Potassium [1-(tert-but-oxy-carbon-yl)-1H-indol-3-yl]trifluoro-borate hemihydrate.

The asymmetric unit of the title salt, K(+)·C(13)H(14)BF(3)NO(2)·0.5H(2)O, consists of two derivatized indolyltrifluoridoborate anions, two potassium cations and one water mol-ecule. Within the indolyltrifluoro-borate 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 inter-action (K⋯centroid = 3.722 Å). The packing is stabilized by sequential O-H⋯O hydrogen bonds along [100] between water mol-ecules 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 = 332.17

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.075

S = 1.03

7001 reflections

400 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.24 e Å−3

Absolute structure: Flack (1983 ▶), 2995 Friedel pairs

Flack parameter: 0.00 (3)

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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812014225/hp2034sup1.cif

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

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

K+·C13H14BF3NO2·0.5H2O	F(000) = 1368
Mr = 332.17	Dx = 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

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

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(Fo2) + (0.0299P)2 + 1.0137P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
7001 reflections	Δρmax = 0.30 e Å−3
400 parameters	Δρmin = −0.24 e Å−3
2 restraints	Absolute structure: Flack (1983), 2995 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.00 (3)

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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—F6iv	2.7158 (12)	C11—H11C	0.9800
K2—F5iv	2.7671 (12)	C12—H12A	0.9800
K2—F6iii	3.3016 (14)	C12—H12B	0.9800
K2—B2iv	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—K2v	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—K2vi	2.7671 (12)	C16—C17	1.406 (2)
F6—B2	1.407 (2)	C17—C18	1.389 (2)
F6—K2vi	2.7157 (12)	C18—C19	1.387 (3)
F6—K2v	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—K2vi	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—F6iv	149.50 (4)	N2—C14—K1i	106.29 (11)
F5ii—K2—F6iv	77.14 (4)	C15—C14—H14	124.1
O2ii—K2—F6iv	92.55 (4)	N2—C14—H14	124.1
F4iii—K2—F6iv	145.66 (4)	K1i—C14—H14	88.3
F2—K2—F5iv	161.94 (4)	C14—C15—C16	105.29 (15)
F5ii—K2—F5iv	94.90 (3)	C14—C15—B2	124.85 (16)
O2ii—K2—F5iv	94.27 (5)	C16—C15—B2	129.85 (15)
F4iii—K2—F5iv	97.15 (4)	C14—C15—K1i	81.81 (11)
F6iv—K2—F5iv	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)
F6iv—K2—F6iii	108.98 (2)	C18—C17—C16	122.48 (16)
F5iv—K2—F6iii	65.98 (3)	C18—C17—N2	130.85 (16)
F2—K2—B2iv	173.53 (5)	C16—C17—N2	106.60 (14)
F5ii—K2—B2iv	85.44 (4)	C19—C18—C17	116.58 (18)
O2ii—K2—B2iv	93.94 (5)	C19—C18—H18	121.7
F4iii—K2—B2iv	121.56 (5)	C17—C18—H18	121.7
F6iv—K2—B2iv	24.11 (4)	C20—C19—C18	122.10 (18)
F5iv—K2—B2iv	24.41 (4)	C20—C19—H19	119.0
F6iii—K2—B2iv	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)
F6iv—K2—B2iii	127.00 (4)	C20—C21—H21	120.8
F5iv—K2—B2iii	79.22 (4)	C16—C21—H21	120.8
F6iii—K2—B2iii	23.21 (4)	O4—C22—O3	126.87 (17)
B2iv—K2—B2iii	103.25 (5)	O4—C22—N2	121.69 (17)
F2—K2—K2vii	129.84 (3)	O3—C22—N2	111.43 (15)
F5ii—K2—K2vii	100.51 (3)	O3—C23—C26	109.01 (15)
O2ii—K2—K2vii	99.12 (4)	O3—C23—C24	110.57 (16)
F4iii—K2—K2vii	65.53 (3)	C26—C23—C24	113.36 (19)
F6iv—K2—K2vii	80.36 (3)	O3—C23—C25	101.55 (15)
F5iv—K2—K2vii	32.19 (2)	C26—C23—C25	110.46 (18)
F6iii—K2—K2vii	36.60 (2)	C24—C23—C25	111.24 (19)
B2iv—K2—K2vii	56.35 (4)	C23—C24—H24A	109.5
B2iii—K2—K2vii	47.03 (3)	C23—C24—H24B	109.5
F2—K2—K2viii	124.95 (4)	H24A—C24—H24B	109.5
F5ii—K2—K2viii	34.07 (2)	C23—C24—H24C	109.5
O2ii—K2—K2viii	138.78 (3)	H24A—C24—H24C	109.5
F4iii—K2—K2viii	125.95 (3)	H24B—C24—H24C	109.5
F6iv—K2—K2viii	46.46 (3)	C23—C25—H25A	109.5
F5iv—K2—K2viii	63.69 (3)	C23—C25—H25B	109.5
F6iii—K2—K2viii	84.93 (2)	H25A—C25—H25B	109.5
B2iv—K2—K2viii	51.37 (4)	C23—C25—H25C	109.5
B2iii—K2—K2viii	108.06 (4)	H25A—C25—H25C	109.5
K2vii—K2—K2viii	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
F6iv—K2—K1ii	178.10 (3)	H26A—C26—H26C	109.5
F5iv—K2—K1ii	129.88 (3)	H26B—C26—H26C	109.5
F6iii—K2—K1ii	69.12 (2)	F3—B1—F1	105.97 (14)
B2iv—K2—K1ii	154.26 (4)	F3—B1—F2	106.27 (15)
B2iii—K2—K1ii	51.23 (3)	F1—B1—F2	104.90 (16)
K2vii—K2—K1ii	97.952 (11)	F3—B1—C2	114.77 (15)
K2viii—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—K2v	117.91 (11)	F6—B2—F5	106.25 (14)
B2—F4—K1i	118.65 (10)	F6—B2—F4	106.25 (16)
K2v—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—K2vi	101.39 (10)	F5—B2—C15	112.58 (16)
K2i—F5—K2vi	113.74 (4)	F4—B2—C15	111.08 (14)
B2—F6—K2vi	103.84 (10)	F6—B2—K2vi	52.05 (8)
B2—F6—K2v	89.19 (10)	F5—B2—K2vi	54.21 (8)
K2vi—F6—K2v	96.95 (3)	F4—B2—K2vi	117.36 (11)
C9—O1—C10	120.25 (14)	C15—B2—K2vi	131.55 (12)
C9—O2—K2i	161.75 (14)	F6—B2—K2v	67.61 (10)
C22—O3—C23	120.08 (14)	F5—B2—K2v	103.06 (11)
C22—O4—K1	161.78 (13)	C15—B2—K2v	141.36 (12)
K1—O5—H51	136 (2)	K2vi—B2—K2v	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)
F6iv—K2—F2—B1	26.4 (2)	C15—C16—C21—C20	−176.48 (19)
F5iv—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)
K2vii—K2—F2—B1	−162.85 (15)	C23—O3—C22—N2	167.62 (15)
K2viii—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)
F6iv—K2—F2—K1ii	−177.97 (6)	C22—O3—C23—C24	66.1 (2)
F5iv—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)
K2vii—K2—F2—K1ii	−7.26 (9)	K1ii—F3—B1—C2	149.32 (13)
K2viii—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)	K2vi—F6—B2—F5	0.78 (16)
C9—N1—C4—C3	165.54 (18)	K2v—F6—B2—F5	97.73 (13)
C1—N1—C4—C3	−1.53 (19)	K2vi—F6—B2—F4	−112.32 (13)
C8—C3—C4—C5	3.7 (3)	K2v—F6—B2—F4	−15.37 (13)
C2—C3—C4—C5	−177.83 (17)	K2vi—F6—B2—C15	125.18 (13)
C8—C3—C4—N1	−176.70 (15)	K2v—F6—B2—C15	−137.87 (14)
C2—C3—C4—N1	1.74 (19)	K2v—F6—B2—K2vi	96.95 (5)
N1—C4—C5—C6	178.10 (18)	K2vi—F6—B2—K2v	−96.95 (5)
C3—C4—C5—C6	−2.5 (3)	K2i—F5—B2—F6	−164.53 (12)
C4—C5—C6—C7	−0.4 (3)	K2vi—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)	K2vi—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)	K2vi—F5—B2—C15	−125.86 (12)
K2i—O2—C9—O1	142.3 (4)	K2i—F5—B2—K2vi	−163.8 (2)
K2i—O2—C9—N1	−38.6 (6)	K2i—F5—B2—K2v	−94.39 (17)
C10—O1—C9—O2	10.7 (3)	K2vi—F5—B2—K2v	69.38 (8)
C10—O1—C9—N1	−168.51 (15)	K2v—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)	K2v—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)	K2v—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)	K2v—F4—B2—K2vi	−33.50 (17)
C9—O1—C10—C13	177.7 (2)	K1i—F4—B2—K2vi	−179.74 (6)
C22—N2—C14—C15	168.35 (16)	K1i—F4—B2—K2v	−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—K2vi	−104.92 (19)
K1i—C15—C16—C21	−94.39 (19)	C16—C15—B2—K2vi	76.4 (2)
C14—C15—C16—C17	1.01 (19)	K1i—C15—B2—K2vi	179.51 (13)
B2—C15—C16—C17	179.87 (17)	C14—C15—B2—K2v	112.3 (2)
K1i—C15—C16—C17	86.18 (13)	C16—C15—B2—K2v	−66.3 (3)
C21—C16—C17—C18	−4.0 (3)	K1i—C15—B2—K2v	36.76 (17)
C15—C16—C17—C18	175.51 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H51···F3ix	0.81 (1)	2.14 (1)	2.903 (2)	156 (3)
O5—H51···F1ix	0.81 (1)	2.62 (2)	3.188 (2)	128 (2)
O5—H52···O5x	0.81 (1)	2.41 (1)	3.1968 (16)	164 (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) ; (ii) .