(μ2-2-Meth­oxy­ethanol-κ3O1:O1,O3)(2-meth­oxy­ethanol-κO1)tris­(μ2-3,4,5,6-tetra­fluoro-o-phenyl­ene-κ2C1:C2)trimercury(II)

Castañeda, R.; Draguta, S.; Yakovenko, A.; Fonari, M.; Timofeeva, T.

doi:10.1107/S1600536814006898

metal-organic compounds

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ISSN: 2056-9890

Volume 70| Part 5| May 2014| Pages m164-m165

doi:10.1107/S1600536814006898

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(μ₂-2-Methoxyethanol-κ³O¹:O¹,O³)(2-methoxyethanol-κO¹)tris(μ₂-3,4,5,6-tetrafluoro-o-phenylene-κ²C¹:C²)trimercury(II)

Raúl Castañeda,^a Sergiu Draguta,^a Andrey Yakovenko,^b Marina Fonari ^a and Tatiana Timofeeva ^a ^*

^aDepartment of Chemistry & Biology, New Mexico Highlands University, Diamond Ave, Las Vegas, NM 87701, USA, and ^bX-ray Science Division, Argonne National Laboratory, 9700 S. Cass Avenue, Bldg 401 MS-16 Argonne, IL 60439, USA
^*Correspondence e-mail: lcastaneda3@live.nmhu.edu

(Received 4 March 2014; accepted 27 March 2014; online 5 April 2014)

In the title compound, [Hg₃(C₆F₄)₃(C₃H₈O₂)₂], two O atoms from one 2-methoxyethanol ligand and one O atom from the second 2-methoxyethanol ligand coordinate three Hg^II atoms [Hg—O = 2.765 (7)–2.890 (8) Å] in the trimeric organomercurial Lewis acid (o-C₆F₄Hg)₃. The hydroxy groups are involved in formation of intra- and intermolecular O—H⋯O hydrogen bonds; the latter link two molecules into centrosymmetric dimers. An extensive net of weak intermolecular C—H⋯F interactions further consolidates the crystal packing.

CCDC reference: 994110

Related literature

For the synthesis of trimeric perfluoro-ortho-phenylene mercury and its use as a catalyst, see: Sartori & Golloch (1968 ) and Lee et al. (1999 ), respectively. For the properties of organomercurial anticrowns, see: Taylor et al. (2007 ). For related crystal structures, see: Tikhonova et al. (2002 , 2013 ).

Experimental

Crystal data

[Hg₃(C₆F₄)₃(C₃H₈O₂)₂]
M_r = 1198.14
Triclinic, $[P \overline 1]$
a = 10.170 (4) Å
b = 12.623 (5) Å
c = 12.962 (5) Å
α = 113.450 (5)°
β = 110.411 (5)°
γ = 92.795 (5)°
V = 1396.3 (9) Å³
Z = 2
Mo Kα radiation
μ = 16.56 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.979, T_max = 0.984
16463 measured reflections
8430 independent reflections
4880 reflections with I > 2σ(I)
R_int = 0.090

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.101
S = 0.91
8430 reflections
386 parameters
H-atom parameters constrained
Δρ_max = 3.70 e Å⁻³
Δρ_min = −2.93 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3	0.84	2.04	2.771 (11)	145
O3—H3⋯O4ⁱ	0.84	1.86	2.694 (10)	171
C21—H21B⋯F6ⁱⁱ	0.99	2.52	3.480 (14)	162
C23—H23A⋯F10ⁱⁱⁱ	0.99	2.48	3.109 (12)	121
C23—H23B⋯F11^iv	0.99	2.47	3.301 (12)	141
C24—H24B⋯F5ⁱⁱ	0.98	2.54	3.339 (14)	138
C24—H24C⋯F2^v	0.98	2.46	3.352 (15)	152
C19—H19B⋯F2^vi	0.98	2.53	3.207 (13)	126
Symmetry codes: (i) -x, -y+1, -z; (ii) x-1, y, z; (iii) x, y-1, z; (iv) -x, -y+2, -z+1; (v) -x, -y+1, -z+1; (vi) x, y, z-1.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2001 ); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 994110

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814006898/cv5445sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814006898/cv5445Isup2.hkl

checkCIF report

Comments top

As an organomercurial compound trimeric perfluoro-o-phenylene mercury (I) has numerous adducts with aldehydes, ketones, amides, nitriles, phosphoramides, and sulfoxides (Taylor et al., 2007). Formation of complexes involving I with oxygenated Lewis bases similar to 2-methoxyethanol (II) had been observed before (Tikhonova et al., 2002). The studies of this type of coordination are important due the effect of I on the keto-enol tautomerism (Tikhonova et al., 2013) as well on the activation of carbonyl compounds (Tikhonova et al., 2002). Acting as Lewis acid I had proven catalyze the Diels-Alder reaction between thionoester and cyclopentadiene (Lee et al., 1999). Besides II is not a strong Lewis base it exhibits shorter Hg···O contacts than the sum of the van der Walls radii (Hg = 1.7-2 Å, O = 1.52 Å).

In the title compound (Fig. 1), the coordinating Hg···O contacts range from 2.765 (7) to 2.890 (8) Å. These short contacts are in the same range as those described for carbonyl compounds (Tikhonova et al., 2002). The present complex [I·(II)₂] has two II molecules per one I molecule. The hydroxy groups are involved in formation of intra- and intermolecular O—H···O hydrogen bonds (Table 1), and the latter ones link two complex molecules into centrosymmetric dimers. An extensive net of weak intermolecular C—H···F interactions (Table 1) consolidate further the crystal packing. To the best of our knowledge this complex is the first coordination example of a non-cyclic ether with macrocycle I. That indicates a possibility of I to form complexes with non-cyclic ethers, like polyethylene glycol derivatives.

Experimental top

Synthesis and crystallization top

Trimeric perfluoro-o-phenylene mercury (I) was synthesized according to the known procedure (Sartori & Golloch, 1968). The title compound [I·(II)₂] was obtained by dissolving pure I in II, followed by slow evaporation of the solvent until single crystals were obtained.

Refinement top

All hydrogen atoms were placed in the calculated positions with O—H = 0.84 Å, C—H = 0.98–0.99 Å and refined as riding, with U_iso(H) = 1.2–1.5 U_eq of the parent atom.

Related literature top

For the synthesis of trimeric perfluoro-ortho-phenylene mercury and its use as a catalyst, see Sartori & Golloch (1968) and Lee et al. (1999), respectively. For the properties of organomercurial anticrowns, see: Taylor et al. (2007). For related crystal structures, see: Tikhonova et al. (2002, 2013).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound showing the atomic numbering and 50% probability displacement ellipsoids. Dashed line denotes hydrogen bond.
	Fig. 2. The crystal packing.

(µ₂-2-Methoxyethanol-κ³O¹:O¹,O³)(2-methoxyethanol-κO¹)tris(µ₂-3,4,5,6-tetrafluoro-o-phenylene-κ²C¹:C²)trimercury(II) top

Crystal data top

[Hg₃(C₆F₄)₃(C₃H₈O₂)₂]	V = 1396.3 (9) Å³
M_r = 1198.14	Z = 2
Triclinic, P1	F(000) = 1080
a = 10.170 (4) Å	D_x = 2.850 Mg m⁻³
b = 12.623 (5) Å	Mo Kα radiation, λ = 0.71073 Å
c = 12.962 (5) Å	µ = 16.56 mm⁻¹
α = 113.450 (5)°	T = 100 K
β = 110.411 (5)°	Prism, colourless
γ = 92.795 (5)°	0.30 × 0.25 × 0.20 mm

Data collection top

Bruker APEXII CCD diffractometer	8430 independent reflections
Radiation source: fine-focus sealed tube	4880 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.090
ϕ and ω scans	θ_max = 30.7°, θ_min = 4.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −14→14
T_min = 0.979, T_max = 0.984	k = −17→18
16463 measured reflections	l = −18→18

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H-atom parameters constrained
S = 0.91	w = 1/[σ²(F_o²) + (0.0194P)²] where P = (F_o² + 2F_c²)/3
8430 reflections	(Δ/σ)_max = 0.001
386 parameters	Δρ_max = 3.70 e Å⁻³
0 restraints	Δρ_min = −2.93 e Å⁻³

Crystal data top

[Hg₃(C₆F₄)₃(C₃H₈O₂)₂]	γ = 92.795 (5)°
M_r = 1198.14	V = 1396.3 (9) Å³
Triclinic, P1	Z = 2
a = 10.170 (4) Å	Mo Kα radiation
b = 12.623 (5) Å	µ = 16.56 mm⁻¹
c = 12.962 (5) Å	T = 100 K
α = 113.450 (5)°	0.30 × 0.25 × 0.20 mm
β = 110.411 (5)°

Data collection top

Bruker APEXII CCD diffractometer	8430 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	4880 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.984	R_int = 0.090
16463 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 0.91	Δρ_max = 3.70 e Å⁻³
8430 reflections	Δρ_min = −2.93 e Å⁻³
386 parameters

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 > 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
Hg1	0.34545 (4)	1.01863 (4)	0.29484 (4)	0.01824 (11)
Hg2	0.22471 (4)	0.98504 (4)	0.51393 (4)	0.01800 (11)
Hg3	0.41210 (4)	0.77523 (4)	0.36850 (4)	0.01824 (11)
F1	0.1682 (7)	0.9075 (6)	0.7026 (6)	0.0307 (16)
F2	0.2340 (9)	0.7301 (7)	0.7630 (7)	0.048 (2)
F3	0.3741 (8)	0.5752 (7)	0.6553 (6)	0.0408 (19)
F4	0.4452 (7)	0.5942 (6)	0.4792 (6)	0.0303 (16)
F5	0.5756 (7)	0.6279 (6)	0.2121 (6)	0.0310 (17)
F6	0.6681 (7)	0.6575 (6)	0.0508 (6)	0.0323 (17)
F7	0.6287 (7)	0.8460 (6)	0.0030 (6)	0.0331 (17)
F8	0.4924 (7)	1.0048 (6)	0.1120 (6)	0.0316 (17)
F9	0.2731 (7)	1.2533 (6)	0.2847 (6)	0.0279 (16)
F10	0.1551 (7)	1.4209 (6)	0.4062 (6)	0.0328 (17)
F11	0.0669 (7)	1.3997 (6)	0.5718 (6)	0.0336 (18)
F12	0.0954 (6)	1.2102 (6)	0.6197 (6)	0.0274 (16)
O1	0.1057 (7)	0.9283 (7)	0.0754 (6)	0.0220 (17)
O2	0.1230 (7)	0.8390 (7)	0.2563 (7)	0.0221 (17)
H2	0.1125	0.7678	0.2434	0.033*
O3	0.1619 (8)	0.6097 (7)	0.1593 (7)	0.0262 (18)
H3	0.1431	0.5953	0.0860	0.039*
O4	−0.1110 (8)	0.4592 (8)	0.0789 (6)	0.0261 (19)
C1	0.2690 (11)	0.8440 (10)	0.5548 (9)	0.020 (2)
C2	0.2353 (11)	0.8292 (11)	0.6427 (10)	0.025 (3)
C3	0.2689 (14)	0.7414 (11)	0.6758 (10)	0.030 (3)
C4	0.3408 (14)	0.6609 (11)	0.6203 (11)	0.030 (3)
C5	0.3735 (12)	0.6747 (11)	0.5329 (11)	0.028 (3)
C6	0.3446 (11)	0.7621 (10)	0.4967 (9)	0.018 (2)
C7	0.4814 (11)	0.8017 (10)	0.2454 (9)	0.019 (2)
C8	0.5518 (11)	0.7228 (11)	0.1895 (11)	0.026 (3)
C9	0.6030 (11)	0.7385 (10)	0.1068 (10)	0.020 (2)
C10	0.5808 (12)	0.8336 (11)	0.0835 (10)	0.025 (3)
C11	0.5103 (11)	0.9119 (10)	0.1372 (11)	0.023 (3)
C12	0.4586 (10)	0.8986 (9)	0.2192 (10)	0.018 (2)
C13	0.2464 (10)	1.1399 (9)	0.3867 (9)	0.016 (2)
C14	0.2302 (11)	1.2401 (10)	0.3691 (9)	0.0193 (17)
C15	0.1701 (11)	1.3265 (10)	0.4274 (9)	0.0193 (17)
C16	0.1251 (12)	1.3143 (11)	0.5125 (10)	0.024 (3)
C17	0.1416 (11)	1.2187 (11)	0.5344 (9)	0.020 (2)
C18	0.1981 (12)	1.1268 (11)	0.4728 (10)	0.024 (3)
C19	0.1318 (14)	0.9019 (13)	−0.0342 (11)	0.036 (3)
H19A	0.0444	0.8993	−0.0996	0.055*
H19B	0.1587	0.8250	−0.0606	0.055*
H19C	0.2100	0.9634	−0.0165	0.055*
C20	0.0035 (11)	0.8364 (10)	0.0569 (10)	0.024 (3)
H20A	0.0308	0.7599	0.0220	0.028*
H20B	−0.0917	0.8328	−0.0025	0.028*
C21	−0.0059 (12)	0.8555 (12)	0.1742 (11)	0.030 (3)
H21A	−0.0190	0.9368	0.2149	0.036*
H21B	−0.0907	0.7993	0.1573	0.036*
C22	0.1456 (12)	0.4994 (11)	0.1684 (11)	0.029 (3)
H22A	0.2294	0.5029	0.2386	0.034*
H22B	0.1416	0.4333	0.0926	0.034*
C23	0.0117 (11)	0.4786 (11)	0.1859 (9)	0.024 (3)
H23A	0.0071	0.4087	0.2025	0.029*
H23B	0.0120	0.5480	0.2576	0.029*
C24	−0.2418 (12)	0.4380 (13)	0.0905 (12)	0.036 (3)
H24A	−0.3226	0.4258	0.0152	0.055*
H24B	−0.2444	0.5063	0.1603	0.055*
H24C	−0.2490	0.3673	0.1040	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Hg1	0.0181 (2)	0.0224 (3)	0.0180 (2)	0.00763 (18)	0.00949 (17)	0.0103 (2)
Hg2	0.0193 (2)	0.0209 (3)	0.0173 (2)	0.00739 (18)	0.00843 (17)	0.01047 (19)
Hg3	0.0176 (2)	0.0230 (3)	0.0186 (2)	0.00700 (18)	0.00915 (17)	0.0115 (2)
F1	0.047 (4)	0.031 (4)	0.024 (4)	0.019 (4)	0.025 (3)	0.012 (3)
F2	0.087 (6)	0.050 (5)	0.037 (5)	0.032 (5)	0.043 (4)	0.031 (4)
F3	0.071 (5)	0.041 (5)	0.037 (4)	0.029 (4)	0.036 (4)	0.029 (4)
F4	0.034 (4)	0.026 (4)	0.035 (4)	0.015 (3)	0.017 (3)	0.014 (3)
F5	0.036 (4)	0.028 (4)	0.046 (5)	0.017 (3)	0.025 (3)	0.024 (4)
F6	0.039 (4)	0.028 (4)	0.053 (5)	0.019 (3)	0.037 (4)	0.022 (4)
F7	0.042 (4)	0.043 (5)	0.042 (4)	0.022 (4)	0.034 (4)	0.030 (4)
F8	0.042 (4)	0.037 (5)	0.036 (4)	0.018 (4)	0.026 (3)	0.026 (4)
F9	0.040 (4)	0.026 (4)	0.026 (4)	0.013 (3)	0.016 (3)	0.016 (3)
F10	0.052 (4)	0.030 (4)	0.032 (4)	0.023 (4)	0.023 (3)	0.021 (4)
F11	0.051 (4)	0.039 (5)	0.029 (4)	0.029 (4)	0.024 (3)	0.023 (4)
F12	0.034 (4)	0.035 (4)	0.025 (4)	0.012 (3)	0.020 (3)	0.017 (3)
O1	0.021 (4)	0.023 (5)	0.017 (4)	0.004 (3)	0.006 (3)	0.005 (4)
O2	0.019 (4)	0.022 (5)	0.023 (4)	0.006 (3)	0.007 (3)	0.009 (4)
O3	0.034 (4)	0.028 (5)	0.018 (4)	0.004 (4)	0.012 (4)	0.011 (4)
O4	0.023 (4)	0.043 (6)	0.016 (4)	0.008 (4)	0.010 (3)	0.015 (4)
C1	0.021 (5)	0.016 (6)	0.014 (6)	−0.001 (5)	0.003 (5)	0.002 (5)
C2	0.021 (6)	0.028 (7)	0.025 (6)	0.007 (5)	0.008 (5)	0.014 (6)
C3	0.057 (8)	0.023 (7)	0.020 (6)	0.016 (6)	0.022 (6)	0.013 (6)
C4	0.054 (8)	0.030 (8)	0.032 (7)	0.020 (7)	0.030 (6)	0.024 (6)
C5	0.029 (6)	0.037 (8)	0.033 (7)	0.019 (6)	0.019 (6)	0.023 (7)
C6	0.022 (5)	0.025 (7)	0.014 (5)	0.010 (5)	0.015 (5)	0.007 (5)
C7	0.022 (6)	0.023 (7)	0.016 (6)	0.006 (5)	0.014 (5)	0.006 (5)
C8	0.021 (6)	0.024 (7)	0.030 (7)	0.000 (5)	0.011 (5)	0.009 (6)
C9	0.018 (5)	0.026 (7)	0.021 (6)	0.010 (5)	0.014 (5)	0.007 (5)
C10	0.026 (6)	0.036 (8)	0.022 (6)	0.007 (5)	0.019 (5)	0.015 (6)
C11	0.024 (6)	0.018 (7)	0.033 (7)	0.004 (5)	0.012 (5)	0.016 (6)
C12	0.010 (5)	0.011 (6)	0.025 (6)	0.000 (4)	0.007 (4)	0.000 (5)
C13	0.017 (5)	0.009 (6)	0.011 (5)	−0.002 (4)	0.002 (4)	−0.001 (4)
C14	0.028 (4)	0.021 (5)	0.014 (4)	0.009 (4)	0.009 (3)	0.011 (4)
C15	0.028 (4)	0.021 (5)	0.014 (4)	0.009 (4)	0.009 (3)	0.011 (4)
C16	0.029 (6)	0.028 (7)	0.018 (6)	0.016 (6)	0.013 (5)	0.008 (5)
C17	0.024 (6)	0.025 (7)	0.004 (5)	0.005 (5)	0.003 (4)	0.001 (5)
C18	0.033 (6)	0.029 (7)	0.023 (6)	0.018 (6)	0.014 (5)	0.019 (6)
C19	0.053 (8)	0.049 (9)	0.022 (7)	0.026 (7)	0.020 (6)	0.023 (7)
C20	0.020 (6)	0.021 (7)	0.020 (6)	0.004 (5)	0.003 (5)	0.003 (5)
C21	0.023 (6)	0.048 (9)	0.033 (7)	0.013 (6)	0.006 (5)	0.034 (7)
C22	0.033 (6)	0.026 (7)	0.025 (7)	0.010 (6)	0.012 (5)	0.008 (6)
C23	0.037 (7)	0.020 (7)	0.007 (5)	0.000 (5)	0.003 (5)	0.004 (5)
C24	0.030 (7)	0.042 (9)	0.043 (8)	0.005 (6)	0.016 (6)	0.024 (7)

Geometric parameters (Å, º) top

Hg1—C13	2.076 (10)	O2—C21	1.457 (12)
Hg1—C12	2.087 (10)	O3—C22	1.450 (14)
Hg1—O1	2.765 (7)	O4—C24	1.415 (13)
Hg1—O2	2.844 (9)	O4—C23	1.427 (12)
Hg2—C18	2.065 (11)	C1—C2	1.374 (15)
Hg2—C1	2.078 (11)	C1—C6	1.446 (14)
Hg2—O2	2.850 (8)	C2—C3	1.357 (15)
Hg3—C6	2.064 (10)	C3—C4	1.395 (15)
Hg3—C7	2.083 (10)	C4—C5	1.356 (15)
Hg3—O3	2.890 (8)	C5—C6	1.368 (15)
F1—C2	1.366 (12)	C7—C8	1.374 (14)
F2—C3	1.352 (13)	C7—C12	1.404 (15)
F3—C4	1.345 (13)	C8—C9	1.418 (15)
F4—C5	1.383 (12)	C9—C10	1.360 (16)
F5—C8	1.355 (13)	C10—C11	1.358 (15)
F6—C9	1.350 (11)	C11—C12	1.399 (15)
F7—C10	1.353 (11)	C13—C14	1.379 (14)
F8—C11	1.341 (12)	C13—C18	1.427 (14)
F9—C14	1.373 (11)	C14—C15	1.366 (14)
F10—C15	1.330 (12)	C15—C16	1.389 (15)
F11—C16	1.350 (12)	C16—C17	1.351 (16)
F12—C17	1.380 (12)	C17—C18	1.400 (14)
O1—C20	1.404 (13)	C20—C21	1.480 (15)
O1—C19	1.447 (12)	C22—C23	1.484 (15)

C13—Hg1—C12	174.4 (4)	C11—C10—F7	121.1 (11)
C18—Hg2—C1	175.0 (4)	C11—C10—C9	121.2 (10)
C6—Hg3—C7	175.8 (4)	F7—C10—C9	117.6 (10)
C20—O1—C19	111.1 (9)	F8—C11—C10	118.9 (10)
C24—O4—C23	112.5 (8)	F8—C11—C12	119.7 (9)
C2—C1—C6	117.7 (10)	C10—C11—C12	121.4 (10)
C2—C1—Hg2	121.4 (8)	C7—C12—C11	118.4 (9)
C6—C1—Hg2	120.8 (8)	C7—C12—Hg1	121.8 (8)
C3—C2—F1	117.8 (10)	C11—C12—Hg1	119.8 (8)
C3—C2—C1	122.9 (11)	C14—C13—C18	117.4 (9)
F1—C2—C1	119.3 (10)	C14—C13—Hg1	120.0 (8)
C2—C3—F2	121.0 (10)	C18—C13—Hg1	122.5 (8)
C2—C3—C4	120.4 (11)	C15—C14—F9	117.1 (9)
F2—C3—C4	118.6 (10)	C15—C14—C13	124.5 (10)
F3—C4—C5	123.8 (10)	F9—C14—C13	118.4 (9)
F3—C4—C3	119.3 (10)	F10—C15—C14	122.3 (10)
C5—C4—C3	116.9 (11)	F10—C15—C16	119.7 (9)
C4—C5—C6	125.6 (11)	C14—C15—C16	118.0 (10)
C4—C5—F4	116.0 (10)	C17—C16—F11	122.0 (10)
C6—C5—F4	118.4 (10)	C17—C16—C15	119.5 (10)
C5—C6—C1	116.5 (10)	F11—C16—C15	118.5 (10)
C5—C6—Hg3	120.4 (8)	C16—C17—F12	117.5 (9)
C1—C6—Hg3	123.1 (8)	C16—C17—C18	123.7 (10)
C8—C7—C12	119.4 (10)	F12—C17—C18	118.7 (10)
C8—C7—Hg3	119.1 (9)	C17—C18—C13	116.9 (10)
C12—C7—Hg3	121.5 (7)	C17—C18—Hg2	121.6 (8)
F5—C8—C7	121.3 (10)	C13—C18—Hg2	121.3 (8)
F5—C8—C9	117.7 (10)	O1—C20—C21	110.6 (10)
C7—C8—C9	121.0 (11)	O2—C21—C20	111.5 (9)
F6—C9—C10	122.0 (10)	O3—C22—C23	109.9 (9)
F6—C9—C8	119.4 (10)	O4—C23—C22	110.2 (8)
C10—C9—C8	118.6 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3	0.84	2.04	2.771 (11)	145
O3—H3···O4ⁱ	0.84	1.86	2.694 (10)	171
C21—H21B···F6ⁱⁱ	0.99	2.52	3.480 (14)	162
C23—H23A···F10ⁱⁱⁱ	0.99	2.48	3.109 (12)	121
C23—H23B···F11^iv	0.99	2.47	3.301 (12)	141
C24—H24B···F5ⁱⁱ	0.98	2.54	3.339 (14)	138
C24—H24C···F2^v	0.98	2.46	3.352 (15)	152
C19—H19B···F2^vi	0.98	2.53	3.207 (13)	126

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3	0.84	2.04	2.771 (11)	144.6
O3—H3···O4ⁱ	0.84	1.86	2.694 (10)	170.8
C21—H21B···F6ⁱⁱ	0.99	2.52	3.480 (14)	162.2
C23—H23A···F10ⁱⁱⁱ	0.99	2.48	3.109 (12)	121.2
C23—H23B···F11^iv	0.99	2.47	3.301 (12)	141.3
C24—H24B···F5ⁱⁱ	0.98	2.54	3.339 (14)	138.2
C24—H24C···F2^v	0.98	2.46	3.352 (15)	152.0
C19—H19B···F2^vi	0.98	2.53	3.207 (13)	126.4

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

Acknowledgements

The authors are grateful for NSF support via DMR-0934212 (PREM).

References

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Volume 70| Part 5| May 2014| Pages m164-m165

doi:10.1107/S1600536814006898

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