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

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ISSN: 2056-9890

N-Benzyl-N,N-di­methyl­octa­decan-1-aminium (2-thioxo-1,3-di­thiole-4,5-di­thiol­ato-κ2S4,S5)nickelate(III)

aSchool of Biochemical and Environmental Engineering, Nanjing Xiaozhuang University, Nanjing 211171, People's Republic of China
*Correspondence e-mail: liugx@njxzc.edu.cn

(Received 4 April 2012; accepted 17 April 2012; online 25 April 2012)

The asymmtric unit of the title compound, (C27H50N)[Ni(C3S5)2], contains two N-benzyl-N,N-dimethyl­octa­decan-1-aminium cations, [BDA]+, and two [Ni(dmit)2] anions (dmit = 2-thioxo-1,3-dithiole-4,5-dithiol­ate). The C18 chains in both cations adopt almost ideal extended conformations. The NiIII atoms are coordinated by two S,S′-bidentate ligands, generating NiS4 square planes. Short Ni⋯S [3.734 (2) Å] and S⋯S contacts [3.5438 (15) Å] occur in the crystal structure; if these are considered to be bonding inter­actions, then infinite sheets of anions parallel to (111) arise.

Related literature

For applications of bis­(dithiol­ate)-metal complexes, see: Cassoux (1999[Cassoux, P. (1999). Coord. Chem. Rev. 185-186, 213-232.]). For the oxidation of Ni(II) compounds, see: Cassoux et al. (1991[Cassoux, P., Valade, L., Kobayashi, H., Kobayashi, A., Clark, R. A. & Underhill, A. (1991). Coord. Chem. Rev. 110, 115-160.]). For the synthesis, see: Xue et al. (2003[Xue, G., Xu, W., Yu, W.-T. & Fang, Q. (2003). Acta Cryst. C59, m27-m29.]).

[Scheme 1]

Experimental

Crystal data
  • (C27H50N)[Ni(C3S5)2]

  • Mr = 840.05

  • Triclinic, [P \overline 1]

  • a = 12.1626 (16) Å

  • b = 12.2384 (16) Å

  • c = 27.778 (4) Å

  • α = 80.388 (2)°

  • β = 84.699 (2)°

  • γ = 87.431 (2)°

  • V = 4057.4 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.02 mm−1

  • T = 293 K

  • 0.26 × 0.14 × 0.12 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.778, Tmax = 0.888

  • 32319 measured reflections

  • 15041 independent reflections

  • 8322 reflections with I > 2σ(I)

  • Rint = 0.047

Refinement
  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.128

  • S = 1.01

  • 15041 reflections

  • 817 parameters

  • H-atom parameters constrained

  • Δρmax = 0.36 e Å−3

  • Δρmin = −0.32 e Å−3

Table 1
Selected bond lengths (Å)

Ni1—S2 2.1516 (10)
Ni1—S7 2.1607 (10)
Ni1—S6 2.1631 (10)
Ni1—S1 2.1657 (10)
Ni2—S11 2.1504 (11)
Ni2—S12 2.1591 (11)
Ni2—S17 2.1605 (11)
Ni2—S16 2.1615 (10)

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The bis(dithiolate)-metal complexes and their analogues with interesting structures and/or potential applications such as conducting/magnetic or non-linear optical (NLO) materials have been reported in recent years (Cassoux, 1999). We report herein the crystal structure of the title bis-dithiolate-metal complex. In this compound, the Ni(II) cations of NiCl2.6H2O have been oxidized to Ni(III) cation by I3- (Cassoux et al., 1991), the Ni(III) cation is coordinated with two dmit2- anions. As shown in Fig. 1, the asymmetric unit of the title compound contains two crystallographically independent [Ni(dmit)2]- anions and two [BDA]+ cations. Each Ni(III) ion is coordinated by four S atoms from two dmit ligands to complete a square-planar geometry, with Ni—S bond lengths ranging from 2.1504 (11) to 2.1657 (10) Å. Some of the [Ni(dmit)2]- anions are almost parallel each other with the shortest Ni···S distance of 3.734 (2) Å (Ni1—S1i) [symmetry code: (i) -x, 1 - y, -z], indicating the existence of the Ni···S interactions. Adjacent [Ni(dmit)2]- anions are associated together through such Ni···S interactions result in a dimer. The dimers linked together through S···S interactions forming a two-dimensional layer structure, as depicted in Fig 2. The shortest S···S distance in (I) is equal to the sum of the van der Waals radii and is much larger than that in an analogue with a smaller planar cation, namely N-methylpyridinium (Xue et al., 2003); i.e. a large cation appears to weaken the intermolecular interaction.

Related literature top

For applications of bis(dithiolate)-metal complexes, see: Cassoux (1999). For the oxidation of Ni(II) compounds, see: Cassoux et al. (1991). For the synthesis, see: Xue et al. (2003).

Experimental top

4,5-Di(thiobenzoyl)-1,3-dithiole-2-thione (812 mg, 2 mmol) was suspended in methanol (10 ml). Sodium methoxide in methanol (prepared form 184 mg of sodium in 10 ml of methanol) was added to the above mixture under argon atmosphere at room temperature from 30 min to give a dark red solution. To this solution, NiCl2.6H2O (238 mg, 1 mmol) was added. After 30 min, a solution of I2 (127 mg, 1 mmol) and NaI (150 mg, 1 mmol) in methanol (20 ml) was added (the monoanionic [Ni(dmit)2]- are obtained from the dianionic [Ni(dmit)2]2- by I3- oxidation). After another 10 min, a solution of N-benzyl-N,N-dimethyloctadecan-1-aminium bromide [(BDA)Br] (467 mg, 1 mmol) in methanol (20 ml) was added to the reaction mixture. The solution was stirred for 30 min and cooled in a refrigerator overnight. The resultant dark green crystal was collected by filtration, and purified by recrystallization using a mixed solvent of acetonitrile and benzene.

Refinement top

H atoms were positioned geometrically, with C—H = 0.93, 0.97 and 0.96 Å for aromatic, methylene and methyl H atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title complex, with displacement ellipsoids drawn at the 30% probabilility level.
[Figure 2] Fig. 2. The packing of the [Ni(dmit)2]- anions of (I), showing the S···S and Ni···S contacts as dashed lines.
N-Benzyl-N,N-dimethyloctadecan-1-aminium (2-thioxo-1,3-dithiole-4,5-dithiolato- κ2S4,S5)nickelate(III) top
Crystal data top
(C27H50N)[Ni(C3S5)2]Z = 4
Mr = 840.05F(000) = 1772
Triclinic, P1Dx = 1.375 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 12.1626 (16) ÅCell parameters from 4822 reflections
b = 12.2384 (16) Åθ = 2.3–25.0°
c = 27.778 (4) ŵ = 1.02 mm1
α = 80.388 (2)°T = 293 K
β = 84.699 (2)°Pillar, dark green
γ = 87.431 (2)°0.26 × 0.14 × 0.12 mm
V = 4057.4 (9) Å3
Data collection top
Bruker SMART APEX CCD
diffractometer
15041 independent reflections
Radiation source: sealed tube8322 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
phi and ω scansθmax = 25.5°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1414
Tmin = 0.778, Tmax = 0.888k = 1414
32319 measured reflectionsl = 3333
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0429P)2]
where P = (Fo2 + 2Fc2)/3
15041 reflections(Δ/σ)max = 0.001
817 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = 0.32 e Å3
Crystal data top
(C27H50N)[Ni(C3S5)2]γ = 87.431 (2)°
Mr = 840.05V = 4057.4 (9) Å3
Triclinic, P1Z = 4
a = 12.1626 (16) ÅMo Kα radiation
b = 12.2384 (16) ŵ = 1.02 mm1
c = 27.778 (4) ÅT = 293 K
α = 80.388 (2)°0.26 × 0.14 × 0.12 mm
β = 84.699 (2)°
Data collection top
Bruker SMART APEX CCD
diffractometer
15041 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
8322 reflections with I > 2σ(I)
Tmin = 0.778, Tmax = 0.888Rint = 0.047
32319 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.128H-atom parameters constrained
S = 1.01Δρmax = 0.36 e Å3
15041 reflectionsΔρmin = 0.32 e Å3
817 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
xyzUiso*/Ueq
Ni10.05179 (4)0.35723 (4)0.032575 (16)0.04308 (14)
Ni20.69111 (4)0.10274 (4)0.254025 (17)0.05030 (15)
S10.08628 (8)0.48570 (8)0.07358 (4)0.0545 (3)
S20.19929 (9)0.38608 (8)0.01624 (4)0.0590 (3)
S30.37592 (9)0.55667 (9)0.02434 (4)0.0631 (3)
S40.27316 (9)0.64806 (8)0.05830 (4)0.0598 (3)
S50.48282 (10)0.74269 (10)0.00753 (4)0.0778 (4)
S60.02245 (8)0.22901 (8)0.00930 (3)0.0537 (3)
S70.09346 (8)0.31986 (8)0.08262 (3)0.0520 (3)
S80.26307 (8)0.14141 (9)0.08832 (4)0.0582 (3)
S90.15202 (9)0.05522 (8)0.00610 (4)0.0607 (3)
S100.35037 (11)0.05852 (11)0.05959 (5)0.0867 (4)
S110.55325 (9)0.05210 (10)0.30595 (4)0.0687 (3)
S120.65622 (8)0.01272 (8)0.20693 (4)0.0584 (3)
S130.47558 (9)0.17986 (9)0.21650 (4)0.0698 (3)
S140.38445 (9)0.12578 (10)0.30928 (4)0.0716 (3)
S150.27330 (11)0.29187 (10)0.26532 (5)0.0878 (4)
S160.82672 (8)0.15752 (8)0.20082 (3)0.0553 (3)
S170.72739 (9)0.21521 (9)0.30230 (4)0.0673 (3)
S180.91155 (10)0.37827 (9)0.29458 (4)0.0715 (3)
S190.99621 (9)0.33305 (9)0.19927 (4)0.0639 (3)
S201.11358 (11)0.49132 (10)0.24523 (5)0.0823 (4)
C10.2066 (3)0.5381 (3)0.04195 (13)0.0458 (9)
C20.2543 (3)0.4952 (3)0.00342 (14)0.0495 (10)
C30.3832 (3)0.6548 (3)0.01319 (13)0.0539 (10)
C40.0936 (3)0.1692 (3)0.02237 (13)0.0445 (9)
C50.1446 (3)0.2096 (3)0.06152 (13)0.0445 (9)
C60.2612 (3)0.0408 (3)0.05143 (13)0.0559 (10)
C70.4994 (3)0.0516 (3)0.28179 (14)0.0560 (11)
C80.5432 (3)0.0792 (3)0.23878 (15)0.0526 (10)
C90.3723 (3)0.2051 (3)0.26411 (15)0.0648 (12)
C100.8830 (3)0.2570 (3)0.22686 (15)0.0552 (10)
C110.8407 (3)0.2809 (3)0.27110 (15)0.0562 (10)
C121.0123 (3)0.4058 (3)0.24629 (14)0.0602 (11)
C130.4816 (4)0.1271 (4)0.57662 (17)0.0990 (17)
H13A0.53110.08800.55430.148*
H13B0.52160.15090.60780.148*
H13C0.44940.19050.56380.148*
C140.3907 (4)0.0509 (4)0.58300 (17)0.0916 (16)
H14A0.42410.01390.59510.110*
H14B0.34460.08910.60760.110*
C150.3207 (4)0.0145 (4)0.53761 (17)0.0869 (15)
H15A0.36760.02310.51320.104*
H15B0.28830.07980.52570.104*
C160.2275 (4)0.0626 (4)0.54168 (16)0.0806 (14)
H16A0.25890.12840.55350.097*
H16B0.17900.02530.56550.097*
C170.1607 (4)0.0967 (4)0.49352 (16)0.0817 (14)
H17A0.20990.13360.46990.098*
H17B0.13060.03030.48180.098*
C180.0667 (4)0.1725 (4)0.49489 (16)0.0794 (14)
H18A0.01750.13640.51860.095*
H18B0.09650.23980.50590.095*
C190.0007 (4)0.2033 (4)0.44582 (16)0.0769 (13)
H19A0.02760.13580.43450.092*
H19B0.04970.24070.42230.092*
C200.0949 (3)0.2772 (4)0.44726 (15)0.0733 (13)
H20A0.06620.34570.45750.088*
H20B0.14240.24090.47170.088*
C210.1637 (3)0.3050 (4)0.39889 (15)0.0740 (13)
H21A0.11680.34340.37470.089*
H21B0.19060.23640.38810.089*
C220.2614 (3)0.3760 (4)0.40075 (15)0.0719 (12)
H22A0.23390.44670.40920.086*
H22B0.30490.34020.42680.086*
C230.3359 (3)0.3977 (4)0.35408 (15)0.0740 (13)
H23A0.29250.43330.32790.089*
H23B0.36410.32720.34570.089*
C240.4328 (4)0.4695 (4)0.35642 (15)0.0779 (14)
H24A0.47510.43520.38320.094*
H24B0.40470.54090.36370.094*
C250.5095 (3)0.4883 (3)0.30979 (14)0.0648 (12)
H25A0.46640.51870.28270.078*
H25B0.54070.41720.30350.078*
C260.6033 (3)0.5655 (4)0.31108 (14)0.0697 (12)
H26A0.57260.63530.31930.084*
H26B0.64950.53290.33670.084*
C270.6743 (3)0.5881 (3)0.26295 (13)0.0633 (11)
H27A0.70850.51870.25590.076*
H27B0.62710.61590.23700.076*
C280.7639 (3)0.6704 (3)0.26225 (13)0.0620 (11)
H28A0.81510.63960.28610.074*
H28B0.73060.73760.27210.074*
C290.8278 (3)0.6999 (3)0.21268 (14)0.0644 (12)
H29A0.86040.63300.20210.077*
H29B0.77800.73370.18880.077*
C300.9176 (3)0.7791 (3)0.21544 (13)0.0600 (11)
H30A0.96750.74250.23880.072*
H30B0.88360.84230.22860.072*
C310.9149 (3)0.8873 (3)0.13133 (13)0.0631 (11)
H31A0.87540.94560.14540.095*
H31B0.86330.83880.12230.095*
H31C0.96050.91880.10270.095*
C321.0434 (3)0.7289 (3)0.14640 (15)0.0694 (12)
H32A0.98930.68070.13910.104*
H32B1.09050.68800.16940.104*
H32C1.08700.75790.11680.104*
C331.0686 (3)0.8990 (3)0.18233 (13)0.0603 (11)
H33A1.02740.95970.19470.072*
H33B1.10680.85790.20910.072*
C341.1540 (3)0.9476 (3)0.14287 (14)0.0532 (10)
C351.2525 (3)0.8925 (3)0.13538 (15)0.0662 (12)
H351.26430.82250.15340.079*
C361.3354 (4)0.9389 (4)0.10130 (17)0.0789 (14)
H361.40230.90050.09680.095*
C371.3180 (5)1.0408 (4)0.07455 (16)0.0792 (15)
H371.37331.07170.05160.095*
C381.2212 (5)1.0979 (4)0.08092 (17)0.0808 (15)
H381.20981.16720.06210.097*
C391.1385 (4)1.0523 (4)0.11584 (16)0.0674 (12)
H391.07281.09220.12100.081*
C400.0553 (5)0.3611 (5)0.6307 (2)0.128 (2)
H40A0.01170.32570.65640.193*
H40B0.11070.31170.62570.193*
H40C0.09030.42740.63990.193*
C410.0174 (4)0.3900 (4)0.58462 (18)0.0980 (16)
H41A0.02790.42580.55920.118*
H41B0.04810.32180.57480.118*
C420.1109 (4)0.4643 (4)0.58701 (16)0.0789 (13)
H42A0.15760.42800.61180.095*
H42B0.08070.53210.59740.095*
C430.1815 (4)0.4942 (4)0.53954 (16)0.0811 (14)
H43A0.21160.42600.52940.097*
H43B0.13420.52930.51480.097*
C440.2751 (4)0.5688 (4)0.54003 (16)0.0816 (14)
H44A0.32350.53350.56430.098*
H44B0.24550.63690.55040.098*
C450.3429 (4)0.5977 (4)0.49172 (16)0.0810 (14)
H45A0.37250.52970.48140.097*
H45B0.29460.63320.46740.097*
C460.4369 (4)0.6729 (4)0.49267 (16)0.0802 (14)
H46A0.48400.63810.51760.096*
H46B0.40680.74150.50240.096*
C470.5081 (4)0.7010 (4)0.44420 (16)0.0788 (13)
H47A0.53930.63270.43470.095*
H47B0.46110.73500.41910.095*
C480.6011 (4)0.7779 (4)0.44564 (16)0.0789 (13)
H48A0.56950.84750.45360.095*
H48B0.64590.74560.47190.095*
C490.6753 (4)0.8019 (4)0.39876 (15)0.0751 (13)
H49A0.63050.83290.37240.090*
H49B0.70830.73240.39110.090*
C500.7668 (4)0.8808 (4)0.40021 (16)0.0765 (13)
H50A0.80910.85200.42780.092*
H50B0.73380.95160.40590.092*
C510.8450 (4)0.8995 (3)0.35412 (14)0.0712 (12)
H51A0.80250.92860.32670.085*
H51B0.87720.82840.34840.085*
C520.9382 (4)0.9777 (4)0.35481 (15)0.0743 (13)
H52A0.90651.04940.36010.089*
H52B0.98090.94910.38220.089*
C531.0143 (4)0.9933 (3)0.30868 (14)0.0697 (12)
H53A0.96961.01350.28120.084*
H53B1.05050.92230.30540.084*
C541.1025 (3)1.0783 (4)0.30422 (15)0.0708 (12)
H54A1.06731.15000.30690.085*
H54B1.14851.05860.33130.085*
C551.1744 (3)1.0877 (3)0.25698 (14)0.0667 (12)
H55A1.12681.09940.23030.080*
H55B1.21371.01730.25600.080*
C561.2597 (3)1.1795 (3)0.24710 (15)0.0701 (12)
H56A1.22201.25140.24120.084*
H56B1.30091.17670.27560.084*
C571.3379 (4)1.1648 (3)0.20322 (15)0.0711 (13)
H57A1.29871.12870.18170.085*
H57B1.39761.11450.21450.085*
C581.3050 (4)1.3378 (3)0.14485 (16)0.0792 (14)
H58A1.34071.39560.12190.119*
H58B1.25361.37020.16720.119*
H58C1.26621.29220.12750.119*
C591.4756 (3)1.2293 (3)0.13660 (15)0.0750 (13)
H59A1.44191.18390.11740.113*
H59B1.53211.18670.15400.113*
H59C1.50781.29200.11540.113*
C601.4428 (3)1.3343 (3)0.20586 (14)0.0636 (11)
H60A1.38561.36080.22820.076*
H60B1.49241.28490.22540.076*
C611.5070 (4)1.4322 (3)0.17860 (13)0.0550 (10)
C621.4553 (4)1.5329 (4)0.16524 (15)0.0685 (12)
H621.38031.54250.17410.082*
C631.5138 (5)1.6200 (4)0.13867 (16)0.0741 (13)
H631.47751.68770.12940.089*
C641.6239 (5)1.6089 (4)0.12581 (15)0.0765 (14)
H641.66241.66820.10770.092*
C651.6780 (4)1.5084 (4)0.13985 (16)0.0727 (13)
H651.75341.49990.13160.087*
C661.6190 (4)1.4205 (3)0.16644 (14)0.0636 (11)
H661.65521.35300.17620.076*
N10.9864 (2)0.8228 (2)0.16809 (10)0.0490 (8)
N21.3894 (3)1.2690 (3)0.17266 (11)0.0577 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0433 (3)0.0436 (3)0.0423 (3)0.0071 (2)0.0000 (2)0.0074 (2)
Ni20.0481 (3)0.0541 (3)0.0489 (3)0.0058 (2)0.0017 (2)0.0093 (2)
S10.0518 (6)0.0551 (6)0.0590 (6)0.0111 (5)0.0069 (5)0.0201 (5)
S20.0594 (7)0.0645 (7)0.0563 (6)0.0255 (5)0.0151 (5)0.0241 (5)
S30.0615 (7)0.0715 (7)0.0579 (7)0.0288 (6)0.0084 (5)0.0151 (6)
S40.0631 (7)0.0540 (6)0.0662 (7)0.0150 (5)0.0015 (6)0.0198 (5)
S50.0853 (9)0.0785 (8)0.0710 (8)0.0465 (7)0.0046 (6)0.0059 (6)
S60.0531 (6)0.0619 (6)0.0488 (6)0.0193 (5)0.0104 (5)0.0200 (5)
S70.0495 (6)0.0576 (6)0.0511 (6)0.0105 (5)0.0085 (5)0.0201 (5)
S80.0436 (6)0.0780 (7)0.0531 (6)0.0183 (5)0.0053 (5)0.0123 (5)
S90.0614 (7)0.0656 (7)0.0597 (7)0.0221 (6)0.0037 (5)0.0228 (6)
S100.0811 (9)0.0988 (9)0.0826 (9)0.0529 (8)0.0003 (7)0.0119 (7)
S110.0667 (8)0.0880 (8)0.0548 (7)0.0230 (6)0.0095 (6)0.0240 (6)
S120.0528 (7)0.0647 (7)0.0595 (7)0.0120 (5)0.0076 (5)0.0193 (5)
S130.0619 (8)0.0692 (7)0.0832 (8)0.0139 (6)0.0026 (6)0.0258 (6)
S140.0611 (8)0.0866 (8)0.0648 (7)0.0230 (6)0.0034 (6)0.0047 (6)
S150.0737 (9)0.0810 (9)0.1069 (10)0.0317 (7)0.0152 (7)0.0021 (8)
S160.0554 (7)0.0647 (7)0.0485 (6)0.0156 (5)0.0005 (5)0.0157 (5)
S170.0665 (8)0.0761 (8)0.0627 (7)0.0152 (6)0.0078 (6)0.0255 (6)
S180.0752 (8)0.0688 (7)0.0786 (8)0.0104 (6)0.0094 (6)0.0317 (6)
S190.0586 (7)0.0724 (7)0.0622 (7)0.0209 (6)0.0065 (5)0.0098 (6)
S200.0809 (9)0.0668 (8)0.1041 (10)0.0231 (7)0.0249 (7)0.0133 (7)
C10.048 (2)0.040 (2)0.049 (2)0.0065 (18)0.0109 (19)0.0029 (18)
C20.043 (2)0.048 (2)0.054 (2)0.0156 (18)0.0002 (19)0.0022 (19)
C30.063 (3)0.049 (2)0.047 (2)0.010 (2)0.009 (2)0.0026 (19)
C40.045 (2)0.046 (2)0.043 (2)0.0063 (18)0.0103 (18)0.0051 (18)
C50.033 (2)0.052 (2)0.048 (2)0.0062 (17)0.0065 (17)0.0005 (18)
C60.056 (3)0.067 (3)0.046 (2)0.011 (2)0.0079 (19)0.006 (2)
C70.049 (3)0.063 (3)0.051 (3)0.004 (2)0.003 (2)0.005 (2)
C80.042 (2)0.049 (2)0.067 (3)0.0038 (18)0.013 (2)0.007 (2)
C90.055 (3)0.066 (3)0.069 (3)0.004 (2)0.014 (2)0.005 (2)
C100.050 (3)0.053 (2)0.062 (3)0.007 (2)0.013 (2)0.002 (2)
C110.053 (3)0.050 (2)0.068 (3)0.004 (2)0.014 (2)0.012 (2)
C120.058 (3)0.053 (2)0.069 (3)0.000 (2)0.014 (2)0.006 (2)
C130.105 (4)0.114 (4)0.082 (4)0.032 (3)0.010 (3)0.028 (3)
C140.093 (4)0.104 (4)0.077 (3)0.019 (3)0.012 (3)0.017 (3)
C150.089 (4)0.087 (3)0.081 (4)0.011 (3)0.005 (3)0.010 (3)
C160.074 (3)0.084 (3)0.079 (3)0.008 (3)0.006 (3)0.006 (3)
C170.086 (4)0.076 (3)0.079 (3)0.005 (3)0.010 (3)0.010 (3)
C180.067 (3)0.086 (3)0.083 (3)0.012 (3)0.006 (3)0.011 (3)
C190.069 (3)0.085 (3)0.074 (3)0.008 (3)0.007 (2)0.010 (3)
C200.061 (3)0.080 (3)0.077 (3)0.005 (2)0.004 (2)0.013 (3)
C210.067 (3)0.086 (3)0.069 (3)0.011 (3)0.001 (2)0.014 (3)
C220.063 (3)0.086 (3)0.065 (3)0.010 (3)0.002 (2)0.009 (2)
C230.069 (3)0.091 (3)0.061 (3)0.014 (3)0.009 (2)0.004 (3)
C240.072 (3)0.107 (4)0.055 (3)0.019 (3)0.003 (2)0.010 (3)
C250.063 (3)0.080 (3)0.051 (3)0.007 (2)0.008 (2)0.008 (2)
C260.068 (3)0.092 (3)0.048 (3)0.020 (3)0.005 (2)0.007 (2)
C270.062 (3)0.076 (3)0.050 (3)0.007 (2)0.004 (2)0.006 (2)
C280.065 (3)0.071 (3)0.050 (3)0.007 (2)0.005 (2)0.007 (2)
C290.070 (3)0.074 (3)0.050 (3)0.013 (2)0.002 (2)0.011 (2)
C300.065 (3)0.072 (3)0.043 (2)0.003 (2)0.001 (2)0.012 (2)
C310.063 (3)0.074 (3)0.050 (3)0.003 (2)0.010 (2)0.004 (2)
C320.069 (3)0.064 (3)0.073 (3)0.010 (2)0.011 (2)0.019 (2)
C330.053 (3)0.079 (3)0.052 (3)0.010 (2)0.005 (2)0.017 (2)
C340.057 (3)0.055 (3)0.048 (2)0.001 (2)0.009 (2)0.008 (2)
C350.059 (3)0.062 (3)0.071 (3)0.003 (2)0.002 (2)0.004 (2)
C360.063 (3)0.083 (3)0.090 (4)0.013 (3)0.012 (3)0.020 (3)
C370.096 (4)0.087 (4)0.056 (3)0.043 (3)0.007 (3)0.006 (3)
C380.116 (5)0.063 (3)0.066 (3)0.028 (3)0.038 (3)0.008 (3)
C390.071 (3)0.066 (3)0.073 (3)0.001 (2)0.022 (3)0.023 (3)
C400.121 (5)0.126 (5)0.120 (5)0.002 (4)0.034 (4)0.006 (4)
C410.101 (4)0.092 (4)0.094 (4)0.001 (3)0.004 (3)0.000 (3)
C420.082 (4)0.083 (3)0.072 (3)0.001 (3)0.007 (3)0.014 (3)
C430.093 (4)0.077 (3)0.071 (3)0.001 (3)0.007 (3)0.007 (3)
C440.084 (4)0.082 (3)0.078 (3)0.001 (3)0.008 (3)0.014 (3)
C450.087 (4)0.078 (3)0.077 (3)0.003 (3)0.003 (3)0.011 (3)
C460.076 (3)0.084 (3)0.081 (3)0.002 (3)0.005 (3)0.015 (3)
C470.086 (4)0.078 (3)0.072 (3)0.002 (3)0.003 (3)0.012 (3)
C480.073 (3)0.089 (3)0.074 (3)0.006 (3)0.002 (3)0.014 (3)
C490.081 (3)0.076 (3)0.065 (3)0.002 (3)0.003 (3)0.006 (2)
C500.073 (3)0.083 (3)0.071 (3)0.001 (3)0.002 (3)0.012 (3)
C510.080 (3)0.076 (3)0.054 (3)0.005 (3)0.001 (2)0.005 (2)
C520.071 (3)0.090 (3)0.061 (3)0.002 (3)0.003 (2)0.014 (3)
C530.079 (3)0.072 (3)0.054 (3)0.001 (3)0.001 (2)0.003 (2)
C540.073 (3)0.081 (3)0.061 (3)0.008 (3)0.008 (2)0.013 (2)
C550.076 (3)0.062 (3)0.061 (3)0.000 (2)0.005 (2)0.008 (2)
C560.068 (3)0.076 (3)0.066 (3)0.008 (2)0.002 (2)0.014 (2)
C570.073 (3)0.066 (3)0.074 (3)0.014 (2)0.008 (3)0.014 (2)
C580.078 (3)0.079 (3)0.086 (3)0.005 (3)0.033 (3)0.017 (3)
C590.082 (3)0.077 (3)0.069 (3)0.003 (3)0.011 (3)0.027 (2)
C600.061 (3)0.080 (3)0.052 (3)0.001 (2)0.007 (2)0.016 (2)
C610.061 (3)0.063 (3)0.045 (2)0.001 (2)0.007 (2)0.018 (2)
C620.075 (3)0.072 (3)0.064 (3)0.006 (3)0.014 (2)0.027 (3)
C630.107 (4)0.062 (3)0.057 (3)0.003 (3)0.010 (3)0.022 (2)
C640.112 (4)0.071 (3)0.050 (3)0.024 (3)0.007 (3)0.023 (2)
C650.068 (3)0.086 (4)0.069 (3)0.015 (3)0.010 (2)0.033 (3)
C660.072 (3)0.061 (3)0.060 (3)0.002 (2)0.011 (2)0.017 (2)
N10.0452 (19)0.059 (2)0.0420 (18)0.0037 (16)0.0006 (15)0.0088 (16)
N20.055 (2)0.069 (2)0.050 (2)0.0030 (18)0.0023 (17)0.0124 (18)
Geometric parameters (Å, º) top
Ni1—S22.1516 (10)C31—H31C0.9600
Ni1—S72.1607 (10)C32—N11.499 (4)
Ni1—S62.1631 (10)C32—H32A0.9600
Ni1—S12.1657 (10)C32—H32B0.9600
Ni2—S112.1504 (11)C32—H32C0.9600
Ni2—S122.1591 (11)C33—C341.505 (5)
Ni2—S172.1605 (11)C33—N11.519 (4)
Ni2—S162.1615 (10)C33—H33A0.9700
S1—C11.727 (4)C33—H33B0.9700
S2—C21.709 (4)C34—C351.364 (5)
S3—C31.727 (4)C34—C391.387 (5)
S3—C21.745 (3)C35—C361.390 (5)
S4—C31.742 (4)C35—H350.9300
S4—C11.744 (3)C36—C371.359 (6)
S5—C31.635 (4)C36—H360.9300
S6—C41.718 (3)C37—C381.355 (6)
S7—C51.720 (3)C37—H370.9300
S8—C61.726 (4)C38—C391.398 (6)
S8—C51.740 (3)C38—H380.9300
S9—C41.736 (3)C39—H390.9300
S9—C61.737 (4)C40—C411.488 (6)
S10—C61.639 (4)C40—H40A0.9600
S11—C71.712 (4)C40—H40B0.9600
S12—C81.723 (4)C40—H40C0.9600
S13—C91.736 (4)C41—C421.500 (6)
S13—C81.737 (4)C41—H41A0.9700
S14—C91.730 (4)C41—H41B0.9700
S14—C71.746 (4)C42—C431.506 (5)
S15—C91.635 (4)C42—H42A0.9700
S16—C101.713 (4)C42—H42B0.9700
S17—C111.715 (4)C43—C441.493 (5)
S18—C121.731 (4)C43—H43A0.9700
S18—C111.745 (4)C43—H43B0.9700
S19—C121.729 (4)C44—C451.506 (5)
S19—C101.741 (4)C44—H44A0.9700
S20—C121.647 (4)C44—H44B0.9700
C1—C21.343 (5)C45—C461.504 (5)
C4—C51.357 (5)C45—H45A0.9700
C7—C81.351 (5)C45—H45B0.9700
C10—C111.360 (5)C46—C471.529 (5)
C13—C141.518 (5)C46—H46A0.9700
C13—H13A0.9600C46—H46B0.9700
C13—H13B0.9600C47—C481.510 (5)
C13—H13C0.9600C47—H47A0.9700
C14—C151.470 (5)C47—H47B0.9700
C14—H14A0.9700C48—C491.509 (5)
C14—H14B0.9700C48—H48A0.9700
C15—C161.531 (5)C48—H48B0.9700
C15—H15A0.9700C49—C501.513 (5)
C15—H15B0.9700C49—H49A0.9700
C16—C171.506 (5)C49—H49B0.9700
C16—H16A0.9700C50—C511.514 (5)
C16—H16B0.9700C50—H50A0.9700
C17—C181.511 (5)C50—H50B0.9700
C17—H17A0.9700C51—C521.519 (5)
C17—H17B0.9700C51—H51A0.9700
C18—C191.516 (5)C51—H51B0.9700
C18—H18A0.9700C52—C531.500 (5)
C18—H18B0.9700C52—H52A0.9700
C19—C201.513 (5)C52—H52B0.9700
C19—H19A0.9700C53—C541.510 (5)
C19—H19B0.9700C53—H53A0.9700
C20—C211.512 (5)C53—H53B0.9700
C20—H20A0.9700C54—C551.499 (5)
C20—H20B0.9700C54—H54A0.9700
C21—C221.513 (5)C54—H54B0.9700
C21—H21A0.9700C55—C561.537 (5)
C21—H21B0.9700C55—H55A0.9700
C22—C231.504 (5)C55—H55B0.9700
C22—H22A0.9700C56—C571.506 (5)
C22—H22B0.9700C56—H56A0.9700
C23—C241.514 (5)C56—H56B0.9700
C23—H23A0.9700C57—N21.533 (4)
C23—H23B0.9700C57—H57A0.9700
C24—C251.515 (5)C57—H57B0.9700
C24—H24A0.9700C58—N21.488 (5)
C24—H24B0.9700C58—H58A0.9600
C25—C261.522 (5)C58—H58B0.9600
C25—H25A0.9700C58—H58C0.9600
C25—H25B0.9700C59—N21.503 (4)
C26—C271.514 (5)C59—H59A0.9600
C26—H26A0.9700C59—H59B0.9600
C26—H26B0.9700C59—H59C0.9600
C27—C281.514 (5)C60—C611.513 (5)
C27—H27A0.9700C60—N21.521 (4)
C27—H27B0.9700C60—H60A0.9700
C28—C291.514 (5)C60—H60B0.9700
C28—H28A0.9700C61—C621.368 (5)
C28—H28B0.9700C61—C661.380 (5)
C29—C301.508 (5)C62—C631.378 (5)
C29—H29A0.9700C62—H620.9300
C29—H29B0.9700C63—C641.360 (6)
C30—N11.522 (4)C63—H630.9300
C30—H30A0.9700C64—C651.382 (6)
C30—H30B0.9700C64—H640.9300
C31—N11.501 (4)C65—C661.387 (5)
C31—H31A0.9600C65—H650.9300
C31—H31B0.9600C66—H660.9300
S2—Ni1—S7177.16 (5)H32A—C32—H32C109.5
S2—Ni1—S685.19 (4)H32B—C32—H32C109.5
S7—Ni1—S693.30 (4)C34—C33—N1117.0 (3)
S2—Ni1—S193.15 (4)C34—C33—H33A108.1
S7—Ni1—S188.33 (4)N1—C33—H33A108.1
S6—Ni1—S1178.28 (4)C34—C33—H33B108.1
S11—Ni2—S1292.97 (4)N1—C33—H33B108.1
S11—Ni2—S1786.67 (4)H33A—C33—H33B107.3
S12—Ni2—S17178.72 (5)C35—C34—C39118.4 (4)
S11—Ni2—S16178.34 (5)C35—C34—C33120.2 (4)
S12—Ni2—S1687.17 (4)C39—C34—C33121.2 (4)
S17—Ni2—S1693.22 (4)C34—C35—C36121.3 (4)
C1—S1—Ni1101.54 (13)C34—C35—H35119.4
C2—S2—Ni1102.33 (13)C36—C35—H35119.4
C3—S3—C298.11 (18)C37—C36—C35119.5 (5)
C3—S4—C197.51 (18)C37—C36—H36120.2
C4—S6—Ni1102.04 (12)C35—C36—H36120.2
C5—S7—Ni1101.94 (12)C38—C37—C36120.8 (5)
C6—S8—C598.40 (17)C38—C37—H37119.6
C4—S9—C697.65 (17)C36—C37—H37119.6
C7—S11—Ni2102.71 (14)C37—C38—C39119.7 (4)
C8—S12—Ni2102.07 (14)C37—C38—H38120.1
C9—S13—C897.8 (2)C39—C38—H38120.1
C9—S14—C797.88 (19)C34—C39—C38120.2 (4)
C10—S16—Ni2102.23 (14)C34—C39—H39119.9
C11—S17—Ni2101.98 (14)C38—C39—H39119.9
C12—S18—C1197.58 (19)C41—C40—H40A109.5
C12—S19—C1097.68 (19)C41—C40—H40B109.5
C2—C1—S1121.3 (3)H40A—C40—H40B109.5
C2—C1—S4116.4 (3)C41—C40—H40C109.5
S1—C1—S4122.3 (2)H40A—C40—H40C109.5
C1—C2—S2121.6 (3)H40B—C40—H40C109.5
C1—C2—S3115.8 (3)C40—C41—C42115.9 (5)
S2—C2—S3122.6 (2)C40—C41—H41A108.3
S5—C3—S3123.9 (2)C42—C41—H41A108.3
S5—C3—S4123.9 (2)C40—C41—H41B108.3
S3—C3—S4112.2 (2)C42—C41—H41B108.3
C5—C4—S6121.2 (3)H41A—C41—H41B107.4
C5—C4—S9116.6 (3)C41—C42—C43114.8 (4)
S6—C4—S9122.2 (2)C41—C42—H42A108.6
C4—C5—S7121.5 (3)C43—C42—H42A108.6
C4—C5—S8115.2 (3)C41—C42—H42B108.6
S7—C5—S8123.4 (2)C43—C42—H42B108.6
S10—C6—S8123.5 (2)H42A—C42—H42B107.6
S10—C6—S9124.3 (2)C44—C43—C42116.7 (4)
S8—C6—S9112.1 (2)C44—C43—H43A108.1
C8—C7—S11121.0 (3)C42—C43—H43A108.1
C8—C7—S14115.6 (3)C44—C43—H43B108.1
S11—C7—S14123.3 (2)C42—C43—H43B108.1
C7—C8—S12121.2 (3)H43A—C43—H43B107.3
C7—C8—S13116.3 (3)C43—C44—C45115.0 (4)
S12—C8—S13122.4 (2)C43—C44—H44A108.5
S15—C9—S14124.0 (3)C45—C44—H44A108.5
S15—C9—S13123.7 (3)C43—C44—H44B108.5
S14—C9—S13112.3 (2)C45—C44—H44B108.5
C11—C10—S16121.0 (3)H44A—C44—H44B107.5
C11—C10—S19115.9 (3)C46—C45—C44114.6 (4)
S16—C10—S19123.0 (2)C46—C45—H45A108.6
C10—C11—S17121.5 (3)C44—C45—H45A108.6
C10—C11—S18115.8 (3)C46—C45—H45B108.6
S17—C11—S18122.6 (2)C44—C45—H45B108.6
S20—C12—S19123.4 (2)H45A—C45—H45B107.6
S20—C12—S18123.8 (2)C45—C46—C47115.2 (4)
S19—C12—S18112.9 (2)C45—C46—H46A108.5
C14—C13—H13A109.5C47—C46—H46A108.5
C14—C13—H13B109.5C45—C46—H46B108.5
H13A—C13—H13B109.5C47—C46—H46B108.5
C14—C13—H13C109.5H46A—C46—H46B107.5
H13A—C13—H13C109.5C48—C47—C46114.5 (4)
H13B—C13—H13C109.5C48—C47—H47A108.6
C15—C14—C13113.6 (4)C46—C47—H47A108.6
C15—C14—H14A108.9C48—C47—H47B108.6
C13—C14—H14A108.9C46—C47—H47B108.6
C15—C14—H14B108.9H47A—C47—H47B107.6
C13—C14—H14B108.9C49—C48—C47115.0 (4)
H14A—C14—H14B107.7C49—C48—H48A108.5
C14—C15—C16116.1 (4)C47—C48—H48A108.5
C14—C15—H15A108.3C49—C48—H48B108.5
C16—C15—H15A108.3C47—C48—H48B108.5
C14—C15—H15B108.3H48A—C48—H48B107.5
C16—C15—H15B108.3C48—C49—C50114.6 (4)
H15A—C15—H15B107.4C48—C49—H49A108.6
C17—C16—C15112.6 (4)C50—C49—H49A108.6
C17—C16—H16A109.1C48—C49—H49B108.6
C15—C16—H16A109.1C50—C49—H49B108.6
C17—C16—H16B109.1H49A—C49—H49B107.6
C15—C16—H16B109.1C49—C50—C51114.4 (4)
H16A—C16—H16B107.8C49—C50—H50A108.7
C16—C17—C18115.4 (4)C51—C50—H50A108.7
C16—C17—H17A108.4C49—C50—H50B108.7
C18—C17—H17A108.4C51—C50—H50B108.7
C16—C17—H17B108.4H50A—C50—H50B107.6
C18—C17—H17B108.4C50—C51—C52115.5 (4)
H17A—C17—H17B107.5C50—C51—H51A108.4
C17—C18—C19113.6 (4)C52—C51—H51A108.4
C17—C18—H18A108.8C50—C51—H51B108.4
C19—C18—H18A108.8C52—C51—H51B108.4
C17—C18—H18B108.8H51A—C51—H51B107.5
C19—C18—H18B108.8C53—C52—C51113.8 (4)
H18A—C18—H18B107.7C53—C52—H52A108.8
C20—C19—C18113.8 (4)C51—C52—H52A108.8
C20—C19—H19A108.8C53—C52—H52B108.8
C18—C19—H19A108.8C51—C52—H52B108.8
C20—C19—H19B108.8H52A—C52—H52B107.7
C18—C19—H19B108.8C52—C53—C54117.3 (4)
H19A—C19—H19B107.7C52—C53—H53A108.0
C21—C20—C19114.2 (4)C54—C53—H53A108.0
C21—C20—H20A108.7C52—C53—H53B108.0
C19—C20—H20A108.7C54—C53—H53B108.0
C21—C20—H20B108.7H53A—C53—H53B107.2
C19—C20—H20B108.7C55—C54—C53113.3 (3)
H20A—C20—H20B107.6C55—C54—H54A108.9
C20—C21—C22114.1 (4)C53—C54—H54A108.9
C20—C21—H21A108.7C55—C54—H54B108.9
C22—C21—H21A108.7C53—C54—H54B108.9
C20—C21—H21B108.7H54A—C54—H54B107.7
C22—C21—H21B108.7C54—C55—C56117.0 (3)
H21A—C21—H21B107.6C54—C55—H55A108.0
C23—C22—C21115.1 (4)C56—C55—H55A108.0
C23—C22—H22A108.5C54—C55—H55B108.0
C21—C22—H22A108.5C56—C55—H55B108.0
C23—C22—H22B108.5H55A—C55—H55B107.3
C21—C22—H22B108.5C57—C56—C55110.2 (3)
H22A—C22—H22B107.5C57—C56—H56A109.6
C22—C23—C24114.5 (4)C55—C56—H56A109.6
C22—C23—H23A108.6C57—C56—H56B109.6
C24—C23—H23A108.6C55—C56—H56B109.6
C22—C23—H23B108.6H56A—C56—H56B108.1
C24—C23—H23B108.6C56—C57—N2117.7 (3)
H23A—C23—H23B107.6C56—C57—H57A107.9
C23—C24—C25114.2 (3)N2—C57—H57A107.9
C23—C24—H24A108.7C56—C57—H57B107.9
C25—C24—H24A108.7N2—C57—H57B107.9
C23—C24—H24B108.7H57A—C57—H57B107.2
C25—C24—H24B108.7N2—C58—H58A109.5
H24A—C24—H24B107.6N2—C58—H58B109.5
C24—C25—C26114.3 (3)H58A—C58—H58B109.5
C24—C25—H25A108.7N2—C58—H58C109.5
C26—C25—H25A108.7H58A—C58—H58C109.5
C24—C25—H25B108.7H58B—C58—H58C109.5
C26—C25—H25B108.7N2—C59—H59A109.5
H25A—C25—H25B107.6N2—C59—H59B109.5
C27—C26—C25113.0 (3)H59A—C59—H59B109.5
C27—C26—H26A109.0N2—C59—H59C109.5
C25—C26—H26A109.0H59A—C59—H59C109.5
C27—C26—H26B109.0H59B—C59—H59C109.5
C25—C26—H26B109.0C61—C60—N2113.9 (3)
H26A—C26—H26B107.8C61—C60—H60A108.8
C28—C27—C26114.1 (3)N2—C60—H60A108.8
C28—C27—H27A108.7C61—C60—H60B108.8
C26—C27—H27A108.7N2—C60—H60B108.8
C28—C27—H27B108.7H60A—C60—H60B107.7
C26—C27—H27B108.7C62—C61—C66119.0 (4)
H27A—C27—H27B107.6C62—C61—C60120.9 (4)
C27—C28—C29113.6 (3)C66—C61—C60120.0 (4)
C27—C28—H28A108.8C61—C62—C63120.3 (4)
C29—C28—H28A108.8C61—C62—H62119.9
C27—C28—H28B108.8C63—C62—H62119.9
C29—C28—H28B108.8C64—C63—C62121.1 (5)
H28A—C28—H28B107.7C64—C63—H63119.4
C30—C29—C28110.3 (3)C62—C63—H63119.4
C30—C29—H29A109.6C63—C64—C65119.4 (4)
C28—C29—H29A109.6C63—C64—H64120.3
C30—C29—H29B109.6C65—C64—H64120.3
C28—C29—H29B109.6C64—C65—C66119.5 (4)
H29A—C29—H29B108.1C64—C65—H65120.3
C29—C30—N1117.5 (3)C66—C65—H65120.3
C29—C30—H30A107.9C61—C66—C65120.7 (4)
N1—C30—H30A107.9C61—C66—H66119.7
C29—C30—H30B107.9C65—C66—H66119.7
N1—C30—H30B107.9C32—N1—C31108.8 (3)
H30A—C30—H30B107.2C32—N1—C33111.6 (3)
N1—C31—H31A109.5C31—N1—C33109.7 (3)
N1—C31—H31B109.5C32—N1—C30110.6 (3)
H31A—C31—H31B109.5C31—N1—C30110.7 (3)
N1—C31—H31C109.5C33—N1—C30105.4 (3)
H31A—C31—H31C109.5C58—N2—C59108.4 (3)
H31B—C31—H31C109.5C58—N2—C60111.4 (3)
N1—C32—H32A109.5C59—N2—C60110.1 (3)
N1—C32—H32B109.5C58—N2—C57110.6 (3)
H32A—C32—H32B109.5C59—N2—C57106.4 (3)
N1—C32—H32C109.5C60—N2—C57109.8 (3)
S2—Ni1—S1—C12.25 (13)S16—C10—C11—S171.5 (5)
S7—Ni1—S1—C1179.83 (13)S19—C10—C11—S17178.6 (2)
S6—Ni1—S1—C118.6 (16)S16—C10—C11—S18176.4 (2)
S7—Ni1—S2—C2123.9 (9)S19—C10—C11—S183.5 (4)
S6—Ni1—S2—C2178.06 (14)Ni2—S17—C11—C101.0 (4)
S1—Ni1—S2—C22.43 (14)Ni2—S17—C11—S18176.8 (2)
S2—Ni1—S6—C4175.20 (13)C12—S18—C11—C101.1 (4)
S7—Ni1—S6—C42.38 (13)C12—S18—C11—S17178.9 (3)
S1—Ni1—S6—C4158.8 (15)C10—S19—C12—S20176.4 (3)
S2—Ni1—S7—C556.2 (9)C10—S19—C12—S183.2 (3)
S6—Ni1—S7—C51.60 (13)C11—S18—C12—S20177.8 (3)
S1—Ni1—S7—C5177.85 (13)C11—S18—C12—S191.7 (3)
S12—Ni2—S11—C72.06 (14)C13—C14—C15—C16180.0 (4)
S17—Ni2—S11—C7176.71 (14)C14—C15—C16—C17179.4 (4)
S16—Ni2—S11—C797.1 (16)C15—C16—C17—C18179.7 (4)
S11—Ni2—S12—C81.66 (14)C16—C17—C18—C19179.1 (4)
S17—Ni2—S12—C872 (2)C17—C18—C19—C20178.8 (4)
S16—Ni2—S12—C8180.00 (13)C18—C19—C20—C21177.9 (4)
S11—Ni2—S16—C1085.7 (16)C19—C20—C21—C22178.2 (4)
S12—Ni2—S16—C10179.14 (14)C20—C21—C22—C23175.6 (4)
S17—Ni2—S16—C100.37 (14)C21—C22—C23—C24179.6 (4)
S11—Ni2—S17—C11178.54 (14)C22—C23—C24—C25178.3 (4)
S12—Ni2—S17—C11107 (2)C23—C24—C25—C26176.8 (4)
S16—Ni2—S17—C110.21 (14)C24—C25—C26—C27176.5 (4)
Ni1—S1—C1—C21.6 (3)C25—C26—C27—C28176.4 (4)
Ni1—S1—C1—S4178.90 (19)C26—C27—C28—C29175.0 (4)
C3—S4—C1—C20.1 (3)C27—C28—C29—C30178.2 (3)
C3—S4—C1—S1179.5 (2)C28—C29—C30—N1176.8 (3)
S1—C1—C2—S20.4 (5)N1—C33—C34—C3589.3 (5)
S4—C1—C2—S2179.1 (2)N1—C33—C34—C3995.5 (4)
S1—C1—C2—S3179.56 (19)C39—C34—C35—C360.5 (6)
S4—C1—C2—S30.0 (4)C33—C34—C35—C36175.9 (4)
Ni1—S2—C2—C12.2 (4)C34—C35—C36—C370.6 (7)
Ni1—S2—C2—S3178.7 (2)C35—C36—C37—C380.4 (7)
C3—S3—C2—C10.1 (3)C36—C37—C38—C390.8 (7)
C3—S3—C2—S2179.0 (2)C35—C34—C39—C381.7 (6)
C2—S3—C3—S5179.0 (3)C33—C34—C39—C38177.0 (4)
C2—S3—C3—S40.1 (2)C37—C38—C39—C341.9 (6)
C1—S4—C3—S5179.0 (3)C40—C41—C42—C43178.7 (4)
C1—S4—C3—S30.1 (2)C41—C42—C43—C44179.5 (4)
Ni1—S6—C4—C53.0 (3)C42—C43—C44—C45179.3 (4)
Ni1—S6—C4—S9177.27 (19)C43—C44—C45—C46180.0 (4)
C6—S9—C4—C50.0 (3)C44—C45—C46—C47178.7 (4)
C6—S9—C4—S6179.7 (2)C45—C46—C47—C48179.1 (4)
S6—C4—C5—S72.1 (5)C46—C47—C48—C49177.2 (4)
S9—C4—C5—S7178.22 (19)C47—C48—C49—C50178.8 (4)
S6—C4—C5—S8178.40 (19)C48—C49—C50—C51176.7 (4)
S9—C4—C5—S81.3 (4)C49—C50—C51—C52179.5 (4)
Ni1—S7—C5—C40.1 (3)C50—C51—C52—C53179.5 (4)
Ni1—S7—C5—S8179.34 (19)C51—C52—C53—C54174.1 (4)
C6—S8—C5—C41.9 (3)C52—C53—C54—C55179.9 (4)
C6—S8—C5—S7177.6 (2)C53—C54—C55—C56174.6 (4)
C5—S8—C6—S10176.4 (3)C54—C55—C56—C57169.8 (4)
C5—S8—C6—S91.9 (2)C55—C56—C57—N2151.0 (4)
C4—S9—C6—S10177.0 (3)N2—C60—C61—C6285.7 (4)
C4—S9—C6—S81.3 (2)N2—C60—C61—C6693.6 (4)
Ni2—S11—C7—C82.2 (4)C66—C61—C62—C632.0 (6)
Ni2—S11—C7—S14179.5 (2)C60—C61—C62—C63177.3 (4)
C9—S14—C7—C82.6 (4)C61—C62—C63—C641.0 (6)
C9—S14—C7—S11175.8 (3)C62—C63—C64—C650.3 (7)
S11—C7—C8—S121.0 (5)C63—C64—C65—C660.6 (6)
S14—C7—C8—S12179.5 (2)C62—C61—C66—C651.8 (6)
S11—C7—C8—S13176.1 (2)C60—C61—C66—C65177.6 (3)
S14—C7—C8—S132.3 (4)C64—C65—C66—C610.5 (6)
Ni2—S12—C8—C70.8 (4)C34—C33—N1—C3255.3 (4)
Ni2—S12—C8—S13177.7 (2)C34—C33—N1—C3165.4 (4)
C9—S13—C8—C70.8 (4)C34—C33—N1—C30175.4 (3)
C9—S13—C8—S12177.9 (2)C29—C30—N1—C3259.1 (4)
C7—S14—C9—S15176.7 (3)C29—C30—N1—C3161.6 (4)
C7—S14—C9—S132.0 (3)C29—C30—N1—C33179.9 (3)
C8—S13—C9—S15177.7 (3)C61—C60—N2—C5863.5 (4)
C8—S13—C9—S141.0 (3)C61—C60—N2—C5956.9 (4)
Ni2—S16—C10—C111.1 (4)C61—C60—N2—C57173.7 (3)
Ni2—S16—C10—S19179.0 (2)C56—C57—N2—C5870.8 (5)
C12—S19—C10—C114.1 (3)C56—C57—N2—C59171.6 (4)
C12—S19—C10—S16175.8 (2)C56—C57—N2—C6052.5 (5)

Experimental details

Crystal data
Chemical formula(C27H50N)[Ni(C3S5)2]
Mr840.05
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)12.1626 (16), 12.2384 (16), 27.778 (4)
α, β, γ (°)80.388 (2), 84.699 (2), 87.431 (2)
V3)4057.4 (9)
Z4
Radiation typeMo Kα
µ (mm1)1.02
Crystal size (mm)0.26 × 0.14 × 0.12
Data collection
DiffractometerBruker SMART APEX CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.778, 0.888
No. of measured, independent and
observed [I > 2σ(I)] reflections
32319, 15041, 8322
Rint0.047
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.128, 1.01
No. of reflections15041
No. of parameters817
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.36, 0.32

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top
Ni1—S22.1516 (10)Ni2—S112.1504 (11)
Ni1—S72.1607 (10)Ni2—S122.1591 (11)
Ni1—S62.1631 (10)Ni2—S172.1605 (11)
Ni1—S12.1657 (10)Ni2—S162.1615 (10)
 

Acknowledgements

This work was supported by the Key Project of the Chinese Ministry of Education (No. 210102).

References

First citationBruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationCassoux, P. (1999). Coord. Chem. Rev. 185–186, 213–232.  Web of Science CrossRef CAS Google Scholar
First citationCassoux, P., Valade, L., Kobayashi, H., Kobayashi, A., Clark, R. A. & Underhill, A. (1991). Coord. Chem. Rev. 110, 115–160.  CrossRef CAS Web of Science Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationXue, G., Xu, W., Yu, W.-T. & Fang, Q. (2003). Acta Cryst. C59, m27–m29.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar

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