	0.3546	0.9811	0.026*
C5	0.4030 (8)	0.4748 (7)	1.04210 (19)	0.0227 (13)
H5	0.2922	0.4575	1.0684	0.027*
C6	0.6016 (8)	0.5603 (7)	1.05561 (19)	0.0231 (12)
H6	0.6273	0.5998	1.0913	0.028*
C7	0.7647 (8)	0.5888 (7)	1.01697 (18)	0.0236 (12)
H7	0.9006	0.6489	1.0260	0.028*
C8	0.7250 (8)	0.5283 (6)	0.96550 (18)	0.0219 (13)
H8	0.8356	0.5469	0.9392	0.026*
F1	0.1942 (4)	0.5408 (3)	0.76697 (10)	0.0241 (7)
F2	0.0979 (4)	0.2693 (4)	0.81157 (9)	0.0250 (7)
F3	0.4491 (4)	0.3061 (4)	0.78057 (9)	0.0270 (7)
B1	0.2716 (9)	0.4042 (8)	0.8047 (2)	0.0171 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
K1	0.0246 (6)	0.0215 (6)	0.0227 (6)	0.0008 (6)	−0.0020 (6)	0.0005 (6)
N1	0.021 (3)	0.028 (3)	0.024 (3)	−0.002 (2)	0.002 (2)	0.000 (2)
N2	0.031 (3)	0.017 (3)	0.019 (2)	−0.002 (2)	0.000 (2)	0.001 (2)
N3	0.025 (3)	0.036 (3)	0.029 (2)	−0.002 (3)	0.006 (2)	0.003 (2)
C1	0.017 (3)	0.017 (3)	0.022 (3)	−0.004 (2)	−0.001 (2)	0.004 (2)
C2	0.021 (3)	0.023 (3)	0.017 (3)	0.000 (2)	−0.001 (2)	0.003 (2)
C3	0.023 (3)	0.006 (3)	0.021 (3)	0.001 (2)	−0.005 (2)	0.002 (2)
C4	0.025 (3)	0.017 (3)	0.023 (3)	−0.006 (3)	−0.001 (2)	0.000 (3)
C5	0.025 (3)	0.025 (3)	0.019 (3)	0.001 (3)	0.001 (3)	−0.002 (2)
C6	0.030 (3)	0.017 (3)	0.022 (3)	−0.001 (3)	−0.004 (3)	0.001 (3)
C7	0.020 (3)	0.019 (3)	0.031 (3)	0.001 (3)	−0.007 (2)	0.000 (3)
C8	0.021 (3)	0.018 (3)	0.027 (3)	0.003 (2)	0.000 (3)	0.000 (2)
F1	0.0326 (17)	0.0189 (15)	0.0209 (16)	−0.0006 (15)	−0.0068 (16)	0.0024 (13)
F2	0.0288 (16)	0.0240 (17)	0.0221 (15)	−0.0069 (15)	−0.0006 (12)	0.0005 (15)
F3	0.0234 (16)	0.0341 (18)	0.0234 (16)	0.0050 (14)	0.0006 (13)	−0.0092 (15)
B1	0.017 (3)	0.013 (3)	0.021 (3)	0.000 (3)	0.000 (2)	−0.001 (3)

Geometric parameters (Å, º) top

K1—F1	2.648 (3)	C2—H2A	0.9900
K1—F3ⁱ	2.654 (3)	C2—H2B	0.9900
K1—F1ⁱⁱ	2.673 (3)	C3—C8	1.392 (6)
K1—F2ⁱⁱⁱ	2.685 (3)	C3—C4	1.396 (6)
K1—F2ⁱⁱ	2.933 (3)	C4—C5	1.391 (6)
K1—N1	2.951 (4)	C4—H4	0.9500
K1—N3^iv	3.020 (4)	C5—C6	1.383 (6)
K1—F3ⁱⁱⁱ	3.102 (3)	C5—H5	0.9500
K1—N3ⁱ	3.338 (4)	C6—C7	1.399 (6)
N1—N2	1.246 (5)	C6—H6	0.9500
N1—C1	1.515 (6)	C7—C8	1.381 (6)
N2—N3	1.147 (5)	C7—H7	0.9500
C1—C2	1.521 (6)	C8—H8	0.9500
C1—B1	1.614 (7)	F1—B1	1.422 (6)
C1—H1	1.0000	F2—B1	1.420 (6)
C2—C3	1.521 (6)	F3—B1	1.410 (6)

