Bis(4-dimethyl-amino-1-ethyl-pyridinium) bis-(1,2-dicyano-ethene-1,2-dithiol-ato-κ(2)S,S')nickelate(II).

The asymmetric unit of the title complex, (C(9)H(15)N(2))(2)[Ni(C(4)N(2)S(2))(2)], comprises one 4-dimethyl-amino-1-ethyl-pyri-din-ium cation and one half of a [Ni(mnt)(2)](2-) (mnt(2-) = maleo-nitrile-dithiol-ate) anion; the complete anion is generated by the application of a centre of inversion. The Ni(II) ion is coordinated by four S atoms of two mnt(2-) ligands and exhibits a square-planar coordination geometry.

Related literature

For the magnetic and conducting properties of related complexes, see: Belo & Almedia (2010 ▶); Nishijo et al. (2000 ▶); Duan et al. (2010 ▶); Ni et al. (2005 ▶). For novel magnetic behaviour, see: Ni et al. (2004 ▶); Ren et al. (2004 ▶). For a related [Ni(mnt)2]2− complex, see: Yao et al. (2008 ▶). For the synthesis of the starting materials, see: Davison & Holm (1967 ▶); Duan et al. (2011 ▶).

Experimental

Crystal data

(C9H15N2)2[Ni(C4N2S2)2]

M = 641.55

Triclinic,

a = 8.1468 (14) Å

b = 9.3305 (16) Å

c = 11.663 (3) Å

α = 108.243 (3)°

β = 100.034 (3)°

γ = 107.830 (2)°

V = 765.0 (3) Å3

Z = 1

Mo Kα radiation

μ = 0.94 mm−1

T = 296 K

0.3 × 0.1 × 0.1 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.894, T max = 0.910

5798 measured reflections

2827 independent reflections

2371 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.128

S = 0.95

2827 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.25 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/S1600536812008161/tk5062sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008161/tk5062Isup2.hkl

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

(C9H15N2)2[Ni(C4N2S2)2]	V = 765.0 (3) Å3
Mr = 641.55	Z = 1
Triclinic, P1	F(000) = 334
Hall symbol: -P 1	Dx = 1.393 Mg m−3
a = 8.1468 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.3305 (16) Å	µ = 0.94 mm−1
c = 11.663 (3) Å	T = 296 K
α = 108.243 (3)°	Block, red
β = 100.034 (3)°	0.3 × 0.1 × 0.1 mm
γ = 107.830 (2)°

Bruker SMART CCD area-detector diffractometer	2827 independent reflections
Radiation source: fine-focus sealed tube	2371 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 25.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −9→9
Tmin = 0.894, Tmax = 0.910	k = −11→11
5798 measured reflections	l = −14→14

