Bis[(E)-1-(3,4-dichloro­benzyl­idene­amino)-4-methyl­pyridinium] bis­(maleonitrile­dithiol­ato)nickelate(II)

Liu, J.-L.; Yao, B.-Q.; Liu, Q.; Zhang, S.-M.

doi:10.1107/S1600536809001159

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 2| February 2009| Pages m203-m204

doi:10.1107/S1600536809001159

Open

access

Bis[(E)-1-(3,4-dichlorobenzylideneamino)-4-methylpyridinium] bis(maleonitriledithiolato)nickelate(II)

Jian-Lan Liu,^a Bing-Qian Yao,^a Qi Liu ^a and Shao-Ming Zhang ^a ^*

^aDepartment of Applied Chemistry, College of Sciences, Nanjing University of Technology, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: yaobq123@126.com

(Received 2 January 2009; accepted 10 January 2009; online 17 January 2009)

The asymmetric unit of the title compound, (C₁₃H₁₁Cl₂N₂)₂[Ni(C₄N₂S₂)₂], contains one-half of a centrosymmetric [Ni(mnt)₂] anion (where mnt is maleonitriledithiolate or 1,2-dicyano-1,2-ethylenedithiolate) and an (E)-1-(3,4-dichlorobenzylideneamino)-4-methylpyridinium cation. In the anion, the coordination around the Ni atom is a distorted square. In the cation, the aromatic rings are oriented at a dihedral angle of 7.81 (3)°. In the crystal structure, intermolecular C—H⋯N hydrogen bonds link the cations and anions. π–π Contacts between the nickel dithiolene and pyridine rings and between the benzene and pyridine rings, [centroid–centroid distances = 3.682 (3) and 3.643 (3) Å, respectively] may further stabilize the structure.

Related literature

For general background, see: Robertson & Cronin (2002 ); Cassoux et al. (1991 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

(C₁₃H₁₁Cl₂N₂)₂[Ni(C₄N₂S₂)₂]
M_r = 871.37
Monoclinic, P 2₁ /n
a = 10.7054 (10) Å
b = 13.8664 (13) Å
c = 12.5043 (12) Å
β = 95.803 (1)°
V = 1846.7 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.08 mm⁻¹
T = 296 (2) K
0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.729, T_max = 0.895
15877 measured reflections
4273 independent reflections
3611 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.089
S = 1.08
4273 reflections
232 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Ni1—S1	2.1622 (5)
Ni1—S2	2.1838 (5)

S1—Ni1—S2ⁱ	88.128 (19)
S1—Ni1—S2	91.872 (19)
Symmetry code: (i) -x+1, -y, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯N2ⁱⁱ	0.93	2.51	3.413 (3)	163
Symmetry code: (ii) x, y, z-1.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809001159/hk2608sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809001159/hk2608Isup2.hkl

checkCIF report

Comment top

Square-planar M[dithiolene]₂ complexes have attracted extensive interests in the areas of conducting and magnetic materials, dyes, non-linear optics and catalysis (Robertson et al., 2002; Cassoux et al., 1991). We report herein the crystal structure of the title compound.

The asymmetric unit of the title compound (Fig. 1) contains one-half of centrosymmetric [Ni(mnt)₂] (where mnt is maleonitriledithiolate) anion and a (E)-1-(3,4-di-chlorobenzylideneamino)-4-methylpyridinium cation. In the anion, the coordination around the Ni atom is a distorted square (Table 1). The bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (Ni1/S1/S2/C2/C3), B (N3/C5-C9) and C (C12-C17) are, of course, planar and they are oriented at dihedral angles of A/B = 16.69 (3)°, A/C = 13.47 (3)° and B/C = 7.81 (3)°.

In the crystal structure, intermolecular C-H···N hydrogen bonds (Table 2) link the cations and anions (Fig. 2), in which they may be effective in the stabilization of the structure. The π-π contacts between the nickel dithiolene and the pyridine rings and the benzene and the pyridine rings, Cg1—Cg3ⁱ and Cg3—Cg4ⁱⁱ [symmetry codes: (i) 1/2 + x, 1/2 - y, 1/2 + z; (ii) 1 - x, 1 - y, -z, where Cg1, Cg3 and Cg4 are centroids of the rings A (Ni1/S1/S2/C2/C3), B (N3/C5-C9) and C (C12-C17), respectively] may further stabilize the structure, with centroid-centroid distances of 3.682 (3) Å and 3.643 (3) Å.

Related literature top

For general background, see: Robertson et al. (2002); Cassoux et al. (1991). For bond-length data, see: Allen et al. (1987).

Experimental top

For the preparation of the title compound, disodium maleonitriledithiolate (458 mg, 2.46 mmol) and nickel chloride hexahydrate (230 mg, 0.96 mmol) were mixed by stirring in EtOH (20 ml) at room temperature. Subsequently, a solution of (E)-1-(3,4-di-chlorobenzylideneamino)-4-methylpyridinium iodide (2143 mg, 2.46 mmol) in EtOH (10 ml) was added to the mixture, and the red precipitate immediately formed was filtered off, and washed with EtOH. The crude product was recrystallized in acetone (20 ml) to give black crystals. Crystals suitable for X-ray analysis were obtained by diffusing diethyl ether into the solution of the title compound in acetone for 8 d. FT-IR data (KBr pellets, cm^-1): 2189 (s), 2920 (s),1631(s), 1485 (s), 1272 (s).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level [symmetry code (A): 1 - x, -y, 1 - z].
	Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

Bis[(E)-1-(3,4-dichlorobenzylideneamino)-4-methylpyridinium] bis(1,2-dicyano-1,2-ethylenedithiolato)nickelate(II) top

Crystal data top

(C₁₃H₁₁Cl₂N₂)₂[Ni(C₄N₂S₂)₂]	F(000) = 884
M_r = 871.37	D_x = 1.567 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3049 reflections
a = 10.7054 (10) Å	θ = 2.1–22.4°
b = 13.8664 (13) Å	µ = 1.08 mm⁻¹
c = 12.5043 (12) Å	T = 296 K
β = 95.803 (1)°	Block, black
V = 1846.7 (3) Å³	0.30 × 0.20 × 0.10 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	4273 independent reflections
Radiation source: fine-focus sealed tube	3611 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ϕ and ω scans	θ_max = 27.6°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −13→13
T_min = 0.729, T_max = 0.895	k = −18→18
15877 measured reflections	l = −13→16

Refinement top

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.089	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.044P)² + 0.5603P] where P = (F_o² + 2F_c²)/3
4273 reflections	(Δ/σ)_max = 0.001
232 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

(C₁₃H₁₁Cl₂N₂)₂[Ni(C₄N₂S₂)₂]	V = 1846.7 (3) Å³
M_r = 871.37	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.7054 (10) Å	µ = 1.08 mm⁻¹
b = 13.8664 (13) Å	T = 296 K
c = 12.5043 (12) Å	0.30 × 0.20 × 0.10 mm
β = 95.803 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4273 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	3611 reflections with I > 2σ(I)
T_min = 0.729, T_max = 0.895	R_int = 0.023
15877 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.089	H-atom parameters constrained
S = 1.08	Δρ_max = 0.44 e Å⁻³
4273 reflections	Δρ_min = −0.37 e Å⁻³
232 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Ni1	0.5000	0.0000	0.5000	0.03598 (10)
Cl1	0.39412 (8)	0.83968 (4)	0.09607 (5)	0.0739 (2)
Cl2	0.39194 (7)	0.91419 (4)	−0.14262 (5)	0.07117 (18)
S1	0.48602 (6)	0.12888 (4)	0.40218 (4)	0.05280 (15)
S2	0.48684 (5)	0.08311 (3)	0.64679 (4)	0.04583 (13)
N1	0.4615 (3)	0.38988 (15)	0.41030 (19)	0.0831 (7)
N2	0.4392 (2)	0.33492 (14)	0.73857 (16)	0.0663 (5)
N3	0.32151 (14)	0.36297 (10)	0.05354 (12)	0.0393 (3)
N4	0.34563 (15)	0.46221 (11)	0.03826 (13)	0.0449 (4)
C1	0.4621 (2)	0.31630 (15)	0.45077 (17)	0.0549 (5)
C2	0.46864 (18)	0.22060 (13)	0.49411 (16)	0.0446 (4)
C3	0.46740 (17)	0.20093 (13)	0.60048 (15)	0.0407 (4)
C4	0.45178 (19)	0.27570 (14)	0.67685 (16)	0.0477 (4)
C5	0.3192 (2)	0.29411 (15)	−0.02278 (18)	0.0543 (5)
H5A	0.3343	0.3101	−0.0925	0.065*
C6	0.2946 (2)	0.20068 (15)	0.0028 (2)	0.0584 (5)
H6A	0.2919	0.1537	−0.0505	0.070*
C7	0.27374 (19)	0.17458 (14)	0.10617 (19)	0.0517 (5)
C8	0.2804 (2)	0.24667 (15)	0.18250 (18)	0.0543 (5)
H8A	0.2682	0.2316	0.2532	0.065*
C9	0.3045 (2)	0.34025 (14)	0.15582 (16)	0.0487 (4)
H9A	0.3092	0.3880	0.2083	0.058*
C10	0.2459 (3)	0.07236 (16)	0.1355 (3)	0.0768 (8)
H10A	0.2449	0.0323	0.0728	0.115*
H10B	0.1656	0.0695	0.1631	0.115*
H10C	0.3096	0.0499	0.1893	0.115*
C11	0.32672 (19)	0.49507 (13)	−0.05590 (17)	0.0471 (4)
H11A	0.3002	0.4544	−0.1129	0.056*
C12	0.34690 (17)	0.59789 (13)	−0.07481 (16)	0.0428 (4)
C13	0.35970 (18)	0.66292 (14)	0.00916 (16)	0.0457 (4)
H13A	0.3585	0.6412	0.0794	0.055*
C14	0.37433 (18)	0.76020 (14)	−0.01073 (16)	0.0461 (4)
C15	0.37612 (18)	0.79287 (14)	−0.11577 (17)	0.0473 (4)
C16	0.3660 (2)	0.72771 (16)	−0.19945 (17)	0.0573 (5)
H16A	0.3692	0.7493	−0.2695	0.069*
C17	0.3511 (2)	0.63062 (16)	−0.18005 (17)	0.0553 (5)
H17A	0.3440	0.5871	−0.2369	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.04103 (18)	0.02949 (16)	0.03748 (18)	−0.00120 (12)	0.00426 (12)	0.00094 (12)
Cl1	0.1235 (6)	0.0405 (3)	0.0601 (3)	0.0083 (3)	0.0212 (3)	−0.0033 (2)
Cl2	0.0980 (5)	0.0409 (3)	0.0771 (4)	−0.0025 (3)	0.0212 (3)	0.0183 (3)
S1	0.0855 (4)	0.0343 (2)	0.0391 (3)	0.0037 (2)	0.0086 (2)	0.00337 (18)
S2	0.0636 (3)	0.0350 (2)	0.0393 (2)	−0.0017 (2)	0.0074 (2)	−0.00029 (18)
N1	0.129 (2)	0.0424 (11)	0.0774 (15)	0.0156 (12)	0.0078 (14)	0.0102 (10)
N2	0.0909 (15)	0.0513 (11)	0.0586 (11)	0.0040 (10)	0.0163 (10)	−0.0105 (9)
N3	0.0427 (8)	0.0299 (7)	0.0456 (8)	0.0002 (6)	0.0058 (6)	0.0016 (6)
N4	0.0546 (9)	0.0300 (7)	0.0506 (9)	−0.0035 (6)	0.0072 (7)	0.0025 (6)
C1	0.0731 (14)	0.0395 (10)	0.0513 (12)	0.0092 (9)	0.0023 (10)	−0.0002 (9)
C2	0.0484 (10)	0.0343 (9)	0.0507 (11)	0.0029 (7)	0.0038 (8)	0.0006 (8)
C3	0.0410 (9)	0.0337 (8)	0.0474 (10)	0.0007 (7)	0.0037 (7)	−0.0032 (7)
C4	0.0551 (11)	0.0401 (10)	0.0486 (11)	0.0005 (8)	0.0083 (9)	−0.0012 (8)
C5	0.0720 (14)	0.0424 (10)	0.0497 (11)	−0.0014 (9)	0.0127 (10)	−0.0057 (9)
C6	0.0685 (14)	0.0383 (10)	0.0690 (14)	−0.0025 (9)	0.0088 (11)	−0.0111 (10)
C7	0.0439 (10)	0.0328 (9)	0.0779 (15)	0.0005 (7)	0.0040 (10)	0.0047 (9)
C8	0.0662 (13)	0.0413 (10)	0.0564 (12)	0.0021 (9)	0.0112 (10)	0.0100 (9)
C9	0.0619 (12)	0.0366 (9)	0.0478 (11)	0.0017 (8)	0.0063 (9)	0.0018 (8)
C10	0.0816 (17)	0.0339 (11)	0.115 (2)	−0.0054 (10)	0.0105 (16)	0.0099 (12)
C11	0.0536 (11)	0.0383 (10)	0.0484 (11)	−0.0039 (8)	0.0008 (8)	0.0031 (8)
C12	0.0422 (9)	0.0382 (9)	0.0475 (10)	−0.0019 (7)	0.0020 (8)	0.0079 (8)
C13	0.0533 (11)	0.0405 (10)	0.0443 (10)	0.0052 (8)	0.0106 (8)	0.0083 (8)
C14	0.0498 (11)	0.0395 (9)	0.0500 (11)	0.0041 (8)	0.0104 (8)	0.0021 (8)
C15	0.0481 (10)	0.0377 (9)	0.0567 (11)	−0.0013 (8)	0.0075 (9)	0.0123 (8)
C16	0.0741 (14)	0.0539 (12)	0.0439 (11)	−0.0081 (10)	0.0063 (10)	0.0151 (9)
C17	0.0728 (14)	0.0482 (11)	0.0441 (11)	−0.0076 (10)	0.0020 (10)	0.0040 (9)

Geometric parameters (Å, º) top

Ni1—S1	2.1622 (5)	C6—H6A	0.9300
Ni1—S1ⁱ	2.1622 (5)	C7—C8	1.379 (3)
Ni1—S2ⁱ	2.1838 (5)	C7—C10	1.501 (3)
Ni1—S2	2.1838 (5)	C8—C9	1.371 (3)
Cl1—C14	1.728 (2)	C8—H8A	0.9300
Cl2—C15	1.7272 (19)	C9—H9A	0.9300
S1—C2	1.737 (2)	C10—H10A	0.9600
S2—C3	1.7388 (19)	C10—H10B	0.9600
N1—C1	1.139 (3)	C10—H10C	0.9600
N2—C4	1.144 (3)	C11—C12	1.465 (2)
N3—C9	1.347 (3)	C11—H11A	0.9300
N3—C5	1.349 (2)	C12—C13	1.380 (3)
N3—N4	1.417 (2)	C12—C17	1.397 (3)
N4—C11	1.260 (3)	C13—C14	1.383 (3)
C1—C2	1.432 (3)	C13—H13A	0.9300
C2—C3	1.359 (3)	C14—C15	1.391 (3)
C3—C4	1.431 (3)	C15—C16	1.378 (3)
C5—C6	1.366 (3)	C16—C17	1.380 (3)
C5—H5A	0.9300	C16—H16A	0.9300
C6—C7	1.383 (3)	C17—H17A	0.9300

S1—Ni1—S1ⁱ	180.0	C7—C8—H8A	119.5
S1—Ni1—S2ⁱ	88.128 (19)	N3—C9—C8	119.95 (19)
S1ⁱ—Ni1—S2ⁱ	91.873 (19)	N3—C9—H9A	120.0
S1—Ni1—S2	91.872 (19)	C8—C9—H9A	120.0
S1ⁱ—Ni1—S2	88.128 (19)	C7—C10—H10A	109.5
S2ⁱ—Ni1—S2	180.0	C7—C10—H10B	109.5
C2—S1—Ni1	103.69 (7)	H10A—C10—H10B	109.5
C3—S2—Ni1	103.39 (6)	C7—C10—H10C	109.5
C9—N3—C5	120.77 (17)	H10A—C10—H10C	109.5
C9—N3—N4	113.53 (15)	H10B—C10—H10C	109.5
C5—N3—N4	125.66 (16)	N4—C11—C12	119.38 (18)
C11—N4—N3	117.59 (16)	N4—C11—H11A	120.3
N1—C1—C2	175.0 (3)	C12—C11—H11A	120.3
C3—C2—C1	123.45 (18)	C13—C12—C17	119.61 (18)
C3—C2—S1	120.87 (14)	C13—C12—C11	121.19 (18)
C1—C2—S1	115.62 (15)	C17—C12—C11	119.19 (19)
C2—C3—C4	121.41 (17)	C12—C13—C14	120.30 (18)
C2—C3—S2	120.11 (14)	C12—C13—H13A	119.8
C4—C3—S2	118.47 (14)	C14—C13—H13A	119.8
N2—C4—C3	179.4 (2)	C13—C14—C15	119.98 (19)
N3—C5—C6	119.8 (2)	C13—C14—Cl1	119.36 (16)
N3—C5—H5A	120.1	C15—C14—Cl1	120.64 (15)
C6—C5—H5A	120.1	C16—C15—C14	119.72 (18)
C5—C6—C7	121.3 (2)	C16—C15—Cl2	119.51 (16)
C5—C6—H6A	119.3	C14—C15—Cl2	120.77 (16)
C7—C6—H6A	119.3	C15—C16—C17	120.50 (19)
C8—C7—C6	117.12 (18)	C15—C16—H16A	119.8
C8—C7—C10	120.9 (2)	C17—C16—H16A	119.8
C6—C7—C10	122.0 (2)	C16—C17—C12	119.9 (2)
C9—C8—C7	121.0 (2)	C16—C17—H17A	120.1
C9—C8—H8A	119.5	C12—C17—H17A	120.1

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···N2ⁱⁱ	0.93	2.51	3.413 (3)	163

Symmetry code: (ii) x, y, z−1.

Experimental details

Crystal data
Chemical formula	(C₁₃H₁₁Cl₂N₂)₂[Ni(C₄N₂S₂)₂]
M_r	871.37
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	10.7054 (10), 13.8664 (13), 12.5043 (12)
β (°)	95.803 (1)
V (Å³)	1846.7 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.08
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.729, 0.895
No. of measured, independent and observed [I > 2σ(I)] reflections	15877, 4273, 3611
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.089, 1.08
No. of reflections	4273
No. of parameters	232
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.37

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Ni1—S1	2.1622 (5)	Ni1—S2	2.1838 (5)

S1—Ni1—S2ⁱ	88.128 (19)	S1—Ni1—S2	91.872 (19)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···N2ⁱⁱ	0.93	2.51	3.413 (3)	163

Symmetry code: (ii) x, y, z−1.

Acknowledgements

The authors thank the Science and Technology Department of Jiangsu Province and the Natural Science Foundation of China for financial support (grant No. 10774076).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cassoux, P., Valade, L., Kobayashi, H., Kobayashi, A., Clark, R. A. & Underhill, A. E. (1991). Coord. Chem. Rev. 110, 115–160. CrossRef CAS Web of Science Google Scholar
Robertson, N. & Cronin, L. (2002). Coord. Chem. Rev. 227, 93–127. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 2| February 2009| Pages m203-m204

doi:10.1107/S1600536809001159

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Bis[(E)-1-(3,4-di­chloro­benzyl­­idene­amino)-4-methyl­pyridinium] bis­­(maleo­nitrile­di­thiol­ato)nickelate(II)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis[(E)-1-(3,4-dichlorobenzylideneamino)-4-methylpyridinium] bis(maleonitriledithiolato)nickelate(II)