F1—K1—F3ⁱ	71.05 (9)	N1—C1—B1	111.4 (4)
F1—K1—F1ⁱⁱ	107.25 (7)	C2—C1—B1	112.9 (4)
F3ⁱ—K1—F1ⁱⁱ	128.98 (8)	N1—C1—H1	106.4
F1—K1—F2ⁱⁱⁱ	156.77 (10)	C2—C1—H1	106.4
F3ⁱ—K1—F2ⁱⁱⁱ	129.20 (9)	B1—C1—H1	106.4
F1ⁱⁱ—K1—F2ⁱⁱⁱ	70.42 (8)	C3—C2—C1	115.6 (4)
F1—K1—F2ⁱⁱ	66.99 (8)	C3—C2—H2A	108.4
F3ⁱ—K1—F2ⁱⁱ	91.61 (8)	C1—C2—H2A	108.4
F1ⁱⁱ—K1—F2ⁱⁱ	47.55 (7)	C3—C2—H2B	108.4
F2ⁱⁱⁱ—K1—F2ⁱⁱ	117.46 (7)	C1—C2—H2B	108.4
F1—K1—N1	60.53 (10)	H2A—C2—H2B	107.4
F3ⁱ—K1—N1	77.08 (10)	C8—C3—C4	118.9 (4)
F1ⁱⁱ—K1—N1	148.57 (10)	C8—C3—C2	121.4 (4)
F2ⁱⁱⁱ—K1—N1	108.83 (10)	C4—C3—C2	119.7 (4)
F2ⁱⁱ—K1—N1	127.22 (11)	C5—C4—C3	120.0 (4)
F1—K1—N3^iv	64.93 (11)	C5—C4—H4	120.0
F3ⁱ—K1—N3^iv	135.84 (11)	C3—C4—H4	120.0
F1ⁱⁱ—K1—N3^iv	70.16 (10)	C6—C5—C4	120.3 (5)
F2ⁱⁱⁱ—K1—N3^iv	93.46 (11)	C6—C5—H5	119.8
F2ⁱⁱ—K1—N3^iv	74.82 (10)	C4—C5—H5	119.8
N1—K1—N3^iv	78.62 (11)	C5—C6—C7	120.3 (4)
F1—K1—F3ⁱⁱⁱ	149.93 (9)	C5—C6—H6	119.9
F3ⁱ—K1—F3ⁱⁱⁱ	83.65 (6)	C7—C6—H6	119.9
F1ⁱⁱ—K1—F3ⁱⁱⁱ	101.20 (8)	C8—C7—C6	118.9 (4)
F2ⁱⁱⁱ—K1—F3ⁱⁱⁱ	45.66 (7)	C8—C7—H7	120.5
F2ⁱⁱ—K1—F3ⁱⁱⁱ	131.42 (8)	C6—C7—H7	120.5
N1—K1—F3ⁱⁱⁱ	98.81 (10)	C7—C8—C3	121.6 (5)
N3^iv—K1—F3ⁱⁱⁱ	136.46 (10)	C7—C8—H8	119.2
F1—K1—N3ⁱ	127.01 (11)	C3—C8—H8	119.2
F3ⁱ—K1—N3ⁱ	80.25 (10)	B1—F1—K1	129.7 (3)
F1ⁱⁱ—K1—N3ⁱ	59.97 (9)	B1—F1—K1^vii	108.9 (3)
F2ⁱⁱⁱ—K1—N3ⁱ	72.92 (9)	K1—F1—K1^vii	109.06 (9)
F2ⁱⁱ—K1—N3ⁱ	70.44 (10)	B1—F2—K1^viii	113.1 (3)
N1—K1—N3ⁱ	151.29 (11)	B1—F2—K1^vii	96.9 (3)
N3^iv—K1—N3ⁱ	130.08 (7)	K1^viii—F2—K1^vii	100.87 (8)
F3ⁱⁱⁱ—K1—N3ⁱ	61.08 (9)	B1—F3—K1^vi	133.5 (3)
N2—N1—C1	115.6 (4)	B1—F3—K1^viii	94.0 (3)
N2—N1—K1	108.7 (3)	K1^vi—F3—K1^viii	129.14 (10)
C1—N1—K1	111.8 (3)	F3—B1—F2	107.2 (4)
N3—N2—N1	173.1 (5)	F3—B1—F1	106.7 (4)
N2—N3—K1^v	154.2 (4)	F2—B1—F1	106.2 (4)
N2—N3—K1^vi	94.3 (3)	F3—B1—C1	112.5 (4)
K1^v—N3—K1^vi	85.80 (9)	F2—B1—C1	111.0 (4)
N1—C1—C2	112.8 (4)	F1—B1—C1	112.7 (4)

