Bis[1-(2,6-dichloro­benz­yl)-3-methyl­pyrazin-1-ium] bis­(maleonitrile­dithiol­ato)nickelate(II)

Yu, S.-S.; Xian, H.; Tian, Z.-F.

doi:10.1107/S1600536808034776

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page m1444

doi:10.1107/S1600536808034776

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Bis[1-(2,6-dichlorobenzyl)-3-methylpyrazin-1-ium] bis(maleonitriledithiolato)nickelate(II)

Shan-Shan Yu,^a Hua Xian ^a and Zheng-Fang Tian ^b ^*

^aDepartment of Chemistry, Nanjing Xiaozhuang College, Nanjing 210017, People's Republic of China, and ^bCollege of Chemistry and Applied Chemistry, Huanggang Normal University, Huanggang 438000, People's Republic of China
^*Correspondence e-mail: duanhaibao4660@163.com

(Received 14 October 2008; accepted 24 October 2008; online 31 October 2008)

In the crystal structure of the title compound, (C₁₂H₁₁Cl₂N₂)₂[Ni(C₄N₂S₂)₂], the Ni^II complex dianion is located on an inversion centre. The Ni^II atom is coordinated by four S atoms in a square-planar geometry. In the cation, the dihedral angle between the benzene and pyrazine rings is 85.2 (2)°.

Related literature

For general background, see: Ni et al. (2005 ); Nishijo et al. (2000 ); Robertson & Cronin (2002 ). For related structures, see: Ni et al. (2004 ); Ren et al. (2004 ).

Experimental

Crystal data

(C₁₂H₁₁Cl₂N₂)₂[Ni(C₄N₂S₂)₂]
M_r = 847.33
Monoclinic, P 2₁ /c
a = 9.081 (2) Å
b = 20.238 (5) Å
c = 10.489 (2) Å
β = 111.243 (4)°
V = 1796.6 (7) Å³
Z = 2
Mo Kα radiation
μ = 1.11 mm⁻¹
T = 298 (2) 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
8822 measured reflections
3159 independent reflections
2170 reflections with I > 2σ(I)
R_int = 0.086

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.114
S = 0.96
3159 reflections
224 parameters
H-atom parameters constrained
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.30 e Å⁻³

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/S1600536808034776/is2350sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808034776/is2350Isup2.hkl

checkCIF report

Comment top

Molecular solids based on transition metal dithiolene complexes have attracted intense interest in recent years, not only owing to the fundamental research of magnetic interactions and magneto-structural correlations but also to the development of new functional molecule-based materials (Robertson & Cronin, 2002). Much work has been performed in molecular solids based on M[dithiolene]₂ complexes owing to their application as building blocks in molecular-based materials showing magnetic, superconducting and optical properties (Nishijo et al., 2000; Ni et al., 2005). Herein, we report the crystal structure of the title compound, (I).

The molecular structure of (I) is illustrated in Fig. 1. Compound (I) crystallizes in monoclinic system, with one half [Ni(mnt)₂]^2- dianion and one 1-(2,6-dichlorobenzyl)-3-methylpyrazine cation in an asymmetric unit. The anion [Ni(mnt)₂]^2- possesses an approximated planar geometry and most of the bond lengths and angles are in good agreement with the various [Ni(mnt)₂]^2- compounds (Ni et al., 2004; Ren et al., 2004).

Related literature top

For general background, see: Ni et al. (2005); Nishijo et al. (2000); Robertson & Cronin (2002). For related structures, see: Ni et al. (2004); Ren et al. (2004).

Experimental top

Disodium maleonitriledithiolate (456 mg, 2.5 mmol) and nickel chloride hexahydrate (297 mg, 1.25 mmol) were mixed under stirring in water (20 mL) at room temperature. Subsequently, a solution of 1-(2,6-dichlorobenzyl)-3-methylpyrazine iodide (952 mg, 2.5 mmol) in methanol (10 mL) was added to the mixture. The black precipitate that was immediately formed was filtered off and washed with methanol. The crude product was recrystallized in acetone (20 mL) to give black block crystals. Anal. Calcd. for C₃₂H₂₂Cl₄N₈NiS₄: C 48.73, H 2.81, N 14.21%. Found: C 48.69, H 2.78, N 14.09%.

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 (I), showing the atom-numbering scheme and displacement ellipsoids at the 30% probability level. The suffix A corresponds to symmetry code (-x, -y+1, -z).

Bis[1-(2,6-dichlorobenzyl)-3-methylpyrazin-1-ium] bis(maleonitriledithiolato)nickelate(II) top

Crystal data top

(C₁₂H₁₁Cl₂N₂)₂[Ni(C₄N₂S₂)₂]	F(000) = 860
M_r = 847.33	D_x = 1.566 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 773 reflections
a = 9.081 (2) Å	θ = 2.6–21.2°
b = 20.238 (5) Å	µ = 1.11 mm⁻¹
c = 10.489 (2) Å	T = 298 K
β = 111.243 (4)°	Block, black
V = 1796.6 (7) Å³	0.30 × 0.20 × 0.20 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	3159 independent reflections
Radiation source: fine-focus sealed tube	2170 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.086
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→6
T_min = 0.732, T_max = 0.809	k = −24→23
8822 measured reflections	l = −12→12

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 0.96	w = 1/[σ²(F_o²) + (0.0362P)²] where P = (F_o² + 2F_c²)/3
3159 reflections	(Δ/σ)_max = 0.001
224 parameters	Δρ_max = 0.51 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

(C₁₂H₁₁Cl₂N₂)₂[Ni(C₄N₂S₂)₂]	V = 1796.6 (7) Å³
M_r = 847.33	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.081 (2) Å	µ = 1.11 mm⁻¹
b = 20.238 (5) Å	T = 298 K
c = 10.489 (2) Å	0.30 × 0.20 × 0.20 mm
β = 111.243 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3159 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2170 reflections with I > 2σ(I)
T_min = 0.732, T_max = 0.809	R_int = 0.086
8822 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 0.96	Δρ_max = 0.51 e Å⁻³
3159 reflections	Δρ_min = −0.30 e Å⁻³
224 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	0.0000	0.5000	0.0000	0.0410 (2)
C1	0.1965 (5)	0.45625 (18)	−0.1702 (4)	0.0434 (10)
C2	0.3109 (6)	0.45822 (19)	−0.2353 (5)	0.0475 (11)
C3	−0.0857 (5)	0.59184 (19)	0.1944 (4)	0.0445 (11)
C4	−0.0777 (5)	0.6476 (2)	0.2820 (5)	0.0489 (11)
C5	0.5497 (5)	0.67689 (19)	0.7483 (4)	0.0418 (10)
C6	0.4392 (5)	0.6850 (2)	0.6168 (5)	0.0508 (11)
C7	0.3690 (6)	0.7445 (3)	0.5682 (5)	0.0676 (14)
H7	0.2936	0.7477	0.4804	0.081*
C8	0.4110 (6)	0.7986 (2)	0.6501 (6)	0.0735 (16)
H8	0.3661	0.8394	0.6172	0.088*
C9	0.5185 (6)	0.7936 (2)	0.7801 (6)	0.0675 (14)
H9	0.5465	0.8309	0.8356	0.081*
C10	0.5857 (5)	0.7331 (2)	0.8293 (5)	0.0505 (12)
C11	0.6274 (5)	0.61171 (19)	0.7983 (4)	0.0486 (11)
H11A	0.6794	0.6130	0.8970	0.058*
H11B	0.5479	0.5772	0.7759	0.058*
C12	0.7394 (5)	0.53854 (19)	0.6677 (5)	0.0512 (12)
H12	0.6629	0.5071	0.6629	0.061*
C13	0.8486 (6)	0.5274 (2)	0.6073 (4)	0.0524 (12)
H13	0.8429	0.4881	0.5597	0.063*
C14	0.9720 (5)	0.6256 (2)	0.6865 (4)	0.0448 (10)
C15	0.8622 (5)	0.63866 (18)	0.7459 (4)	0.0408 (10)
H15	0.8696	0.6776	0.7949	0.049*
C16	1.1035 (5)	0.6723 (2)	0.7000 (5)	0.0666 (14)
H16A	1.2027	0.6502	0.7430	0.100*
H16B	1.0971	0.7094	0.7547	0.100*
H16C	1.0953	0.6874	0.6109	0.100*
Cl1	0.38504 (16)	0.61665 (7)	0.50983 (14)	0.0775 (4)
Cl2	0.71852 (16)	0.72925 (6)	0.99706 (13)	0.0719 (4)
N1	0.4021 (5)	0.46159 (18)	−0.2871 (4)	0.0651 (12)
N2	−0.0664 (5)	0.69443 (19)	0.3446 (4)	0.0688 (12)
N3	0.7460 (4)	0.59632 (15)	0.7340 (3)	0.0415 (9)
N4	0.9619 (4)	0.57012 (18)	0.6139 (4)	0.0535 (10)
S1	0.20391 (14)	0.51963 (5)	−0.05585 (12)	0.0484 (3)
S2	0.05266 (14)	0.59091 (5)	0.11563 (12)	0.0532 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0481 (5)	0.0298 (4)	0.0442 (5)	0.0004 (3)	0.0155 (4)	−0.0004 (3)
C1	0.053 (3)	0.030 (2)	0.048 (3)	0.002 (2)	0.018 (2)	0.0027 (18)
C2	0.058 (3)	0.031 (2)	0.054 (3)	−0.002 (2)	0.021 (3)	0.000 (2)
C3	0.054 (3)	0.034 (2)	0.047 (3)	0.005 (2)	0.020 (2)	−0.0004 (19)
C4	0.056 (3)	0.037 (3)	0.056 (3)	0.001 (2)	0.024 (2)	0.002 (2)
C5	0.040 (3)	0.036 (2)	0.057 (3)	−0.0008 (18)	0.027 (2)	0.006 (2)
C6	0.042 (3)	0.050 (3)	0.066 (3)	−0.005 (2)	0.027 (2)	0.005 (2)
C7	0.049 (3)	0.075 (4)	0.077 (4)	0.015 (3)	0.021 (3)	0.031 (3)
C8	0.075 (4)	0.045 (3)	0.113 (5)	0.025 (3)	0.049 (4)	0.021 (3)
C9	0.079 (4)	0.044 (3)	0.098 (4)	0.008 (3)	0.053 (3)	0.001 (3)
C10	0.051 (3)	0.045 (3)	0.066 (3)	0.005 (2)	0.034 (2)	0.005 (2)
C11	0.055 (3)	0.043 (2)	0.057 (3)	−0.001 (2)	0.031 (2)	0.005 (2)
C12	0.052 (3)	0.033 (2)	0.066 (3)	0.000 (2)	0.019 (2)	0.003 (2)
C13	0.059 (3)	0.041 (3)	0.054 (3)	0.005 (2)	0.016 (2)	−0.004 (2)
C14	0.042 (3)	0.046 (3)	0.046 (3)	0.001 (2)	0.015 (2)	0.003 (2)
C15	0.044 (3)	0.029 (2)	0.047 (3)	−0.0017 (19)	0.014 (2)	0.0026 (18)
C16	0.056 (3)	0.059 (3)	0.089 (4)	−0.011 (2)	0.032 (3)	−0.007 (3)
Cl1	0.0753 (10)	0.0753 (9)	0.0747 (10)	−0.0217 (7)	0.0185 (7)	−0.0094 (7)
Cl2	0.0806 (10)	0.0729 (9)	0.0635 (9)	−0.0026 (7)	0.0276 (7)	−0.0100 (6)
N1	0.070 (3)	0.052 (3)	0.083 (3)	−0.004 (2)	0.040 (3)	−0.001 (2)
N2	0.091 (3)	0.045 (2)	0.076 (3)	−0.004 (2)	0.036 (2)	−0.017 (2)
N3	0.046 (2)	0.0282 (19)	0.049 (2)	0.0030 (15)	0.0164 (17)	0.0058 (15)
N4	0.053 (3)	0.054 (2)	0.053 (2)	0.0067 (19)	0.0196 (19)	−0.0017 (19)
S1	0.0551 (8)	0.0365 (6)	0.0549 (8)	−0.0057 (5)	0.0214 (6)	−0.0049 (5)
S2	0.0621 (8)	0.0388 (6)	0.0658 (8)	−0.0115 (5)	0.0316 (6)	−0.0107 (5)

Geometric parameters (Å, º) top

Ni1—S2	2.1596 (11)	C8—H8	0.9300
Ni1—S2ⁱ	2.1596 (11)	C9—C10	1.382 (6)
Ni1—S1ⁱ	2.1715 (12)	C9—H9	0.9300
Ni1—S1	2.1715 (12)	C10—Cl2	1.737 (5)
C1—C3ⁱ	1.356 (5)	C11—N3	1.496 (5)
C1—C2	1.436 (6)	C11—H11A	0.9700
C1—S1	1.741 (4)	C11—H11B	0.9700
C2—N1	1.145 (5)	C12—N3	1.351 (5)
C3—C1ⁱ	1.356 (5)	C12—C13	1.375 (6)
C3—C4	1.441 (6)	C12—H12	0.9300
C3—S2	1.736 (4)	C13—N4	1.326 (5)
C4—N2	1.136 (5)	C13—H13	0.9300
C5—C10	1.387 (5)	C14—N4	1.341 (5)
C5—C6	1.391 (6)	C14—C15	1.379 (5)
C5—C11	1.498 (5)	C14—C16	1.489 (6)
C6—C7	1.370 (6)	C15—N3	1.330 (5)
C6—Cl1	1.737 (4)	C15—H15	0.9300
C7—C8	1.358 (7)	C16—H16A	0.9600
C7—H7	0.9300	C16—H16B	0.9600
C8—C9	1.363 (7)	C16—H16C	0.9600

S2—Ni1—S2ⁱ	180.00 (3)	C5—C10—Cl2	120.4 (3)
S2—Ni1—S1ⁱ	92.37 (4)	N3—C11—C5	110.5 (3)
S2ⁱ—Ni1—S1ⁱ	87.63 (4)	N3—C11—H11A	109.6
S2—Ni1—S1	87.63 (4)	C5—C11—H11A	109.6
S2ⁱ—Ni1—S1	92.37 (4)	N3—C11—H11B	109.6
S1ⁱ—Ni1—S1	180.0	C5—C11—H11B	109.6
C3ⁱ—C1—C2	123.1 (4)	H11A—C11—H11B	108.1
C3ⁱ—C1—S1	119.9 (3)	N3—C12—C13	118.3 (4)
C2—C1—S1	117.0 (3)	N3—C12—H12	120.8
N1—C2—C1	178.2 (4)	C13—C12—H12	120.8
C1ⁱ—C3—C4	123.0 (4)	N4—C13—C12	122.9 (4)
C1ⁱ—C3—S2	121.3 (3)	N4—C13—H13	118.5
C4—C3—S2	115.7 (3)	C12—C13—H13	118.5
N2—C4—C3	174.5 (5)	N4—C14—C15	120.4 (4)
C10—C5—C6	115.8 (4)	N4—C14—C16	118.2 (4)
C10—C5—C11	122.1 (4)	C15—C14—C16	121.4 (4)
C6—C5—C11	122.1 (4)	N3—C15—C14	120.9 (4)
C7—C6—C5	123.0 (4)	N3—C15—H15	119.6
C7—C6—Cl1	118.3 (4)	C14—C15—H15	119.6
C5—C6—Cl1	118.7 (3)	C14—C16—H16A	109.5
C8—C7—C6	119.1 (5)	C14—C16—H16B	109.5
C8—C7—H7	120.5	H16A—C16—H16B	109.5
C6—C7—H7	120.5	C14—C16—H16C	109.5
C7—C8—C9	120.6 (5)	H16A—C16—H16C	109.5
C7—C8—H8	119.7	H16B—C16—H16C	109.5
C9—C8—H8	119.7	C15—N3—C12	119.4 (4)
C8—C9—C10	119.9 (5)	C15—N3—C11	120.0 (3)
C8—C9—H9	120.0	C12—N3—C11	120.5 (3)
C10—C9—H9	120.0	C13—N4—C14	117.9 (4)
C9—C10—C5	121.6 (4)	C1—S1—Ni1	103.14 (15)
C9—C10—Cl2	118.0 (4)	C3—S2—Ni1	103.02 (14)

C10—C5—C6—C7	0.1 (6)	C16—C14—C15—N3	−179.5 (4)
C11—C5—C6—C7	−178.7 (4)	C14—C15—N3—C12	2.8 (6)
C10—C5—C6—Cl1	−178.9 (3)	C14—C15—N3—C11	−179.5 (4)
C11—C5—C6—Cl1	2.3 (5)	C13—C12—N3—C15	−3.9 (6)
C5—C6—C7—C8	1.6 (7)	C13—C12—N3—C11	178.4 (4)
Cl1—C6—C7—C8	−179.4 (4)	C5—C11—N3—C15	56.1 (5)
C6—C7—C8—C9	−1.7 (8)	C5—C11—N3—C12	−126.2 (4)
C7—C8—C9—C10	0.1 (8)	C12—C13—N4—C14	2.1 (6)
C8—C9—C10—C5	1.7 (7)	C15—C14—N4—C13	−3.3 (6)
C8—C9—C10—Cl2	−178.5 (4)	C16—C14—N4—C13	177.1 (4)
C6—C5—C10—C9	−1.7 (6)	C3ⁱ—C1—S1—Ni1	−4.5 (4)
C11—C5—C10—C9	177.1 (4)	C2—C1—S1—Ni1	175.2 (3)
C6—C5—C10—Cl2	178.5 (3)	S2—Ni1—S1—C1	−175.14 (14)
C11—C5—C10—Cl2	−2.7 (5)	S2ⁱ—Ni1—S1—C1	4.86 (14)
C10—C5—C11—N3	−105.5 (4)	C1ⁱ—C3—S2—Ni1	−2.9 (4)
C6—C5—C11—N3	73.2 (5)	C4—C3—S2—Ni1	179.2 (3)
N3—C12—C13—N4	1.5 (6)	S1ⁱ—Ni1—S2—C3	4.39 (15)
N4—C14—C15—N3	0.9 (6)	S1—Ni1—S2—C3	−175.61 (15)

Symmetry code: (i) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	(C₁₂H₁₁Cl₂N₂)₂[Ni(C₄N₂S₂)₂]
M_r	847.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	9.081 (2), 20.238 (5), 10.489 (2)
β (°)	111.243 (4)
V (Å³)	1796.6 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.11
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.732, 0.809
No. of measured, independent and observed [I > 2σ(I)] reflections	8822, 3159, 2170
R_int	0.086
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.114, 0.96
No. of reflections	3159
No. of parameters	224
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.30

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

Acknowledgements

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

References

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