Hexakis(1H-imidazole-κN3)nickel(II) bis­(3-thienylacetate)

Song, W.-D.; Ji, L.-L.; Wang, H.

doi:10.1107/S1600536808006363

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 4| April 2008| Page m550

doi:10.1107/S1600536808006363

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Hexakis(1H-imidazole-κN³)nickel(II) bis(3-thienylacetate)

Wen-Dong Song,^a ^* Li-Li Ji ^a and Hao Wang ^a

^aCollege of Science, Guang Dong Ocean University, Zhanjiang 524088, People's Republic of China
^*Correspondence e-mail: songwd60@126.com

(Received 14 December 2007; accepted 7 March 2008; online 14 March 2008)

In the title complex, [Ni(C₃H₄N₂)₆](C₆H₅O₂S)₂, the Ni^II atom displays an octahedral coordination geometry, defined by six N atoms from the imidazole ligands. Intermolecular N—H⋯O hydrogen-bonding interactions between the cationic complex and 3-thienylacetate anions form a three-dimensional network architecture. The two 3-thienylacetate anions are disordered, with occupancy ratios of circa 0.774 (1):0.226 (1) and ca 0.753 (5):0.247 (5).

Related literature

For related literature, see: Ng et al. (2001 ).

Experimental

Crystal data

[Ni(C₃H₄N₂)₆](C₆H₅O₂S)₂
M_r = 749.52
Triclinic, $[P \overline 1]$
a = 9.2483 (3) Å
b = 9.8529 (3) Å
c = 19.6365 (6) Å
α = 84.696 (1)°
β = 88.380 (2)°
γ = 80.157 (2)°
V = 1755.30 (9) Å³
Z = 2
Mo Kα radiation
μ = 0.72 mm⁻¹
T = 296 (2) K
0.20 × 0.16 × 0.11 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.869, T_max = 0.924
13333 measured reflections
7140 independent reflections
5337 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.111
S = 1.06
7140 reflections
480 parameters
38 restraints
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N12—H12⋯O4ⁱ	0.86	2.56	3.124 (3)	124
N12—H12⋯O3ⁱ	0.86	1.97	2.826 (3)	170
N10—H10A⋯O3ⁱⁱ	0.86	1.88	2.718 (3)	164
N8—H8A⋯O2ⁱⁱⁱ	0.86	1.81	2.660 (3)	170
N4—H4A⋯O4^iv	0.86	1.89	2.688 (3)	153
N2—H2⋯O1^v	0.86	1.91	2.749 (3)	166
N6—H6⋯O1ⁱⁱ	0.86	1.90	2.711 (3)	156
Symmetry codes: (i) -x+1, -y+2, -z+2; (ii) x+1, y, z; (iii) -x+2, -y+2, -z+1; (iv) -x+1, -y+1, -z+2; (v) -x+1, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); 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: 10.1107/S1600536808006363/sg2218sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808006363/sg2218Isup2.hkl

checkCIF report

Comment top

In the structural investigation of 3-thienylacetate complexes, it has been found that the 3-thienylacetate functions as a multidentate ligand [Ng et al. (2001)], with versatile binding and coordination modes. In this study, we expected to obtain a complex composed of nickel(II), 3-thienylacetate and imidazole by hydrothermal reaction. Unfortunately, the Ni^II atom was not coordinated by 3-thienylacetate. We finally obtained the title structure, (I), composed of cations and anions.

As shown in Fig. 1, the crystal structure of the title complex consists of [Ni(C₃H₄N₂)₆]²⁺ and two different 3-thienylacetate anions. The Ni^II atom is coordinated by six different imidazole molecules in a slightly distorted octahedral geometry. The cationic complexes link the 3-thienylacetate anions by intermolecular N—H···O hydrogen bonding interactions (table 1) to form a three-dimensional network structure (Fig. 2).

Related literature top

For related literature, see: Ng et al. (2001).

Experimental top

A mixture of nickel chloride (1 mmol), 3-thienylacetic acid (1 mmol), imidazole (1 mmol), NaOH (1.5 mmol) and H₂O (12 ml) was placed in a 23 ml Teflon reactor, which was heated to 433 K for three days and then cooled to room temperature at a rate of 10 K h^-1. The crystals obtained were washed with water and dryed in air.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 structure of (I), showing the atomic numbering scheme. Non-H atoms are shown with 30% probability displacement ellipsoids.
	Fig. 2. A packing view of the title compound. The intermolecluar hydrogen bonds are shown as dashed lines.