F1—K1—N1—N2	101.9 (3)	N1—K1—F1—B1	9.8 (4)
F3ⁱ—K1—N1—N2	26.6 (3)	N3^iv—K1—F1—B1	−81.1 (4)
F1ⁱⁱ—K1—N1—N2	176.1 (3)	F3ⁱⁱⁱ—K1—F1—B1	61.1 (4)
F2ⁱⁱⁱ—K1—N1—N2	−100.8 (3)	N3ⁱ—K1—F1—B1	156.4 (3)
F2ⁱⁱ—K1—N1—N2	108.6 (3)	F3ⁱ—K1—F1—K1^vii	−127.74 (10)
N3^iv—K1—N1—N2	169.4 (3)	F1ⁱⁱ—K1—F1—K1^vii	−1.60 (5)
F3ⁱⁱⁱ—K1—N1—N2	−54.8 (3)	F2ⁱⁱⁱ—K1—F1—K1^vii	78.8 (3)
N3ⁱ—K1—N1—N2	−12.2 (5)	F2ⁱⁱ—K1—F1—K1^vii	−27.48 (8)
F1—K1—N1—C1	−26.9 (3)	N1—K1—F1—K1^vii	146.70 (13)
F3ⁱ—K1—N1—C1	−102.3 (3)	N3^iv—K1—F1—K1^vii	55.89 (11)
F1ⁱⁱ—K1—N1—C1	47.3 (4)	F3ⁱⁱⁱ—K1—F1—K1^vii	−161.99 (14)
F2ⁱⁱⁱ—K1—N1—C1	130.4 (3)	N3ⁱ—K1—F1—K1^vii	−66.63 (15)
F2ⁱⁱ—K1—N1—C1	−20.2 (3)	K1^vi—F3—B1—F2	161.9 (2)
N3^iv—K1—N1—C1	40.6 (3)	K1^viii—F3—B1—F2	2.3 (4)
F3ⁱⁱⁱ—K1—N1—C1	176.4 (3)	K1^vi—F3—B1—F1	48.4 (5)
N3ⁱ—K1—N1—C1	−141.0 (3)	K1^viii—F3—B1—F1	−111.2 (3)
N2—N1—C1—C2	44.7 (5)	K1^vi—F3—B1—C1	−75.8 (5)
K1—N1—C1—C2	169.7 (3)	K1^viii—F3—B1—C1	124.6 (4)
N2—N1—C1—B1	−83.6 (5)	K1^viii—F2—B1—F3	−2.8 (4)
K1—N1—C1—B1	41.5 (4)	K1^vii—F2—B1—F3	−107.8 (3)
N1—C1—C2—C3	61.4 (5)	K1^viii—F2—B1—F1	111.0 (3)
B1—C1—C2—C3	−171.2 (4)	K1^vii—F2—B1—F1	6.1 (4)
C1—C2—C3—C8	−101.8 (5)	K1^viii—F2—B1—C1	−126.1 (3)
C1—C2—C3—C4	79.0 (5)	K1^vii—F2—B1—C1	128.9 (3)
C8—C3—C4—C5	0.0 (7)	K1—F1—B1—F3	−115.8 (3)
C2—C3—C4—C5	179.2 (4)	K1^vii—F1—B1—F3	107.2 (3)
C3—C4—C5—C6	−0.5 (7)	K1—F1—B1—F2	130.0 (3)
C4—C5—C6—C7	0.9 (7)	K1^vii—F1—B1—F2	−7.0 (4)
C5—C6—C7—C8	−0.8 (7)	K1—F1—B1—C1	8.2 (6)
C6—C7—C8—C3	0.3 (7)	K1^vii—F1—B1—C1	−128.8 (3)
C4—C3—C8—C7	0.1 (7)	N1—C1—B1—F3	86.5 (5)
C2—C3—C8—C7	−179.0 (4)	C2—C1—B1—F3	−41.7 (6)
F3ⁱ—K1—F1—B1	95.3 (4)	N1—C1—B1—F2	−153.3 (4)
F1ⁱⁱ—K1—F1—B1	−138.5 (4)	C2—C1—B1—F2	78.5 (5)
F2ⁱⁱⁱ—K1—F1—B1	−58.1 (5)	N1—C1—B1—F1	−34.3 (6)
F2ⁱⁱ—K1—F1—B1	−164.4 (4)	C2—C1—B1—F1	−162.5 (4)

