1-(2,4-Dichloro­benz­yl)pyridinium bis­(2-sulfanyl­idene-1,3-dithiole-4,5-dithiol­ato-κ2S,S′)nickelate(III)

Liu, G.-X.

doi:10.1107/S1600536811045004

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page m1654

https://doi.org/10.1107/S1600536811045004

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1-(2,4-Dichlorobenzyl)pyridinium bis(2-sulfanylidene-1,3-dithiole-4,5-dithiolato-κ²S,S′)nickelate(III)

Guang-Xiang Liu ^a ^*

^aDepartment of Chemistry, Nanjing Xiaozhuang University, Nanjing 211171, People's Republic of China
^*Correspondence e-mail: njuliugx@gmail.com

(Received 7 October 2011; accepted 27 October 2011; online 2 November 2011)

In the title compound, (C₁₂H₁₀Cl₂N)[Ni(C₃S₅)₂], the Ni^III atom is chelated by two bidentate 2-sulfanylidene-1,3-dithiole-4,5-dithiolate (dmit) dianions and shows a distorted square-planar geometry. The two dmit ligands are twisted with respect to each other by 3.21 (2)°. In the cation, the two aromatic groups linked by the methylene bridging group form a dihedral angle of 68.09 (2)°. S⋯S [3.6212 (11) and 3.5573 (9) Å] and Ni⋯S [3.566 (2)Å] interactions influence the arrangement of the anions in the crystal.

Related literature

For potential applications of bis(dithiolate)-metal complexes, see: Cassoux (1999 ). For the oxidation of Ni^II compounds, see: Cassoux et al. (1991 ). For the synthesis, see: Wang et al. (1998 ).

Experimental

Crystal data

(C₁₂H₁₀Cl₂N)[Ni(C₃S₅)₂]
M_r = 690.48
Monoclinic, P 2₁ /c
a = 14.4614 (5) Å
b = 8.2158 (3) Å
c = 21.8894 (8) Å
β = 107.231 (1)°
V = 2484.00 (15) Å³
Z = 4
Mo Kα radiation
μ = 1.85 mm⁻¹
T = 293 K
0.26 × 0.12 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.645, T_max = 0.837
18903 measured reflections
4615 independent reflections
3992 reflections with I > 2σ(I)
R_int = 0.085

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.092
S = 1.04
4615 reflections
290 parameters
H-atom parameters constrained
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.69 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 I, global. DOI: https://doi.org/10.1107/S1600536811045004/gk2414sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811045004/gk2414Isup2.hkl

checkCIF report

Comment top

The bis(dithiolate)-metal complexes and their analogues with interesting structures and/or potential applications such as conducting/magnetic or non-linear optical (NLO) materials have been reported in recent years (Cassoux, 1999). We report herein the crystal structure of the title bis-dithiolate-metal complex. In this compound, the Ni^II cations of NiCl₂.6H₂O have been oxidized to Ni^IIIcation by I₃^- (Cassoux et al., 1991). The Ni^IIIcation is coordinated with two dmit^2- anions. As shown in Fig. 1, the asymmetric unit of the title compound contains one [Ni(dmit)₂]^- anion and one [DiClPy]+ cation. Each nickel(III) ion is coordinated by four S atoms from two dmit ligands to complete a square-planar geometry, with Ni—S bond lengths ranging from 2.1589 (7) to 2.1640 (7) Å. The [Ni(dmit)₂]^- anions related by inversion center form dimers with the S atom of one anion placed directly above the Ni atom of another anion with Ni···S distance of 3.566 (2)Å (Ni1···S2^i:symmetry code: (i) -x, -y, -z], indicating the existence of electrostatic Ni···S interactions. The dimers linked through S3···S5ⁱⁱ [3.6212 (11)Å] and S4···S8ⁱⁱⁱ [3.5573 (9)Å] [symmetry code: (ii) -x, 1/2 + y, 1/2 - z; (iii) x, 1/2 - y;1/2 + z] interactions form a two-dimensional layer structure, as depicted in Fig 2. The (C₁₂H₁₀Cl₂N)⁺ cation adopts a Λ-shaped conformation, and the dihedral angles formed by the C12/C13/N1 plane with the benzene and pyridinium rings are 76.44 (2) and 86.75 (2)°, respectively.

Related literature top

For potential applications of bis(dithiolate)-metal complexes, see: Cassoux (1999). For the oxidation of Ni^II compounds, see: Cassoux et al. (1991). For the synthesis, see: Wang et al. (1998).

Experimental top

4,5-Di(thiobenzoyl)-1,3-dithiole-2-thione (812 mg, 2 mmol) was suspended in methanol (10 ml). Sodium methoxide in methanol (prepared form 184 mg of sodium in 10 ml of methanol) was added to the above mixture under argon atmosphere at room temperature from 30 min to give a dark red solution. To this solution, NiCl₂.6H₂O (238 mg, 1 mmol) was added. After 30 min, a solution of I₂ (127 mg, 1 mmol) and NaI (150 mg, 1 mmol) in methanol (20 ml) was added (the monoanionic [Ni(dmit)₂]^- are obtained from the dianionic [Ni(dmit)₂]^2- by I₃^- oxidation). After another 10 min, a solution of 1-(2,4-dichlorobenzyl)pyridinium bromide [(DiClPy)Br] (317 mg, 1 mmol) in methanol (20 ml) was added to the reaction mixture. The solution was stirred for 30 min and cooled in a refrigerator overnight. The resultant dark green crystal was collected by filtration, and purified by recrystallization using a mixed solvent of acetonitrile and benzene.

Structure description top

For potential applications of bis(dithiolate)-metal complexes, see: Cassoux (1999). For the oxidation of Ni^II compounds, see: Cassoux et al. (1991). For the synthesis, see: Wang et al. (1998).

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 cation and anion in the title compound with displacement ellipsoids drawn at the30% probability level. Hydrogen atoms have been omitted for clarity.
	Fig. 2. Two-dimensional supramolecular structure of [Ni(dmit)₂]- anions through S···S and Ni···S contacts. Dashed lines indicate weak interactions.

1-(2,4-Dichlorobenzyl)pyridinium bis(2-sulfanylidene-1,3-dithiole- 4,5-dithiolato-κ²S,S')nickelate(III) top

Crystal data top

(C₁₂H₁₀Cl₂N)[Ni(C₃S₅)₂]	F(000) = 1388
M_r = 690.48	D_x = 1.846 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9920 reflections
a = 14.4614 (5) Å	θ = 2.7–27.6°
b = 8.2158 (3) Å	µ = 1.85 mm⁻¹
c = 21.8894 (8) Å	T = 293 K
β = 107.231 (1)°	Needle, black
V = 2484.00 (15) Å³	0.26 × 0.12 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4615 independent reflections
Radiation source: sealed tube	3992 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.085
phi and ω scans	θ_max = 25.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −14→17
T_min = 0.645, T_max = 0.837	k = −9→9
18903 measured reflections	l = −26→26

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.034	H-atom parameters constrained
wR(F²) = 0.092	w = 1/[σ²(F_o²) + (0.0486P)² + 0.8363P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
4615 reflections	Δρ_max = 0.59 e Å⁻³
290 parameters	Δρ_min = −0.69 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0070 (5)

Crystal data top

(C₁₂H₁₀Cl₂N)[Ni(C₃S₅)₂]	V = 2484.00 (15) Å³
M_r = 690.48	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.4614 (5) Å	µ = 1.85 mm⁻¹
b = 8.2158 (3) Å	T = 293 K
c = 21.8894 (8) Å	0.26 × 0.12 × 0.10 mm
β = 107.231 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4615 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	3992 reflections with I > 2σ(I)
T_min = 0.645, T_max = 0.837	R_int = 0.085
18903 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.092	H-atom parameters constrained
S = 1.04	Δρ_max = 0.59 e Å⁻³
4615 reflections	Δρ_min = −0.69 e Å⁻³
290 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	0.11672 (2)	0.16527 (4)	0.035816 (14)	0.03166 (12)
S1	0.17227 (5)	−0.00117 (9)	0.11477 (3)	0.03781 (17)
S2	−0.02108 (5)	0.18995 (9)	0.05446 (3)	0.04024 (18)
S3	−0.10016 (4)	0.02836 (9)	0.15211 (3)	0.03853 (18)
S4	0.07706 (5)	−0.14743 (9)	0.20813 (3)	0.03956 (18)
S5	−0.07945 (6)	−0.17259 (11)	0.26887 (4)	0.0588 (2)
S6	0.25347 (5)	0.13324 (9)	0.01601 (3)	0.04044 (18)
S7	0.06384 (5)	0.33985 (9)	−0.04061 (3)	0.03918 (18)
S8	0.15951 (5)	0.48291 (9)	−0.13470 (3)	0.04262 (19)
S9	0.33185 (5)	0.28997 (9)	−0.08385 (3)	0.04294 (19)
S10	0.31807 (6)	0.49623 (10)	−0.19673 (4)	0.0494 (2)
C1	0.07448 (18)	−0.0249 (3)	0.14306 (11)	0.0311 (5)
C2	−0.00959 (17)	0.0580 (3)	0.11635 (11)	0.0319 (5)
C3	−0.03719 (18)	−0.1004 (3)	0.21241 (12)	0.0372 (6)
C4	0.24237 (18)	0.2678 (3)	−0.04584 (11)	0.0337 (5)
C5	0.16105 (18)	0.3563 (3)	−0.07046 (11)	0.0326 (5)
C6	0.27173 (19)	0.4270 (3)	−0.14143 (12)	0.0375 (6)
C7	0.47163 (18)	0.4200 (3)	0.30763 (12)	0.0369 (6)
C8	0.5031 (2)	0.5037 (3)	0.36482 (13)	0.0424 (7)
H8	0.5673	0.4975	0.3900	0.051*
C9	0.4369 (2)	0.5968 (4)	0.38364 (13)	0.0427 (6)
C10	0.3420 (2)	0.6087 (4)	0.34687 (14)	0.0459 (7)
H10	0.2983	0.6730	0.3599	0.055*
C11	0.3131 (2)	0.5234 (4)	0.29039 (14)	0.0452 (7)
H11	0.2489	0.5314	0.2653	0.054*
C12	0.37567 (19)	0.4262 (3)	0.26942 (12)	0.0378 (6)
C13	0.3383 (2)	0.3300 (3)	0.20858 (13)	0.0446 (7)
H13A	0.3840	0.2442	0.2077	0.054*
H13B	0.2773	0.2793	0.2076	0.054*
C14	0.3970 (2)	0.4626 (4)	0.12692 (14)	0.0505 (7)
H14	0.4570	0.4154	0.1461	0.061*
C15	0.3849 (3)	0.5594 (5)	0.07450 (15)	0.0648 (9)
H15	0.4362	0.5777	0.0579	0.078*
C16	0.2968 (4)	0.6292 (5)	0.04666 (16)	0.0733 (11)
H16	0.2878	0.6969	0.0113	0.088*
C17	0.2219 (3)	0.5989 (4)	0.07112 (16)	0.0687 (11)
H17	0.1614	0.6451	0.0522	0.082*
C18	0.2361 (2)	0.5005 (4)	0.12343 (15)	0.0533 (8)
H18	0.1851	0.4790	0.1400	0.064*
Cl1	0.55699 (6)	0.30754 (10)	0.28410 (4)	0.0559 (2)
Cl2	0.47396 (7)	0.70086 (12)	0.45557 (4)	0.0695 (3)
N1	0.32373 (16)	0.4347 (3)	0.15097 (10)	0.0396 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.02757 (19)	0.0410 (2)	0.02521 (18)	0.00030 (13)	0.00600 (13)	0.00174 (13)
S1	0.0295 (3)	0.0497 (4)	0.0341 (3)	0.0068 (3)	0.0091 (3)	0.0074 (3)
S2	0.0306 (3)	0.0546 (4)	0.0353 (3)	0.0089 (3)	0.0092 (3)	0.0151 (3)
S3	0.0270 (3)	0.0512 (4)	0.0370 (4)	0.0023 (3)	0.0087 (3)	0.0107 (3)
S4	0.0352 (4)	0.0480 (4)	0.0353 (3)	0.0090 (3)	0.0100 (3)	0.0125 (3)
S5	0.0494 (5)	0.0755 (6)	0.0598 (5)	0.0147 (4)	0.0289 (4)	0.0336 (4)
S6	0.0314 (3)	0.0527 (4)	0.0376 (4)	0.0076 (3)	0.0108 (3)	0.0118 (3)
S7	0.0300 (3)	0.0521 (4)	0.0365 (3)	0.0072 (3)	0.0114 (3)	0.0102 (3)
S8	0.0403 (4)	0.0524 (4)	0.0373 (4)	0.0070 (3)	0.0149 (3)	0.0117 (3)
S9	0.0341 (4)	0.0571 (5)	0.0409 (4)	0.0063 (3)	0.0161 (3)	0.0082 (3)
S10	0.0524 (5)	0.0580 (5)	0.0453 (4)	−0.0010 (3)	0.0263 (4)	0.0070 (3)
C1	0.0312 (13)	0.0358 (13)	0.0250 (11)	0.0017 (10)	0.0060 (10)	0.0011 (10)
C2	0.0317 (13)	0.0371 (14)	0.0259 (11)	−0.0016 (10)	0.0072 (10)	−0.0007 (10)
C3	0.0309 (13)	0.0436 (15)	0.0351 (13)	−0.0004 (11)	0.0067 (11)	0.0040 (12)
C4	0.0310 (13)	0.0433 (14)	0.0272 (12)	−0.0017 (11)	0.0094 (10)	−0.0028 (11)
C5	0.0334 (13)	0.0395 (14)	0.0255 (12)	−0.0016 (11)	0.0097 (10)	0.0009 (10)
C6	0.0367 (14)	0.0404 (15)	0.0346 (13)	−0.0036 (11)	0.0093 (11)	−0.0030 (11)
C7	0.0343 (14)	0.0400 (15)	0.0369 (13)	−0.0001 (11)	0.0116 (11)	0.0064 (11)
C8	0.0355 (15)	0.0531 (18)	0.0359 (14)	−0.0070 (12)	0.0065 (12)	0.0017 (12)
C9	0.0455 (16)	0.0477 (16)	0.0350 (14)	−0.0146 (13)	0.0120 (12)	−0.0065 (12)
C10	0.0398 (16)	0.0488 (17)	0.0505 (17)	−0.0050 (13)	0.0156 (13)	−0.0090 (14)
C11	0.0291 (14)	0.0540 (18)	0.0481 (16)	−0.0027 (12)	0.0045 (12)	−0.0045 (13)
C12	0.0397 (15)	0.0354 (14)	0.0362 (14)	−0.0080 (11)	0.0080 (11)	0.0014 (11)
C13	0.0484 (17)	0.0397 (15)	0.0416 (15)	−0.0063 (12)	0.0070 (13)	−0.0025 (12)
C14	0.0462 (17)	0.067 (2)	0.0377 (15)	0.0049 (15)	0.0109 (13)	−0.0032 (14)
C15	0.078 (3)	0.076 (2)	0.0428 (17)	−0.004 (2)	0.0214 (17)	0.0046 (17)
C16	0.115 (3)	0.057 (2)	0.0365 (17)	0.000 (2)	0.006 (2)	0.0055 (15)
C17	0.070 (2)	0.059 (2)	0.053 (2)	0.0159 (18)	−0.0184 (18)	−0.0065 (17)
C18	0.0400 (17)	0.0571 (19)	0.0533 (18)	0.0019 (14)	−0.0008 (14)	−0.0100 (15)
Cl1	0.0503 (4)	0.0688 (5)	0.0517 (4)	0.0169 (4)	0.0200 (4)	0.0074 (4)
Cl2	0.0677 (6)	0.0911 (7)	0.0480 (5)	−0.0198 (5)	0.0144 (4)	−0.0287 (4)
N1	0.0406 (13)	0.0401 (13)	0.0336 (11)	−0.0008 (10)	0.0037 (10)	−0.0076 (10)

Geometric parameters (Å, º) top

Ni1—S2	2.1589 (7)	C8—C9	1.381 (4)
Ni1—S6	2.1624 (7)	C8—H8	0.9300
Ni1—S1	2.1633 (7)	C9—C10	1.374 (4)
Ni1—S7	2.1640 (7)	C9—Cl2	1.732 (3)
S1—C1	1.715 (2)	C10—C11	1.374 (4)
S2—C2	1.704 (2)	C10—H10	0.9300
S3—C3	1.726 (3)	C11—C12	1.384 (4)
S3—C2	1.731 (2)	C11—H11	0.9300
S4—C3	1.726 (3)	C12—C13	1.505 (4)
S4—C1	1.736 (2)	C13—N1	1.489 (3)
S5—C3	1.643 (3)	C13—H13A	0.9700
S6—C4	1.718 (3)	C13—H13B	0.9700
S7—C5	1.722 (2)	C14—N1	1.335 (4)
S8—C6	1.734 (3)	C14—C15	1.364 (4)
S8—C5	1.744 (2)	C14—H14	0.9300
S9—C6	1.721 (3)	C15—C16	1.365 (5)
S9—C4	1.743 (2)	C15—H15	0.9300
S10—C6	1.649 (3)	C16—C17	1.365 (6)
C1—C2	1.365 (3)	C16—H16	0.9300
C4—C5	1.352 (4)	C17—C18	1.367 (5)
C7—C8	1.382 (4)	C17—H17	0.9300
C7—C12	1.393 (4)	C18—N1	1.345 (4)
C7—Cl1	1.738 (3)	C18—H18	0.9300

S2—Ni1—S6	178.26 (3)	C7—C8—H8	120.8
S2—Ni1—S1	93.06 (3)	C10—C9—C8	121.7 (3)
S6—Ni1—S1	86.45 (3)	C10—C9—Cl2	118.9 (2)
S2—Ni1—S7	87.10 (3)	C8—C9—Cl2	119.3 (2)
S6—Ni1—S7	93.46 (3)	C9—C10—C11	118.4 (3)
S1—Ni1—S7	177.67 (3)	C9—C10—H10	120.8
C1—S1—Ni1	102.09 (8)	C11—C10—H10	120.8
C2—S2—Ni1	102.27 (9)	C10—C11—C12	122.6 (3)
C3—S3—C2	97.68 (12)	C10—C11—H11	118.7
C3—S4—C1	97.25 (12)	C12—C11—H11	118.7
C4—S6—Ni1	101.67 (9)	C11—C12—C7	117.1 (2)
C5—S7—Ni1	101.78 (9)	C11—C12—C13	119.9 (2)
C6—S8—C5	96.99 (12)	C7—C12—C13	123.0 (3)
C6—S9—C4	97.61 (12)	N1—C13—C12	111.7 (2)
C2—C1—S1	120.93 (19)	N1—C13—H13A	109.3
C2—C1—S4	116.16 (19)	C12—C13—H13A	109.3
S1—C1—S4	122.87 (14)	N1—C13—H13B	109.3
C1—C2—S2	121.51 (19)	C12—C13—H13B	109.3
C1—C2—S3	115.69 (19)	H13A—C13—H13B	107.9
S2—C2—S3	122.71 (15)	N1—C14—C15	120.8 (3)
S5—C3—S3	124.54 (16)	N1—C14—H14	119.6
S5—C3—S4	122.34 (16)	C15—C14—H14	119.6
S3—C3—S4	113.12 (14)	C14—C15—C16	119.4 (3)
C5—C4—S6	121.83 (19)	C14—C15—H15	120.3
C5—C4—S9	115.77 (19)	C16—C15—H15	120.3
S6—C4—S9	122.29 (15)	C15—C16—C17	119.5 (3)
C4—C5—S7	121.21 (19)	C15—C16—H16	120.3
C4—C5—S8	116.37 (19)	C17—C16—H16	120.3
S7—C5—S8	122.40 (15)	C16—C17—C18	119.8 (3)
S10—C6—S9	122.42 (16)	C16—C17—H17	120.1
S10—C6—S8	124.40 (16)	C18—C17—H17	120.1
S9—C6—S8	113.18 (15)	N1—C18—C17	120.0 (3)
C8—C7—C12	121.9 (3)	N1—C18—H18	120.0
C8—C7—Cl1	117.4 (2)	C17—C18—H18	120.0
C12—C7—Cl1	120.7 (2)	C14—N1—C18	120.5 (3)
C9—C8—C7	118.3 (3)	C14—N1—C13	120.2 (2)
C9—C8—H8	120.8	C18—N1—C13	119.3 (3)

C12—C7—C8—C9	−0.5 (4)	C11—C12—C13—N1	77.2 (3)
Cl1—C7—C8—C9	178.5 (2)	C7—C12—C13—N1	−104.5 (3)
C7—C8—C9—C10	−0.6 (4)	N1—C14—C15—C16	0.4 (5)
C7—C8—C9—Cl2	179.2 (2)	C14—C15—C16—C17	−1.0 (5)
C8—C9—C10—C11	0.8 (4)	C15—C16—C17—C18	0.6 (5)
Cl2—C9—C10—C11	−179.0 (2)	C16—C17—C18—N1	0.5 (5)
C9—C10—C11—C12	0.2 (4)	C15—C14—N1—C18	0.7 (4)
C10—C11—C12—C7	−1.3 (4)	C15—C14—N1—C13	−179.4 (3)
C10—C11—C12—C13	177.2 (3)	C17—C18—N1—C14	−1.1 (4)
C8—C7—C12—C11	1.5 (4)	C17—C18—N1—C13	179.0 (3)
Cl1—C7—C12—C11	−177.6 (2)	C12—C13—N1—C14	86.7 (3)
C8—C7—C12—C13	−176.9 (3)	C12—C13—N1—C18	−93.4 (3)
Cl1—C7—C12—C13	4.0 (4)

Experimental details

Crystal data
Chemical formula	(C₁₂H₁₀Cl₂N)[Ni(C₃S₅)₂]
M_r	690.48
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	14.4614 (5), 8.2158 (3), 21.8894 (8)
β (°)	107.231 (1)
V (Å³)	2484.00 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.85
Crystal size (mm)	0.26 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.645, 0.837
No. of measured, independent and observed [I > 2σ(I)] reflections	18903, 4615, 3992
R_int	0.085
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.092, 1.04
No. of reflections	4615
No. of parameters	290
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.59, −0.69

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

Acknowledgements

This work was supported by the National Natural Science Foundation of China (No. 20971004), the Key Project of the Chinese Ministry of Education (No. 210102) and the Natural Science Foundation of Anhui Province (No. 11040606M45).

References

Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cassoux, P. (1999). Coord. Chem. Rev. 185–186, 213–232. Web of Science CrossRef CAS Google Scholar
Cassoux, P., Valade, L., Kobayashi, H., Kobayashi, A., Clark, R. A. & Underhill, A. (1991). Coord. Chem. Rev. 110, 115–160. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, C.-S., Batsanov, A. S., Bryce, M. R. & Howard, J. A. K. (1998). Synthesis, pp. 1615–1618. CSD CrossRef Google Scholar

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