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Acta Cryst. (2008). E64, m1264-m1265    [ doi:10.1107/S1600536808028663 ]

Bis(diethylenetriamine-[kappa]3N,N',N'')nickel(II) bis(1,2-dicyanoethene-1,2-dithiolato-[kappa]2S,S')nickel(II)

D.-P. Zhang, H.-L. Wang, L.-F. Zhang and Z.-H. Ni

Abstract top

The title compound, [Ni(C4H13N3)2][Ni(C4N2S2)2], has been synthesized by the reaction of Ni(ClO4)2·6H2O, diethylenetriamine (deta) and Na2[Ni(mnt)2] [mnt = maleonitriledithiolate(2-)] in methanol. The structure is composed of a [Ni(deta)2]2+ cation and a [Ni(mnt)2]2- anion. The coordination geometry of the NiII ion in the cation is slightly distorted octahedral, defined by six N atoms from two deta ligands, while the NiII ion in the anion is four-coordinated by four S atoms from two mnt ligands in a slightly distorted square-planar geometry. The cations and anions are connected by N-H...N hydrogen bonds.

Comment top

Bidentate dithiolate ligands form well square-planar complexes with nickel ions in different oxidation states. Due to their unique properties and potential applications in such areas as conducting and magnetic materials, nearinfrared dyes, nonlinear optical materials (Robertson & Cronin, 2002), the ion-pair complexes formed from [M(mnt)2]n- (M = Ni, Pd, Pt or Cu) and transition metal complex cations have been intensively studied (Bois et al., 1998; Miller et al., 1989; Ren et al., 2001). We report here a new ion-pair complex.

The title compound is composed of a [Ni(deta)2]2+ cation and a [Ni(mnt)2]2- anion [deta = diethylenetriamine; mnt = maleonitriledithiolate(2-)] (Fig. 1). In the cation, the NiII ion has a slightly distorted octahedral geometry, formed by six N atoms from two deta ligands, with the Ni—N distances in a range from 2.065 (3) to 2.164 (3) Å (Table 1), which are consistent with the corresponding values in [Ni(en)3][Ni(mnt)2] (en = ethylenediamine) (Keum et al., 1992). The NiII ion in the anion is four-coordinated by four S atoms and these five atoms form a square plane with a mean deviation of 0.161 (6) Å. The Ni—S bond lengths [2.1617 (12)–2.1739 (12) Å] are also in agreement with those found in the above complex. The cations and anions are connected by N—H···N hydrogen bonds (Table 2).

Related literature top

For related literature, see: Bois et al. (1998); Keum et al. (1992); Miller et al. (1989); Ren et al. (2001); Robertson & Cronin (2002); Simmons et al. (1962).

Experimental top

The synthesis procedure of the title compound was as following: Ni(ClO4)2.6H2O (0.037 g, 0.10 mmol) was dissolved in methanol (10 ml) at room temperature with stirring and then deta (0.021 g, 0.20 mmol) was added. A solution of Na2[Ni(mnt)2] (0.033 g, 0.10 mmol) (Simmons et al., 1962) in methanol (10 ml) was slowly added to the above solution and the mixture was stirred for another 30 min. After filtering, the filtrate was undisturbed for about two weeks at room temperature in air to produce blue crystals suitable for X-ray diffraction (yield 61.75%, 0.037 g). Analysis, calculated for C16H26N10Ni2S4: C 31.81, H 4.34, N 23.19%; found: C 31.76, H 4.31, N 23.24%.

Refinement top

H atoms bound to N atoms were found in difference Fourier maps and refined isotropically, with a restraint of N—H = 0.86 (1) Å. H atoms bound to C atoms were positioned geometrically and refined as riding atoms, with C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus (Bruker, 2007); 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. Structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.
Bis(diethylenetriamine-κ3N,N',N'')nickel(II) bis(1,2-dicyanoethene-1,2-dithiolato-κ2S,S')nickel(II) top
Crystal data top
[Ni(C4H13N3)2][Ni(C4N2S2)2]F(000) = 1248
Mr = 604.13Dx = 1.546 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3163 reflections
a = 9.589 (3) Åθ = 2.4–23.8°
b = 16.910 (5) ŵ = 1.80 mm−1
c = 16.146 (4) ÅT = 273 K
β = 97.491 (4)°Block, blue
V = 2595.8 (13) Å30.19 × 0.17 × 0.15 mm
Z = 4
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		5065 independent reflections
Radiation source: fine-focus sealed tube3393 reflections with I > 2σ(I)
graphiteRint = 0.037
φ and ω scansθmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −11→11
Tmin = 0.717, Tmax = 0.766k = −20→19
13610 measured reflectionsl = −17→19
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H atoms treated by a mixture of independent and constrained refinement
S = 0.99 w = 1/[σ2(Fo2) + (0.058P)2]
where P = (Fo2 + 2Fc2)/3
5065 reflections(Δ/σ)max < 0.001
329 parametersΔρmax = 0.86 e Å−3
10 restraintsΔρmin = −0.26 e Å−3
Crystal data top
[Ni(C4H13N3)2][Ni(C4N2S2)2]V = 2595.8 (13) Å3
Mr = 604.13Z = 4
Monoclinic, P21/nMo Kα radiation
a = 9.589 (3) ŵ = 1.80 mm−1
b = 16.910 (5) ÅT = 273 K
c = 16.146 (4) Å0.19 × 0.17 × 0.15 mm
β = 97.491 (4)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		5065 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3393 reflections with I > 2σ(I)
Tmin = 0.717, Tmax = 0.766Rint = 0.037
13610 measured reflectionsθmax = 26.0°
Refinement top
R[F2 > 2σ(F2)] = 0.041H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.109Δρmax = 0.86 e Å−3
S = 0.99Δρmin = −0.26 e Å−3
5065 reflectionsAbsolute structure: ?
329 parametersFlack parameter: ?
10 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.72467 (5)0.23459 (3)0.01993 (3)0.04722 (16)
Ni20.97276 (5)0.40148 (3)0.25321 (3)0.04194 (15)
S10.78132 (10)0.13475 (6)0.10229 (6)0.0555 (3)
S20.90403 (11)0.21706 (7)−0.04639 (7)0.0638 (3)
S30.52234 (11)0.23887 (7)0.06673 (7)0.0598 (3)
S40.68871 (10)0.34610 (6)−0.04535 (7)0.0576 (3)
N11.0808 (4)0.0021 (3)0.1686 (3)0.0828 (12)
N21.2281 (4)0.0992 (2)−0.0397 (2)0.0727 (11)
N30.1991 (4)0.3603 (3)0.0519 (3)0.0980 (15)
N40.3914 (5)0.4842 (3)−0.1113 (3)0.0902 (13)
N50.7588 (4)0.4323 (2)0.2690 (2)0.0532 (8)
N60.8844 (4)0.2901 (2)0.2388 (2)0.0573 (9)
N71.1630 (4)0.3364 (3)0.2450 (3)0.0670 (10)
N80.9396 (4)0.4370 (2)0.1246 (2)0.0551 (9)
N91.0692 (4)0.5111 (2)0.2663 (2)0.0576 (9)
N101.0222 (4)0.4021 (3)0.3870 (2)0.0552 (9)
C10.9425 (4)0.1059 (2)0.0742 (2)0.0487 (9)
C20.9942 (4)0.1410 (2)0.0098 (2)0.0498 (9)
C30.4468 (4)0.3230 (2)0.0193 (2)0.0546 (10)
C40.5168 (4)0.3686 (2)−0.0311 (2)0.0532 (10)
C51.0189 (4)0.0466 (3)0.1249 (3)0.0587 (11)
C61.1252 (4)0.1169 (3)−0.0162 (2)0.0564 (11)
C70.3083 (5)0.3441 (3)0.0363 (3)0.0676 (12)
C80.4494 (5)0.4331 (3)−0.0751 (3)0.0656 (12)
C90.6713 (4)0.3606 (3)0.2543 (3)0.0690 (12)
H9C0.63570.35640.19540.083*
H9B0.59160.36390.28540.083*
C100.7577 (5)0.2887 (3)0.2815 (3)0.0711 (13)
H10A0.78410.28940.34160.085*
H10B0.70390.24100.26680.085*
C110.9946 (5)0.2337 (3)0.2698 (3)0.0759 (14)
H11A0.96340.18020.25630.091*
H11B1.01610.23810.33010.091*
C121.1225 (6)0.2523 (3)0.2293 (3)0.0850 (16)
H12A1.19940.21810.25180.102*
H12B1.10300.24290.16960.102*
C131.0004 (5)0.5157 (3)0.1168 (3)0.0748 (13)
H13A0.94360.54500.07300.090*
H13B1.09440.51060.10130.090*
C141.0069 (5)0.5602 (3)0.1974 (3)0.0748 (13)
H14A1.06270.60780.19450.090*
H14B0.91290.57580.20660.090*
C151.0661 (5)0.5377 (3)0.3519 (3)0.0694 (12)
H15A0.97210.55560.35850.083*
H15B1.13030.58180.36390.083*
C161.1076 (5)0.4719 (3)0.4112 (2)0.0704 (13)
H16A1.20630.45950.41090.084*
H16B1.09430.48790.46740.084*
H8A0.8544 (16)0.441 (2)0.101 (2)0.051 (11)*
H8B0.971 (4)0.4005 (18)0.095 (2)0.073 (15)*
H7A1.219 (4)0.352 (3)0.211 (2)0.090 (17)*
H10C0.944 (3)0.406 (3)0.408 (3)0.091 (17)*
H5A0.727 (5)0.4692 (19)0.235 (2)0.093 (18)*
H6A0.860 (4)0.281 (2)0.1865 (8)0.055 (12)*
H7B1.217 (4)0.341 (3)0.2916 (17)0.12 (2)*
H10D1.066 (6)0.362 (3)0.409 (4)0.16 (3)*
H9A1.1581 (18)0.503 (4)0.267 (4)0.16 (3)*
H5B0.769 (5)0.448 (3)0.3200 (12)0.101 (18)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0377 (3)0.0536 (3)0.0497 (3)0.0057 (2)0.0033 (2)−0.0112 (2)
Ni20.0429 (3)0.0502 (3)0.0324 (2)−0.0003 (2)0.00373 (19)−0.0015 (2)
S10.0412 (5)0.0638 (7)0.0642 (6)0.0081 (5)0.0164 (5)−0.0001 (5)
S20.0514 (6)0.0822 (8)0.0599 (6)0.0189 (6)0.0160 (5)0.0104 (6)
S30.0503 (6)0.0652 (7)0.0663 (7)0.0126 (5)0.0161 (5)−0.0012 (5)
S40.0451 (6)0.0601 (7)0.0667 (7)0.0028 (5)0.0040 (5)−0.0026 (5)
N10.062 (2)0.098 (3)0.093 (3)0.027 (2)0.024 (2)0.027 (2)
N20.055 (2)0.110 (3)0.055 (2)0.029 (2)0.0172 (18)0.016 (2)
N30.078 (3)0.134 (4)0.089 (3)0.048 (3)0.038 (2)0.009 (3)
N40.097 (3)0.094 (3)0.077 (3)0.032 (3)0.000 (2)0.008 (2)
N50.048 (2)0.067 (2)0.044 (2)0.0015 (18)0.0033 (16)−0.0034 (19)
N60.067 (2)0.056 (2)0.047 (2)−0.0026 (18)−0.0011 (18)−0.0019 (17)
N70.055 (2)0.087 (3)0.059 (2)0.014 (2)0.008 (2)−0.003 (2)
N80.048 (2)0.077 (3)0.0393 (19)0.014 (2)0.0049 (16)0.0003 (18)
N90.065 (2)0.059 (2)0.051 (2)−0.0045 (19)0.0138 (17)−0.0004 (17)
N100.042 (2)0.087 (3)0.0367 (17)−0.009 (2)0.0043 (15)−0.0018 (18)
C10.037 (2)0.058 (3)0.051 (2)0.0068 (18)0.0077 (17)−0.0086 (19)
C20.037 (2)0.064 (3)0.049 (2)0.0069 (19)0.0053 (17)−0.0067 (19)
C30.048 (2)0.068 (3)0.047 (2)0.017 (2)0.0024 (18)−0.016 (2)
C40.050 (2)0.058 (3)0.049 (2)0.013 (2)−0.0017 (18)−0.013 (2)
C50.043 (2)0.073 (3)0.063 (3)0.007 (2)0.020 (2)0.002 (2)
C60.051 (2)0.076 (3)0.043 (2)0.016 (2)0.0078 (18)0.006 (2)
C70.064 (3)0.087 (3)0.053 (3)0.025 (3)0.014 (2)−0.003 (2)
C80.063 (3)0.077 (3)0.054 (3)0.018 (2)−0.003 (2)−0.005 (2)
C90.048 (2)0.092 (4)0.067 (3)−0.018 (3)0.006 (2)−0.014 (3)
C100.073 (3)0.070 (3)0.071 (3)−0.026 (3)0.014 (2)−0.002 (2)
C110.093 (4)0.057 (3)0.073 (3)0.009 (3)−0.009 (3)0.008 (2)
C120.096 (4)0.072 (4)0.082 (3)0.032 (3)−0.005 (3)−0.009 (3)
C130.090 (3)0.081 (4)0.056 (3)0.004 (3)0.021 (2)0.023 (2)
C140.087 (4)0.052 (3)0.085 (3)−0.001 (2)0.012 (3)0.008 (2)
C150.070 (3)0.067 (3)0.071 (3)−0.005 (2)0.010 (2)−0.028 (2)
C160.066 (3)0.100 (4)0.045 (2)−0.025 (3)0.006 (2)−0.013 (2)
Geometric parameters (Å, °) top
Ni1—S12.1739 (12)N9—C151.456 (5)
Ni1—S22.1617 (12)N9—H9A0.86 (3)
Ni1—S32.1732 (12)N10—C161.461 (5)
Ni1—S42.1658 (12)N10—H10C0.87 (3)
Ni2—N52.164 (3)N10—H10D0.85 (6)
Ni2—N62.065 (3)C1—C21.347 (5)
Ni2—N72.150 (4)C1—C51.434 (6)
Ni2—N82.145 (3)C2—C61.434 (5)
Ni2—N92.071 (4)C3—C41.359 (6)
Ni2—N102.151 (3)C3—C71.436 (5)
S1—C11.737 (4)C4—C81.412 (6)
S2—C21.738 (4)C9—C101.505 (6)
S3—C31.730 (4)C9—H9C0.9700
S4—C41.737 (4)C9—H9B0.9700
N1—C51.144 (5)C10—H10A0.9700
N2—C61.143 (5)C10—H10B0.9700
N3—C71.141 (5)C11—C121.497 (7)
N4—C81.146 (5)C11—H11A0.9700
N5—C91.477 (5)C11—H11B0.9700
N5—H5A0.86 (3)C12—H12A0.9700
N5—H5B0.86 (3)C12—H12B0.9700
N6—C111.463 (5)C13—C141.497 (6)
N6—C101.473 (5)C13—H13A0.9700
N6—H6A0.86 (2)C13—H13B0.9700
N7—C121.486 (6)C14—H14A0.9700
N7—H7A0.86 (4)C14—H14B0.9700
N7—H7B0.86 (4)C15—C161.488 (6)
N8—C131.466 (6)C15—H15A0.9700
N8—H8A0.86 (3)C15—H15B0.9700
N8—H8B0.86 (3)C16—H16A0.9700
N9—C141.453 (5)C16—H16B0.9700
S2—Ni1—S487.98 (5)C5—C1—S1117.0 (3)
S2—Ni1—S3168.77 (5)C1—C2—C6121.7 (4)
S4—Ni1—S392.72 (4)C1—C2—S2121.4 (3)
S2—Ni1—S192.58 (4)C6—C2—S2116.9 (3)
S4—Ni1—S1170.10 (4)C4—C3—C7121.0 (4)
S3—Ni1—S188.65 (4)C4—C3—S3121.4 (3)
N6—Ni2—N9177.56 (15)C7—C3—S3117.7 (3)
N6—Ni2—N898.00 (14)C3—C4—C8120.7 (4)
N9—Ni2—N881.73 (14)C3—C4—S4120.5 (3)
N6—Ni2—N782.24 (16)C8—C4—S4118.8 (3)
N9—Ni2—N795.37 (17)N1—C5—C1176.5 (5)
N8—Ni2—N795.96 (15)N2—C6—C2177.4 (4)
N6—Ni2—N1098.69 (14)N3—C7—C3178.2 (5)
N9—Ni2—N1081.72 (14)N4—C8—C4178.1 (5)
N8—Ni2—N10163.04 (16)N5—C9—C10109.7 (3)
N7—Ni2—N1089.25 (16)N5—C9—H9C109.7
N6—Ni2—N581.47 (14)C10—C9—H9C109.7
N9—Ni2—N5100.96 (15)N5—C9—H9B109.7
N8—Ni2—N591.32 (13)C10—C9—H9B109.7
N7—Ni2—N5162.93 (16)H9C—C9—H9B108.2
N10—Ni2—N588.20 (14)N6—C10—C9107.8 (3)
C1—S1—Ni1102.61 (14)N6—C10—H10A110.1
C2—S2—Ni1102.53 (13)C9—C10—H10A110.1
C3—S3—Ni1102.40 (15)N6—C10—H10B110.1
C4—S4—Ni1102.68 (15)C9—C10—H10B110.1
C9—N5—Ni2108.1 (3)H10A—C10—H10B108.5
C9—N5—H5A110 (3)N6—C11—C12108.0 (4)
Ni2—N5—H5A111 (3)N6—C11—H11A110.1
C9—N5—H5B114 (3)C12—C11—H11A110.1
Ni2—N5—H5B101 (3)N6—C11—H11B110.1
H5A—N5—H5B112 (5)C12—C11—H11B110.1
C11—N6—C10115.5 (4)H11A—C11—H11B108.4
C11—N6—Ni2106.8 (3)N7—C12—C11109.7 (4)
C10—N6—Ni2108.3 (3)N7—C12—H12A109.7
C11—N6—H6A108 (3)C11—C12—H12A109.7
C10—N6—H6A109 (3)N7—C12—H12B109.7
Ni2—N6—H6A109 (3)C11—C12—H12B109.7
C12—N7—Ni2107.2 (3)H12A—C12—H12B108.2
C12—N7—H7A110 (3)N8—C13—C14110.7 (3)
Ni2—N7—H7A120 (3)N8—C13—H13A109.5
C12—N7—H7B110 (4)C14—C13—H13A109.5
Ni2—N7—H7B109 (4)N8—C13—H13B109.5
H7A—N7—H7B100 (5)C14—C13—H13B109.5
C13—N8—Ni2109.1 (3)H13A—C13—H13B108.1
C13—N8—H8A105 (3)N9—C14—C13110.2 (4)
Ni2—N8—H8A118 (2)N9—C14—H14A109.6
C13—N8—H8B116 (3)C13—C14—H14A109.6
Ni2—N8—H8B108 (3)N9—C14—H14B109.6
H8A—N8—H8B101 (4)C13—C14—H14B109.6
C14—N9—C15119.5 (4)H14A—C14—H14B108.1
C14—N9—Ni2107.4 (3)N9—C15—C16110.1 (4)
C15—N9—Ni2108.0 (3)N9—C15—H15A109.6
C14—N9—H9A114 (4)C16—C15—H15A109.6
C15—N9—H9A100 (4)N9—C15—H15B109.6
Ni2—N9—H9A107 (5)C16—C15—H15B109.6
C16—N10—Ni2108.4 (3)H15A—C15—H15B108.2
C16—N10—H10C108 (3)N10—C16—C15109.8 (3)
Ni2—N10—H10C108 (3)N10—C16—H16A109.7
C16—N10—H10D108 (5)C15—C16—H16A109.7
Ni2—N10—H10D117 (5)N10—C16—H16B109.7
H10C—N10—H10D107 (5)C15—C16—H16B109.7
C2—C1—C5122.5 (3)H16A—C16—H16B108.2
C2—C1—S1120.5 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N5—H5A···N4i0.86 (3)2.30 (4)3.098 (6)154 (3)
N5—H5B···N2ii0.86 (3)2.48 (3)3.186 (5)140 (4)
N7—H7A···N3iii0.86 (4)2.56 (3)3.207 (7)134 (3)
N8—H8B···N3iii0.86 (3)2.48 (4)3.164 (6)138 (3)
N9—H9A···N1iv0.86 (2)2.58 (3)3.387 (6)156 (5)
N10—H10C···N2ii0.87 (3)2.34 (3)3.198 (5)173 (5)
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1/2, −y+1/2, z+1/2; (iii) x+1, y, z; (iv) −x+5/2, y+1/2, −z+1/2.
Table 1
Selected geometric parameters (Å, °) top
Ni1—S12.1739 (12)Ni2—N62.065 (3)
Ni1—S22.1617 (12)Ni2—N72.150 (4)
Ni1—S32.1732 (12)Ni2—N82.145 (3)
Ni1—S42.1658 (12)Ni2—N92.071 (4)
Ni2—N52.164 (3)Ni2—N102.151 (3)
S2—Ni1—S487.98 (5)N8—Ni2—N795.96 (15)
S2—Ni1—S3168.77 (5)N6—Ni2—N1098.69 (14)
S4—Ni1—S392.72 (4)N9—Ni2—N1081.72 (14)
S2—Ni1—S192.58 (4)N8—Ni2—N10163.04 (16)
S4—Ni1—S1170.10 (4)N7—Ni2—N1089.25 (16)
S3—Ni1—S188.65 (4)N6—Ni2—N581.47 (14)
N6—Ni2—N9177.56 (15)N9—Ni2—N5100.96 (15)
N6—Ni2—N898.00 (14)N8—Ni2—N591.32 (13)
N9—Ni2—N881.73 (14)N7—Ni2—N5162.93 (16)
N6—Ni2—N782.24 (16)N10—Ni2—N588.20 (14)
N9—Ni2—N795.37 (17)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N5—H5A···N4i0.86 (3)2.30 (4)3.098 (6)154 (3)
N5—H5B···N2ii0.86 (3)2.48 (3)3.186 (5)140 (4)
N7—H7A···N3iii0.86 (4)2.56 (3)3.207 (7)134 (3)
N8—H8B···N3iii0.86 (3)2.48 (4)3.164 (6)138 (3)
N9—H9A···N1iv0.86 (2)2.58 (3)3.387 (6)156 (5)
N10—H10C···N2ii0.87 (3)2.34 (3)3.198 (5)173 (5)
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1/2, −y+1/2, z+1/2; (iii) x+1, y, z; (iv) −x+5/2, y+1/2, −z+1/2.
Acknowledgements top

This work was supported by the Natural Science Foundation of China.

references
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