3-Butyl-1-methyl-1H-imidazol-3-ium bis-(1,2-dicyano-ethene-1,2-dithiol-ato-κS,S')nickel(III).

In the title compound, (C(8)H(15)N(2))[Ni(C(4)N(2)S(2))(2)], the Ni(III) atom is coordinated by four S atoms of two maleonitrile-dithiol-ate ligands and exhibits a distorted square-planar geometry. In the crystal, the cations and anions are connected alternately by weak inter-molecular C-H⋯N hydrogen bonds, forming a zigzag chain along [201].

Related literature

For applications of bis­(1,2-dithiol­ene) complexes of transition metals, see: Nishijo et al. (2000 ▶); Ni et al. (2005 ▶). For related structures, see: Ni et al. (2004 ▶); Ren et al. (2004 ▶, 2008 ▶); Duan et al. (2010 ▶).

Experimental

Crystal data

(C8H15N2)[Ni(C4N2S2)2]

M = 478.31

Monoclinic,

a = 10.650 (2) Å

b = 7.3924 (13) Å

c = 26.691 (5) Å

β = 93.463 (5)°

V = 2097.5 (7) Å3

Z = 4

Mo Kα radiation

μ = 1.34 mm−1

T = 298 K

0.40 × 0.20 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.733, T max = 0.818

19183 measured reflections

3824 independent reflections

3246 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.099

S = 1.16

3824 reflections

247 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.34 e Å−3

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

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811046824/is2799sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811046824/is2799Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

(C8H15N2)[Ni(C4N2S2)2]	F(000) = 980.0
Mr = 478.31	Dx = 1.515 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -p 2Ybc	Cell parameters from 778 reflections
a = 10.650 (2) Å	θ = 2.6–21.2°
b = 7.3924 (13) Å	µ = 1.34 mm−1
c = 26.691 (5) Å	T = 298 K
β = 93.463 (5)°	Block, black
V = 2097.5 (7) Å3	0.40 × 0.20 × 0.15 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3824 independent reflections
Radiation source: fine-focus sealed tube	3246 reflections with I > 2σ(I)
graphite	Rint = 0.044
φ and ω scans	θmax = 25.4°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −12→12
Tmin = 0.733, Tmax = 0.818	k = −8→7
19183 measured reflections	l = −32→30

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H-atom parameters constrained
S = 1.16	w = 1/[σ2(Fo2) + (0.0319P)2 + 1.4061P] where P = (Fo2 + 2Fc2)/3
3824 reflections	(Δ/σ)max = 0.001
247 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

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.

	x	y	z	Uiso*/Ueq
Ni1	0.09847 (4)	0.70716 (6)	0.503296 (15)	0.04030 (15)
S1	0.13066 (8)	0.76184 (13)	0.42646 (3)	0.0483 (2)
S2	−0.09351 (8)	0.79241 (12)	0.49400 (3)	0.0456 (2)
S3	0.28875 (9)	0.61212 (14)	0.51160 (3)	0.0507 (3)
S4	0.06746 (9)	0.65718 (13)	0.58064 (3)	0.0486 (2)
N1	−0.0210 (4)	0.9489 (6)	0.31048 (14)	0.0832 (12)
N2	−0.3277 (3)	0.9738 (5)	0.40060 (15)	0.0789 (11)
N3	0.5208 (4)	0.4175 (6)	0.60350 (16)	0.0882 (13)
N4	0.2194 (4)	0.4677 (6)	0.69608 (14)	0.0956 (14)
N5	0.6606 (3)	0.8606 (4)	0.59871 (10)	0.0476 (7)
N6	0.7729 (3)	0.7519 (4)	0.66100 (11)	0.0510 (8)
C1	−0.2310 (4)	0.9224 (5)	0.41389 (15)	0.0532 (10)
C2	−0.1106 (3)	0.8554 (4)	0.43214 (13)	0.0425 (8)
C3	−0.0107 (3)	0.8444 (4)	0.40249 (13)	0.0432 (8)
C4	−0.0187 (3)	0.9029 (6)	0.35110 (15)	0.0550 (10)
C5	0.4244 (4)	0.4750 (6)	0.59122 (15)	0.0596 (11)
C6	0.3061 (3)	0.5491 (5)	0.57365 (13)	0.0477 (9)
C7	0.2078 (3)	0.5671 (5)	0.60397 (13)	0.0478 (9)
C8	0.2156 (4)	0.5117 (6)	0.65538 (16)	0.0612 (11)
C9	0.5952 (6)	0.3532 (9)	0.7533 (3)	0.157 (3)
H9A	0.5596	0.2909	0.7243	0.236*
H9B	0.5289	0.3953	0.7732	0.236*
H9C	0.6487	0.2722	0.7729	0.236*
C10	0.6682 (5)	0.5058 (7)	0.7376 (2)	0.0941 (17)
H10A	0.7005	0.5701	0.7673	0.113*
H10B	0.6124	0.5875	0.7185	0.113*
C11	0.7771 (4)	0.4598 (6)	0.70632 (16)	0.0681 (12)
H11A	0.8329	0.3767	0.7249	0.082*
H11B	0.7455	0.3992	0.6759	0.082*
C12	0.8509 (4)	0.6250 (6)	0.69236 (15)	0.0665 (12)
H12A	0.8823	0.6863	0.7227	0.080*
H12B	0.9226	0.5876	0.6742	0.080*
C13	0.7196 (4)	0.9081 (6)	0.67674 (14)	0.0592 (10)
H13	0.7301	0.9583	0.7087	0.071*
C14	0.6497 (4)	0.9761 (5)	0.63792 (14)	0.0573 (10)
H14	0.6027	1.0821	0.6377	0.069*
C15	0.6000 (4)	0.8833 (6)	0.54840 (13)	0.0624 (11)
H15A	0.6348	0.9871	0.5326	0.094*
H15B	0.5112	0.9002	0.5509	0.094*
H15C	0.6144	0.7774	0.5287	0.094*
C16	0.7359 (3)	0.7259 (5)	0.61352 (13)	0.0493 (9)
H16	0.7588	0.6291	0.5937	0.059*

	U11	U22	U33	U12	U13	U23
Ni1	0.0425 (3)	0.0390 (3)	0.0395 (3)	−0.0044 (2)	0.0042 (2)	−0.00279 (19)
S1	0.0432 (5)	0.0599 (6)	0.0422 (5)	0.0011 (4)	0.0067 (4)	0.0003 (4)
S2	0.0430 (5)	0.0454 (5)	0.0490 (5)	−0.0041 (4)	0.0084 (4)	−0.0038 (4)
S3	0.0461 (5)	0.0585 (6)	0.0476 (5)	−0.0001 (5)	0.0036 (4)	0.0011 (5)
S4	0.0529 (6)	0.0490 (6)	0.0446 (5)	−0.0023 (4)	0.0076 (4)	0.0001 (4)
N1	0.076 (3)	0.118 (3)	0.054 (2)	−0.009 (2)	−0.005 (2)	0.012 (2)
N2	0.052 (2)	0.081 (3)	0.102 (3)	0.006 (2)	−0.004 (2)	−0.003 (2)
N3	0.056 (2)	0.100 (3)	0.107 (3)	−0.001 (2)	−0.013 (2)	0.027 (3)
N4	0.121 (4)	0.112 (4)	0.053 (2)	−0.006 (3)	−0.001 (2)	0.019 (2)
N5	0.0408 (17)	0.058 (2)	0.0440 (17)	−0.0021 (15)	0.0029 (14)	0.0024 (15)
N6	0.0439 (18)	0.064 (2)	0.0444 (18)	−0.0002 (16)	−0.0010 (14)	0.0042 (16)
C1	0.051 (2)	0.047 (2)	0.061 (2)	−0.0069 (19)	0.002 (2)	−0.0057 (19)
C2	0.042 (2)	0.0330 (18)	0.052 (2)	−0.0043 (15)	−0.0030 (17)	−0.0037 (16)
C3	0.044 (2)	0.040 (2)	0.045 (2)	−0.0047 (16)	−0.0017 (16)	−0.0040 (16)
C4	0.048 (2)	0.065 (3)	0.051 (2)	−0.0016 (19)	−0.0032 (19)	−0.003 (2)
C5	0.054 (3)	0.060 (3)	0.064 (3)	−0.007 (2)	−0.002 (2)	0.011 (2)
C6	0.051 (2)	0.044 (2)	0.048 (2)	−0.0071 (17)	−0.0043 (18)	0.0020 (17)
C7	0.056 (2)	0.045 (2)	0.041 (2)	−0.0131 (17)	−0.0027 (18)	0.0002 (17)
C8	0.069 (3)	0.061 (3)	0.052 (3)	−0.007 (2)	−0.003 (2)	0.004 (2)
C9	0.149 (6)	0.121 (6)	0.211 (8)	0.013 (5)	0.089 (6)	0.062 (5)
C10	0.081 (3)	0.093 (4)	0.112 (4)	0.006 (3)	0.033 (3)	0.029 (3)
C11	0.070 (3)	0.072 (3)	0.062 (3)	0.016 (2)	0.003 (2)	0.012 (2)
C12	0.048 (2)	0.091 (3)	0.060 (2)	0.009 (2)	−0.001 (2)	0.019 (2)
C13	0.066 (3)	0.065 (3)	0.047 (2)	−0.003 (2)	0.004 (2)	−0.009 (2)
C14	0.060 (3)	0.055 (2)	0.057 (2)	0.007 (2)	0.007 (2)	0.001 (2)
C15	0.050 (2)	0.086 (3)	0.050 (2)	0.000 (2)	−0.0053 (19)	0.005 (2)
C16	0.044 (2)	0.057 (2)	0.047 (2)	0.0003 (18)	0.0053 (17)	−0.0027 (18)

