(1,4,7,10,13,16-Hexaoxacyclo­octa­deca­ne)dimethyl­indium(III) trifluoro­methane­sulfonate

Cooper, B.F.T.; Macdonald, C.L.B.

doi:10.1107/S1600536811001899

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Pages m233-m234

doi:10.1107/S1600536811001899

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(1,4,7,10,13,16-Hexaoxacyclooctadecane)dimethylindium(III) trifluoromethanesulfonate

Benjamin F. T. Cooper ^a and Charles L. B. Macdonald ^a ^*

^aDepartment of Chemistry and Biochemistry, University of Windsor, Windsor, Ontario, Canada N9B 3P4
^*Correspondence e-mail: cmacd@uwindsor.ca

(Received 9 December 2010; accepted 12 January 2011; online 22 January 2011)

In the title compound, [In(CH₃)₂(C₁₂H₂₄O₆)](CF₃O₃S), two of the In—O distances within the cation are significantly shorter than the other four. The In^III atom is in a distorted hexagonal–bipyramidal coordination geometry in which the C—In—C angle is 175.44 (12)°. The crystal structure is stabilized by weak intermolecular 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_r = 558.27
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.037
wR(F²) = 0.077
S = 1.02
5073 reflections
264 parameters
H-atom parameters constrained
Δρ_max = 0.72 e Å⁻³
Δρ_min = −0.34 e Å⁻³

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⋯O23^iv	0.99	2.53	3.322 (4)	137
Symmetry codes: (i) -x+1, -y+1, -z; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) -x+2, -y, -z+1; (iv) -x+2, -y+1, -z+1.

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 ).

Supporting information

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

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

checkCIF report

Comment top

In contrast to the mixed-valent compounds obtained through the reaction of the crown ether adduct of indium(I) trifluoromethanesulfonate, [In([18]crown-6)][OTf], with indium trihalides (Cooper et al., in press), the treatment of [In([18]crown-6)][OTf] with trimethylindium results in the formation of the organometallic salt [InMe₂([18]crown-6)][OTf] (1), as the only isolable crystalline product.

The asymmetric unit of the title compound (1) is shown in Fig. 1. The In–C distances in the cation in 1 of 2.094 (3) and 2.098 (3) Å are somewhat shorter thant the mean distance of 2.151 Å for InMe₂ fragments coordinated by at least two oxygen atoms that have been reported in the Cambridge Structural Database (as determined from the total of 38 examples that are found in CSD Version 5.31) (Allen, 2002). Furthermore, the nearly linear C–In–C fragment in the cation, although anticipated because of the geometry of the crown ether ligand and observed in "base-free" salt [InMe₂][Br] (Hausen et al., 1975), is a very unusual arrangement for coordinated InMe₂ moieties: the largest angle reported in the CSD sample cited above is 159.6 (2)° for a dimeric structure featuring a β-diketonate ligand (Xu et al., 2000). Overall, the coordination geometry of the indium center in 1 is best-described as being a slightly-distorted hexagonal bipyramid in which the metal atom is appreciably closer to two of the oxygen atoms in the ligand. As such, the geometry is reminscent of those exhibited by the products derived from the oxidative addition of chloro-alkanes to benzannelated derivatives of [In([18]crown-6)][OTf] (Cooper et al., 2007).

The indistinguishable S–O distances within each of the trifluoromethanesulfonate anions are consistent with the completely delocalized structure expected for an unperturbed "ionic" trifluoromethanesulfonate anion. In the crystal structure there are weak C—H···O≐S hydrogen bonds (see Table 2) which link the anions and the cations. In addition, there are further weak intermolecular C—H···O hydrogen bonds between symmetry related crown ether ligands (Fig. 2)

Related literature top

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 For related literature, see: Allen (2002).

Experimental top

The salt [InMe₂(18-crown-6)][OTf] was obtained in high yield from the reaction of trimethylindium with the crown ether adduct of indium(I) trifluoromethanesulfonate that was prepared as described previously (Andrews & Macdonald, 2005; Cooper & Macdonald, 2010). Suitable crystals were obtained by the slow evaporation of a dichloromethane solution of the salt in a nitrogen-filled glove box.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 (Sheldrick, 2008), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Thermal ellipsoid plot (30% probability surface) of the contents of the asymmetric unit of [InMe₂([18]crown-6)][O₃SCF₃] (1).
	Fig. 2. Partial packing diagram of [InMe₂([18]crown-6)][O₃SCF₃] (1) illustrating the intramolecular H-bonding interactions. The InMe₂ fragments are removed for clarity.

(1,4,7,10,13,16-Hexaoxacyclooctadecane)dimethylindium(III) trifluoromethanesulfonate top

Crystal data top

[In(CH₃)₂(C₁₂H₂₄O₆)](CF₃O₃S)	F(000) = 1136
M_r = 558.27	D_x = 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

Data collection top

Bruker APEX diffractometer	5073 independent reflections
Radiation source: fine-focus sealed tube	3744 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
ϕ and ω scans	θ_max = 27.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −16→16
T_min = 0.793, T_max = 0.888	k = −16→16
24322 measured reflections	l = −19→19

Refinement top

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(F_o²) + (0.0344P)² + 0.2258P] where P = (F_o² + 2F_c²)/3
5073 reflections	(Δ/σ)_max = 0.001
264 parameters	Δρ_max = 0.72 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

[In(CH₃)₂(C₁₂H₂₄O₆)](CF₃O₃S)	V = 2231.8 (6) Å³
M_r = 558.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.9580 (19) Å	µ = 1.22 mm⁻¹
b = 12.7242 (19) Å	T = 173 K
c = 14.683 (2) Å	0.20 × 0.10 × 0.10 mm
β = 112.801 (2)°

Data collection top

Bruker APEX diffractometer	5073 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	3744 reflections with I > 2σ(I)
T_min = 0.793, T_max = 0.888	R_int = 0.050
24322 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.077	H-atom parameters constrained
S = 1.02	Δρ_max = 0.72 e Å⁻³
5073 reflections	Δρ_min = −0.34 e Å⁻³
264 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O23^iv	0.99	2.53	3.322 (4)	137

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

Experimental details

Crystal data
Chemical formula	[In(CH₃)₂(C₁₂H₂₄O₆)](CF₃O₃S)
M_r	558.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	12.9580 (19), 12.7242 (19), 14.683 (2)
β (°)	112.801 (2)
V (Å³)	2231.8 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.22
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Bruker APEX diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.793, 0.888
No. of measured, independent and observed [I > 2σ(I)] reflections	24322, 5073, 3744
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.077, 1.02
No. of reflections	5073
No. of parameters	264
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.72, −0.34

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).

Selected bond lengths (Å) top

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

Hydrogen-bond geometry (Å, º) top

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···O23^iv	0.99	2.53	3.322 (4)	137

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

Acknowledgements

The funding that has enabled this work has been provided by the Natural Sciences and Engineering Research Council (Canada), the Canada Foundation for Innovation and the Ontario Ministry of Research and Innovation.

References

Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Volume 67| Part 2| February 2011| Pages m233-m234

doi:10.1107/S1600536811001899

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

(1,4,7,10,13,16-Hexaoxa­cyclo­octa­deca­ne)di­methyl­indium(III) tri­fluoro­methane­sulfonate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

(1,4,7,10,13,16-Hexaoxacyclooctadecane)dimethylindium(III) trifluoromethanesulfonate