Download citation
Download citation
link to html
The title compound, (C7H10N)[Ni(C3S5)2] or (Etpy)[Ni(dmit)2] (where Etpy is the N-ethyl­pyridinium cation, C7H10N+, and dmit is the 2-thio­xo-1,3-di­thiole-4,5-di­thiol­ate dianion, C3S52−), crystallizes in the P\overline 1 space group with two mol­ecules in the asymmetric unit. The [Ni(dmit)2] monoanion has a planar D2h conformation, with the central Ni atom and the four coordinated S atoms forming an NiS4 square plane. The six-membered ring of the Etpy cation also shows good planarity, as expected. There are two main types of disorder in the two Etpy cations. Several short intermolecular interactions are present, such as S...S, Ni...S and Ni...Ni, which help to form the enhanced three-dimensional structure of the crystal.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270102020115/gg1142sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270102020115/gg1142Isup2.hkl
Contains datablock I

CCDC reference: 204032

Comment top

Metal-dmit coordination anions, [M(dmit)2]x- (0 x 1), as the conducting component in the Z[M(dmit)2]n type of molecular conductors and superconductors, have attracted intense research interest over the past 20 years (Lindqvist et al., 1979; Valade et al., 1985; Bousseau et al., 1986; Kobayashi et al., 1987; Cornelissen et al., 1991; Miyazaki et al., 1992; Tajima et al., 1993; Veldhuizen et al., 1995; Fun et al., 1996; Xu et al., 2001). Various crystals, and consequently various conductivities, can be obtained by using different monocations in the 1:2 salts of Z[Ni(dmit)2]2, which has formed the most dominant group in the Z[M(dmit)2]n family. From the synthesis point of view, conductive 1:2 Z[Ni(dmit)2]2 salts are prepared from the non-conductive precursor of 1:1 Z[Ni(dmit)2] salts. To date, most cations have been tetraalkyl ammonium, and less attention has been paid to planar cations. The synthesis of [guanidinium][Ni(dmit)2]2 (Veldhuizen et al., 1995) has aroused our interest in such small planar cations, such as N-ethylpyridinine, because small planar cations may reduce the spacing between the conductive anions and enhance the overlap between molecular orbitals. Thus, we synthesized the title 1:1 complex, (I), as a precursor of the 1:2 complex [Etpy][Ni(dmit)2]2, which we failed to obtain, and report its structure in this paper. Surprisingly, even the 1:1 title complex shows considerable conductivity. \sch

The unit cell of (I) contains two crystallographically independent [Ni(dmit)2] anions and two Etpy cations, as depicted in Figs. 1 and 2. Statistically speaking, there are no significant differences in the bond lengths and angles between the two [Ni(dmit)2] anions, except that the planarity of [Ni2(dmit)2] is more perfect than that of [Ni1(dmit)2]. Both of the [Ni(dmit)2] anions have a D2 h symmetrical conformation and exhibit perfect planarity, with maximum deviations from the least-squares plane of 0.078 (1) Å for atom S10 in [Ni1(dmit)2] and 0.055 (1) Å for atom S18 in [Ni2(dmit)2]. The NiS4 core adopts a slightly distorted square-planar conformation. The Ni—S bond lengths range from 2.1535 (13) to 2.1751 (13) Å, with the average length being 2.1604 (13) Å, and S—Ni—S angles range from 86.65 (5) to 93.09 (5)°. The Etpy ring is also planar, as expected. There are two types of disorder in the two Etpy cations. One type affects all four C atoms (C22, C23, C24 and C25) in one Etpy ring, with occupancies of 0.55 (2) and 0.45 (2), and the other affects atom C14 in the ethyl group of another Etpy cation, with occupancies of 0.648 (19) and 0.352 (19).

There are many S···S, Ni···S and Ni···Ni interactions between neighbouring molecules of (I) (Figs. 2 and 3). Table 2 lists all the intermolecular S···S contacts shorter than 3.60 Å (the sum of the van der Waals radii), Ni···S contacts shorter than 4.10 Å and Ni···Ni contacts shorter than 4.60 Å. The shortest intermolecular S···S contact is 3.383 (2) Å, between atoms S17 and S17? [symmetry code?], which is shorter than the shortest value reported in the literature (Cornelissen et al., 1991).