Ni1—S1	2.1382 (10)	C6—C7	1.368 (5)
Ni1—S2	2.1395 (10)	C7—C8	1.429 (5)
Ni1—S4	2.1424 (10)	C9—C10	1.446 (7)
Ni1—S3	2.1436 (11)	C9—H9A	0.9600
S1—C3	1.712 (4)	C9—H9B	0.9600
S2—C2	1.715 (4)	C9—H9C	0.9600
S3—C6	1.719 (4)	C10—C11	1.509 (6)
S4—C7	1.718 (4)	C10—H10A	0.9700
N1—C4	1.135 (5)	C10—H10B	0.9700
N2—C1	1.134 (5)	C11—C12	1.510 (6)
N3—C5	1.140 (5)	C11—H11A	0.9700
N4—C8	1.133 (5)	C11—H11B	0.9700
N5—C16	1.324 (4)	C12—H12A	0.9700
N5—C14	1.361 (5)	C12—H12B	0.9700
N5—C15	1.464 (4)	C13—C14	1.337 (5)
N6—C16	1.318 (4)	C13—H13	0.9300
N6—C13	1.364 (5)	C14—H14	0.9300
N6—C12	1.479 (5)	C15—H15A	0.9600
C1—C2	1.433 (5)	C15—H15B	0.9600
C2—C3	1.366 (5)	C15—H15C	0.9600
C3—C4	1.436 (5)	C16—H16	0.9300
C5—C6	1.428 (5)
S1—Ni1—S2	92.32 (4)	H9A—C9—H9C	109.5
S1—Ni1—S4	178.96 (4)	H9B—C9—H9C	109.5
S2—Ni1—S4	87.75 (4)	C9—C10—C11	115.5 (5)
S1—Ni1—S3	87.47 (4)	C9—C10—H10A	108.4
S2—Ni1—S3	177.89 (4)	C11—C10—H10A	108.4
S4—Ni1—S3	92.50 (4)	C9—C10—H10B	108.4
C3—S1—Ni1	103.73 (12)	C11—C10—H10B	108.4
C2—S2—Ni1	103.70 (12)	H10A—C10—H10B	107.5
C6—S3—Ni1	103.54 (13)	C12—C11—C10	112.5 (4)
C7—S4—Ni1	103.58 (12)	C12—C11—H11A	109.1
C16—N5—C14	108.7 (3)	C10—C11—H11A	109.1
C16—N5—C15	125.8 (3)	C12—C11—H11B	109.1
C14—N5—C15	125.5 (3)	C10—C11—H11B	109.1
C16—N6—C13	108.3 (3)	H11A—C11—H11B	107.8
C16—N6—C12	125.2 (3)	N6—C12—C11	111.7 (3)
C13—N6—C12	126.3 (3)	N6—C12—H12A	109.3
N2—C1—C2	178.1 (5)	C11—C12—H12A	109.3
C3—C2—C1	122.4 (3)	N6—C12—H12B	109.3
C3—C2—S2	120.0 (3)	C11—C12—H12B	109.3
C1—C2—S2	117.5 (3)	H12A—C12—H12B	107.9
C2—C3—C4	122.1 (3)	C14—C13—N6	107.6 (3)
C2—C3—S1	120.2 (3)	C14—C13—H13	126.2
C4—C3—S1	117.7 (3)	N6—C13—H13	126.2
N1—C4—C3	177.8 (4)	C13—C14—N5	106.9 (4)
N3—C5—C6	177.3 (5)	C13—C14—H14	126.5
C7—C6—C5	122.3 (3)	N5—C14—H14	126.5
C7—C6—S3	120.1 (3)	N5—C15—H15A	109.5
C5—C6—S3	117.5 (3)	N5—C15—H15B	109.5
C6—C7—C8	122.5 (4)	H15A—C15—H15B	109.5
C6—C7—S4	120.2 (3)	N5—C15—H15C	109.5
C8—C7—S4	117.3 (3)	H15A—C15—H15C	109.5
N4—C8—C7	178.7 (5)	H15B—C15—H15C	109.5
C10—C9—H9A	109.5	N6—C16—N5	108.5 (3)
C10—C9—H9B	109.5	N6—C16—H16	125.7
H9A—C9—H9B	109.5	N5—C16—H16	125.7
C10—C9—H9C	109.5
S3—Ni1—S1—C3	179.03 (12)	C5—C6—C7—S4	−179.9 (3)
S1—Ni1—S2—C2	−0.41 (12)	S3—C6—C7—S4	−1.4 (4)
S4—Ni1—S2—C2	178.55 (12)	Ni1—S4—C7—C6	1.9 (3)
S1—Ni1—S3—C6	179.74 (13)	Ni1—S4—C7—C8	−177.6 (3)
S4—Ni1—S3—C6	0.78 (13)	C9—C10—C11—C12	−178.6 (5)
S2—Ni1—S4—C7	176.57 (13)	C16—N6—C12—C11	−72.9 (5)
Ni1—S2—C2—C3	−0.7 (3)	C13—N6—C12—C11	102.1 (5)
Ni1—S2—C2—C1	−179.3 (2)	C10—C11—C12—N6	−62.5 (5)
C1—C2—C3—C4	1.3 (5)	C16—N6—C13—C14	0.0 (4)
S2—C2—C3—C4	−177.2 (3)	C12—N6—C13—C14	−175.7 (3)
C1—C2—C3—S1	−179.6 (3)	N6—C13—C14—N5	0.1 (4)
S2—C2—C3—S1	1.8 (4)	C16—N5—C14—C13	−0.2 (4)
Ni1—S1—C3—C2	−1.9 (3)	C15—N5—C14—C13	−179.5 (3)
Ni1—S1—C3—C4	177.2 (3)	C13—N6—C16—N5	−0.1 (4)
Ni1—S3—C6—C7	0.2 (3)	C12—N6—C16—N5	175.6 (3)
Ni1—S3—C6—C5	178.7 (3)	C14—N5—C16—N6	0.2 (4)
C5—C6—C7—C8	−0.5 (6)	C15—N5—C16—N6	179.6 (3)
S3—C6—C7—C8	178.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···N4i	0.93	2.57	3.446 (5)	158
C15—H15B···N2ii	0.96	2.58	3.443 (5)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯N4i	0.93	2.57	3.446 (5)	158
C15—H15B⋯N2ii	0.96	2.58	3.443 (5)	149

Symmetry codes: (i) ; (ii) .