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x, y+1/2, −z+3/2; (iii) x, y+1, z; (iv) x−1, y, z; (v) x+1, y, z; (vi) −x+1, y−1/2, −z+3/2; (vii) −x, y−1/2, −z+3/2; (viii) x, y−1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···C3^ix	0.95	2.93	3.528 (6)	122
C4—H4···C4^ix	0.95	2.98	3.823 (6)	149
C4—H4···C5^ix	0.95	3.08	3.974 (7)	158
C4—H4···C6^ix	0.95	3.13	3.841 (7)	133
C4—H4···C7^ix	0.95	3.09	3.556 (7)	112
C4—H4···C8^ix	0.95	2.98	3.382 (6)	107

Symmetry code: (ix) x−1/2, −y+1/2, −z+2.

Experimental details

Crystal data
Chemical formula	K⁺·C₈H₈BF₃N₃⁻
M_r	253.08
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	6.052 (2), 6.959 (2), 25.120 (8)
V (Å³)	1057.9 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.52
Crystal size (mm)	0.15 × 0.10 × 0.01

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.926, 0.995
No. of measured, independent and observed [I > 2σ(I)] reflections	10239, 2075, 1203
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.081, 0.98
No. of reflections	2075
No. of parameters	145
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.40
Absolute structure	Flack (1983), 828 Friedel pairs
Absolute structure parameter	0.00 (8)

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···C3ⁱ	0.95	2.93	3.528 (6)	122
C4—H4···C4ⁱ	0.95	2.98	3.823 (6)	149
C4—H4···C5ⁱ	0.95	3.08	3.974 (7)	158
C4—H4···C6ⁱ	0.95	3.13	3.841 (7)	133
C4—H4···C7ⁱ	0.95	3.09	3.556 (7)	112
C4—H4···C8ⁱ	0.95	2.98	3.382 (6)	107

Symmetry code: (i) x−1/2, −y+1/2, −z+2.

Acknowledgements

Support from the Norwegian Science Council and the FORNY program is gratefully acknowledged.

References

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