1-(2-Fluoro-benzyl-ideneamino)pyridinium bis-(1,2-dicyano-ethene-1,2-dithiol-ato)nickelate(II).

In the title complex, (C(12)H(10)FN(2))(2)[Ni(C(4)N(2)S(2))(2)], the anion lies on an inversion center with the Ni(II) ion coordinated by four S atoms in a slightly distorted square-planar environment. In the unique cation, the dihedral angle between the benzene and pyridine rings is 7.1 (2) Å.

Related literature

For metal–[dithiol­ene]2 complexes, see: Ni et al. (2004 ▶, 2005 ▶); Nishijo et al. (2000 ▶); Ren et al. (2004 ▶); Robertson & Cronin (2002 ▶).

Experimental

Crystal data

(C12H10FN2)2[Ni(C4N2S2)2]

M = 741.51

Triclinic,

a = 7.9248 (13) Å

b = 9.1774 (15) Å

c = 11.1526 (18) Å

α = 88.326 (3)°

β = 77.202 (4)°

γ = 85.448 (4)°

V = 788.4 (2) Å3

Z = 1

Mo Kα radiation

μ = 0.93 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.732, T max = 0.809

4282 measured reflections

3030 independent reflections

1785 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.094

S = 0.76

3030 reflections

214 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.24 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 datablocks global, I. DOI: 10.1107/S1600536809015360/lh2806sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015360/lh2806Isup2.hkl

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

(C12H10FN2)2[Ni(C4N2S2)2]	V = 788.4 (2) Å3
Mr = 741.51	Z = 1
Triclinic, P1	F(000) = 378
Hall symbol: -P 1	Dx = 1.562 Mg m−3
a = 7.9248 (13) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.1774 (15) Å	θ = 1.9–26.0°
c = 11.1526 (18) Å	µ = 0.93 mm−1
α = 88.326 (3)°	T = 293 K
β = 77.202 (4)°	Block, red
γ = 85.448 (4)°	0.30 × 0.20 × 0.20 mm

Bruker SMART CCD area-detector diffractometer	3030 independent reflections
Radiation source: fine-focus sealed tube	1785 reflections with I > 2σ(I)
graphite	Rint = 0.038
φ and ω scans	θmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −8→9
Tmin = 0.732, Tmax = 0.809	k = −11→11
4282 measured reflections	l = −13→12

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H-atom parameters constrained
S = 0.76	w = 1/[σ2(Fo2) + (0.0323P)2] where P = (Fo2 + 2Fc2)/3
3030 reflections	(Δ/σ)max = 0.004
214 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.24 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
F1	0.5021 (3)	0.3555 (2)	−0.1896 (2)	0.0724 (7)
N7	0.7362 (4)	0.1871 (3)	0.1593 (3)	0.0528 (8)
N8	0.7118 (5)	0.1192 (3)	0.0532 (3)	0.0646 (10)
C21	0.5600 (5)	0.2153 (4)	−0.2199 (4)	0.0561 (11)
C22	0.5388 (6)	0.1628 (5)	−0.3283 (4)	0.0735 (13)
H22A	0.4832	0.2200	−0.3804	0.088*
C23	0.6029 (6)	0.0220 (5)	−0.3571 (4)	0.0797 (14)
H23A	0.5949	−0.0156	−0.4320	0.096*
C24	0.6779 (6)	−0.0643 (5)	−0.2792 (4)	0.0742 (14)
H24A	0.7179	−0.1602	−0.3001	0.089*
C25	0.6944 (5)	−0.0094 (4)	−0.1700 (4)	0.0609 (11)
H25A	0.7452	−0.0686	−0.1166	0.073*
C26	0.6362 (5)	0.1333 (4)	−0.1381 (3)	0.0484 (10)
C27	0.6580 (5)	0.1978 (4)	−0.0257 (4)	0.0531 (10)
H27A	0.6319	0.2974	−0.0126	0.064*
C28	0.8296 (6)	0.1020 (4)	0.2236 (4)	0.0616 (12)
H28A	0.8723	0.0089	0.1956	0.074*
C29	0.8626 (6)	0.1496 (4)	0.3287 (4)	0.0704 (13)
H29A	0.9291	0.0905	0.3725	0.085*
C30	0.7965 (5)	0.2868 (4)	0.3703 (4)	0.0622 (12)
H30A	0.8182	0.3215	0.4425	0.075*
C31	0.6997 (6)	0.3708 (4)	0.3049 (4)	0.0667 (13)
H31A	0.6533	0.4632	0.3326	0.080*
C32	0.6708 (6)	0.3200 (4)	0.1996 (4)	0.0700 (13)
H32A	0.6048	0.3780	0.1546	0.084*
Ni1	0.0000	0.5000	0.0000	0.0484 (2)
S1	0.17387 (15)	0.40603 (10)	0.11191 (9)	0.0589 (3)
S2	−0.08272 (14)	0.68427 (10)	0.12200 (9)	0.0585 (3)
N1	0.2744 (5)	0.4501 (4)	0.4175 (3)	0.0771 (12)
N2	−0.0466 (5)	0.8166 (4)	0.4231 (3)	0.0776 (12)
C1	−0.0194 (5)	0.7374 (4)	0.3440 (4)	0.0571 (11)
C2	0.0169 (5)	0.6389 (4)	0.2423 (3)	0.0490 (10)
C3	0.1256 (5)	0.5188 (4)	0.2397 (3)	0.0501 (10)
C4	0.2087 (6)	0.4806 (4)	0.3384 (4)	0.0553 (11)

	U11	U22	U33	U12	U13	U23
F1	0.0756 (18)	0.0615 (15)	0.0818 (18)	0.0122 (13)	−0.0271 (14)	−0.0013 (13)
N7	0.063 (2)	0.0415 (18)	0.054 (2)	0.0031 (17)	−0.0156 (18)	−0.0038 (16)
N8	0.088 (3)	0.050 (2)	0.062 (2)	0.0107 (19)	−0.033 (2)	−0.0115 (18)
C21	0.049 (3)	0.057 (3)	0.061 (3)	−0.001 (2)	−0.010 (2)	−0.006 (2)
C22	0.076 (4)	0.084 (3)	0.067 (3)	−0.005 (3)	−0.031 (3)	0.004 (3)
C23	0.089 (4)	0.091 (4)	0.066 (3)	−0.004 (3)	−0.027 (3)	−0.023 (3)
C24	0.090 (4)	0.062 (3)	0.072 (3)	0.006 (3)	−0.022 (3)	−0.021 (3)
C25	0.070 (3)	0.049 (2)	0.068 (3)	0.003 (2)	−0.026 (2)	−0.006 (2)
C26	0.048 (3)	0.050 (2)	0.048 (2)	−0.006 (2)	−0.010 (2)	−0.0039 (19)
C27	0.053 (3)	0.044 (2)	0.061 (3)	0.003 (2)	−0.011 (2)	−0.007 (2)
C28	0.078 (3)	0.046 (2)	0.062 (3)	0.010 (2)	−0.024 (2)	−0.001 (2)
C29	0.091 (4)	0.058 (3)	0.068 (3)	0.013 (3)	−0.036 (3)	−0.005 (2)
C30	0.072 (3)	0.064 (3)	0.053 (3)	−0.001 (2)	−0.020 (2)	−0.009 (2)
C31	0.089 (4)	0.050 (3)	0.060 (3)	0.014 (2)	−0.019 (3)	−0.016 (2)
C32	0.095 (4)	0.053 (3)	0.066 (3)	0.026 (2)	−0.035 (3)	−0.012 (2)
Ni1	0.0527 (5)	0.0408 (4)	0.0520 (5)	0.0016 (3)	−0.0130 (4)	−0.0090 (3)
S1	0.0704 (8)	0.0504 (6)	0.0575 (7)	0.0119 (5)	−0.0214 (6)	−0.0151 (5)
S2	0.0655 (8)	0.0496 (6)	0.0631 (7)	0.0100 (5)	−0.0230 (6)	−0.0163 (5)
N1	0.100 (3)	0.068 (2)	0.068 (3)	0.008 (2)	−0.032 (2)	−0.010 (2)
N2	0.109 (3)	0.061 (2)	0.066 (3)	0.007 (2)	−0.028 (2)	−0.0186 (19)
C1	0.064 (3)	0.051 (3)	0.058 (3)	−0.002 (2)	−0.018 (2)	0.000 (2)
C2	0.050 (3)	0.039 (2)	0.056 (3)	−0.0034 (19)	−0.008 (2)	−0.0112 (19)
C3	0.057 (3)	0.043 (2)	0.051 (3)	0.000 (2)	−0.013 (2)	−0.0091 (19)
C4	0.068 (3)	0.042 (2)	0.055 (3)	0.001 (2)	−0.011 (2)	−0.011 (2)

F1—C21	1.358 (4)	C29—C30	1.378 (5)
N7—C28	1.335 (4)	C29—H29A	0.9300
N7—C32	1.337 (4)	C30—C31	1.355 (5)
N7—N8	1.410 (4)	C30—H30A	0.9300
N8—C27	1.249 (4)	C31—C32	1.348 (5)
C21—C22	1.364 (5)	C31—H31A	0.9300
C21—C26	1.377 (5)	C32—H32A	0.9300
C22—C23	1.371 (5)	Ni1—S2i	2.1689 (10)
C22—H22A	0.9300	Ni1—S2	2.1689 (9)
C23—C24	1.360 (5)	Ni1—S1i	2.1703 (10)
C23—H23A	0.9300	Ni1—S1	2.1703 (10)
C24—C25	1.369 (4)	S1—C3	1.741 (3)
C24—H24A	0.9300	S2—C2	1.726 (4)
C25—C26	1.382 (5)	N1—C4	1.138 (4)
C25—H25A	0.9300	N2—C1	1.132 (4)
C26—C27	1.451 (4)	C1—C2	1.436 (5)
C27—H27A	0.9300	C2—C3	1.341 (5)
C28—C29	1.348 (5)	C3—C4	1.424 (5)
C28—H28A	0.9300
C28—N7—C32	120.4 (3)	C28—C29—C30	119.2 (4)
C28—N7—N8	113.1 (3)	C28—C29—H29A	120.4
C32—N7—N8	126.4 (3)	C30—C29—H29A	120.4
C27—N8—N7	118.0 (3)	C31—C30—C29	119.3 (4)
F1—C21—C22	118.7 (4)	C31—C30—H30A	120.3
F1—C21—C26	117.7 (3)	C29—C30—H30A	120.3
C22—C21—C26	123.5 (4)	C32—C31—C30	119.8 (4)
C21—C22—C23	117.0 (4)	C32—C31—H31A	120.1
C21—C22—H22A	121.5	C30—C31—H31A	120.1
C23—C22—H22A	121.5	N7—C32—C31	120.6 (4)
C24—C23—C22	121.9 (4)	N7—C32—H32A	119.7
C24—C23—H23A	119.1	C31—C32—H32A	119.7
C22—C23—H23A	119.1	S2i—Ni1—S2	180.0
C23—C24—C25	119.7 (4)	S2i—Ni1—S1i	92.10 (4)
C23—C24—H24A	120.1	S2—Ni1—S1i	87.90 (4)
C25—C24—H24A	120.1	S2i—Ni1—S1	87.90 (4)
C24—C25—C26	120.7 (4)	S2—Ni1—S1	92.10 (4)
C24—C25—H25A	119.7	S1i—Ni1—S1	180.00 (4)
C26—C25—H25A	119.7	C3—S1—Ni1	102.69 (14)
C21—C26—C25	117.1 (4)	C2—S2—Ni1	102.72 (13)
C21—C26—C27	120.4 (4)	N2—C1—C2	178.9 (5)
C25—C26—C27	122.5 (4)	C3—C2—C1	121.6 (4)
N8—C27—C26	119.8 (3)	C3—C2—S2	121.5 (3)
N8—C27—H27A	120.1	C1—C2—S2	116.9 (3)
C26—C27—H27A	120.1	C2—C3—C4	121.9 (3)
N7—C28—C29	120.7 (4)	C2—C3—S1	120.3 (3)
N7—C28—H28A	119.7	C4—C3—S1	117.7 (3)
C29—C28—H28A	119.7	N1—C4—C3	179.7 (5)