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) = 0.128	H-atom parameters constrained
S = 0.95	w = 1/[σ2(Fo2) + (0.091P)2 + 0.1169P] where P = (Fo2 + 2Fc2)/3
2827 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.25 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	1.0000	0.5000	0.5000	0.04490 (19)
S1	0.82193 (11)	0.48140 (9)	0.32858 (7)	0.0569 (2)
S2	0.98454 (10)	0.73406 (8)	0.59749 (7)	0.0544 (2)
N1	0.6004 (5)	0.2159 (4)	−0.0092 (3)	0.0933 (10)
N2	1.1487 (5)	1.0752 (4)	0.9081 (3)	0.1059 (12)
N3	0.4538 (3)	0.6143 (3)	0.2736 (2)	0.0612 (6)
C9	0.6202 (4)	0.8572 (3)	0.5178 (3)	0.0537 (6)
C1	0.6864 (5)	0.2485 (4)	0.0912 (3)	0.0653 (8)
C2	0.7958 (4)	0.2948 (3)	0.2175 (3)	0.0524 (6)
C3	1.1208 (4)	0.7989 (3)	0.7514 (3)	0.0514 (6)
C4	1.1395 (4)	0.9529 (4)	0.8407 (3)	0.0664 (8)
C5	0.1777 (5)	0.4619 (5)	0.0912 (4)	0.0947 (12)
H5A	0.1089	0.4361	0.1461	0.142*
H5B	0.1256	0.3745	0.0089	0.142*
H5C	0.1762	0.5614	0.0844	0.142*
C6	0.3668 (5)	0.4828 (4)	0.1439 (3)	0.0798 (10)
H6A	0.4360	0.5097	0.0884	0.096*
H6B	0.3682	0.3805	0.1468	0.096*
C7	0.4085 (4)	0.5897 (4)	0.3731 (3)	0.0648 (8)
H7	0.3215	0.4893	0.3593	0.078*
C8	0.4840 (4)	0.7048 (4)	0.4930 (3)	0.0634 (8)
H8	0.4462	0.6834	0.5589	0.076*
N4	0.7030 (4)	0.9716 (3)	0.6353 (2)	0.0637 (6)
C10	0.6603 (6)	0.9431 (5)	0.7439 (3)	0.0926 (11)
H10A	0.5331	0.9145	0.7325	0.139*
H10B	0.7268	1.0406	0.8190	0.139*
H10C	0.6925	0.8554	0.7523	0.139*
C11	0.8478 (5)	1.1248 (4)	0.6603 (3)	0.0776 (9)
H11A	0.9461	1.1030	0.6341	0.116*
H11B	0.8891	1.1914	0.7493	0.116*
H11C	0.8042	1.1815	0.6142	0.116*
C12	0.6630 (4)	0.8805 (3)	0.4110 (3)	0.0567 (7)
H12	0.7490	0.9796	0.4213	0.068*
C13	0.5803 (4)	0.7602 (4)	0.2938 (3)	0.0599 (7)
H13	0.6116	0.7786	0.2252	0.072*

	U11	U22	U33	U12	U13	U23
Ni1	0.0457 (3)	0.0453 (3)	0.0501 (3)	0.0200 (2)	0.0176 (2)	0.0227 (2)
S1	0.0658 (5)	0.0571 (4)	0.0549 (4)	0.0324 (4)	0.0152 (3)	0.0238 (3)
S2	0.0605 (4)	0.0485 (4)	0.0584 (4)	0.0259 (3)	0.0153 (3)	0.0228 (3)
N1	0.105 (2)	0.106 (2)	0.0599 (18)	0.047 (2)	0.0083 (17)	0.0229 (17)
N2	0.119 (3)	0.070 (2)	0.105 (3)	0.0448 (19)	0.021 (2)	0.0028 (18)
N3	0.0563 (14)	0.0638 (15)	0.0696 (16)	0.0287 (12)	0.0214 (12)	0.0273 (13)
C9	0.0549 (16)	0.0583 (15)	0.0637 (17)	0.0323 (13)	0.0240 (13)	0.0302 (14)
C1	0.072 (2)	0.0681 (18)	0.0600 (19)	0.0303 (16)	0.0212 (16)	0.0262 (15)
C2	0.0498 (15)	0.0568 (15)	0.0490 (15)	0.0174 (12)	0.0174 (12)	0.0205 (12)
C3	0.0507 (15)	0.0496 (14)	0.0544 (16)	0.0160 (12)	0.0209 (12)	0.0215 (12)
C4	0.0656 (19)	0.0556 (17)	0.075 (2)	0.0259 (14)	0.0180 (16)	0.0202 (16)
C5	0.072 (2)	0.079 (2)	0.096 (3)	0.0212 (19)	0.001 (2)	0.008 (2)
C6	0.079 (2)	0.069 (2)	0.081 (2)	0.0338 (18)	0.0181 (18)	0.0127 (17)
C7	0.0547 (17)	0.0584 (17)	0.086 (2)	0.0189 (14)	0.0233 (16)	0.0355 (16)
C8	0.0620 (18)	0.0736 (19)	0.073 (2)	0.0286 (15)	0.0327 (16)	0.0427 (17)
N4	0.0721 (16)	0.0657 (15)	0.0679 (16)	0.0372 (13)	0.0305 (13)	0.0289 (13)
C10	0.113 (3)	0.110 (3)	0.065 (2)	0.051 (2)	0.041 (2)	0.032 (2)
C11	0.082 (2)	0.0630 (19)	0.078 (2)	0.0297 (17)	0.0146 (18)	0.0192 (17)
C12	0.0554 (16)	0.0566 (15)	0.0668 (18)	0.0200 (13)	0.0229 (14)	0.0341 (14)
C13	0.0572 (17)	0.0734 (18)	0.0645 (18)	0.0293 (15)	0.0264 (14)	0.0380 (16)

Ni1—S2	2.1776 (8)	C5—H5A	0.9600
Ni1—S2i	2.1776 (8)	C5—H5B	0.9600
Ni1—S1i	2.1794 (8)	C5—H5C	0.9600
Ni1—S1	2.1794 (8)	C6—H6A	0.9700
S1—C2	1.738 (3)	C6—H6B	0.9700
S2—C3	1.742 (3)	C7—C8	1.358 (4)
N1—C1	1.147 (4)	C7—H7	0.9300
N2—C4	1.136 (4)	C8—H8	0.9300
N3—C7	1.342 (4)	N4—C11	1.452 (4)
N3—C13	1.351 (4)	N4—C10	1.451 (4)
N3—C6	1.493 (4)	C10—H10A	0.9600
C9—N4	1.339 (4)	C10—H10B	0.9600
C9—C8	1.415 (4)	C10—H10C	0.9600
C9—C12	1.412 (4)	C11—H11A	0.9600
C1—C2	1.435 (4)	C11—H11B	0.9600
C2—C3i	1.354 (4)	C11—H11C	0.9600
C3—C2i	1.354 (4)	C12—C13	1.356 (4)
C3—C4	1.431 (4)	C12—H12	0.9300
C5—C6	1.483 (5)	C13—H13	0.9300
S2—Ni1—S2i	180.0	C5—C6—H6B	109.2
S2—Ni1—S1i	92.00 (3)	N3—C6—H6B	109.2
S2i—Ni1—S1i	88.00 (3)	H6A—C6—H6B	107.9
S2—Ni1—S1	88.00 (3)	N3—C7—C8	122.9 (3)
S2i—Ni1—S1	92.00 (3)	N3—C7—H7	118.5
S1i—Ni1—S1	180.000 (1)	C8—C7—H7	118.5
C2—S1—Ni1	103.04 (10)	C7—C8—C9	120.0 (3)
C3—S2—Ni1	103.41 (10)	C7—C8—H8	120.0
C7—N3—C13	118.5 (3)	C9—C8—H8	120.0
C7—N3—C6	120.5 (3)	C9—N4—C11	121.5 (3)
C13—N3—C6	121.0 (3)	C9—N4—C10	121.3 (3)
N4—C9—C8	121.9 (3)	C11—N4—C10	117.0 (3)
N4—C9—C12	122.3 (3)	N4—C10—H10A	109.5
C8—C9—C12	115.8 (3)	N4—C10—H10B	109.5
N1—C1—C2	178.1 (3)	H10A—C10—H10B	109.5
C3i—C2—C1	122.2 (3)	N4—C10—H10C	109.5
C3i—C2—S1	121.3 (2)	H10A—C10—H10C	109.5
C1—C2—S1	116.5 (2)	H10B—C10—H10C	109.5
C2i—C3—C4	122.6 (3)	N4—C11—H11A	109.5
C2i—C3—S2	120.3 (2)	N4—C11—H11B	109.5
C4—C3—S2	117.2 (2)	H11A—C11—H11B	109.5
N2—C4—C3	177.2 (4)	N4—C11—H11C	109.5
C6—C5—H5A	109.5	H11A—C11—H11C	109.5
C6—C5—H5B	109.5	H11B—C11—H11C	109.5
H5A—C5—H5B	109.5	C13—C12—C9	120.8 (3)
C6—C5—H5C	109.5	C13—C12—H12	119.6
H5A—C5—H5C	109.5	C9—C12—H12	119.6
H5B—C5—H5C	109.5	N3—C13—C12	122.0 (3)
C5—C6—N3	112.0 (3)	N3—C13—H13	119.0
C5—C6—H6A	109.2	C12—C13—H13	119.0
N3—C6—H6A	109.2

Ni1—S2	2.1776 (8)
Ni1—S1	2.1794 (8)

S2—Ni1—S1

88.00 (3)