Crystal structure of bis­(1-hexyl-N,N-di­methyl­pyridinium) bis­(maleo­nitrile­dithiol­ato)nickelate(II)

Yu, S.-S.; Zhang, H.

doi:10.1107/S2056989016011191

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ISSN: 2056-9890

Volume 72| Part 8| August 2016| Pages 1197-1200

https://doi.org/10.1107/S2056989016011191

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Crystal structure of bis(1-hexyl-N,N-dimethylpyridinium) bis(maleonitriledithiolato)nickelate(II)

Shan-Shan Yu ^a,^b ^* and Hui Zhang ^a,^b

^aDepartment of Environmental Science, Nanjing Xiaozhuang College, Nanjing 211171, People's Republic of China, and ^bHuabao Food Flavor & Fragrance (Shanghai) Co., Ltd, Shanghai, 201821, People's Republic of China
^*Correspondence e-mail: yushanshan_2005@163.com

Edited by G. Smith, Queensland University of Technology, Australia (Received 6 June 2016; accepted 9 July 2016; online 26 July 2016)

The asymmetric unit of the title compound, (C₁₃H₂₃N₂)₂[Ni(C₄N₂S₂)₂], consists of a 1-hexyl-N,N-dimethylpyridinium cation and one half of a [Ni(mnt)₂]²⁻ dianion (mnt²⁻ = maleonitriledithiolate) in which the Ni²⁺ cation lies on a crystallographic inversion centre. The square-planar coordination about Ni²⁺ comprises four S atoms from two bidentate chelate mnt²⁻ ligands [Ni—S = 2.1791 (9) and 2.1810 (8) Å, and S—Ni—S bite angle = 91.93 (3)°]. The hydrocarbon chains of cations show trans-planar conformations and lie approximately parallel to the long molecular axis of the [Ni(mnt)₂]²⁻ anions, giving stacks along the c axis. The anions and cations form layers lying parallel to the bc plane. Only weak C—H⋯Ni and C—H⋯π associations are present in the crystal packing.

Keywords: crystal structure; maleonitriledithiolate; hydrocarbon chain; synthesis.

CCDC reference: 1491765

1. Chemical context

Molecular solids based on transition metal dithiolene complexes have attracted much interest in recent years, not only regarding fundamental research of magnetic interactions and magneto-structural correlations but also in 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 because of their application as building blocks in molecular-based materials showing magnetic, superconducting and optical properties (Nishijo et al., 2000 ; Ni et al., 2004 , Ren et al., 2004 ). In our previous studies, we have investigated the effect of the introduction of mobile organic cations into the rigid [Ni(mnt)₂]²⁻ spin system and created some multi-functional compounds (Yu et al., 2012 , 2013 ; Duan et al., 2011 ). In order to further explore the correlation between the structural features of the counter-cations and the stacking patterns of the anions as well as their physical properties, we have designed and synthesized the soft 1-hexyl-N,N-dimethylpyridinium cation and combined it with the [Ni(mnt)₂]²⁻ dianion, giving the title compound, (C₁₃H₂₃N₂)₂[Ni(C₄N₂S₂)₂], (I), and the crystal structure is reported herein.

2. Structural comment

In the structure of (I) (Fig. 1), the asymmetric unit comprises a 1-hexyl-N,N-dimethylpyridinium cation and one half of an [Ni(mnt)₂]²⁻ dianion (mnt²⁻ = maleonitriledithiolate). The Ni²⁺ ion lies on a crystallographic inversion centre (Fig. 1). The complex dianion possesses an approximately planar geometry with Ni—S bond lengths of the bidentate ligands of 2.1791 (9) and 2.1810 (8) Å and an1 S—Ni—S2 bite angle of 91.93 (3)°. These values are in good agreement with those found in various [Ni(mnt)₂]²⁻ compounds (Duan et al., 2014a ).

Figure 1
The atom-numbering scheme in the molecular structure of (I)

, showing the cation and the centrosymmetric dianion, with displacement ellipsoids drawn at the 30% probability level. [Symmetry code: (i) −x + 1, −y, −z.]

The hydrocarbon chain of the cation is slightly disrupted close to the pyridyl ring in the completely trans-planar conformation, with a chain to pyridyl ring dihedral angle of 83.03 (19)°. The direction of the hydrocarbon chains is approximately parallel to the long molecular axis of the anions, with a dihedral angle between the molecular plane of the hydrocarbon chain and that of the anion (defined by S1,S2,S2ⁱ,S1ⁱ) of 10.76 (18)° [symmetry code: (i) −x + 1, −y, −z]. Between the cation and anion there is a novel Ni1⋯H—C17ⁱⁱ interaction (H⋯Ni = 2.72 Å) (Fig. 2) [symmetry code: (ii) −x + 1, −y + 1, −z].

Figure 2
The Ni⋯H—C contact between the layered cation and anion species in (I)

. [Symmetry code: (ii) −x + 1, −y + 1, −z.]

3. Supramolecular features

In the crystal of (I), both the anions and cations form layers lying parallel to the bc plane (Figs. 2 and 3). In the anion layer, two neighboring [Ni(mnt)₂]²⁻ anions are associated via side-to-side stacking with typical interatomic separations of 8.713 (1) Å (Ni1⋯Ni1ⁱⁱ), and 6.218 (3) Å (S1⋯S2ⁱⁱ). The cations are arranged into bilayers, also lying parallel to the ab plane. In each layer, the cations exhibit an antiparallel arrangement. The cation and anion layers stack alternately, forming columns which extend along c (Fig. 4).

Figure 3
Alternating anion and cation layers, which lie parallel to the crystallographic ab plane.

Figure 4
The packing diagram, viewed along b, of the crystals of (I)

In the crystal there are no formal hydrogen-bonding interactions. However, there are two weak C17—H⋯π associations to the chelate ring of the [Ni(mnt)₂]²⁻ dianions (Cg1, defined by Ni1,S1,C2,C3,S2): to Cg1ⁱⁱ and Cg1ⁱⁱⁱ (H⋯Cg = 2.77 Å) [symmetry code: (iii) x, y − 1, z].

4. Database survey

In the structures of [Ni(mnt)₂]²⁻ complex dianions, chair-shaped organic compounds have been chosen as counter-cations and a series of compounds with segregated anion and cation stacks have been obtained (Pei et al., 2012 ; Tian et al., 2009 ; Ren et al., 2006 ). In addition, with [Ni(mnt)₂]²⁻ anions, nine compounds with 1-alkyl-4-aminopyridinium analogs as counter-cations have been synthesized (Duan et al., 2014b ). In these, the hydrocarbon chains of the counter-ions adopt trans-planar conformations and mixed stacking structures of anions and cations are also observed

5. Synthesis and crystallization

Disodium maleonitriledithiolate (2.0 mmol) and nickel(II) chloride hexahydrate (1.0 mmol) were mixed with stirring in water (20 mL) at room temperature. Subsequently, a solution of 1-hexyl-N,N-dimethylpyridinium iodide (1.0 mmol) in methanol (10 mL) was added to the mixture and the red precipitate that was immediately formed was filtered off and washed with methanol. The crude product was recrystallized in acetone (20 mL) to give red block-shaped crystals which were used in the X-ray analysis.

6. Refinement

Crystal data, data collection and refinement details are summarized in Table 1. The H atoms were placed in geometrically idealized positions (C—H = 0.93–0.98 Å) and refined as riding with U_iso(H) = 1.2U_eq(aromatic or methylene) or 1.5U_eq(methyl).

Table 1
Experimental details

Crystal data
Chemical formula	(C₁₃H₂₃N₂)₂[Ni(C₄N₂S₂)₂]
M_r	753.72
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	14.241 (2), 8.7129 (14), 16.393 (3)
β (°)	102.560 (2)
V (Å³)	1985.4 (6)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.73
Crystal size (mm)	0.40 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2000 )
T_min, T_max	0.811, 0.903
No. of measured, independent and observed [I > 2σ(I)] reflections	16992, 4553, 2772
R_int	0.065
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.142, 1.00
No. of reflections	4553
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.47
Computer programs: SMART and SAINT (Bruker, 2000), SHELXS97, SHELXL97 and SHELXTL (Sheldrick, 2008 ).

Supporting information

CCDC reference: 1491765

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989016011191/zs2364sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989016011191/zs2364Isup2.hkl

checkCIF report

Computing details top

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

(I) top

Crystal data top

(C₁₃H₂₃N₂)₂[Ni(C₄N₂S₂)₂]	F(000) = 796
M_r = 753.72	D_x = 1.261 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 773 reflections
a = 14.241 (2) Å	θ = 2.6–21.2°
b = 8.7129 (14) Å	µ = 0.73 mm⁻¹
c = 16.393 (3) Å	T = 296 K
β = 102.560 (2)°	Prism, red
V = 1985.4 (6) Å³	0.40 × 0.20 × 0.20 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	4553 independent reflections
Radiation source: fine-focus sealed tube	2772 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.065
phi and ω scans	θ_max = 27.5°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −18→17
T_min = 0.811, T_max = 0.903	k = −11→11
16992 measured reflections	l = −21→20

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0734P)²] where P = (F_o² + 2F_c²)/3
4553 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.0000	0.05898 (18)
S1	0.54081 (6)	0.24019 (9)	0.02097 (5)	0.0763 (2)
S2	0.64932 (5)	−0.07007 (9)	0.01137 (5)	0.0720 (2)
N1	0.7570 (3)	0.4849 (4)	0.0913 (2)	0.1208 (12)
N2	0.8973 (2)	0.0748 (5)	0.0871 (2)	0.1362 (13)
N3	0.55955 (17)	0.9719 (2)	0.27888 (15)	0.0658 (6)
N4	0.83752 (17)	0.8050 (3)	0.34593 (14)	0.0743 (6)
C1	0.7170 (3)	0.3720 (4)	0.07145 (18)	0.0856 (9)
C2	0.6657 (2)	0.2325 (3)	0.04658 (16)	0.0705 (7)
C3	0.7121 (2)	0.0976 (4)	0.04262 (16)	0.0689 (7)
C4	0.8156 (3)	0.0868 (4)	0.0665 (2)	0.0921 (10)
C5	0.0487 (3)	0.6987 (5)	0.1394 (3)	0.1196 (13)
H5A	0.0644	0.6439	0.0933	0.179*
H5B	−0.0169	0.7329	0.1244	0.179*
H5C	0.0568	0.6322	0.1871	0.179*
C6	0.1144 (2)	0.8359 (4)	0.1604 (2)	0.0938 (10)
H6A	0.1027	0.9054	0.1130	0.113*
H6B	0.0982	0.8898	0.2072	0.113*
C7	0.2197 (2)	0.7958 (4)	0.1820 (2)	0.0845 (9)
H7A	0.2355	0.7409	0.1353	0.101*
H7B	0.2312	0.7268	0.2296	0.101*
C8	0.2867 (2)	0.9327 (3)	0.20257 (19)	0.0748 (8)
H8A	0.2693	0.9910	0.2475	0.090*
H8B	0.2785	0.9990	0.1540	0.090*
C9	0.39199 (19)	0.8855 (3)	0.22865 (18)	0.0716 (7)
H9A	0.3997	0.8152	0.2756	0.086*
H9B	0.4103	0.8316	0.1827	0.086*
C10	0.4579 (2)	1.0208 (3)	0.2530 (2)	0.0779 (8)
H10A	0.4510	1.0907	0.2060	0.093*
H10B	0.4395	1.0754	0.2987	0.093*
C11	0.6025 (2)	0.9523 (3)	0.36010 (17)	0.0683 (7)
H11	0.5689	0.9780	0.4008	0.082*
C12	0.6928 (2)	0.8963 (3)	0.38405 (16)	0.0677 (7)
H12	0.7193	0.8825	0.4406	0.081*
C13	0.7480 (2)	0.8581 (3)	0.32450 (16)	0.0626 (7)
C14	0.8852 (2)	0.7825 (5)	0.4335 (2)	0.1024 (11)
H14A	0.8845	0.8770	0.4635	0.154*
H14B	0.9505	0.7509	0.4370	0.154*
H14C	0.8519	0.7048	0.4577	0.154*
C15	0.8934 (2)	0.7713 (4)	0.2824 (2)	0.0950 (10)
H15A	0.8617	0.6922	0.2457	0.143*
H15B	0.9567	0.7374	0.3094	0.143*
H15C	0.8983	0.8624	0.2506	0.143*
C16	0.7002 (2)	0.8802 (3)	0.23995 (16)	0.0669 (7)
H16	0.7318	0.8563	0.1975	0.080*
C17	0.6098 (2)	0.9351 (3)	0.22026 (17)	0.0706 (7)
H17	0.5806	0.9484	0.1642	0.085*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0627 (3)	0.0692 (3)	0.0450 (3)	0.0056 (2)	0.0115 (2)	−0.00043 (19)
S1	0.0775 (5)	0.0704 (4)	0.0804 (5)	0.0057 (4)	0.0161 (4)	−0.0003 (4)
S2	0.0666 (5)	0.0811 (5)	0.0697 (4)	0.0073 (4)	0.0176 (3)	−0.0089 (4)
N1	0.154 (3)	0.104 (2)	0.096 (2)	−0.047 (2)	0.011 (2)	−0.0003 (17)
N2	0.068 (2)	0.163 (3)	0.170 (4)	0.001 (2)	0.008 (2)	−0.009 (3)
N3	0.0689 (15)	0.0638 (13)	0.0647 (14)	0.0041 (11)	0.0145 (11)	0.0064 (10)
N4	0.0661 (15)	0.0834 (16)	0.0719 (15)	−0.0009 (12)	0.0114 (12)	0.0088 (12)
C1	0.100 (2)	0.095 (2)	0.0589 (17)	−0.018 (2)	0.0110 (16)	0.0051 (16)
C2	0.0776 (19)	0.0844 (19)	0.0497 (15)	−0.0099 (16)	0.0145 (13)	0.0027 (13)
C3	0.0636 (17)	0.094 (2)	0.0504 (15)	−0.0048 (15)	0.0156 (13)	0.0020 (13)
C4	0.075 (2)	0.107 (3)	0.093 (2)	−0.006 (2)	0.0149 (18)	−0.0019 (19)
C5	0.092 (3)	0.121 (3)	0.138 (3)	−0.001 (2)	0.008 (2)	−0.024 (3)
C6	0.080 (2)	0.093 (2)	0.105 (2)	0.0158 (18)	0.0139 (19)	−0.0008 (19)
C7	0.078 (2)	0.083 (2)	0.090 (2)	0.0143 (17)	0.0131 (16)	−0.0048 (17)
C8	0.0730 (19)	0.0747 (17)	0.0780 (19)	0.0143 (15)	0.0193 (15)	0.0096 (15)
C9	0.0698 (18)	0.0703 (17)	0.0746 (18)	0.0099 (14)	0.0154 (14)	0.0063 (14)
C10	0.073 (2)	0.0718 (18)	0.088 (2)	0.0142 (15)	0.0168 (17)	0.0060 (15)
C11	0.081 (2)	0.0683 (16)	0.0592 (17)	−0.0066 (14)	0.0231 (15)	−0.0001 (13)
C12	0.080 (2)	0.0693 (16)	0.0517 (15)	−0.0069 (14)	0.0110 (13)	0.0076 (12)
C13	0.0690 (18)	0.0560 (14)	0.0618 (16)	−0.0084 (13)	0.0117 (13)	0.0048 (12)
C14	0.083 (2)	0.122 (3)	0.090 (2)	0.008 (2)	−0.0071 (18)	0.019 (2)
C15	0.074 (2)	0.100 (2)	0.113 (3)	0.0033 (18)	0.0271 (19)	0.007 (2)
C16	0.0720 (18)	0.0781 (17)	0.0531 (15)	0.0012 (14)	0.0196 (13)	0.0047 (12)
C17	0.078 (2)	0.0781 (17)	0.0551 (15)	0.0001 (15)	0.0140 (14)	0.0096 (13)

Geometric parameters (Å, º) top

Ni1—S1	2.1791 (9)	C16—C17	1.345 (4)
Ni1—S2	2.1810 (8)	C5—H5A	0.9600
Ni1—S1ⁱ	2.1791 (9)	C5—H5B	0.9600
Ni1—S2ⁱ	2.1810 (8)	C5—H5C	0.9600
S1—C2	1.738 (3)	C6—H6A	0.9700
S2—C3	1.731 (3)	C6—H6B	0.9700
N1—C1	1.148 (5)	C7—H7A	0.9700
N2—C4	1.144 (5)	C7—H7B	0.9700
N3—C10	1.480 (4)	C8—H8A	0.9700
N3—C11	1.350 (4)	C8—H8B	0.9700
N3—C17	1.356 (4)	C9—H9A	0.9700
N4—C14	1.462 (4)	C9—H9B	0.9700
N4—C15	1.471 (4)	C10—H10A	0.9700
N4—C13	1.330 (4)	C10—H10B	0.9700
C1—C2	1.431 (5)	C11—H11	0.9300
C2—C3	1.357 (4)	C12—H12	0.9300
C3—C4	1.444 (5)	C14—H14A	0.9600
C5—C6	1.511 (6)	C14—H14B	0.9600
C6—C7	1.505 (4)	C14—H14C	0.9600
C7—C8	1.519 (4)	C15—H15A	0.9600
C8—C9	1.524 (4)	C15—H15B	0.9600
C9—C10	1.506 (4)	C15—H15C	0.9600
C11—C12	1.351 (4)	C16—H16	0.9300
C12—C13	1.420 (4)	C17—H17	0.9300
C13—C16	1.418 (4)

Ni1—S1—C2	103.00 (9)	C7—C6—H6B	109.00
Ni1—S2—C3	102.72 (11)	H6A—C6—H6B	108.00
S1—Ni1—S2	91.93 (3)	C6—C7—H7A	109.00
S1—Ni1—S1ⁱ	180.00	C6—C7—H7B	109.00
S1—Ni1—S2ⁱ	88.07 (3)	C8—C7—H7A	109.00
S1ⁱ—Ni1—S2	88.07 (3)	C8—C7—H7B	109.00
S2—Ni1—S2ⁱ	180.00	H7A—C7—H7B	108.00
S1ⁱ—Ni1—S2ⁱ	91.93 (3)	C7—C8—H8A	109.00
C11—N3—C17	118.3 (2)	C7—C8—H8B	109.00
C10—N3—C11	121.6 (2)	C9—C8—H8A	109.00
C10—N3—C17	120.0 (2)	C9—C8—H8B	109.00
C14—N4—C15	117.5 (2)	H8A—C8—H8B	108.00
C13—N4—C14	121.3 (2)	C8—C9—H9A	109.00
C13—N4—C15	121.2 (2)	C8—C9—H9B	109.00
N1—C1—C2	179.1 (4)	C10—C9—H9A	109.00
C1—C2—C3	121.7 (3)	C10—C9—H9B	109.00
S1—C2—C1	117.9 (2)	H9A—C9—H9B	108.00
S1—C2—C3	120.4 (2)	N3—C10—H10A	109.00
C2—C3—C4	121.5 (3)	N3—C10—H10B	109.00
S2—C3—C2	121.3 (2)	C9—C10—H10A	109.00
S2—C3—C4	117.2 (3)	C9—C10—H10B	109.00
N2—C4—C3	177.9 (4)	H10A—C10—H10B	108.00
C5—C6—C7	114.0 (3)	N3—C11—H11	119.00
C6—C7—C8	114.6 (3)	C12—C11—H11	119.00
C7—C8—C9	112.5 (2)	C11—C12—H12	119.00
C8—C9—C10	112.4 (2)	C13—C12—H12	119.00
N3—C10—C9	111.4 (2)	N4—C14—H14A	109.00
N3—C11—C12	122.1 (3)	N4—C14—H14B	110.00
C11—C12—C13	121.3 (2)	N4—C14—H14C	110.00
N4—C13—C12	122.8 (2)	H14A—C14—H14B	109.00
N4—C13—C16	122.3 (2)	H14A—C14—H14C	109.00
C12—C13—C16	114.9 (3)	H14B—C14—H14C	109.00
C13—C16—C17	120.9 (3)	N4—C15—H15A	109.00
N3—C17—C16	122.6 (3)	N4—C15—H15B	109.00
C6—C5—H5A	110.00	N4—C15—H15C	109.00
C6—C5—H5B	109.00	H15A—C15—H15B	110.00
C6—C5—H5C	109.00	H15A—C15—H15C	109.00
H5A—C5—H5B	109.00	H15B—C15—H15C	109.00
H5A—C5—H5C	109.00	C13—C16—H16	120.00
H5B—C5—H5C	110.00	C17—C16—H16	120.00
C5—C6—H6A	109.00	N3—C17—H17	119.00
C5—C6—H6B	109.00	C16—C17—H17	119.00
C7—C6—H6A	109.00

S2—Ni1—S1—C2	−6.92 (10)	C14—N4—C13—C16	−179.7 (3)
S2ⁱ—Ni1—S1—C2	173.09 (10)	C15—N4—C13—C12	−178.1 (3)
S1—Ni1—S2—C3	7.10 (10)	S1—C2—C3—S2	0.5 (3)
S1ⁱ—Ni1—S2—C3	−172.90 (10)	S1—C2—C3—C4	−177.7 (2)
Ni1—S1—C2—C1	−174.9 (2)	C1—C2—C3—S2	−179.3 (2)
Ni1—S1—C2—C3	5.3 (2)	C1—C2—C3—C4	2.5 (4)
Ni1—S2—C3—C2	−6.1 (2)	C5—C6—C7—C8	179.5 (3)
Ni1—S2—C3—C4	172.2 (2)	C6—C7—C8—C9	176.8 (3)
C17—N3—C11—C12	−0.6 (4)	C7—C8—C9—C10	−177.2 (3)
C10—N3—C17—C16	−175.5 (2)	C8—C9—C10—N3	179.4 (2)
C11—N3—C17—C16	0.0 (4)	N3—C11—C12—C13	1.3 (4)
C10—N3—C11—C12	174.8 (2)	C11—C12—C13—N4	178.9 (3)
C11—N3—C10—C9	−96.8 (3)	C11—C12—C13—C16	−1.3 (4)
C17—N3—C10—C9	78.5 (3)	N4—C13—C16—C17	−179.6 (3)
C14—N4—C13—C12	0.0 (4)	C12—C13—C16—C17	0.7 (4)
C15—N4—C13—C16	2.2 (4)	C13—C16—C17—N3	−0.1 (4)

Symmetry code: (i) −x+1, −y, −z.

Acknowledgements

The authors thank the Natural Science Foundation of China for financial support (grant No. 21301093).

References

Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Duan, H. B., Ren, X. M. & Liu, J. L. (2014a). Soft Mater. 12, 166–178. CrossRef CAS Google Scholar
Duan, H. B., Ren, X. M., Shen, L. J., Jin, W. Q., Meng, Q. J., Tian, Z. F. & Zhou, S. M. (2011). Dalton Trans. 40, 3622–3630. Web of Science CSD CrossRef CAS PubMed Google Scholar
Duan, H. B., Zhang, X. M. & Zhou, H. (2014b). Synth. Met. 195, 294–298. CSD CrossRef CAS Google Scholar
Ni, C. L., Dang, D. B., Song, Y., Gao, S., Li, Y., Ni, Z., Tian, Z., Wen, L. & Meng, Q. (2004). Chem. Phys. Lett. 396, 353–358. CSD CrossRef CAS Google Scholar
Nishijo, J., Ogura, E., Yamaura, J., Miyazaki, A., Enoki, T., Takano, T., Kuwatani, Y. & Iyoda, M. (2000). Solid State Commun. 116, 661–664. Web of Science CSD CrossRef CAS Google Scholar
Pei, W. B., Wu, J. S., Ren, X. M., Tian, Z. F. & Xie, J. L. (2012). Dalton Trans. 41, 2667–2676. CSD CrossRef CAS PubMed Google Scholar
Ren, X. M., Nishihara, S., Akutagawa, T., Noro, S., Nakamura, T., Fujita, W. & Awaga, K. (2006). Chem. Phys. Lett. 418, 423–427. CSD CrossRef CAS Google Scholar
Ren, X. M., Okudera, H., Kremer, R. K., Song, Y., He, C., Meng, Q. J. & Wu, P. H. (2004). Inorg. Chem. 43, 2569–2576. Web of Science CSD CrossRef PubMed CAS 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
Tian, Z. F., Duan, H. B., Ren, X. M., Lu, C. S., Li, Y. Z., Song, Y., Zhu, H. & Meng, Q. J. (2009). J. Phys. Chem. B, 113, 8278–8283. CSD CrossRef PubMed CAS Google Scholar
Yu, S. S., Duan, H. B., Chen, X. R., Tian, Z. F. & Ren, X. M. (2013). Dalton Trans. 42, 3827–3834. CSD CrossRef CAS PubMed Google Scholar
Yu, S. S., Duan, H. B., Pei, W. B., Chen, X. R., Ren, X. M. & Tian, Z. F. (2012). Inorg. Chem. Commun. 20, 307–311. CSD CrossRef CAS Google Scholar

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