Potassium [1-(tert-but­oxy­carbon­yl)-1H-indol-3-yl]trifluoro­borate hemihydrate

Berionni, G.; Mayer, P.; Mayr, H.

doi:10.1107/S1600536812014225

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages m551-m552

doi:10.1107/S1600536812014225

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Potassium [1-(tert-butoxycarbonyl)-1H-indol-3-yl]trifluoroborate hemihydrate

Guillaume Berionni,^a Peter Mayer ^a ^* and Herbert Mayr ^a

^aLudwig-Maximilians-Universität, Department of Chemistry, Butenandtstrasse 5–13, 81377 München, Germany
^*Correspondence e-mail: pemay@cup.uni-muenchen.de

(Received 13 March 2012; accepted 2 April 2012; online 6 April 2012)

The asymmetric unit of the title salt, K⁺·C₁₃H₁₄BF₃NO₂·0.5H₂O, consists of two derivatized indolyltrifluoridoborate anions, two potassium cations and one water molecule. Within the indolyltrifluoroborate anions, the least-square planes consisting of the carboxyl group and the adjacent quarternary C atom of the tert-butyl groups deviate significantly from coplanarity with the indolyl planes [20.44 (11) and 21.02 (10)°]. The potassium ions are coordinated by six atoms (one K⁺ ion by two O and four F atoms, and the second K⁺ ion by one O and five F atoms), however, one of the potassium ions undergoes an additional weak potassium–π interaction (K⋯centroid = 3.722 Å). The packing is stabilized by sequential O—H⋯O hydrogen bonds along [100] between water molecules and also by O—H⋯F hydrogen bonds.

Related literature

For background to organotrifluoroborates and the synthesis, see: Mothes et al. (2008 ); Molander et al. (2009 ); Kassis et al. (2009 ); Reiter et al. (2010 ); Darses & Genet (2008 ). For related structures, see: Baran et al. (2005 ); Davies et al. (2005 , 2007 ); Lu & Lin (2011 ).

Experimental

Crystal data

K⁺·C₁₃H₁₄BF₃NO₂·0.5H₂O
M_r = 332.17
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.8428 (1) Å
b = 16.3177 (2) Å
c = 32.1286 (5) Å
V = 3063.17 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.38 mm⁻¹
T = 173 K
0.27 × 0.19 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer
24771 measured reflections
7001 independent reflections
6369 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.075
S = 1.03
7001 reflections
400 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.24 e Å⁻³
Absolute structure: Flack (1983 ), 2995 Friedel pairs
Flack parameter: 0.00 (3)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H51⋯F3ⁱ	0.81 (1)	2.14 (1)	2.903 (2)	156 (3)
O5—H51⋯F1ⁱ	0.81 (1)	2.62 (2)	3.188 (2)	128 (2)
O5—H52⋯O5ⁱⁱ	0.81 (1)	2.41 (1)	3.1968 (16)	164 (3)
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y-{\script{1\over 2}}, -z]$ ; (ii) $[x-{\script{1\over 2}}, -y-{\script{1\over 2}}, -z]$ .

Data collection: COLLECT (Hooft, 2004 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812014225/hp2034sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812014225/hp2034Isup2.hkl

checkCIF report

Comment top

Organotrifluoroborates and, in particular, indolyltrifluoroborates [Molander et al. (2009), Kassis et al. (2009), Reiter et al. (2010)] are synthetically useful nucleophiles for Suzuki-Miyaura cross-coupling and other CC bond-forming reactions [Darses & Genet (2008)].

The asymmetric unit contains two formula units of the title compound (Fig. 1). The B–C bond distances in the two indolyltrifluoroborate anions are found to be 1.596 (3) Å and 1.600 (3) Å. These bond distances are close to the mean distance of 1.619 Å determined from 33 crystal structures of organotrifluoroborates (CSD version 5.33, Nov 2011). In the title compound, the 1-tert-butoxycarbonyl group is not coplanar with the indolyl ring, but deviates with plane-plane angles of 20.44 (11)° and 21.02 (10)°, in which the plane of a tert-butoxycarbonyl group is defined by its C and O atoms with the exception of the methyl groups. This structural feature is observed in several of the dozen of crystal structures of 3-substituted 1-(tert-Butoxycarbonyl)-1H-indolyl derivatives [Baran et al. (2005), Davies et al. (2005), Davies et al. (2007) and Lu & Lin (2011)].

The coordination sphere of K1 consists of two oxygen atoms and four fluorine atoms in bond distances ranging between 2.58 Å and 2.99 Å. Additionally the five-membered ring of an adjacent indolyl moiety is bound by a weak potassium-π interaction (distance K1–Cg(N2, C14—C17) = 3.722 Å). The other potassium ion is coordinated by five fluorine atoms and one oxygen atom in bond distances ranging from 2.62 Å to 2.77 Å. The water molecule is coordinated solely to K1 and forms sequential hydrogen bonds of the type O–H···O along [100]. The other proton of the water molecule acts as donor in hydrogen bonds of the type O–H···F. Layers parallel to ab are formed by the combination of hydrogen bonds and coordination of the potassium ions (Fig. 2). Weak C–H···π interactions between methyl-hydrogen atoms and the six-membered rings of the indolyl moieties are established with C···Cg distances of 3.836 (3) Å and 3.715 (2) Å. The packing of the title compound is shown in Fig. 3.

Related literature top

For background to organotrifluoroborates and the synthesis, see: Mothes et al. (2008); Molander et al. (2009); Kassis et al. (2009); Reiter et al. (2010); Darses & Genet (2008). For related structures, see: Baran et al. (2005); Davies et al. (2005,2007); Lu & Lin (2011).

Experimental top

In a 100 ml Schlenck flask under argon, 1.00 g (2.92 mmol,1 eq.) of tert-butyl-3-iodo-1H-indole-1-carboxylate [Mothes et al. (2008)] was dissolved in 20 ml of freshly distilled THF and cooled to -78 °C. With a syringe, 1.37 ml of nBuLi (2.13 M in hexane, 2.92 mmol,1 eq.) was added dropwise, and the solution was stirred for 30 min at this temperature whilst turning orange pale. Neat triisopropyl borate (3.36 mmol, 0.55 ml, 1.15 eq.) was then slowly dropped to the mixture, and after removing the cooling bath the temperature reached 0 °C in 30 min. An aqueous solution of KHF₂ (17.5 mmol, 1.35 g, 6 eq. dissolved in 5 ml of H₂O) was added slowly to the limpid solution under vigorous stirring and after 15 minutes the solvents were removed in vacuo. The waxy solid was dissolved in 50 ml of hot acetone and filtrated. The filtrate was concentrated to 10 ml before adding 10 ml of diethylether. After one night in the fridge, colorless crystalline plates of the title compound were obtained (650 mg, 70%).