Referring to Figs. 2 and 3 and Table 2, the anions of (I) form weak dimers via Ni···S and Ni···Ni interactions. The angle between the planes of two independent anions is 2.99 (4)°, showing the basic parallel arrangement of the two anions; the two long axes of the two planar anions are also parallel. In fact, all planar [Ni(dmit)2] anions are parallel to each other. The anions form a kind of zigzag chain via five pairs of strong intermolecular S···S interactions between neighbouring [Ni(dmit)2] anions. Thus, (I) shows the typical characteristic of one-dimensional structure required for conductivity.

Additionally, the structure of (I) exhibits a slight two- or three-dimensional feature, due to Ni···Ni dimer interactions, terminal S···S interactions and anionic-cationic coulombic interactions. The Etpy cations are located between the anionic zigzag chains. This kind of crystal, with strong intermolecular interactions, may have a high conductivity. In fact, the measured conductivity (by the two-probe contact method) of the crystal of (I) is 5 × 10−7 S cm−1 at room temperature, which is quite high among the Z[M(dmit)2] type of 1:1 complexes.

Table 2 Intermolecular S···S, Ni···S and Ni···Ni contacts (Å) shorter than the van der Waals radii

Experimental top

Ethyl iodide (15 ml) was mixed with pyridine (24 ml) and then kept at 339–341 K for several hours. The resulting solution was washed with a large excess of petroleum ether until white N-ethylpyridine iodide precipitated. Dmit(COPh)2 (0.816 g, 2 mmol) was treated with an excess of sodium methylate (0.5M) in MeOH (20 ml) under nitrogen at room temperature with stirring. To the resulting red solution, NiCl2·6H2O (0.237 g, 1 mmol) in MeOH (20 ml) and N-ethylpyridine iodide (0.550 g, 2.4 mmol) in MeOH (20 ml) were added. The resulting precipitate was washed with MeOH (yield 0.555 g). This precipitate was then dissolved in acetone and oxidated by I2/NaI. Thick black platelets of (I), one of which was used for the present structure determination, could be obtained from the filtrate by slow evaporation (m.p. 470 K). The crystal could be further purified by recrystallization from acetone in air.

Refinement top

After checking their presence in the difference map, all H atoms were geometrically fixed and allowed to ride on their attached atoms, with C—H distances in the range 0.93–0.97 Å and Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL.

Figures top
[Figure 1] Fig. 1. A view of the two independent cations and anions of (I), with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. The crystal packing of (I), viewed along the a axis.
[Figure 3] Fig. 3. The packing of the [Ni(dmit)2] anion of (I).
N-ethylpyridinium bis(2-thioxo-1,3-dithiole-4,5-dithiolato)nickelate(II) top
Crystal data top
[C7H10N][Ni(C3S5)2]Z = 4
Mr = 559.61F(000) = 1132
Triclinic, P1Dx = 1.792 Mg m3
Hall symbol: -P1Melting point: 470 K
a = 8.7825 (8) ÅMo Kα radiation, λ = 0.71073 Å
b = 16.209 (2) ÅCell parameters from 36 reflections
c = 16.7077 (16) Åθ = 5.3–12.4°
α = 112.555 (9)°µ = 1.94 mm1
β = 104.477 (7)°T = 293 K
γ = 95.876 (10)°Prism, black
V = 2073.8 (4) Å30.24 × 0.22 × 0.20 mm
Data collection top
Bruker P4
diffractometer
4722 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.024
Graphite monochromatorθmax = 25.0°, θmin = 2.4°
θ/2θ scansh = 110
Absorption correction: ψ scan
(XSCANS; Siemens, 1996)
k = 1717
Tmin = 0.566, Tmax = 0.678l = 1919
8565 measured reflections3 standard reflections every 97 reflections
7056 independent reflections intensity decay: 2%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.118 w = 1/[σ2(Fo2) + (0.0509P)2 + 2.0853P]
where P = (Fo2 + 2Fc2)/3
S = 0.95(Δ/σ)max = 0.001
7056 reflectionsΔρmax = 0.55 e Å3
449 parametersΔρmin = 0.40 e Å3
11 restraintsExtinction correction: SHELXTL (Bruker, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00173 (19)
Crystal data top
[C7H10N][Ni(C3S5)2]γ = 95.876 (10)°
Mr = 559.61V = 2073.8 (4) Å3
Triclinic, P1Z = 4
a = 8.7825 (8) ÅMo Kα radiation
b = 16.209 (2) ŵ = 1.94 mm1
c = 16.7077 (16) ÅT = 293 K
α = 112.555 (9)°0.24 × 0.22 × 0.20 mm
β = 104.477 (7)°
Data collection top
Bruker P4
diffractometer
4722 reflections with I > 2σ(I)
Absorption correction: ψ scan
(XSCANS; Siemens, 1996)
Rint = 0.024
Tmin = 0.566, Tmax = 0.6783 standard reflections every 97 reflections
8565 measured reflections intensity decay: 2%
7056 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04311 restraints
wR(F2) = 0.118H-atom parameters constrained
S = 0.95Δρmax = 0.55 e Å3
7056 reflectionsΔρmin = 0.40 e Å3
449 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*/UeqOcc. (<1)
Ni10.44569 (7)0.11278 (4)0.07908 (4)0.04380 (17)
Ni20.13204 (6)0.47959 (4)0.41612 (4)0.04227 (17)
S10.0926 (2)0.29906 (10)0.08577 (12)0.0791 (5)
S20.07027 (15)0.15109 (9)0.02304 (10)0.0627 (4)
S30.36857 (17)0.14206 (9)0.15004 (9)0.0620 (4)
S40.20784 (14)0.02452 (8)0.01498 (9)0.0557 (3)
S50.53062 (15)0.03354 (9)0.15274 (9)0.0600 (3)
S60.35915 (14)0.19539 (9)0.00852 (9)0.0561 (3)
S70.68467 (14)0.19928 (8)0.14317 (9)0.0527 (3)
S80.52845 (15)0.37205 (9)0.01430 (9)0.0595 (3)
S90.82505 (15)0.37524 (8)0.13826 (9)0.0575 (3)
S100.8120 (2)0.52678 (10)0.08163 (11)0.0790 (5)
S110.24903 (19)0.08352 (9)0.43960 (11)0.0733 (4)
S120.25584 (16)0.22509 (9)0.36852 (9)0.0616 (4)
S130.04297 (16)0.22650 (9)0.48967 (10)0.0617 (4)
S140.10791 (14)0.39424 (8)0.35476 (9)0.0561 (3)
S150.21771 (14)0.39629 (9)0.48552 (9)0.0574 (3)
S160.04955 (14)0.55996 (8)0.34293 (9)0.0554 (3)
S170.37140 (14)0.56555 (8)0.47898 (9)0.0558 (3)
S180.22611 (16)0.72704 (9)0.33556 (9)0.0580 (3)
S190.51998 (15)0.73448 (8)0.46417 (10)0.0599 (4)
S200.51421 (19)0.87549 (10)0.39244 (12)0.0795 (5)
N10.0079 (8)0.0472 (4)0.2979 (5)0.0947 (18)
N20.3953 (8)0.4319 (4)0.2320 (4)0.0866 (16)
C10.1732 (6)0.2023 (3)0.0862 (3)0.0558 (12)
C20.2270 (5)0.0579 (3)0.0549 (3)0.0462 (11)
C30.3659 (6)0.0542 (3)0.1142 (3)0.0459 (11)
C40.5273 (5)0.2813 (3)0.0461 (3)0.0461 (11)
C50.6674 (5)0.2830 (3)0.1043 (3)0.0447 (10)
C60.7257 (6)0.4291 (3)0.0773 (3)0.0548 (12)
C70.1587 (6)0.1736 (3)0.4329 (3)0.0528 (12)
C80.0940 (5)0.3126 (3)0.3959 (3)0.0466 (11)
C90.0480 (6)0.3140 (3)0.4526 (3)0.0495 (11)
C100.2187 (5)0.6429 (3)0.3755 (3)0.0431 (10)
C110.3578 (5)0.6454 (3)0.4355 (3)0.0437 (10)
C120.4229 (6)0.7837 (3)0.3974 (3)0.0535 (12)
C130.1734 (9)0.2026 (5)0.2393 (5)0.125 (3)
H13A0.27620.22980.23880.188*
H13B0.10160.24340.23990.188*
H13C0.18680.19160.18570.188*
C140.1051 (16)0.1150 (8)0.3215 (9)0.103 (5)*0.648 (19)
H14A0.03510.12500.37030.123*0.648 (19)
H14B0.19120.08980.34200.123*0.648 (19)
C14'0.1809 (16)0.1029 (7)0.2715 (16)0.088 (8)*0.352 (19)
H14C0.21980.08380.32390.105*0.352 (19)
H14D0.25360.09330.22330.105*0.352 (19)
C150.0526 (10)0.0070 (6)0.2429 (6)0.123 (3)
H15A0.16070.02040.20890.147*
C160.0503 (15)0.0508 (7)0.2352 (5)0.126 (3)
H16A0.01490.07920.19730.151*
C170.2059 (12)0.0694 (5)0.2815 (7)0.108 (3)
H17A0.28040.10890.27430.129*
C180.2539 (9)0.0313 (5)0.3377 (6)0.111 (3)
H18A0.36200.04500.37180.133*
C190.1461 (12)0.0270 (6)0.3453 (5)0.108 (2)
H19A0.18010.05390.38480.130*
C200.2410 (12)0.2967 (7)0.2333 (7)0.191 (5)
H20A0.24510.24810.25260.286*
H20B0.19840.27120.16800.286*
H20C0.17270.33410.25960.286*
C210.4016 (11)0.3520 (6)0.2632 (6)0.145 (4)
H21A0.47110.31430.23710.175*
H21B0.44560.37720.32920.175*
C220.2846 (18)0.4593 (13)0.1830 (11)0.080 (5)*0.45 (2)
H22B0.17970.42440.15890.096*0.45 (2)
C230.311 (2)0.5339 (13)0.1650 (11)0.071 (5)*0.45 (2)
H23B0.23010.54790.12770.085*0.45 (2)
C240.471 (2)0.5890 (10)0.2071 (11)0.069 (5)*0.45 (2)
H24B0.49510.64170.19840.083*0.45 (2)
C250.580 (3)0.5684 (10)0.2552 (14)0.088 (6)*0.45 (2)
H25B0.68560.60310.28090.106*0.45 (2)
C22'0.2626 (15)0.4234 (14)0.1729 (9)0.097 (5)*0.55 (2)
H22A0.17550.37380.14800.117*0.55 (2)
C23'0.2649 (15)0.4928 (11)0.1520 (8)0.079 (4)*0.55 (2)
H23A0.16830.49210.11270.094*0.55 (2)
C24'0.386 (2)0.5662 (8)0.1785 (9)0.073 (4)*0.55 (2)
H24A0.37740.61320.15990.087*0.55 (2)
C25'0.524 (2)0.5617 (11)0.2366 (12)0.112 (7)*0.55 (2)
H25A0.61480.60800.25670.134*0.55 (2)
C260.5384 (9)0.4946 (5)0.2676 (4)0.099 (2)
H26A0.62000.48360.30730.119*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0387 (3)0.0409 (3)0.0527 (4)0.0023 (3)0.0127 (3)0.0235 (3)
Ni20.0398 (3)0.0372 (3)0.0524 (3)0.0023 (2)0.0125 (3)0.0245 (3)
S10.0956 (11)0.0564 (9)0.1104 (12)0.0103 (8)0.0477 (10)0.0533 (9)
S20.0469 (7)0.0519 (7)0.0944 (10)0.0006 (6)0.0152 (7)0.0435 (7)
S30.0696 (9)0.0562 (8)0.0710 (9)0.0145 (7)0.0173 (7)0.0408 (7)
S40.0415 (7)0.0531 (7)0.0761 (8)0.0000 (6)0.0061 (6)0.0416 (7)
S50.0459 (7)0.0543 (7)0.0750 (9)0.0002 (6)0.0005 (6)0.0368 (7)
S60.0416 (6)0.0601 (8)0.0684 (8)0.0018 (6)0.0060 (6)0.0393 (7)
S70.0415 (6)0.0478 (7)0.0682 (8)0.0006 (5)0.0061 (6)0.0336 (6)
S80.0559 (8)0.0602 (8)0.0740 (9)0.0090 (6)0.0160 (7)0.0440 (7)
S90.0492 (7)0.0531 (7)0.0682 (8)0.0063 (6)0.0082 (6)0.0345 (6)
S100.0857 (11)0.0584 (9)0.1032 (12)0.0014 (8)0.0260 (9)0.0516 (9)
S110.0860 (10)0.0492 (8)0.0923 (10)0.0058 (7)0.0388 (9)0.0365 (7)
S120.0565 (8)0.0569 (8)0.0669 (8)0.0121 (6)0.0112 (7)0.0328 (7)
S130.0591 (8)0.0549 (8)0.0869 (9)0.0059 (6)0.0226 (7)0.0483 (7)
S140.0435 (7)0.0556 (7)0.0697 (8)0.0041 (6)0.0043 (6)0.0392 (7)
S150.0421 (7)0.0565 (7)0.0791 (9)0.0034 (6)0.0069 (6)0.0456 (7)
S160.0462 (7)0.0486 (7)0.0691 (8)0.0012 (6)0.0037 (6)0.0345 (6)
S170.0429 (7)0.0497 (7)0.0784 (9)0.0025 (5)0.0034 (6)0.0437 (7)
S180.0630 (8)0.0525 (7)0.0708 (8)0.0100 (6)0.0168 (7)0.0420 (7)
S190.0473 (7)0.0511 (7)0.0896 (9)0.0001 (6)0.0136 (7)0.0459 (7)
S200.0774 (10)0.0688 (9)0.1244 (13)0.0097 (8)0.0400 (9)0.0704 (10)
N10.098 (5)0.068 (3)0.131 (5)0.021 (3)0.068 (4)0.036 (4)
N20.119 (5)0.095 (4)0.072 (3)0.053 (4)0.051 (4)0.041 (3)
C10.065 (3)0.046 (3)0.068 (3)0.015 (2)0.030 (3)0.029 (2)
C20.042 (3)0.040 (2)0.065 (3)0.005 (2)0.021 (2)0.030 (2)
C30.052 (3)0.036 (2)0.059 (3)0.010 (2)0.022 (2)0.026 (2)
C40.047 (3)0.049 (3)0.050 (3)0.009 (2)0.019 (2)0.028 (2)
C50.040 (2)0.041 (2)0.053 (3)0.001 (2)0.017 (2)0.021 (2)
C60.060 (3)0.047 (3)0.058 (3)0.004 (2)0.017 (2)0.025 (2)
C70.059 (3)0.042 (3)0.058 (3)0.000 (2)0.028 (2)0.019 (2)
C80.045 (3)0.042 (2)0.052 (3)0.002 (2)0.017 (2)0.022 (2)
C90.053 (3)0.045 (3)0.062 (3)0.009 (2)0.024 (2)0.031 (2)
C100.049 (3)0.035 (2)0.051 (3)0.007 (2)0.017 (2)0.025 (2)
C110.041 (2)0.034 (2)0.057 (3)0.0004 (19)0.014 (2)0.024 (2)
C120.057 (3)0.050 (3)0.071 (3)0.014 (2)0.030 (3)0.037 (2)
C130.095 (5)0.109 (6)0.156 (8)0.010 (5)0.032 (5)0.049 (6)
C150.079 (5)0.108 (7)0.138 (8)0.018 (5)0.012 (5)0.037 (6)
C160.171 (10)0.135 (8)0.075 (5)0.044 (8)0.016 (6)0.062 (5)
C170.130 (7)0.079 (5)0.142 (8)0.029 (5)0.079 (6)0.052 (5)
C180.069 (5)0.080 (5)0.139 (7)0.016 (4)0.007 (4)0.026 (5)
C190.132 (7)0.101 (6)0.094 (5)0.038 (6)0.013 (5)0.055 (5)
C200.185 (11)0.175 (11)0.155 (9)0.018 (9)0.095 (9)0.008 (8)
C210.143 (9)0.176 (10)0.097 (6)0.075 (8)0.041 (6)0.025 (6)
C260.079 (5)0.134 (7)0.062 (4)0.046 (5)0.004 (4)0.023 (4)
Geometric parameters (Å, º) top
Ni1—S72.1540 (13)C4—C51.354 (6)
Ni1—S42.1567 (13)C8—C91.356 (6)
Ni1—S52.1612 (13)C10—C111.358 (6)
Ni1—S62.1751 (13)C13—C141.476 (12)
Ni2—S172.1535 (13)C13—C14'1.509 (9)
Ni2—S142.1542 (13)C13—H13A0.9600
Ni2—S162.1657 (13)C13—H13B0.9600
Ni2—S152.1693 (13)C13—H13C0.9600
S1—C11.650 (5)C14—H14A0.9700
S2—C11.722 (5)C14—H14B0.9700
S2—C21.746 (4)C14'—H14C0.9700
S3—C11.726 (5)C14'—H14D0.9700
S3—C31.744 (4)C15—C161.299 (11)
S4—C21.712 (4)C15—H15A0.9300
S5—C31.715 (4)C16—C171.329 (11)
S6—C41.719 (4)C16—H16A0.9300
S7—C51.719 (4)C17—C181.320 (10)
S8—C61.726 (5)C17—H17A0.9300
S8—C41.746 (4)C18—C191.331 (10)
S9—C61.719 (5)C18—H18A0.9300
S9—C51.735 (4)C19—H19A0.9300
S10—C61.651 (5)C20—C211.445 (8)
S11—C71.646 (4)C20—H20A0.9600
S12—C71.719 (5)C20—H20B0.9600
S12—C81.734 (4)C20—H20C0.9600
S13—C71.731 (5)C21—H21A0.9700
S13—C91.754 (4)C21—H21B0.9700
S14—C81.712 (4)C22—C231.365 (10)
S15—C91.709 (5)C22—H22B0.9300
S16—C101.713 (4)C23—C241.43 (2)
S17—C111.711 (4)C23—H23B0.9300
S18—C121.718 (5)C24—C251.25 (2)
S18—C101.736 (4)C24—H24B0.9300
S19—C121.719 (5)C25—C261.322 (9)
S19—C111.746 (4)C25—H25B0.9300
S20—C121.658 (4)C22'—C23'1.30 (2)
N1—C151.325 (10)C22'—H22A0.9300
N1—C191.319 (9)C23'—C24'1.359 (9)
N1—C141.549 (12)C23'—H23A0.9300
N1—C14'1.548 (9)C24'—C25'1.377 (10)
N2—C22'1.281 (9)C24'—H24A0.9300
N2—C221.336 (9)C25'—C261.375 (9)
N2—C261.367 (8)C25'—H25A0.9300
N2—C211.571 (7)C26—H26A0.9300
C2—C31.344 (6)
S1···S10i3.520 (3)S15···S17iv3.4566 (19)
S2···S4ii3.439 (2)S15···S19iv3.450 (2)
S4···S4ii3.5209 (19)S17···S17iv3.383 (2)
S7···S12iii3.5195 (19)Ni1···S5v3.7586 (15)
S7···S14iii3.582 (2)Ni2···S14vi3.6565 (15)
S9···S14iii3.4014 (19)Ni1···Ni1v3.9778 (10)
S9···S16iii3.4802 (19)Ni2···Ni2vi3.9768 (9)
S11···S20i3.467 (2)
S7—Ni1—S4179.17 (5)C14'—C13—H13A101.7
S7—Ni1—S586.65 (5)C14—C13—H13B109.5
S4—Ni1—S592.63 (5)H13A—C13—H13B109.5
S7—Ni1—S693.09 (5)C14—C13—H13C109.5
S4—Ni1—S687.63 (5)H13A—C13—H13C109.5
S5—Ni1—S6178.32 (6)H13B—C13—H13C109.5
S17—Ni2—S14179.33 (6)C13—C14—N1108.9 (8)
S17—Ni2—S1692.55 (5)C13—C14—H14A109.9
S14—Ni2—S1687.66 (5)N1—C14—H14A109.9
S17—Ni2—S1587.32 (5)C13—C14—H14B109.9
S14—Ni2—S1592.50 (5)N1—C14—H14B109.9
S16—Ni2—S15177.97 (6)H14A—C14—H14B108.3
C1—S2—C297.6 (2)C13—C14'—N1107.2 (8)
C1—S3—C397.0 (2)C13—C14'—H14C110.3
C2—S4—Ni1102.44 (15)N1—C14'—H14C110.3
C3—S5—Ni1102.34 (16)C13—C14'—H14D110.3
C4—S6—Ni1101.85 (16)N1—C14'—H14D110.3
C5—S7—Ni1102.34 (15)H14C—C14'—H14D108.5
C6—S8—C497.2 (2)C16—C15—N1121.9 (8)
C6—S9—C597.7 (2)C16—C15—H15A119.1
C7—S12—C897.7 (2)N1—C15—H15A119.1
C7—S13—C997.5 (2)C15—C16—C17120.1 (8)
C8—S14—Ni2103.14 (16)C15—C16—H16A120.0
C9—S15—Ni2102.16 (16)C17—C16—H16A120.0
C10—S16—Ni2102.78 (15)C18—C17—C16119.4 (8)
C11—S17—Ni2102.68 (15)C18—C17—H17A120.3
C12—S18—C1097.6 (2)C16—C17—H17A120.3
C12—S19—C1197.3 (2)C17—C18—C19119.5 (7)
C15—N1—C19117.8 (7)C17—C18—H18A120.3
C15—N1—C14132.1 (9)C19—C18—H18A120.3
C19—N1—C14110.1 (9)N1—C19—C18121.3 (7)
C15—N1—C14'93.4 (10)N1—C19—H19A119.4
C19—N1—C14'148.7 (11)C18—C19—H19A119.4
C22'—N2—C26131.1 (11)C21—C20—H20A109.5
C22—N2—C26108.9 (10)C21—C20—H20B109.5
C22'—N2—C21115.1 (11)H20A—C20—H20B109.5
C22—N2—C21137.4 (11)C21—C20—H20C109.5
C26—N2—C21113.6 (7)H20A—C20—H20C109.5
S1—C1—S2123.3 (3)H20B—C20—H20C109.5
S1—C1—S3123.4 (3)C20—C21—N2109.6 (8)
S2—C1—S3113.2 (3)C20—C21—H21A109.7
C3—C2—S4121.4 (3)N2—C21—H21A109.7
C3—C2—S2115.5 (3)C20—C21—H21B109.7
S4—C2—S2123.1 (3)N2—C21—H21B109.7
C2—C3—S5121.1 (3)H21A—C21—H21B108.2
C2—C3—S3116.7 (3)N2—C22—C23126.1 (14)
S5—C3—S3122.2 (3)N2—C22—H22B117.0
C5—C4—S6121.3 (3)C23—C22—H22B117.0
C5—C4—S8115.8 (3)C22—C23—C24115.6 (14)
S6—C4—S8122.9 (3)C22—C23—H23B122.2
C4—C5—S7121.4 (3)C24—C23—H23B122.2
C4—C5—S9116.0 (3)C25—C24—C23121.7 (13)
S7—C5—S9122.5 (3)C25—C24—H24B119.1
S10—C6—S9122.5 (3)C23—C24—H24B119.1
S10—C6—S8124.3 (3)C26—C25—C24116.5 (17)
S9—C6—S8113.2 (3)C26—C25—H25B121.8
S11—C7—S12123.2 (3)C24—C25—H25B121.8
S11—C7—S13123.8 (3)N2—C22'—C23'111.6 (13)
S12—C7—S13113.0 (2)N2—C22'—H22A124.2
C9—C8—S14120.3 (3)C23'—C22'—H22A124.2
C9—C8—S12116.7 (3)C24'—C23'—C22'130.2 (12)
S14—C8—S12123.0 (3)C24'—C23'—H23A114.9
C8—C9—S15121.9 (3)C22'—C23'—H23A114.9
C8—C9—S13115.0 (3)C23'—C24'—C25'110.9 (12)
S15—C9—S13123.1 (3)C23'—C24'—H24A124.6
C11—C10—S16120.4 (3)C25'—C24'—H24A124.6
C11—C10—S18115.9 (3)C24'—C25'—C26125.7 (14)
S16—C10—S18123.7 (3)C24'—C25'—H25A117.1
C10—C11—S17121.5 (3)C26—C25'—H25A117.1
C10—C11—S19115.7 (3)C25—C26—N2130.9 (13)
S17—C11—S19122.8 (3)C25'—C26—N2110.1 (10)
S20—C12—S19122.4 (3)C25—C26—H26A114.5
S20—C12—S18124.1 (3)C25'—C26—H26A135.3
S19—C12—S18113.5 (2)N2—C26—H26A114.5
C14—C13—H13A109.5
Symmetry codes: (i) x1, y1, z; (ii) x, y, z; (iii) x+1, y, z; (iv) x+1, y+1, z+1; (v) x+1, y, z; (vi) x, y+1, z+1.

Experimental details

Crystal data
Chemical formula[C7H10N][Ni(C3S5)2]
Mr559.61
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)8.7825 (8), 16.209 (2), 16.7077 (16)
α, β, γ (°)112.555 (9), 104.477 (7), 95.876 (10)
V3)2073.8 (4)
Z4
Radiation typeMo Kα
µ (mm1)1.94
Crystal size (mm)0.24 × 0.22 × 0.20
Data collection
DiffractometerBruker P4
diffractometer
Absorption correctionψ scan
(XSCANS; Siemens, 1996)
Tmin, Tmax0.566, 0.678
No. of measured, independent and
observed [I > 2σ(I)] reflections
8565, 7056, 4722
Rint0.024
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.118, 0.95
No. of reflections7056
No. of parameters449
No. of restraints11
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.55, 0.40

Computer programs: XSCANS (Siemens, 1996), XSCANS, SHELXTL (Bruker, 1997), SHELXTL.

Selected geometric parameters (Å, º) top
Ni1—S72.1540 (13)Ni2—S172.1535 (13)
Ni1—S42.1567 (13)Ni2—S142.1542 (13)
Ni1—S52.1612 (13)Ni2—S162.1657 (13)
Ni1—S62.1751 (13)Ni2—S152.1693 (13)
S1···S10i3.520 (3)S15···S17iv3.4566 (19)
S2···S4ii3.439 (2)S15···S19iv3.450 (2)
S4···S4ii3.5209 (19)S17···S17iv3.383 (2)
S7···S12iii3.5195 (19)Ni1···S5v3.7586 (15)
S7···S14iii3.582 (2)Ni2···S14vi3.6565 (15)
S9···S14iii3.4014 (19)Ni1···Ni1v3.9778 (10)
S9···S16iii3.4802 (19)Ni2···Ni2vi3.9768 (9)
S11···S20i3.467 (2)
S7—Ni1—S4179.17 (5)S17—Ni2—S14179.33 (6)
S7—Ni1—S586.65 (5)S17—Ni2—S1692.55 (5)
S4—Ni1—S592.63 (5)S14—Ni2—S1687.66 (5)
S7—Ni1—S693.09 (5)S17—Ni2—S1587.32 (5)
S4—Ni1—S687.63 (5)S14—Ni2—S1592.50 (5)
S5—Ni1—S6178.32 (6)S16—Ni2—S15177.97 (6)
Symmetry codes: (i) x1, y1, z; (ii) x, y, z; (iii) x+1, y, z; (iv) x+1, y+1, z+1; (v) x+1, y, z; (vi) x, y+1, z+1.
 

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds