Potassium bis(4,5-dimercapto-1,3-di­thiole-2-thionato)­nickelate 1,4,7,10,13,16-hexaoxa-2,3:11,12-dibenzocyclo­octadeca-2,11-diene propanone solvate

In the title compound, K[Ni(C₃S₅)₂]·C₂₀H₂₄O₆·C₃H₆O, K⁺ is incorporated in the cavity of the 1,4,7,10,13,16-hexaoxa­-2,3:11,12-dibenzocyclo­octadeca-2,11-diene (DB18c6) mol­ecule and is coordinated by the six DB18c6 O atoms and the propanone O atom. Two {K⁺(DB18c6)[(CH₃)₂CO]} units form a dimer which is aligned in a one-dimensional manner along the a axis through a face-to-face interaction between the benzene rings of neighboring DB18c6 mol­ecules. [Ni(dmit)₂]⁻ anions are also aligned along the a axis through side-by-side S...S interactions.

S1. Comment

[Ni(dmit)₂]^- is a planar π-conjugated anion and has an open-shell electronic structure with S = 1/2 spin. [Ni(dmit)₂]^- salts with various counter-cations have been reported and some possess interesting magnetic properties, such as spin-ladder properties (Imai et al., 1999). Counter-cations for [Ni(dmit)₂]^- salts are necessary to neutralize the total charge in the crystal and affect the whole crystal structure. We have introduced supramolecular cation (SC⁺) structures composed of metal cations and crown ethers as the counter-cation for [Ni(dmit)₂]^- in order to control the spin arrangements of [Ni(dmit)₂]^-. In the crystal, SC⁺ showed a variety of structures, such as the typical disc-shaped structure, in which K⁺ is completely included at the center of the crown-ether cavity, and the sandwich-type Ca²⁺(15-crown-5)₂, in which Ca²⁺ is located at the midpoint between two crown ether molecules (Takamatsu et al., 2000; Akutagawa et al., 2001).

2,3:11,12-Dibenzo-1,4,7,10,13,16-hexaoxocyclooctadeca-2,11-diene (DB18c6) is a typical crown ether having two phenyl rings. A novel SC⁺ assembly through π–π interaction is expected within the [Ni(dmit)₂]^- crystal using DB18c6 as a building block for the SC⁺ structure. In the present study, we report the crystal structure of K[Ni(dmit)₂](DB18c6)·(CH₃)₂CO, (I), in which DB18c6 forms a one-dimensional array through π–π interactions of the dibenzo moieties.

Fig. 1 represents an ORTEPIII (Burnett & Johnson, 1996) view of salt (I). The six O atoms of the DB18c6 unit are coplanar, as reported in literature (Bright & Truter, 1970), and K⁺ is incorporated at the center of the DB18c6 cavity. The six K—O distances are in the range 2.691 (3)–2.794 (3) Å. In addition, the propanone O atom is coordinated to K⁺ with a K—O distance of 2.611 (4) %A. The DB18c6 molecule has a V-shaped conformation, with a dihedral angle of 100.46° between the two benzene rings. One propanone molecule is enclosed by the V-shaped DB18c6 molecule and is fixed by a short K—O coordination.

The [Ni(dmit)₂]^- complex anion is planar in the crystal, as is usually reported (Pullen & Olk, 1999). The maximum deviation from the least-squares plane of [Ni(dmit)₂]^- is 0.105 Å for S7. Within the crystal, [Ni(dmit)₂]^- anions are arranged along the a axis and the direction of the molecular long axis alternately turns toward [012] and [012], as shown in Fig. 2. The angles between the long axes of adjacent [Ni(dmit)₂]^- anions are 57.26 and 57.48°. Short S···S contact distances observed in the side-by-side S···S interactions between neighboring molecules are nearly equal to or less than the van der Waals S···S contact distance of 3.60 Å (Bondi, 1964). S···S contacts less than 3.70 Å are summarized in Table 1. The side-by-side S···S contacts arrange the [Ni(dmit)₂]^- anions in a one-dimensional manner.

As shown in Fig. 3, SC⁺ is aligned along the a axis, forming a one-dimensional structure. Two {K⁺(DB18c6)[(CH₃)₂CO]} units form a dimer related by C₂ symmetry, which is a repeating unit. In the dimer, the molecular planes of the propanone molecule are parallel and the directions of the C═O bonds are opposite to each other. Intermolecular distances between carbonyl groups are 3.276 (9) (C27···C27) and 3.385 (6) Å (C27···O7), and these distances are close to the van der Waals C···O contact distance of 3.22 Å (Bondi, 1964). Since the propanone molecule has a strong dipole moment (2.88 D), dipole–dipole interactions between the carbonyl groups can contribute to the formation of the dimer structure.

The benzene rings of neighboring DB18c6 molecules have a face-to-face orientation and the mean interplanar distance between them is 3.421 Å, which is nearly equal to the van der Waals contacts of aromatic hydrocarbons, ca 3.4 Å. Selected intermolecular distances less than 3.6 Å between two benzene rings are summarized in Table 1. A one-dimensional supramolecular array of (pyridinium)⁺(DB18c6)BF₄^- has been reported in which pyridinium and the V-shaped DB18c6 molecule stack alternately to form a one-dimensional column by utilizing intermolecular face-to-face π–π interactions and hydrogen bonding between the host and guest molecules (Lämsä et al., 1998; Talanova et al., 1999). In the present case, intermolecular π–π interactions between the benzene rings of host molecules form a one-dimensional [K⁺(DB18c6)(CH₃)₂CO]₂ dimer array.

Related literature

For related literature, see: Akutagawa et al. (2001); Bondi (1964); Bright & Truter (1970); Burnett & Johnson (1996); Imai et al. (1999); Lämsä et al. (1998); Pullen & Olk (1999); Takamatsu et al. (2000); Talanova et al. (1999).

S2. Experimental

The title crystal was prepared by slow evaporation of an propanone solution of (ⁿBu₄N)[Ni(dmit)₂], DB18c6 and KClO₄. Shiny black plate-like crystals were obtained.

S3. Refinement

The molecule of (I) crystallized in the monoclinic system; space group C2/c was assumed from the systematic absences. The propanone methyl groups undergo motion or are slightly disordered. [Please provide some information on how the H atoms were treated in the refinement, including the range of constrained C—H distances]

Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: TEXSAN (Molecular Structure Corporation and Rigaku, 1999); molecular graphics: ORTEPIII (Burnett & Johnson, 1996).

Figures

	Fig. 1. The molecular structure of (I), with displacement ellipsoids at the 50% probablity level and H atoms omitted for clarify.
	Fig. 2. Packing diagram of (I) viewed along the a axis. The directions of [Ni(dmit)2]^- are almost [012] and [012].
	Fig. 3. SC^+ arrangements viewed along the b axis. The dimer is aligned along the a axis.

Potassium bis(4,5-dimercapto-1,3-dithiole-2-thionato)nickelate 2,3:11,12-dibenzo-1,4,7,10,13,16-hexaoxocyclooctadeca-2,11-diene propanone solvate

Crystal data

K[Ni(C3S5)2](C20H24O6)·C3H6O	F(000) = 3736.00
Mr = 908.95	Dx = 1.575 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.7107 Å
a = 12.8232 (5) Å	Cell parameters from 18032 reflections
b = 22.4666 (8) Å	θ = 2.4–27.5°
c = 26.612 (1) Å	µ = 1.20 mm^−1
β = 90.201 (2)°	T = 296 K
V = 7666.6 (5) Å^3	Plate, black
Z = 8	0.35 × 0.35 × 0.10 mm

Data collection

Rigaku RAXIS-RAPID Imaging Plate diffractometer	8776 independent reflections
Radiation source: X-ray tube	4422 reflections with F^2 > 2σ(F^2)
Graphite monochromator	Rint = 0.050
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = 0→16
Tmin = 0.699, Tmax = 0.887	k = 0→29
36400 measured reflections	l = −34→34

Refinement

Refinement on F^2	H-atom parameters not refined
R[F^2 > 2σ(F^2)] = 0.035	w = 1/[σ^2(Fo^2) + {0.05[Max(Fo^2,0) + 2Fc^2]/3}^2]
wR(F^2) = 0.088	(Δ/σ)max = 0.0004
S = 1.05	Δρmax = 0.32 e Å^−3
4422 reflections	Δρmin = −0.24 e Å^−3
433 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Ni1	0.20907 (4)	0.34532 (2)	0.30741 (2)	0.0481 (1)
K1	0.23407 (7)	0.07948 (4)	0.37070 (4)	0.0558 (3)
S1	0.2017 (1)	0.41861 (6)	0.47451 (4)	0.0739 (4)
S2	0.0396 (1)	0.42245 (8)	0.55355 (5)	0.0955 (5)
S3	0.00084 (9)	0.36739 (6)	0.45358 (5)	0.0716 (4)
S4	0.06295 (8)	0.33406 (6)	0.34707 (4)	0.0620 (4)
S5	0.28303 (9)	0.38915 (6)	0.37053 (4)	0.0617 (4)
S6	0.42061 (8)	0.31821 (5)	0.16269 (4)	0.0590 (3)
S7	0.3850 (1)	0.25845 (7)	0.06486 (5)	0.0866 (5)
S8	0.21953 (9)	0.26528 (5)	0.14243 (4)	0.0605 (4)
S9	0.13743 (8)	0.29895 (5)	0.24532 (4)	0.0566 (3)
S10	0.35396 (8)	0.35776 (5)	0.26713 (4)	0.0533 (3)
O1	0.3536 (2)	0.0214 (1)	0.3022 (1)	0.0518 (8)
O2	0.3555 (2)	0.1353 (1)	0.3032 (1)	0.0553 (9)
O3	0.2535 (2)	0.1985 (1)	0.3796 (1)	0.0606 (9)
O4	0.1119 (2)	0.1392 (1)	0.4413 (1)	0.0589 (9)
O5	0.0946 (2)	0.0251 (1)	0.4331 (1)	0.0563 (9)
O6	0.2301 (2)	−0.0414 (1)	0.3700 (1)	0.0554 (9)
O7	0.0654 (3)	0.0767 (2)	0.3155 (1)	0.098 (1)
C1	0.3647 (3)	0.0478 (2)	0.2560 (2)	0.048 (1)
C2	0.3651 (3)	0.1098 (2)	0.2565 (2)	0.051 (1)
C3	0.3585 (3)	0.1984 (2)	0.3069 (2)	0.063 (1)
C4	0.3543 (3)	0.2146 (2)	0.3615 (2)	0.065 (2)
C5	0.2343 (4)	0.2170 (2)	0.4289 (2)	0.067 (2)
C6	0.1240 (4)	0.2028 (2)	0.4418 (2)	0.068 (2)
C7	0.0119 (3)	0.1167 (2)	0.4446 (1)	0.053 (1)
C8	0.0033 (3)	0.0554 (2)	0.4393 (1)	0.050 (1)
C9	0.0909 (4)	−0.0382 (2)	0.4272 (2)	0.059 (1)
C10	0.1990 (4)	−0.0595 (2)	0.4188 (2)	0.059 (1)
C11	0.3329 (3)	−0.0594 (2)	0.3568 (2)	0.058 (1)
C12	0.3518 (3)	−0.0418 (2)	0.3037 (2)	0.057 (1)
C13	0.3741 (3)	0.0183 (2)	0.2109 (2)	0.061 (1)
C14	0.3847 (4)	0.0498 (3)	0.1667 (2)	0.072 (2)
C15	0.3841 (4)	0.1098 (3)	0.1668 (2)	0.074 (2)
C16	0.3746 (3)	0.1406 (2)	0.2118 (2)	0.063 (1)
C17	−0.0762 (4)	0.1503 (2)	0.4517 (2)	0.069 (2)
C18	−0.1743 (4)	0.1230 (3)	0.4524 (2)	0.078 (2)
C19	−0.1817 (4)	0.0636 (3)	0.4464 (2)	0.075 (2)
C20	−0.0939 (4)	0.0294 (2)	0.4401 (2)	0.065 (2)
C21	0.0785 (4)	0.4046 (2)	0.4967 (2)	0.067 (2)
C22	0.1855 (3)	0.3891 (2)	0.4146 (1)	0.052 (1)
C23	0.0913 (3)	0.3652 (2)	0.4045 (1)	0.053 (1)
C24	0.3441 (3)	0.2797 (2)	0.1202 (2)	0.059 (1)
C25	0.2349 (3)	0.2983 (2)	0.2011 (1)	0.049 (1)
C26	0.3292 (3)	0.3236 (2)	0.2109 (1)	0.050 (1)
C27	−0.0252 (5)	0.0778 (3)	0.3103 (2)	0.090 (2)
C28	−0.0843 (7)	0.1310 (5)	0.3090 (3)	0.195 (5)
C29	−0.0858 (7)	0.0223 (5)	0.3029 (3)	0.174 (4)
H1	0.4208	0.2131	0.2913	0.0763*
H2	0.2999	0.2154	0.2897	0.0763*
H3	0.3679	0.2563	0.3664	0.0792*
H4	0.4090	0.1934	0.3798	0.0792*
H5	0.2795	0.1962	0.4523	0.0825*
H6	0.2469	0.2585	0.4328	0.0825*
H7	0.0778	0.2204	0.4173	0.0840*
H8	0.1051	0.2183	0.4741	0.0840*
H9	0.0605	−0.0562	0.4566	0.0705*
H10	0.0478	−0.0484	0.3989	0.0705*
H11	0.2035	−0.1015	0.4226	0.0695*
H12	0.2446	−0.0418	0.4442	0.0695*
H13	0.3846	−0.0398	0.3785	0.0708*
H14	0.3425	−0.1013	0.3615	0.0708*
H15	0.2969	−0.0569	0.2828	0.0672*
H16	0.4166	−0.0576	0.2914	0.0672*
H17	0.3727	−0.0249	0.2108	0.0731*
H18	0.3947	0.0275	0.1353	0.0867*
H19	0.3906	0.1308	0.1349	0.0911*
H20	0.3738	0.1834	0.2119	0.0743*
H21	−0.0695	0.1929	0.4567	0.0851*
H22	−0.2358	0.1467	0.4576	0.0962*
H23	−0.2506	0.0445	0.4478	0.0906*
H24	−0.1000	−0.0140	0.4354	0.0803*
H25	−0.0814	0.1510	0.3389	0.2087*
H26	−0.0651	0.1543	0.2812	0.2087*
H27	−0.1599	0.1201	0.3029	0.2087*
H28	−0.1600	0.0299	0.2976	0.1957*
H29	−0.0631	0.0014	0.2725	0.1957*
H30	−0.0794	−0.0046	0.3300	0.1957*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0473 (3)	0.0516 (3)	0.0453 (3)	−0.0004 (2)	−0.0038 (2)	0.0035 (2)
K1	0.0613 (6)	0.0400 (5)	0.0663 (6)	−0.0021 (4)	0.0101 (4)	−0.0049 (4)
S1	0.0856 (9)	0.0887 (9)	0.0472 (7)	−0.0066 (6)	−0.0006 (6)	−0.0196 (7)
S2	0.107 (1)	0.130 (1)	0.0492 (8)	−0.0118 (8)	0.0117 (7)	0.0018 (10)
S3	0.0604 (7)	0.103 (1)	0.0518 (7)	−0.0018 (7)	0.0026 (5)	0.0047 (7)
S4	0.0477 (6)	0.0869 (9)	0.0515 (7)	−0.0095 (6)	−0.0027 (5)	−0.0014 (6)
S5	0.0608 (7)	0.0728 (8)	0.0516 (7)	−0.0065 (6)	0.0000 (5)	−0.0143 (6)
S6	0.0554 (6)	0.0687 (7)	0.0529 (6)	0.0027 (6)	0.0046 (5)	0.0007 (6)
S7	0.103 (1)	0.106 (1)	0.0517 (8)	−0.0068 (7)	0.0142 (7)	−0.0015 (9)
S8	0.0653 (7)	0.0677 (8)	0.0484 (7)	−0.0054 (6)	−0.0044 (5)	−0.0039 (6)
S9	0.0462 (6)	0.0718 (8)	0.0517 (6)	−0.0050 (5)	−0.0027 (5)	−0.0034 (5)
S10	0.0475 (6)	0.0616 (7)	0.0508 (6)	−0.0024 (5)	−0.0041 (5)	−0.0034 (5)
O1	0.062 (2)	0.039 (2)	0.055 (2)	0.000 (1)	−0.001 (1)	0.001 (1)
O2	0.063 (2)	0.036 (2)	0.066 (2)	0.007 (1)	0.001 (1)	−0.005 (1)
O3	0.067 (2)	0.047 (2)	0.068 (2)	−0.008 (1)	0.002 (2)	−0.012 (1)
O4	0.071 (2)	0.040 (2)	0.066 (2)	−0.003 (1)	0.007 (2)	−0.001 (1)
O5	0.065 (2)	0.042 (2)	0.062 (2)	−0.002 (1)	0.008 (1)	−0.005 (1)
O6	0.071 (2)	0.045 (2)	0.051 (2)	0.007 (1)	0.004 (1)	0.005 (1)
O7	0.064 (2)	0.137 (3)	0.091 (3)	−0.006 (2)	−0.018 (2)	0.008 (2)
C1	0.038 (2)	0.050 (3)	0.057 (3)	0.006 (2)	0.001 (2)	0.000 (2)
C2	0.037 (2)	0.058 (3)	0.057 (3)	0.005 (2)	0.003 (2)	0.000 (2)
C3	0.060 (3)	0.046 (3)	0.082 (3)	0.009 (2)	0.007 (2)	−0.004 (2)
C4	0.063 (3)	0.042 (2)	0.091 (4)	−0.001 (2)	0.000 (3)	−0.012 (2)
C5	0.089 (4)	0.040 (3)	0.072 (3)	−0.010 (2)	−0.004 (3)	−0.011 (2)
C6	0.094 (4)	0.039 (2)	0.072 (3)	−0.006 (2)	0.014 (3)	−0.004 (2)
C7	0.062 (3)	0.058 (3)	0.038 (2)	0.004 (2)	0.005 (2)	0.001 (2)
C8	0.062 (3)	0.054 (3)	0.035 (2)	−0.001 (2)	0.005 (2)	−0.004 (2)
C9	0.084 (3)	0.043 (3)	0.049 (3)	0.002 (2)	0.009 (2)	−0.011 (2)
C10	0.091 (3)	0.039 (2)	0.048 (3)	0.008 (2)	0.004 (2)	0.001 (2)
C11	0.071 (3)	0.036 (2)	0.067 (3)	0.004 (2)	−0.003 (2)	0.010 (2)
C12	0.066 (3)	0.036 (2)	0.068 (3)	−0.004 (2)	0.006 (2)	0.003 (2)
C13	0.058 (3)	0.065 (3)	0.061 (3)	−0.004 (2)	0.004 (2)	−0.001 (2)
C14	0.066 (3)	0.088 (4)	0.061 (3)	0.001 (3)	0.008 (2)	0.000 (3)
C15	0.063 (3)	0.107 (4)	0.052 (3)	0.015 (3)	0.007 (2)	−0.002 (3)
C16	0.050 (3)	0.063 (3)	0.076 (3)	0.023 (3)	0.002 (2)	−0.001 (2)
C17	0.089 (4)	0.067 (3)	0.052 (3)	0.004 (2)	0.011 (2)	0.011 (3)
C18	0.061 (3)	0.111 (5)	0.063 (3)	0.014 (3)	0.011 (2)	0.013 (3)
C19	0.072 (3)	0.090 (4)	0.065 (3)	0.009 (3)	0.003 (3)	−0.009 (3)
C20	0.074 (3)	0.069 (3)	0.051 (3)	0.004 (2)	0.007 (2)	−0.007 (3)
C21	0.081 (3)	0.077 (3)	0.043 (3)	0.004 (2)	−0.001 (2)	0.008 (3)
C22	0.061 (3)	0.055 (3)	0.042 (2)	0.005 (2)	−0.004 (2)	−0.001 (2)
C23	0.055 (3)	0.060 (3)	0.043 (2)	0.000 (2)	0.000 (2)	0.009 (2)
C24	0.071 (3)	0.055 (3)	0.049 (3)	0.010 (2)	0.001 (2)	0.006 (2)
C25	0.054 (2)	0.050 (2)	0.042 (2)	0.000 (2)	−0.005 (2)	0.004 (2)
C26	0.053 (2)	0.046 (2)	0.050 (2)	0.003 (2)	−0.002 (2)	0.009 (2)
C27	0.093 (4)	0.136 (6)	0.041 (3)	0.005 (3)	0.005 (3)	0.016 (4)
C28	0.196 (9)	0.28 (1)	0.105 (6)	−0.015 (7)	0.005 (6)	0.150 (9)
C29	0.182 (8)	0.23 (1)	0.110 (6)	0.039 (6)	−0.015 (5)	−0.125 (8)

Geometric parameters (Å, º)

Ni1—S4	2.168 (1)	O5—C8	1.366 (5)
Ni1—S5	2.163 (1)	O5—C9	1.431 (5)
Ni1—S9	2.156 (1)	O6—C10	1.418 (5)
Ni1—S10	2.166 (1)	O6—C11	1.424 (5)
S1—C21	1.716 (5)	O7—C27	1.170 (6)
S1—C22	1.740 (4)	C1—C2	1.395 (6)
S2—C21	1.645 (4)	C1—C13	1.375 (6)
S3—C21	1.732 (5)	C2—C16	1.380 (6)
S3—C23	1.750 (4)	C3—C4	1.498 (6)
S4—C23	1.719 (4)	C5—C6	1.492 (6)
S5—C22	1.717 (4)	C7—C8	1.388 (6)
S6—C24	1.726 (5)	C7—C17	1.372 (6)
S6—C26	1.746 (4)	C8—C20	1.377 (6)
S7—C24	1.637 (4)	C9—C10	1.484 (6)
S8—C24	1.735 (4)	C11—C12	1.486 (6)
S8—C25	1.741 (4)	C13—C14	1.378 (6)
S9—C25	1.719 (4)	C14—C15	1.349 (7)
S10—C26	1.710 (4)	C15—C16	1.389 (7)
O1—C1	1.372 (4)	C17—C18	1.399 (7)
O1—C12	1.420 (4)	C18—C19	1.348 (7)
O2—C2	1.375 (5)	C19—C20	1.373 (7)
O2—C3	1.421 (5)	C22—C23	1.347 (6)
O3—C4	1.427 (5)	C25—C26	1.360 (5)
O3—C5	1.398 (5)	C27—C28	1.416 (10)
O4—C6	1.436 (5)	C27—C29	1.481 (9)
O4—C7	1.381 (5)
K1···O1	2.719 (3)	S4···S9^i	3.637 (2)
K1···O2	2.691 (3)	S6···S10^ii	3.549 (2)
K1···O3	2.696 (3)	S9···S9^i	3.534 (2)
K1···O4	2.794 (3)	C1···C1^ii	3.486 (7)
K1···O5	2.734 (3)	C1···C13^ii	3.524 (6)
K1···O6	2.717 (3)	C2···C2^ii	3.479 (7)
K1···O7	2.611 (4)	C2···C16^ii	3.509 (6)
S4—Ni1—S5	93.01 (4)	C7—C8—C20	119.4 (4)
S4—Ni1—S9	87.14 (4)	O5—C9—C10	107.9 (3)
S4—Ni1—S10	179.07 (5)	O6—C10—C9	108.1 (3)
S5—Ni1—S9	178.15 (5)	O6—C11—C12	108.3 (3)
S5—Ni1—S10	87.19 (4)	O1—C12—C11	107.3 (3)
S9—Ni1—S10	92.69 (4)	C1—C13—C14	120.5 (4)
C21—S1—C22	97.9 (2)	C13—C14—C15	120.7 (5)
C21—S3—C23	97.2 (2)	C14—C15—C16	120.0 (4)
Ni1—S4—C23	101.8 (1)	C2—C16—C15	120.1 (4)
Ni1—S5—C22	102.2 (1)	C7—C17—C18	120.1 (5)
C24—S6—C26	97.7 (2)	C17—C18—C19	119.7 (5)
C24—S8—C25	97.1 (2)	C18—C19—C20	120.7 (5)
Ni1—S9—C25	102.6 (1)	C8—C20—C19	120.5 (4)
Ni1—S10—C26	102.6 (1)	S1—C21—S2	123.6 (3)
C1—O1—C12	117.3 (3)	S1—C21—S3	112.9 (2)
C2—O2—C3	118.4 (3)	S2—C21—S3	123.4 (3)
C4—O3—C5	113.8 (3)	S1—C22—S5	122.7 (2)
C6—O4—C7	117.6 (3)	S1—C22—C23	116.0 (3)
C8—O5—C9	118.8 (3)	S5—C22—C23	121.3 (3)
C10—O6—C11	114.1 (3)	S3—C23—S4	122.4 (3)
O1—C1—C2	115.0 (4)	S3—C23—C22	115.9 (3)
O1—C1—C13	125.7 (4)	S4—C23—C22	121.7 (3)
C2—C1—C13	119.2 (4)	S6—C24—S7	123.5 (3)
O2—C2—C1	115.1 (4)	S6—C24—S8	113.1 (2)
O2—C2—C16	125.3 (4)	S7—C24—S8	123.4 (3)
C1—C2—C16	119.6 (4)	S8—C25—S9	122.5 (2)
O2—C3—C4	108.0 (3)	S8—C25—C26	116.6 (3)
O3—C4—C3	107.5 (3)	S9—C25—C26	120.9 (3)
O3—C5—C6	108.9 (4)	S6—C26—S10	123.5 (2)
O4—C6—C5	108.2 (4)	S6—C26—C25	115.4 (3)
O4—C7—C8	115.5 (4)	S10—C26—C25	121.1 (3)
O4—C7—C17	124.9 (4)	O7—C27—C28	123.5 (8)
C8—C7—C17	119.6 (4)	O7—C27—C29	121.2 (7)
O5—C8—C7	116.1 (4)	C28—C27—C29	115.3 (8)
O5—C8—C20	124.5 (4)
Ni1—S4—C23—S3	−178.7 (2)	O2—C2—C16—C15	179.8 (4)
Ni1—S4—C23—C22	0.8 (4)	O2—C3—C4—O3	−67.5 (4)
Ni1—S5—C22—S1	179.3 (2)	O3—C5—C6—O4	64.6 (5)
Ni1—S5—C22—C23	0.0 (4)	O4—C7—C8—O5	1.9 (5)
Ni1—S9—C25—S8	179.5 (2)	O4—C7—C8—C20	−177.5 (4)
Ni1—S9—C25—C26	0.1 (4)	O4—C7—C17—C18	177.4 (4)
Ni1—S10—C26—S6	−178.7 (2)	O5—C8—C7—C17	−178.9 (4)
Ni1—S10—C26—C25	1.0 (4)	O5—C8—C20—C19	−179.8 (4)
S1—C21—S3—C23	−2.5 (3)	O5—C9—C10—O6	−71.4 (4)
S1—C22—C23—S3	−0.4 (5)	C1—O1—C12—C11	−176.7 (3)
S1—C22—C23—S4	−179.9 (2)	C1—C2—O2—C3	178.0 (3)
S2—C21—S1—C22	−179.8 (3)	C1—C2—C16—C15	−0.2 (6)
S2—C21—S3—C23	179.6 (3)	C1—C13—C14—C15	−1.2 (7)
S3—C21—S1—C22	2.4 (3)	C2—O2—C3—C4	−176.0 (3)
S3—C23—C22—S5	179.0 (2)	C2—C1—O1—C12	179.5 (3)
S4—Ni1—S5—C22	0.4 (2)	C2—C1—C13—C14	0.6 (6)
S4—Ni1—S9—C25	179.5 (1)	C2—C16—C15—C14	−0.4 (7)
S4—C23—S3—C21	−178.7 (3)	C3—O2—C2—C16	−2.0 (6)
S4—C23—C22—S5	−0.6 (5)	C3—C4—O3—C5	−173.4 (3)
S5—Ni1—S4—C23	−0.6 (1)	C4—O3—C5—C6	174.8 (3)
S5—Ni1—S10—C26	177.4 (1)	C5—C6—O4—C7	−170.1 (4)
S5—C22—S1—C21	179.5 (3)	C6—O4—C7—C8	174.3 (4)
S6—C24—S8—C25	−0.8 (3)	C6—O4—C7—C17	−4.8 (6)
S6—C26—C25—S8	−0.5 (4)	C7—C8—O5—C9	−179.6 (3)
S6—C26—C25—S9	178.9 (2)	C7—C8—C20—C19	−0.4 (6)
S7—C24—S6—C26	−179.0 (3)	C7—C17—C18—C19	0.6 (7)
S7—C24—S8—C25	178.8 (3)	C8—O5—C9—C10	177.4 (3)
S8—C24—S6—C26	0.6 (3)	C8—C7—C17—C18	−1.7 (6)
S8—C25—C26—S10	179.7 (2)	C8—C20—C19—C18	−0.7 (7)
S9—Ni1—S4—C23	177.5 (1)	C9—O5—C8—C20	−0.2 (6)
S9—Ni1—S10—C26	−0.7 (1)	C9—C10—O6—C11	−179.6 (3)
S9—C25—S8—C24	−178.6 (3)	C10—O6—C11—C12	175.6 (3)
S9—C25—C26—S10	−0.8 (5)	C12—O1—C1—C13	0.2 (5)
S10—Ni1—S5—C22	179.5 (2)	C13—C1—C2—C16	0.1 (6)
S10—Ni1—S9—C25	0.4 (1)	C13—C14—C15—C16	1.1 (7)
S10—C26—S6—C24	179.7 (3)	C17—C7—C8—C20	1.6 (6)
O1—C1—C2—O2	0.7 (5)	C17—C18—C19—C20	0.7 (8)
O1—C1—C2—C16	−179.3 (3)	C21—S1—C22—C23	−1.2 (4)
O1—C1—C13—C14	179.9 (4)	C21—S3—C23—C22	1.8 (4)
O1—C12—C11—O6	67.0 (4)	C24—S6—C26—C25	−0.1 (4)
O2—C2—C1—C13	−179.9 (3)	C24—S8—C25—C26	0.8 (4)

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