Potassium [(1S)-1-azido-2-phenyl-eth-yl]trifluorido-borate.

The title compound, K(+)·C(8)H(8)BF(3)N(3) (-), is a salt containing the chiral organic trifluorido-borate 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] inter-actions. Thus, the potassium cation adopts a nine-vertex coordination polyhedron, which can be described as a distorted monocapped tetra-gonal anti-prism. In the crystal, the organic anions and potassium cations form layers parallel to (001). Weak C-H⋯π inter-actions 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 = 253.08

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.081

S = 0.98

2075 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.40 e Å−3

Absolute structure: Flack (1983 ▶), 828 Friedel pairs

Flack parameter: 0.00 (8)

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812030085/cv5318sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812030085/cv5318Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

K+·C8H8BF3N3−	F(000) = 512
Mr = 253.08	Dx = 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

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

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(Fo2) + (0.0191P)2] where P = (Fo2 + 2Fc2)/3
S = 0.98	(Δ/σ)max < 0.001
2075 reflections	Δρmax = 0.33 e Å−3
145 parameters	Δρmin = −0.40 e Å−3
0 restraints	Absolute structure: Flack (1983), 828 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.00 (8)

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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—N3iv	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—N3iv	64.93 (11)	C5—C4—H4	120.0
F3i—K1—N3iv	135.84 (11)	C3—C4—H4	120.0
F1ii—K1—N3iv	70.16 (10)	C6—C5—C4	120.3 (5)
F2iii—K1—N3iv	93.46 (11)	C6—C5—H5	119.8
F2ii—K1—N3iv	74.82 (10)	C4—C5—H5	119.8
N1—K1—N3iv	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)
N3iv—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—K1vii	108.9 (3)
F2iii—K1—N3i	72.92 (9)	K1—F1—K1vii	109.06 (9)
F2ii—K1—N3i	70.44 (10)	B1—F2—K1viii	113.1 (3)
N1—K1—N3i	151.29 (11)	B1—F2—K1vii	96.9 (3)
N3iv—K1—N3i	130.08 (7)	K1viii—F2—K1vii	100.87 (8)
F3iii—K1—N3i	61.08 (9)	B1—F3—K1vi	133.5 (3)
N2—N1—C1	115.6 (4)	B1—F3—K1viii	94.0 (3)
N2—N1—K1	108.7 (3)	K1vi—F3—K1viii	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—K1v	154.2 (4)	F2—B1—F1	106.2 (4)
N2—N3—K1vi	94.3 (3)	F3—B1—C1	112.5 (4)
K1v—N3—K1vi	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)	N3iv—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—K1vii	−127.74 (10)
N3iv—K1—N1—N2	169.4 (3)	F1ii—K1—F1—K1vii	−1.60 (5)
F3iii—K1—N1—N2	−54.8 (3)	F2iii—K1—F1—K1vii	78.8 (3)
N3i—K1—N1—N2	−12.2 (5)	F2ii—K1—F1—K1vii	−27.48 (8)
F1—K1—N1—C1	−26.9 (3)	N1—K1—F1—K1vii	146.70 (13)
F3i—K1—N1—C1	−102.3 (3)	N3iv—K1—F1—K1vii	55.89 (11)
F1ii—K1—N1—C1	47.3 (4)	F3iii—K1—F1—K1vii	−161.99 (14)
F2iii—K1—N1—C1	130.4 (3)	N3i—K1—F1—K1vii	−66.63 (15)
F2ii—K1—N1—C1	−20.2 (3)	K1vi—F3—B1—F2	161.9 (2)
N3iv—K1—N1—C1	40.6 (3)	K1viii—F3—B1—F2	2.3 (4)
F3iii—K1—N1—C1	176.4 (3)	K1vi—F3—B1—F1	48.4 (5)
N3i—K1—N1—C1	−141.0 (3)	K1viii—F3—B1—F1	−111.2 (3)
N2—N1—C1—C2	44.7 (5)	K1vi—F3—B1—C1	−75.8 (5)
K1—N1—C1—C2	169.7 (3)	K1viii—F3—B1—C1	124.6 (4)
N2—N1—C1—B1	−83.6 (5)	K1viii—F2—B1—F3	−2.8 (4)
K1—N1—C1—B1	41.5 (4)	K1vii—F2—B1—F3	−107.8 (3)
N1—C1—C2—C3	61.4 (5)	K1viii—F2—B1—F1	111.0 (3)
B1—C1—C2—C3	−171.2 (4)	K1vii—F2—B1—F1	6.1 (4)
C1—C2—C3—C8	−101.8 (5)	K1viii—F2—B1—C1	−126.1 (3)
C1—C2—C3—C4	79.0 (5)	K1vii—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)	K1vii—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)	K1vii—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)	K1vii—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)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···C3ix	0.95	2.93	3.528 (6)	122
C4—H4···C4ix	0.95	2.98	3.823 (6)	149
C4—H4···C5ix	0.95	3.08	3.974 (7)	158
C4—H4···C6ix	0.95	3.13	3.841 (7)	133
C4—H4···C7ix	0.95	3.09	3.556 (7)	112
C4—H4···C8ix	0.95	2.98	3.382 (6)	107

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) .