(1,4,7,10,13,16-Hexaoxacyclo-octa-deca-ne)dimethyl-indium(III) trifluoro-methane-sulfonate.

In the title compound, [In(CH(3))(2)(C(12)H(24)O(6))](CF(3)O(3)S), two of the In-O distances within the cation are significantly shorter than the other four. The In(III) atom is in a distorted hexa-gonal-bipyramidal coordination geometry in which the C-In-C angle is 175.44 (12)°. The crystal structure is stabilized by weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

For the preparation of [In][OTf], where OTf = trifluoro­methane­sulfonate, see: Macdonald et al. (2004 ▶); Cooper & Macdonald (2010 ▶). For the preparation of the crowned complex [In([18]crown-6][OTf], see: Andrews & Macdonald (2005 ▶). For the oxidative addition of [In([18]crown-6][OTf] into aliphatic C—Cl bonds, see: Cooper et al. (2007 ▶). For the reaction of [In][OTf] with indium trihalides, see: Cooper et al. (2011 ▶). For the structure of the related ‘base-free’ salt [InMe2][Br], see: Hausen et al. (1975 ▶). For the structure of a related (β-diketonate)InMe2 complex, see: Xu et al. (2000 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

[In(CH3)2(C12H24O6)](CF3O3S)

M = 558.27

Monoclinic,

a = 12.9580 (19) Å

b = 12.7242 (19) Å

c = 14.683 (2) Å

β = 112.801 (2)°

V = 2231.8 (6) Å3

Z = 4

Mo Kα radiation

μ = 1.22 mm−1

T = 173 K

0.20 × 0.10 × 0.10 mm

Data collection

Bruker APEX diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.793, T max = 0.888

24322 measured reflections

5073 independent reflections

3744 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.077

S = 1.02

5073 reflections

264 parameters

H-atom parameters constrained

Δρmax = 0.72 e Å−3

Δρmin = −0.34 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009 ▶) and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811001899/lh5188sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811001899/lh5188Isup2.hkl

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

[In(CH3)2(C12H24O6)](CF3O3S)	F(000) = 1136
Mr = 558.27	Dx = 1.662 Mg m−3
Monoclinic, P21/c	Melting point: 428 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 12.9580 (19) Å	Cell parameters from 7679 reflections
b = 12.7242 (19) Å	θ = 2.2–28.0°
c = 14.683 (2) Å	µ = 1.22 mm−1
β = 112.801 (2)°	T = 173 K
V = 2231.8 (6) Å3	Prism, colourless
Z = 4	0.20 × 0.10 × 0.10 mm

Bruker APEX diffractometer	5073 independent reflections
Radiation source: fine-focus sealed tube	3744 reflections with I > 2σ(I)
graphite	Rint = 0.050
φ and ω scans	θmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −16→16
Tmin = 0.793, Tmax = 0.888	k = −16→16
24322 measured reflections	l = −19→19

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0344P)2 + 0.2258P] where P = (Fo2 + 2Fc2)/3
5073 reflections	(Δ/σ)max = 0.001
264 parameters	Δρmax = 0.72 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

Experimental. The data crystal was coated in mineral oil and placed rapidly in the cold nitrogen stream of the Kryoflex low-temperature device.Spectroscopic and physical data: dp 155 °C 1H NMR (C6D6): δ= 3.057 (s; CH2, 24H), δ= -0.021 (s, CH3, 6H) 13C NMR (C6D6): δ= 70.00 (s; CH2), -2.491 (s, CH3) 19F NMR (C6D6):δ= 78.12

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
In	0.788938 (19)	0.230045 (18)	0.358803 (16)	0.03526 (8)
C1	0.8733 (2)	0.1496 (2)	0.2835 (2)	0.0330 (7)
H1A	0.9488	0.1787	0.3024	0.050*
H1B	0.8321	0.1576	0.2122	0.050*
H1C	0.8784	0.0749	0.3009	0.050*
C2	0.7168 (3)	0.3162 (3)	0.4405 (2)	0.0431 (8)
H2A	0.7662	0.3142	0.5106	0.065*
H2B	0.6441	0.2856	0.4315	0.065*
H2C	0.7064	0.3893	0.4176	0.065*
C11	0.7141 (3)	0.4506 (2)	0.2018 (2)	0.0456 (9)
H11A	0.7277	0.5074	0.1617	0.055*
H11B	0.6758	0.4811	0.2423	0.055*
C12	0.6440 (3)	0.3674 (3)	0.1367 (2)	0.0422 (8)
H12A	0.5725	0.3975	0.0903	0.051*
H12B	0.6834	0.3353	0.0977	0.051*
C13	0.5558 (3)	0.2066 (3)	0.1395 (2)	0.0492 (9)
H13A	0.5993	0.1649	0.1097	0.059*
H13B	0.4892	0.2356	0.0855	0.059*
C14	0.5210 (3)	0.1392 (3)	0.2044 (3)	0.0485 (9)
H14A	0.4782	0.1811	0.2347	0.058*
H14B	0.4725	0.0816	0.1656	0.058*
C15	0.5917 (3)	0.0237 (3)	0.3400 (2)	0.0455 (8)
H15A	0.5402	−0.0306	0.2983	0.055*
H15B	0.5540	0.0603	0.3781	0.055*
C16	0.6968 (3)	−0.0260 (3)	0.4084 (2)	0.0464 (9)
H16A	0.6801	−0.0780	0.4510	0.056*
H16B	0.7345	−0.0628	0.3704	0.056*
C17	0.8681 (3)	0.0124 (2)	0.5378 (2)	0.0396 (8)
H17A	0.9091	−0.0263	0.5038	0.048*
H17B	0.8511	−0.0371	0.5821	0.048*
C18	0.9371 (3)	0.1009 (2)	0.5957 (2)	0.0395 (8)
H18A	0.8946	0.1419	0.6269	0.047*
H18B	1.0061	0.0738	0.6485	0.047*
C19	1.0489 (3)	0.2400 (2)	0.5817 (2)	0.0397 (8)
H19A	1.1161	0.2036	0.6284	0.048*
H19B	1.0207	0.2883	0.6197	0.048*
C110	1.0775 (3)	0.3001 (3)	0.5072 (2)	0.0427 (8)
H11C	1.1408	0.3484	0.5410	0.051*
H11D	1.0999	0.2512	0.4657	0.051*
C111	1.0032 (3)	0.4257 (3)	0.3795 (2)	0.0477 (9)
H11E	1.0296	0.3843	0.3357	0.057*
H11F	1.0616	0.4777	0.4155	0.057*
C112	0.8974 (3)	0.4799 (2)	0.3207 (2)	0.0490 (9)
H11G	0.8686	0.5175	0.3651	0.059*
H11H	0.9104	0.5320	0.2762	0.059*
O1	0.81800 (17)	0.40389 (15)	0.26423 (15)	0.0354 (5)
O2	0.62296 (17)	0.28979 (16)	0.19748 (15)	0.0373 (5)
O3	0.61913 (16)	0.09713 (16)	0.27933 (15)	0.0363 (5)
O4	0.76689 (16)	0.05488 (15)	0.46713 (14)	0.0347 (5)
O5	0.96498 (16)	0.16552 (15)	0.52962 (13)	0.0323 (5)
O6	0.98188 (17)	0.35800 (16)	0.44774 (15)	0.0387 (5)
O21	0.80907 (19)	0.71444 (18)	0.16120 (17)	0.0495 (6)
O22	0.6098 (2)	0.68156 (18)	0.08395 (16)	0.0535 (6)
O23	0.6906 (2)	0.7465 (2)	0.25086 (18)	0.0654 (8)
F1	0.57677 (19)	0.90759 (17)	0.1002 (2)	0.0820 (8)
F2	0.75310 (19)	0.93621 (17)	0.17324 (19)	0.0772 (7)
F3	0.68476 (18)	0.88076 (16)	0.02420 (17)	0.0666 (6)
S	0.69897 (7)	0.73809 (6)	0.15687 (5)	0.03685 (19)
C	0.6768 (3)	0.8726 (3)	0.1110 (3)	0.0494 (9)

	U11	U22	U33	U12	U13	U23
In	0.03894 (14)	0.03720 (13)	0.03436 (13)	0.00538 (11)	0.01936 (10)	−0.00321 (10)
C1	0.0324 (17)	0.0337 (17)	0.0331 (16)	0.0000 (13)	0.0129 (14)	−0.0078 (13)
C2	0.053 (2)	0.0439 (19)	0.0409 (18)	0.0110 (17)	0.0272 (17)	0.0003 (15)
C11	0.060 (2)	0.0338 (19)	0.052 (2)	0.0159 (17)	0.0313 (19)	0.0140 (16)
C12	0.043 (2)	0.048 (2)	0.0364 (18)	0.0160 (16)	0.0161 (16)	0.0163 (15)
C13	0.040 (2)	0.056 (2)	0.0371 (18)	−0.0015 (17)	−0.0018 (15)	0.0043 (16)
C14	0.0288 (18)	0.054 (2)	0.053 (2)	−0.0025 (16)	0.0057 (16)	0.0021 (17)
C15	0.044 (2)	0.048 (2)	0.047 (2)	−0.0175 (17)	0.0200 (17)	−0.0018 (16)
C16	0.064 (2)	0.0342 (19)	0.044 (2)	−0.0112 (17)	0.0240 (18)	0.0032 (15)
C17	0.0420 (19)	0.0366 (18)	0.0448 (19)	0.0124 (15)	0.0219 (16)	0.0134 (15)
C18	0.0403 (19)	0.050 (2)	0.0293 (17)	0.0094 (15)	0.0143 (15)	0.0098 (14)
C19	0.0355 (17)	0.049 (2)	0.0287 (16)	−0.0009 (15)	0.0060 (14)	−0.0126 (14)
C110	0.0354 (18)	0.046 (2)	0.0451 (19)	−0.0086 (15)	0.0136 (16)	−0.0186 (15)
C111	0.060 (2)	0.044 (2)	0.043 (2)	−0.0247 (18)	0.0241 (18)	−0.0130 (16)
C112	0.079 (3)	0.0262 (18)	0.048 (2)	−0.0132 (18)	0.031 (2)	−0.0051 (15)
O1	0.0453 (13)	0.0246 (11)	0.0404 (12)	0.0016 (9)	0.0211 (11)	0.0002 (9)
O2	0.0350 (12)	0.0428 (14)	0.0315 (11)	0.0043 (10)	0.0101 (9)	0.0071 (9)
O3	0.0275 (11)	0.0436 (13)	0.0363 (12)	−0.0050 (9)	0.0108 (9)	0.0028 (10)
O4	0.0363 (12)	0.0298 (12)	0.0376 (12)	0.0005 (9)	0.0140 (10)	0.0028 (9)
O5	0.0344 (11)	0.0375 (12)	0.0233 (10)	−0.0001 (9)	0.0093 (9)	−0.0013 (9)
O6	0.0425 (13)	0.0362 (12)	0.0413 (13)	−0.0055 (10)	0.0204 (11)	−0.0040 (10)
O21	0.0496 (15)	0.0500 (15)	0.0544 (15)	0.0134 (12)	0.0260 (12)	0.0138 (12)
O22	0.0612 (16)	0.0355 (13)	0.0443 (14)	−0.0113 (12)	−0.0010 (12)	0.0012 (11)
O23	0.0481 (15)	0.113 (2)	0.0387 (14)	−0.0225 (14)	0.0207 (12)	−0.0071 (14)
F1	0.0524 (14)	0.0537 (14)	0.133 (2)	0.0146 (11)	0.0279 (15)	−0.0114 (14)
F2	0.0667 (15)	0.0492 (14)	0.1039 (19)	−0.0221 (12)	0.0202 (14)	−0.0338 (13)
F3	0.0696 (15)	0.0532 (14)	0.0690 (15)	−0.0031 (11)	0.0181 (12)	0.0226 (11)
S	0.0349 (4)	0.0409 (5)	0.0307 (4)	−0.0038 (3)	0.0082 (3)	0.0001 (3)
C	0.041 (2)	0.037 (2)	0.065 (2)	−0.0057 (16)	0.0147 (18)	−0.0129 (18)

In—C2	2.094 (3)	C16—O4	1.422 (4)
In—C1	2.098 (3)	C16—H16A	0.9900
In—O1	2.7145 (19)	C16—H16B	0.9900
In—O2	2.620 (2)	C17—O4	1.426 (3)
In—O3	2.660 (2)	C17—C18	1.485 (4)
In—O4	2.816 (2)	C17—H17A	0.9900
In—O5	2.7810 (19)	C17—H17B	0.9900
In—O6	2.842 (2)	C18—O5	1.421 (3)
C1—H1A	0.9800	C18—H18A	0.9900
C1—H1B	0.9800	C18—H18B	0.9900
C1—H1C	0.9800	C19—O5	1.421 (3)
C2—H2A	0.9800	C19—C110	1.495 (4)
C2—H2B	0.9800	C19—H19A	0.9900
C2—H2C	0.9800	C19—H19B	0.9900
C11—O1	1.431 (4)	C110—O6	1.415 (4)
C11—C12	1.479 (5)	C110—H11C	0.9900
C11—H11A	0.9900	C110—H11D	0.9900
C11—H11B	0.9900	C111—O6	1.427 (4)
C12—O2	1.426 (3)	C111—C112	1.478 (5)
C12—H12A	0.9900	C111—H11E	0.9900
C12—H12B	0.9900	C111—H11F	0.9900
C13—O2	1.424 (4)	C112—O1	1.421 (4)
C13—C14	1.477 (5)	C112—H11G	0.9900
C13—H13A	0.9900	C112—H11H	0.9900
C13—H13B	0.9900	O21—S	1.435 (2)
C14—O3	1.424 (4)	O22—S	1.428 (2)
C14—H14A	0.9900	O23—S	1.429 (2)
C14—H14B	0.9900	F1—C	1.320 (4)
C15—O3	1.427 (3)	F2—C	1.329 (4)
C15—C16	1.485 (4)	F3—C	1.322 (4)
C15—H15A	0.9900	S—C	1.821 (4)
C15—H15B	0.9900
C2—In—C1	175.44 (12)	O4—C16—H16A	110.2
C2—In—O2	88.49 (10)	C15—C16—H16A	110.2
C1—In—O2	94.48 (9)	O4—C16—H16B	110.2
C2—In—O3	96.16 (11)	C15—C16—H16B	110.2
C1—In—O3	88.28 (9)	H16A—C16—H16B	108.5
O2—In—O3	62.50 (6)	O4—C17—C18	108.0 (2)
C2—In—O1	92.72 (10)	O4—C17—H17A	110.1
C1—In—O1	85.66 (9)	C18—C17—H17A	110.1
O2—In—O1	61.91 (6)	O4—C17—H17B	110.1
O3—In—O1	123.29 (6)	C18—C17—H17B	110.1
C2—In—O5	91.73 (10)	H17A—C17—H17B	108.4
C1—In—O5	85.31 (9)	O5—C18—C17	107.7 (2)
O2—In—O5	179.69 (6)	O5—C18—H18A	110.2
O3—In—O5	117.26 (6)	C17—C18—H18A	110.2
O1—In—O5	118.30 (6)	O5—C18—H18B	110.2
C2—In—O4	85.73 (10)	C17—C18—H18B	110.2
C1—In—O4	95.67 (9)	H18A—C18—H18B	108.5
O2—In—O4	120.85 (6)	O5—C19—C110	107.6 (2)
O3—In—O4	59.79 (6)	O5—C19—H19A	110.2
O1—In—O4	176.74 (6)	C110—C19—H19A	110.2
O5—In—O4	58.96 (6)	O5—C19—H19B	110.2
C2—In—O6	86.86 (11)	C110—C19—H19B	110.2
C1—In—O6	88.65 (9)	H19A—C19—H19B	108.5
O2—In—O6	121.12 (6)	O6—C110—C19	108.1 (3)
O3—In—O6	175.45 (6)	O6—C110—H11C	110.1
O1—In—O6	59.76 (6)	C19—C110—H11C	110.1
O5—In—O6	59.11 (6)	O6—C110—H11D	110.1
O4—In—O6	117.24 (6)	C19—C110—H11D	110.1
In—C1—H1A	109.5	H11C—C110—H11D	108.4
In—C1—H1B	109.5	O6—C111—C112	107.7 (3)
H1A—C1—H1B	109.5	O6—C111—H11E	110.2
In—C1—H1C	109.5	C112—C111—H11E	110.2
H1A—C1—H1C	109.5	O6—C111—H11F	110.2
H1B—C1—H1C	109.5	C112—C111—H11F	110.2
In—C2—H2A	109.5	H11E—C111—H11F	108.5
In—C2—H2B	109.5	O1—C112—C111	108.7 (3)
H2A—C2—H2B	109.5	O1—C112—H11G	109.9
In—C2—H2C	109.5	C111—C112—H11G	109.9
H2A—C2—H2C	109.5	O1—C112—H11H	109.9
H2B—C2—H2C	109.5	C111—C112—H11H	109.9
O1—C11—C12	107.9 (2)	H11G—C112—H11H	108.3
O1—C11—H11A	110.1	C112—O1—C11	112.3 (2)
C12—C11—H11A	110.1	C112—O1—In	117.95 (17)
O1—C11—H11B	110.1	C11—O1—In	112.53 (17)
C12—C11—H11B	110.1	C13—O2—C12	111.2 (2)
H11A—C11—H11B	108.4	C13—O2—In	114.95 (17)
O2—C12—C11	108.0 (2)	C12—O2—In	118.51 (17)
O2—C12—H12A	110.1	C14—O3—C15	111.3 (2)
C11—C12—H12A	110.1	C14—O3—In	116.02 (18)
O2—C12—H12B	110.1	C15—O3—In	120.42 (17)
C11—C12—H12B	110.1	C16—O4—C17	111.0 (2)
H12A—C12—H12B	108.4	C16—O4—In	114.27 (16)
O2—C13—C14	108.3 (3)	C17—O4—In	116.43 (16)
O2—C13—H13A	110.0	C19—O5—C18	111.2 (2)
C14—C13—H13A	110.0	C19—O5—In	118.53 (17)
O2—C13—H13B	110.0	C18—O5—In	116.76 (16)
C14—C13—H13B	110.0	C110—O6—C111	112.7 (2)
H13A—C13—H13B	108.4	C110—O6—In	112.93 (17)
O3—C14—C13	108.2 (3)	C111—O6—In	113.48 (17)
O3—C14—H14A	110.1	O22—S—O21	115.40 (16)
C13—C14—H14A	110.1	O23—S—O21	114.74 (15)
O3—C14—H14B	110.1	O22—S—O23	114.82 (15)
C13—C14—H14B	110.1	O21—S—C	103.03 (15)
H14A—C14—H14B	108.4	O22—S—C	103.32 (15)
O3—C15—C16	108.4 (2)	O23—S—C	103.08 (17)
O3—C15—H15A	110.0	F1—C—F2	108.2 (3)
C16—C15—H15A	110.0	F1—C—F3	107.3 (3)
O3—C15—H15B	110.0	F3—C—F2	107.4 (3)
C16—C15—H15B	110.0	F1—C—S	111.6 (3)
H15A—C15—H15B	108.4	F2—C—S	110.4 (3)
O4—C16—C15	107.7 (3)	F3—C—S	111.7 (2)
O1—C11—C12—O2	62.2 (3)	C18—C17—O4—C16	179.6 (2)
O2—C13—C14—O3	−61.1 (4)	C18—C17—O4—In	46.6 (3)
O3—C15—C16—O4	60.4 (3)	C2—In—O4—C16	118.6 (2)
O4—C17—C18—O5	−63.4 (3)	C1—In—O4—C16	−65.7 (2)
O5—C19—C110—O6	64.9 (3)	O2—In—O4—C16	32.9 (2)
O6—C111—C112—O1	−64.2 (3)	O3—In—O4—C16	18.94 (19)
C111—C112—O1—C11	−177.6 (3)	O1—In—O4—C16	−180 (100)
C111—C112—O1—In	49.0 (3)	O5—In—O4—C16	−146.8 (2)
C12—C11—O1—C112	172.2 (3)	O6—In—O4—C16	−157.14 (19)
C12—C11—O1—In	−51.9 (3)	C2—In—O4—C17	−109.9 (2)
C2—In—O1—C112	68.0 (2)	C1—In—O4—C17	65.8 (2)
C1—In—O1—C112	−107.7 (2)	O2—In—O4—C17	164.43 (18)
O2—In—O1—C112	154.9 (2)	O3—In—O4—C17	150.4 (2)
O3—In—O1—C112	167.2 (2)	O1—In—O4—C17	−48.3 (11)
O5—In—O1—C112	−25.4 (2)	O5—In—O4—C17	−15.28 (18)
O4—In—O1—C112	6.6 (11)	O6—In—O4—C17	−25.6 (2)
O6—In—O1—C112	−16.8 (2)	C110—C19—O5—C18	176.8 (2)
C2—In—O1—C11	−65.2 (2)	C110—C19—O5—In	−43.6 (3)
C1—In—O1—C11	119.0 (2)	C17—C18—O5—C19	−168.3 (2)
O2—In—O1—C11	21.60 (18)	C17—C18—O5—In	51.4 (3)
O3—In—O1—C11	34.0 (2)	C2—In—O5—C19	−73.2 (2)
O5—In—O1—C11	−158.67 (17)	C1—In—O5—C19	103.3 (2)
O4—In—O1—C11	−126.7 (10)	O2—In—O5—C19	151 (11)
O6—In—O1—C11	−150.0 (2)	O3—In—O5—C19	−171.05 (18)
C14—C13—O2—C12	−170.3 (3)	O1—In—O5—C19	20.8 (2)
C14—C13—O2—In	51.6 (3)	O4—In—O5—C19	−157.2 (2)
C11—C12—O2—C13	−179.8 (3)	O6—In—O5—C19	12.09 (17)
C11—C12—O2—In	−43.3 (3)	C2—In—O5—C18	64.1 (2)
C2—In—O2—C13	−118.9 (2)	C1—In—O5—C18	−119.4 (2)
C1—In—O2—C13	64.5 (2)	O2—In—O5—C18	−71 (11)
O3—In—O2—C13	−21.2 (2)	O3—In—O5—C18	−33.72 (19)
O1—In—O2—C13	147.2 (2)	O1—In—O5—C18	158.14 (18)
O5—In—O2—C13	16 (11)	O4—In—O5—C18	−19.85 (18)
O4—In—O2—C13	−34.8 (2)	O6—In—O5—C18	149.4 (2)
O6—In—O2—C13	155.66 (19)	C19—C110—O6—C111	174.8 (2)
C2—In—O2—C12	106.2 (2)	C19—C110—O6—In	−55.0 (3)
C1—In—O2—C12	−70.4 (2)	C112—C111—O6—C110	178.9 (2)
O3—In—O2—C12	−156.1 (2)	C112—C111—O6—In	48.9 (3)
O1—In—O2—C12	12.29 (19)	C2—In—O6—C110	117.1 (2)
O5—In—O2—C12	−119 (11)	C1—In—O6—C110	−62.1 (2)
O4—In—O2—C12	−169.71 (18)	O2—In—O6—C110	−156.56 (17)
O6—In—O2—C12	20.8 (2)	O3—In—O6—C110	−14.6 (8)
C13—C14—O3—C15	−174.9 (3)	O1—In—O6—C110	−147.9 (2)
C13—C14—O3—In	42.4 (3)	O5—In—O6—C110	23.21 (17)
C16—C15—O3—C14	173.5 (3)	O4—In—O6—C110	33.55 (19)
C16—C15—O3—In	−45.7 (3)	C2—In—O6—C111	−113.0 (2)
C2—In—O3—C14	72.7 (2)	C1—In—O6—C111	67.7 (2)
C1—In—O3—C14	−108.3 (2)	O2—In—O6—C111	−26.7 (2)
O2—In—O3—C14	−12.3 (2)	O3—In—O6—C111	115.2 (7)
O1—In—O3—C14	−24.6 (2)	O1—In—O6—C111	−18.03 (19)
O5—In—O3—C14	167.9 (2)	O5—In—O6—C111	153.1 (2)
O4—In—O3—C14	154.1 (2)	O4—In—O6—C111	163.42 (19)
O6—In—O3—C14	−155.8 (7)	O22—S—C—F1	58.2 (3)
C2—In—O3—C15	−66.4 (2)	O23—S—C—F1	−61.6 (3)
C1—In—O3—C15	112.6 (2)	O21—S—C—F1	178.7 (3)
O2—In—O3—C15	−151.5 (2)	O22—S—C—F3	−61.9 (3)
O1—In—O3—C15	−163.7 (2)	O23—S—C—F3	178.2 (2)
O5—In—O3—C15	28.8 (2)	O21—S—C—F3	58.6 (3)
O4—In—O3—C15	15.0 (2)	O22—S—C—F2	178.6 (3)
O6—In—O3—C15	65.1 (8)	O23—S—C—F2	58.7 (3)
C15—C16—O4—C17	177.6 (2)	O21—S—C—F2	−60.9 (3)
C15—C16—O4—In	−48.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13B···O22i	0.99	2.54	3.455 (4)	153
C14—H14A···O23ii	0.99	2.43	3.348 (4)	155
C17—H17A···O5iii	0.99	2.58	3.527 (4)	160
C19—H19A···O23iv	0.99	2.53	3.322 (4)	137

Table 1

Selected bond lengths (Å)

In—C2	2.094 (3)
In—C1	2.098 (3)
In—O1	2.7145 (19)
In—O2	2.620 (2)
In—O3	2.660 (2)
In—O4	2.816 (2)
In—O5	2.7810 (19)
In—O6	2.842 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13B⋯O22i	0.99	2.54	3.455 (4)	153
C14—H14A⋯O23ii	0.99	2.43	3.348 (4)	155
C17—H17A⋯O5iii	0.99	2.58	3.527 (4)	160
C19—H19A⋯O23iv	0.99	2.53	3.322 (4)	137

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .