1-Butyl­pyridinium bis­(1,2-dicyano­ethene-1,2-dithiol­ato)nickelate(III)

Duan, H.-B.

doi:10.1107/S1600536811042103

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page m1567

doi:10.1107/S1600536811042103

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1-Butylpyridinium bis(1,2-dicyanoethene-1,2-dithiolato)nickelate(III)

Hai-Bao Duan ^a ^*

^aSchool of Biochemical and Environmental Engineering, Nanjing Xiaozhuang College, Nanjing 210017, People's Republic of China
^*Correspondence e-mail: duanhaibao4660@163.com

(Received 5 October 2011; accepted 12 October 2011; online 22 October 2011)

The Ni^III atom in the anion of the title complex, (C₉H₁₄N)[Ni(C₄N₂S₂)₂], is coordinated by four S atoms of two maleonitriledithiolate ligands, and exhibits a square-planar coordination geometry.

Related literature

For background to designed functional materials, see: Nishijo et al. (2000 ); Robertson & Cronin (2002 ); Ni et al. (2005 ). For related structures, see: Ni et al. (2004 ); Ren et al. (2004 , 2008 ); Duan et al. (2010 ). For the synthesis of disodium maleonitriledithiolate and 1-butane-pyridinium bromide, see: Davison & Holm (1967 ); Yao et al. (2008 ).

Experimental

Crystal data

(C₉H₁₄N)[Ni(C₄N₂S₂)₂]
M_r = 475.30
Triclinic, $[P \overline 1]$
a = 9.2764 (11) Å
b = 9.9863 (11) Å
c = 12.7115 (15) Å
α = 81.695 (9)°
β = 75.882 (10)°
γ = 64.480 (11)°
V = 1029.5 (2) Å³
Z = 2
Cu Kα radiation
μ = 5.25 mm⁻¹
T = 293 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 = 0.559, T_max = 0.591
7461 measured reflections
3196 independent reflections
2499 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.109
S = 1.04
3196 reflections
245 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Selected bond lengths (Å)

Ni1—S1	2.1501 (8)
Ni1—S2	2.1436 (8)
Ni1—S3	2.1458 (8)
Ni1—S4	2.1461 (8)

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811042103/tk2798sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811042103/tk2798Isup2.hkl

checkCIF report

Comment top

Supramolecular chemistry and molecular crystal engineering, which is the planning and utilization of crystal-oriented syntheses for the bottom-up construction of functional molecular solids from molecules and ions, are powerful tools for the assembly of designed functional materials (Robertson & Cronin, 2002). Bis-1,2-dithiolene complexes of transition metals have been widely studied due to their novel properties and applications in the areas of near-infrared (near-IR) dyes, conducting, magnetic and non-linear optical materials (Nishijo et al., 2000; Ni et al., 2005). These applications arise due to a combination of functional properties, specific geometries and intermolecular interactions. Herein, we report the crystal structure of the title compound (I).

The molecular structure of (I) is illustrated in Fig. 1. and selected bond distances are given in Table 1. The asymmmetric units comprises one [Ni(mnt)₂]^- monoanion and one 1-butyl-pyridinium cation. The Ni ion in the [Ni(mnt)₂]^- anion is coordinated by four sulfur atoms of two mnt^2- ligands, and exhibits square-planar coordination geometry. The bond lengths in the anion are in good agreement with those found in other [Ni(mnt)₂]^- compounds (Ni et al., 2004; Ren et al., 2004; Duan et al., 2010; Ren et al., 2008).

Related literature top

For background to designed functional materials, see: Nishijo et al. (2000); Robertson & Cronin (2002); Ni et al. (2005). For related structures, see: Ni et al. (2004); Ren et al. (2004, 2008); Duan et al. (2010). For the synthesis of disodium maleonitriledithiolate and 1-butane-pyridinium bromide, see: Davison & Holm (1967); Yao et al. (2008).

Experimental top

All reagents and chemicals were purchased from commerical sources and used without further purification. The starting materials disodium maleonitriledithiolate (Davison et al., 1967) and 1-butyl-pyridinium bromide (Yao et al., 2008) were synthesized following the literature procedures. 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-butyl-pyridinium bromide (1.5 mmol) in methanol (10 ml) was added to the mixture. The red precipitate that was immediately formed was filtered off and washed with methanol. Then, a methanol solution of I₂ (205 mg, 0.8 mmol) was added slowly. After stirring for 40 minutes, the mixture was allowed to stand overnight. The microcrystals formed were recrystallized from acetone to give black blocks.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structures of the ionic components of (I), showing the atom-numbering scheme and displacement ellipsoids at the 30% probability level.

1-Butylpyridinium bis(1,2-dicyanoethene-1,2-dithiolato)nicklate(III) top

Crystal data top

(C₉H₁₄N)[Ni(C₄N₂S₂)₂]	V = 1029.5 (2) Å³
M_r = 475.30	Z = 2
Triclinic, P1	F(000) = 486
Hall symbol: -P 1	D_x = 1.533 Mg m⁻³
a = 9.2764 (11) Å	Cu Kα radiation, λ = 1.54178 Å
b = 9.9863 (11) Å	µ = 5.25 mm⁻¹
c = 12.7115 (15) Å	T = 293 K
α = 81.695 (9)°	Block, black
β = 75.882 (10)°	0.3 × 0.1 × 0.1 mm
γ = 64.480 (11)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3196 independent reflections
Radiation source: fine-focus sealed tube	2499 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ϕ and ω scans	θ_max = 62.6°, θ_min = 3.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −10→9
T_min = 0.559, T_max = 0.591	k = −11→11
7461 measured reflections	l = −14→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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0752P)²] where P = (F_o² + 2F_c²)/3
3196 reflections	(Δ/σ)_max < 0.001
245 parameters	Δρ_max = 0.36 e Å⁻³
1 restraint	Δρ_min = −0.33 e Å⁻³

Crystal data top

(C₉H₁₄N)[Ni(C₄N₂S₂)₂]	γ = 64.480 (11)°
M_r = 475.30	V = 1029.5 (2) Å³
Triclinic, P1	Z = 2
a = 9.2764 (11) Å	Cu Kα radiation
b = 9.9863 (11) Å	µ = 5.25 mm⁻¹
c = 12.7115 (15) Å	T = 293 K
α = 81.695 (9)°	0.3 × 0.1 × 0.1 mm
β = 75.882 (10)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3196 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	2499 reflections with I > 2σ(I)
T_min = 0.559, T_max = 0.591	R_int = 0.018
7461 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	1 restraint
wR(F²) = 0.109	H-atom parameters constrained
S = 1.04	Δρ_max = 0.36 e Å⁻³
3196 reflections	Δρ_min = −0.33 e Å⁻³
245 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	0.17351 (5)	0.21297 (4)	0.32522 (3)	0.05459 (18)
S1	−0.01043 (8)	0.19088 (7)	0.45807 (6)	0.0601 (2)
S2	0.04693 (8)	0.45024 (7)	0.31675 (6)	0.0634 (2)
S3	0.34944 (8)	0.23715 (8)	0.18766 (6)	0.0646 (2)
S4	0.30030 (9)	−0.02462 (7)	0.33157 (6)	0.0681 (2)
N1	−0.3268 (3)	0.7577 (3)	0.4479 (2)	0.0791 (7)
N2	−0.4145 (3)	0.4193 (3)	0.6218 (2)	0.0862 (8)
N3	0.6747 (3)	−0.3235 (3)	0.1797 (2)	0.0886 (8)
N4	0.7294 (3)	0.0134 (3)	0.0023 (2)	0.0882 (8)
N5	0.1415 (3)	0.7746 (2)	0.81191 (17)	0.0575 (5)
C1	−0.2966 (3)	0.3967 (3)	0.5591 (2)	0.0611 (7)
C2	−0.1507 (3)	0.3709 (3)	0.4772 (2)	0.0531 (6)
C3	−0.2387 (3)	0.6364 (3)	0.4331 (2)	0.0599 (7)
C4	−0.1257 (3)	0.4844 (3)	0.4169 (2)	0.0550 (6)
C5	0.6208 (3)	0.0325 (3)	0.0733 (2)	0.0652 (7)
C6	0.4856 (3)	0.0568 (3)	0.1630 (2)	0.0565 (6)
C7	0.4645 (3)	−0.0567 (3)	0.2251 (2)	0.0569 (6)
C8	0.5794 (3)	−0.2072 (3)	0.2023 (2)	0.0659 (7)
C9	0.2814 (3)	0.6993 (3)	0.7434 (2)	0.0650 (7)
H9	0.3298	0.5961	0.7497	0.078*
C10	0.3530 (4)	0.7722 (3)	0.6651 (2)	0.0731 (8)
H10	0.4497	0.7186	0.6182	0.088*
C11	0.2837 (4)	0.9231 (4)	0.6549 (2)	0.0777 (9)
H11	0.3331	0.9734	0.6020	0.093*
C12	0.1386 (4)	1.0006 (3)	0.7248 (3)	0.0782 (9)
H12	0.0884	1.1037	0.7190	0.094*
C13	0.0705 (4)	0.9233 (3)	0.8022 (2)	0.0686 (8)
H13	−0.0272	0.9748	0.8491	0.082*
C14	0.0666 (4)	0.6954 (3)	0.8999 (2)	0.0675 (7)
H14A	0.1108	0.5915	0.8837	0.081*
H14B	−0.0502	0.7374	0.9038	0.081*
C15	0.0995 (4)	0.7078 (4)	1.0100 (2)	0.0785 (9)
H15A	0.0642	0.8119	1.0222	0.094*
H15B	0.0340	0.6697	1.0668	0.094*
C16	0.2730 (4)	0.6270 (4)	1.0199 (3)	0.0827 (9)
H16A	0.3399	0.6628	0.9625	0.099*
H16B	0.3082	0.5220	1.0108	0.099*
C17	0.2978 (4)	0.6479 (4)	1.1299 (3)	0.0867 (10)
H17A	0.2674	0.7513	1.1377	0.130*
H17B	0.4104	0.5924	1.1341	0.130*
H17C	0.2311	0.6131	1.1868	0.130*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0448 (3)	0.0471 (3)	0.0603 (3)	−0.0124 (2)	−0.0012 (2)	−0.0050 (2)
S1	0.0525 (4)	0.0452 (4)	0.0670 (4)	−0.0135 (3)	0.0015 (3)	−0.0008 (3)
S2	0.0567 (4)	0.0489 (4)	0.0689 (4)	−0.0174 (3)	0.0060 (3)	−0.0021 (3)
S3	0.0525 (4)	0.0501 (4)	0.0736 (4)	−0.0146 (3)	0.0055 (3)	−0.0022 (3)
S4	0.0579 (4)	0.0488 (4)	0.0742 (5)	−0.0127 (3)	0.0096 (4)	−0.0021 (3)
N1	0.0769 (17)	0.0505 (15)	0.0934 (19)	−0.0155 (13)	−0.0048 (14)	−0.0097 (13)
N2	0.0728 (18)	0.0701 (17)	0.0859 (18)	−0.0194 (14)	0.0192 (15)	−0.0071 (14)
N3	0.0788 (18)	0.0535 (16)	0.103 (2)	−0.0110 (14)	0.0082 (15)	−0.0122 (14)
N4	0.0702 (18)	0.0761 (18)	0.0905 (19)	−0.0213 (14)	0.0174 (16)	−0.0071 (15)
N5	0.0505 (12)	0.0568 (13)	0.0561 (12)	−0.0137 (10)	−0.0055 (10)	−0.0116 (10)
C1	0.0588 (17)	0.0468 (14)	0.0640 (16)	−0.0144 (12)	−0.0012 (14)	−0.0049 (12)
C2	0.0487 (14)	0.0487 (14)	0.0529 (13)	−0.0139 (11)	−0.0031 (12)	−0.0079 (11)
C3	0.0610 (17)	0.0499 (17)	0.0608 (15)	−0.0200 (13)	−0.0031 (13)	−0.0034 (12)
C4	0.0512 (15)	0.0477 (14)	0.0581 (14)	−0.0143 (11)	−0.0040 (12)	−0.0104 (12)
C5	0.0555 (17)	0.0548 (16)	0.0709 (18)	−0.0164 (13)	0.0016 (15)	−0.0049 (13)
C6	0.0425 (14)	0.0557 (15)	0.0617 (15)	−0.0135 (11)	−0.0023 (12)	−0.0097 (12)
C7	0.0469 (14)	0.0512 (15)	0.0615 (15)	−0.0125 (12)	−0.0024 (12)	−0.0091 (12)
C8	0.0583 (17)	0.0542 (17)	0.0709 (17)	−0.0181 (14)	0.0033 (14)	−0.0048 (14)
C9	0.0559 (17)	0.0590 (16)	0.0660 (17)	−0.0105 (13)	−0.0073 (14)	−0.0122 (14)
C10	0.0630 (18)	0.075 (2)	0.0645 (17)	−0.0190 (16)	0.0043 (15)	−0.0130 (15)
C11	0.086 (2)	0.081 (2)	0.0653 (17)	−0.0384 (18)	−0.0079 (17)	0.0008 (16)
C12	0.090 (2)	0.0564 (17)	0.0769 (19)	−0.0210 (16)	−0.0151 (18)	−0.0030 (15)
C13	0.0653 (18)	0.0539 (16)	0.0689 (17)	−0.0092 (14)	−0.0057 (15)	−0.0130 (14)
C14	0.0621 (18)	0.0705 (18)	0.0689 (17)	−0.0297 (15)	−0.0060 (14)	−0.0053 (14)
C15	0.072 (2)	0.078 (2)	0.0735 (18)	−0.0302 (16)	0.0003 (16)	0.0052 (16)
C16	0.083 (2)	0.071 (2)	0.082 (2)	−0.0255 (17)	−0.0114 (18)	0.0043 (16)
C17	0.096 (2)	0.093 (2)	0.079 (2)	−0.046 (2)	−0.0262 (19)	0.0118 (18)

Geometric parameters (Å, º) top

Ni1—S1	2.1501 (8)	C9—C10	1.359 (4)
Ni1—S2	2.1436 (8)	C9—H9	0.9300
Ni1—S3	2.1458 (8)	C10—C11	1.361 (4)
Ni1—S4	2.1461 (8)	C10—H10	0.9300
S1—C2	1.715 (2)	C11—C12	1.384 (4)
S2—C4	1.721 (3)	C11—H11	0.9300
S3—C6	1.717 (3)	C12—C13	1.364 (4)
S4—C7	1.719 (3)	C12—H12	0.9300
N1—C3	1.145 (3)	C13—H13	0.9300
N2—C1	1.139 (4)	C14—C15	1.536 (4)
N3—C8	1.141 (4)	C14—H14A	0.9700
N4—C5	1.143 (3)	C14—H14B	0.9700
N5—C13	1.341 (4)	C15—C16	1.485 (4)
N5—C9	1.344 (3)	C15—H15A	0.9700
N5—C14	1.483 (3)	C15—H15B	0.9700
C1—C2	1.439 (4)	C16—C17	1.527 (5)
C2—C4	1.348 (4)	C16—H16A	0.9700
C3—C4	1.435 (4)	C16—H16B	0.9700
C5—C6	1.432 (4)	C17—H17A	0.9600
C6—C7	1.343 (4)	C17—H17B	0.9600
C7—C8	1.440 (4)	C17—H17C	0.9600

S2—Ni1—S3	86.97 (3)	C11—C10—H10	119.8
S2—Ni1—S4	179.28 (3)	C10—C11—C12	118.9 (3)
S3—Ni1—S4	92.59 (3)	C10—C11—H11	120.6
S2—Ni1—S1	92.34 (3)	C12—C11—H11	120.6
S3—Ni1—S1	177.33 (3)	C13—C12—C11	119.0 (3)
S4—Ni1—S1	88.08 (3)	C13—C12—H12	120.5
C2—S1—Ni1	103.03 (9)	C11—C12—H12	120.5
C4—S2—Ni1	103.36 (9)	N5—C13—C12	121.3 (3)
C6—S3—Ni1	102.87 (10)	N5—C13—H13	119.3
C7—S4—Ni1	102.92 (9)	C12—C13—H13	119.3
C13—N5—C9	119.7 (3)	N5—C14—C15	111.1 (2)
C13—N5—C14	119.5 (2)	N5—C14—H14A	109.4
C9—N5—C14	120.7 (2)	C15—C14—H14A	109.4
N2—C1—C2	178.1 (3)	N5—C14—H14B	109.4
C4—C2—C1	121.1 (2)	C15—C14—H14B	109.4
C4—C2—S1	121.02 (19)	H14A—C14—H14B	108.0
C1—C2—S1	117.88 (19)	C16—C15—C14	114.5 (3)
N1—C3—C4	178.3 (3)	C16—C15—H15A	108.6
C2—C4—C3	122.3 (2)	C14—C15—H15A	108.6
C2—C4—S2	120.21 (19)	C16—C15—H15B	108.6
C3—C4—S2	117.5 (2)	C14—C15—H15B	108.6
N4—C5—C6	179.3 (3)	H15A—C15—H15B	107.6
C7—C6—C5	121.6 (2)	C15—C16—C17	111.7 (3)
C7—C6—S3	120.9 (2)	C15—C16—H16A	109.3
C5—C6—S3	117.5 (2)	C17—C16—H16A	109.3
C6—C7—C8	120.0 (2)	C15—C16—H16B	109.3
C6—C7—S4	120.7 (2)	C17—C16—H16B	109.3
C8—C7—S4	119.3 (2)	H16A—C16—H16B	107.9
N3—C8—C7	176.4 (3)	C16—C17—H17A	109.5
N5—C9—C10	120.7 (3)	C16—C17—H17B	109.5
N5—C9—H9	119.6	H17A—C17—H17B	109.5
C10—C9—H9	119.6	C16—C17—H17C	109.5
C9—C10—C11	120.3 (3)	H17A—C17—H17C	109.5
C9—C10—H10	119.8	H17B—C17—H17C	109.5

Experimental details

Crystal data
Chemical formula	(C₉H₁₄N)[Ni(C₄N₂S₂)₂]
M_r	475.30
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.2764 (11), 9.9863 (11), 12.7115 (15)
α, β, γ (°)	81.695 (9), 75.882 (10), 64.480 (11)
V (Å³)	1029.5 (2)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	5.25
Crystal size (mm)	0.3 × 0.1 × 0.1

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2002)
T_min, T_max	0.559, 0.591
No. of measured, independent and observed [I > 2σ(I)] reflections	7461, 3196, 2499
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.576

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.109, 1.04
No. of reflections	3196
No. of parameters	245
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.33

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

Selected bond lengths (Å) top

Ni1—S1	2.1501 (8)	Ni1—S3	2.1458 (8)
Ni1—S2	2.1436 (8)	Ni1—S4	2.1461 (8)

Acknowledgements

The author thanks the Nanjing Xiaozhuang College of Jiangsu Province, P. R. China, for financial support (grant No. 2010KYQN28).

References

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