Bis(8-hy-droxy-1-methyl-quinolin-1-ium) bis-(1,2-dicyano-ethene-1,2-dithiol-ato)nickelate(II) dihydrate.

In the title ion-pair complex, (C(10)H(10)NO)(2)[Ni(C(4)N(2)S(2))(2)]·2H(2)O, the anion has crystallographically imposed centre of symmetry. The Ni(II) atom exhibits a slightly distorted square-planar coordination geometry. In the crystal, the water mol-ecule links anions and cations into a three-dimensional network via O-H⋯N, O-H⋯S and O-H⋯O hydrogen bonds. The structure is further stabilized by weak S⋯π contacts [S⋯centroid = 3.8047 (9) Å] and π-π stacking inter-actions [centriod-centroid distance = 3.8653 (7) Å].

Related literature

For background to the properties and applications of bis-1,2-dithiol­ene metal complexes, see: Brammer (2004 ▶); Hill et al. (2005 ▶); Robin & Fromm (2006 ▶); Carlucci et al. (2003 ▶). For details of square-planar 1,2-dithiol­ene metal complexes, see: Robertson & Cronin (2002 ▶); Coomber et al. (1996 ▶); Ni et al. (2005 ▶); Duan et al. (2010 ▶).

Experimental

Crystal data

(C10H10NO)2[Ni(C4N2S2)2]·2H2O

M = 695.50

Triclinic,

a = 8.786 (2) Å

b = 9.277 (2) Å

c = 9.667 (2) Å

α = 82.064 (4)°

β = 78.058 (4)°

γ = 83.324 (4)°

V = 760.4 (3) Å3

Z = 1

Mo Kα radiation

μ = 0.96 mm−1

T = 291 K

0.35 × 0.20 × 0.15 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.796, T max = 0.865

3798 measured reflections

2679 independent reflections

2179 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.097

S = 1.00

2679 reflections

197 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.28 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) I, global. DOI: 10.1107/S1600536811045430/rz2659sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811045430/rz2659Isup2.hkl

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

(C10H10NO)2[Ni(C4N2S2)2]·2H2O	Z = 1
Mr = 695.50	F(000) = 358
Triclinic, P1	Dx = 1.519 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.786 (2) Å	Cell parameters from 1684 reflections
b = 9.277 (2) Å	θ = 2.4–24.2°
c = 9.667 (2) Å	µ = 0.96 mm−1
α = 82.064 (4)°	T = 291 K
β = 78.058 (4)°	Block, red-brown
γ = 83.324 (4)°	0.35 × 0.20 × 0.15 mm
V = 760.4 (3) Å3

Bruker SMART APEX CCD area-detector diffractometer	2679 independent reflections
Radiation source: sealed tube	2179 reflections with I > 2σ(I)
graphite	Rint = 0.057
φ and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→9
Tmin = 0.796, Tmax = 0.865	k = −11→10
3798 measured reflections	l = −11→8

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0419P)2] where P = (Fo2 + 2Fc2)/3
2679 reflections	(Δ/σ)max < 0.001
197 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −0.28 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
C1	0.1931 (4)	−0.1818 (4)	0.2692 (4)	0.0795 (10)
H1A	0.2548	−0.2742	0.2672	0.095*
C2	0.0785 (4)	−0.1531 (4)	0.1891 (4)	0.0880 (12)
H2A	0.0584	−0.2267	0.1362	0.106*
C3	−0.0068 (4)	−0.0222 (4)	0.1882 (4)	0.0806 (10)
H3A	−0.0890	−0.0007	0.1347	0.097*
C4	0.0262 (3)	0.0846 (3)	0.2640 (3)	0.0593 (8)
C5	−0.0561 (4)	0.2226 (4)	0.2571 (4)	0.0722 (9)
H5A	−0.1334	0.2450	0.1983	0.087*
C6	−0.0264 (4)	0.3248 (3)	0.3313 (4)	0.0724 (9)
H6A	−0.0808	0.4207	0.3252	0.087*
C7	0.0860 (3)	0.2922 (3)	0.4167 (3)	0.0648 (8)
H7A	0.1040	0.3660	0.4704	0.078*
C8	0.1707 (3)	0.1592 (3)	0.4260 (3)	0.0551 (7)
C9	0.1429 (3)	0.0509 (3)	0.3479 (3)	0.0499 (7)
C10	0.3498 (4)	−0.1336 (3)	0.4296 (4)	0.0816 (10)
H10A	0.3917	−0.2316	0.4143	0.122*
H10B	0.4315	−0.0692	0.3997	0.122*
H10C	0.3070	−0.1299	0.5289	0.122*
C11	0.5319 (4)	−0.3805 (3)	0.7603 (3)	0.0642 (8)
C12	0.5454 (3)	−0.2796 (3)	0.8553 (3)	0.0529 (7)
C13	0.3540 (3)	0.3089 (3)	1.0562 (3)	0.0533 (7)
C14	0.2600 (4)	0.4443 (3)	1.0453 (4)	0.0684 (9)
N1	0.2236 (3)	−0.0862 (3)	0.3466 (3)	0.0615 (7)
N2	0.5227 (4)	−0.4590 (3)	0.6826 (3)	0.0914 (10)
N3	0.1864 (4)	0.5531 (3)	1.0351 (4)	0.1009 (11)
Ni1	0.5000	0.0000	1.0000	0.04543 (18)
O1	0.2796 (2)	0.1319 (2)	0.5071 (2)	0.0766 (6)
H1W	0.2823	0.2143	0.5595	0.108 (13)*
O2	0.2867 (2)	0.3545 (2)	0.6480 (2)	0.0839 (7)
H2B	0.3566	0.3340	0.6984	0.126*
H2C	0.3081	0.4295	0.5889	0.126*
S1	0.42937 (9)	−0.11519 (8)	0.84759 (9)	0.0614 (2)
S2	0.33291 (10)	0.17888 (8)	0.95058 (9)	0.0642 (2)

	U11	U22	U33	U12	U13	U23
C1	0.082 (2)	0.059 (2)	0.094 (3)	−0.0075 (17)	0.002 (2)	−0.0232 (19)
C2	0.091 (3)	0.085 (3)	0.096 (3)	−0.014 (2)	−0.013 (2)	−0.044 (2)
C3	0.074 (2)	0.097 (3)	0.079 (3)	−0.014 (2)	−0.0163 (18)	−0.030 (2)
C4	0.0545 (17)	0.068 (2)	0.0558 (18)	−0.0078 (14)	−0.0072 (14)	−0.0133 (15)
C5	0.064 (2)	0.079 (2)	0.076 (2)	0.0047 (17)	−0.0257 (17)	−0.0060 (18)
C6	0.070 (2)	0.0572 (19)	0.091 (3)	0.0102 (15)	−0.0244 (19)	−0.0137 (18)
C7	0.0657 (19)	0.0527 (18)	0.078 (2)	0.0002 (15)	−0.0132 (17)	−0.0211 (16)
C8	0.0519 (17)	0.0595 (18)	0.0540 (18)	−0.0054 (14)	−0.0105 (14)	−0.0065 (14)
C9	0.0463 (15)	0.0481 (16)	0.0521 (17)	−0.0034 (12)	−0.0023 (13)	−0.0064 (13)
C10	0.070 (2)	0.066 (2)	0.102 (3)	0.0150 (16)	−0.0217 (19)	0.0055 (19)
C11	0.077 (2)	0.0518 (17)	0.068 (2)	−0.0134 (15)	−0.0130 (16)	−0.0142 (16)
C12	0.0634 (17)	0.0405 (15)	0.0569 (18)	−0.0102 (12)	−0.0069 (14)	−0.0161 (13)
C13	0.0656 (18)	0.0344 (14)	0.0603 (18)	−0.0057 (12)	−0.0091 (15)	−0.0109 (13)
C14	0.088 (2)	0.0467 (18)	0.073 (2)	−0.0078 (16)	−0.0168 (18)	−0.0117 (16)
N1	0.0581 (15)	0.0531 (15)	0.0690 (17)	−0.0041 (12)	−0.0024 (13)	−0.0080 (13)
N2	0.127 (3)	0.0699 (19)	0.091 (2)	−0.0243 (17)	−0.0265 (18)	−0.0361 (17)
N3	0.125 (3)	0.0481 (17)	0.131 (3)	0.0179 (17)	−0.039 (2)	−0.0167 (18)
Ni1	0.0547 (3)	0.0370 (3)	0.0474 (3)	−0.0059 (2)	−0.0121 (2)	−0.0100 (2)
O1	0.0821 (15)	0.0746 (15)	0.0849 (16)	0.0071 (11)	−0.0431 (13)	−0.0210 (13)
O2	0.0993 (17)	0.0704 (14)	0.0964 (18)	−0.0024 (12)	−0.0490 (14)	−0.0184 (13)
S1	0.0712 (5)	0.0514 (4)	0.0716 (5)	−0.0004 (3)	−0.0299 (4)	−0.0223 (4)
S2	0.0840 (6)	0.0460 (4)	0.0722 (5)	0.0070 (4)	−0.0361 (4)	−0.0195 (4)

C1—N1	1.319 (4)	C10—H10A	0.9599
C1—C2	1.374 (5)	C10—H10B	0.9599
C1—H1A	0.9600	C10—H10C	0.9600
C2—C3	1.351 (5)	C11—N2	1.135 (3)
C2—H2A	0.9599	C11—C12	1.430 (4)
C3—C4	1.399 (4)	C12—C13i	1.334 (4)
C3—H3A	0.9600	C12—S1	1.735 (3)
C4—C5	1.396 (4)	C13—C12i	1.334 (4)
C4—C9	1.416 (4)	C13—C14	1.424 (4)
C5—C6	1.343 (4)	C13—S2	1.733 (3)
C5—H5A	0.9600	C14—N3	1.138 (4)
C6—C7	1.395 (4)	Ni1—S2i	2.1546 (8)
C6—H6A	0.9600	Ni1—S2	2.1546 (8)
C7—C8	1.366 (4)	Ni1—S1	2.1599 (7)
C7—H7A	0.9600	Ni1—S1i	2.1599 (7)
C8—O1	1.340 (3)	O1—H1W	0.9789
C8—C9	1.408 (4)	O2—H2B	0.8500
C9—N1	1.383 (4)	O2—H2C	0.8500
C10—N1	1.492 (4)
N1—C1—C2	122.5 (3)	N1—C10—H10A	110.0
N1—C1—H1A	118.7	N1—C10—H10B	109.5
C2—C1—H1A	118.8	H10A—C10—H10B	109.5
C3—C2—C1	119.4 (3)	N1—C10—H10C	108.9
C3—C2—H2A	120.7	H10A—C10—H10C	109.5
C1—C2—H2A	119.8	H10B—C10—H10C	109.5
C2—C3—C4	119.9 (3)	N2—C11—C12	178.7 (4)
C2—C3—H3A	120.7	C13i—C12—C11	121.4 (3)
C4—C3—H3A	119.4	C13i—C12—S1	121.27 (19)
C5—C4—C3	120.0 (3)	C11—C12—S1	117.3 (2)
C5—C4—C9	120.6 (3)	C12i—C13—C14	122.4 (2)
C3—C4—C9	119.4 (3)	C12i—C13—S2	119.9 (2)
C6—C5—C4	120.2 (3)	C14—C13—S2	117.7 (2)
C6—C5—H5A	119.9	N3—C14—C13	179.1 (4)
C4—C5—H5A	119.9	C1—N1—C9	121.0 (3)
C5—C6—C7	119.8 (3)	C1—N1—C10	116.5 (3)
C5—C6—H6A	120.6	C9—N1—C10	122.6 (3)
C7—C6—H6A	119.6	S2i—Ni1—S2	180.00 (4)
C8—C7—C6	122.2 (3)	S2i—Ni1—S1	91.80 (3)
C8—C7—H7A	119.3	S2—Ni1—S1	88.20 (3)
C6—C7—H7A	118.6	S2i—Ni1—S1i	88.20 (3)
O1—C8—C7	120.8 (3)	S2—Ni1—S1i	91.80 (3)
O1—C8—C9	120.2 (3)	S1—Ni1—S1i	180.000 (1)
C7—C8—C9	119.0 (3)	C8—O1—H1W	111.5
N1—C9—C8	124.1 (3)	H2B—O2—H2C	109.5
N1—C9—C4	117.7 (3)	C12—S1—Ni1	103.10 (10)
C8—C9—C4	118.2 (3)	C13—S2—Ni1	103.92 (10)
N1—C1—C2—C3	0.2 (6)	C5—C4—C9—C8	1.4 (4)
C1—C2—C3—C4	2.5 (6)	C3—C4—C9—C8	−178.3 (2)
C2—C3—C4—C5	176.5 (3)	C2—C1—N1—C9	−1.6 (5)
C2—C3—C4—C9	−3.7 (5)	C2—C1—N1—C10	179.2 (3)
C3—C4—C5—C6	179.0 (3)	C8—C9—N1—C1	−179.0 (3)
C9—C4—C5—C6	−0.7 (5)	C4—C9—N1—C1	0.3 (4)
C4—C5—C6—C7	−0.7 (5)	C8—C9—N1—C10	0.2 (4)
C5—C6—C7—C8	1.3 (5)	C4—C9—N1—C10	179.5 (3)
C6—C7—C8—O1	178.9 (3)	C13i—C12—S1—Ni1	1.1 (3)
C6—C7—C8—C9	−0.6 (5)	C11—C12—S1—Ni1	−177.2 (2)
O1—C8—C9—N1	−0.9 (4)	S2i—Ni1—S1—C12	0.20 (10)
C7—C8—C9—N1	178.6 (3)	S2—Ni1—S1—C12	−179.80 (10)
O1—C8—C9—C4	179.8 (3)	C12i—C13—S2—Ni1	−2.0 (3)
C7—C8—C9—C4	−0.7 (4)	C14—C13—S2—Ni1	178.6 (2)
C5—C4—C9—N1	−178.0 (2)	S1—Ni1—S2—C13	−178.97 (10)
C3—C4—C9—N1	2.3 (4)	S1i—Ni1—S2—C13	1.03 (10)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1W···O2	0.98	1.66	2.639 (3)	180.
O2—H2B···S2	0.85	2.64	3.224 (3)	128.
O2—H2B···N2ii	0.85	2.51	2.948 (3)	113.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1W⋯O2	0.98	1.66	2.639 (3)	180
O2—H2B⋯S2	0.85	2.64	3.224 (3)	128
O2—H2B⋯N2i	0.85	2.51	2.948 (3)	113

Symmetry code: (i) .