Hexakis(1H-imidazole-κN³)nickel(II) bis(3-thienylacetate) top

Crystal data top

[Ni(C₃H₄N₂)₆](C₆H₅O₂S)₂	Z = 2
M_r = 749.52	F(000) = 780
Triclinic, P1	D_x = 1.418 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2483 (3) Å	Cell parameters from 5680 reflections
b = 9.8529 (3) Å	θ = 1.4–28.0°
c = 19.6365 (6) Å	µ = 0.73 mm⁻¹
α = 84.696 (1)°	T = 296 K
β = 88.380 (2)°	Block, blue
γ = 80.157 (2)°	0.20 × 0.16 × 0.11 mm
V = 1755.30 (9) Å³

Data collection top

Bruker APEXII area-detector diffractometer	7140 independent reflections
Radiation source: fine-focus sealed tube	5337 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 26.5°, θ_min = 1.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −11→11
T_min = 0.869, T_max = 0.925	k = −5→12
13333 measured reflections	l = −24→24

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0423P)² + 0.8694P] where P = (F_o² + 2F_c²)/3
7140 reflections	(Δ/σ)_max = 0.001
480 parameters	Δρ_max = 0.39 e Å⁻³
38 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

[Ni(C₃H₄N₂)₆](C₆H₅O₂S)₂	γ = 80.157 (2)°
M_r = 749.52	V = 1755.30 (9) Å³
Triclinic, P1	Z = 2
a = 9.2483 (3) Å	Mo Kα radiation
b = 9.8529 (3) Å	µ = 0.73 mm⁻¹
c = 19.6365 (6) Å	T = 296 K
α = 84.696 (1)°	0.20 × 0.16 × 0.11 mm
β = 88.380 (2)°

Data collection top

Bruker APEXII area-detector diffractometer	7140 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	5337 reflections with I > 2σ(I)
T_min = 0.869, T_max = 0.925	R_int = 0.025
13333 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	38 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 1.06	Δρ_max = 0.39 e Å⁻³
7140 reflections	Δρ_min = −0.27 e Å⁻³
480 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	Occ. (<1)
C1	0.4131 (4)	0.4287 (3)	0.66425 (18)	0.0627 (9)
H1	0.3888	0.3694	0.6339	0.075*
C2	0.5286 (3)	0.4973 (3)	0.65584 (14)	0.0484 (7)
C3	0.5372 (4)	0.5773 (4)	0.71015 (18)	0.0681 (9)
H3	0.6112	0.6302	0.7111	0.082*
C5	0.6323 (4)	0.4848 (4)	0.59608 (18)	0.0710 (10)
H5A	0.6163	0.4062	0.5727	0.085*
H5B	0.7315	0.4641	0.6135	0.085*
C6	0.6230 (3)	0.6089 (3)	0.54369 (13)	0.0474 (7)
C8	0.3563 (4)	0.2371 (3)	0.99004 (16)	0.0598 (8)
H8	0.4549	0.2448	0.9920	0.072*
C9	0.2493 (3)	0.3502 (3)	0.96818 (14)	0.0500 (7)
C10	0.1119 (4)	0.3137 (4)	0.97049 (19)	0.0683 (9)
H10	0.0270	0.3748	0.9576	0.082*
C11	0.2791 (4)	0.4927 (3)	0.94645 (14)	0.0559 (8)
H11A	0.1976	0.5421	0.9192	0.067*
H11B	0.3661	0.4849	0.9174	0.067*
C12	0.3015 (3)	0.5780 (3)	1.00487 (13)	0.0427 (6)
C13	0.7099 (3)	1.1011 (3)	0.59500 (13)	0.0444 (6)
H13	0.7758	1.1596	0.5804	0.053*
C14	0.5169 (4)	1.0069 (4)	0.60100 (17)	0.0663 (9)
H14	0.4254	0.9851	0.5928	0.080*
C15	0.6119 (3)	0.9449 (3)	0.64942 (17)	0.0637 (9)
H15	0.5958	0.8722	0.6808	0.076*
C16	0.9193 (3)	0.6510 (3)	0.75680 (15)	0.0517 (7)
H16	0.9882	0.6223	0.7234	0.062*
C17	0.8696 (4)	0.5679 (3)	0.80681 (16)	0.0601 (8)
H17	0.8984	0.4727	0.8145	0.072*
C18	0.7630 (3)	0.7782 (3)	0.81614 (13)	0.0446 (6)
H18	0.7026	0.8539	0.8327	0.053*
C19	1.1837 (3)	0.8033 (3)	0.63842 (14)	0.0460 (7)
H19	1.2480	0.8292	0.6684	0.055*
N6	1.2259 (3)	0.7234 (3)	0.58772 (11)	0.0532 (6)
H6	1.3145	0.6887	0.5772	0.064*
C21	0.9893 (3)	0.7778 (3)	0.58834 (13)	0.0478 (7)
H21	0.8912	0.7835	0.5772	0.057*
C22	0.8396 (3)	1.1189 (3)	0.84289 (14)	0.0485 (7)
H22	0.9326	1.0865	0.8606	0.058*
C23	0.6170 (4)	1.2253 (4)	0.83415 (17)	0.0744 (11)
H23	0.5270	1.2794	0.8429	0.089*
C24	0.6547 (3)	1.1572 (3)	0.77818 (16)	0.0613 (9)
H24	0.5936	1.1560	0.7415	0.074*
C25	1.0829 (3)	1.1481 (3)	0.60810 (14)	0.0462 (6)
H25	1.1209	1.0723	0.5843	0.055*
C26	1.0367 (4)	1.3572 (3)	0.63700 (17)	0.0623 (8)
H26	1.0349	1.4516	0.6382	0.075*
C27	0.9656 (4)	1.2747 (3)	0.68025 (16)	0.0554 (8)
H27	0.9057	1.3040	0.7168	0.066*
C28	1.1230 (3)	0.8441 (3)	0.83343 (13)	0.0452 (6)
H28	1.0629	0.7789	0.8455	0.054*
C29	1.2965 (4)	0.9652 (4)	0.83702 (17)	0.0705 (10)
H29	1.3772	1.0002	0.8507	0.085*
C30	1.2145 (3)	1.0096 (4)	0.78075 (16)	0.0600 (8)
H30	1.2302	1.0813	0.7487	0.072*
N1	0.7348 (2)	1.0039 (2)	0.64586 (10)	0.0367 (5)
N2	0.5794 (3)	1.1062 (2)	0.56680 (11)	0.0480 (6)
