3,3'-Dimethyl-1,1'-(propane-1,3-di-yl)diimidazol-1-ium bis-(1,2-dicyano-ethene-1,2-dithiol-ato-κS,S')nickelate(II).

In the title compound, (C(11)H(18)N(4))[Ni(C(4)N(2)S(2))(2)], the asymmetric contains one half-complex, with the cation placed on a twofold axis and the anion located on an inversion center. The Ni(II) ion in the anion is coordinated by four S atoms of two maleonitrile-dithiol-ate ligands, and exhibits the expected square-planar coordination geometry.

Related literature

For the design of functional materials, see: Robertson & Cronin (2002 ▶). For near-infrared dyes, conducting, magnetic and non-linear optical materials, 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 ▶); For the synthesis of the title compound, see: Davison & Holm (1967 ▶); Yao et al. (2008 ▶).

Experimental

Crystal data

(C11H18N4)[Ni(C4N2S2)2]

M = 545.38

Monoclinic,

a = 19.3683 (15) Å

b = 7.3026 (6) Å

c = 17.5170 (14) Å

β = 104.167 (1)°

V = 2402.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 1.18 mm−1

T = 293 K

0.4 × 0.3 × 0.3 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.702, T max = 0.741

7551 measured reflections

2938 independent reflections

2503 reflections with I > 2σ(I)

R int = 0.067

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.101

S = 1.06

2938 reflections

147 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.68 e Å−3

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; 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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811027693/bh2362sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811027693/bh2362Isup2.hkl

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

(C11H18N4)[Ni(C4N2S2)2]	Z = 4
Mr = 545.38	F(000) = 1120.0
Monoclinic, C2/c	Dx = 1.508 Mg m−3
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 19.3683 (15) Å	µ = 1.18 mm−1
b = 7.3026 (6) Å	T = 293 K
c = 17.5170 (14) Å	Block, red
β = 104.167 (1)°	0.4 × 0.3 × 0.3 mm
V = 2402.2 (3) Å3

Bruker SMART CCD area-detector diffractometer	2938 independent reflections
Radiation source: fine-focus sealed tube	2503 reflections with I > 2σ(I)
graphite	Rint = 0.067
φ and ω scans	θmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −19→25
Tmin = 0.702, Tmax = 0.741	k = −8→9
7551 measured reflections	l = −23→16

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0544P)2 + 0.2056P] where P = (Fo2 + 2Fc2)/3
2938 reflections	(Δ/σ)max < 0.001
147 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.68 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ni1	0.2500	0.7500	0.0000	0.03604 (12)
S1	0.34431 (2)	0.65936 (7)	0.08669 (3)	0.04682 (15)
S2	0.18479 (2)	0.72779 (7)	0.08353 (3)	0.04539 (14)
N1	0.40853 (10)	0.5664 (3)	0.29918 (11)	0.0762 (6)
N2	0.19161 (11)	0.6190 (3)	0.28956 (11)	0.0698 (5)
N3	0.61640 (10)	0.7743 (2)	1.00222 (10)	0.0491 (4)
N4	0.54547 (9)	0.8708 (2)	0.89552 (10)	0.0576 (4)
C1	0.36589 (10)	0.5949 (3)	0.24289 (11)	0.0516 (4)
C2	0.31437 (9)	0.6359 (2)	0.17168 (10)	0.0416 (4)
C3	0.24477 (9)	0.6629 (2)	0.17021 (10)	0.0401 (4)
C4	0.21663 (10)	0.6392 (3)	0.23745 (11)	0.0492 (4)
C5	0.61229 (10)	0.8655 (3)	0.93644 (11)	0.0475 (4)
H5A	0.6506	0.9180	0.9212	0.057*
C6	0.68163 (15)	0.7392 (3)	1.06347 (14)	0.0661 (7)
H6A	0.7213	0.7962	1.0491	0.099*
H6B	0.6896	0.6096	1.0689	0.099*
H6C	0.6767	0.7889	1.1126	0.099*
C7	0.55032 (15)	0.7161 (4)	1.00398 (16)	0.0803 (8)
H7A	0.5380	0.6474	1.0434	0.096*
C8	0.50654 (15)	0.7773 (5)	0.9379 (2)	0.0919 (10)
H8A	0.4575	0.7592	0.9231	0.110*
C9	0.52021 (13)	0.9711 (3)	0.82143 (13)	0.0750 (7)
H9A	0.5573	1.0547	0.8150	0.090*
H9B	0.4792	1.0439	0.8248	0.090*
C10	0.5000	0.8508 (4)	0.7500	0.0559 (7)
H10A	0.4602	0.7731	0.7532	0.067*	0.50
H10B	0.5398	0.7731	0.7468	0.067*	0.50

	U11	U22	U33	U12	U13	U23
Ni1	0.03490 (18)	0.03872 (19)	0.03238 (19)	−0.00051 (11)	0.00419 (13)	−0.00245 (11)
S1	0.0380 (2)	0.0625 (3)	0.0377 (2)	0.00491 (19)	0.00505 (18)	0.0005 (2)
S2	0.0379 (2)	0.0577 (3)	0.0397 (3)	0.00376 (18)	0.00789 (19)	0.00350 (19)
N1	0.0665 (12)	0.1072 (17)	0.0468 (10)	0.0188 (12)	−0.0018 (9)	0.0070 (11)
N2	0.0691 (11)	0.0954 (14)	0.0488 (10)	0.0063 (11)	0.0220 (9)	0.0090 (10)
N3	0.0537 (9)	0.0483 (9)	0.0413 (9)	−0.0086 (7)	0.0039 (7)	−0.0020 (7)
N4	0.0479 (9)	0.0663 (10)	0.0497 (9)	−0.0038 (8)	−0.0049 (7)	−0.0074 (8)
C1	0.0493 (10)	0.0627 (11)	0.0406 (9)	0.0054 (9)	0.0065 (8)	−0.0019 (9)
C2	0.0462 (9)	0.0413 (8)	0.0344 (8)	0.0003 (7)	0.0042 (7)	−0.0017 (7)
C3	0.0459 (9)	0.0382 (8)	0.0346 (8)	−0.0023 (7)	0.0069 (7)	−0.0022 (7)
C4	0.0503 (10)	0.0539 (10)	0.0423 (10)	0.0019 (8)	0.0091 (8)	0.0012 (8)
C5	0.0454 (9)	0.0498 (10)	0.0423 (10)	−0.0046 (8)	0.0012 (7)	0.0019 (8)
C6	0.0740 (15)	0.0568 (13)	0.0549 (14)	0.0002 (10)	−0.0086 (12)	0.0085 (9)
C7	0.0686 (16)	0.112 (2)	0.0614 (15)	−0.0278 (15)	0.0177 (13)	0.0053 (14)
C8	0.0446 (12)	0.140 (3)	0.087 (2)	−0.0210 (14)	0.0079 (13)	0.0053 (19)
C9	0.0783 (15)	0.0643 (13)	0.0611 (13)	0.0102 (12)	−0.0238 (12)	−0.0046 (11)
C10	0.0481 (14)	0.0592 (17)	0.0525 (16)	0.000	−0.0027 (12)	0.000

Ni1—S2i	2.1603 (5)	C2—C3	1.356 (3)
Ni1—S2	2.1603 (5)	C3—C4	1.424 (3)
Ni1—S1	2.1732 (4)	C5—H5A	0.9300
Ni1—S1i	2.1732 (4)	C6—H6A	0.9600
S1—C2	1.7334 (18)	C6—H6B	0.9600
S2—C3	1.7369 (17)	C6—H6C	0.9600
N1—C1	1.140 (2)	C7—C8	1.334 (4)
N2—C4	1.143 (3)	C7—H7A	0.9300
N3—C5	1.316 (2)	C8—H8A	0.9300
N3—C7	1.356 (3)	C9—C10	1.500 (3)
N3—C6	1.466 (3)	C9—H9A	0.9700
N4—C5	1.318 (2)	C9—H9B	0.9700
N4—C8	1.364 (4)	C10—C9ii	1.500 (3)
N4—C9	1.466 (3)	C10—H10A	0.9700
C1—C2	1.426 (2)	C10—H10B	0.9700
S2i—Ni1—S2	180.00 (3)	N3—C6—H6A	109.5
S2i—Ni1—S1	88.018 (18)	N3—C6—H6B	109.5
S2—Ni1—S1	91.983 (18)	H6A—C6—H6B	109.5
S2i—Ni1—S1i	91.983 (18)	N3—C6—H6C	109.5
S2—Ni1—S1i	88.017 (18)	H6A—C6—H6C	109.5
S1—Ni1—S1i	180.000 (17)	H6B—C6—H6C	109.5
C2—S1—Ni1	103.27 (6)	C8—C7—N3	106.2 (2)
C3—S2—Ni1	103.64 (6)	C8—C7—H7A	126.9
C5—N3—C7	108.85 (19)	N3—C7—H7A	126.9
C5—N3—C6	125.85 (19)	C7—C8—N4	108.8 (2)
C7—N3—C6	125.3 (2)	C7—C8—H8A	125.6
C5—N4—C8	106.8 (2)	N4—C8—H8A	125.6
C5—N4—C9	124.5 (2)	N4—C9—C10	114.08 (19)
C8—N4—C9	128.5 (2)	N4—C9—H9A	108.7
N1—C1—C2	177.7 (2)	C10—C9—H9A	108.7
C3—C2—C1	121.79 (17)	N4—C9—H9B	108.7
C3—C2—S1	120.62 (13)	C10—C9—H9B	108.7
C1—C2—S1	117.55 (14)	H9A—C9—H9B	107.6
C2—C3—C4	123.12 (16)	C9—C10—C9ii	108.3 (3)
C2—C3—S2	120.34 (14)	C9—C10—H10A	110.0
C4—C3—S2	116.53 (14)	C9ii—C10—H10A	110.0
N2—C4—C3	177.4 (2)	C9—C10—H10B	110.0
N3—C5—N4	109.39 (19)	C9ii—C10—H10B	110.0
N3—C5—H5A	125.3	H10A—C10—H10B	108.4
N4—C5—H5A	125.3