Computing details top

Data collection: COLLECT (Hooft, 2004); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structures of the asymmetric unit (contains two formula units of the title compound), with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level) for non-H atoms.
	Fig. 2. View on a layer formed by potassium ions and their coordinating O and F atoms. All other atoms have been omitted for clarity. Dashed lines indicate hydrogen bonds, fat solid lines K–O and K–F bonds.
	Fig. 3. The packing of the title compound viewed along [100]. Hydrogen atoms have been omitted for clarity. Fragments located outside the unit cell have been completed.

Potassium [1-(tert-butoxycarbonyl)-1H-indol-3-yl]trifluoroborate hemihydrate top

Crystal data top

K⁺·C₁₃H₁₄BF₃NO₂·0.5H₂O	F(000) = 1368
M_r = 332.17	D_x = 1.441 (1) Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 12366 reflections
a = 5.8428 (1) Å	θ = 3.1–27.5°
b = 16.3177 (2) Å	µ = 0.38 mm⁻¹
c = 32.1286 (5) Å	T = 173 K
V = 3063.17 (8) Å³	Block, colourless
Z = 8	0.27 × 0.19 × 0.10 mm

Data collection top

Nonius KappaCCD diffractometer	6369 reflections with I > 2σ(I)
Radiation source: rotating anode	R_int = 0.027
MONTEL, graded multilayered X-ray optics monochromator	θ_max = 27.5°, θ_min = 3.1°
CCD; rotation images scans	h = −7→7
24771 measured reflections	k = −21→21
7001 independent reflections	l = −41→41

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)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.075	w = 1/[σ²(F_o²) + (0.0299P)² + 1.0137P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
7001 reflections	Δρ_max = 0.30 e Å⁻³
400 parameters	Δρ_min = −0.24 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 2995 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (3)

Crystal data top

K⁺·C₁₃H₁₄BF₃NO₂·0.5H₂O	V = 3063.17 (8) Å³
M_r = 332.17	Z = 8
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.8428 (1) Å	µ = 0.38 mm⁻¹
b = 16.3177 (2) Å	T = 173 K
c = 32.1286 (5) Å	0.27 × 0.19 × 0.10 mm

Data collection top

Nonius KappaCCD diffractometer	6369 reflections with I > 2σ(I)
24771 measured reflections	R_int = 0.027
7001 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.075	Δρ_max = 0.30 e Å⁻³
S = 1.03	Δρ_min = −0.24 e Å⁻³
7001 reflections	Absolute structure: Flack (1983), 2995 Friedel pairs
400 parameters	Absolute structure parameter: 0.00 (3)
2 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 > 2σ(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	0.23271 (7)	−0.07549 (2)	−0.010496 (14)	0.03663 (10)
K2	−0.44437 (8)	0.16361 (2)	0.030974 (13)	0.03596 (10)
F1	−0.1583 (2)	−0.09666 (9)	0.02545 (4)	0.0531 (3)
F2	−0.4208 (3)	0.00302 (7)	0.02809 (4)	0.0579 (4)
F3	−0.4763 (2)	−0.11459 (8)	0.06318 (4)	0.0515 (3)
F4	1.2008 (3)	0.08962 (7)	−0.00590 (4)	0.0599 (4)
F5	0.9079 (2)	0.17683 (7)	−0.01961 (4)	0.0475 (3)
F6	1.2432 (2)	0.19073 (7)	−0.05353 (4)	0.0441 (3)
O1	0.2775 (2)	0.13553 (7)	0.17310 (4)	0.0355 (3)
O2	0.3463 (3)	0.14600 (10)	0.10405 (4)	0.0501 (4)
O3	0.6469 (2)	−0.13910 (7)	−0.13800 (4)	0.0331 (3)
O4	0.4899 (3)	−0.10246 (8)	−0.07628 (4)	0.0427 (3)
O5	0.0801 (3)	−0.23252 (10)	−0.01815 (6)	0.0562 (4)
H51	0.097 (5)	−0.2697 (12)	−0.0347 (7)	0.067*
H52	−0.052 (2)	−0.2317 (18)	−0.0103 (9)	0.067*
N1	0.0878 (3)	0.05375 (9)	0.12880 (5)	0.0323 (3)
N2	0.7777 (3)	−0.02748 (9)	−0.10475 (4)	0.0294 (3)
C1	0.0068 (3)	0.03130 (11)	0.08919 (6)	0.0332 (4)
H1	0.0749	0.0484	0.0638	0.040*
C2	−0.1791 (3)	−0.01743 (10)	0.09157 (6)	0.0289 (4)
C3	−0.2240 (3)	−0.02728 (10)	0.13595 (5)	0.0285 (4)
C4	−0.0545 (3)	0.01594 (10)	0.15856 (5)	0.0290 (4)
C5	−0.0473 (4)	0.01580 (11)	0.20163 (6)	0.0362 (4)
H5	0.0708	0.0433	0.2164	0.043*
C6	−0.2203 (4)	−0.02636 (12)	0.22244 (6)	0.0404 (5)
H6	−0.2196	−0.0279	0.2520	0.049*
C7	−0.3937 (4)	−0.06622 (12)	0.20090 (6)	0.0412 (5)
H7	−0.5118	−0.0930	0.2160	0.049*
C8	−0.3975 (3)	−0.06758 (11)	0.15802 (6)	0.0339 (4)
H8	−0.5162	−0.0955	0.1436	0.041*
C9	0.2502 (4)	0.11582 (11)	0.13339 (6)	0.0343 (4)
C10	0.4090 (4)	0.21055 (11)	0.18483 (6)	0.0359 (4)
C11	0.6548 (4)	0.20440 (15)	0.17096 (10)	0.0607 (7)
H11A	0.7180	0.1515	0.1796	0.091*
H11B	0.7438	0.2488	0.1836	0.091*
H11C	0.6625	0.2090	0.1406	0.091*
C12	0.2916 (4)	0.28447 (12)	0.16649 (8)	0.0499 (6)
H12A	0.3055	0.2831	0.1361	0.075*
H12B	0.3636	0.3344	0.1772	0.075*
H12C	0.1294	0.2839	0.1742	0.075*
C13	0.3855 (7)	0.20916 (19)	0.23156 (8)	0.0838 (11)
H13A	0.2229	0.2093	0.2391	0.126*
H13B	0.4599	0.2577	0.2434	0.126*
H13C	0.4583	0.1596	0.2426	0.126*
C14	0.8113 (3)	0.02142 (11)	−0.06941 (6)	0.0318 (4)
H14	0.7153	0.0204	−0.0456	0.038*
C15	0.9966 (3)	0.07020 (10)	−0.07336 (5)	0.0275 (4)
C16	1.0897 (3)	0.05186 (9)	−0.11437 (5)	0.0258 (3)
C17	0.9503 (3)	−0.00726 (10)	−0.13362 (5)	0.0265 (3)
C18	0.9858 (3)	−0.03336 (11)	−0.17426 (6)	0.0341 (4)
H18	0.8871	−0.0719	−0.1873	0.041*
C19	1.1730 (4)	−0.00034 (13)	−0.19486 (6)	0.0416 (5)
H19	1.2024	−0.0166	−0.2227	0.050*
C20	1.3184 (4)	0.05562 (12)	−0.17607 (7)	0.0412 (5)
H20	1.4465	0.0760	−0.1911	0.049*
C21	1.2797 (3)	0.08230 (11)	−0.13564 (6)	0.0334 (4)
H21	1.3802	0.1204	−0.1228	0.040*
C22	0.6229 (3)	−0.09235 (11)	−0.10457 (6)	0.0318 (4)
C23	0.5320 (3)	−0.22094 (11)	−0.14000 (6)	0.0335 (4)
C24	0.2743 (4)	−0.21102 (13)	−0.14087 (9)	0.0508 (6)
H24A	0.2026	−0.2642	−0.1466	0.076*
H24B	0.2320	−0.1720	−0.1627	0.076*
H24C	0.2214	−0.1905	−0.1139	0.076*
C25	0.6211 (4)	−0.25395 (13)	−0.18113 (7)	0.0471 (5)
H25A	0.7885	−0.2570	−0.1802	0.071*
H25B	0.5741	−0.2173	−0.2038	0.071*
H25C	0.5581	−0.3088	−0.1860	0.071*
C26	0.6157 (4)	−0.27308 (13)	−0.10437 (7)	0.0478 (5)
H26A	0.7833	−0.2720	−0.1036	0.072*
H26B	0.5631	−0.3296	−0.1082	0.072*
H26C	0.5550	−0.2515	−0.0781	0.072*
B1	−0.3097 (3)	−0.05677 (11)	0.05280 (6)	0.0262 (4)
B2	1.0867 (4)	0.13229 (12)	−0.03848 (6)	0.0298 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
K1	0.0355 (2)	0.03093 (19)	0.0434 (2)	−0.00376 (18)	0.00348 (19)	−0.00575 (17)
K2	0.0414 (2)	0.02571 (18)	0.0408 (2)	−0.00664 (17)	0.00910 (19)	−0.00547 (16)
F1	0.0414 (7)	0.0679 (8)	0.0500 (7)	−0.0022 (6)	0.0071 (6)	−0.0286 (6)
F2	0.0777 (9)	0.0317 (6)	0.0642 (8)	0.0021 (7)	−0.0338 (8)	−0.0013 (5)
F3	0.0583 (8)	0.0541 (7)	0.0420 (7)	−0.0296 (7)	0.0088 (6)	−0.0065 (5)
F4	0.0919 (11)	0.0359 (6)	0.0519 (7)	−0.0013 (7)	−0.0370 (8)	−0.0022 (5)
F5	0.0419 (7)	0.0433 (6)	0.0574 (8)	−0.0076 (6)	0.0157 (6)	−0.0225 (5)
F6	0.0435 (7)	0.0332 (6)	0.0558 (7)	−0.0152 (6)	0.0148 (6)	−0.0137 (5)
O1	0.0416 (8)	0.0321 (6)	0.0327 (7)	−0.0097 (6)	−0.0022 (6)	−0.0023 (5)
O2	0.0538 (10)	0.0598 (10)	0.0367 (8)	−0.0258 (8)	0.0127 (7)	−0.0080 (7)
O3	0.0378 (7)	0.0276 (6)	0.0340 (7)	−0.0098 (5)	−0.0004 (6)	−0.0035 (5)
O4	0.0422 (8)	0.0414 (8)	0.0446 (8)	−0.0145 (7)	0.0127 (7)	−0.0065 (6)
O5	0.0654 (11)	0.0346 (8)	0.0688 (12)	−0.0079 (8)	0.0163 (10)	−0.0192 (7)
N1	0.0332 (9)	0.0338 (8)	0.0298 (8)	−0.0077 (7)	0.0014 (7)	−0.0021 (6)
N2	0.0310 (8)	0.0291 (7)	0.0280 (7)	−0.0059 (6)	0.0025 (6)	−0.0019 (6)
C1	0.0350 (10)	0.0363 (9)	0.0283 (9)	−0.0063 (8)	0.0040 (7)	−0.0039 (7)
C2	0.0301 (9)	0.0234 (8)	0.0333 (9)	−0.0002 (7)	0.0028 (7)	−0.0010 (7)
C3	0.0303 (9)	0.0227 (8)	0.0325 (9)	0.0042 (7)	0.0031 (7)	0.0001 (6)
C4	0.0293 (9)	0.0264 (8)	0.0314 (9)	0.0032 (8)	0.0017 (8)	0.0022 (7)
C5	0.0416 (11)	0.0345 (9)	0.0324 (9)	0.0009 (9)	−0.0057 (9)	0.0041 (7)
C6	0.0509 (13)	0.0414 (10)	0.0290 (9)	0.0011 (10)	0.0012 (9)	0.0050 (8)
C7	0.0468 (12)	0.0350 (10)	0.0418 (11)	−0.0037 (9)	0.0098 (10)	0.0040 (8)
C8	0.0343 (10)	0.0276 (9)	0.0399 (10)	0.0001 (8)	0.0030 (8)	0.0008 (7)
C9	0.0343 (10)	0.0336 (9)	0.0350 (9)	−0.0044 (9)	0.0017 (9)	−0.0044 (7)
C10	0.0375 (11)	0.0302 (9)	0.0400 (10)	−0.0056 (8)	−0.0069 (9)	−0.0050 (8)
C11	0.0311 (11)	0.0428 (12)	0.108 (2)	0.0024 (10)	−0.0107 (13)	−0.0169 (13)
C12	0.0343 (12)	0.0331 (10)	0.0822 (17)	0.0015 (9)	−0.0019 (11)	0.0036 (10)
C13	0.135 (3)	0.0742 (19)	0.0425 (14)	−0.054 (2)	−0.0084 (17)	−0.0072 (13)
C14	0.0348 (10)	0.0327 (9)	0.0279 (9)	−0.0042 (8)	0.0026 (7)	−0.0050 (7)
C15	0.0310 (9)	0.0241 (8)	0.0274 (8)	−0.0007 (7)	0.0005 (7)	0.0006 (6)
C16	0.0274 (9)	0.0205 (7)	0.0296 (9)	0.0013 (7)	0.0011 (7)	0.0028 (6)
C17	0.0276 (8)	0.0230 (8)	0.0290 (8)	0.0011 (7)	−0.0007 (7)	0.0024 (6)
C18	0.0435 (11)	0.0300 (9)	0.0290 (9)	−0.0046 (8)	0.0016 (8)	−0.0018 (7)
C19	0.0533 (13)	0.0384 (10)	0.0331 (10)	−0.0045 (10)	0.0127 (9)	−0.0047 (8)
C20	0.0435 (11)	0.0372 (10)	0.0429 (11)	−0.0076 (9)	0.0174 (9)	−0.0015 (8)
C21	0.0319 (10)	0.0286 (8)	0.0396 (10)	−0.0046 (8)	0.0031 (8)	−0.0010 (7)
C22	0.0317 (10)	0.0298 (9)	0.0338 (9)	−0.0054 (7)	−0.0013 (8)	−0.0011 (7)
C23	0.0301 (10)	0.0268 (8)	0.0435 (10)	−0.0073 (8)	−0.0057 (8)	−0.0037 (7)
C24	0.0318 (11)	0.0388 (11)	0.0818 (17)	−0.0052 (9)	−0.0098 (11)	−0.0083 (11)
C25	0.0520 (14)	0.0404 (11)	0.0488 (13)	−0.0093 (10)	−0.0064 (11)	−0.0128 (9)
C26	0.0493 (14)	0.0346 (10)	0.0595 (14)	−0.0018 (10)	−0.0088 (11)	0.0058 (10)
B1	0.0258 (10)	0.0216 (9)	0.0313 (10)	0.0000 (7)	0.0003 (8)	−0.0012 (7)
B2	0.0339 (11)	0.0230 (9)	0.0325 (10)	−0.0025 (8)	−0.0013 (9)	−0.0011 (7)

Geometric parameters (Å, º) top

K1—F1	2.5832 (13)	C3—C4	1.416 (3)
K1—O4	2.6303 (14)	C4—C5	1.384 (2)
K1—F2ⁱ	2.6977 (13)	C5—C6	1.394 (3)
K1—F4ⁱⁱ	2.7048 (12)	C5—H5	0.9500
K1—O5	2.7243 (16)	C6—C7	1.389 (3)
K1—F3ⁱ	2.9833 (14)	C6—H6	0.9500
K1—B1ⁱ	3.373 (2)	C7—C8	1.378 (3)
K1—C15ⁱⁱ	3.4111 (17)	C7—H7	0.9500
K1—C14ⁱⁱ	3.485 (2)	C8—H8	0.9500
K1—H52	3.05 (3)	C10—C11	1.507 (3)
K2—F2	2.6256 (12)	C10—C12	1.508 (3)
K2—F5ⁱⁱ	2.6315 (12)	C10—C13	1.508 (3)
K2—O2ⁱⁱ	2.6627 (14)	C11—H11A	0.9800
K2—F4ⁱⁱⁱ	2.6756 (14)	C11—H11B	0.9800
K2—F6^iv	2.7158 (12)	C11—H11C	0.9800
K2—F5^iv	2.7671 (12)	C12—H12A	0.9800
K2—F6ⁱⁱⁱ	3.3016 (14)	C12—H12B	0.9800
K2—B2^iv	3.344 (2)	C12—H12C	0.9800
F1—B1	1.406 (2)	C13—H13A	0.9800
F2—B1	1.415 (2)	C13—H13B	0.9800
F2—K1ⁱⁱ	2.6977 (13)	C13—H13C	0.9800
F3—B1	1.396 (2)	C14—C15	1.350 (2)
F3—K1ⁱⁱ	2.9832 (14)	C14—K1ⁱ	3.485 (2)
F4—B2	1.423 (2)	C14—H14	0.9500
F4—K2^v	2.6756 (14)	C15—C16	1.457 (2)
F4—K1ⁱ	2.7047 (12)	C15—B2	1.600 (3)
F5—B2	1.409 (2)	C15—K1ⁱ	3.4111 (17)
F5—K2ⁱ	2.6316 (12)	C16—C21	1.395 (2)
F5—K2^vi	2.7671 (12)	C16—C17	1.406 (2)
F6—B2	1.407 (2)	C17—C18	1.389 (2)
F6—K2^vi	2.7157 (12)	C18—C19	1.387 (3)
F6—K2^v	3.3017 (14)	C18—H18	0.9500
O1—C9	1.325 (2)	C19—C20	1.386 (3)
O1—C10	1.494 (2)	C19—H19	0.9500
O2—C9	1.203 (2)	C20—C21	1.388 (3)
O2—K2ⁱ	2.6627 (14)	C20—H20	0.9500
O3—C22	1.325 (2)	C21—H21	0.9500
O3—C23	1.496 (2)	C23—C26	1.508 (3)
O4—C22	1.207 (2)	C23—C24	1.515 (3)
O5—H51	0.812 (10)	C23—C25	1.519 (3)
O5—H52	0.813 (10)	C24—H24A	0.9800
N1—C9	1.396 (2)	C24—H24B	0.9800
N1—C1	1.406 (2)	C24—H24C	0.9800
N1—C4	1.409 (2)	C25—H25A	0.9800
N2—C22	1.393 (2)	C25—H25B	0.9800
N2—C14	1.402 (2)	C25—H25C	0.9800
N2—C17	1.409 (2)	C26—H26A	0.9800
C1—C2	1.348 (3)	C26—H26B	0.9800
C1—H1	0.9500	C26—H26C	0.9800
C2—C3	1.459 (2)	B1—K1ⁱⁱ	3.373 (2)
C2—B1	1.596 (3)	B2—K2^vi	3.344 (2)
C3—C8	1.401 (3)

F1—K1—O4	147.37 (4)	K1—O5—H52	106 (2)
F1—K1—F2ⁱ	121.45 (5)	H51—O5—H52	109 (3)
O4—K1—F2ⁱ	91.15 (5)	C9—N1—C1	120.89 (15)
F1—K1—F4ⁱⁱ	92.74 (5)	C9—N1—C4	130.33 (15)
O4—K1—F4ⁱⁱ	104.47 (5)	C1—N1—C4	107.54 (15)
F2ⁱ—K1—F4ⁱⁱ	63.48 (4)	C22—N2—C14	121.35 (15)
F1—K1—O5	67.98 (5)	C22—N2—C17	130.21 (15)
O4—K1—O5	87.55 (5)	C14—N2—C17	107.45 (14)
F2ⁱ—K1—O5	137.21 (5)	C2—C1—N1	111.93 (16)
F4ⁱⁱ—K1—O5	156.82 (6)	C2—C1—H1	124.0
F1—K1—F3ⁱ	96.93 (4)	N1—C1—H1	124.0
O4—K1—F3ⁱ	106.04 (4)	C1—C2—C3	105.39 (16)
F2ⁱ—K1—F3ⁱ	46.31 (3)	C1—C2—B1	125.33 (16)
F4ⁱⁱ—K1—F3ⁱ	102.06 (4)	C3—C2—B1	129.24 (16)
O5—K1—F3ⁱ	93.27 (5)	C8—C3—C4	118.68 (16)
F1—K1—B1ⁱ	116.33 (5)	C8—C3—C2	132.59 (17)
O4—K1—B1ⁱ	92.69 (5)	C4—C3—C2	108.70 (15)
F2ⁱ—K1—B1ⁱ	23.80 (4)	C5—C4—N1	131.36 (18)
F4ⁱⁱ—K1—B1ⁱ	86.07 (4)	C5—C4—C3	122.22 (17)
O5—K1—B1ⁱ	113.52 (6)	N1—C4—C3	106.41 (15)
F3ⁱ—K1—B1ⁱ	24.40 (4)	C4—C5—C6	117.27 (19)
F1—K1—C15ⁱⁱ	90.01 (5)	C4—C5—H5	121.4
O4—K1—C15ⁱⁱ	82.64 (5)	C6—C5—H5	121.4
F2ⁱ—K1—C15ⁱⁱ	104.16 (4)	C7—C6—C5	121.43 (18)
F4ⁱⁱ—K1—C15ⁱⁱ	46.38 (4)	C7—C6—H6	119.3
O5—K1—C15ⁱⁱ	118.01 (5)	C5—C6—H6	119.3
F3ⁱ—K1—C15ⁱⁱ	148.14 (4)	C8—C7—C6	121.14 (19)
B1ⁱ—K1—C15ⁱⁱ	127.92 (4)	C8—C7—H7	119.4
F1—K1—C14ⁱⁱ	71.25 (5)	C6—C7—H7	119.4
O4—K1—C14ⁱⁱ	92.47 (5)	C7—C8—C3	119.15 (19)
F2ⁱ—K1—C14ⁱⁱ	124.35 (4)	C7—C8—H8	120.4
F4ⁱⁱ—K1—C14ⁱⁱ	61.90 (4)	C3—C8—H8	120.4
O5—K1—C14ⁱⁱ	98.42 (5)	O2—C9—O1	126.80 (18)
F3ⁱ—K1—C14ⁱⁱ	158.52 (4)	O2—C9—N1	122.11 (17)
B1ⁱ—K1—C14ⁱⁱ	147.81 (4)	O1—C9—N1	111.08 (16)
C15ⁱⁱ—K1—C14ⁱⁱ	22.54 (4)	O1—C10—C11	111.15 (16)
F1—K1—K2ⁱ	110.59 (3)	O1—C10—C12	108.85 (16)
O4—K1—K2ⁱ	98.19 (3)	C11—C10—C12	111.8 (2)
F2ⁱ—K1—K2ⁱ	31.13 (3)	O1—C10—C13	101.06 (17)
F4ⁱⁱ—K1—K2ⁱ	32.38 (3)	C11—C10—C13	112.4 (2)
O5—K1—K2ⁱ	166.44 (5)	C12—C10—C13	111.1 (2)
F3ⁱ—K1—K2ⁱ	73.36 (2)	C10—C11—H11A	109.5
B1ⁱ—K1—K2ⁱ	54.20 (3)	C10—C11—H11B	109.5
C15ⁱⁱ—K1—K2ⁱ	75.08 (3)	H11A—C11—H11B	109.5
C14ⁱⁱ—K1—K2ⁱ	93.62 (3)	C10—C11—H11C	109.5
F1—K1—H52	53.4 (3)	H11A—C11—H11C	109.5
O4—K1—H52	100.0 (4)	H11B—C11—H11C	109.5
F2ⁱ—K1—H52	143.8 (5)	C10—C12—H12A	109.5
F4ⁱⁱ—K1—H52	142.8 (3)	C10—C12—H12B	109.5
O5—K1—H52	14.9 (3)	H12A—C12—H12B	109.5
F3ⁱ—K1—H52	97.5 (5)	C10—C12—H12C	109.5
B1ⁱ—K1—H52	120.5 (5)	H12A—C12—H12C	109.5
C15ⁱⁱ—K1—H52	111.3 (5)	H12B—C12—H12C	109.5
C14ⁱⁱ—K1—H52	89.7 (5)	C10—C13—H13A	109.5
K2ⁱ—K1—H52	161.3 (5)	C10—C13—H13B	109.5
F2—K2—F5ⁱⁱ	91.09 (5)	H13A—C13—H13B	109.5
F2—K2—O2ⁱⁱ	86.99 (5)	C10—C13—H13C	109.5
F5ⁱⁱ—K2—O2ⁱⁱ	155.88 (5)	H13A—C13—H13C	109.5
F2—K2—F4ⁱⁱⁱ	64.83 (4)	H13B—C13—H13C	109.5
F5ⁱⁱ—K2—F4ⁱⁱⁱ	111.69 (5)	C15—C14—N2	111.82 (16)
O2ⁱⁱ—K2—F4ⁱⁱⁱ	89.19 (5)	C15—C14—K1ⁱ	75.65 (11)
F2—K2—F6^iv	149.50 (4)	N2—C14—K1ⁱ	106.29 (11)
F5ⁱⁱ—K2—F6^iv	77.14 (4)	C15—C14—H14	124.1
O2ⁱⁱ—K2—F6^iv	92.55 (4)	N2—C14—H14	124.1
F4ⁱⁱⁱ—K2—F6^iv	145.66 (4)	K1ⁱ—C14—H14	88.3
F2—K2—F5^iv	161.94 (4)	C14—C15—C16	105.29 (15)
F5ⁱⁱ—K2—F5^iv	94.90 (3)	C14—C15—B2	124.85 (16)
O2ⁱⁱ—K2—F5^iv	94.27 (5)	C16—C15—B2	129.85 (15)
F4ⁱⁱⁱ—K2—F5^iv	97.15 (4)	C14—C15—K1ⁱ	81.81 (11)
F6^iv—K2—F5^iv	48.52 (3)	C16—C15—K1ⁱ	103.96 (10)
F2—K2—F6ⁱⁱⁱ	97.69 (3)	B2—C15—K1ⁱ	83.88 (10)
F5ⁱⁱ—K2—F6ⁱⁱⁱ	85.04 (4)	C21—C16—C17	119.33 (16)
O2ⁱⁱ—K2—F6ⁱⁱⁱ	119.05 (4)	C21—C16—C15	131.86 (16)
F4ⁱⁱⁱ—K2—F6ⁱⁱⁱ	42.94 (3)	C17—C16—C15	108.80 (15)
F6^iv—K2—F6ⁱⁱⁱ	108.98 (2)	C18—C17—C16	122.48 (16)
F5^iv—K2—F6ⁱⁱⁱ	65.98 (3)	C18—C17—N2	130.85 (16)
F2—K2—B2^iv	173.53 (5)	C16—C17—N2	106.60 (14)
F5ⁱⁱ—K2—B2^iv	85.44 (4)	C19—C18—C17	116.58 (18)
O2ⁱⁱ—K2—B2^iv	93.94 (5)	C19—C18—H18	121.7
F4ⁱⁱⁱ—K2—B2^iv	121.56 (5)	C17—C18—H18	121.7
F6^iv—K2—B2^iv	24.11 (4)	C20—C19—C18	122.10 (18)
F5^iv—K2—B2^iv	24.41 (4)	C20—C19—H19	119.0
F6ⁱⁱⁱ—K2—B2^iv	87.47 (4)	C18—C19—H19	118.9
F2—K2—B2ⁱⁱⁱ	82.84 (4)	C19—C20—C21	120.94 (18)
F5ⁱⁱ—K2—B2ⁱⁱⁱ	103.06 (5)	C19—C20—H20	119.5
O2ⁱⁱ—K2—B2ⁱⁱⁱ	100.55 (5)	C21—C20—H20	119.5
F4ⁱⁱⁱ—K2—B2ⁱⁱⁱ	20.62 (4)	C20—C21—C16	118.46 (17)
F6^iv—K2—B2ⁱⁱⁱ	127.00 (4)	C20—C21—H21	120.8
F5^iv—K2—B2ⁱⁱⁱ	79.22 (4)	C16—C21—H21	120.8
F6ⁱⁱⁱ—K2—B2ⁱⁱⁱ	23.21 (4)	O4—C22—O3	126.87 (17)
B2^iv—K2—B2ⁱⁱⁱ	103.25 (5)	O4—C22—N2	121.69 (17)
F2—K2—K2^vii	129.84 (3)	O3—C22—N2	111.43 (15)
F5ⁱⁱ—K2—K2^vii	100.51 (3)	O3—C23—C26	109.01 (15)
O2ⁱⁱ—K2—K2^vii	99.12 (4)	O3—C23—C24	110.57 (16)
F4ⁱⁱⁱ—K2—K2^vii	65.53 (3)	C26—C23—C24	113.36 (19)
F6^iv—K2—K2^vii	80.36 (3)	O3—C23—C25	101.55 (15)
F5^iv—K2—K2^vii	32.19 (2)	C26—C23—C25	110.46 (18)
F6ⁱⁱⁱ—K2—K2^vii	36.60 (2)	C24—C23—C25	111.24 (19)
B2^iv—K2—K2^vii	56.35 (4)	C23—C24—H24A	109.5
B2ⁱⁱⁱ—K2—K2^vii	47.03 (3)	C23—C24—H24B	109.5
F2—K2—K2^viii	124.95 (4)	H24A—C24—H24B	109.5
F5ⁱⁱ—K2—K2^viii	34.07 (2)	C23—C24—H24C	109.5
O2ⁱⁱ—K2—K2^viii	138.78 (3)	H24A—C24—H24C	109.5
F4ⁱⁱⁱ—K2—K2^viii	125.95 (3)	H24B—C24—H24C	109.5
F6^iv—K2—K2^viii	46.46 (3)	C23—C25—H25A	109.5
F5^iv—K2—K2^viii	63.69 (3)	C23—C25—H25B	109.5
F6ⁱⁱⁱ—K2—K2^viii	84.93 (2)	H25A—C25—H25B	109.5
B2^iv—K2—K2^viii	51.37 (4)	C23—C25—H25C	109.5
B2ⁱⁱⁱ—K2—K2^viii	108.06 (4)	H25A—C25—H25C	109.5
K2^vii—K2—K2^viii	80.496 (13)	H25B—C25—H25C	109.5
F2—K2—K1ⁱⁱ	32.08 (3)	C23—C26—H26A	109.5
F5ⁱⁱ—K2—K1ⁱⁱ	102.39 (3)	C23—C26—H26B	109.5
O2ⁱⁱ—K2—K1ⁱⁱ	88.57 (3)	H26A—C26—H26B	109.5
F4ⁱⁱⁱ—K2—K1ⁱⁱ	32.77 (3)	C23—C26—H26C	109.5
F6^iv—K2—K1ⁱⁱ	178.10 (3)	H26A—C26—H26C	109.5
F5^iv—K2—K1ⁱⁱ	129.88 (3)	H26B—C26—H26C	109.5
F6ⁱⁱⁱ—K2—K1ⁱⁱ	69.12 (2)	F3—B1—F1	105.97 (14)
B2^iv—K2—K1ⁱⁱ	154.26 (4)	F3—B1—F2	106.27 (15)
B2ⁱⁱⁱ—K2—K1ⁱⁱ	51.23 (3)	F1—B1—F2	104.90 (16)
K2^vii—K2—K1ⁱⁱ	97.952 (11)	F3—B1—C2	114.77 (15)
K2^viii—K2—K1ⁱⁱ	132.537 (15)	F1—B1—C2	111.89 (15)
B1—F1—K1	140.70 (11)	F2—B1—C2	112.31 (14)
B1—F2—K2	133.82 (11)	F3—B1—K1ⁱⁱ	61.98 (9)
B1—F2—K1ⁱⁱ	105.92 (10)	F1—B1—K1ⁱⁱ	94.60 (10)
K2—F2—K1ⁱⁱ	116.79 (5)	F2—B1—K1ⁱⁱ	50.28 (8)
B1—F3—K1ⁱⁱ	93.63 (10)	C2—B1—K1ⁱⁱ	152.40 (12)
B2—F4—K2^v	117.91 (11)	F6—B2—F5	106.25 (14)
B2—F4—K1ⁱ	118.65 (10)	F6—B2—F4	106.25 (16)
K2^v—F4—K1ⁱ	114.86 (5)	F5—B2—F4	106.46 (16)
B2—F5—K2ⁱ	143.41 (11)	F6—B2—C15	113.72 (15)
B2—F5—K2^vi	101.39 (10)	F5—B2—C15	112.58 (16)
K2ⁱ—F5—K2^vi	113.74 (4)	F4—B2—C15	111.08 (14)
B2—F6—K2^vi	103.84 (10)	F6—B2—K2^vi	52.05 (8)
B2—F6—K2^v	89.19 (10)	F5—B2—K2^vi	54.21 (8)
K2^vi—F6—K2^v	96.95 (3)	F4—B2—K2^vi	117.36 (11)
C9—O1—C10	120.25 (14)	C15—B2—K2^vi	131.55 (12)
C9—O2—K2ⁱ	161.75 (14)	F6—B2—K2^v	67.61 (10)
C22—O3—C23	120.08 (14)	F5—B2—K2^v	103.06 (11)
C22—O4—K1	161.78 (13)	C15—B2—K2^v	141.36 (12)
K1—O5—H51	136 (2)	K2^vi—B2—K2^v	81.60 (4)

O4—K1—F1—B1	−147.17 (17)	C21—C16—C17—N2	178.67 (15)
F2ⁱ—K1—F1—B1	35.8 (2)	C15—C16—C17—N2	−1.82 (18)
F4ⁱⁱ—K1—F1—B1	−24.58 (19)	C22—N2—C17—C18	16.4 (3)
O5—K1—F1—B1	168.7 (2)	C14—N2—C17—C18	−175.10 (19)
F3ⁱ—K1—F1—B1	77.93 (19)	C22—N2—C17—C16	−166.55 (17)
B1ⁱ—K1—F1—B1	62.39 (19)	C14—N2—C17—C16	1.93 (18)
C15ⁱⁱ—K1—F1—B1	−70.90 (19)	C16—C17—C18—C19	2.4 (3)
C14ⁱⁱ—K1—F1—B1	−83.63 (19)	N2—C17—C18—C19	178.99 (18)
K2ⁱ—K1—F1—B1	3.15 (19)	C17—C18—C19—C20	0.2 (3)
F5ⁱⁱ—K2—F2—B1	92.47 (17)	C18—C19—C20—C21	−1.2 (3)
O2ⁱⁱ—K2—F2—B1	−63.47 (17)	C19—C20—C21—C16	−0.4 (3)
F4ⁱⁱⁱ—K2—F2—B1	−153.99 (18)	C17—C16—C21—C20	2.9 (3)
F6^iv—K2—F2—B1	26.4 (2)	C15—C16—C21—C20	−176.48 (19)
F5^iv—K2—F2—B1	−158.03 (15)	K1—O4—C22—O3	−162.5 (3)
F6ⁱⁱⁱ—K2—F2—B1	177.62 (17)	K1—O4—C22—N2	18.9 (6)
B2ⁱⁱⁱ—K2—F2—B1	−164.50 (18)	C23—O3—C22—O4	−11.1 (3)
K2^vii—K2—F2—B1	−162.85 (15)	C23—O3—C22—N2	167.62 (15)
K2^viii—K2—F2—B1	88.44 (17)	C14—N2—C22—O4	10.1 (3)
K1ⁱⁱ—K2—F2—B1	−155.6 (2)	C17—N2—C22—O4	177.22 (18)
F5ⁱⁱ—K2—F2—K1ⁱⁱ	−111.94 (6)	C14—N2—C22—O3	−168.73 (16)
O2ⁱⁱ—K2—F2—K1ⁱⁱ	92.12 (7)	C17—N2—C22—O3	−1.6 (3)
F4ⁱⁱⁱ—K2—F2—K1ⁱⁱ	1.60 (6)	C22—O3—C23—C26	−59.2 (2)
F6^iv—K2—F2—K1ⁱⁱ	−177.97 (6)	C22—O3—C23—C24	66.1 (2)
F5^iv—K2—F2—K1ⁱⁱ	−2.4 (2)	C22—O3—C23—C25	−175.75 (16)
F6ⁱⁱⁱ—K2—F2—K1ⁱⁱ	−26.80 (7)	K1ⁱⁱ—F3—B1—F1	−86.68 (13)
B2ⁱⁱⁱ—K2—F2—K1ⁱⁱ	−8.92 (6)	K1ⁱⁱ—F3—B1—F2	24.56 (13)
K2^vii—K2—F2—K1ⁱⁱ	−7.26 (9)	K1ⁱⁱ—F3—B1—C2	149.32 (13)
K2^viii—K2—F2—K1ⁱⁱ	−115.98 (5)	K1—F1—B1—F3	−170.68 (12)
F1—K1—O4—C22	137.5 (4)	K1—F1—B1—F2	77.1 (2)
F2ⁱ—K1—O4—C22	−45.0 (4)	K1—F1—B1—C2	−44.9 (2)
F4ⁱⁱ—K1—O4—C22	17.9 (4)	K1—F1—B1—K1ⁱⁱ	127.17 (15)
O5—K1—O4—C22	177.8 (4)	K2—F2—B1—F3	128.95 (14)
F3ⁱ—K1—O4—C22	−89.5 (4)	K1ⁱⁱ—F2—B1—F3	−28.49 (15)
B1ⁱ—K1—O4—C22	−68.7 (4)	K2—F2—B1—F1	−119.07 (15)
C15ⁱⁱ—K1—O4—C22	59.1 (4)	K1ⁱⁱ—F2—B1—F1	83.50 (13)
C14ⁱⁱ—K1—O4—C22	79.5 (4)	K2—F2—B1—C2	2.7 (2)
K2ⁱ—K1—O4—C22	−14.5 (4)	K1ⁱⁱ—F2—B1—C2	−154.75 (12)
C9—N1—C1—C2	−167.77 (17)	K2—F2—B1—K1ⁱⁱ	157.44 (19)
C4—N1—C1—C2	0.8 (2)	C1—C2—B1—F3	170.96 (17)
N1—C1—C2—C3	0.3 (2)	C3—C2—B1—F3	−6.6 (3)
N1—C1—C2—B1	−177.75 (16)	C1—C2—B1—F1	50.2 (2)
C1—C2—C3—C8	176.85 (19)	C3—C2—B1—F1	−127.44 (19)
B1—C2—C3—C8	−5.2 (3)	C1—C2—B1—F2	−67.5 (2)
C1—C2—C3—C4	−1.3 (2)	C3—C2—B1—F2	114.9 (2)
B1—C2—C3—C4	176.68 (16)	C1—C2—B1—K1ⁱⁱ	−112.6 (3)
C9—N1—C4—C5	−14.9 (3)	C3—C2—B1—K1ⁱⁱ	69.8 (3)
C1—N1—C4—C5	178.0 (2)	K2^vi—F6—B2—F5	0.78 (16)
C9—N1—C4—C3	165.54 (18)	K2^v—F6—B2—F5	97.73 (13)
C1—N1—C4—C3	−1.53 (19)	K2^vi—F6—B2—F4	−112.32 (13)
C8—C3—C4—C5	3.7 (3)	K2^v—F6—B2—F4	−15.37 (13)
C2—C3—C4—C5	−177.83 (17)	K2^vi—F6—B2—C15	125.18 (13)
C8—C3—C4—N1	−176.70 (15)	K2^v—F6—B2—C15	−137.87 (14)
C2—C3—C4—N1	1.74 (19)	K2^v—F6—B2—K2^vi	96.95 (5)
N1—C4—C5—C6	178.10 (18)	K2^vi—F6—B2—K2^v	−96.95 (5)
C3—C4—C5—C6	−2.5 (3)	K2ⁱ—F5—B2—F6	−164.53 (12)
C4—C5—C6—C7	−0.4 (3)	K2^vi—F5—B2—F6	−0.76 (15)
C5—C6—C7—C8	1.9 (3)	K2ⁱ—F5—B2—F4	−51.6 (2)
C6—C7—C8—C3	−0.6 (3)	K2^vi—F5—B2—F4	112.20 (12)
C4—C3—C8—C7	−2.1 (3)	K2ⁱ—F5—B2—C15	70.4 (2)
C2—C3—C8—C7	179.89 (19)	K2^vi—F5—B2—C15	−125.86 (12)
K2ⁱ—O2—C9—O1	142.3 (4)	K2ⁱ—F5—B2—K2^vi	−163.8 (2)
K2ⁱ—O2—C9—N1	−38.6 (6)	K2ⁱ—F5—B2—K2^v	−94.39 (17)
C10—O1—C9—O2	10.7 (3)	K2^vi—F5—B2—K2^v	69.38 (8)
C10—O1—C9—N1	−168.51 (15)	K2^v—F4—B2—F6	21.72 (18)
C1—N1—C9—O2	−8.6 (3)	K1ⁱ—F4—B2—F6	−124.53 (12)
C4—N1—C9—O2	−174.2 (2)	K2^v—F4—B2—F5	−91.24 (15)
C1—N1—C9—O1	170.70 (17)	K1ⁱ—F4—B2—F5	122.51 (12)
C4—N1—C9—O1	5.1 (3)	K2^v—F4—B2—C15	145.88 (12)
C9—O1—C10—C11	−62.8 (2)	K1ⁱ—F4—B2—C15	−0.4 (2)
C9—O1—C10—C12	60.7 (2)	K2^v—F4—B2—K2^vi	−33.50 (17)
C9—O1—C10—C13	177.7 (2)	K1ⁱ—F4—B2—K2^vi	−179.74 (6)
C22—N2—C14—C15	168.35 (16)	K1ⁱ—F4—B2—K2^v	−146.25 (17)
C17—N2—C14—C15	−1.4 (2)	C14—C15—B2—F6	−164.37 (17)
C22—N2—C14—K1ⁱ	87.62 (16)	C16—C15—B2—F6	17.0 (3)
C17—N2—C14—K1ⁱ	−82.10 (13)	K1ⁱ—C15—B2—F6	120.06 (14)
N2—C14—C15—C16	0.2 (2)	C14—C15—B2—F5	−43.5 (2)
K1ⁱ—C14—C15—C16	102.32 (12)	C16—C15—B2—F5	137.88 (18)
N2—C14—C15—B2	−178.71 (16)	K1ⁱ—C15—B2—F5	−119.03 (14)
K1ⁱ—C14—C15—B2	−76.62 (16)	C14—C15—B2—F4	75.8 (2)
N2—C14—C15—K1ⁱ	−102.09 (14)	C16—C15—B2—F4	−102.8 (2)
C14—C15—C16—C21	−179.56 (18)	K1ⁱ—C15—B2—F4	0.26 (15)
B2—C15—C16—C21	−0.7 (3)	C14—C15—B2—K2^vi	−104.92 (19)
K1ⁱ—C15—C16—C21	−94.39 (19)	C16—C15—B2—K2^vi	76.4 (2)
C14—C15—C16—C17	1.01 (19)	K1ⁱ—C15—B2—K2^vi	179.51 (13)
B2—C15—C16—C17	179.87 (17)	C14—C15—B2—K2^v	112.3 (2)
K1ⁱ—C15—C16—C17	86.18 (13)	C16—C15—B2—K2^v	−66.3 (3)
C21—C16—C17—C18	−4.0 (3)	K1ⁱ—C15—B2—K2^v	36.76 (17)
C15—C16—C17—C18	175.51 (16)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H51···F3^ix	0.81 (1)	2.14 (1)	2.903 (2)	156 (3)
O5—H51···F1^ix	0.81 (1)	2.62 (2)	3.188 (2)	128 (2)
O5—H52···O5^x	0.81 (1)	2.41 (1)	3.1968 (16)	164 (3)

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

Experimental details

Crystal data
Chemical formula	K⁺·C₁₃H₁₄BF₃NO₂·0.5H₂O
M_r	332.17
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	173
a, b, c (Å)	5.8428 (1), 16.3177 (2), 32.1286 (5)
V (Å³)	3063.17 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.38
Crystal size (mm)	0.27 × 0.19 × 0.10

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	24771, 7001, 6369
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.075, 1.03
No. of reflections	7001
No. of parameters	400
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.24
Absolute structure	Flack (1983), 2995 Friedel pairs
Absolute structure parameter	0.00 (3)

Computer programs: COLLECT (Hooft, 2004), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H51···F3ⁱ	0.812 (10)	2.142 (14)	2.903 (2)	156 (3)
O5—H51···F1ⁱ	0.812 (10)	2.62 (2)	3.188 (2)	128 (2)
O5—H52···O5ⁱⁱ	0.813 (10)	2.406 (12)	3.1968 (16)	164 (3)

Symmetry codes: (i) x+1/2, −y−1/2, −z; (ii) x−1/2, −y−1/2, −z.

Acknowledgements

The authors thank Professor Peter Klüfers for generous allocation of diffractometer time.

References

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. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Volume 68| Part 5| May 2012| Pages m551-m552

doi:10.1107/S1600536812014225

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Potassium [1-(tert-but­­oxy­carbon­yl)-1H-indol-3-yl]tri­fluoro­borate hemihydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Potassium [1-(tert-butoxycarbonyl)-1H-indol-3-yl]trifluoroborate hemihydrate