H2	0.5425	1.1624	0.5332	0.058*
N3	0.8519 (2)	0.7861 (2)	0.76277 (10)	0.0391 (5)
N4	0.7707 (3)	0.6476 (3)	0.84356 (12)	0.0549 (6)
H4A	0.7214	0.6201	0.8783	0.066*
N5	1.0399 (2)	0.8411 (2)	0.64094 (10)	0.0390 (5)
C20	1.1030 (4)	0.7072 (3)	0.55600 (15)	0.0567 (8)
H20	1.0984	0.6565	0.5187	0.068*
N7	0.9954 (2)	1.1416 (2)	0.66199 (10)	0.0389 (5)
N8	1.1108 (3)	1.2744 (3)	0.59158 (13)	0.0551 (6)
H8A	1.1657	1.2993	0.5583	0.066*
N9	1.1042 (2)	0.9323 (2)	0.77832 (10)	0.0419 (5)
N10	1.2373 (3)	0.8589 (3)	0.86970 (12)	0.0527 (6)
H10A	1.2682	0.8107	0.9068	0.063*
N11	0.7967 (2)	1.0899 (2)	0.78359 (10)	0.0405 (5)
N12	0.7343 (3)	1.2000 (3)	0.87473 (12)	0.0579 (7)
H12	0.7404	1.2305	0.9140	0.069*
Ni1	0.91924 (3)	0.96550 (3)	0.711416 (15)	0.03369 (11)
O1	0.5032 (2)	0.6882 (2)	0.53592 (10)	0.0561 (5)
O2	0.7362 (3)	0.6167 (3)	0.50974 (13)	0.0884 (8)
O3	0.2792 (2)	0.7082 (2)	0.99273 (10)	0.0554 (5)
O4	0.3444 (3)	0.5178 (2)	1.06095 (10)	0.0628 (6)
C4	0.4398 (14)	0.5770 (17)	0.7597 (8)	0.089 (3)	0.774 (12)
H4	0.4352	0.6252	0.7985	0.107*	0.774 (12)
S1	0.3174 (3)	0.4661 (3)	0.73853 (14)	0.0805 (17)	0.774 (12)
C7	0.3090 (15)	0.1157 (12)	1.0081 (8)	0.067 (3)	0.753 (5)
H7	0.3670	0.0318	1.0226	0.080*	0.753 (5)
S2	0.1132 (3)	0.1476 (2)	0.99890 (12)	0.0834 (8)	0.753 (5)
S1'	0.3871 (14)	0.5542 (15)	0.7623 (6)	0.124 (12)	0.226 (12)
C4'	0.324 (3)	0.429 (3)	0.7164 (11)	0.060 (8)	0.226 (12)
H4'	0.2484	0.3778	0.7267	0.072*	0.226 (12)
C7'	0.098 (3)	0.1816 (18)	0.9903 (14)	0.16 (2)	0.247 (5)
H7'	0.0132	0.1426	0.9924	0.193*	0.247 (5)
S2'	0.2812 (15)	0.0985 (12)	1.0115 (8)	0.091 (4)	0.247 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.064 (2)	0.055 (2)	0.069 (2)	−0.0105 (16)	−0.0164 (18)	0.0026 (16)
C2	0.0470 (16)	0.0488 (17)	0.0432 (15)	0.0005 (13)	−0.0061 (12)	0.0146 (13)
C3	0.085 (3)	0.063 (2)	0.059 (2)	−0.0222 (18)	−0.0127 (19)	0.0047 (17)
C5	0.065 (2)	0.065 (2)	0.068 (2)	0.0153 (17)	0.0114 (17)	0.0182 (18)
C6	0.0476 (16)	0.0587 (18)	0.0361 (14)	−0.0126 (14)	0.0016 (12)	0.0004 (13)
C8	0.063 (2)	0.059 (2)	0.0593 (19)	−0.0130 (16)	0.0103 (15)	−0.0139 (16)
C9	0.0613 (19)	0.0543 (18)	0.0395 (15)	−0.0195 (15)	0.0042 (13)	−0.0138 (13)
C10	0.066 (2)	0.071 (2)	0.072 (2)	−0.0202 (19)	−0.0022 (18)	−0.0153 (19)
C11	0.077 (2)	0.0567 (19)	0.0371 (15)	−0.0195 (16)	−0.0023 (14)	−0.0053 (13)
C12	0.0457 (15)	0.0502 (17)	0.0345 (14)	−0.0154 (12)	0.0054 (11)	−0.0035 (12)
C13	0.0444 (15)	0.0462 (16)	0.0408 (15)	−0.0085 (12)	−0.0051 (12)	0.0078 (12)
C14	0.0580 (19)	0.069 (2)	0.074 (2)	−0.0256 (17)	−0.0246 (17)	0.0182 (18)
C15	0.061 (2)	0.062 (2)	0.070 (2)	−0.0281 (16)	−0.0207 (16)	0.0278 (17)
C16	0.0685 (19)	0.0358 (15)	0.0474 (16)	−0.0021 (13)	0.0075 (14)	−0.0018 (13)
C17	0.090 (2)	0.0334 (16)	0.0547 (18)	−0.0088 (15)	0.0014 (17)	0.0036 (14)
C18	0.0506 (16)	0.0429 (16)	0.0381 (14)	−0.0062 (12)	0.0021 (12)	0.0033 (12)
C19	0.0461 (16)	0.0480 (16)	0.0391 (14)	0.0020 (12)	0.0026 (12)	0.0020 (12)
N6	0.0540 (15)	0.0539 (15)	0.0418 (13)	0.0140 (12)	0.0104 (11)	0.0011 (11)
C21	0.0533 (17)	0.0492 (17)	0.0400 (15)	−0.0046 (13)	−0.0008 (13)	−0.0071 (13)
C22	0.0545 (17)	0.0491 (17)	0.0415 (15)	−0.0043 (13)	0.0022 (13)	−0.0113 (13)
C23	0.072 (2)	0.081 (3)	0.057 (2)	0.0263 (19)	0.0033 (18)	−0.0153 (18)
C24	0.0593 (19)	0.069 (2)	0.0482 (17)	0.0155 (16)	−0.0044 (14)	−0.0168 (15)
C25	0.0505 (16)	0.0413 (16)	0.0462 (16)	−0.0102 (12)	0.0024 (13)	0.0024 (12)
C26	0.075 (2)	0.0413 (18)	0.074 (2)	−0.0226 (16)	0.0059 (18)	−0.0003 (16)
C27	0.066 (2)	0.0464 (18)	0.0539 (18)	−0.0133 (15)	0.0080 (15)	−0.0028 (14)
C28	0.0494 (16)	0.0452 (16)	0.0384 (14)	−0.0024 (12)	−0.0073 (12)	0.0010 (12)
C29	0.063 (2)	0.097 (3)	0.056 (2)	−0.032 (2)	−0.0206 (16)	0.0054 (19)
C30	0.0579 (19)	0.075 (2)	0.0492 (17)	−0.0245 (17)	−0.0101 (14)	0.0100 (16)
N1	0.0421 (12)	0.0319 (11)	0.0344 (11)	−0.0026 (9)	−0.0028 (9)	0.0007 (9)
N2	0.0514 (14)	0.0482 (14)	0.0413 (12)	−0.0034 (11)	−0.0130 (11)	0.0067 (11)
N3	0.0439 (12)	0.0386 (12)	0.0331 (11)	−0.0054 (9)	−0.0008 (9)	0.0021 (9)
N4	0.0746 (17)	0.0543 (16)	0.0373 (12)	−0.0229 (13)	0.0035 (12)	0.0090 (11)
N5	0.0402 (12)	0.0418 (13)	0.0332 (11)	−0.0036 (9)	0.0021 (9)	−0.0008 (9)
C20	0.076 (2)	0.0509 (18)	0.0393 (15)	0.0030 (15)	0.0036 (15)	−0.0110 (13)
N7	0.0437 (12)	0.0353 (12)	0.0372 (11)	−0.0081 (9)	−0.0018 (9)	0.0016 (9)
N8	0.0532 (15)	0.0600 (17)	0.0530 (15)	−0.0209 (12)	0.0030 (12)	0.0104 (13)
N9	0.0428 (12)	0.0468 (13)	0.0348 (11)	−0.0055 (10)	−0.0040 (9)	−0.0005 (10)
N10	0.0574 (15)	0.0593 (16)	0.0387 (13)	−0.0028 (12)	−0.0140 (11)	0.0014 (11)
N11	0.0475 (13)	0.0378 (12)	0.0344 (11)	−0.0039 (10)	0.0026 (9)	−0.0011 (9)
N12	0.0740 (18)	0.0554 (16)	0.0435 (14)	−0.0027 (13)	0.0027 (13)	−0.0164 (12)
Ni1	0.03781 (18)	0.03297 (18)	0.02871 (17)	−0.00365 (13)	0.00005 (12)	0.00110 (12)
O1	0.0570 (13)	0.0541 (13)	0.0480 (11)	0.0056 (10)	0.0028 (9)	0.0148 (10)
O2	0.0612 (15)	0.118 (2)	0.0812 (17)	−0.0209 (14)	0.0233 (13)	0.0226 (16)
O3	0.0763 (14)	0.0448 (12)	0.0438 (11)	−0.0058 (10)	−0.0097 (10)	−0.0023 (9)
O4	0.1051 (18)	0.0539 (13)	0.0348 (11)	−0.0320 (12)	−0.0040 (11)	0.0037 (9)
C4	0.099 (5)	0.095 (5)	0.071 (5)	−0.018 (4)	−0.002 (4)	−0.001 (4)
S1	0.0613 (11)	0.093 (3)	0.077 (2)	−0.0054 (11)	0.0176 (11)	0.024 (2)
C7	0.069 (4)	0.065 (6)	0.068 (5)	−0.020 (4)	0.014 (3)	−0.008 (4)
S2	0.0988 (18)	0.0813 (11)	0.0849 (12)	−0.0531 (10)	0.0155 (10)	−0.0206 (9)
S1'	0.18 (2)	0.109 (13)	0.056 (4)	0.037 (15)	0.015 (7)	0.012 (5)
C4'	0.069 (15)	0.063 (16)	0.054 (16)	−0.033 (13)	0.005 (11)	0.008 (10)
C7'	0.08 (2)	0.25 (5)	0.12 (2)	0.03 (2)	−0.046 (17)	0.05 (2)
S2'	0.141 (11)	0.072 (4)	0.073 (4)	−0.055 (5)	0.026 (5)	−0.017 (3)

Geometric parameters (Å, º) top

C1—C4'	1.299 (15)	N6—H6	0.8600
C1—C2	1.357 (4)	C21—C20	1.336 (4)
C1—S1	1.721 (4)	C21—N5	1.386 (3)
C1—H1	0.9300	C21—H21	0.9300
C2—C3	1.395 (4)	C22—N11	1.312 (3)
C2—C5	1.495 (4)	C22—N12	1.330 (4)
C3—C4	1.307 (12)	C22—H22	0.9300
C3—S1'	1.735 (9)	C23—N12	1.339 (4)
C3—H3	0.9300	C23—C24	1.347 (4)
C5—C6	1.516 (4)	C23—H23	0.9300
C5—H5A	0.9700	C24—N11	1.368 (4)
C5—H5B	0.9700	C24—H24	0.9300
C6—O2	1.235 (3)	C25—N7	1.318 (3)
C6—O1	1.245 (3)	C25—N8	1.323 (4)
C8—C7	1.356 (12)	C25—H25	0.9300
C8—C9	1.401 (4)	C26—C27	1.355 (4)
C8—S2'	1.651 (10)	C26—N8	1.357 (4)
C8—H8	0.9300	C26—H26	0.9300
C9—C10	1.377 (5)	C27—N7	1.372 (4)
C9—C11	1.498 (4)	C27—H27	0.9300
C10—C7'	1.350 (15)	C28—N9	1.320 (3)
C10—S2	1.677 (4)	C28—N10	1.327 (3)
C10—H10	0.9300	C28—H28	0.9300
C11—C12	1.522 (4)	C29—C30	1.353 (4)
C11—H11A	0.9700	C29—N10	1.364 (4)
C11—H11B	0.9700	C29—H29	0.9300
C12—O4	1.243 (3)	C30—N9	1.377 (4)
C12—O3	1.265 (3)	C30—H30	0.9300
C13—N1	1.315 (3)	N1—Ni1	2.127 (2)
C13—N2	1.334 (3)	N2—H2	0.8600
C13—H13	0.9300	N3—Ni1	2.130 (2)
C14—N2	1.338 (4)	N4—H4A	0.8600
C14—C15	1.344 (4)	N5—Ni1	2.103 (2)
C14—H14	0.9300	C20—H20	0.9300
C15—N1	1.360 (4)	N7—Ni1	2.125 (2)
C15—H15	0.9300	N8—H8A	0.8600
C16—C17	1.342 (4)	N9—Ni1	2.149 (2)
C16—N3	1.384 (3)	N10—H10A	0.8600
C16—H16	0.9300	N11—Ni1	2.133 (2)
C17—N4	1.340 (4)	N12—H12	0.8600
C17—H17	0.9300	C4—S1	1.783 (13)
C18—N3	1.318 (3)	C4—H4	0.9300
C18—N4	1.339 (3)	C7—S2	1.796 (12)
C18—H18	0.9300	C7—H7	0.9300
C19—N5	1.319 (3)	S1'—C4'	1.782 (14)
C19—N6	1.335 (3)	C4'—H4'	0.9300
C19—H19	0.9300	C7'—S2'	1.792 (14)
N6—C20	1.351 (4)	C7'—H7'	0.9300

C4'—C1—C2	126.7 (11)	C27—C26—N8	106.2 (3)
C2—C1—S1	111.0 (3)	C27—C26—H26	126.9
C4'—C1—H1	108.8	N8—C26—H26	126.9
C2—C1—H1	124.5	C26—C27—N7	109.7 (3)
S1—C1—H1	124.5	C26—C27—H27	125.2
C1—C2—C3	111.1 (3)	N7—C27—H27	125.2
C1—C2—C5	123.2 (3)	N9—C28—N10	112.4 (3)
C3—C2—C5	125.7 (3)	N9—C28—H28	123.8
C4—C3—C2	119.1 (7)	N10—C28—H28	123.8
C2—C3—S1'	105.0 (6)	C30—C29—N10	106.4 (3)
C4—C3—H3	120.4	C30—C29—H29	126.8
C2—C3—H3	120.4	N10—C29—H29	126.8
S1'—C3—H3	134.6	C29—C30—N9	109.6 (3)
C2—C5—C6	117.1 (3)	C29—C30—H30	125.2
C2—C5—H5A	108.0	N9—C30—H30	125.2
C6—C5—H5A	108.0	C13—N1—C15	104.1 (2)
C2—C5—H5B	108.0	C13—N1—Ni1	126.26 (18)
C6—C5—H5B	108.0	C15—N1—Ni1	129.40 (18)
H5A—C5—H5B	107.3	C13—N2—C14	106.7 (2)
O2—C6—O1	126.1 (3)	C13—N2—H2	126.7
O2—C6—C5	115.1 (3)	C14—N2—H2	126.7
O1—C6—C5	118.7 (3)	C18—N3—C16	104.6 (2)
C7—C8—C9	116.7 (6)	C18—N3—Ni1	128.34 (18)
C9—C8—S2'	110.8 (6)	C16—N3—Ni1	125.55 (18)
C7—C8—H8	121.6	C18—N4—C17	107.4 (2)
C9—C8—H8	121.6	C18—N4—H4A	126.3
S2'—C8—H8	127.5	C17—N4—H4A	126.3
C10—C9—C8	110.9 (3)	C19—N5—C21	104.2 (2)
C10—C9—C11	124.2 (3)	C19—N5—Ni1	126.72 (18)
C8—C9—C11	124.9 (3)	C21—N5—Ni1	129.02 (18)
C7'—C10—C9	119.1 (12)	C21—C20—N6	107.1 (3)
C9—C10—S2	113.1 (3)	C21—C20—H20	126.5
C7'—C10—H10	117.4	N6—C20—H20	126.5
C9—C10—H10	123.4	C25—N7—C27	104.4 (2)
S2—C10—H10	123.4	C25—N7—Ni1	128.32 (19)
C9—C11—C12	114.9 (2)	C27—N7—Ni1	127.25 (19)
C9—C11—H11A	108.6	C25—N8—C26	107.2 (2)
C12—C11—H11A	108.6	C25—N8—H8A	126.4
C9—C11—H11B	108.6	C26—N8—H8A	126.4
C12—C11—H11B	108.6	C28—N9—C30	104.6 (2)
H11A—C11—H11B	107.5	C28—N9—Ni1	125.81 (19)
O4—C12—O3	123.2 (3)	C30—N9—Ni1	128.84 (19)
O4—C12—C11	119.3 (3)	C28—N10—C29	107.0 (2)
O3—C12—C11	117.4 (2)	C28—N10—H10A	126.5
N1—C13—N2	112.3 (2)	C29—N10—H10A	126.5
N1—C13—H13	123.9	C22—N11—C24	104.6 (2)
N2—C13—H13	123.9	C22—N11—Ni1	128.08 (19)
N2—C14—C15	106.8 (3)	C24—N11—Ni1	127.36 (18)
N2—C14—H14	126.6	C22—N12—C23	107.2 (3)
C15—C14—H14	126.6	C22—N12—H12	126.4
C14—C15—N1	110.2 (3)	C23—N12—H12	126.4
C14—C15—H15	124.9	N5—Ni1—N7	89.81 (8)
N1—C15—H15	124.9	N5—Ni1—N1	90.40 (8)
C17—C16—N3	109.3 (3)	N7—Ni1—N1	89.69 (8)
C17—C16—H16	125.4	N5—Ni1—N3	89.52 (8)
N3—C16—H16	125.4	N7—Ni1—N3	177.57 (8)
N4—C17—C16	107.3 (3)	N1—Ni1—N3	92.65 (8)
N4—C17—H17	126.4	N5—Ni1—N11	179.43 (8)
C16—C17—H17	126.4	N7—Ni1—N11	90.73 (8)
N3—C18—N4	111.5 (3)	N1—Ni1—N11	89.78 (8)
N3—C18—H18	124.3	N3—Ni1—N11	89.93 (8)
N4—C18—H18	124.3	N5—Ni1—N9	90.79 (8)
N5—C19—N6	111.9 (3)	N7—Ni1—N9	89.38 (8)
N5—C19—H19	124.0	N1—Ni1—N9	178.48 (8)
N6—C19—H19	124.0	N3—Ni1—N9	88.30 (8)
C19—N6—C20	107.1 (2)	N11—Ni1—N9	89.04 (8)
C19—N6—H6	126.5	C3—C4—S1	106.7 (10)
C20—N6—H6	126.5	C3—C4—H4	126.7
C20—C21—N5	109.6 (3)	S1—C4—H4	126.7
C20—C21—H21	125.2	C1—S1—C4	92.1 (5)
N5—C21—H21	125.2	C8—C7—S2	107.0 (8)
N11—C22—N12	112.0 (3)	C8—C7—H7	126.5
N11—C22—H22	124.0	S2—C7—H7	126.5
N12—C22—H22	124.0	C10—S2—C7	92.2 (4)
N12—C23—C24	106.7 (3)	C3—S1'—C4'	97.7 (11)
N12—C23—H23	126.6	C1—C4'—S1'	99.2 (15)
C24—C23—H23	126.6	C1—C4'—H4'	130.4
C23—C24—N11	109.5 (3)	S1'—C4'—H4'	130.4
C23—C24—H24	125.2	C10—C7'—S2'	104.2 (16)
N11—C24—H24	125.2	C10—C7'—H7'	127.9
N7—C25—N8	112.5 (3)	S2'—C7'—H7'	127.9
N7—C25—H25	123.7	C8—S2'—C7'	94.9 (11)
N8—C25—H25	123.7

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N12—H12···O4ⁱ	0.86	2.56	3.124 (3)	124
N12—H12···O3ⁱ	0.86	1.97	2.826 (3)	170
N10—H10A···O3ⁱⁱ	0.86	1.88	2.718 (3)	164
N8—H8A···O2ⁱⁱⁱ	0.86	1.81	2.660 (3)	170
N4—H4A···O4^iv	0.86	1.89	2.688 (3)	153
N2—H2···O1^v	0.86	1.91	2.749 (3)	166
N6—H6···O1ⁱⁱ	0.86	1.90	2.711 (3)	156

Symmetry codes: (i) −x+1, −y+2, −z+2; (ii) x+1, y, z; (iii) −x+2, −y+2, −z+1; (iv) −x+1, −y+1, −z+2; (v) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	[Ni(C₃H₄N₂)₆](C₆H₅O₂S)₂
M_r	749.52
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	9.2483 (3), 9.8529 (3), 19.6365 (6)
α, β, γ (°)	84.696 (1), 88.380 (2), 80.157 (2)
V (Å³)	1755.30 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.73
Crystal size (mm)	0.20 × 0.16 × 0.11

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.869, 0.925
No. of measured, independent and observed [I > 2σ(I)] reflections	13333, 7140, 5337
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.111, 1.06
No. of reflections	7140
No. of parameters	480
No. of restraints	38
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.27

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N12—H12···O4ⁱ	0.86	2.56	3.124 (3)	124.2
N12—H12···O3ⁱ	0.86	1.97	2.826 (3)	170.1
N10—H10A···O3ⁱⁱ	0.86	1.88	2.718 (3)	164.0
N8—H8A···O2ⁱⁱⁱ	0.86	1.81	2.660 (3)	169.5
N4—H4A···O4^iv	0.86	1.89	2.688 (3)	153.3
N2—H2···O1^v	0.86	1.91	2.749 (3)	165.9
N6—H6···O1ⁱⁱ	0.86	1.90	2.711 (3)	156.0

Symmetry codes: (i) −x+1, −y+2, −z+2; (ii) x+1, y, z; (iii) −x+2, −y+2, −z+1; (iv) −x+1, −y+1, −z+2; (v) −x+1, −y+2, −z+1.

Acknowledgements

The authors acknowledge Guang Dong Ocean University for supporting this work.

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ng, S. W., Chantrapromma, S., Razak, I. A. & Fun, H.-K. (2001). Acta Cryst. C57, 291–292. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar